# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_section_title ;Mutual induced coordination in halogen-bonded anionic assemblies with (6.3) cation-templated topologies ; _publ_contact_author_name 'Prof. Pierangelo Metrangolo' _publ_contact_author_email PIERANGELO.METRANGOLO@POLIMI.IT loop_ _publ_author_name 'Pierangelo Metrangolo' 'Frank Meyer' 'Tullio Pilati' 'Giuseppe Resnati' 'Giancarlo Terraneo' # Attachment '9.CIF' data_re188 _database_code_depnum_ccdc_archive 'CCDC 665593' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 F3 I3, C3 H9 S 1+, I 1-' _chemical_formula_sum 'C9 H9 F3 I4 S' _chemical_formula_weight 713.82 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 21.052(5) _cell_length_b 7.2160(18) _cell_length_c 11.691(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1775.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 16772 _cell_measurement_theta_min 2.607 _cell_measurement_theta_max 34.415 _exptl_crystal_description 'hexagonal prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1272 _exptl_absorpt_coefficient_mu 7.144 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS,(Bruker, 1997)' _exptl_absorpt_correction_T_min 0.498248 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; Low temperature Bruker KRIOFLEX device. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 26050 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 34.41 _reflns_number_total 3858 _reflns_number_gt 3789 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0204P)^2^+3.5069P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00029(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3858 _refine_ls_number_parameters 143 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.0321 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0658 _refine_ls_wR_factor_gt 0.0653 _refine_ls_goodness_of_fit_ref 1.278 _refine_ls_restrained_S_all 1.272 _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 0.159648(11) 0.2500 -0.06284(2) 0.02506(6) Uani 1 2 d S . . I2 I 0.576434(12) 0.2500 -0.18941(2) 0.02540(6) Uani 1 2 d S . . I3 I 0.317358(12) 0.2500 0.03022(2) 0.02802(7) Uani 1 2 d S . . I4 I 0.556161(13) 0.2500 0.32764(2) 0.02880(7) Uani 1 2 d S . . F1 F 0.42748(12) 0.2500 -0.1498(2) 0.0327(5) Uani 1 2 d S . . F2 F 0.40977(12) 0.2500 0.2500(2) 0.0283(5) Uani 1 2 d S . . F3 F 0.61106(11) 0.2500 0.0772(2) 0.0338(6) Uani 1 2 d S . . C1 C 0.52100(18) 0.2500 -0.0406(3) 0.0241(7) Uani 1 2 d S . . C2 C 0.45502(18) 0.2500 -0.0457(3) 0.0242(6) Uani 1 2 d S . . C3 C 0.41614(17) 0.2500 0.0502(3) 0.0229(6) Uani 1 2 d S . . C4 C 0.44587(18) 0.2500 0.1557(3) 0.0235(6) Uani 1 2 d S . . C5 C 0.51171(19) 0.2500 0.1676(3) 0.0248(7) Uani 1 2 d S . . C6 C 0.54705(18) 0.2500 0.0683(3) 0.0244(7) Uani 1 2 d S . . C7 C 0.2026(3) 0.6199(9) 0.1913(6) 0.0416(15) Uani 0.50 1 d PD A -1 H7A H 0.2471(10) 0.627(6) 0.216(4) 0.062 Uiso 0.50 1 d PD B -1 H7B H 0.196(3) 0.505(2) 0.149(3) 0.062 Uiso 0.50 1 d PD C -1 H7C H 0.175(2) 0.622(6) 0.259(3) 0.062 Uiso 0.50 1 d PD D -1 C8 C 0.10683(19) 0.748(2) 0.0502(4) 0.0352(13) Uani 0.5 1 d SD A -1 H8A H 0.090(2) 0.845(7) 0.000(6) 0.053 Uiso 0.50 1 d PD E -1 H8B H 0.0789(14) 0.732(13) 0.1164(16) 0.053 Uiso 0.50 1 d PD F -1 H8C H 0.1098(15) 0.631(7) 0.008(7) 0.053 Uiso 0.50 1 d PD G -1 C9 C 0.2329(3) 0.748(2) -0.0221(5) 0.0512(18) Uani 0.5 1 d SD A -1 H9A H 0.2774(10) 0.738(17) 0.002(3) 0.077 Uiso 0.50 1 d PD H -1 H9B H 0.229(5) 0.843(9) -0.082(4) 0.077 Uiso 0.50 1 d PD I -1 H9C H 0.218(4) 0.629(8) -0.052(7) 0.077 Uiso 0.50 1 d PD J -1 S1 S 0.18499(7) 0.8162(2) 0.09998(16) 0.0357(3) Uani 0.50 1 d PD A -1 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 0.02287(11) 0.02967(12) 0.02265(11) 0.000 -0.00060(8) 0.000 I2 0.02801(12) 0.02240(11) 0.02581(12) 0.000 0.00496(9) 0.000 I3 0.02075(10) 0.03026(12) 0.03304(14) 0.000 -0.00130(9) 0.000 I4 0.03174(13) 0.03015(13) 0.02450(12) 0.000 -0.00633(9) 0.000 F1 0.0288(12) 0.0452(15) 0.0242(11) 0.000 -0.0053(9) 0.000 F2 0.0283(11) 0.0335(12) 0.0230(11) 0.000 0.0041(9) 0.000 F3 0.0191(10) 0.0474(15) 0.0349(13) 0.000 -0.0011(9) 0.000 C1 0.0236(15) 0.0235(16) 0.0251(16) 0.000 0.0044(13) 0.000 C2 0.0243(15) 0.0266(16) 0.0216(15) 0.000 -0.0023(12) 0.000 C3 0.0198(14) 0.0243(15) 0.0246(16) 0.000 -0.0010(12) 0.000 C4 0.0248(15) 0.0237(15) 0.0219(15) 0.000 0.0015(13) 0.000 C5 0.0269(17) 0.0239(16) 0.0237(16) 0.000 -0.0032(13) 0.000 C6 0.0225(15) 0.0238(16) 0.0270(17) 0.000 -0.0019(13) 0.000 C7 0.037(3) 0.049(4) 0.038(3) -0.010(3) -0.009(3) 0.007(3) C8 0.0236(18) 0.040(3) 0.042(3) 0.018(7) 0.0015(19) 0.005(8) C9 0.038(3) 0.048(4) 0.068(5) 0.026(8) 0.018(3) -0.010(8) S1 0.0275(6) 0.0305(6) 0.0492(9) -0.0141(6) 0.0003(6) -0.0005(5) _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 I2 C1 2.095(4) . ? I3 C3 2.093(4) . ? I4 C5 2.092(4) . ? F1 C2 1.348(4) . ? F2 C4 1.340(4) . ? F3 C6 1.352(4) . ? C1 C6 1.386(6) . ? C1 C2 1.390(5) . ? C2 C3 1.388(5) . ? C3 C4 1.383(5) . ? C4 C5 1.393(5) . ? C5 C6 1.379(6) . ? C7 S1 1.812(6) . ? C7 H7A 0.981(9) . ? C7 H7B 0.980(9) . ? C7 H7C 0.979(9) . ? C8 S1 1.814(6) . ? C8 H8A 0.979(9) . ? C8 H8B 0.979(9) . ? C8 H8C 0.978(9) . ? C9 S1 1.815(6) . ? C9 H9A 0.981(9) . ? C9 H9B 0.980(9) . ? C9 H9C 0.979(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 115.8(3) . . ? C6 C1 I2 122.8(3) . . ? C2 C1 I2 121.4(3) . . ? F1 C2 C3 118.4(3) . . ? F1 C2 C1 117.9(3) . . ? C3 C2 C1 123.7(4) . . ? C4 C3 C2 117.0(3) . . ? C4 C3 I3 123.3(3) . . ? C2 C3 I3 119.7(3) . . ? F2 C4 C3 118.5(3) . . ? F2 C4 C5 118.8(3) . . ? C3 C4 C5 122.7(4) . . ? C6 C5 C4 116.9(4) . . ? C6 C5 I4 120.8(3) . . ? C4 C5 I4 122.3(3) . . ? F3 C6 C5 118.2(3) . . ? F3 C6 C1 117.7(3) . . ? C5 C6 C1 124.1(4) . . ? S1 C7 H7A 109.1(15) . . ? S1 C7 H7B 109.6(16) . . ? H7A C7 H7B 109.4(19) . . ? S1 C7 H7C 109.9(16) . . ? H7A C7 H7C 109.3(19) . . ? H7B C7 H7C 109.6(19) . . ? S1 C8 H8A 108.8(15) . . ? S1 C8 H8B 108.8(15) . . ? H8A C8 H8B 110.0(19) . . ? S1 C8 H8C 109.8(15) . . ? H8A C8 H8C 109.3(19) . . ? H8B C8 H8C 110.1(19) . . ? S1 C9 H9A 109.0(15) . . ? S1 C9 H9B 109.0(16) . . ? H9A C9 H9B 110(2) . . ? S1 C9 H9C 110.0(16) . . ? H9A C9 H9C 110(2) . . ? H9B C9 H9C 109.6(19) . . ? C7 S1 C8 99.3(5) . . ? C7 S1 C9 97.9(5) . . ? C8 S1 C9 100.3(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 C6 C1 C2 F1 180.0 . . . . ? I2 C1 C2 F1 0.0 . . . . ? C6 C1 C2 C3 0.0 . . . . ? I2 C1 C2 C3 180.0 . . . . ? F1 C2 C3 C4 180.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? F1 C2 C3 I3 0.0 . . . . ? C1 C2 C3 I3 180.0 . . . . ? C2 C3 C4 F2 180.0 . . . . ? I3 C3 C4 F2 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? I3 C3 C4 C5 180.0 . . . . ? F2 C4 C5 C6 180.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? F2 C4 C5 I4 0.0 . . . . ? C3 C4 C5 I4 180.0 . . . . ? C4 C5 C6 F3 180.0 . . . . ? I4 C5 C6 F3 0.0 . . . . ? C4 C5 C6 C1 0.0 . . . . ? I4 C5 C6 C1 180.0 . . . . ? C2 C1 C6 F3 180.0 . . . . ? I2 C1 C6 F3 0.0 . . . . ? C2 C1 C6 C5 0.0 . . . . ? I2 C1 C6 C5 180.0 . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 33.40 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.188 _refine_diff_density_min -1.113 _refine_diff_density_rms 0.231 # Attachment '10_revised.CIF' data_re184 _database_code_depnum_ccdc_archive 'CCDC 665594' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H20 N 1+, C6 F3 I3, I 1-' _chemical_formula_sum 'C14 H20 F3 I4 N' _chemical_formula_weight 766.91 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 trigonal _symmetry_space_group_name_H-M R-3c _symmetry_space_group_name_Hall '-R 3 2"c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'y, x, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'y+2/3, x+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' 'y+1/3, x+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-y, -x, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-y+2/3, -x+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' '-y+1/3, -x+2/3, z+1/6' _cell_length_a 20.758(2) _cell_length_b 20.758 _cell_length_c 27.172(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 10139.7(18) _cell_formula_units_Z 18 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5510 _cell_measurement_theta_min 2.717 _cell_measurement_theta_max 28.322 _exptl_crystal_description amigdala _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6300 _exptl_absorpt_coefficient_mu 5.551 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS,(Bruker, 1997)' _exptl_absorpt_correction_T_min 0.487756 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; The crystals are very well formed but translucent or opaque, probably due to a partial leak of unknown crystallization solvent (see _refine_special_details) Crystals were obtained by methanol. OXFORD low temperature device. Attempts to collect data at lower temperature failed probably due to a phase transition. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 30654 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 31.44 _reflns_number_total 3525 _reflns_number_gt 2042 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson,1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The structure contains solvent accessible void of 118 A\%**3, This void is around 2/3,1/3,1/3, between the trifluorotriiodobenzene (tFtIb) molecules having their centroids at 2/3,1/3,0.2194 and 2/3,1/3,0.4473; they are 6.19 A\% far each other. The final Fourier map shows two residues in this void, namely: Q12 1 0.7050 0.2791 0.3327 11.00000 0.05 0.42 Q16 1 0.6667 0.3333 0.3173 10.33333 0.05 0.39 Any attempt to refine this redidues as disordered methanol gave very high ADPs and low population parameters. Attempts were also made to refine possible twinning (obverse+reverse) but always the BASF parameter of SHELXL-97 converged to 0.0 Probably this feature depends only to the unsufficient quality of the crystals, surely worse than the isomorphous compound containing tetraethylphosphonium iodide. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0530P)^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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3525 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0790 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1223 _refine_ls_wR_factor_gt 0.1157 _refine_ls_goodness_of_fit_ref 0.869 _refine_ls_restrained_S_all 0.869 _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 0.6667 0.16423(2) 0.0833 0.06674(19) Uani 1 2 d S . . C1 C 0.6667 0.2653(3) 0.0833 0.067(2) Uani 1 2 d S . . C2 C 0.6014(3) 0.2681(3) 0.0833 0.065(2) Uani 1 2 d S . . F1 F 0.53655(19) 0.20322(19) 0.0833 0.0786(15) Uani 1 2 d S . . I2 I 0.83547(2) 0.33303(2) 0.22406(2) 0.07852(19) Uani 1 1 d . . . C3 C 0.6670(3) 0.2688(3) 0.2196(3) 0.085(2) Uani 1 1 d . . . C4 C 0.7351(3) 0.3345(4) 0.2192(3) 0.084(2) Uani 1 1 d . . . F2 F 0.66647(18) 0.20285(18) 0.22002(18) 0.0978(14) Uani 1 1 d . . . I3 I 1.0000 0.338357(19) 0.2500 0.04988(15) Uani 1 2 d S . . N1 N 0.6237(3) 0.0000 0.2500 0.0478(12) Uani 1 2 d S . . C5 C 0.5930(3) 0.0243(3) 0.20748(19) 0.0591(13) Uani 1 1 d . . . H5A H 0.5918 0.0694 0.2178 0.071 Uiso 1 1 calc R . . H5B H 0.6283 0.0386 0.1796 0.071 Uiso 1 1 calc R . . C6 C 0.5182(3) -0.0309(4) 0.18938(19) 0.0726(16) Uani 1 1 d . . . H6A H 0.5044 -0.0095 0.1620 0.109 Uiso 1 1 calc R . . H6B H 0.4819 -0.0442 0.2161 0.109 Uiso 1 1 calc R . . H6C H 0.5186 -0.0755 0.1781 0.109 Uiso 1 1 calc R . . C7 C 0.6962(3) 0.0643(3) 0.2661(2) 0.0650(15) Uani 1 1 d . . . H7A H 0.7132 0.0497 0.2959 0.078 Uiso 1 1 calc R . . H7B H 0.6882 0.1059 0.2753 0.078 Uiso 1 1 calc R . . C8 C 0.7589(3) 0.0924(3) 0.2266(2) 0.0780(18) Uani 1 1 d . . . H8A H 0.8045 0.1343 0.2399 0.117 Uiso 1 1 calc R . . H8B H 0.7433 0.1085 0.1972 0.117 Uiso 1 1 calc R . . H8C H 0.7682 0.0520 0.2178 0.117 Uiso 1 1 calc 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 0.0512(3) 0.0416(2) 0.1106(5) 0.00278(13) 0.0056(3) 0.02561(14) C1 0.049(4) 0.035(2) 0.120(7) 0.003(2) 0.006(4) 0.0247(19) C2 0.035(2) 0.035(2) 0.114(7) -0.003(2) 0.003(2) 0.011(3) F1 0.0396(16) 0.0396(16) 0.152(5) -0.0023(13) 0.0023(13) 0.0165(19) I2 0.0534(2) 0.0554(2) 0.1296(5) -0.0016(2) 0.0181(2) 0.02935(18) C3 0.056(3) 0.049(3) 0.154(7) -0.005(4) -0.002(4) 0.031(3) C4 0.054(3) 0.067(4) 0.137(7) -0.006(4) 0.013(4) 0.034(3) F2 0.058(2) 0.0502(18) 0.188(5) -0.017(2) -0.003(2) 0.0289(16) I3 0.0539(3) 0.04062(18) 0.0595(3) 0.00984(10) 0.0197(2) 0.02696(13) N1 0.043(2) 0.051(3) 0.052(3) -0.006(3) -0.0031(13) 0.0255(16) C5 0.054(3) 0.081(4) 0.054(3) -0.014(3) -0.011(2) 0.042(3) C6 0.051(3) 0.103(5) 0.069(4) -0.013(3) -0.013(3) 0.042(3) C7 0.044(3) 0.074(4) 0.076(4) -0.025(3) -0.015(2) 0.029(3) C8 0.048(3) 0.069(4) 0.101(5) -0.021(3) 0.002(3) 0.017(3) _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 2.097(7) . ? C1 C2 1.385(4) . ? C1 C2 1.385(4) 2_655 ? C2 F1 1.347(7) . ? C2 C1 1.385(4) 3_665 ? I2 C4 2.102(6) . ? C3 F2 1.363(6) . ? C3 C4 1.366(7) 3_665 ? C3 C4 1.389(7) . ? C4 C3 1.366(7) 2_655 ? N1 C7 1.494(6) . ? N1 C7 1.494(6) 4 ? N1 C5 1.521(6) 4 ? N1 C5 1.521(6) . ? C5 C6 1.480(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.558(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C2 115.8(8) . 2_655 ? C2 C1 I1 122.1(4) . . ? C2 C1 I1 122.1(4) 2_655 . ? F1 C2 C1 117.9(4) . . ? C1 C2 C1 124.2(8) . 3_665 ? F2 C3 C4 116.6(6) . 3_665 ? F2 C3 C4 118.6(6) . . ? C4 C3 C4 124.8(7) 3_665 . ? C3 C4 C3 115.2(7) 2_655 . ? C3 C4 I2 123.6(5) 2_655 . ? C3 C4 I2 121.0(5) . . ? C7 N1 C7 111.7(5) . 4 ? C7 N1 C5 109.1(3) . 4 ? C7 N1 C5 109.2(3) 4 4 ? C7 N1 C5 109.2(3) . . ? C7 N1 C5 109.1(3) 4 . ? C5 N1 C5 108.6(5) 4 . ? C6 C5 N1 116.6(5) . . ? C6 C5 H5A 108.1 . . ? N1 C5 H5A 108.1 . . ? C6 C5 H5B 108.1 . . ? N1 C5 H5B 108.1 . . ? H5A C5 H5B 107.3 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 C8 114.3(5) . . ? N1 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? N1 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C2 F1 180.0 2_655 . . . ? I1 C1 C2 F1 0.0 . . . . ? C2 C1 C2 C1 0.0 2_655 . . 3_665 ? I1 C1 C2 C1 180.0 . . . 3_665 ? F2 C3 C4 C3 -178.9(4) . . . 2_655 ? C4 C3 C4 C3 1.6(18) 3_665 . . 2_655 ? F2 C3 C4 I2 -4.1(11) . . . . ? C4 C3 C4 I2 176.4(5) 3_665 . . . ? C7 N1 C5 C6 -175.1(4) . . . . ? C7 N1 C5 C6 62.5(6) 4 . . . ? C5 N1 C5 C6 -56.4(4) 4 . . . ? C7 N1 C7 C8 56.5(4) 4 . . . ? C5 N1 C7 C8 177.2(5) 4 . . . ? C5 N1 C7 C8 -64.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 31.44 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 2.394 _refine_diff_density_min -0.838 _refine_diff_density_rms 0.165 # Attachment '13_revised.CIF' data_re183lt _database_code_depnum_ccdc_archive 'CCDC 665595' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H20 P 1+, C6 F3 I3, I 1-' _chemical_formula_sum 'C14 H20 F3 I4 P' _chemical_formula_weight 783.87 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 trigonal _symmetry_space_group_name_H-M R-3c _symmetry_space_group_name_Hall '-R 3 2"c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'y, x, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'y+2/3, x+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' 'y+1/3, x+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-y, -x, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-y+2/3, -x+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' '-y+1/3, -x+2/3, z+1/6' _cell_length_a 20.834(3) _cell_length_b 20.834 _cell_length_c 27.606(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 10377(2) _cell_formula_units_Z 18 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 12255 _cell_measurement_theta_min 2.698 _cell_measurement_theta_max 32.293 _exptl_crystal_description tabular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6444 _exptl_absorpt_coefficient_mu 5.491 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS,(Bruker, 1997)' _exptl_absorpt_correction_T_min 0.703834 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; Crystals were obtained by methanol Low temperature Bruker KRIOFLEX device. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 50074 _diffrn_reflns_av_R_equivalents 0.0266 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 32.52 _reflns_number_total 4192 _reflns_number_gt 3556 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The structure contains solvent accessible void of 124 A\%**3. This void is around 2/3,1/3,1/3, between the trifluorotriiodobenzene (tFtIb) molecules having their centroids at 2/3,1/3,0.2173 and 2/3,1/3,0.4494; they are 6.31 A\% far each other. The final Fourier map shows only a very small residue in the middle between the two centroids (0.032 A\%**3). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0304P)^2^+0.0605P] 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 norerf _refine_ls_extinction_method none _refine_ls_number_reflns 4192 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0606 _refine_ls_wR_factor_gt 0.0577 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _refine_ls_shift/su_max 0.003 _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 0.6667 0.164958(9) 0.0833 0.03082(6) Uani 1 2 d S . . C1 C 0.6667 0.26592(14) 0.0833 0.0270(6) Uani 1 2 d S . . C2 C 0.60119(14) 0.26786(14) 0.0833 0.0265(6) Uani 1 2 d S . . F1 F 0.53661(9) 0.20327(9) 0.0833 0.0383(5) Uani 1 2 d S . . I2 I 0.834361(8) 0.332435(8) 0.223011(6) 0.03106(5) Uani 1 1 d . . . C3 C 0.66621(12) 0.26801(12) 0.21727(8) 0.0281(4) Uani 1 1 d . . . C4 C 0.73401(12) 0.33313(12) 0.21730(8) 0.0280(4) Uani 1 1 d . . . F2 F 0.66612(7) 0.20322(7) 0.21863(6) 0.0391(4) Uani 1 1 d . . . I3 I 1.0000 0.340289(9) 0.2500 0.02668(5) Uani 1 2 d S . . P1 P 0.62324(3) 0.0000 0.2500 0.02146(14) Uani 1 2 d S . . C5 C 0.58538(12) 0.02278(13) 0.19912(8) 0.0293(4) Uani 1 1 d . . . H5A H 0.5795 0.0657 0.2077 0.035 Uiso 1 1 calc R . . H5B H 0.6211 0.0381 0.1720 0.035 Uiso 1 1 calc R . . C6 C 0.51115(13) -0.04012(16) 0.18211(9) 0.0413(6) Uani 1 1 d . . . H6A H 0.4937 -0.0235 0.1544 0.062 Uiso 1 1 calc R . . H6B H 0.4751 -0.0552 0.2085 0.062 Uiso 1 1 calc R . . H6C H 0.5167 -0.0823 0.1723 0.062 Uiso 1 1 calc R . . C7 C 0.71208(11) 0.07811(12) 0.26454(8) 0.0291(4) Uani 1 1 d . . . H7A H 0.7057 0.1211 0.2718 0.035 Uiso 1 1 calc R . . H7B H 0.7310 0.0666 0.2942 0.035 Uiso 1 1 calc R . . C8 C 0.77011(13) 0.09995(15) 0.22428(10) 0.0419(6) Uani 1 1 d . . . H8A H 0.8169 0.1428 0.2348 0.063 Uiso 1 1 calc R . . H8B H 0.7525 0.1128 0.1949 0.063 Uiso 1 1 calc R . . H8C H 0.7780 0.0582 0.2174 0.063 Uiso 1 1 calc 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 0.03027(10) 0.02501(7) 0.03895(13) 0.00190(4) 0.00380(8) 0.01514(5) C1 0.0304(15) 0.0244(10) 0.0281(15) 0.0003(6) 0.0006(12) 0.0152(7) C2 0.0226(9) 0.0226(9) 0.0293(15) -0.0005(6) 0.0005(6) 0.0074(11) F1 0.0256(7) 0.0256(7) 0.0588(14) -0.0017(5) 0.0017(5) 0.0091(8) I2 0.02405(7) 0.02707(8) 0.04368(10) 0.00003(6) 0.00572(6) 0.01399(6) C3 0.0291(11) 0.0225(9) 0.0337(12) -0.0026(8) 0.0002(9) 0.0138(8) C4 0.0242(10) 0.0285(10) 0.0319(12) -0.0002(9) 0.0020(8) 0.0136(8) F2 0.0316(7) 0.0229(6) 0.0642(11) -0.0080(6) -0.0012(7) 0.0147(6) I3 0.02347(9) 0.02255(7) 0.03432(11) 0.00386(4) 0.00772(7) 0.01173(5) P1 0.0199(2) 0.0228(3) 0.0227(3) -0.0065(3) -0.00323(13) 0.01142(17) C5 0.0330(11) 0.0345(11) 0.0259(11) -0.0032(9) -0.0028(9) 0.0210(10) C6 0.0290(11) 0.0619(17) 0.0332(13) -0.0029(12) -0.0081(10) 0.0228(12) C7 0.0212(9) 0.0283(10) 0.0342(12) -0.0100(9) -0.0041(8) 0.0096(8) C8 0.0271(11) 0.0417(14) 0.0463(15) -0.0078(11) 0.0034(10) 0.0093(11) _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 2.103(3) . ? C1 C2 1.3847(19) 2_655 ? C1 C2 1.3847(19) . ? C2 F1 1.346(3) . ? C2 C1 1.3847(19) 3_665 ? I2 C4 2.104(2) . ? C3 F2 1.349(2) . ? C3 C4 1.377(3) 3_665 ? C3 C4 1.385(3) . ? C4 C3 1.377(3) 2_655 ? P1 C5 1.787(2) . ? P1 C5 1.787(2) 4 ? P1 C7 1.795(2) 4 ? P1 C7 1.795(2) . ? C5 C6 1.517(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.534(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C2 117.1(3) 2_655 . ? C2 C1 I1 121.45(16) 2_655 . ? C2 C1 I1 121.45(16) . . ? F1 C2 C1 118.55(16) . 3_665 ? F1 C2 C1 118.55(16) . . ? C1 C2 C1 122.9(3) 3_665 . ? F2 C3 C4 118.4(2) . 3_665 ? F2 C3 C4 118.1(2) . . ? C4 C3 C4 123.5(2) 3_665 . ? C3 C4 C3 116.5(2) 2_655 . ? C3 C4 I2 121.76(17) 2_655 . ? C3 C4 I2 121.56(17) . . ? C5 P1 C5 109.93(15) . 4 ? C5 P1 C7 109.66(10) . 4 ? C5 P1 C7 109.07(11) 4 4 ? C5 P1 C7 109.07(11) . . ? C5 P1 C7 109.66(10) 4 . ? C7 P1 C7 109.42(14) 4 . ? C6 C5 P1 114.10(17) . . ? C6 C5 H5A 108.7 . . ? P1 C5 H5A 108.7 . . ? C6 C5 H5B 108.7 . . ? P1 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 P1 114.16(16) . . ? C8 C7 H7A 108.7 . . ? P1 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? P1 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C2 F1 180.0 2_655 . . . ? I1 C1 C2 F1 0.0 . . . . ? C2 C1 C2 C1 0.0 2_655 . . 3_665 ? I1 C1 C2 C1 180.0 . . . 3_665 ? F2 C3 C4 C3 -178.23(12) . . . 2_655 ? C4 C3 C4 C3 -0.1(5) 3_665 . . 2_655 ? F2 C3 C4 I2 -3.2(3) . . . . ? C4 C3 C4 I2 174.92(12) 3_665 . . . ? C5 P1 C5 C6 -61.83(16) 4 . . . ? C7 P1 C5 C6 58.1(2) 4 . . . ? C7 P1 C5 C6 177.90(17) . . . . ? C5 P1 C7 C8 -62.8(2) . . . . ? C5 P1 C7 C8 176.81(18) 4 . . . ? C7 P1 C7 C8 57.21(16) 4 . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 32.52 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.313 _refine_diff_density_min -0.991 _refine_diff_density_rms 0.112 # Attachment '11.CIF' data_re187lt _database_code_depnum_ccdc_archive 'CCDC 665596' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H28 N 1+, I 1-, C6 F3 I3, C H2 Cl2' _chemical_formula_sum 'C19 H30 Cl2 F3 I4 N' _chemical_formula_weight 907.94 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' Cl Cl 0.1484 0.1585 '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' _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 11.0985(12) _cell_length_b 20.323(2) _cell_length_c 12.4108(15) _cell_angle_alpha 90.00 _cell_angle_beta 91.49(2) _cell_angle_gamma 90.00 _cell_volume 2798.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 26018 _cell_measurement_theta_min 2.431 _cell_measurement_theta_max 34.371 _exptl_crystal_description 'Irregular prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.155 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 4.672 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS,(Bruker, 1997)' _exptl_absorpt_correction_T_min 0.769755 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; Low temperature Bruker KRIOFLEX device. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 55107 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 34.47 _reflns_number_total 11375 _reflns_number_gt 10788 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution ;M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0272P)^2^+4.6444P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_number_reflns 11375 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0326 _refine_ls_wR_factor_ref 0.0720 _refine_ls_wR_factor_gt 0.0707 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _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 0.726086(16) 0.144363(8) 0.522326(13) 0.02158(4) Uani 1 1 d . . . I2 I 0.817562(15) 0.309280(8) 0.485310(13) 0.01950(4) Uani 1 1 d . . . I3 I 0.813199(15) 0.566457(7) 0.233638(12) 0.01894(4) Uani 1 1 d . . . I4 I 0.852812(16) 0.566431(8) 0.725146(13) 0.02130(4) Uani 1 1 d . . . F1 F 0.81013(16) 0.41404(8) 0.29177(12) 0.0235(3) Uani 1 1 d . . . F2 F 0.85489(15) 0.61447(7) 0.47732(12) 0.0220(3) Uani 1 1 d . . . F3 F 0.84978(17) 0.41524(8) 0.66874(12) 0.0260(3) Uani 1 1 d . . . C1 C 0.8341(2) 0.41220(12) 0.47974(19) 0.0174(4) Uani 1 1 d . . . C2 C 0.8256(2) 0.44753(12) 0.38430(19) 0.0173(4) Uani 1 1 d . . . C3 C 0.8321(2) 0.51576(12) 0.38061(18) 0.0169(4) Uani 1 1 d . . . C4 C 0.8467(2) 0.54815(12) 0.47824(19) 0.0168(4) Uani 1 1 d . . . C5 C 0.8514(2) 0.51639(12) 0.57710(18) 0.0175(4) Uani 1 1 d . . . C6 C 0.8455(2) 0.44815(12) 0.57466(19) 0.0184(4) Uani 1 1 d . . . N1 N 0.37013(19) 0.23755(10) 0.37567(16) 0.0179(4) Uani 1 1 d . . . C7 C 0.3742(2) 0.18389(13) 0.46181(19) 0.0204(4) Uani 1 1 d . . . H7A H 0.4502 0.1887 0.5045 0.025 Uiso 1 1 calc R . . H7B H 0.3070 0.1915 0.5112 0.025 Uiso 1 1 calc R . . C8 C 0.3660(3) 0.11356(14) 0.4213(2) 0.0243(5) Uani 1 1 d . . . H8A H 0.4365 0.1034 0.3769 0.029 Uiso 1 1 calc R . . H8B H 0.2921 0.1079 0.3759 0.029 Uiso 1 1 calc R . . C9 C 0.3632(3) 0.06719(16) 0.5173(3) 0.0329(6) Uani 1 1 d . . . H9A H 0.3580 0.0216 0.4917 0.049 Uiso 1 1 calc R . . H9B H 0.2929 0.0772 0.5606 0.049 Uiso 1 1 calc R . . H9C H 0.4369 0.0728 0.5616 0.049 Uiso 1 1 calc R . . C10 C 0.3668(2) 0.30389(13) 0.4318(2) 0.0211(4) Uani 1 1 d . . . H10A H 0.3434 0.3377 0.3779 0.025 Uiso 1 1 calc R . . H10B H 0.3031 0.3026 0.4862 0.025 Uiso 1 1 calc R . . C11 C 0.4835(3) 0.32516(14) 0.4874(2) 0.0243(5) Uani 1 1 d . . . H11A H 0.5459 0.3323 0.4330 0.029 Uiso 1 1 calc R . . H11B H 0.5122 0.2901 0.5372 0.029 Uiso 1 1 calc R . . C12 C 0.4640(3) 0.38839(16) 0.5499(3) 0.0309(6) Uani 1 1 d . . . H12A H 0.5399 0.4018 0.5856 0.046 Uiso 1 1 calc R . . H12B H 0.4029 0.3811 0.6043 0.046 Uiso 1 1 calc R . . H12C H 0.4366 0.4231 0.5003 0.046 Uiso 1 1 calc R . . C13 C 0.2577(2) 0.23130(13) 0.30290(19) 0.0214(4) Uani 1 1 d . . . H13A H 0.2571 0.2682 0.2509 0.026 Uiso 1 1 calc R . . H13B H 0.2639 0.1900 0.2610 0.026 Uiso 1 1 calc R . . C14 C 0.1383(2) 0.23104(15) 0.3598(2) 0.0252(5) Uani 1 1 d . . . H14A H 0.1289 0.2723 0.4010 0.030 Uiso 1 1 calc R . . H14B H 0.1354 0.1936 0.4107 0.030 Uiso 1 1 calc R . . C15 C 0.0373(3) 0.2248(2) 0.2744(3) 0.0363(7) Uani 1 1 d . . . H15A H -0.0408 0.2246 0.3095 0.054 Uiso 1 1 calc R . . H15B H 0.0472 0.1837 0.2343 0.054 Uiso 1 1 calc R . . H15C H 0.0407 0.2622 0.2247 0.054 Uiso 1 1 calc R . . C16 C 0.4805(2) 0.23065(12) 0.30690(19) 0.0196(4) Uani 1 1 d . . . H16A H 0.4751 0.1882 0.2678 0.023 Uiso 1 1 calc R . . H16B H 0.5528 0.2287 0.3552 0.023 Uiso 1 1 calc R . . C17 C 0.4982(3) 0.28530(13) 0.2252(2) 0.0231(5) Uani 1 1 d . . . H17A H 0.4313 0.2847 0.1709 0.028 Uiso 1 1 calc R . . H17B H 0.4979 0.3285 0.2620 0.028 Uiso 1 1 calc R . . C18 C 0.6170(3) 0.27571(18) 0.1699(3) 0.0348(7) Uani 1 1 d . . . H18A H 0.6281 0.3110 0.1173 0.052 Uiso 1 1 calc R . . H18B H 0.6167 0.2331 0.1329 0.052 Uiso 1 1 calc R . . H18C H 0.6831 0.2768 0.2238 0.052 Uiso 1 1 calc R . . Cl1 Cl 0.51091(10) 0.46523(5) 0.29832(8) 0.0455(2) Uani 1 1 d . . . Cl2 Cl 0.45167(13) 0.55427(6) 0.12210(11) 0.0631(3) Uani 1 1 d . . . C19 C 0.4964(4) 0.4744(2) 0.1572(3) 0.0439(8) Uani 1 1 d . . . H19A H 0.5746 0.4645 0.1241 0.081(19) Uiso 1 1 calc R . . H19B H 0.4362 0.4426 0.1285 0.078(18) Uiso 1 1 calc 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 0.03003(8) 0.01741(7) 0.01709(7) 0.00007(5) -0.00374(5) -0.00213(5) I2 0.02316(7) 0.01529(6) 0.02000(7) 0.00081(5) -0.00070(5) 0.00003(5) I3 0.02437(7) 0.01777(7) 0.01476(6) 0.00200(5) 0.00204(5) -0.00099(5) I4 0.02770(8) 0.02058(7) 0.01539(7) -0.00263(5) -0.00373(5) 0.00379(5) F1 0.0364(9) 0.0198(7) 0.0144(6) -0.0026(5) -0.0004(6) -0.0019(6) F2 0.0308(8) 0.0135(6) 0.0216(7) -0.0007(5) 0.0005(6) -0.0007(5) F3 0.0411(9) 0.0219(7) 0.0149(6) 0.0044(5) -0.0027(6) 0.0010(6) C1 0.0199(10) 0.0146(9) 0.0175(10) 0.0009(7) -0.0001(8) -0.0011(7) C2 0.0203(10) 0.0173(9) 0.0142(9) -0.0013(7) 0.0000(7) -0.0003(8) C3 0.0190(10) 0.0175(9) 0.0142(9) 0.0020(7) 0.0018(7) -0.0003(7) C4 0.0167(9) 0.0154(9) 0.0184(10) -0.0005(7) 0.0009(7) 0.0017(7) C5 0.0198(10) 0.0179(10) 0.0148(9) -0.0011(7) -0.0009(7) 0.0015(8) C6 0.0210(10) 0.0184(10) 0.0159(9) 0.0015(8) 0.0003(8) 0.0008(8) N1 0.0198(9) 0.0208(9) 0.0132(8) -0.0008(7) 0.0009(7) 0.0051(7) C7 0.0242(11) 0.0247(11) 0.0125(9) 0.0010(8) 0.0024(8) 0.0045(9) C8 0.0304(13) 0.0244(12) 0.0181(10) 0.0041(9) 0.0030(9) 0.0021(10) C9 0.0430(17) 0.0306(14) 0.0251(13) 0.0087(11) 0.0012(12) -0.0031(12) C10 0.0234(11) 0.0230(11) 0.0170(10) -0.0036(8) -0.0001(8) 0.0058(9) C11 0.0248(12) 0.0271(12) 0.0208(11) -0.0058(9) -0.0034(9) 0.0041(9) C12 0.0326(14) 0.0306(14) 0.0293(14) -0.0091(11) -0.0044(11) 0.0023(11) C13 0.0232(11) 0.0264(11) 0.0143(9) -0.0010(8) -0.0029(8) 0.0031(9) C14 0.0210(11) 0.0328(13) 0.0217(11) -0.0068(10) 0.0011(9) 0.0030(10) C15 0.0254(13) 0.053(2) 0.0300(14) -0.0135(14) -0.0061(11) 0.0035(13) C16 0.0217(11) 0.0215(10) 0.0157(9) 0.0011(8) 0.0046(8) 0.0061(8) C17 0.0302(13) 0.0219(11) 0.0175(10) 0.0017(8) 0.0032(9) 0.0013(9) C18 0.0357(16) 0.0429(17) 0.0264(13) 0.0016(12) 0.0116(12) -0.0019(13) Cl1 0.0573(5) 0.0357(4) 0.0435(5) -0.0019(3) -0.0018(4) -0.0093(4) Cl2 0.0756(8) 0.0515(6) 0.0616(7) 0.0079(5) -0.0073(6) 0.0171(6) C19 0.053(2) 0.0387(18) 0.0404(18) -0.0040(15) -0.0042(16) 0.0019(16) _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 I2 C1 2.101(2) . ? I3 C3 2.101(2) . ? I4 C5 2.100(2) . ? F1 C2 1.342(3) . ? F2 C4 1.351(3) . ? F3 C6 1.345(3) . ? C1 C2 1.386(3) . ? C1 C6 1.389(3) . ? C2 C3 1.389(3) . ? C3 C4 1.385(3) . ? C4 C5 1.386(3) . ? C5 C6 1.389(3) . ? N1 C16 1.518(3) . ? N1 C10 1.519(3) . ? N1 C13 1.526(3) . ? N1 C7 1.527(3) . ? C7 C8 1.517(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.520(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.514(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.520(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.518(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.528(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.520(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.514(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? Cl1 C19 1.765(4) . ? Cl2 C19 1.749(4) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? 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 117.1(2) . . ? C2 C1 I2 122.66(17) . . ? C6 C1 I2 120.12(17) . . ? F1 C2 C1 118.2(2) . . ? F1 C2 C3 118.9(2) . . ? C1 C2 C3 122.9(2) . . ? C4 C3 C2 116.8(2) . . ? C4 C3 I3 122.23(17) . . ? C2 C3 I3 120.94(17) . . ? F2 C4 C3 118.3(2) . . ? F2 C4 C5 118.1(2) . . ? C3 C4 C5 123.6(2) . . ? C4 C5 C6 116.4(2) . . ? C4 C5 I4 123.25(17) . . ? C6 C5 I4 120.13(17) . . ? F3 C6 C5 118.5(2) . . ? F3 C6 C1 118.3(2) . . ? C5 C6 C1 123.2(2) . . ? C16 N1 C10 111.7(2) . . ? C16 N1 C13 108.59(18) . . ? C10 N1 C13 108.45(19) . . ? C16 N1 C7 108.56(18) . . ? C10 N1 C7 108.25(18) . . ? C13 N1 C7 111.3(2) . . ? C8 C7 N1 116.1(2) . . ? C8 C7 H7A 108.2 . . ? N1 C7 H7A 108.2 . . ? C8 C7 H7B 108.2 . . ? N1 C7 H7B 108.2 . . ? H7A C7 H7B 107.4 . . ? C7 C8 C9 109.1(2) . . ? C7 C8 H8A 109.9 . . ? C9 C8 H8A 109.9 . . ? C7 C8 H8B 109.9 . . ? C9 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 N1 115.6(2) . . ? C11 C10 H10A 108.4 . . ? N1 C10 H10A 108.4 . . ? C11 C10 H10B 108.4 . . ? N1 C10 H10B 108.4 . . ? H10A C10 H10B 107.4 . . ? C10 C11 C12 110.0(2) . . ? C10 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? C10 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 N1 115.8(2) . . ? C14 C13 H13A 108.3 . . ? N1 C13 H13A 108.3 . . ? C14 C13 H13B 108.3 . . ? N1 C13 H13B 108.3 . . ? H13A C13 H13B 107.4 . . ? C13 C14 C15 108.2(2) . . ? C13 C14 H14A 110.1 . . ? C15 C14 H14A 110.1 . . ? C13 C14 H14B 110.1 . . ? C15 C14 H14B 110.1 . . ? H14A C14 H14B 108.4 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 C17 115.3(2) . . ? N1 C16 H16A 108.4 . . ? C17 C16 H16A 108.4 . . ? N1 C16 H16B 108.4 . . ? C17 C16 H16B 108.4 . . ? H16A C16 H16B 107.5 . . ? C18 C17 C16 109.7(2) . . ? C18 C17 H17A 109.7 . . ? C16 C17 H17A 109.7 . . ? C18 C17 H17B 109.7 . . ? C16 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? Cl2 C19 Cl1 111.3(2) . . ? Cl2 C19 H19A 109.4 . . ? Cl1 C19 H19A 109.4 . . ? Cl2 C19 H19B 109.4 . . ? Cl1 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? 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 F1 -177.6(2) . . . . ? I2 C1 C2 F1 -2.2(3) . . . . ? C6 C1 C2 C3 2.2(4) . . . . ? I2 C1 C2 C3 177.60(18) . . . . ? F1 C2 C3 C4 179.3(2) . . . . ? C1 C2 C3 C4 -0.5(4) . . . . ? F1 C2 C3 I3 1.7(3) . . . . ? C1 C2 C3 I3 -178.08(18) . . . . ? C2 C3 C4 F2 179.2(2) . . . . ? I3 C3 C4 F2 -3.3(3) . . . . ? C2 C3 C4 C5 -2.0(4) . . . . ? I3 C3 C4 C5 175.55(18) . . . . ? F2 C4 C5 C6 -178.6(2) . . . . ? C3 C4 C5 C6 2.6(4) . . . . ? F2 C4 C5 I4 6.4(3) . . . . ? C3 C4 C5 I4 -172.44(18) . . . . ? C4 C5 C6 F3 180.0(2) . . . . ? I4 C5 C6 F3 -4.9(3) . . . . ? C4 C5 C6 C1 -0.7(4) . . . . ? I4 C5 C6 C1 174.43(19) . . . . ? C2 C1 C6 F3 177.8(2) . . . . ? I2 C1 C6 F3 2.2(3) . . . . ? C2 C1 C6 C5 -1.5(4) . . . . ? I2 C1 C6 C5 -177.07(19) . . . . ? C16 N1 C7 C8 -64.1(3) . . . . ? C10 N1 C7 C8 174.5(2) . . . . ? C13 N1 C7 C8 55.4(3) . . . . ? N1 C7 C8 C9 -176.4(2) . . . . ? C16 N1 C10 C11 -47.1(3) . . . . ? C13 N1 C10 C11 -166.7(2) . . . . ? C7 N1 C10 C11 72.4(3) . . . . ? N1 C10 C11 C12 -174.0(2) . . . . ? C16 N1 C13 C14 174.9(2) . . . . ? C10 N1 C13 C14 -63.6(3) . . . . ? C7 N1 C13 C14 55.4(3) . . . . ? N1 C13 C14 C15 179.7(2) . . . . ? C10 N1 C16 C17 -53.8(3) . . . . ? C13 N1 C16 C17 65.7(3) . . . . ? C7 N1 C16 C17 -173.1(2) . . . . ? N1 C16 C17 C18 174.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 32.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.265 _refine_diff_density_min -1.353 _refine_diff_density_rms 0.150 # Attachment '12.CIF' data_re181lt _database_code_depnum_ccdc_archive 'CCDC 665597' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C16 H36 N 1+), 2(C6 F3 I3), C H2 Cl2, 2(I 1-)' _chemical_formula_sum 'C45 H74 Cl2 F6 I8 N2' _chemical_formula_weight 1843.16 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' Cl Cl 0.1484 0.1585 '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' _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 11.983(3) _cell_length_b 16.974(4) _cell_length_c 16.379(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.03(3) _cell_angle_gamma 90.00 _cell_volume 3149.4(13) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 9895 _cell_measurement_theta_min 2.162 _cell_measurement_theta_max 31.718 _exptl_crystal_description 'elongated prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.944 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1740 _exptl_absorpt_coefficient_mu 4.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_absorpt_correction_T_min 0.541207 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; Low temperature Bruker KRIOFLEX device. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 29255 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 31.82 _reflns_number_total 10518 _reflns_number_gt 9029 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0530P)^2^+3.3945P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10518 _refine_ls_number_parameters 288 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0478 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0930 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.004 _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 N1 N 0.3105(3) 0.10966(18) 0.3427(2) 0.0279(6) Uani 1 1 d . . . C1 C 0.4253(3) 0.1460(2) 0.3414(3) 0.0341(8) Uani 1 1 d . . . H1A H 0.4625 0.1718 0.3964 0.041 Uiso 1 1 calc R . . H1B H 0.4774 0.1040 0.3362 0.041 Uiso 1 1 calc R . . C2 C 0.4148(4) 0.2046(3) 0.2707(3) 0.0431(10) Uani 1 1 d . . . H2A H 0.3839 0.2538 0.2846 0.052 Uiso 1 1 calc R . . H2B H 0.3598 0.1850 0.2171 0.052 Uiso 1 1 calc R . . C3 C 0.5334(5) 0.2195(4) 0.2590(3) 0.0554(13) Uani 1 1 d . . . H3A H 0.5893 0.2359 0.3138 0.066 Uiso 1 1 calc R . . H3B H 0.5620 0.1707 0.2424 0.066 Uiso 1 1 calc R . . C4 C 0.5286(7) 0.2818(5) 0.1917(4) 0.081(2) Uani 1 1 d . . . H4A H 0.4820 0.2628 0.1357 0.121 Uiso 1 1 calc R . . H4B H 0.6071 0.2930 0.1918 0.121 Uiso 1 1 calc R . . H4C H 0.4936 0.3289 0.2048 0.121 Uiso 1 1 calc R . . C5 C 0.2254(3) 0.1720(2) 0.3540(3) 0.0300(7) Uani 1 1 d . . . H5A H 0.2108 0.2093 0.3068 0.036 Uiso 1 1 calc R . . H5B H 0.1510 0.1464 0.3486 0.036 Uiso 1 1 calc R . . C6 C 0.2641(4) 0.2175(3) 0.4377(3) 0.0395(9) Uani 1 1 d . . . H6A H 0.3312 0.2506 0.4402 0.047 Uiso 1 1 calc R . . H6B H 0.2877 0.1814 0.4861 0.047 Uiso 1 1 calc R . . C7 C 0.1613(4) 0.2687(3) 0.4427(3) 0.0464(11) Uani 1 1 d . . . H7A H 0.1907 0.3074 0.4882 0.056 Uiso 1 1 calc R . . H7B H 0.1280 0.2968 0.3886 0.056 Uiso 1 1 calc R . . C8 C 0.0663(5) 0.2208(4) 0.4601(4) 0.0676(17) Uani 1 1 d . . . H8A H 0.0315 0.1860 0.4124 0.101 Uiso 1 1 calc R . . H8B H 0.0067 0.2554 0.4673 0.101 Uiso 1 1 calc R . . H8C H 0.0998 0.1905 0.5118 0.101 Uiso 1 1 calc R . . C9 C 0.2488(3) 0.0689(2) 0.2572(2) 0.0309(8) Uani 1 1 d . . . H9A H 0.1826 0.0393 0.2629 0.037 Uiso 1 1 calc R . . H9B H 0.2171 0.1091 0.2136 0.037 Uiso 1 1 calc R . . C10 C 0.3238(4) 0.0140(2) 0.2251(3) 0.0354(8) Uani 1 1 d . . . H10A H 0.3621 -0.0238 0.2698 0.042 Uiso 1 1 calc R . . H10B H 0.3847 0.0438 0.2116 0.042 Uiso 1 1 calc R . . C11 C 0.2478(5) -0.0293(3) 0.1446(3) 0.0520(13) Uani 1 1 d . . . H11A H 0.1996 0.0089 0.1043 0.062 Uiso 1 1 calc R . . H11B H 0.2991 -0.0543 0.1171 0.062 Uiso 1 1 calc R . . C12 C 0.1700(5) -0.0897(3) 0.1619(4) 0.0642(16) Uani 1 1 d . . . H12A H 0.2168 -0.1273 0.2026 0.096 Uiso 1 1 calc R . . H12B H 0.1275 -0.1161 0.1091 0.096 Uiso 1 1 calc R . . H12C H 0.1151 -0.0651 0.1855 0.096 Uiso 1 1 calc R . . C13 C 0.3416(3) 0.0501(2) 0.4167(2) 0.0307(7) Uani 1 1 d . . . H13A H 0.3932 0.0106 0.4055 0.037 Uiso 1 1 calc R . . H13B H 0.3860 0.0773 0.4694 0.037 Uiso 1 1 calc R . . C14 C 0.2393(4) 0.0083(3) 0.4325(3) 0.0409(9) Uani 1 1 d . . . H14A H 0.1983 -0.0236 0.3827 0.049 Uiso 1 1 calc R . . H14B H 0.1841 0.0469 0.4407 0.049 Uiso 1 1 calc R . . C15 C 0.2837(5) -0.0444(3) 0.5131(3) 0.0431(10) Uani 1 1 d . . . H15A H 0.3417 -0.0810 0.5055 0.052 Uiso 1 1 calc R . . H15B H 0.3226 -0.0118 0.5629 0.052 Uiso 1 1 calc R . . C16 C 0.1878(7) -0.0896(4) 0.5303(4) 0.0705(18) Uani 1 1 d . . . H16A H 0.1281 -0.0539 0.5351 0.106 Uiso 1 1 calc R . . H16B H 0.2195 -0.1184 0.5834 0.106 Uiso 1 1 calc R . . H16C H 0.1538 -0.1258 0.4838 0.106 Uiso 1 1 calc R . . I1 I 0.08963(2) -0.142429(14) 0.839083(15) 0.02891(6) Uani 1 1 d . . . I2 I 0.14629(2) 0.181184(13) 1.002378(14) 0.02498(6) Uani 1 1 d . . . I3 I 0.38230(2) 0.111135(14) 0.735421(15) 0.02757(6) Uani 1 1 d . . . F1 F 0.06912(19) 0.00265(13) 0.95076(13) 0.0285(4) Uani 1 1 d . . . F2 F 0.2522(2) -0.05302(13) 0.74422(15) 0.0333(5) Uani 1 1 d . . . F3 F 0.2968(2) 0.19625(13) 0.87518(15) 0.0318(5) Uani 1 1 d . . . C17 C 0.1825(3) 0.1018(2) 0.9156(2) 0.0232(6) Uani 1 1 d . . . C18 C 0.1373(3) 0.0259(2) 0.9044(2) 0.0221(6) Uani 1 1 d . . . C19 C 0.1588(3) -0.0279(2) 0.8475(2) 0.0236(6) Uani 1 1 d . . . C20 C 0.2287(3) -0.0023(2) 0.7998(2) 0.0242(6) Uani 1 1 d . . . C21 C 0.2759(3) 0.0727(2) 0.8075(2) 0.0233(6) Uani 1 1 d . . . C22 C 0.2517(3) 0.1232(2) 0.8661(2) 0.0235(6) Uani 1 1 d . . . I4 I 0.57011(2) 0.183873(13) 0.632132(14) 0.02458(6) Uani 1 1 d . . . Cl1 Cl -0.00290(19) 0.42989(12) 0.55363(14) 0.0993(7) Uani 1 1 d D . . C23 C 0.0424(10) 0.4745(5) 0.4836(6) 0.051(2) Uiso 0.50 1 d PD . -1 H23A H 0.0207 0.4411 0.4328 0.061 Uiso 0.50 1 calc PR . -1 H23B H 0.1279 0.4739 0.5066 0.061 Uiso 0.50 1 calc PR . -1 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 N1 0.0278(14) 0.0228(14) 0.0278(14) 0.0020(11) 0.0019(12) 0.0042(11) C1 0.0272(17) 0.033(2) 0.040(2) -0.0034(16) 0.0078(15) 0.0011(14) C2 0.040(2) 0.031(2) 0.058(3) 0.0041(19) 0.015(2) -0.0032(17) C3 0.053(3) 0.074(4) 0.040(2) -0.009(2) 0.017(2) -0.023(3) C4 0.091(5) 0.102(5) 0.051(3) -0.006(3) 0.025(3) -0.054(4) C5 0.0234(16) 0.0271(18) 0.0349(19) -0.0005(14) 0.0030(14) 0.0087(13) C6 0.033(2) 0.036(2) 0.042(2) -0.0101(17) 0.0019(17) 0.0078(16) C7 0.037(2) 0.048(3) 0.046(2) -0.011(2) 0.0025(19) 0.0131(19) C8 0.059(3) 0.087(5) 0.066(4) 0.000(3) 0.032(3) 0.031(3) C9 0.0329(18) 0.0248(17) 0.0278(17) 0.0017(13) 0.0001(14) -0.0003(14) C10 0.046(2) 0.0280(19) 0.0306(18) -0.0020(15) 0.0101(17) -0.0002(16) C11 0.076(4) 0.033(2) 0.034(2) -0.0018(18) 0.001(2) 0.009(2) C12 0.055(3) 0.044(3) 0.068(4) -0.008(3) -0.015(3) 0.000(2) C13 0.0338(19) 0.0261(18) 0.0279(17) 0.0030(13) 0.0041(14) 0.0053(14) C14 0.043(2) 0.037(2) 0.037(2) 0.0085(17) 0.0065(18) -0.0008(17) C15 0.066(3) 0.032(2) 0.031(2) 0.0006(16) 0.015(2) 0.011(2) C16 0.100(5) 0.062(4) 0.051(3) 0.014(3) 0.027(3) -0.018(3) I1 0.02873(11) 0.02334(12) 0.03159(12) -0.00144(8) 0.00561(9) -0.00337(8) I2 0.02894(11) 0.02538(11) 0.02284(10) -0.00265(8) 0.01150(8) 0.00212(8) I3 0.02751(11) 0.03025(12) 0.03072(12) 0.00092(9) 0.01740(9) 0.00088(8) F1 0.0318(11) 0.0317(11) 0.0276(10) 0.0011(8) 0.0174(9) -0.0048(8) F2 0.0405(12) 0.0294(11) 0.0366(12) -0.0097(9) 0.0217(10) -0.0010(9) F3 0.0348(12) 0.0227(10) 0.0445(13) -0.0047(9) 0.0222(10) -0.0064(8) C17 0.0216(14) 0.0249(16) 0.0234(15) -0.0018(12) 0.0077(12) 0.0024(12) C18 0.0205(14) 0.0253(16) 0.0222(14) 0.0006(12) 0.0093(12) 0.0002(11) C19 0.0197(14) 0.0232(16) 0.0270(16) -0.0010(12) 0.0063(12) 0.0000(11) C20 0.0237(15) 0.0267(16) 0.0233(15) -0.0029(12) 0.0093(12) 0.0021(12) C21 0.0218(14) 0.0259(16) 0.0252(15) -0.0001(12) 0.0117(12) 0.0000(12) C22 0.0231(15) 0.0215(15) 0.0272(16) -0.0021(12) 0.0102(13) 0.0002(11) I4 0.02831(11) 0.02266(11) 0.02568(11) 0.00612(7) 0.01278(9) 0.00271(7) Cl1 0.0861(13) 0.0777(12) 0.0986(14) -0.0149(10) -0.0184(11) -0.0095(10) _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 N1 C1 1.514(5) . ? N1 C9 1.521(5) . ? N1 C5 1.522(5) . ? N1 C13 1.529(5) . ? C1 C2 1.500(6) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.515(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.515(9) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C6 1.510(6) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.531(6) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.501(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.503(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.525(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.475(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.509(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.539(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.483(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? I1 C19 2.100(3) . ? I2 C17 2.103(3) . ? I3 C21 2.104(3) . ? F1 C18 1.343(4) . ? F2 C20 1.348(4) . ? F3 C22 1.342(4) . ? C17 C22 1.384(5) . ? C17 C18 1.387(5) . ? C18 C19 1.388(5) . ? C19 C20 1.388(5) . ? C20 C21 1.382(5) . ? C21 C22 1.387(5) . ? Cl1 C23 1.610(9) . ? Cl1 C23 1.743(9) 3_566 ? C23 Cl1 1.743(9) 3_566 ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? 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 C1 N1 C9 110.1(3) . . ? C1 N1 C5 111.5(3) . . ? C9 N1 C5 106.5(3) . . ? C1 N1 C13 107.1(3) . . ? C9 N1 C13 110.4(3) . . ? C5 N1 C13 111.3(3) . . ? C2 C1 N1 115.7(3) . . ? C2 C1 H1A 108.4 . . ? N1 C1 H1A 108.4 . . ? C2 C1 H1B 108.4 . . ? N1 C1 H1B 108.4 . . ? H1A C1 H1B 107.4 . . ? C1 C2 C3 111.2(4) . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C4 C3 C2 113.2(5) . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3B 108.9 . . ? C2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 N1 116.5(3) . . ? C6 C5 H5A 108.2 . . ? N1 C5 H5A 108.2 . . ? C6 C5 H5B 108.2 . . ? N1 C5 H5B 108.2 . . ? H5A C5 H5B 107.3 . . ? C5 C6 C7 109.0(3) . . ? C5 C6 H6A 109.9 . . ? C7 C6 H6A 109.9 . . ? C5 C6 H6B 109.9 . . ? C7 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? C8 C7 C6 112.1(4) . . ? C8 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? C8 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 N1 115.9(3) . . ? C10 C9 H9A 108.3 . . ? N1 C9 H9A 108.3 . . ? C10 C9 H9B 108.3 . . ? N1 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C9 C10 C11 110.2(4) . . ? C9 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 113.9(4) . . ? C12 C11 H11A 108.8 . . ? C10 C11 H11A 108.8 . . ? C12 C11 H11B 108.8 . . ? C10 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 N1 116.5(3) . . ? C14 C13 H13A 108.2 . . ? N1 C13 H13A 108.2 . . ? C14 C13 H13B 108.2 . . ? N1 C13 H13B 108.2 . . ? H13A C13 H13B 107.3 . . ? C13 C14 C15 110.3(4) . . ? C13 C14 H14A 109.6 . . ? C15 C14 H14A 109.6 . . ? C13 C14 H14B 109.6 . . ? C15 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C16 C15 C14 113.1(4) . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 C17 C18 116.7(3) . . ? C22 C17 I2 121.5(2) . . ? C18 C17 I2 121.8(2) . . ? F1 C18 C17 118.8(3) . . ? F1 C18 C19 117.8(3) . . ? C17 C18 C19 123.4(3) . . ? C20 C19 C18 116.8(3) . . ? C20 C19 I1 123.4(2) . . ? C18 C19 I1 119.8(2) . . ? F2 C20 C21 118.7(3) . . ? F2 C20 C19 118.5(3) . . ? C21 C20 C19 122.8(3) . . ? C20 C21 C22 117.4(3) . . ? C20 C21 I3 122.6(2) . . ? C22 C21 I3 120.0(3) . . ? F3 C22 C17 118.3(3) . . ? F3 C22 C21 118.7(3) . . ? C17 C22 C21 123.0(3) . . ? C23 Cl1 C23 55.2(6) . 3_566 ? Cl1 C23 Cl1 124.8(6) . 3_566 ? Cl1 C23 H23A 106.1 . . ? Cl1 C23 H23A 106.1 3_566 . ? Cl1 C23 H23B 106.1 . . ? Cl1 C23 H23B 106.1 3_566 . ? H23A C23 H23B 106.3 . . ? 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 C9 N1 C1 C2 57.8(4) . . . . ? C5 N1 C1 C2 -60.2(4) . . . . ? C13 N1 C1 C2 177.9(4) . . . . ? N1 C1 C2 C3 -163.7(4) . . . . ? C1 C2 C3 C4 -176.8(5) . . . . ? C1 N1 C5 C6 -63.5(5) . . . . ? C9 N1 C5 C6 176.3(4) . . . . ? C13 N1 C5 C6 55.9(5) . . . . ? N1 C5 C6 C7 -172.2(4) . . . . ? C5 C6 C7 C8 73.1(5) . . . . ? C1 N1 C9 C10 49.2(4) . . . . ? C5 N1 C9 C10 170.2(3) . . . . ? C13 N1 C9 C10 -68.9(4) . . . . ? N1 C9 C10 C11 173.7(3) . . . . ? C9 C10 C11 C12 -72.1(5) . . . . ? C1 N1 C13 C14 177.8(3) . . . . ? C9 N1 C13 C14 -62.3(4) . . . . ? C5 N1 C13 C14 55.7(4) . . . . ? N1 C13 C14 C15 -175.5(3) . . . . ? C13 C14 C15 C16 -177.8(4) . . . . ? C22 C17 C18 F1 -179.6(3) . . . . ? I2 C17 C18 F1 -0.4(4) . . . . ? C22 C17 C18 C19 0.4(5) . . . . ? I2 C17 C18 C19 179.7(3) . . . . ? F1 C18 C19 C20 179.5(3) . . . . ? C17 C18 C19 C20 -0.6(5) . . . . ? F1 C18 C19 I1 -1.8(4) . . . . ? C17 C18 C19 I1 178.1(3) . . . . ? C18 C19 C20 F2 179.6(3) . . . . ? I1 C19 C20 F2 0.9(4) . . . . ? C18 C19 C20 C21 0.2(5) . . . . ? I1 C19 C20 C21 -178.4(3) . . . . ? F2 C20 C21 C22 -179.0(3) . . . . ? C19 C20 C21 C22 0.3(5) . . . . ? F2 C20 C21 I3 0.4(5) . . . . ? C19 C20 C21 I3 179.7(3) . . . . ? C18 C17 C22 F3 179.9(3) . . . . ? I2 C17 C22 F3 0.7(4) . . . . ? C18 C17 C22 C21 0.2(5) . . . . ? I2 C17 C22 C21 -179.1(3) . . . . ? C20 C21 C22 F3 179.7(3) . . . . ? I3 C21 C22 F3 0.3(4) . . . . ? C20 C21 C22 C17 -0.5(5) . . . . ? I3 C21 C22 C17 -180.0(3) . . . . ? C23 Cl1 C23 Cl1 0.000(1) 3_566 . . 3_566 ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.326 _refine_diff_density_min -1.751 _refine_diff_density_rms 0.172 # Attachment '14.CIF' data_re192lt _database_code_depnum_ccdc_archive 'CCDC 665598' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H20 P 1+, I 1-, C6F3 I3, C H CL3' _chemical_formula_sum 'C31 H21 Cl3 F3 I4 P' _chemical_formula_weight 1095.40 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 18.725(2) _cell_length_b 9.5403(12) _cell_length_c 20.180(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3605.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 27994 _cell_measurement_theta_min 2.362 _cell_measurement_theta_max 31.060 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.018 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2048 _exptl_absorpt_coefficient_mu 3.760 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_absorpt_correction_T_min 0.570916 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; OXFORD low temperature device. ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 86581 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 34.57 _reflns_number_total 14696 _reflns_number_gt 12594 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0423P)^2^+1.4256P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.024(15) _refine_ls_number_reflns 14696 _refine_ls_number_parameters 494 _refine_ls_number_restraints 514 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0777 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.056 _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 0.253711(12) 0.05592(2) 0.16664(2) 0.03891(5) Uani 1 1 d . . . I2 I 0.133461(13) 0.31580(3) -0.083571(19) 0.04836(7) Uani 1 1 d . . . I3 I 0.006050(11) 0.47343(2) 0.18043(2) 0.03863(5) Uani 1 1 d . . . I4 I -0.128248(12) 0.67978(3) 0.24533(2) 0.04150(5) Uani 1 1 d . . . F1 F 0.12937(12) 0.2525(3) 0.22287(11) 0.0477(6) Uani 1 1 d . . . F2 F 0.04294(14) 0.4641(3) 0.02873(13) 0.0514(6) Uani 1 1 d . . . F3 F 0.22677(13) 0.1335(3) 0.01626(11) 0.0534(6) Uani 1 1 d . . . C1 C 0.18027(18) 0.1908(3) 0.12070(16) 0.0342(6) Uani 1 1 d . . . C2 C 0.13093(17) 0.2683(4) 0.15639(16) 0.0346(6) Uani 1 1 d . . . C3 C 0.08348(18) 0.3599(4) 0.12713(16) 0.0346(6) Uani 1 1 d . . . C4 C 0.08705(17) 0.3735(4) 0.05903(17) 0.0368(6) Uani 1 1 d . . . C5 C 0.13392(18) 0.2971(4) 0.01998(18) 0.0388(7) Uani 1 1 d . . . C6 C 0.17985(18) 0.2075(4) 0.05273(16) 0.0379(7) Uani 1 1 d . . . P1 P -0.01289(4) -0.14889(9) -0.07256(4) 0.03062(14) Uani 1 1 d D . . C7 C -0.06104(11) -0.3121(3) -0.06795(17) 0.0373(6) Uani 1 1 d DU B . C10 C -0.13501(19) -0.5650(4) -0.0674(3) 0.0622(12) Uani 1 1 d DU . . H10 H -0.1603 -0.6489 -0.0668 0.075 Uiso 1 1 calc R A 2 C8A C -0.08186(18) -0.3751(5) -0.0094(3) 0.0358(10) Uani 0.686(5) 1 d PDU B -1 H8A H -0.0708 -0.3324 0.0307 0.043 Uiso 0.686(5) 1 calc PR B -1 C9A C -0.1189(2) -0.5007(6) -0.0095(3) 0.0423(12) Uani 0.686(5) 1 d PDU B -1 H9A H -0.1328 -0.5411 0.0305 0.051 Uiso 0.686(5) 1 calc PR B -1 C11A C -0.1157(2) -0.5052(6) -0.1268(4) 0.0497(14) Uani 0.686(5) 1 d PDU B -1 H11A H -0.1274 -0.5485 -0.1666 0.060 Uiso 0.686(5) 1 calc PR B -1 C12A C -0.0784(2) -0.3785(4) -0.1262(2) 0.0420(12) Uani 0.686(5) 1 d PDU B -1 H12A H -0.0649 -0.3381 -0.1662 0.050 Uiso 0.686(5) 1 calc PR B -1 C8B C -0.1091(2) -0.3400(4) -0.0201(2) 0.062(4) Uani 0.314(5) 1 d PRDU B 2 H8B H -0.1185 -0.2739 0.0126 0.075 Uiso 0.314(5) 1 calc PR B 2 C9B C -0.1449(2) -0.4690(4) -0.0199(2) 0.083(5) Uani 0.314(5) 1 d PRDU B 2 H9B H -0.1765 -0.4886 0.0144 0.100 Uiso 0.314(5) 1 calc PR B 2 C11B C -0.0855(2) -0.5365(4) -0.1187(2) 0.102(6) Uani 0.314(5) 1 d PRDU B 2 H11B H -0.0772 -0.6024 -0.1517 0.122 Uiso 0.314(5) 1 calc PR B 2 C12B C -0.0495(2) -0.4103(4) -0.1193(2) 0.094(6) Uani 0.314(5) 1 d PRDU B 2 H12B H -0.0178 -0.3898 -0.1534 0.113 Uiso 0.314(5) 1 calc PR B 2 C13 C -0.06329(16) -0.0363(3) -0.12544(16) 0.0304(5) Uani 1 1 d D B . C14 C -0.02966(19) 0.0637(4) -0.1659(2) 0.0409(7) Uani 1 1 d D . . H14 H 0.0199 0.0685 -0.1680 0.049 Uiso 1 1 calc R B . C15 C -0.0714(3) 0.1553(4) -0.2027(2) 0.0528(10) Uani 1 1 d D B . H15 H -0.0496 0.2218 -0.2297 0.063 Uiso 1 1 calc R . . C16 C -0.1444(3) 0.1483(4) -0.1996(2) 0.0514(10) Uani 1 1 d D . . H16 H -0.1717 0.2107 -0.2244 0.062 Uiso 1 1 calc R B . C17 C -0.1779(2) 0.0508(4) -0.1605(2) 0.0481(8) Uani 1 1 d D B . H17 H -0.2275 0.0466 -0.1593 0.058 Uiso 1 1 calc R . . C18 C -0.13778(18) -0.0415(4) -0.1228(2) 0.0408(7) Uani 1 1 d D . . H18 H -0.1604 -0.1068 -0.0958 0.049 Uiso 1 1 calc R B . C19 C -0.00730(17) -0.0724(4) 0.00776(17) 0.0351(6) Uani 1 1 d D B . C20 C -0.0393(3) 0.0551(5) 0.0219(2) 0.0541(10) Uani 1 1 d D . . H20 H -0.0631 0.1037 -0.0113 0.065 Uiso 1 1 calc R B . C21 C -0.0361(3) 0.1105(6) 0.0850(3) 0.0686(14) Uani 1 1 d D B . H21 H -0.0562 0.1976 0.0936 0.082 Uiso 1 1 calc R . . C22 C -0.0030(3) 0.0372(6) 0.1350(3) 0.0668(15) Uani 1 1 d D . . H22 H -0.0034 0.0720 0.1780 0.080 Uiso 1 1 calc R B . C23 C 0.0305(4) -0.0874(6) 0.1213(2) 0.0820(19) Uani 1 1 d D B . H23 H 0.0550 -0.1344 0.1546 0.098 Uiso 1 1 calc R . . C24 C 0.0280(3) -0.1435(5) 0.0579(2) 0.0630(12) Uani 1 1 d D . . H24 H 0.0501 -0.2288 0.0490 0.076 Uiso 1 1 calc R B . C25A C 0.0746(3) -0.1799(6) -0.1029(3) 0.0291(14) Uani 0.686(5) 1 d PDU B -1 C26A C 0.0916(3) -0.2957(5) -0.1416(2) 0.0435(12) Uani 0.686(5) 1 d PDU B -1 H26A H 0.0581 -0.3661 -0.1490 0.052 Uiso 0.686(5) 1 calc PR B -1 C27A C 0.1594(3) -0.3046(6) -0.1691(3) 0.0529(14) Uani 0.686(5) 1 d PDU B -1 H27A H 0.1711 -0.3818 -0.1950 0.063 Uiso 0.686(5) 1 calc PR B -1 C28A C 0.2090(4) -0.2028(8) -0.1590(3) 0.049(2) Uani 0.686(5) 1 d PDU B -1 H28A H 0.2540 -0.2111 -0.1779 0.059 Uiso 0.686(5) 1 calc PR B -1 C29A C 0.1927(3) -0.0864(7) -0.1204(3) 0.0610(18) Uani 0.686(5) 1 d PDU B -1 H29A H 0.2268 -0.0169 -0.1135 0.073 Uiso 0.686(5) 1 calc PR B -1 C30A C 0.1249(3) -0.0746(6) -0.0920(3) 0.0529(16) Uani 0.686(5) 1 d PDU B -1 H30A H 0.1134 0.0028 -0.0660 0.064 Uiso 0.686(5) 1 calc PR B -1 C25B C 0.0783(8) -0.1441(17) -0.1117(6) 0.033(3) Uani 0.314(5) 1 d PDU B -2 C26B C 0.0832(6) -0.1763(15) -0.1791(5) 0.049(3) Uani 0.314(5) 1 d PDU B -2 H26B H 0.0426 -0.1914 -0.2046 0.058 Uiso 0.314(5) 1 calc PR B -2 C27B C 0.1506(6) -0.1848(19) -0.2061(7) 0.067(4) Uani 0.314(5) 1 d PDU B -2 H27B H 0.1559 -0.2049 -0.2509 0.080 Uiso 0.314(5) 1 calc PR B -2 C28B C 0.2101(9) -0.164(3) -0.1674(8) 0.064(5) Uani 0.314(5) 1 d PDU B -2 H28B H 0.2546 -0.1554 -0.1876 0.077 Uiso 0.314(5) 1 calc PR B -2 C29B C 0.2050(6) -0.155(2) -0.0993(7) 0.055(3) Uani 0.314(5) 1 d PDU B -2 H29B H 0.2461 -0.1575 -0.0734 0.066 Uiso 0.314(5) 1 calc PR B -2 C30B C 0.1380(5) -0.1425(15) -0.0697(6) 0.040(2) Uani 0.314(5) 1 d PDU B -2 H30B H 0.1332 -0.1333 -0.0241 0.048 Uiso 0.314(5) 1 calc PR B -2 C31A C 0.2680(9) 0.6129(18) 0.1263(6) 0.093(6) Uani 0.50 1 d PD C -1 H31A H 0.3021 0.6868 0.1380 0.111 Uiso 0.50 1 calc PR C -1 Cl1A Cl 0.2822(3) 0.4717(6) 0.1753(4) 0.151(3) Uani 0.50 1 d PD C -1 Cl2A Cl 0.1778(7) 0.6799(12) 0.1358(8) 0.126(5) Uani 0.50 1 d PD C -1 Cl3A Cl 0.2782(3) 0.5713(8) 0.0442(3) 0.126(2) Uani 0.50 1 d PD C -1 C31B C 0.2553(5) 0.6563(12) 0.1013(7) 0.060(3) Uani 0.50 1 d PD D -2 H31B H 0.2886 0.7216 0.1225 0.073 Uiso 0.50 1 calc PR D -2 Cl1B Cl 0.1807(5) 0.6441(11) 0.1492(6) 0.0805(15) Uani 0.50 1 d PD D -2 Cl2B Cl 0.2289(2) 0.7288(6) 0.02053(19) 0.1035(12) Uani 0.50 1 d PD D -2 Cl3B Cl 0.2985(2) 0.5016(5) 0.0877(3) 0.1158(16) Uani 0.50 1 d PD D -2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.04493(11) 0.04121(9) 0.03058(9) 0.00109(8) -0.00320(8) 0.00951(8) I2 0.03725(11) 0.07886(19) 0.02898(10) 0.01110(10) 0.00159(8) 0.00649(10) I3 0.04079(10) 0.03916(9) 0.03594(10) -0.00700(8) 0.00139(8) 0.00506(8) I4 0.03913(11) 0.05096(13) 0.03443(10) -0.01307(9) 0.00254(8) -0.00392(8) F1 0.0599(14) 0.0568(14) 0.0263(9) 0.0001(9) -0.0013(8) 0.0139(11) F2 0.0507(13) 0.0621(14) 0.0412(12) 0.0068(10) -0.0036(10) 0.0202(11) F3 0.0474(13) 0.0795(17) 0.0333(10) -0.0035(11) 0.0041(9) 0.0286(12) C1 0.0360(14) 0.0376(15) 0.0291(13) -0.0008(11) -0.0038(11) 0.0024(11) C2 0.0415(15) 0.0346(14) 0.0276(13) -0.0032(11) -0.0002(11) 0.0002(11) C3 0.0383(15) 0.0344(14) 0.0312(14) -0.0040(11) 0.0014(11) 0.0026(12) C4 0.0340(14) 0.0443(17) 0.0321(14) 0.0036(12) -0.0026(11) 0.0057(12) C5 0.0346(15) 0.0542(19) 0.0277(14) 0.0050(13) -0.0014(11) 0.0019(13) C6 0.0340(15) 0.0503(19) 0.0292(13) -0.0015(12) 0.0019(11) 0.0055(13) P1 0.0288(3) 0.0317(3) 0.0314(3) -0.0052(3) -0.0024(3) 0.0022(3) C7 0.0441(17) 0.0281(13) 0.0396(16) -0.0012(11) -0.0043(13) -0.0002(12) C10 0.063(2) 0.0365(19) 0.087(4) 0.001(2) 0.009(3) -0.0091(17) C8A 0.024(2) 0.050(3) 0.034(2) -0.001(2) 0.0018(16) -0.0021(18) C9A 0.025(2) 0.050(3) 0.052(3) 0.014(2) 0.0033(19) -0.0066(19) C11A 0.047(3) 0.040(3) 0.062(4) -0.012(3) 0.004(3) 0.000(2) C12A 0.044(3) 0.041(3) 0.042(3) 0.001(2) 0.002(2) 0.004(2) C8B 0.068(9) 0.041(7) 0.078(10) -0.007(6) 0.004(8) -0.019(6) C9B 0.076(11) 0.077(10) 0.096(12) 0.002(9) 0.000(10) -0.024(9) C11B 0.152(14) 0.050(8) 0.104(12) -0.045(8) 0.020(12) -0.020(10) C12B 0.142(13) 0.046(7) 0.093(11) -0.038(8) 0.028(11) 0.004(9) C13 0.0316(13) 0.0288(13) 0.0306(13) -0.0032(10) 0.0025(10) 0.0005(10) C14 0.0405(16) 0.0441(17) 0.0382(16) 0.0027(14) 0.0012(14) -0.0101(13) C15 0.080(3) 0.0403(19) 0.0382(18) 0.0070(15) -0.0101(18) -0.0111(19) C16 0.072(3) 0.0403(18) 0.042(2) 0.0004(15) -0.0178(18) 0.0101(18) C17 0.0370(16) 0.057(2) 0.051(2) 0.0009(17) -0.0058(15) 0.0116(14) C18 0.0316(14) 0.0490(19) 0.0418(18) 0.0041(14) 0.0026(13) 0.0013(13) C19 0.0331(14) 0.0412(15) 0.0310(14) -0.0108(12) 0.0015(11) -0.0062(12) C20 0.059(2) 0.054(2) 0.049(2) -0.0222(18) -0.0092(19) 0.0157(18) C21 0.069(3) 0.077(3) 0.060(3) -0.040(3) 0.000(2) -0.001(2) C22 0.076(3) 0.080(4) 0.044(2) -0.025(2) 0.006(2) -0.030(3) C23 0.141(6) 0.071(3) 0.034(2) -0.004(2) -0.018(3) -0.009(4) C24 0.098(4) 0.053(2) 0.038(2) -0.0017(18) -0.012(2) 0.008(2) C25A 0.025(2) 0.027(3) 0.036(2) -0.001(2) 0.0001(17) -0.0004(19) C26A 0.039(2) 0.043(3) 0.049(3) -0.009(2) 0.007(2) 0.0014(19) C27A 0.044(3) 0.061(3) 0.054(3) -0.015(3) 0.012(3) 0.009(2) C28A 0.030(3) 0.059(5) 0.059(4) 0.001(3) 0.012(2) 0.010(2) C29A 0.035(3) 0.068(4) 0.080(5) -0.015(4) 0.006(3) -0.008(3) C30A 0.035(3) 0.047(3) 0.077(4) -0.022(3) 0.007(3) -0.005(2) C25B 0.038(6) 0.022(6) 0.037(6) 0.002(5) 0.003(4) 0.007(5) C26B 0.035(5) 0.083(8) 0.028(5) -0.005(5) 0.003(4) 0.021(5) C27B 0.046(6) 0.095(10) 0.060(8) -0.022(7) 0.010(6) 0.023(7) C28B 0.051(8) 0.074(11) 0.066(8) 0.013(8) 0.006(7) 0.024(7) C29B 0.031(5) 0.074(8) 0.060(7) 0.005(6) -0.006(5) 0.002(5) C30B 0.031(4) 0.040(5) 0.049(6) 0.002(5) -0.018(4) 0.002(4) C31A 0.071(9) 0.136(15) 0.070(9) 0.017(9) -0.012(7) -0.051(9) Cl1A 0.173(5) 0.131(4) 0.150(5) 0.036(4) -0.060(5) -0.093(4) Cl2A 0.101(4) 0.120(8) 0.157(10) -0.083(7) 0.046(5) -0.048(5) Cl3A 0.085(3) 0.212(6) 0.082(3) -0.038(3) 0.019(2) -0.027(3) C31B 0.038(4) 0.070(6) 0.074(8) -0.036(6) 0.000(5) -0.008(4) Cl1B 0.066(2) 0.079(3) 0.096(3) -0.040(3) 0.0340(19) -0.0281(19) Cl2B 0.078(2) 0.160(4) 0.073(2) -0.009(2) 0.0002(17) -0.002(2) Cl3B 0.086(3) 0.123(3) 0.138(4) -0.038(3) 0.005(3) 0.044(2) _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 2.099(3) . ? I2 C5 2.097(4) . ? I3 C3 2.105(3) . ? F1 C2 1.350(4) . ? F2 C4 1.343(4) . ? F3 C6 1.346(4) . ? C1 C6 1.381(5) . ? C1 C2 1.385(4) . ? C2 C3 1.379(5) . ? C3 C4 1.382(5) . ? C4 C5 1.386(5) . ? C5 C6 1.381(5) . ? P1 C25A 1.774(7) . ? P1 C19 1.781(3) . ? P1 C13 1.784(3) . ? P1 C7 1.802(3) . ? P1 C25B 1.881(15) . ? C7 C8B 1.347(5) . ? C7 C12A 1.374(5) . ? C7 C8A 1.382(6) . ? C7 C12B 1.413(5) . ? C10 C9B 1.339(6) . ? C10 C9A 1.355(8) . ? C10 C11A 1.374(8) . ? C10 C11B 1.416(6) . ? C10 H10 0.9300 . ? C8A C9A 1.384(7) . ? C8A H8A 0.9300 . ? C9A H9A 0.9300 . ? C11A C12A 1.397(7) . ? C11A H11A 0.9300 . ? C12A H12A 0.9300 . ? C8B C9B 1.4011 . ? C8B H8B 0.9300 . ? C9B H9B 0.9300 . ? C11B C12B 1.3793 . ? C11B H11B 0.9300 . ? C12B H12B 0.9300 . ? C13 C18 1.397(4) . ? C13 C14 1.405(4) . ? C14 C15 1.387(5) . ? C14 H14 0.9300 . ? C15 C16 1.371(6) . ? C15 H15 0.9300 . ? C16 C17 1.372(6) . ? C16 H16 0.9300 . ? C17 C18 1.386(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C24 1.386(6) . ? C19 C20 1.386(5) . ? C20 C21 1.378(6) . ? C20 H20 0.9300 . ? C21 C22 1.375(8) . ? C21 H21 0.9300 . ? C22 C23 1.372(8) . ? C22 H22 0.9300 . ? C23 C24 1.388(6) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25A C26A 1.390(8) . ? C25A C30A 1.394(7) . ? C26A C27A 1.388(7) . ? C26A H26A 0.9300 . ? C27A C28A 1.359(8) . ? C27A H27A 0.9300 . ? C28A C29A 1.390(9) . ? C28A H28A 0.9300 . ? C29A C30A 1.399(8) . ? C29A H29A 0.9300 . ? C30A H30A 0.9300 . ? C25B C26B 1.396(12) . ? C25B C30B 1.404(12) . ? C26B C27B 1.378(11) . ? C26B H26B 0.9300 . ? C27B C28B 1.374(13) . ? C27B H27B 0.9300 . ? C28B C29B 1.380(13) . ? C28B H28B 0.9300 . ? C29B C30B 1.395(11) . ? C29B H29B 0.9300 . ? C30B H30B 0.9300 . ? C31A Cl1A 1.693(15) . ? C31A Cl3A 1.713(13) . ? C31A Cl2A 1.815(19) . ? C31A H31A 0.9800 . ? C31B Cl1B 1.703(13) . ? C31B Cl3B 1.705(10) . ? C31B Cl2B 1.838(16) . ? C31B H31B 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 116.8(3) . . ? C6 C1 I1 120.9(2) . . ? C2 C1 I1 122.3(2) . . ? F1 C2 C3 118.8(3) . . ? F1 C2 C1 118.1(3) . . ? C3 C2 C1 123.1(3) . . ? C2 C3 C4 117.0(3) . . ? C2 C3 I3 123.4(2) . . ? C4 C3 I3 119.5(2) . . ? F2 C4 C3 118.9(3) . . ? F2 C4 C5 118.0(3) . . ? C3 C4 C5 123.1(3) . . ? C6 C5 C4 116.6(3) . . ? C6 C5 I2 122.1(3) . . ? C4 C5 I2 121.3(2) . . ? F3 C6 C1 118.6(3) . . ? F3 C6 C5 118.0(3) . . ? C1 C6 C5 123.4(3) . . ? C25A P1 C19 109.2(2) . . ? C25A P1 C13 112.5(2) . . ? C19 P1 C13 109.21(16) . . ? C25A P1 C7 109.6(2) . . ? C19 P1 C7 109.67(16) . . ? C13 P1 C7 106.64(12) . . ? C25A P1 C25B 11.8(5) . . ? C19 P1 C25B 108.6(4) . . ? C13 P1 C25B 102.4(4) . . ? C7 P1 C25B 119.8(5) . . ? C8B C7 C12A 111.4(3) . . ? C8B C7 C8A 27.4(2) . . ? C12A C7 C8A 117.7(4) . . ? C8B C7 C12B 119.8(4) . . ? C12A C7 C12B 26.27(9) . . ? C8A C7 C12B 112.4(3) . . ? C8B C7 P1 122.8(2) . . ? C12A C7 P1 118.2(3) . . ? C8A C7 P1 124.1(3) . . ? C12B C7 P1 117.3(3) . . ? C9B C10 C9A 26.2(3) . . ? C9B C10 C11A 112.2(4) . . ? C9A C10 C11A 120.4(5) . . ? C9B C10 C11B 118.9(4) . . ? C9A C10 C11B 113.5(4) . . ? C11A C10 C11B 27.35(16) . . ? C9B C10 H10 120.6 . . ? C9A C10 H10 119.4 . . ? C11A C10 H10 120.2 . . ? C11B C10 H10 120.6 . . ? C7 C8A C9A 121.1(5) . . ? C7 C8A H8A 119.4 . . ? C9A C8A H8A 119.4 . . ? C10 C9A C8A 120.3(5) . . ? C10 C9A H9A 119.9 . . ? C8A C9A H9A 119.9 . . ? C10 C11A C12A 118.9(6) . . ? C10 C11A H11A 120.6 . . ? C12A C11A H11A 120.6 . . ? C7 C12A C11A 121.6(5) . . ? C7 C12A H12A 119.2 . . ? C11A C12A H12A 119.2 . . ? C7 C8B C9B 119.7(2) . . ? C7 C8B H8B 120.2 . . ? C9B C8B H8B 120.2 . . ? C10 C9B C8B 122.2(3) . . ? C10 C9B H9B 118.9 . . ? C8B C9B H9B 118.9 . . ? C12B C11B C10 119.6(2) . . ? C12B C11B H11B 120.2 . . ? C10 C11B H11B 120.2 . . ? C11B C12B C7 119.9(2) . . ? C11B C12B H12B 120.1 . . ? C7 C12B H12B 120.1 . . ? C18 C13 C14 119.6(3) . . ? C18 C13 P1 118.9(3) . . ? C14 C13 P1 121.3(2) . . ? C15 C14 C13 119.1(3) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C16 C15 C14 120.4(4) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 121.1(4) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C16 C17 C18 119.9(4) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C13 119.9(3) . . ? C17 C18 H18 120.1 . . ? C13 C18 H18 120.1 . . ? C24 C19 C20 119.0(4) . . ? C24 C19 P1 119.5(3) . . ? C20 C19 P1 121.5(3) . . ? C21 C20 C19 120.5(4) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 120.1(5) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C23 C22 C21 119.9(4) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 120.3(5) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? C19 C24 C23 120.0(5) . . ? C19 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C26A C25A C30A 120.5(6) . . ? C26A C25A P1 122.5(4) . . ? C30A C25A P1 116.6(5) . . ? C27A C26A C25A 118.8(5) . . ? C27A C26A H26A 120.6 . . ? C25A C26A H26A 120.6 . . ? C28A C27A C26A 121.4(6) . . ? C28A C27A H27A 119.3 . . ? C26A C27A H27A 119.3 . . ? C27A C28A C29A 120.4(6) . . ? C27A C28A H28A 119.8 . . ? C29A C28A H28A 119.8 . . ? C28A C29A C30A 119.5(6) . . ? C28A C29A H29A 120.2 . . ? C30A C29A H29A 120.2 . . ? C25A C30A C29A 119.4(6) . . ? C25A C30A H30A 120.3 . . ? C29A C30A H30A 120.3 . . ? C26B C25B C30B 122.5(12) . . ? C26B C25B P1 117.6(9) . . ? C30B C25B P1 118.0(9) . . ? C27B C26B C25B 117.3(11) . . ? C27B C26B H26B 121.4 . . ? C25B C26B H26B 121.4 . . ? C28B C27B C26B 120.7(13) . . ? C28B C27B H27B 119.7 . . ? C26B C27B H27B 119.7 . . ? C27B C28B C29B 121.2(15) . . ? C27B C28B H28B 119.4 . . ? C29B C28B H28B 119.4 . . ? C28B C29B C30B 119.6(12) . . ? C28B C29B H29B 120.2 . . ? C30B C29B H29B 120.2 . . ? C29B C30B C25B 117.2(11) . . ? C29B C30B H30B 121.4 . . ? C25B C30B H30B 121.4 . . ? Cl1A C31A Cl3A 111.3(11) . . ? Cl1A C31A Cl2A 111.4(9) . . ? Cl3A C31A Cl2A 106.7(9) . . ? Cl1A C31A H31A 109.1 . . ? Cl3A C31A H31A 109.1 . . ? Cl2A C31A H31A 109.1 . . ? Cl1B C31B Cl3B 114.9(9) . . ? Cl1B C31B Cl2B 108.0(7) . . ? Cl3B C31B Cl2B 108.1(7) . . ? Cl1B C31B H31B 108.6 . . ? Cl3B C31B H31B 108.6 . . ? Cl2B C31B H31B 108.6 . . ? 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 F1 179.0(3) . . . . ? I1 C1 C2 F1 -1.8(4) . . . . ? C6 C1 C2 C3 -0.7(5) . . . . ? I1 C1 C2 C3 178.4(3) . . . . ? F1 C2 C3 C4 179.7(3) . . . . ? C1 C2 C3 C4 -0.6(5) . . . . ? F1 C2 C3 I3 -1.8(5) . . . . ? C1 C2 C3 I3 178.0(3) . . . . ? C2 C3 C4 F2 -178.5(3) . . . . ? I3 C3 C4 F2 3.0(5) . . . . ? C2 C3 C4 C5 2.0(6) . . . . ? I3 C3 C4 C5 -176.6(3) . . . . ? F2 C4 C5 C6 178.4(3) . . . . ? C3 C4 C5 C6 -2.1(6) . . . . ? F2 C4 C5 I2 -2.4(5) . . . . ? C3 C4 C5 I2 177.1(3) . . . . ? C2 C1 C6 F3 -179.7(3) . . . . ? I1 C1 C6 F3 1.2(5) . . . . ? C2 C1 C6 C5 0.7(6) . . . . ? I1 C1 C6 C5 -178.5(3) . . . . ? C4 C5 C6 F3 -179.0(3) . . . . ? I2 C5 C6 F3 1.8(5) . . . . ? C4 C5 C6 C1 0.7(6) . . . . ? I2 C5 C6 C1 -178.5(3) . . . . ? C25A P1 C7 C8B 145.2(3) . . . . ? C19 P1 C7 C8B 25.4(2) . . . . ? C13 P1 C7 C8B -92.8(3) . . . . ? C25B P1 C7 C8B 151.9(5) . . . . ? C25A P1 C7 C12A -67.8(2) . . . . ? C19 P1 C7 C12A 172.29(19) . . . . ? C13 P1 C7 C12A 54.16(18) . . . . ? C25B P1 C7 C12A -61.2(5) . . . . ? C25A P1 C7 C8A 112.2(2) . . . . ? C19 P1 C7 C8A -7.62(18) . . . . ? C13 P1 C7 C8A -125.75(17) . . . . ? C25B P1 C7 C8A 118.9(5) . . . . ? C25A P1 C7 C12B -38.1(3) . . . . ? C19 P1 C7 C12B -158.0(2) . . . . ? C13 P1 C7 C12B 83.9(2) . . . . ? C25B P1 C7 C12B -31.5(5) . . . . ? C8B C7 C8A C9A 83.3(6) . . . . ? C12A C7 C8A C9A -0.01(10) . . . . ? C12B C7 C8A C9A -28.50(16) . . . . ? P1 C7 C8A C9A 179.90(7) . . . . ? C9B C10 C9A C8A -79.3(6) . . . . ? C11A C10 C9A C8A -1.0(2) . . . . ? C11B C10 C9A C8A 28.8(3) . . . . ? C7 C8A C9A C10 0.50(16) . . . . ? C9B C10 C11A C12A 28.8(3) . . . . ? C9A C10 C11A C12A 1.0(2) . . . . ? C11B C10 C11A C12A -81.5(6) . . . . ? C8B C7 C12A C11A -29.4(3) . . . . ? C8A C7 C12A C11A 0.02(15) . . . . ? C12B C7 C12A C11A 84.94(15) . . . . ? P1 C7 C12A C11A -179.89(10) . . . . ? C10 C11A C12A C7 -0.5(2) . . . . ? C12A C7 C8B C9B 30.7(3) . . . . ? C8A C7 C8B C9B -78.4(6) . . . . ? C12B C7 C8B C9B 3.0(4) . . . . ? P1 C7 C8B C9B 179.62(9) . . . . ? C9A C10 C9B C8B 86.4(7) . . . . ? C11A C10 C9B C8B -27.9(4) . . . . ? C11B C10 C9B C8B 1.6(4) . . . . ? C7 C8B C9B C10 -2.6(2) . . . . ? C9B C10 C11B C12B -1.1(4) . . . . ? C9A C10 C11B C12B -29.7(3) . . . . ? C11A C10 C11B C12B 81.5(7) . . . . ? C10 C11B C12B C7 1.61(18) . . . . ? C8B C7 C12B C11B -2.6(4) . . . . ? C12A C7 C12B C11B -80.44(13) . . . . ? C8A C7 C12B C11B 26.92(18) . . . . ? P1 C7 C12B C11B -179.38(7) . . . . ? C25A P1 C13 C18 157.0(3) . . . . ? C19 P1 C13 C18 -81.6(3) . . . . ? C7 P1 C13 C18 36.8(3) . . . . ? C25B P1 C13 C18 163.4(5) . . . . ? C25A P1 C13 C14 -27.6(4) . . . . ? C19 P1 C13 C14 93.8(3) . . . . ? C7 P1 C13 C14 -147.8(3) . . . . ? C25B P1 C13 C14 -21.2(5) . . . . ? C18 C13 C14 C15 -0.3(5) . . . . ? P1 C13 C14 C15 -175.6(3) . . . . ? C13 C14 C15 C16 0.1(6) . . . . ? C14 C15 C16 C17 -0.4(6) . . . . ? C15 C16 C17 C18 0.8(7) . . . . ? C16 C17 C18 C13 -0.9(6) . . . . ? C14 C13 C18 C17 0.7(6) . . . . ? P1 C13 C18 C17 176.1(3) . . . . ? C25A P1 C19 C24 -58.3(4) . . . . ? C13 P1 C19 C24 178.3(4) . . . . ? C7 P1 C19 C24 61.8(4) . . . . ? C25B P1 C19 C24 -70.8(6) . . . . ? C25A P1 C19 C20 123.6(4) . . . . ? C13 P1 C19 C20 0.2(4) . . . . ? C7 P1 C19 C20 -116.3(3) . . . . ? C25B P1 C19 C20 111.1(6) . . . . ? C24 C19 C20 C21 0.0(7) . . . . ? P1 C19 C20 C21 178.1(4) . . . . ? C19 C20 C21 C22 -2.2(8) . . . . ? C20 C21 C22 C23 4.0(9) . . . . ? C21 C22 C23 C24 -3.4(10) . . . . ? C20 C19 C24 C23 0.5(8) . . . . ? P1 C19 C24 C23 -177.7(5) . . . . ? C22 C23 C24 C19 1.2(10) . . . . ? C19 P1 C25A C26A 144.3(3) . . . . ? C13 P1 C25A C26A -94.3(4) . . . . ? C7 P1 C25A C26A 24.2(4) . . . . ? C25B P1 C25A C26A -126(3) . . . . ? C19 P1 C25A C30A -42.1(3) . . . . ? C13 P1 C25A C30A 79.3(3) . . . . ? C7 P1 C25A C30A -162.2(3) . . . . ? C25B P1 C25A C30A 47(2) . . . . ? C30A C25A C26A C27A -0.03(9) . . . . ? P1 C25A C26A C27A 173.3(4) . . . . ? C25A C26A C27A C28A -0.02(9) . . . . ? C26A C27A C28A C29A 0.05(19) . . . . ? C27A C28A C29A C30A 0.0(3) . . . . ? C26A C25A C30A C29A 0.05(19) . . . . ? P1 C25A C30A C29A -173.7(4) . . . . ? C28A C29A C30A C25A 0.0(2) . . . . ? C25A P1 C25B C26B 96(3) . . . . ? C19 P1 C25B C26B -169.0(11) . . . . ? C13 P1 C25B C26B -53.6(13) . . . . ? C7 P1 C25B C26B 64.0(13) . . . . ? C25A P1 C25B C30B -69(2) . . . . ? C19 P1 C25B C30B 26.1(13) . . . . ? C13 P1 C25B C30B 141.6(11) . . . . ? C7 P1 C25B C30B -100.9(12) . . . . ? C30B C25B C26B C27B -10(2) . . . . ? P1 C25B C26B C27B -174.4(12) . . . . ? C25B C26B C27B C28B 1(3) . . . . ? C26B C27B C28B C29B 10(3) . . . . ? C27B C28B C29B C30B -11(3) . . . . ? C28B C29B C30B C25B 2(3) . . . . ? C26B C25B C30B C29B 9(2) . . . . ? P1 C25B C30B C29B 172.9(12) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 34.57 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 1.921 _refine_diff_density_min -0.745 _refine_diff_density_rms 0.116 # Attachment '15.cif.pdf' data_re186 _database_code_depnum_ccdc_archive 'CCDC 665599' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H36 K N2 O6 1+, I 1-, C6 F3 I3' _chemical_formula_sum 'C24 H36 F3 I4 K N2 O6' _chemical_formula_weight 1052.25 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' O O 0.0106 0.0060 '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' K K 0.2009 0.2494 '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 P21/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 12.2152(15) _cell_length_b 14.222(2) _cell_length_c 20.531(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.89(2) _cell_angle_gamma 90.00 _cell_volume 3564.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 21951 _cell_measurement_theta_min 2.199 _cell_measurement_theta_max 28.185 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.961 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 3.664 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 1997)' _exptl_absorpt_correction_T_min 0.667705 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 73188 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.25 _reflns_number_total 8821 _reflns_number_gt 7454 _reflns_threshold_expression >2s\(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson,1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0406P)^2^+4.4791P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00060(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8821 _refine_ls_number_parameters 362 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.38072(2) 0.53123(3) 0.326664(16) 0.07790(11) Uani 1 1 d . . . I2 I 0.76083(2) 0.788517(19) 0.256684(12) 0.06090(8) Uani 1 1 d . . . I3 I 0.77253(2) 0.57910(2) 0.512661(13) 0.06378(9) Uani 1 1 d . . . F1 F 0.5319(2) 0.6740(2) 0.24956(12) 0.0796(7) Uani 1 1 d . . . F2 F 0.8350(2) 0.70569(19) 0.39227(13) 0.0756(7) Uani 1 1 d . . . F3 F 0.5510(2) 0.5012(2) 0.44357(12) 0.0784(7) Uani 1 1 d . . . C19 C 0.5377(3) 0.5858(3) 0.34615(19) 0.0577(9) Uani 1 1 d . . . C20 C 0.5860(3) 0.6496(3) 0.30532(18) 0.0570(9) Uani 1 1 d . . . C21 C 0.6864(3) 0.6904(3) 0.31882(18) 0.0539(8) Uani 1 1 d . . . C22 C 0.7377(3) 0.6658(3) 0.37708(19) 0.0561(8) Uani 1 1 d . . . C23 C 0.6953(3) 0.6035(3) 0.42105(18) 0.0541(8) Uani 1 1 d . . . C24 C 0.5954(3) 0.5633(3) 0.40316(19) 0.0559(8) Uani 1 1 d . . . I4 I 0.10029(2) 0.44698(2) 0.330458(12) 0.06021(8) Uani 1 1 d . . . K K 0.25294(6) 0.87109(6) 0.48254(4) 0.05339(18) Uani 1 1 d . . . C1 C 0.3642(7) 0.9316(6) 0.3199(3) 0.124(3) Uani 1 1 d . . . H1A H 0.3764 0.9711 0.2823 0.149 Uiso 1 1 calc R . . H1B H 0.3526 0.8678 0.3044 0.149 Uiso 1 1 calc R . . C2 C 0.4648(7) 0.9338(6) 0.3642(4) 0.130(3) Uani 1 1 d . . . H2A H 0.5286 0.9154 0.3404 0.156 Uiso 1 1 calc R . . H2B H 0.4767 0.9970 0.3809 0.156 Uiso 1 1 calc R . . O1 O 0.4493(3) 0.8720(4) 0.4154(2) 0.1046(13) Uani 1 1 d . . . C3 C 0.5458(5) 0.8590(7) 0.4539(4) 0.136(3) Uani 1 1 d . . . H3A H 0.5662 0.9179 0.4749 0.163 Uiso 1 1 calc R . . H3B H 0.6050 0.8403 0.4263 0.163 Uiso 1 1 calc R . . C4 C 0.5297(5) 0.7861(6) 0.5042(4) 0.128(3) Uani 1 1 d . . . H4A H 0.5046 0.7283 0.4835 0.154 Uiso 1 1 calc R . . H4B H 0.5988 0.7733 0.5271 0.154 Uiso 1 1 calc R . . O2 O 0.4536(3) 0.8158(3) 0.5480(2) 0.0894(10) Uani 1 1 d . . . C5 C 0.4399(5) 0.7497(4) 0.6021(4) 0.106(2) Uani 1 1 d . . . H5A H 0.5082 0.7448 0.6274 0.127 Uiso 1 1 calc R . . H5B H 0.4220 0.6879 0.5849 0.127 Uiso 1 1 calc R . . C6 C 0.3519(5) 0.7816(5) 0.6448(3) 0.1023(19) Uani 1 1 d . . . H6A H 0.3515 0.7417 0.6831 0.123 Uiso 1 1 calc R . . H6B H 0.3680 0.8452 0.6593 0.123 Uiso 1 1 calc R . . N1 N 0.2447(4) 0.7802(3) 0.6138(2) 0.0809(11) Uani 1 1 d . . . C7 C 0.2071(5) 0.6823(4) 0.6049(3) 0.0955(17) Uani 1 1 d . . . H7A H 0.1845 0.6581 0.6465 0.115 Uiso 1 1 calc R . . H7B H 0.2680 0.6443 0.5910 0.115 Uiso 1 1 calc R . . C8 C 0.1139(4) 0.6723(4) 0.5560(3) 0.0823(14) Uani 1 1 d . . . H8A H 0.0882 0.6078 0.5550 0.099 Uiso 1 1 calc R . . H8B H 0.0536 0.7125 0.5679 0.099 Uiso 1 1 calc R . . O3 O 0.1510(2) 0.6984(2) 0.49388(15) 0.0669(7) Uani 1 1 d . . . C9 C 0.0697(3) 0.6787(3) 0.4450(2) 0.0696(11) Uani 1 1 d . . . H9A H 0.0028 0.7121 0.4546 0.083 Uiso 1 1 calc R . . H9B H 0.0537 0.6119 0.4447 0.083 Uiso 1 1 calc R . . C10 C 0.1070(4) 0.7075(3) 0.3805(2) 0.0739(12) Uani 1 1 d . . . H10A H 0.1764 0.6774 0.3721 0.089 Uiso 1 1 calc R . . H10B H 0.0541 0.6876 0.3471 0.089 Uiso 1 1 calc R . . O4 O 0.1197(3) 0.8067(2) 0.37796(14) 0.0713(8) Uani 1 1 d . . . C11 C 0.1407(6) 0.8362(5) 0.3138(2) 0.1007(18) Uani 1 1 d . . . H11A H 0.0771 0.8237 0.2856 0.121 Uiso 1 1 calc R . . H11B H 0.2021 0.8012 0.2974 0.121 Uiso 1 1 calc R . . C12 C 0.1657(7) 0.9378(5) 0.3132(3) 0.114(2) Uani 1 1 d . . . H12A H 0.1748 0.9575 0.2685 0.137 Uiso 1 1 calc R . . H12B H 0.1036 0.9718 0.3297 0.137 Uiso 1 1 calc R . . N2 N 0.2646(5) 0.9641(3) 0.3521(2) 0.0921(13) Uani 1 1 d . . . C13 C 0.2715(7) 1.0638(5) 0.3619(3) 0.119(2) Uani 1 1 d . . . H13A H 0.2650 1.0946 0.3197 0.143 Uiso 1 1 calc R . . H13B H 0.3434 1.0786 0.3806 0.143 Uiso 1 1 calc R . . C14 C 0.1873(6) 1.1032(4) 0.4047(3) 0.107(2) Uani 1 1 d . . . H14A H 0.1947 1.1711 0.4066 0.129 Uiso 1 1 calc R . . H14B H 0.1149 1.0887 0.3866 0.129 Uiso 1 1 calc R . . O5 O 0.1993(3) 1.0646(2) 0.46957(19) 0.0814(9) Uani 1 1 d . . . C15 C 0.1206(5) 1.0978(4) 0.5104(3) 0.0897(16) Uani 1 1 d . . . H15A H 0.0494 1.0732 0.4967 0.108 Uiso 1 1 calc R . . H15B H 0.1175 1.1658 0.5080 0.108 Uiso 1 1 calc R . . C16 C 0.1469(4) 1.0683(3) 0.5784(3) 0.0843(15) Uani 1 1 d . . . H16A H 0.2181 1.0931 0.5919 0.101 Uiso 1 1 calc R . . H16B H 0.0930 1.0943 0.6070 0.101 Uiso 1 1 calc R . . O6 O 0.1479(3) 0.9679(2) 0.58436(16) 0.0787(9) Uani 1 1 d . . . C17 C 0.1790(6) 0.9392(5) 0.6472(3) 0.0982(18) Uani 1 1 d . . . H17A H 0.1338 0.9707 0.6785 0.118 Uiso 1 1 calc R . . H17B H 0.2547 0.9568 0.6565 0.118 Uiso 1 1 calc R . . C18 C 0.1670(6) 0.8357(5) 0.6539(2) 0.1024(19) Uani 1 1 d . . . H18A H 0.0925 0.8184 0.6412 0.123 Uiso 1 1 calc R . . H18B H 0.1787 0.8189 0.6994 0.123 Uiso 1 1 calc 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 0.05717(16) 0.1048(2) 0.07112(18) 0.00127(16) -0.00801(13) -0.02435(15) I2 0.07351(17) 0.05811(15) 0.05051(14) 0.00353(10) -0.00656(11) -0.01102(11) I3 0.06165(16) 0.07336(18) 0.05555(15) 0.01185(12) -0.01004(11) 0.00072(12) F1 0.0687(15) 0.112(2) 0.0565(13) 0.0167(13) -0.0219(11) -0.0209(14) F2 0.0638(14) 0.0882(17) 0.0730(15) 0.0177(13) -0.0257(12) -0.0271(12) F3 0.0715(15) 0.0973(19) 0.0664(15) 0.0206(14) 0.0007(12) -0.0238(14) C19 0.0494(19) 0.070(2) 0.053(2) -0.0050(17) -0.0015(15) -0.0120(17) C20 0.0530(19) 0.070(2) 0.0474(18) -0.0014(17) -0.0081(15) -0.0017(17) C21 0.057(2) 0.057(2) 0.0476(18) 0.0017(15) -0.0048(15) -0.0066(16) C22 0.0523(19) 0.059(2) 0.056(2) 0.0017(16) -0.0105(16) -0.0079(16) C23 0.0518(19) 0.061(2) 0.0487(18) 0.0037(16) -0.0079(15) 0.0006(16) C24 0.055(2) 0.061(2) 0.0516(19) 0.0039(16) 0.0019(16) -0.0049(16) I4 0.05896(15) 0.07014(17) 0.05133(14) -0.00996(11) -0.00114(10) -0.00069(11) K 0.0515(4) 0.0570(4) 0.0516(4) -0.0041(3) -0.0007(3) -0.0021(3) C1 0.157(7) 0.144(6) 0.075(4) 0.000(4) 0.047(4) -0.030(5) C2 0.115(6) 0.161(7) 0.117(6) -0.015(5) 0.050(5) -0.041(5) O1 0.069(2) 0.146(4) 0.101(3) -0.021(3) 0.025(2) -0.025(2) C3 0.054(3) 0.216(10) 0.138(6) -0.061(7) 0.026(4) 0.004(4) C4 0.072(4) 0.161(7) 0.149(7) -0.043(6) -0.014(4) 0.041(4) O2 0.0632(19) 0.092(2) 0.112(3) -0.014(2) -0.0163(18) 0.0171(17) C5 0.094(4) 0.084(4) 0.136(5) 0.004(4) -0.057(4) 0.016(3) C6 0.110(5) 0.113(5) 0.082(4) 0.017(3) -0.038(3) -0.002(4) N1 0.093(3) 0.084(3) 0.064(2) 0.0093(19) -0.020(2) -0.011(2) C7 0.114(4) 0.087(4) 0.083(3) 0.027(3) -0.022(3) -0.021(3) C8 0.089(3) 0.076(3) 0.082(3) 0.013(2) 0.002(3) -0.023(3) O3 0.0573(16) 0.0689(17) 0.0740(18) 0.0002(14) -0.0068(13) -0.0126(13) C9 0.058(2) 0.061(2) 0.089(3) -0.016(2) -0.009(2) -0.0061(18) C10 0.071(3) 0.074(3) 0.076(3) -0.029(2) -0.005(2) 0.000(2) O4 0.087(2) 0.0711(18) 0.0547(16) -0.0111(13) -0.0098(14) -0.0008(15) C11 0.130(5) 0.115(5) 0.057(3) -0.004(3) -0.017(3) -0.019(4) C12 0.157(6) 0.121(5) 0.064(3) 0.025(3) -0.029(4) -0.016(5) N2 0.128(4) 0.084(3) 0.065(2) 0.006(2) 0.006(2) -0.013(3) C13 0.186(8) 0.084(4) 0.090(4) 0.020(3) 0.019(5) -0.011(4) C14 0.162(6) 0.061(3) 0.097(4) 0.016(3) -0.023(4) 0.005(3) O5 0.087(2) 0.0648(18) 0.092(2) -0.0074(17) -0.0033(18) 0.0114(16) C15 0.082(3) 0.066(3) 0.121(5) -0.017(3) -0.001(3) 0.006(2) C16 0.079(3) 0.068(3) 0.107(4) -0.038(3) 0.026(3) -0.005(2) O6 0.084(2) 0.084(2) 0.0689(19) -0.0234(16) 0.0063(16) -0.0041(17) C17 0.123(5) 0.110(5) 0.063(3) -0.021(3) 0.011(3) -0.005(4) C18 0.134(5) 0.125(5) 0.049(2) 0.005(3) 0.019(3) -0.009(4) _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 C19 2.095(4) . ? I2 C21 2.116(4) . ? I3 C23 2.105(4) . ? F1 C20 1.348(4) . ? F2 C22 1.344(4) . ? F3 C24 1.339(4) . ? C19 C20 1.381(6) . ? C19 C24 1.383(5) . ? C20 C21 1.377(5) . ? C21 C22 1.377(5) . ? C22 C23 1.379(5) . ? C23 C24 1.386(5) . ? K O3 2.766(3) . ? K O4 2.805(3) . ? K O1 2.806(4) . ? K O5 2.839(3) . ? K O6 2.844(3) . ? K O2 2.866(3) . ? K N1 2.993(4) . ? K N2 2.995(4) . ? C1 N2 1.478(9) . ? C1 C2 1.505(10) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 O1 1.388(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? O1 C3 1.410(8) . ? C3 C4 1.481(12) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O2 1.381(8) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? O2 C5 1.469(8) . ? C5 C6 1.481(9) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N1 1.437(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N1 C7 1.475(7) . ? N1 C18 1.503(8) . ? C7 C8 1.500(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O3 1.418(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? O3 C9 1.417(5) . ? C9 C10 1.474(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O4 1.421(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? O4 C11 1.414(6) . ? C11 C12 1.477(9) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N2 1.474(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? N2 C13 1.434(8) . ? C13 C14 1.485(10) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O5 1.444(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? O5 C15 1.380(7) . ? C15 C16 1.483(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 O6 1.434(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? O6 C17 1.394(7) . ? C17 C18 1.486(9) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? 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 C20 C19 C24 116.7(3) . . ? C20 C19 I1 122.3(3) . . ? C24 C19 I1 120.9(3) . . ? F1 C20 C21 118.1(3) . . ? F1 C20 C19 118.5(3) . . ? C21 C20 C19 123.4(3) . . ? C20 C21 C22 116.4(3) . . ? C20 C21 I2 123.7(3) . . ? C22 C21 I2 119.9(3) . . ? F2 C22 C21 117.9(3) . . ? F2 C22 C23 117.9(3) . . ? C21 C22 C23 124.2(3) . . ? C22 C23 C24 116.0(3) . . ? C22 C23 I3 121.6(3) . . ? C24 C23 I3 122.3(3) . . ? F3 C24 C19 118.1(3) . . ? F3 C24 C23 118.6(3) . . ? C19 C24 C23 123.2(4) . . ? O3 K O4 61.53(9) . . ? O3 K O1 116.07(12) . . ? O4 K O1 96.26(11) . . ? O3 K O5 139.92(10) . . ? O4 K O5 96.79(10) . . ? O1 K O5 98.51(13) . . ? O3 K O6 98.78(10) . . ? O4 K O6 117.15(10) . . ? O1 K O6 140.61(12) . . ? O5 K O6 59.44(11) . . ? O3 K O2 95.58(10) . . ? O4 K O2 137.31(10) . . ? O1 K O2 60.00(13) . . ? O5 K O2 120.07(11) . . ? O6 K O2 100.81(11) . . ? O3 K N1 60.80(10) . . ? O4 K N1 120.80(11) . . ? O1 K N1 119.94(14) . . ? O5 K N1 119.26(12) . . ? O6 K N1 61.19(12) . . ? O2 K N1 60.87(12) . . ? O3 K N2 120.13(11) . . ? O4 K N2 60.19(12) . . ? O1 K N2 59.46(15) . . ? O5 K N2 60.37(12) . . ? O6 K N2 118.66(13) . . ? O2 K N2 118.39(14) . . ? N1 K N2 179.00(14) . . ? N2 C1 C2 113.0(6) . . ? N2 C1 H1A 109.0 . . ? C2 C1 H1A 109.0 . . ? N2 C1 H1B 109.0 . . ? C2 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? O1 C2 C1 108.4(6) . . ? O1 C2 H2A 110.0 . . ? C1 C2 H2A 110.0 . . ? O1 C2 H2B 110.0 . . ? C1 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? C2 O1 C3 112.0(6) . . ? C2 O1 K 121.0(4) . . ? C3 O1 K 115.9(4) . . ? O1 C3 C4 110.8(6) . . ? O1 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? O1 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? O2 C4 C3 110.3(6) . . ? O2 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? O2 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C4 O2 C5 113.1(5) . . ? C4 O2 K 111.2(4) . . ? C5 O2 K 114.4(3) . . ? O2 C5 C6 110.8(5) . . ? O2 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? O2 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N1 C6 C5 113.7(5) . . ? N1 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? N1 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C6 N1 C7 110.1(5) . . ? C6 N1 C18 109.4(5) . . ? C7 N1 C18 111.4(5) . . ? C6 N1 K 109.6(3) . . ? C7 N1 K 108.4(3) . . ? C18 N1 K 107.9(3) . . ? N1 C7 C8 113.5(4) . . ? N1 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N1 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? O3 C8 C7 108.6(4) . . ? O3 C8 H8A 110.0 . . ? C7 C8 H8A 110.0 . . ? O3 C8 H8B 110.0 . . ? C7 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? C9 O3 C8 110.3(3) . . ? C9 O3 K 115.1(3) . . ? C8 O3 K 117.8(3) . . ? O3 C9 C10 110.5(4) . . ? O3 C9 H9A 109.6 . . ? C10 C9 H9A 109.6 . . ? O3 C9 H9B 109.6 . . ? C10 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? O4 C10 C9 110.3(4) . . ? O4 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? O4 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C11 O4 C10 110.6(4) . . ? C11 O4 K 119.9(3) . . ? C10 O4 K 110.9(3) . . ? O4 C11 C12 110.0(5) . . ? O4 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? O4 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? N2 C12 C11 114.2(5) . . ? N2 C12 H12A 108.7 . . ? C11 C12 H12A 108.7 . . ? N2 C12 H12B 108.7 . . ? C11 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C13 N2 C12 111.7(6) . . ? C13 N2 C1 109.0(6) . . ? C12 N2 C1 110.6(6) . . ? C13 N2 K 108.4(4) . . ? C12 N2 K 108.0(3) . . ? C1 N2 K 109.0(4) . . ? N2 C13 C14 114.7(6) . . ? N2 C13 H13A 108.6 . . ? C14 C13 H13A 108.6 . . ? N2 C13 H13B 108.6 . . ? C14 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? O5 C14 C13 110.6(5) . . ? O5 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? O5 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C15 O5 C14 112.3(5) . . ? C15 O5 K 116.0(3) . . ? C14 O5 K 118.1(3) . . ? O5 C15 C16 110.0(4) . . ? O5 C15 H15A 109.7 . . ? C16 C15 H15A 109.7 . . ? O5 C15 H15B 109.7 . . ? C16 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? O6 C16 C15 111.3(4) . . ? O6 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? O6 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C17 O6 C16 111.8(4) . . ? C17 O6 K 115.0(3) . . ? C16 O6 K 115.0(3) . . ? O6 C17 C18 110.5(5) . . ? O6 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? O6 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 N1 113.8(5) . . ? C17 C18 H18A 108.8 . . ? N1 C18 H18A 108.8 . . ? C17 C18 H18B 108.8 . . ? N1 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? 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 C24 C19 C20 F1 -179.4(4) . . . . ? I1 C19 C20 F1 -3.1(5) . . . . ? C24 C19 C20 C21 0.0(6) . . . . ? I1 C19 C20 C21 176.3(3) . . . . ? F1 C20 C21 C22 178.2(4) . . . . ? C19 C20 C21 C22 -1.2(6) . . . . ? F1 C20 C21 I2 -0.5(5) . . . . ? C19 C20 C21 I2 -179.8(3) . . . . ? C20 C21 C22 F2 -178.9(4) . . . . ? I2 C21 C22 F2 -0.2(5) . . . . ? C20 C21 C22 C23 0.6(6) . . . . ? I2 C21 C22 C23 179.3(3) . . . . ? F2 C22 C23 C24 -179.4(4) . . . . ? C21 C22 C23 C24 1.1(6) . . . . ? F2 C22 C23 I3 5.0(5) . . . . ? C21 C22 C23 I3 -174.4(3) . . . . ? C20 C19 C24 F3 -179.5(4) . . . . ? I1 C19 C24 F3 4.1(5) . . . . ? C20 C19 C24 C23 1.9(6) . . . . ? I1 C19 C24 C23 -174.4(3) . . . . ? C22 C23 C24 F3 179.0(4) . . . . ? I3 C23 C24 F3 -5.4(5) . . . . ? C22 C23 C24 C19 -2.4(6) . . . . ? I3 C23 C24 C19 173.1(3) . . . . ? N2 C1 C2 O1 62.9(9) . . . . ? C1 C2 O1 C3 171.1(6) . . . . ? C1 C2 O1 K -46.6(8) . . . . ? O3 K O1 C2 127.9(5) . . . . ? O4 K O1 C2 66.6(5) . . . . ? O5 K O1 C2 -31.2(5) . . . . ? O6 K O1 C2 -82.4(5) . . . . ? O2 K O1 C2 -151.2(5) . . . . ? N1 K O1 C2 -162.3(5) . . . . ? N2 K O1 C2 16.8(5) . . . . ? O3 K O1 C3 -91.1(5) . . . . ? O4 K O1 C3 -152.4(5) . . . . ? O5 K O1 C3 109.8(5) . . . . ? O6 K O1 C3 58.7(6) . . . . ? O2 K O1 C3 -10.1(5) . . . . ? N1 K O1 C3 -21.3(6) . . . . ? N2 K O1 C3 157.8(6) . . . . ? C2 O1 C3 C4 -174.7(6) . . . . ? K O1 C3 C4 40.9(8) . . . . ? O1 C3 C4 O2 -65.3(8) . . . . ? C3 C4 O2 C5 -175.6(5) . . . . ? C3 C4 O2 K 54.0(7) . . . . ? O3 K O2 C4 93.8(5) . . . . ? O4 K O2 C4 40.7(5) . . . . ? O1 K O2 C4 -23.1(5) . . . . ? O5 K O2 C4 -105.3(5) . . . . ? O6 K O2 C4 -166.1(5) . . . . ? N1 K O2 C4 145.8(5) . . . . ? N2 K O2 C4 -34.9(5) . . . . ? O3 K O2 C5 -35.9(4) . . . . ? O4 K O2 C5 -89.0(4) . . . . ? O1 K O2 C5 -152.8(4) . . . . ? O5 K O2 C5 125.0(4) . . . . ? O6 K O2 C5 64.2(4) . . . . ? N1 K O2 C5 16.1(4) . . . . ? N2 K O2 C5 -164.6(4) . . . . ? C4 O2 C5 C6 -175.8(5) . . . . ? K O2 C5 C6 -47.1(5) . . . . ? O2 C5 C6 N1 66.3(7) . . . . ? C5 C6 N1 C7 71.6(7) . . . . ? C5 C6 N1 C18 -165.7(5) . . . . ? C5 C6 N1 K -47.6(6) . . . . ? O3 K N1 C6 131.5(4) . . . . ? O4 K N1 C6 145.8(4) . . . . ? O1 K N1 C6 26.5(4) . . . . ? O5 K N1 C6 -94.7(4) . . . . ? O6 K N1 C6 -108.0(4) . . . . ? O2 K N1 C6 15.5(4) . . . . ? N2 K N1 C6 -27(8) . . . . ? O3 K N1 C7 11.3(3) . . . . ? O4 K N1 C7 25.6(4) . . . . ? O1 K N1 C7 -93.7(4) . . . . ? O5 K N1 C7 145.1(4) . . . . ? O6 K N1 C7 131.8(4) . . . . ? O2 K N1 C7 -104.7(4) . . . . ? N2 K N1 C7 -147(8) . . . . ? O3 K N1 C18 -109.5(4) . . . . ? O4 K N1 C18 -95.2(4) . . . . ? O1 K N1 C18 145.5(3) . . . . ? O5 K N1 C18 24.3(4) . . . . ? O6 K N1 C18 11.0(3) . . . . ? O2 K N1 C18 134.5(4) . . . . ? N2 K N1 C18 92(8) . . . . ? C6 N1 C7 C8 -162.6(5) . . . . ? C18 N1 C7 C8 76.0(6) . . . . ? K N1 C7 C8 -42.6(6) . . . . ? N1 C7 C8 O3 64.8(7) . . . . ? C7 C8 O3 C9 172.6(4) . . . . ? C7 C8 O3 K -52.5(5) . . . . ? O4 K O3 C9 -11.4(3) . . . . ? O1 K O3 C9 -94.1(3) . . . . ? O5 K O3 C9 52.8(3) . . . . ? O6 K O3 C9 104.8(3) . . . . ? O2 K O3 C9 -153.3(3) . . . . ? N1 K O3 C9 154.6(3) . . . . ? N2 K O3 C9 -25.8(3) . . . . ? O4 K O3 C8 -144.2(3) . . . . ? O1 K O3 C8 133.1(3) . . . . ? O5 K O3 C8 -80.0(3) . . . . ? O6 K O3 C8 -28.0(3) . . . . ? O2 K O3 C8 73.8(3) . . . . ? N1 K O3 C8 21.8(3) . . . . ? N2 K O3 C8 -158.6(3) . . . . ? C8 O3 C9 C10 178.8(4) . . . . ? K O3 C9 C10 42.6(4) . . . . ? O3 C9 C10 O4 -65.3(5) . . . . ? C9 C10 O4 C11 -171.9(4) . . . . ? C9 C10 O4 K 52.6(4) . . . . ? O3 K O4 C11 -152.3(4) . . . . ? O1 K O4 C11 -36.0(4) . . . . ? O5 K O4 C11 63.4(4) . . . . ? O6 K O4 C11 122.5(4) . . . . ? O2 K O4 C11 -87.4(4) . . . . ? N1 K O4 C11 -166.5(4) . . . . ? N2 K O4 C11 13.4(4) . . . . ? O3 K O4 C10 -21.4(3) . . . . ? O1 K O4 C10 94.9(3) . . . . ? O5 K O4 C10 -165.7(3) . . . . ? O6 K O4 C10 -106.7(3) . . . . ? O2 K O4 C10 43.4(3) . . . . ? N1 K O4 C10 -35.6(3) . . . . ? N2 K O4 C10 144.2(3) . . . . ? C10 O4 C11 C12 -173.8(5) . . . . ? K O4 C11 C12 -42.8(7) . . . . ? O4 C11 C12 N2 62.3(8) . . . . ? C11 C12 N2 C13 -167.0(6) . . . . ? C11 C12 N2 C1 71.4(7) . . . . ? C11 C12 N2 K -47.8(7) . . . . ? C2 C1 N2 C13 71.5(8) . . . . ? C2 C1 N2 C12 -165.3(6) . . . . ? C2 C1 N2 K -46.7(7) . . . . ? O3 K N2 C13 153.1(5) . . . . ? O4 K N2 C13 138.5(5) . . . . ? O1 K N2 C13 -102.5(5) . . . . ? O5 K N2 C13 19.7(5) . . . . ? O6 K N2 C13 31.9(5) . . . . ? O2 K N2 C13 -90.7(5) . . . . ? N1 K N2 C13 -49(8) . . . . ? O3 K N2 C12 31.9(5) . . . . ? O4 K N2 C12 17.3(4) . . . . ? O1 K N2 C12 136.2(5) . . . . ? O5 K N2 C12 -101.6(5) . . . . ? O6 K N2 C12 -89.4(4) . . . . ? O2 K N2 C12 148.1(4) . . . . ? N1 K N2 C12 -170(8) . . . . ? O3 K N2 C1 -88.3(4) . . . . ? O4 K N2 C1 -102.9(4) . . . . ? O1 K N2 C1 16.0(4) . . . . ? O5 K N2 C1 138.2(5) . . . . ? O6 K N2 C1 150.5(4) . . . . ? O2 K N2 C1 27.9(5) . . . . ? N1 K N2 C1 70(8) . . . . ? C12 N2 C13 C14 68.5(7) . . . . ? C1 N2 C13 C14 -169.0(6) . . . . ? K N2 C13 C14 -50.5(7) . . . . ? N2 C13 C14 O5 62.7(8) . . . . ? C13 C14 O5 C15 -178.4(5) . . . . ? C13 C14 O5 K -39.4(7) . . . . ? O3 K O5 C15 45.3(4) . . . . ? O4 K O5 C15 98.2(4) . . . . ? O1 K O5 C15 -164.4(4) . . . . ? O6 K O5 C15 -19.5(3) . . . . ? O2 K O5 C15 -104.3(4) . . . . ? N1 K O5 C15 -33.0(4) . . . . ? N2 K O5 C15 148.1(4) . . . . ? O3 K O5 C14 -92.3(4) . . . . ? O4 K O5 C14 -39.4(4) . . . . ? O1 K O5 C14 58.0(4) . . . . ? O6 K O5 C14 -157.0(4) . . . . ? O2 K O5 C14 118.1(4) . . . . ? N1 K O5 C14 -170.6(4) . . . . ? N2 K O5 C14 10.5(4) . . . . ? C14 O5 C15 C16 -171.0(4) . . . . ? K O5 C15 C16 49.0(5) . . . . ? O5 C15 C16 O6 -61.6(6) . . . . ? C15 C16 O6 C17 176.4(5) . . . . ? C15 C16 O6 K 42.8(5) . . . . ? O3 K O6 C17 70.9(4) . . . . ? O4 K O6 C17 133.4(4) . . . . ? O1 K O6 C17 -81.8(4) . . . . ? O5 K O6 C17 -145.2(4) . . . . ? O2 K O6 C17 -26.5(4) . . . . ? N1 K O6 C17 21.4(4) . . . . ? N2 K O6 C17 -157.5(4) . . . . ? O3 K O6 C16 -157.0(3) . . . . ? O4 K O6 C16 -94.6(3) . . . . ? O1 K O6 C16 50.3(4) . . . . ? O5 K O6 C16 -13.1(3) . . . . ? O2 K O6 C16 105.6(3) . . . . ? N1 K O6 C16 153.4(4) . . . . ? N2 K O6 C16 -25.4(4) . . . . ? C16 O6 C17 C18 173.5(5) . . . . ? K O6 C17 C18 -53.0(6) . . . . ? O6 C17 C18 N1 66.8(7) . . . . ? C6 N1 C18 C17 76.7(6) . . . . ? C7 N1 C18 C17 -161.4(5) . . . . ? K N1 C18 C17 -42.5(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 2.450 _refine_diff_density_min -1.540 _refine_diff_density_rms 0.087 # Attachment '16.CIF' data_re212_d _database_code_depnum_ccdc_archive 'CCDC 665600' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '0.58(C8 H20 P 1+), 0.42(C8 H20 N 1+), C6 F3 I3, I 1-' _chemical_formula_sum 'C14 H20 F3 I4 N0.42 P0.58' _chemical_formula_weight 776.79 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' F F 0.0171 0.0103 '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' P P 0.1023 0.0942 '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 trigonal _symmetry_space_group_name_H-M R-3c _symmetry_space_group_name_Hall '-R 3 2"c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'y, x, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'y+2/3, x+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' 'y+1/3, x+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-y, -x, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-y+2/3, -x+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' '-y+1/3, -x+2/3, z+1/6' _cell_length_a 20.903(3) _cell_length_b 20.903 _cell_length_c 27.778(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 10511(2) _cell_formula_units_Z 18 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7276 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 25.59 _exptl_crystal_description 'hexagonal prism' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6384 _exptl_absorpt_coefficient_mu 5.393 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_absorpt_correction_T_min 0.737948 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; Crystals were obtained from a solution containing 1,3,5-trifluoro benzene, tetraethylammonium iodide and tetraethylphosphoniumiodide with molecular ratio 1.0:1.0:1.0, respectively. ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 29699 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0115 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2302 _reflns_number_gt 1616 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. P1 and N1 atoms were constrained to have the same coordinates and ADPs. No attempt was made to split carbon atoms of tetraethylphosphonium and tetraethylammonium ions. Anomalous P-C, N-C, C-C distances and ADPs of the atom of the cations are due to this bias. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0268P)^2^+118.7127P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2302 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0994 _refine_ls_wR_factor_gt 0.0786 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 0.6667 0.16554(3) 0.0833 0.0857(2) Uani 1 2 d S . . C1 C 0.6667 0.2661(4) 0.0833 0.073(3) Uani 1 2 d S . . C2 C 0.6019(5) 0.2686(5) 0.0833 0.074(3) Uani 1 2 d S . . F1 F 0.5379(3) 0.2045(3) 0.0833 0.103(2) Uani 1 2 d S . . I2 I 0.83407(3) 0.33309(3) 0.22352(2) 0.0929(2) Uani 1 1 d . . . C3 C 0.6668(4) 0.2682(4) 0.2179(3) 0.084(2) Uani 1 1 d . . . C4 C 0.7339(4) 0.3336(4) 0.2176(3) 0.082(2) Uani 1 1 d . . . F2 F 0.6666(2) 0.2041(2) 0.2187(2) 0.1126(17) Uani 1 1 d . . . I3 I 1.0000 0.33971(3) 0.2500 0.0736(2) Uani 1 2 d S . . P1 P 0.62558(17) 0.0000 0.2500 0.0690(14) Uani 0.583(9) 2 d SP . 1 C5 C 0.5909(4) 0.0219(5) 0.2038(3) 0.096(2) Uani 1 1 d . . 1 H5A H 0.5894 0.0663 0.2121 0.115 Uiso 1 1 calc R . 1 H5B H 0.6246 0.0342 0.1769 0.115 Uiso 1 1 calc R . 1 C6 C 0.5159(4) -0.0347(6) 0.1872(3) 0.115(3) Uani 1 1 d . . 1 H6A H 0.5015 -0.0158 0.1604 0.173 Uiso 1 1 calc R . 1 H6B H 0.4812 -0.0466 0.2130 0.173 Uiso 1 1 calc R . 1 H6C H 0.5167 -0.0785 0.1775 0.173 Uiso 1 1 calc R . 1 C7 C 0.7057(5) 0.0716(5) 0.2648(3) 0.101(3) Uani 1 1 d . . 1 H7A H 0.6983 0.1127 0.2724 0.122 Uiso 1 1 calc R . 1 H7B H 0.7235 0.0595 0.2937 0.122 Uiso 1 1 calc R . 1 C8 C 0.7647(5) 0.0959(6) 0.2262(4) 0.126(4) Uani 1 1 d . . 1 H8A H 0.8090 0.1387 0.2371 0.188 Uiso 1 1 calc R . 1 H8B H 0.7476 0.1078 0.1973 0.188 Uiso 1 1 calc R . 1 H8C H 0.7747 0.0567 0.2198 0.188 Uiso 1 1 calc R . 1 N1 N 0.62558(17) 0.0000 0.2500 0.0690(14) Uani 0.42 2 d SP . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0800(4) 0.0664(3) 0.1152(6) 0.00361(19) 0.0072(4) 0.0400(2) C1 0.075(6) 0.062(4) 0.087(7) 0.001(3) 0.002(5) 0.038(3) C2 0.067(4) 0.067(4) 0.086(7) -0.003(3) 0.003(3) 0.031(5) F1 0.061(2) 0.061(2) 0.171(6) -0.003(2) 0.003(2) 0.019(3) I2 0.0686(3) 0.0760(3) 0.1384(5) -0.0011(3) 0.0145(3) 0.0392(2) C3 0.076(4) 0.070(4) 0.111(6) -0.005(4) 0.002(4) 0.039(4) C4 0.069(4) 0.070(4) 0.109(6) 0.001(4) 0.010(4) 0.036(4) F2 0.080(3) 0.065(2) 0.195(5) -0.020(3) -0.002(3) 0.038(2) I3 0.0694(4) 0.0643(3) 0.0887(4) 0.00818(16) 0.0164(3) 0.03472(19) P1 0.0663(18) 0.072(2) 0.070(2) -0.0139(17) -0.0070(9) 0.0361(12) C5 0.096(5) 0.113(6) 0.089(5) -0.011(5) 0.005(4) 0.060(5) C6 0.092(6) 0.157(9) 0.100(6) -0.013(6) -0.012(5) 0.065(6) C7 0.103(6) 0.094(6) 0.116(7) -0.018(5) -0.010(5) 0.057(5) C8 0.073(5) 0.129(8) 0.159(9) -0.011(7) 0.016(6) 0.039(5) N1 0.0663(18) 0.072(2) 0.070(2) -0.0139(17) -0.0070(9) 0.0361(12) _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. P1 and N1 atoms were constrained to have the same coordinates and ADPs. No attempt was made to split carbon atoms of tetraethylphosphonium and tetraethylammonium ions. Anomalous P-C, N-C distances and ADPss of the cation are due to this bias. ; 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(9) . ? C1 C2 1.380(6) . ? C1 C2 1.380(6) 2_655 ? C2 F1 1.339(11) . ? C2 C1 1.380(6) 3_665 ? I2 C4 2.106(7) . ? C3 F2 1.339(8) . ? C3 C4 1.380(9) 3_665 ? C3 C4 1.385(9) . ? C4 C3 1.380(9) 2_655 ? P1 C7 1.645(9) . ? P1 C7 1.645(8) 4 ? P1 C5 1.649(8) . ? P1 C5 1.649(8) 4 ? C5 C6 1.488(10) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.518(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C2 116.2(11) . 2_655 ? C2 C1 I1 121.9(5) . . ? C2 C1 I1 121.9(5) 2_655 . ? F1 C2 C1 118.1(5) . . ? F1 C2 C1 118.1(5) . 3_665 ? C1 C2 C1 123.8(11) . 3_665 ? F2 C3 C4 118.3(7) . 3_665 ? F2 C3 C4 118.9(7) . . ? C4 C3 C4 122.9(8) 3_665 . ? C3 C4 C3 117.1(8) 2_655 . ? C3 C4 I2 121.7(6) 2_655 . ? C3 C4 I2 120.9(6) . . ? C7 P1 C7 111.5(6) . 4 ? C7 P1 C5 109.3(4) . . ? C7 P1 C5 108.7(4) 4 . ? C7 P1 C5 108.7(4) . 4 ? C7 P1 C5 109.3(4) 4 4 ? C5 P1 C5 109.2(6) . 4 ? C6 C5 P1 117.0(7) . . ? C6 C5 H5A 108.1 . . ? P1 C5 H5A 108.1 . . ? C6 C5 H5B 108.1 . . ? P1 C5 H5B 108.1 . . ? H5A C5 H5B 107.3 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 P1 114.5(7) . . ? C8 C7 H7A 108.6 . . ? P1 C7 H7A 108.6 . . ? C8 C7 H7B 108.6 . . ? P1 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C2 F1 180.0 2_655 . . . ? I1 C1 C2 F1 0.0 . . . . ? C2 C1 C2 C1 0.0 2_655 . . 3_665 ? I1 C1 C2 C1 180.0 . . . 3_665 ? F2 C3 C4 C3 -178.5(5) . . . 2_655 ? C4 C3 C4 C3 1.1(18) 3_665 . . 2_655 ? F2 C3 C4 I2 -4.5(12) . . . . ? C4 C3 C4 I2 175.2(5) 3_665 . . . ? C7 P1 C5 C6 -176.2(7) . . . . ? C7 P1 C5 C6 61.9(8) 4 . . . ? C5 P1 C5 C6 -57.4(6) 4 . . . ? C7 P1 C7 C8 56.8(6) 4 . . . ? C5 P1 C7 C8 -63.4(8) . . . . ? C5 P1 C7 C8 177.5(7) 4 . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.129 _refine_diff_density_min -1.043 _refine_diff_density_rms 0.095 # Attachment '17.CIF' data_re228 _database_code_depnum_ccdc_archive 'CCDC 665601' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '0.64(C8 H20 N 1+), 0.36(C8 H20 P 1+), C6 F3 I3, I 1-' _chemical_formula_sum 'C14 H20 F3 I4 N0.64 P0.36' _chemical_formula_weight 772.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' P P 0.1023 0.0942 '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 trigonal _symmetry_space_group_name_H-M R-3c _symmetry_space_group_name_Hall '-R 3 2"c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'y, x, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'y+2/3, x+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' 'y+1/3, x+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-y, -x, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-y+2/3, -x+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' '-y+1/3, -x+2/3, z+1/6' _cell_length_a 20.891(3) _cell_length_b 20.891 _cell_length_c 27.594(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 10430(2) _cell_formula_units_Z 18 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7710 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 25.59 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6352 _exptl_absorpt_coefficient_mu 5.420 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_absorpt_correction_T_min 0.734646 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; Crystals were obtained from a solution containing 1,3,5-trifluoro benzene, tetraethylammonium iodide and tetraethylphosphoniumiodide with molecular ratio 1.0:1.4:0.7, respectively. ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 59062 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0082 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 26.09 _reflns_number_total 2306 _reflns_number_gt 1725 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. P1 and N1 atoms were constrained to have the same coordinates and ADPs. No attempt was made to split carbon atoms of tetraethylphosphonium and tetraethylammonium ions. Anomalous P-C, N-C, C-C distances and ADPs of the atom of the cations are due to this bias. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0278P)^2^+126.1977P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2306 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.1031 _refine_ls_wR_factor_gt 0.0858 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _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 0.6667 0.16549(3) 0.0833 0.0869(2) Uani 1 2 d S . . C1 C 0.6667 0.2657(4) 0.0833 0.075(2) Uani 1 2 d S . . C2 C 0.6021(5) 0.2687(5) 0.0833 0.074(2) Uani 1 2 d S . . F1 F 0.5379(2) 0.2046(2) 0.0833 0.106(2) Uani 1 2 d S . . I2 I 0.83404(3) 0.33295(3) 0.22418(2) 0.0947(2) Uani 1 1 d . . . C3 C 0.6669(4) 0.2684(4) 0.2185(3) 0.086(2) Uani 1 1 d . . . C4 C 0.7338(4) 0.3336(4) 0.2182(3) 0.085(2) Uani 1 1 d . . . F2 F 0.6665(2) 0.2040(2) 0.2196(2) 0.1159(17) Uani 1 1 d . . . I3 I 1.0000 0.33938(3) 0.2500 0.07350(19) Uani 1 2 d S . . P1 P 0.6252(2) 0.0000 0.2500 0.0674(16) Uani 0.358(9) 2 d SP . 1 C5 C 0.5925(4) 0.0234(5) 0.2051(3) 0.095(2) Uani 1 1 d . . 1 H5A H 0.5908 0.0674 0.2141 0.114 Uiso 1 1 calc R . 1 H5B H 0.6266 0.0365 0.1781 0.114 Uiso 1 1 calc R . 1 C6 C 0.5177(4) -0.0333(6) 0.1881(3) 0.115(3) Uani 1 1 d . . 1 H6A H 0.5034 -0.0140 0.1612 0.172 Uiso 1 1 calc R . 1 H6B H 0.4827 -0.0455 0.2140 0.172 Uiso 1 1 calc R . 1 H6C H 0.5186 -0.0768 0.1781 0.172 Uiso 1 1 calc R . 1 C7 C 0.7024(4) 0.0694(5) 0.2650(3) 0.101(2) Uani 1 1 d . . 1 H7A H 0.6946 0.1104 0.2723 0.122 Uiso 1 1 calc R . 1 H7B H 0.7193 0.0573 0.2945 0.122 Uiso 1 1 calc R . 1 C8 C 0.7631(5) 0.0945(6) 0.2273(4) 0.124(3) Uani 1 1 d . . 1 H8A H 0.8068 0.1374 0.2390 0.186 Uiso 1 1 calc R . 1 H8B H 0.7472 0.1067 0.1978 0.186 Uiso 1 1 calc R . 1 H8C H 0.7738 0.0556 0.2213 0.186 Uiso 1 1 calc R . 1 N1 N 0.6252(2) 0.0000 0.2500 0.0674(16) Uani 0.64 2 d SP . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0813(4) 0.0670(3) 0.1173(6) 0.00361(19) 0.0072(4) 0.0406(2) C1 0.076(6) 0.063(4) 0.090(7) 0.001(3) 0.003(5) 0.038(3) C2 0.068(4) 0.068(4) 0.086(6) -0.002(2) 0.002(2) 0.033(4) F1 0.056(2) 0.056(2) 0.183(6) -0.003(2) 0.003(2) 0.012(3) I2 0.0700(3) 0.0776(3) 0.1407(5) -0.0009(3) 0.0145(3) 0.0400(2) C3 0.075(4) 0.069(4) 0.120(6) -0.006(4) -0.002(4) 0.040(4) C4 0.071(4) 0.074(4) 0.111(6) 0.001(4) 0.008(4) 0.037(4) F2 0.082(3) 0.066(2) 0.202(5) -0.020(3) -0.002(3) 0.039(2) I3 0.0719(4) 0.0656(3) 0.0851(4) 0.00807(15) 0.0161(3) 0.03596(19) P1 0.066(2) 0.071(3) 0.067(3) -0.013(2) -0.0065(10) 0.0353(14) C5 0.099(5) 0.113(6) 0.088(5) -0.008(4) 0.005(4) 0.063(5) C6 0.083(5) 0.160(9) 0.095(6) -0.011(6) -0.008(4) 0.056(6) C7 0.098(5) 0.097(6) 0.114(6) -0.018(5) -0.010(5) 0.053(5) C8 0.071(5) 0.130(8) 0.149(8) -0.014(7) 0.006(5) 0.034(5) N1 0.066(2) 0.071(3) 0.067(3) -0.013(2) -0.0065(10) 0.0353(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 2.094(9) . ? C1 C2 1.382(6) 2_655 ? C1 C2 1.382(6) . ? C2 F1 1.341(10) . ? C2 C1 1.382(6) 3_665 ? I2 C4 2.107(7) . ? C3 F2 1.342(8) . ? C3 C4 1.379(9) 3_665 ? C3 C4 1.381(9) . ? C4 C3 1.379(9) 2_655 ? P1 C7 1.592(8) . ? P1 C7 1.592(8) 4 ? P1 C5 1.605(8) . ? P1 C5 1.605(8) 4 ? C5 C6 1.488(10) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.517(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C2 115.5(10) 2_655 . ? C2 C1 I1 122.3(5) 2_655 . ? C2 C1 I1 122.3(5) . . ? F1 C2 C1 117.7(5) . 3_665 ? F1 C2 C1 117.7(5) . . ? C1 C2 C1 124.5(10) 3_665 . ? F2 C3 C4 118.0(7) . 3_665 ? F2 C3 C4 119.1(7) . . ? C4 C3 C4 122.9(8) 3_665 . ? C3 C4 C3 117.1(8) 2_655 . ? C3 C4 I2 121.9(6) 2_655 . ? C3 C4 I2 120.8(6) . . ? C7 P1 C7 112.2(7) . 4 ? C7 P1 C5 108.4(4) . . ? C7 P1 C5 109.2(4) 4 . ? C7 P1 C5 109.2(4) . 4 ? C7 P1 C5 108.4(4) 4 4 ? C5 P1 C5 109.4(6) . 4 ? C6 C5 P1 116.0(7) . . ? C6 C5 H5A 108.3 . . ? P1 C5 H5A 108.3 . . ? C6 C5 H5B 108.3 . . ? P1 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 P1 115.3(7) . . ? C8 C7 H7A 108.4 . . ? P1 C7 H7A 108.4 . . ? C8 C7 H7B 108.4 . . ? P1 C7 H7B 108.4 . . ? H7A C7 H7B 107.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C2 F1 180.0 2_655 . . . ? I1 C1 C2 F1 0.0 . . . . ? C2 C1 C2 C1 0.0 2_655 . . 3_665 ? I1 C1 C2 C1 180.0 . . . 3_665 ? F2 C3 C4 C3 -178.1(5) . . . 2_655 ? C4 C3 C4 C3 1.5(18) 3_665 . . 2_655 ? F2 C3 C4 I2 -4.3(12) . . . . ? C4 C3 C4 I2 175.3(5) 3_665 . . . ? C7 P1 C5 C6 -176.0(7) . . . . ? C7 P1 C5 C6 61.4(8) 4 . . . ? C5 P1 C5 C6 -57.0(6) 4 . . . ? C7 P1 C7 C8 55.6(6) 4 . . . ? C5 P1 C7 C8 -65.1(8) . . . . ? C5 P1 C7 C8 175.8(7) 4 . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.09 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.270 _refine_diff_density_min -1.226 _refine_diff_density_rms 0.105 # Attachment '18.CIF' data_re229 _database_code_depnum_ccdc_archive 'CCDC 665602' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '0.73(C8 H20 P 1+), 0.27(C8 H20 N 1+), C6 F3 I3, I 1-' _chemical_formula_sum 'C14 H20 F3 I4 N0.27 P0.73' _chemical_formula_weight 779.28 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' F F 0.0171 0.0103 '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' P P 0.1023 0.0942 '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 trigonal _symmetry_space_group_name_H-M R-3c _symmetry_space_group_name_Hall '-R 3 2"c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'y, x, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'y+2/3, x+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' 'y+1/3, x+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-y, -x, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-y+2/3, -x+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' '-y+1/3, -x+2/3, z+1/6' _cell_length_a 20.908(3) _cell_length_b 20.908 _cell_length_c 27.918(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 10569(2) _cell_formula_units_Z 18 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6062 _cell_measurement_theta_min 3.68 _cell_measurement_theta_max 25.13 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6405 _exptl_absorpt_coefficient_mu 5.374 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker, 1997' _exptl_absorpt_correction_T_min 0.812372 _exptl_absorpt_correction_T_max 1.000000 _exptl_special_details ; Crystals were obtained from a solution containing 1,3,5-trifluoro benzene, tetraethylammonium iodide and tetraethylphosphonium iodide with molecular ratio 1.0:0.7:1.4, respectively. ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\w and \f scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 34978 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 29.08 _reflns_number_total 3104 _reflns_number_gt 1767 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna (2003). SIR2002: the program. J. Appl. Cryst. 36,1103 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. P1 and N1 atoms were constrained to have the same coordinates and ADPs. No attempt was made to split carbon atoms of tetraethylphosphonium and tetraethylammonium ions. Anomalous P-C, N-C, C-C distances and ADPs of the atom of the cations are due to this bias. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+94.8972P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3104 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0822 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.6667 0.16563(3) 0.0833 0.0848(2) Uani 1 2 d S . . C1 C 0.6667 0.2662(4) 0.0833 0.072(2) Uani 1 2 d S . . C2 C 0.6019(4) 0.2686(4) 0.0833 0.072(2) Uani 1 2 d S . . F1 F 0.5383(2) 0.2050(2) 0.0833 0.1007(18) Uani 1 2 d S . . I2 I 0.83402(2) 0.33324(2) 0.22307(2) 0.09169(18) Uani 1 1 d . . . C3 C 0.6665(4) 0.2681(4) 0.2171(3) 0.0823(19) Uani 1 1 d . . . C4 C 0.7337(4) 0.3336(3) 0.2168(3) 0.0802(18) Uani 1 1 d . . . F2 F 0.6666(2) 0.2043(2) 0.21813(18) 0.1114(15) Uani 1 1 d . . . I3 I 1.0000 0.34002(3) 0.2500 0.07443(18) Uani 1 2 d S . . P1 P 0.62615(13) 0.0000 0.2500 0.0681(10) Uani 0.730(8) 2 d SP . 1 C5 C 0.5894(4) 0.0222(4) 0.2023(3) 0.098(2) Uani 1 1 d . . 1 H5A H 0.5865 0.0657 0.2107 0.117 Uiso 1 1 calc R . 1 H5B H 0.6232 0.0353 0.1755 0.117 Uiso 1 1 calc R . 1 C6 C 0.5153(4) -0.0362(5) 0.1864(3) 0.121(3) Uani 1 1 d . . 1 H6A H 0.4997 -0.0185 0.1596 0.182 Uiso 1 1 calc R . 1 H6B H 0.4807 -0.0486 0.2121 0.182 Uiso 1 1 calc R . 1 H6C H 0.5175 -0.0792 0.1770 0.182 Uiso 1 1 calc R . 1 C7 C 0.7085(4) 0.0746(4) 0.2645(3) 0.107(2) Uani 1 1 d . . 1 H7A H 0.7008 0.1157 0.2715 0.128 Uiso 1 1 calc R . 1 H7B H 0.7269 0.0636 0.2934 0.128 Uiso 1 1 calc R . 1 C8 C 0.7676(4) 0.0983(5) 0.2252(3) 0.129(3) Uani 1 1 d . . 1 H8A H 0.8122 0.1411 0.2357 0.193 Uiso 1 1 calc R . 1 H8B H 0.7503 0.1098 0.1965 0.193 Uiso 1 1 calc R . 1 H8C H 0.7773 0.0587 0.2190 0.193 Uiso 1 1 calc R . 1 N1 N 0.62615(13) 0.0000 0.2500 0.0681(10) Uani 0.27 2 d SP . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0800(4) 0.0667(3) 0.1120(5) 0.00362(17) 0.0072(3) 0.0400(2) C1 0.071(5) 0.064(4) 0.082(6) 0.001(2) 0.003(4) 0.036(3) C2 0.063(3) 0.063(3) 0.087(6) 0.000(2) 0.000(2) 0.027(4) F1 0.0605(19) 0.0605(19) 0.166(5) -0.0042(18) 0.0042(18) 0.019(2) I2 0.0679(3) 0.0761(3) 0.1350(4) -0.0014(3) 0.0142(2) 0.0390(2) C3 0.074(4) 0.070(4) 0.106(5) -0.009(3) -0.001(4) 0.039(3) C4 0.071(4) 0.068(4) 0.103(5) 0.003(3) 0.008(3) 0.035(3) F2 0.079(2) 0.064(2) 0.194(5) -0.020(3) -0.001(3) 0.0379(19) I3 0.0690(3) 0.0649(3) 0.0907(4) 0.00820(15) 0.0164(3) 0.03450(17) P1 0.0650(14) 0.0723(19) 0.0693(18) -0.0137(13) -0.0068(7) 0.0362(9) C5 0.095(5) 0.114(6) 0.095(5) -0.001(4) 0.007(4) 0.061(5) C6 0.087(5) 0.167(8) 0.104(6) -0.009(6) -0.008(4) 0.059(6) C7 0.102(5) 0.101(6) 0.122(6) -0.021(5) -0.015(5) 0.055(5) C8 0.078(5) 0.132(7) 0.158(8) -0.010(6) 0.020(5) 0.039(5) N1 0.0650(14) 0.0723(19) 0.0693(18) -0.0137(13) -0.0068(7) 0.0362(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 2.103(8) . ? C1 C2 1.379(5) . ? C1 C2 1.379(5) 2_655 ? C2 F1 1.330(9) . ? C2 C1 1.379(5) 3_665 ? I2 C4 2.109(7) . ? C3 F2 1.336(7) . ? C3 C4 1.373(8) 3_665 ? C3 C4 1.388(8) . ? C4 C3 1.373(8) 2_655 ? P1 C7 1.696(8) . ? P1 C7 1.696(8) 4 ? P1 C5 1.712(8) . ? P1 C5 1.712(8) 4 ? C5 C6 1.483(10) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.536(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C2 116.4(9) . 2_655 ? C2 C1 I1 121.8(5) . . ? C2 C1 I1 121.8(5) 2_655 . ? F1 C2 C1 118.2(5) . . ? F1 C2 C1 118.2(5) . 3_665 ? C1 C2 C1 123.6(9) . 3_665 ? F2 C3 C4 118.7(6) . 3_665 ? F2 C3 C4 118.6(6) . . ? C4 C3 C4 122.7(7) 3_665 . ? C3 C4 C3 117.3(7) 2_655 . ? C3 C4 I2 121.4(5) 2_655 . ? C3 C4 I2 120.9(5) . . ? C7 P1 C7 112.5(6) . 4 ? C7 P1 C5 108.8(4) . . ? C7 P1 C5 109.0(4) 4 . ? C7 P1 C5 109.0(4) . 4 ? C7 P1 C5 108.8(4) 4 4 ? C5 P1 C5 108.6(5) . 4 ? C6 C5 P1 115.9(6) . . ? C6 C5 H5A 108.3 . . ? P1 C5 H5A 108.3 . . ? C6 C5 H5B 108.3 . . ? P1 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 P1 114.2(6) . . ? C8 C7 H7A 108.7 . . ? P1 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? P1 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C1 C2 F1 180.0 2_655 . . . ? I1 C1 C2 F1 0.0 . . . . ? C2 C1 C2 C1 0.0 2_655 . . 3_665 ? I1 C1 C2 C1 180.0 . . . 3_665 ? F2 C3 C4 C3 -178.2(4) . . . 2_655 ? C4 C3 C4 C3 1.0(16) 3_665 . . 2_655 ? F2 C3 C4 I2 -4.4(10) . . . . ? C4 C3 C4 I2 174.8(4) 3_665 . . . ? C7 P1 C5 C6 -177.3(6) . . . . ? C7 P1 C5 C6 59.7(7) 4 . . . ? C5 P1 C5 C6 -58.8(5) 4 . . . ? C7 P1 C7 C8 56.8(6) 4 . . . ? C5 P1 C7 C8 -64.1(8) . . . . ? C5 P1 C7 C8 177.6(6) 4 . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.059 _refine_diff_density_min -1.103 _refine_diff_density_rms 0.095