Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Maria Gdaniec' _publ_contact_author_address ; Faculty of Chemistry Adam Mickiewicz University Poznan 60-780 POLAND ; _publ_contact_author_email MAGDAN@AMU.EDU.PL _publ_section_title ; Co-crystals of iodopentafluorobenzene with nitrogen donors: 2D molecular assemblies through halogen bonding and aryl-perfluoroaryl interactions ; loop_ _publ_author_name M.Gdaniec T.Polonski A.Wasilewska data_1.2 _database_code_depnum_ccdc_archive 'CCDC 618383' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4,6-trimethylpyridine pentafluoroiodobenzene ; _chemical_name_common '2,4,6-trimethylpyridine pentafluoroiodobenzene' _chemical_melting_point ? _chemical_formula_moiety 'C6 F5 I, C8 H11 N' _chemical_formula_sum 'C14 H11 F5 I N' _chemical_formula_weight 415.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.5677(4) _cell_length_b 16.7343(6) _cell_length_c 11.6003(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1469.06(10) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3251 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.877 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 2.226 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.46 _exptl_absorpt_correction_T_max 0.82 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'Kuma KM4CCD \k geometry' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 5803 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0139 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.28 _diffrn_reflns_theta_max 26.35 _reflns_number_total 1501 _reflns_number_gt 1191 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_cell_refinement ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_data_reduction ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989). Mercury, Version 1.3 (Bruno et al., 2002) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+0.4024P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0049(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1501 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0193 _refine_ls_wR_factor_ref 0.0514 _refine_ls_wR_factor_gt 0.0490 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.5000 0.652542(11) 0.2500 0.01996(10) Uani 1 2 d S . . F2 F 0.64670(16) 0.52142(8) 0.43019(10) 0.0284(3) Uani 1 1 d . . . F3 F 0.6432(2) 0.36063(8) 0.43057(12) 0.0401(4) Uani 1 1 d . . . F4 F 0.5000 0.27904(13) 0.2500 0.0468(6) Uani 1 2 d S . . C1 C 0.5000 0.52640(18) 0.2500 0.0186(6) Uani 1 2 d S . . C2 C 0.5724(3) 0.48315(13) 0.34012(17) 0.0214(5) Uani 1 1 d . . . C3 C 0.5722(3) 0.40065(14) 0.3416(2) 0.0273(5) Uani 1 1 d . . . C4 C 0.5000 0.35939(19) 0.2500 0.0276(8) Uani 1 2 d S . . N1A N 0.5000 0.82363(17) 0.2500 0.0200(5) Uani 1 2 d S . . C2A C 0.5608(3) 0.86485(14) 0.1583(2) 0.0245(5) Uani 1 1 d . . . C3A C 0.5615(3) 0.94767(14) 0.15583(19) 0.0246(5) Uani 1 1 d . . . H3A H 0.6033 0.9744 0.0910 0.030 Uiso 1 1 calc R . . C4A C 0.5000 0.9910(2) 0.2500 0.0246(7) Uani 1 2 d S . . C5A C 0.6249(3) 0.81649(14) 0.05737(19) 0.0338(6) Uani 1 1 d . . . H5A H 0.7110 0.7728 0.0976 0.041 Uiso 1 1 d R . . H5BA H 0.5269 0.7877 0.0211 0.041 Uiso 1 1 d R . . H5CA H 0.7020 0.8466 0.0052 0.041 Uiso 1 1 d R . . C6A C 0.5000 1.0806(2) 0.2500 0.0332(8) Uani 1 2 d S . . H6AC H 0.5477 1.0963 0.3231 0.040 Uiso 0.50 1 d PR . . H6AD H 0.5853 1.0963 0.1932 0.040 Uiso 0.50 1 d PR . . H6AE H 0.4107 1.1103 0.2390 0.040 Uiso 0.50 1 d PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.01870(13) 0.01716(14) 0.02402(13) 0.000 0.00095(8) 0.000 F2 0.0280(7) 0.0346(7) 0.0227(6) 0.0013(6) -0.0036(5) -0.0030(6) F3 0.0446(9) 0.0354(8) 0.0403(8) 0.0197(7) 0.0036(7) 0.0072(7) F4 0.0629(16) 0.0126(10) 0.0648(15) 0.000 0.0151(11) 0.000 C1 0.0148(13) 0.0194(16) 0.0215(14) 0.000 0.0069(12) 0.000 C2 0.0183(10) 0.0246(12) 0.0211(11) -0.0002(9) 0.0029(9) -0.0018(10) C3 0.0243(11) 0.0271(12) 0.0303(12) 0.0092(10) 0.0079(11) 0.0052(11) C4 0.0308(19) 0.0129(16) 0.039(2) 0.000 0.0116(15) 0.000 N1A 0.0216(13) 0.0174(12) 0.0209(13) 0.000 0.0005(11) 0.000 C2A 0.0220(11) 0.0260(12) 0.0254(11) 0.0027(10) -0.0018(10) -0.0035(10) C3A 0.0210(10) 0.0238(12) 0.0290(11) 0.0058(10) -0.0027(9) -0.0041(10) C4A 0.0153(14) 0.0191(16) 0.0393(18) 0.000 -0.0087(14) 0.000 C5A 0.0463(16) 0.0300(14) 0.0251(12) -0.0012(10) 0.0105(11) -0.0071(11) C6A 0.0204(16) 0.0262(19) 0.053(2) 0.000 -0.0061(16) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.111(3) . ? F2 C2 1.348(2) . ? F3 C3 1.343(3) . ? F4 C4 1.344(3) . ? C1 C2 1.385(3) . ? C2 C3 1.381(3) . ? C3 C4 1.380(3) . ? N1A C2A 1.349(3) . ? C2A C3A 1.386(3) . ? C2A C5A 1.504(3) . ? C3A C4A 1.391(3) . ? C3A H3A 0.9300 . ? C4A C6A 1.500(5) . ? C5A H5A 1.0852 . ? C5A H5BA 0.9796 . ? C5A H5CA 0.9794 . ? C6A H6AC 0.9585 . ? C6A H6AD 0.9585 . ? C6A H6AE 0.8478 . ? 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 C2 117.0(3) 3_655 . ? C2 C1 I1 121.52(14) . . ? F2 C2 C3 117.8(2) . . ? F2 C2 C1 120.13(19) . . ? C3 C2 C1 122.1(2) . . ? F3 C3 C4 120.1(2) . . ? F3 C3 C2 120.5(2) . . ? C4 C3 C2 119.5(2) . . ? F4 C4 C3 120.04(15) . . ? C3 C4 C3 119.9(3) 3_655 . ? C2A N1A C2A 118.5(3) . 3_655 ? N1A C2A C3A 121.9(2) . . ? N1A C2A C5A 116.7(2) . . ? C3A C2A C5A 121.4(2) . . ? C2A C3A C4A 120.2(2) . . ? C2A C3A H3A 119.9 . . ? C4A C3A H3A 119.9 . . ? C3A C4A C3A 117.2(3) . 3_655 ? C3A C4A C6A 121.40(16) . . ? C2A C5A H5A 102.8 . . ? C2A C5A H5BA 110.8 . . ? H5A C5A H5BA 107.9 . . ? C2A C5A H5CA 113.4 . . ? H5A C5A H5CA 104.8 . . ? H5BA C5A H5CA 116.0 . . ? C4A C6A H6AC 105.8 . . ? C4A C6A H6AD 105.8 . . ? H6AC C6A H6AD 106.2 . . ? C4A C6A H6AE 125.8 . . ? H6AC C6A H6AE 105.9 . . ? H6AD C6A H6AE 105.9 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.830 _refine_diff_density_min -0.454 _refine_diff_density_rms 0.084 #===END data_1-3 _database_code_depnum_ccdc_archive 'CCDC 618384' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,6-dimethylpyridine pentafluoroiodobenzene 1/1 adduct ; _chemical_name_common '2,6-dimethylpyridine pentafluoroiodobenzene 1/1 adduct' _chemical_melting_point ? _chemical_formula_moiety 'C6 F5 I, C7 H9 N' _chemical_formula_sum 'C13 H9 F5 I N' _chemical_formula_weight 401.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' 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 7.3936(9) _cell_length_b 15.4467(19) _cell_length_c 12.0105(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.881(10) _cell_angle_gamma 90.00 _cell_volume 1371.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2546 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.943 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 2.380 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min .414 _exptl_absorpt_correction_T_max .490 _exptl_absorpt_process_details ? _exptl_special_details ; crystals unstable in air ; _diffrn_ambient_temperature 130(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 'Kuma KM4CCD \k geometry' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 4193 _diffrn_reflns_av_R_equivalents 0.0155 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.30 _diffrn_reflns_theta_max 26.37 _reflns_number_total 1396 _reflns_number_gt 1306 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_cell_refinement ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_data_reduction ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989). Mercury, Version 1.3 (Bruno et al., 2002) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0291P)^2^+0.0223P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0020(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1396 _refine_ls_number_parameters 98 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0212 _refine_ls_R_factor_gt 0.0189 _refine_ls_wR_factor_ref 0.0454 _refine_ls_wR_factor_gt 0.0447 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.5000 0.652372(11) 0.7500 0.02896(10) Uani 1 2 d S . . F2 F 0.35771(18) 0.51158(9) 0.57264(11) 0.0345(3) Uani 1 1 d . . . F3 F 0.3604(2) 0.33793(9) 0.57243(15) 0.0498(4) Uani 1 1 d . . . F4 F 0.5000 0.24962(12) 0.7500 0.0635(7) Uani 1 2 d S . . C1 C 0.5000 0.51677(18) 0.7500 0.0218(6) Uani 1 2 d S . . C2 C 0.4295(3) 0.47011(14) 0.66091(17) 0.0246(5) Uani 1 1 d . . . C3 C 0.4290(3) 0.38151(16) 0.6602(2) 0.0327(5) Uani 1 1 d . . . C4 C 0.5000 0.33698(18) 0.7500 0.0361(8) Uani 1 2 d S . . N1A N 0.5000 0.84406(13) 0.7500 0.0220(5) Uani 1 2 d S . . C2A C 0.4461(3) 0.88888(13) 0.65886(16) 0.0225(4) Uani 1 1 d . . . C3A C 0.4429(3) 0.97839(13) 0.65708(17) 0.0237(4) Uani 1 1 d . . . H3AA H 0.4023 1.0072 0.5934 0.028 Uiso 1 1 calc R . . C4A C 0.5000 1.02585(19) 0.7500 0.0193(6) Uani 1 2 d S . . H4AA H 0.5000 1.0861 0.7500 0.023 Uiso 1 2 calc SR . . C5A C 0.3916(3) 0.83596(14) 0.5588(2) 0.0316(5) Uani 1 1 d G . . H5AA H 0.3018 0.7946 0.5798 0.047 Uiso 1 1 calc G . . H5AB H 0.4966 0.8062 0.5329 0.047 Uiso 1 1 calc G . . H5AC H 0.3439 0.8722 0.5005 0.047 Uiso 1 1 calc G . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.02715(14) 0.02199(13) 0.03778(15) 0.000 0.00199(8) 0.000 F2 0.0287(7) 0.0494(8) 0.0253(7) -0.0002(6) -0.0028(5) 0.0055(6) F3 0.0395(9) 0.0499(9) 0.0601(10) -0.0327(7) 0.0002(8) -0.0040(6) F4 0.0580(15) 0.0186(10) 0.114(2) 0.000 0.0063(14) 0.000 C1 0.0165(14) 0.0217(14) 0.0274(15) 0.000 0.0044(12) 0.000 C2 0.0176(11) 0.0318(12) 0.0245(11) -0.0013(8) 0.0021(8) 0.0026(8) C3 0.0215(11) 0.0323(12) 0.0445(14) -0.0149(10) 0.0055(10) -0.0020(9) C4 0.0256(17) 0.0202(16) 0.063(2) 0.000 0.0101(16) 0.000 N1A 0.0213(13) 0.0194(12) 0.0251(13) 0.000 -0.0025(10) 0.000 C2A 0.0178(10) 0.0244(11) 0.0253(11) -0.0008(8) -0.0004(8) -0.0002(8) C3A 0.0201(11) 0.0262(11) 0.0249(11) 0.0055(8) 0.0026(9) 0.0035(8) C4A 0.0131(13) 0.0236(14) 0.0213(14) 0.000 0.0053(11) 0.000 C5A 0.0353(13) 0.0311(12) 0.0282(12) -0.0032(9) -0.0089(10) 0.0038(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.095(3) . ? F2 C2 1.341(2) . ? F3 C3 1.344(3) . ? F4 C4 1.350(3) . ? C1 C2 1.385(3) . ? C2 C3 1.369(3) . ? C3 C4 1.376(3) . ? N1A C2A 1.350(2) . ? C2A C3A 1.383(3) . ? C2A C5A 1.503(3) . ? C3A C4A 1.395(3) . ? C3A H3AA 0.9300 . ? C4A H4AA 0.9300 . ? C5A H5AA 0.9582 . ? C5A H5AB 0.9582 . ? C5A H5AC 0.9587 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C2 117.3(3) . 6_657 ? C2 C1 I1 121.35(13) . . ? F2 C2 C3 118.17(19) . . ? F2 C2 C1 120.12(19) . . ? C3 C2 C1 121.7(2) . . ? F3 C3 C2 120.4(2) . . ? F3 C3 C4 120.0(2) . . ? C2 C3 C4 119.6(2) . . ? F4 C4 C3 119.99(14) . . ? C3 C4 C3 120.0(3) 6_657 . ? C2A N1A C2A 118.3(2) 6_657 . ? N1A C2A C3A 122.00(19) . . ? N1A C2A C5A 116.20(19) . . ? C3A C2A C5A 121.80(19) . . ? C2A C3A C4A 120.5(2) . . ? C2A C3A H3AA 119.7 . . ? C4A C3A H3AA 119.7 . . ? C3A C4A C3A 116.6(3) . 6_657 ? C3A C4A H4AA 121.7 . . ? C2A C5A H5AA 109.3 . . ? C2A C5A H5AB 108.2 . . ? H5AA C5A H5AB 109.5 . . ? C2A C5A H5AC 110.9 . . ? H5AA C5A H5AC 109.5 . . ? H5AB C5A H5AC 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.409 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.066 #===END data_1.4 _database_code_depnum_ccdc_archive 'CCDC 618385' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-dimethlpyridine pentafluoroiodobenzene ; _chemical_name_common '3,5-dimethlpyridine pentafluoroiodobenzene' _chemical_melting_point ? _chemical_formula_moiety 'C6 F5 I, C7 H9 N' _chemical_formula_sum 'C13 H9 F5 I N' _chemical_formula_weight 401.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' 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 7.2401(8) _cell_length_b 15.1648(14) _cell_length_c 12.9908(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.574(8) _cell_angle_gamma 90.00 _cell_volume 1425.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 2958 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.869 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 2.290 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min .46 _exptl_absorpt_correction_T_max .52 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 'Kuma KM4CCD \k geometry' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 4435 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 26.37 _reflns_number_total 1448 _reflns_number_gt 1353 _reflns_threshold_expression >2\s(I) _computing_data_collection ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_cell_refinement ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_data_reduction ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989). Mercury, Version 1.3 (Bruno et al., 2002) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+2.2675P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1448 _refine_ls_number_parameters 94 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0285 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0660 _refine_ls_wR_factor_gt 0.0645 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.5000 0.293643(17) 0.2500 0.04534(12) Uani 1 2 d S . . F2 F 0.6228(3) 0.15068(18) 0.41961(17) 0.0710(6) Uani 1 1 d . . . F3 F 0.6270(4) -0.0259(2) 0.4189(3) 0.1247(15) Uani 1 1 d . . . F4 F 0.5000 -0.1158(2) 0.2500 0.159(3) Uani 1 2 d S . . C1 C 0.5000 0.1531(3) 0.2500 0.0421(9) Uani 1 2 d S . . C2 C 0.5614(4) 0.1081(2) 0.3350(3) 0.0506(8) Uani 1 1 d . . . C3 C 0.5623(5) 0.0178(3) 0.3347(4) 0.0764(15) Uani 1 1 d . . . C4 C 0.5000 -0.0272(4) 0.2500 0.095(3) Uani 1 2 d S . . N1A N 0.5000 0.4803(2) 0.2500 0.0490(9) Uani 1 2 d S . . C2A C 0.4527(4) 0.5247(2) 0.1655(2) 0.0425(7) Uani 1 1 d . . . H2AA H 0.4173 0.4919 0.1049 0.051 Uiso 1 1 d R . . C3A C 0.4517(4) 0.6156(2) 0.1606(2) 0.0377(6) Uani 1 1 d . . . C4A C 0.5000 0.6611(3) 0.2500 0.0359(8) Uani 1 2 d S . . H4AA H 0.5000 0.7245 0.2500 0.043 Uiso 1 2 d SR . . C5A C 0.4003(5) 0.6644(3) 0.0638(3) 0.0586(9) Uani 1 1 d . . . H5AA H 0.4095 0.7266 0.0771 0.070 Uiso 1 1 d R . . H5AB H 0.2730 0.6519 0.0470 0.070 Uiso 1 1 d R . . H5AC H 0.4565 0.6542 0.0168 0.070 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.04912(19) 0.03843(17) 0.04883(19) 0.000 0.00814(12) 0.000 F2 0.0568(13) 0.0981(18) 0.0580(13) 0.0201(12) -0.0020(10) 0.0063(12) F3 0.089(2) 0.105(2) 0.183(4) 0.096(2) 0.047(2) 0.0395(17) F4 0.113(4) 0.0303(16) 0.337(9) 0.000 0.097(5) 0.000 C1 0.0207(17) 0.060(3) 0.046(2) 0.000 0.0093(15) 0.000 C2 0.0300(14) 0.0583(19) 0.064(2) 0.0169(16) 0.0073(14) 0.0054(13) C3 0.044(2) 0.055(2) 0.132(4) 0.042(3) 0.033(2) 0.0148(17) C4 0.057(3) 0.033(3) 0.198(9) 0.000 0.058(5) 0.000 N1A 0.050(2) 0.0370(19) 0.061(2) 0.000 0.0070(18) 0.000 C2A 0.0376(15) 0.0458(16) 0.0443(17) -0.0121(13) 0.0046(12) -0.0002(12) C3A 0.0317(13) 0.0444(15) 0.0369(15) -0.0002(12) 0.0018(11) 0.0016(11) C4A 0.0320(19) 0.0307(19) 0.045(2) 0.000 0.0004(16) 0.000 C5A 0.061(2) 0.073(2) 0.0418(18) 0.0064(17) -0.0062(15) 0.0071(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.131(5) . ? F2 C2 1.340(5) . ? F3 C3 1.352(6) . ? F4 C4 1.344(7) . ? C1 C2 1.363(4) . ? C2 C3 1.368(5) . ? C3 C4 1.361(6) . ? N1A C2A 1.325(4) . ? C2A C3A 1.380(4) . ? C3A C4A 1.387(3) . ? C3A C5A 1.498(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 C2 C1 C2 119.8(5) . 6_656 ? C2 C1 I1 120.1(2) . . ? F2 C2 C1 121.1(3) . . ? F2 C2 C3 118.9(4) . . ? C1 C2 C3 120.0(4) . . ? F3 C3 C4 120.5(4) . . ? F3 C3 C2 119.3(5) . . ? C4 C3 C2 120.2(5) . . ? F4 C4 C3 120.1(3) . . ? C3 C4 C3 119.8(5) . 6_656 ? C2A N1A C2A 118.9(4) 6_656 . ? N1A C2A C3A 123.1(3) . . ? C2A C3A C4A 117.2(3) . . ? C2A C3A C5A 122.2(3) . . ? C4A C3A C5A 120.6(3) . . ? C3A C4A C3A 120.3(4) . 6_656 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.402 _refine_diff_density_min -0.684 _refine_diff_density_rms 0.081 #===END data_1.4lt _database_code_depnum_ccdc_archive 'CCDC 618386' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3,5-dimethylpyridine pentafluoroiodobenzene ; _chemical_name_common '3,5-dimethylpyridine pentafluoroiodobenzene' _chemical_melting_point ? _chemical_formula_moiety 'C6 F 5I, C7 H9 N' _chemical_formula_sum 'C13 H9 F5 I N' _chemical_formula_weight 401.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' 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 7.2792(5) _cell_length_b 12.9453(7) _cell_length_c 15.2214(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.479(6) _cell_angle_gamma 90.00 _cell_volume 1427.78(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2877 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.866 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 2.287 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.45 _exptl_absorpt_correction_T_max 0.53 _exptl_absorpt_process_details ? _exptl_special_details ; low-temperature phase (phase transition at 168K) is twinned with the twin matrix -1 0 0 0 -1 0 0.4024 0 1. ; _diffrn_ambient_temperature 150(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 'Kuma KM4CCD \k geometry' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 2149 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -2 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 4.14 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2149 _reflns_number_gt 2039 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_cell_refinement ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_data_reduction ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989). Mercury, Version 1.3 (Bruno et al., 2002) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _refine_special_details ; The crystal is a twin as a result of the phase transition at 168K. It has been refined with hklf 5 instruction with shelxl-98. Low data completness results from removal of reflections for which a correct peak integration could not be done. The BASF parameter value refined at 0.462. ; _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^)+(0.0905P)^2^+15.3689P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2149 _refine_ls_number_parameters 182 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0689 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1881 _refine_ls_wR_factor_gt 0.1865 _refine_ls_goodness_of_fit_ref 1.190 _refine_ls_restrained_S_all 1.187 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1A N 0.5160(19) 0.2577(8) 0.4801(6) 0.034(3) Uani 1 1 d . . . C2A C 0.4711(18) 0.1724(9) 0.5218(8) 0.025(3) Uani 1 1 d . . . H2A H 0.4403 0.1139 0.4880 0.030 Uiso 1 1 d R . . C3A C 0.4687(18) 0.1658(8) 0.6128(7) 0.020(2) Uani 1 1 d U . . C4A C 0.5183(15) 0.2567(9) 0.6610(7) 0.021(2) Uani 1 1 d . . . H4A H 0.5204 0.2560 0.7222 0.025 Uiso 1 1 d R . . C5A C 0.5644(17) 0.3457(8) 0.6197(7) 0.020(2) Uani 1 1 d U . . C6A C 0.562(2) 0.3423(10) 0.5268(8) 0.028(3) Uani 1 1 d . . . H6A H 0.5954 0.4014 0.4974 0.034 Uiso 1 1 d R . . C7A C 0.418(2) 0.0680(11) 0.6584(11) 0.037(3) Uani 1 1 d . . . H7AC H 0.3880 0.0149 0.6154 0.056 Uiso 1 1 d R . . H7AB H 0.3125 0.0815 0.6901 0.056 Uiso 1 1 d R . . H7AA H 0.5192 0.0457 0.6989 0.056 Uiso 1 1 d R . . C8A C 0.613(3) 0.4435(11) 0.6706(9) 0.040(4) Uani 1 1 d . . . H8AC H 0.6064 0.4319 0.7325 0.060 Uiso 1 1 d R . . H8AB H 0.5274 0.4972 0.6507 0.060 Uiso 1 1 d R . . H8AA H 0.7355 0.4639 0.6603 0.060 Uiso 1 1 d R . . I1 I 0.51872(11) 0.25118(6) 0.29366(4) 0.0247(3) Uani 1 1 d . . . F2 F 0.4003(13) 0.4134(5) 0.1369(5) 0.0334(18) Uani 1 1 d . . . F3 F 0.4029(15) 0.4031(7) -0.0403(5) 0.050(2) Uani 1 1 d . . . F4 F 0.5316(15) 0.2285(9) -0.1164(5) 0.059(3) Uani 1 1 d . . . F5 F 0.6524(14) 0.0634(6) -0.0140(5) 0.044(2) Uani 1 1 d . . . F6 F 0.6398(15) 0.0715(6) 0.1629(5) 0.041(2) Uani 1 1 d . . . C1 C 0.5209(14) 0.2425(8) 0.1534(7) 0.020(2) Uani 1 1 d . . . C2 C 0.4610(19) 0.3266(9) 0.1006(7) 0.023(2) Uani 1 1 d . . . C3 C 0.466(2) 0.3220(11) 0.0105(8) 0.032(3) Uani 1 1 d . . . C4 C 0.526(3) 0.2325(13) -0.0274(8) 0.049(4) Uani 1 1 d . . . C5 C 0.585(2) 0.1501(11) 0.0244(9) 0.033(3) Uani 1 1 d . . . C6 C 0.5808(19) 0.1553(9) 0.1133(8) 0.026(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1A 0.053(7) 0.034(5) 0.016(4) 0.000(4) 0.003(5) 0.008(7) C2A 0.014(5) 0.031(6) 0.031(6) -0.005(5) 0.001(5) 0.002(5) C3A 0.020(2) 0.021(2) 0.020(2) 0.0003(10) 0.0020(10) -0.0003(10) C4A 0.017(5) 0.027(5) 0.020(5) 0.008(5) 0.003(4) 0.007(6) C5A 0.020(2) 0.020(2) 0.020(2) 0.0001(10) 0.0019(10) 0.0003(10) C6A 0.031(7) 0.031(6) 0.024(6) 0.006(5) 0.001(6) 0.010(6) C7A 0.025(7) 0.037(7) 0.050(9) 0.010(6) 0.003(7) -0.005(6) C8A 0.046(10) 0.036(7) 0.036(7) -0.009(6) -0.001(8) -0.001(8) I1 0.0281(4) 0.0299(4) 0.0161(4) -0.0009(3) 0.0028(3) -0.0016(4) F2 0.032(4) 0.025(3) 0.043(4) 0.004(3) -0.001(4) 0.001(4) F3 0.046(6) 0.061(5) 0.041(5) 0.028(4) -0.004(4) -0.013(5) F4 0.053(6) 0.113(8) 0.013(3) 0.000(4) 0.009(4) -0.003(6) F5 0.036(5) 0.053(5) 0.045(5) -0.026(4) 0.015(4) 0.000(4) F6 0.054(6) 0.027(4) 0.041(4) -0.001(3) 0.003(5) 0.009(4) C1 0.014(4) 0.017(5) 0.030(5) 0.005(5) 0.011(4) -0.005(5) C2 0.021(6) 0.024(5) 0.025(6) 0.005(4) 0.006(5) 0.005(5) C3 0.019(6) 0.056(8) 0.021(6) 0.018(6) 0.003(5) 0.002(6) C4 0.057(10) 0.076(11) 0.011(5) -0.008(6) -0.008(7) -0.023(10) C5 0.024(7) 0.044(7) 0.033(7) -0.014(6) 0.007(6) -0.008(6) C6 0.024(6) 0.024(6) 0.029(6) 0.001(5) 0.002(6) -0.004(6) _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 N1A C2A 1.330(16) . ? N1A C6A 1.331(16) . ? C2A C3A 1.390(16) . ? C3A C4A 1.416(15) . ? C3A C7A 1.507(17) . ? C4A C5A 1.370(15) . ? C5A C6A 1.412(16) . ? C5A C8A 1.508(17) . ? I1 C1 2.140(11) . ? F2 C2 1.346(14) . ? F3 C3 1.358(15) . ? F4 C4 1.360(14) . ? F5 C5 1.376(16) . ? F6 C6 1.368(14) . ? C1 C6 1.374(17) . ? C1 C2 1.398(15) . ? C2 C3 1.376(16) . ? C3 C4 1.38(2) . ? C4 C5 1.37(2) . ? C5 C6 1.358(18) . ? 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 C2A N1A C6A 119.3(10) . . ? N1A C2A C3A 123.6(11) . . ? C2A C3A C4A 116.0(10) . . ? C2A C3A C7A 122.5(11) . . ? C4A C3A C7A 121.4(11) . . ? C5A C4A C3A 121.5(10) . . ? C4A C5A C6A 116.9(10) . . ? C4A C5A C8A 121.7(11) . . ? C6A C5A C8A 121.4(11) . . ? N1A C6A C5A 122.6(11) . . ? C6 C1 C2 118.6(11) . . ? C6 C1 I1 121.3(8) . . ? C2 C1 I1 120.1(8) . . ? F2 C2 C3 119.1(11) . . ? F2 C2 C1 120.7(10) . . ? C3 C2 C1 120.2(11) . . ? F3 C3 C2 119.6(13) . . ? F3 C3 C4 120.9(12) . . ? C2 C3 C4 119.4(12) . . ? F4 C4 C5 120.3(15) . . ? F4 C4 C3 119.2(14) . . ? C5 C4 C3 120.4(11) . . ? C6 C5 C4 119.9(13) . . ? C6 C5 F5 120.5(13) . . ? C4 C5 F5 119.7(12) . . ? C5 C6 F6 118.3(12) . . ? C5 C6 C1 121.5(12) . . ? F6 C6 C1 120.2(11) . . ? _diffrn_measured_fraction_theta_max 0.852 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.852 _refine_diff_density_max 2.736 _refine_diff_density_min -1.550 _refine_diff_density_rms 0.198 # Formatted by publCIF #===END data_1.5 _database_code_depnum_ccdc_archive 'CCDC 618387' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-methylpyridine pentafluoroiodobenzene ; _chemical_name_common '4-methylpyridine pentafluoroiodobenzene' _chemical_melting_point ? _chemical_formula_moiety 'C6 F5 I, C6 H7 N' _chemical_formula_sum 'C12 H7 F5 I N' _chemical_formula_weight 387.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 7.2888(6) _cell_length_b 14.1251(11) _cell_length_c 12.6561(11) _cell_angle_alpha 90.00 _cell_angle_beta 95.502(7) _cell_angle_gamma 90.00 _cell_volume 1297.01(19) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2677 _cell_measurement_theta_min 4 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.982 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 2.513 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min .325 _exptl_absorpt_correction_T_max .605 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 'Kuma KM4CCD \k geometry' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% 0 _diffrn_reflns_number 7937 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2633 _reflns_number_gt 2247 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_cell_refinement ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_data_reduction ; Oxford Diffraction, CrysAlis Software, Version 1.171, 2004 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Stereochemical Workstation (Siemens Analytical X-Ray Instruments, Inc., 1989). Mercury, Version 1.3 (Bruno et al., 2002) ; _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.6843P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0016(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2633 _refine_ls_number_parameters 176 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0627 _refine_ls_wR_factor_gt 0.0601 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.21918(2) 0.554691(12) 0.713602(15) 0.02587(9) Uani 1 1 d . . . F2 F 0.0694(2) 0.66127(12) 0.49622(14) 0.0335(4) Uani 1 1 d . . . F3 F 0.0410(2) 0.84484(13) 0.44341(14) 0.0392(5) Uani 1 1 d . . . F4 F 0.1683(3) 0.98079(13) 0.58535(18) 0.0463(5) Uani 1 1 d . . . F5 F 0.3135(3) 0.93063(13) 0.78264(17) 0.0427(5) Uani 1 1 d . . . F6 F 0.3383(2) 0.74698(13) 0.83825(14) 0.0330(4) Uani 1 1 d . . . C1 C 0.2051(4) 0.69798(19) 0.6689(2) 0.0220(6) Uani 1 1 d . . . C2 C 0.1314(4) 0.7265(2) 0.5692(2) 0.0240(6) Uani 1 1 d . . . C3 C 0.1175(4) 0.8205(2) 0.5401(2) 0.0279(6) Uani 1 1 d . . . C4 C 0.1802(4) 0.8891(2) 0.6121(3) 0.0300(7) Uani 1 1 d . . . C5 C 0.2538(4) 0.8638(2) 0.7127(3) 0.0296(7) Uani 1 1 d . . . C6 C 0.2670(4) 0.7690(2) 0.7399(2) 0.0252(6) Uani 1 1 d . . . N1A N 0.2583(3) 0.36978(18) 0.79370(19) 0.0269(6) Uani 1 1 d . . . C2A C 0.2312(4) 0.2844(2) 0.7482(3) 0.0291(7) Uani 1 1 d . . . H2AA H 0.1848 0.2821 0.6772 0.035 Uiso 1 1 calc R . . C3A C 0.2684(4) 0.1998(2) 0.8006(2) 0.0272(7) Uani 1 1 d . . . H3AA H 0.2488 0.1426 0.7649 0.033 Uiso 1 1 calc R . . C4A C 0.3356(4) 0.2008(2) 0.9074(2) 0.0258(6) Uani 1 1 d . . . C5A C 0.3636(4) 0.2893(2) 0.9545(3) 0.0287(7) Uani 1 1 d . . . H5AA H 0.4086 0.2939 1.0256 0.034 Uiso 1 1 calc R . . C6A C 0.3246(4) 0.3699(2) 0.8954(3) 0.0286(6) Uani 1 1 d . . . H6AA H 0.3459 0.4282 0.9286 0.034 Uiso 1 1 calc R . . C7A C 0.3755(5) 0.1109(2) 0.9689(3) 0.0380(8) Uani 1 1 d G . . H7AA H 0.3924 0.1251 1.0434 0.057 Uiso 1 1 calc G . . H7AB H 0.2703 0.0703 0.9548 0.057 Uiso 1 1 calc G . . H7AC H 0.4834 0.0796 0.9480 0.057 Uiso 1 1 calc G . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.02834(13) 0.02333(12) 0.02661(13) 0.00403(8) 0.00612(8) 0.00301(7) F2 0.0387(10) 0.0368(10) 0.0240(9) -0.0034(8) -0.0017(8) -0.0014(8) F3 0.0425(11) 0.0465(11) 0.0282(10) 0.0144(8) 0.0007(8) 0.0120(9) F4 0.0561(13) 0.0240(9) 0.0593(14) 0.0122(9) 0.0080(10) 0.0065(9) F5 0.0479(12) 0.0314(10) 0.0478(13) -0.0119(9) -0.0010(10) -0.0073(8) F6 0.0341(9) 0.0371(10) 0.0263(10) -0.0003(8) -0.0050(8) -0.0019(8) C1 0.0204(13) 0.0230(14) 0.0230(15) 0.0009(12) 0.0038(11) 0.0004(11) C2 0.0197(13) 0.0276(14) 0.0248(15) 0.0018(12) 0.0026(11) -0.0016(11) C3 0.0221(14) 0.0349(16) 0.0272(16) 0.0086(13) 0.0048(12) 0.0048(12) C4 0.0259(15) 0.0233(15) 0.0417(19) 0.0047(13) 0.0077(13) 0.0011(12) C5 0.0240(15) 0.0283(16) 0.0369(18) -0.0057(13) 0.0043(13) -0.0014(12) C6 0.0172(13) 0.0357(16) 0.0218(15) 0.0039(13) -0.0038(11) 0.0022(12) N1A 0.0281(13) 0.0266(13) 0.0262(14) 0.0038(11) 0.0040(11) 0.0009(10) C2A 0.0213(14) 0.0405(18) 0.0254(16) 0.0012(14) 0.0021(12) -0.0005(12) C3A 0.0265(15) 0.0259(15) 0.0300(18) -0.0010(12) 0.0060(13) -0.0036(11) C4A 0.0216(14) 0.0261(14) 0.0310(17) 0.0049(12) 0.0094(12) 0.0044(11) C5A 0.0267(15) 0.0340(16) 0.0254(16) 0.0016(13) 0.0025(12) 0.0035(12) C6A 0.0274(15) 0.0248(14) 0.0336(17) -0.0027(13) 0.0031(13) -0.0003(12) C7A 0.0440(19) 0.0296(17) 0.042(2) 0.0097(15) 0.0143(15) 0.0103(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.101(3) . ? F2 C2 1.351(3) . ? F3 C3 1.340(3) . ? F4 C4 1.339(3) . ? F5 C5 1.338(3) . ? F6 C6 1.339(3) . ? C1 C2 1.383(4) . ? C1 C6 1.393(4) . ? C2 C3 1.379(4) . ? C3 C4 1.377(4) . ? C4 C5 1.381(4) . ? C5 C6 1.383(4) . ? N1A C6A 1.331(4) . ? N1A C2A 1.343(4) . ? C2A C3A 1.381(4) . ? C2A H2AA 0.9300 . ? C3A C4A 1.393(4) . ? C3A H3AA 0.9300 . ? C4A C5A 1.391(4) . ? C4A C7A 1.503(4) . ? C5A C6A 1.378(4) . ? C5A H5AA 0.9300 . ? C6A H6AA 0.9300 . ? C7A H7AA 0.9599 . ? C7A H7AB 0.9610 . ? C7A H7AC 0.9615 . ? 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 116.9(3) . . ? C2 C1 I1 122.1(2) . . ? C6 C1 I1 121.1(2) . . ? F2 C2 C3 117.6(3) . . ? F2 C2 C1 120.0(2) . . ? C3 C2 C1 122.4(3) . . ? F3 C3 C4 120.4(3) . . ? F3 C3 C2 120.3(3) . . ? C4 C3 C2 119.3(3) . . ? F4 C4 C3 120.3(3) . . ? F4 C4 C5 119.5(3) . . ? C3 C4 C5 120.2(3) . . ? F5 C5 C4 120.0(3) . . ? F5 C5 C6 120.5(3) . . ? C4 C5 C6 119.4(3) . . ? F6 C6 C5 117.9(3) . . ? F6 C6 C1 120.3(3) . . ? C5 C6 C1 121.8(3) . . ? C6A N1A C2A 116.2(3) . . ? N1A C2A C3A 123.9(3) . . ? N1A C2A H2AA 118.1 . . ? C3A C2A H2AA 118.1 . . ? C2A C3A C4A 119.4(3) . . ? C2A C3A H3AA 120.3 . . ? C4A C3A H3AA 120.3 . . ? C5A C4A C3A 116.7(3) . . ? C5A C4A C7A 121.6(3) . . ? C3A C4A C7A 121.7(3) . . ? C6A C5A C4A 119.7(3) . . ? C6A C5A H5AA 120.1 . . ? C4A C5A H5AA 120.1 . . ? N1A C6A C5A 124.1(3) . . ? N1A C6A H6AA 117.9 . . ? C5A C6A H6AA 117.9 . . ? C4A C7A H7AA 109.5 . . ? C4A C7A H7AB 107.3 . . ? H7AA C7A H7AB 109.4 . . ? C4A C7A H7AC 111.7 . . ? H7AA C7A H7AC 109.6 . . ? H7AB C7A H7AC 109.4 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.095 _refine_diff_density_min -0.858 _refine_diff_density_rms 0.091 #===END