# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tw1239mA4D3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; TW-6-27 pyridine N-oxide, 1,3,5-F3-2,4,6-I3-benzene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C5 H5 N O) (C6 F3 I3) ; _chemical_formula_sum 'C11 H5 F3 I3 N O' _chemical_formula_weight 604.86 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' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.4824(12) _cell_length_b 7.3041(7) _cell_length_c 15.4872(16) _cell_angle_alpha 90.00 _cell_angle_beta 97.536(3) _cell_angle_gamma 90.00 _cell_volume 1399.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9938 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 32.53 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.870 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 6.723 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1559 _exptl_absorpt_correction_T_max 0.3775 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13950 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 32.54 _reflns_number_total 4568 _reflns_number_gt 4343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0150P)^2^+1.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4568 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0267 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0586 _refine_ls_wR_factor_gt 0.0578 _refine_ls_goodness_of_fit_ref 1.210 _refine_ls_restrained_S_all 1.210 _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 N11 N 0.44356(19) 0.6359(3) 0.36734(15) 0.0144(4) Uani 1 1 d . . . O11 O 0.42238(16) 0.4574(3) 0.36058(13) 0.0178(4) Uani 1 1 d . . . C12 C 0.3680(2) 0.7579(4) 0.33838(19) 0.0195(5) Uani 1 1 d . . . H12 H 0.2990 0.7173 0.3122 0.023 Uiso 1 1 calc R . . C13 C 0.3891(2) 0.9418(4) 0.3461(2) 0.0221(6) Uani 1 1 d . . . H13 H 0.3343 1.0279 0.3261 0.026 Uiso 1 1 calc R . . C14 C 0.4895(3) 1.0025(4) 0.38265(19) 0.0229(6) Uani 1 1 d . . . H14 H 0.5047 1.1297 0.3884 0.028 Uiso 1 1 calc R . . C15 C 0.5675(3) 0.8735(4) 0.4108(2) 0.0262(6) Uani 1 1 d . . . H15 H 0.6377 0.9113 0.4355 0.031 Uiso 1 1 calc R . . C16 C 0.5427(2) 0.6897(4) 0.4029(2) 0.0209(5) Uani 1 1 d . . . H16 H 0.5959 0.6008 0.4225 0.025 Uiso 1 1 calc R . . C21 C 0.4658(2) 0.2993(3) 0.06417(17) 0.0139(4) Uani 1 1 d . . . I21 I 0.452073(13) 0.36631(2) 0.193651(11) 0.01395(5) Uani 1 1 d . . . C22 C 0.5637(2) 0.2506(3) 0.03737(17) 0.0144(4) Uani 1 1 d . . . F22 F 0.65253(13) 0.2557(3) 0.09614(11) 0.0208(3) Uani 1 1 d . . . C23 C 0.5732(2) 0.1971(3) -0.04686(17) 0.0142(4) Uani 1 1 d . . . I23 I 0.722438(13) 0.13158(2) -0.085752(11) 0.01440(5) Uani 1 1 d . . . C24 C 0.4798(2) 0.1910(4) -0.10518(17) 0.0144(4) Uani 1 1 d . . . F24 F 0.48605(14) 0.1357(2) -0.18686(11) 0.0192(3) Uani 1 1 d . . . C25 C 0.3801(2) 0.2403(3) -0.08340(17) 0.0142(4) Uani 1 1 d . . . I25 I 0.242481(14) 0.22730(3) -0.174351(12) 0.02081(5) Uani 1 1 d . . . C26 C 0.3761(2) 0.2970(3) 0.00126(18) 0.0143(4) Uani 1 1 d . . . F26 F 0.28060(13) 0.3490(2) 0.02376(11) 0.0186(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0173(10) 0.0148(10) 0.0114(10) -0.0016(7) 0.0035(8) 0.0003(7) O11 0.0201(9) 0.0143(8) 0.0192(9) -0.0025(7) 0.0040(7) -0.0029(7) C12 0.0145(11) 0.0233(13) 0.0211(13) 0.0040(11) 0.0040(10) 0.0020(9) C13 0.0216(13) 0.0212(13) 0.0241(14) 0.0037(11) 0.0058(11) 0.0034(10) C14 0.0339(15) 0.0167(12) 0.0187(13) -0.0008(10) 0.0055(12) -0.0033(11) C15 0.0269(14) 0.0215(14) 0.0277(16) -0.0017(11) -0.0052(12) -0.0071(11) C16 0.0194(12) 0.0174(12) 0.0237(14) 0.0000(11) -0.0052(10) 0.0021(10) C21 0.0164(11) 0.0141(10) 0.0113(11) 0.0001(9) 0.0018(9) 0.0000(9) I21 0.01625(8) 0.01431(8) 0.01127(8) -0.00062(5) 0.00172(6) -0.00042(5) C22 0.0162(11) 0.0152(11) 0.0113(11) 0.0000(9) 0.0000(9) -0.0007(9) F22 0.0145(7) 0.0309(9) 0.0159(8) -0.0031(7) -0.0019(6) 0.0017(6) C23 0.0145(10) 0.0146(11) 0.0140(11) -0.0001(9) 0.0037(9) 0.0000(9) I23 0.01284(8) 0.01529(8) 0.01524(9) 0.00028(5) 0.00245(6) 0.00065(5) C24 0.0168(11) 0.0128(10) 0.0134(11) -0.0012(9) 0.0015(9) -0.0005(9) F24 0.0182(7) 0.0260(9) 0.0133(8) -0.0052(6) 0.0021(6) 0.0015(6) C25 0.0145(10) 0.0147(10) 0.0129(11) -0.0001(9) 0.0002(9) -0.0004(8) I25 0.01661(8) 0.02687(10) 0.01726(9) -0.00201(7) -0.00413(6) 0.00266(6) C26 0.0133(10) 0.0144(11) 0.0158(12) 0.0008(9) 0.0040(9) 0.0012(8) F26 0.0134(7) 0.0247(8) 0.0181(8) -0.0007(6) 0.0034(6) 0.0044(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 O11 1.332(3) . ? N11 C12 1.332(4) . ? N11 C16 1.346(4) . ? O11 I21 2.7413(19) . ? C12 C13 1.371(4) . ? C12 H12 0.9500 . ? C13 C14 1.379(4) . ? C13 H13 0.9500 . ? C14 C15 1.383(5) . ? C14 H14 0.9500 . ? C15 C16 1.379(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.384(4) . ? C21 C22 1.387(3) . ? C21 I21 2.093(2) . ? I21 I25 3.9804(4) 4_666 ? C22 F22 1.340(3) . ? C22 C23 1.382(3) . ? C23 C24 1.379(4) . ? C23 I23 2.087(2) . ? I23 O11 2.8082(19) 4_665 ? C24 F24 1.340(3) . ? C24 C25 1.379(3) . ? C25 C26 1.382(4) . ? C25 I25 2.076(3) . ? C26 F26 1.340(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 N11 C12 120.3(2) . . ? O11 N11 C16 118.7(2) . . ? C12 N11 C16 121.0(2) . . ? N11 O11 I21 105.17(14) . . ? N11 C12 C13 120.5(3) . . ? N11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C14 120.3(3) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C15 118.3(3) . . ? C13 C14 H14 120.8 . . ? C15 C14 H14 120.8 . . ? C16 C15 C14 119.7(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? N11 C16 C15 120.3(3) . . ? N11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C26 C21 C22 116.7(2) . . ? C26 C21 I21 121.11(17) . . ? C22 C21 I21 122.2(2) . . ? C21 I21 O11 176.90(8) . . ? C21 I21 I25 105.57(7) . 4_666 ? O11 I21 I25 77.52(4) . 4_666 ? F22 C22 C23 118.9(2) . . ? F22 C22 C21 118.2(2) . . ? C23 C22 C21 122.9(2) . . ? C24 C23 C22 117.2(2) . . ? C24 C23 I23 120.92(18) . . ? C22 C23 I23 121.9(2) . . ? C23 I23 O11 179.54(9) . 4_665 ? F24 C24 C25 118.4(2) . . ? F24 C24 C23 118.6(2) . . ? C25 C24 C23 123.0(2) . . ? C24 C25 C26 117.1(2) . . ? C24 C25 I25 120.99(19) . . ? C26 C25 I25 121.88(18) . . ? F26 C26 C25 118.4(2) . . ? F26 C26 C21 118.6(2) . . ? C25 C26 C21 123.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 N11 O11 I21 82.4(2) . . . . ? C16 N11 O11 I21 -96.8(2) . . . . ? O11 N11 C12 C13 179.3(2) . . . . ? C16 N11 C12 C13 -1.5(4) . . . . ? N11 C12 C13 C14 1.1(4) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? C13 C14 C15 C16 -0.9(5) . . . . ? O11 N11 C16 C15 179.9(3) . . . . ? C12 N11 C16 C15 0.7(4) . . . . ? C14 C15 C16 N11 0.5(5) . . . . ? C26 C21 I21 O11 -2.4(16) . . . . ? C22 C21 I21 O11 179(31) . . . . ? C26 C21 I21 I25 173.02(19) . . . 4_666 ? C22 C21 I21 I25 -5.3(2) . . . 4_666 ? N11 O11 I21 C21 -92.9(15) . . . . ? N11 O11 I21 I25 91.60(15) . . . 4_666 ? C26 C21 C22 F22 178.4(2) . . . . ? I21 C21 C22 F22 -3.2(3) . . . . ? C26 C21 C22 C23 -1.8(4) . . . . ? I21 C21 C22 C23 176.64(19) . . . . ? F22 C22 C23 C24 179.0(2) . . . . ? C21 C22 C23 C24 -0.8(4) . . . . ? F22 C22 C23 I23 -1.8(3) . . . . ? C21 C22 C23 I23 178.33(19) . . . . ? C24 C23 I23 O11 -4(11) . . . 4_665 ? C22 C23 I23 O11 177(100) . . . 4_665 ? C22 C23 C24 F24 -178.5(2) . . . . ? I23 C23 C24 F24 2.3(3) . . . . ? C22 C23 C24 C25 1.9(4) . . . . ? I23 C23 C24 C25 -177.2(2) . . . . ? F24 C24 C25 C26 -179.9(2) . . . . ? C23 C24 C25 C26 -0.3(4) . . . . ? F24 C24 C25 I25 0.5(3) . . . . ? C23 C24 C25 I25 -179.86(19) . . . . ? C24 C25 C26 F26 178.8(2) . . . . ? I25 C25 C26 F26 -1.7(3) . . . . ? C24 C25 C26 C21 -2.5(4) . . . . ? I25 C25 C26 C21 177.06(19) . . . . ? C22 C21 C26 F26 -177.8(2) . . . . ? I21 C21 C26 F26 3.8(3) . . . . ? C22 C21 C26 C25 3.5(4) . . . . ? I21 C21 C26 C25 -175.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.854 _refine_diff_density_min -1.792 _refine_diff_density_rms 0.247 _database_code_depnum_ccdc_archive 'CCDC 953680' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tw1246mA5D1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; TW-6-33 4-methylpyridine-N-oxide, 1,2-diiodotetrafluorobenzene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C6 H7 N O) (C6 F4 I2) ; _chemical_formula_sum 'C12 H7 F4 I2 N O' _chemical_formula_weight 510.99 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9400(5) _cell_length_b 8.5688(6) _cell_length_c 11.5503(8) _cell_angle_alpha 89.243(2) _cell_angle_beta 83.738(2) _cell_angle_gamma 65.570(2) _cell_volume 710.77(8) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9047 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 32.65 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 4.463 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2558 _exptl_absorpt_correction_T_max 0.5354 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11235 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 32.57 _reflns_number_total 4521 _reflns_number_gt 4212 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+1.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4521 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0753 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 N11 N 0.6361(3) 0.2642(3) 0.10518(18) 0.0217(4) Uani 1 1 d . . . O11 O 0.5634(3) 0.4243(2) 0.14714(17) 0.0280(4) Uani 1 1 d . . . C12 C 0.6170(4) 0.2325(4) -0.0052(2) 0.0273(5) Uani 1 1 d . . . H12 H 0.5507 0.3244 -0.0523 0.033 Uiso 1 1 calc R . . C13 C 0.6936(5) 0.0668(4) -0.0496(3) 0.0330(6) Uani 1 1 d . . . H13 H 0.6787 0.0456 -0.1275 0.040 Uiso 1 1 calc R . . C14 C 0.7922(4) -0.0701(4) 0.0164(3) 0.0307(6) Uani 1 1 d . . . C17 C 0.8788(6) -0.2517(4) -0.0321(4) 0.0472(9) Uani 1 1 d . . . H17A H 0.9055 -0.2516 -0.1170 0.071 Uiso 1 1 calc R . . H17B H 0.7925 -0.3057 -0.0128 0.071 Uiso 1 1 calc R . . H17C H 0.9949 -0.3160 0.0018 0.071 Uiso 1 1 calc R . . C15 C 0.8078(4) -0.0310(4) 0.1295(3) 0.0325(6) Uani 1 1 d . . . H15 H 0.8742 -0.1207 0.1782 0.039 Uiso 1 1 calc R . . C16 C 0.7291(4) 0.1349(4) 0.1726(2) 0.0289(5) Uani 1 1 d . . . H16 H 0.7403 0.1588 0.2507 0.035 Uiso 1 1 calc R . . C21 C -0.0096(4) 0.6931(3) 0.4133(2) 0.0209(4) Uani 1 1 d . . . I1 I 0.21435(2) 0.56805(2) 0.285933(14) 0.02406(6) Uani 1 1 d . . . C22 C -0.1866(4) 0.6947(3) 0.4152(2) 0.0217(4) Uani 1 1 d . . . I2 I -0.26692(2) 0.56980(2) 0.292190(14) 0.02390(6) Uani 1 1 d . . . C23 C -0.3209(4) 0.7814(4) 0.5070(2) 0.0241(5) Uani 1 1 d . . . F23 F -0.4915(2) 0.7864(3) 0.51361(17) 0.0344(4) Uani 1 1 d . . . C24 C -0.2837(4) 0.8650(3) 0.5950(2) 0.0249(5) Uani 1 1 d . . . F24 F -0.4151(3) 0.9464(3) 0.68269(15) 0.0360(4) Uani 1 1 d . . . C25 C -0.1106(4) 0.8637(3) 0.5928(2) 0.0244(5) Uani 1 1 d . . . F25 F -0.0725(3) 0.9437(2) 0.67832(15) 0.0340(4) Uani 1 1 d . . . C26 C 0.0243(4) 0.7779(4) 0.5027(2) 0.0231(5) Uani 1 1 d . . . F26 F 0.1909(3) 0.7812(3) 0.50489(16) 0.0320(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0190(10) 0.0215(9) 0.0233(9) -0.0040(8) -0.0014(7) -0.0071(8) O11 0.0310(10) 0.0196(8) 0.0300(9) -0.0071(7) -0.0048(7) -0.0065(7) C12 0.0344(15) 0.0235(12) 0.0214(10) -0.0002(9) -0.0040(9) -0.0092(11) C13 0.0440(18) 0.0269(13) 0.0242(12) -0.0070(10) -0.0001(11) -0.0115(12) C14 0.0312(15) 0.0180(11) 0.0381(14) -0.0041(10) 0.0061(11) -0.0077(10) C17 0.056(2) 0.0235(14) 0.053(2) -0.0095(14) 0.0109(17) -0.0106(14) C15 0.0333(15) 0.0238(12) 0.0358(14) 0.0032(11) -0.0046(11) -0.0071(11) C16 0.0335(15) 0.0262(12) 0.0265(11) 0.0019(10) -0.0080(10) -0.0107(11) C21 0.0202(11) 0.0182(10) 0.0241(10) 0.0011(8) -0.0035(8) -0.0075(8) I1 0.02120(10) 0.01939(9) 0.02871(9) -0.00007(6) -0.00056(6) -0.00606(7) C22 0.0217(12) 0.0206(10) 0.0245(10) 0.0008(8) -0.0050(8) -0.0099(9) I2 0.02471(10) 0.02093(9) 0.02738(9) -0.00159(6) -0.00697(6) -0.00975(7) C23 0.0218(12) 0.0260(12) 0.0270(11) 0.0012(10) -0.0047(9) -0.0119(10) F23 0.0194(8) 0.0462(11) 0.0384(9) -0.0081(8) -0.0004(7) -0.0148(8) C24 0.0214(12) 0.0266(12) 0.0246(11) -0.0009(9) -0.0010(8) -0.0082(10) F24 0.0286(9) 0.0454(10) 0.0319(8) -0.0125(8) 0.0060(7) -0.0151(8) C25 0.0278(13) 0.0228(11) 0.0252(11) -0.0010(9) -0.0076(9) -0.0121(10) F25 0.0366(10) 0.0406(10) 0.0306(8) -0.0076(7) -0.0074(7) -0.0207(8) C26 0.0200(12) 0.0230(11) 0.0281(11) 0.0033(9) -0.0067(9) -0.0098(9) F26 0.0249(9) 0.0388(10) 0.0385(9) -0.0019(8) -0.0060(7) -0.0187(8) _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 N11 O11 1.324(3) . ? N11 C16 1.343(3) . ? N11 C12 1.344(3) . ? O11 I1 2.833(2) . ? C12 C13 1.373(4) . ? C12 H12 0.9500 . ? C13 C14 1.384(5) . ? C13 H13 0.9500 . ? C14 C15 1.384(4) . ? C14 C17 1.504(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C15 C16 1.369(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.381(4) . ? C21 C22 1.398(3) . ? C21 I1 2.090(2) . ? C22 C23 1.390(4) . ? C22 I2 2.091(2) . ? I2 O11 2.848(2) 1_455 ? C23 F23 1.331(3) . ? C23 C24 1.377(4) . ? C24 F24 1.337(3) . ? C24 C25 1.367(4) . ? C25 F25 1.338(3) . ? C25 C26 1.377(4) . ? C26 F26 1.338(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 N11 C16 120.0(2) . . ? O11 N11 C12 119.5(2) . . ? C16 N11 C12 120.5(2) . . ? N11 O11 I1 122.02(15) . . ? N11 C12 C13 119.8(3) . . ? N11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 121.6(3) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C15 C14 C13 116.4(3) . . ? C15 C14 C17 121.7(3) . . ? C13 C14 C17 121.9(3) . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C15 C14 121.1(3) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? N11 C16 C15 120.6(3) . . ? N11 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C26 C21 C22 118.6(2) . . ? C26 C21 I1 116.24(19) . . ? C22 C21 I1 125.17(18) . . ? C21 I1 O11 166.68(8) . . ? C23 C22 C21 118.6(2) . . ? C23 C22 I2 116.19(18) . . ? C21 C22 I2 125.21(18) . . ? C22 I2 O11 170.30(8) . 1_455 ? F23 C23 C24 117.1(2) . . ? F23 C23 C22 121.2(2) . . ? C24 C23 C22 121.7(2) . . ? F24 C24 C25 119.9(2) . . ? F24 C24 C23 120.5(2) . . ? C25 C24 C23 119.6(2) . . ? F25 C25 C24 120.1(2) . . ? F25 C25 C26 120.5(2) . . ? C24 C25 C26 119.4(2) . . ? F26 C26 C25 116.8(2) . . ? F26 C26 C21 121.1(2) . . ? C25 C26 C21 122.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 O11 I1 -82.3(3) . . . . ? C12 N11 O11 I1 98.1(2) . . . . ? O11 N11 C12 C13 179.4(3) . . . . ? C16 N11 C12 C13 -0.2(4) . . . . ? N11 C12 C13 C14 -0.5(5) . . . . ? C12 C13 C14 C15 0.6(5) . . . . ? C12 C13 C14 C17 -179.1(3) . . . . ? C13 C14 C15 C16 0.0(5) . . . . ? C17 C14 C15 C16 179.7(3) . . . . ? O11 N11 C16 C15 -178.8(3) . . . . ? C12 N11 C16 C15 0.8(4) . . . . ? C14 C15 C16 N11 -0.7(5) . . . . ? C26 C21 I1 O11 3.4(5) . . . . ? C22 C21 I1 O11 -175.6(2) . . . . ? N11 O11 I1 C21 132.3(3) . . . . ? C26 C21 C22 C23 -0.1(4) . . . . ? I1 C21 C22 C23 178.92(19) . . . . ? C26 C21 C22 I2 -178.17(19) . . . . ? I1 C21 C22 I2 0.8(3) . . . . ? C23 C22 I2 O11 3.4(6) . . . 1_455 ? C21 C22 I2 O11 -178.5(3) . . . 1_455 ? C21 C22 C23 F23 -179.6(2) . . . . ? I2 C22 C23 F23 -1.4(3) . . . . ? C21 C22 C23 C24 0.1(4) . . . . ? I2 C22 C23 C24 178.4(2) . . . . ? F23 C23 C24 F24 0.2(4) . . . . ? C22 C23 C24 F24 -179.5(2) . . . . ? F23 C23 C24 C25 179.8(2) . . . . ? C22 C23 C24 C25 0.1(4) . . . . ? F24 C24 C25 F25 0.0(4) . . . . ? C23 C24 C25 F25 -179.6(2) . . . . ? F24 C24 C25 C26 179.3(2) . . . . ? C23 C24 C25 C26 -0.3(4) . . . . ? F25 C25 C26 F26 -0.8(4) . . . . ? C24 C25 C26 F26 179.9(2) . . . . ? F25 C25 C26 C21 179.7(2) . . . . ? C24 C25 C26 C21 0.3(4) . . . . ? C22 C21 C26 F26 -179.7(2) . . . . ? I1 C21 C26 F26 1.2(3) . . . . ? C22 C21 C26 C25 -0.1(4) . . . . ? I1 C21 C26 C25 -179.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.874 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 2.286 _refine_diff_density_min -0.812 _refine_diff_density_rms 0.152 _database_code_depnum_ccdc_archive 'CCDC 953681' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tw1322mA6D1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; TW-6-37 3-methylpyridine-N-oxide, 1,2-diiodotetrafluorobenzene ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C6 H7 N O) (C6 F4 I2) ; _chemical_formula_sum 'C12 H7 F4 I2 N O' _chemical_formula_weight 510.99 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' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.8713(9) _cell_length_b 23.203(3) _cell_length_c 7.8169(9) _cell_angle_alpha 90.00 _cell_angle_beta 92.019(4) _cell_angle_gamma 90.00 _cell_volume 1426.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9941 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 32.55 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 4.447 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3132 _exptl_absorpt_correction_T_max 0.4700 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16697 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 32.66 _reflns_number_total 5006 _reflns_number_gt 4805 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0150P)^2^+1.5000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5006 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0505 _refine_ls_wR_factor_gt 0.0499 _refine_ls_goodness_of_fit_ref 1.186 _refine_ls_restrained_S_all 1.186 _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 N11 N 0.5755(2) 0.69233(8) -0.0516(2) 0.0213(3) Uani 1 1 d . . . O11 O 0.4824(2) 0.64826(7) -0.1035(2) 0.0274(3) Uani 1 1 d . . . C12 C 0.7319(3) 0.68374(10) 0.0197(3) 0.0240(4) Uani 1 1 d . . . H12A H 0.7734 0.6455 0.0329 0.029 Uiso 1 1 calc R . . C13 C 0.8332(3) 0.72921(10) 0.0738(3) 0.0229(4) Uani 1 1 d . . . C14 C 0.7701(3) 0.78487(10) 0.0558(3) 0.0251(4) Uani 1 1 d . . . H14A H 0.8366 0.8170 0.0927 0.030 Uiso 1 1 calc R . . C15 C 0.6093(3) 0.79276(10) -0.0164(3) 0.0274(4) Uani 1 1 d . . . H15A H 0.5647 0.8306 -0.0290 0.033 Uiso 1 1 calc R . . C16 C 0.5133(3) 0.74652(9) -0.0702(3) 0.0247(4) Uani 1 1 d . . . H16A H 0.4031 0.7524 -0.1206 0.030 Uiso 1 1 calc R . . C17 C 1.0075(3) 0.71763(13) 0.1492(4) 0.0353(5) Uani 1 1 d . . . H17A H 1.0012 0.6872 0.2357 0.053 Uiso 1 1 calc R . . H17B H 1.0530 0.7529 0.2025 0.053 Uiso 1 1 calc R . . H17C H 1.0822 0.7052 0.0586 0.053 Uiso 1 1 calc R . . C21 C 0.2611(3) 0.56056(9) 0.4087(3) 0.0199(4) Uani 1 1 d . . . I1 I 0.354225(17) 0.595095(6) 0.182268(17) 0.01985(4) Uani 1 1 d . . . C22 C 0.2624(2) 0.50135(9) 0.4446(3) 0.0198(4) Uani 1 1 d . . . I2 I 0.361629(16) 0.439532(5) 0.280712(17) 0.01953(4) Uani 1 1 d . . . C23 C 0.2014(3) 0.48280(11) 0.5988(3) 0.0250(4) Uani 1 1 d . . . F23 F 0.1977(2) 0.42620(7) 0.6381(2) 0.0336(3) Uani 1 1 d . . . C24 C 0.1405(3) 0.52083(13) 0.7181(3) 0.0299(5) Uani 1 1 d . . . F24 F 0.0827(2) 0.50107(9) 0.86515(19) 0.0435(4) Uani 1 1 d . . . C25 C 0.1395(3) 0.57907(12) 0.6830(3) 0.0283(5) Uani 1 1 d . . . F25 F 0.07983(19) 0.61676(8) 0.7962(2) 0.0388(4) Uani 1 1 d . . . C26 C 0.1996(3) 0.59796(10) 0.5289(3) 0.0239(4) Uani 1 1 d . . . F26 F 0.19630(19) 0.65545(6) 0.5010(2) 0.0322(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0272(9) 0.0174(8) 0.0195(8) -0.0004(6) 0.0035(6) -0.0007(6) O11 0.0332(9) 0.0209(7) 0.0283(8) -0.0034(6) 0.0021(6) -0.0064(6) C12 0.0280(10) 0.0198(9) 0.0241(9) 0.0012(8) 0.0010(8) 0.0055(8) C13 0.0249(10) 0.0228(9) 0.0209(9) 0.0012(8) 0.0003(7) 0.0041(8) C14 0.0274(10) 0.0185(9) 0.0294(10) -0.0019(8) -0.0007(8) 0.0007(8) C15 0.0314(11) 0.0175(9) 0.0330(11) -0.0009(8) -0.0042(9) 0.0041(8) C16 0.0255(10) 0.0213(9) 0.0270(10) 0.0003(8) -0.0018(8) 0.0045(8) C17 0.0294(12) 0.0387(13) 0.0373(13) 0.0006(11) -0.0071(10) 0.0078(10) C21 0.0168(8) 0.0255(10) 0.0172(8) -0.0002(7) -0.0016(6) 0.0007(7) I1 0.02120(6) 0.01812(6) 0.02011(6) -0.00043(4) -0.00076(4) -0.00008(4) C22 0.0159(8) 0.0254(9) 0.0182(8) 0.0001(7) -0.0008(6) 0.0000(7) I2 0.01922(6) 0.01784(6) 0.02135(6) 0.00013(4) -0.00176(4) -0.00197(4) C23 0.0185(9) 0.0348(12) 0.0214(9) 0.0059(9) -0.0019(7) -0.0037(8) F23 0.0320(8) 0.0374(8) 0.0314(7) 0.0120(6) 0.0020(6) -0.0074(6) C24 0.0182(9) 0.0537(16) 0.0178(9) 0.0016(10) 0.0020(7) -0.0024(9) F24 0.0352(8) 0.0748(12) 0.0212(7) 0.0047(7) 0.0099(6) -0.0068(8) C25 0.0167(9) 0.0460(14) 0.0221(9) -0.0108(10) -0.0011(7) 0.0044(9) F25 0.0266(7) 0.0623(11) 0.0276(7) -0.0175(7) 0.0026(6) 0.0084(7) C26 0.0196(9) 0.0293(11) 0.0226(9) -0.0043(8) -0.0027(7) 0.0055(8) F26 0.0345(8) 0.0283(7) 0.0336(7) -0.0096(6) -0.0026(6) 0.0096(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 O11 1.314(2) . ? N11 C12 1.348(3) . ? N11 C16 1.355(3) . ? O11 I1 2.7729(17) . ? C12 C13 1.380(3) . ? C12 H12A 0.9500 . ? C13 C14 1.389(3) . ? C13 C17 1.498(3) . ? C14 C15 1.380(3) . ? C14 H14A 0.9500 . ? C15 C16 1.370(3) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C21 C26 1.379(3) . ? C21 C22 1.402(3) . ? C21 I1 2.098(2) . ? C22 C23 1.382(3) . ? C22 I2 2.093(2) . ? I2 O11 2.7739(17) 3_665 ? C23 F23 1.349(3) . ? C23 C24 1.382(3) . ? C24 F24 1.332(3) . ? C24 C25 1.379(4) . ? C25 F25 1.341(3) . ? C25 C26 1.382(3) . ? C26 F26 1.352(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 N11 C12 120.25(18) . . ? O11 N11 C16 119.54(19) . . ? C12 N11 C16 120.20(19) . . ? N11 O11 I1 108.18(12) . . ? N11 C12 C13 121.5(2) . . ? N11 C12 H12A 119.2 . . ? C13 C12 H12A 119.2 . . ? C12 C13 C14 118.6(2) . . ? C12 C13 C17 119.6(2) . . ? C14 C13 C17 121.7(2) . . ? C15 C14 C13 119.0(2) . . ? C15 C14 H14A 120.5 . . ? C13 C14 H14A 120.5 . . ? C16 C15 C14 120.7(2) . . ? C16 C15 H15A 119.7 . . ? C14 C15 H15A 119.7 . . ? N11 C16 C15 120.0(2) . . ? N11 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C26 C21 C22 118.71(19) . . ? C26 C21 I1 118.40(16) . . ? C22 C21 I1 122.87(15) . . ? C21 I1 O11 175.73(7) . . ? C23 C22 C21 118.6(2) . . ? C23 C22 I2 117.98(17) . . ? C21 C22 I2 123.31(15) . . ? C22 I2 O11 172.03(7) . 3_665 ? F23 C23 C24 117.2(2) . . ? F23 C23 C22 120.8(2) . . ? C24 C23 C22 122.0(2) . . ? F24 C24 C25 120.6(2) . . ? F24 C24 C23 120.0(3) . . ? C25 C24 C23 119.4(2) . . ? F25 C25 C24 120.5(2) . . ? F25 C25 C26 120.5(2) . . ? C24 C25 C26 119.0(2) . . ? F26 C26 C21 121.1(2) . . ? F26 C26 C25 116.6(2) . . ? C21 C26 C25 122.3(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 N11 O11 I1 75.70(19) . . . . ? C16 N11 O11 I1 -104.37(18) . . . . ? O11 N11 C12 C13 179.33(19) . . . . ? C16 N11 C12 C13 -0.6(3) . . . . ? N11 C12 C13 C14 0.9(3) . . . . ? N11 C12 C13 C17 -178.8(2) . . . . ? C12 C13 C14 C15 -0.5(3) . . . . ? C17 C13 C14 C15 179.3(2) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? O11 N11 C16 C15 180.0(2) . . . . ? C12 N11 C16 C15 -0.1(3) . . . . ? C14 C15 C16 N11 0.5(4) . . . . ? C26 C21 I1 O11 25.8(10) . . . . ? C22 C21 I1 O11 -152.7(8) . . . . ? N11 O11 I1 C21 18.8(10) . . . . ? C26 C21 C22 C23 0.2(3) . . . . ? I1 C21 C22 C23 178.69(15) . . . . ? C26 C21 C22 I2 -177.10(15) . . . . ? I1 C21 C22 I2 1.4(2) . . . . ? C23 C22 I2 O11 -46.5(6) . . . 3_665 ? C21 C22 I2 O11 130.8(4) . . . 3_665 ? C21 C22 C23 F23 179.04(19) . . . . ? I2 C22 C23 F23 -3.5(3) . . . . ? C21 C22 C23 C24 -0.4(3) . . . . ? I2 C22 C23 C24 177.10(17) . . . . ? F23 C23 C24 F24 0.5(3) . . . . ? C22 C23 C24 F24 179.9(2) . . . . ? F23 C23 C24 C25 -179.2(2) . . . . ? C22 C23 C24 C25 0.3(3) . . . . ? F24 C24 C25 F25 -0.2(3) . . . . ? C23 C24 C25 F25 179.5(2) . . . . ? F24 C24 C25 C26 -179.7(2) . . . . ? C23 C24 C25 C26 0.0(3) . . . . ? C22 C21 C26 F26 179.70(19) . . . . ? I1 C21 C26 F26 1.2(3) . . . . ? C22 C21 C26 C25 0.0(3) . . . . ? I1 C21 C26 C25 -178.53(17) . . . . ? F25 C25 C26 F26 0.7(3) . . . . ? C24 C25 C26 F26 -179.8(2) . . . . ? F25 C25 C26 C21 -179.6(2) . . . . ? C24 C25 C26 C21 -0.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.704 _refine_diff_density_min -0.679 _refine_diff_density_rms 0.111 _database_code_depnum_ccdc_archive 'CCDC 953682' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tw1245mA8D1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; TW-6-13 (2,3,5,6-Me4-pyrazine-1,4-dioxide)2, (1,2-I2-F4-benzene)4 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C8 H12 N2 O2)2 (C6 F4 I2)4 ; _chemical_formula_sum 'C40 H24 F16 I8 N4 O4' _chemical_formula_weight 1943.83 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' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.1359(14) _cell_length_b 15.1116(15) _cell_length_c 24.361(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.927(3) _cell_angle_gamma 90.00 _cell_volume 5004.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9673 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 33.14 _exptl_crystal_description cube _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.580 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3568 _exptl_absorpt_coefficient_mu 5.064 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3527 _exptl_absorpt_correction_T_max 0.4021 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 81993 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 33.14 _reflns_number_total 18382 _reflns_number_gt 16534 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+20.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 18382 _refine_ls_number_parameters 657 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.0816 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 N11 N 0.61071(17) 0.51518(16) 0.76100(10) 0.0169(4) Uani 1 1 d . . . O11 O 0.70180(15) 0.51620(15) 0.75896(10) 0.0222(4) Uani 1 1 d . . . C12 C 0.5444(2) 0.57214(19) 0.72705(12) 0.0181(5) Uani 1 1 d . . . C13 C 0.4486(2) 0.57278(19) 0.73019(12) 0.0178(5) Uani 1 1 d . . . N14 N 0.42156(17) 0.51512(16) 0.76618(10) 0.0165(4) Uani 1 1 d . . . O14 O 0.33014(15) 0.51426(15) 0.76886(9) 0.0209(4) Uani 1 1 d . . . C15 C 0.4870(2) 0.45741(19) 0.79972(12) 0.0183(5) Uani 1 1 d . . . C16 C 0.5833(2) 0.45782(19) 0.79743(12) 0.0180(5) Uani 1 1 d . . . C22 C 0.5835(3) 0.6291(2) 0.68877(15) 0.0281(6) Uani 1 1 d . . . H22A H 0.5292 0.6615 0.6629 0.042 Uiso 1 1 calc R . . H22B H 0.6163 0.5922 0.6665 0.042 Uiso 1 1 calc R . . H22C H 0.6308 0.6713 0.7117 0.042 Uiso 1 1 calc R . . C23 C 0.3707(3) 0.6339(2) 0.69797(15) 0.0280(6) Uani 1 1 d . . . H23A H 0.3397 0.6633 0.7245 0.042 Uiso 1 1 calc R . . H23B H 0.3209 0.6003 0.6697 0.042 Uiso 1 1 calc R . . H23C H 0.4000 0.6785 0.6784 0.042 Uiso 1 1 calc R . . C25 C 0.4462(2) 0.3980(2) 0.83648(15) 0.0273(6) Uani 1 1 d . . . H25A H 0.3893 0.3660 0.8128 0.041 Uiso 1 1 calc R . . H25B H 0.4258 0.4334 0.8649 0.041 Uiso 1 1 calc R . . H25C H 0.4967 0.3556 0.8559 0.041 Uiso 1 1 calc R . . C26 C 0.6635(2) 0.4013(2) 0.83255(16) 0.0275(6) Uani 1 1 d . . . H26A H 0.6903 0.3642 0.8074 0.041 Uiso 1 1 calc R . . H26B H 0.6373 0.3635 0.8576 0.041 Uiso 1 1 calc R . . H26C H 0.7158 0.4389 0.8558 0.041 Uiso 1 1 calc R . . N31 N 0.13356(17) 0.23623(17) 0.31693(10) 0.0177(4) Uani 1 1 d . . . O31 O 0.22650(16) 0.24030(17) 0.31949(10) 0.0235(4) Uani 1 1 d . . . C32 C 0.0920(2) 0.15547(19) 0.32083(12) 0.0182(5) Uani 1 1 d . . . C33 C -0.0060(2) 0.15145(19) 0.31983(11) 0.0179(5) Uani 1 1 d . . . N34 N -0.05989(17) 0.22748(17) 0.31398(10) 0.0175(4) Uani 1 1 d . . . O34 O -0.15153(15) 0.22380(16) 0.31487(10) 0.0234(4) Uani 1 1 d . . . C35 C -0.0194(2) 0.3079(2) 0.30790(12) 0.0190(5) Uani 1 1 d . . . C36 C 0.0793(2) 0.3122(2) 0.31017(12) 0.0186(5) Uani 1 1 d . . . C42 C 0.1599(2) 0.0785(2) 0.32811(15) 0.0253(6) Uani 1 1 d . . . H42A H 0.2123 0.0850 0.3638 0.038 Uiso 1 1 calc R . . H42B H 0.1889 0.0759 0.2959 0.038 Uiso 1 1 calc R . . H42C H 0.1233 0.0238 0.3294 0.038 Uiso 1 1 calc R . . C43 C -0.0602(2) 0.0689(2) 0.32637(15) 0.0251(6) Uani 1 1 d . . . H43A H -0.1196 0.0637 0.2943 0.038 Uiso 1 1 calc R . . H43B H -0.0787 0.0714 0.3623 0.038 Uiso 1 1 calc R . . H43C H -0.0178 0.0174 0.3268 0.038 Uiso 1 1 calc R . . C45 C -0.0875(3) 0.3847(2) 0.29924(16) 0.0275(6) Uani 1 1 d . . . H45A H -0.1467 0.3715 0.2684 0.041 Uiso 1 1 calc R . . H45B H -0.0548 0.4369 0.2891 0.041 Uiso 1 1 calc R . . H45C H -0.1058 0.3964 0.3345 0.041 Uiso 1 1 calc R . . C46 C 0.1336(3) 0.3959(2) 0.30763(15) 0.0263(6) Uani 1 1 d . . . H46A H 0.1653 0.3922 0.2766 0.039 Uiso 1 1 calc R . . H46B H 0.1838 0.4049 0.3440 0.039 Uiso 1 1 calc R . . H46C H 0.0875 0.4457 0.3006 0.039 Uiso 1 1 calc R . . C51 C 0.6989(2) 0.3198(2) 0.59236(13) 0.0209(5) Uani 1 1 d . . . I1 I 0.738314(19) 0.36866(2) 0.675318(10) 0.04056(7) Uani 1 1 d . . . C52 C 0.6734(2) 0.2312(2) 0.57852(12) 0.0185(5) Uani 1 1 d . . . I2 I 0.681450(15) 0.133533(16) 0.640320(10) 0.02703(5) Uani 1 1 d . . . C53 C 0.6399(2) 0.2082(2) 0.52146(13) 0.0203(5) Uani 1 1 d . . . F53 F 0.61249(16) 0.12546(13) 0.50546(10) 0.0307(4) Uani 1 1 d . . . C54 C 0.6321(2) 0.2700(2) 0.47864(12) 0.0202(5) Uani 1 1 d . . . F54 F 0.59926(15) 0.24654(16) 0.42384(8) 0.0299(4) Uani 1 1 d . . . C55 C 0.6586(2) 0.3565(2) 0.49216(14) 0.0243(6) Uani 1 1 d . . . F55 F 0.65146(19) 0.41496(16) 0.45059(10) 0.0372(5) Uani 1 1 d . . . C56 C 0.6921(2) 0.3805(2) 0.54885(15) 0.0242(6) Uani 1 1 d . . . F56 F 0.7181(2) 0.46490(15) 0.56050(11) 0.0398(5) Uani 1 1 d . . . C61 C 0.4041(2) 0.2730(2) 0.52280(12) 0.0187(5) Uani 1 1 d . . . I3 I 0.344680(14) 0.258836(14) 0.434446(8) 0.02166(4) Uani 1 1 d . . . C62 C 0.4104(2) 0.2035(2) 0.56146(13) 0.0195(5) Uani 1 1 d . . . I4 I 0.377556(17) 0.073055(15) 0.536145(11) 0.03107(5) Uani 1 1 d . . . C63 C 0.4422(2) 0.2205(2) 0.61940(13) 0.0229(6) Uani 1 1 d . . . F63 F 0.44981(16) 0.15596(17) 0.65785(9) 0.0354(5) Uani 1 1 d . . . C64 C 0.4684(2) 0.3047(3) 0.64003(14) 0.0283(7) Uani 1 1 d . . . F64 F 0.49869(17) 0.3197(2) 0.69627(9) 0.0421(6) Uani 1 1 d . . . C65 C 0.4637(3) 0.3730(2) 0.60213(16) 0.0292(7) Uani 1 1 d . . . F65 F 0.4891(2) 0.45456(17) 0.62117(12) 0.0464(6) Uani 1 1 d . . . C66 C 0.4326(2) 0.3566(2) 0.54407(15) 0.0248(6) Uani 1 1 d . . . F66 F 0.43088(19) 0.42432(14) 0.50875(11) 0.0375(5) Uani 1 1 d . . . C71 C 0.1956(2) 0.3293(2) 0.59598(12) 0.0179(5) Uani 1 1 d . . . I5 I 0.244711(14) 0.394827(15) 0.674080(9) 0.02457(4) Uani 1 1 d . . . C72 C 0.1780(2) 0.2384(2) 0.59034(12) 0.0181(5) Uani 1 1 d . . . I6 I 0.207898(15) 0.150340(15) 0.658844(10) 0.02587(5) Uani 1 1 d . . . C73 C 0.1445(2) 0.2029(2) 0.53606(14) 0.0228(6) Uani 1 1 d . . . F73 F 0.12462(17) 0.11662(15) 0.52839(11) 0.0359(5) Uani 1 1 d . . . C74 C 0.1297(2) 0.2552(3) 0.48780(13) 0.0270(7) Uani 1 1 d . . . F74 F 0.10062(16) 0.2180(2) 0.43635(9) 0.0417(6) Uani 1 1 d . . . C75 C 0.1466(2) 0.3440(3) 0.49324(14) 0.0279(7) Uani 1 1 d . . . F75 F 0.13161(19) 0.3949(2) 0.44681(10) 0.0442(6) Uani 1 1 d . . . C76 C 0.1795(2) 0.3805(2) 0.54699(14) 0.0243(6) Uani 1 1 d . . . F76 F 0.19679(19) 0.46710(15) 0.55087(11) 0.0400(5) Uani 1 1 d . . . C81 C -0.0955(2) 0.2646(2) 0.52265(12) 0.0201(5) Uani 1 1 d . . . I7 I -0.136469(14) 0.250829(15) 0.433584(8) 0.02366(4) Uani 1 1 d . . . C82 C -0.0906(2) 0.1942(2) 0.56050(13) 0.0205(5) Uani 1 1 d . . . I8 I -0.124667(18) 0.064822(15) 0.532780(11) 0.03068(5) Uani 1 1 d . . . C83 C -0.0603(2) 0.2095(2) 0.61873(13) 0.0224(5) Uani 1 1 d . . . F83 F -0.05389(16) 0.14366(15) 0.65654(9) 0.0316(4) Uani 1 1 d . . . C84 C -0.0345(2) 0.2930(2) 0.64014(13) 0.0244(6) Uani 1 1 d . . . F84 F -0.00445(17) 0.30692(18) 0.69642(9) 0.0357(5) Uani 1 1 d . . . C85 C -0.0394(2) 0.3627(2) 0.60325(14) 0.0247(6) Uani 1 1 d . . . F85 F -0.01527(18) 0.44418(15) 0.62342(10) 0.0374(5) Uani 1 1 d . . . C86 C -0.0686(2) 0.3478(2) 0.54506(13) 0.0225(5) Uani 1 1 d . . . F86 F -0.06862(18) 0.41673(14) 0.51078(10) 0.0342(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.0172(10) 0.0183(11) 0.0169(10) -0.0038(8) 0.0076(8) -0.0025(8) O11 0.0172(9) 0.0256(11) 0.0266(11) -0.0051(8) 0.0111(8) -0.0028(8) C12 0.0229(12) 0.0181(12) 0.0141(11) -0.0011(9) 0.0061(10) -0.0030(9) C13 0.0214(12) 0.0187(12) 0.0137(11) -0.0003(9) 0.0053(9) -0.0025(9) N14 0.0164(10) 0.0186(11) 0.0147(10) -0.0031(8) 0.0045(8) -0.0013(8) O14 0.0157(9) 0.0259(11) 0.0221(10) -0.0023(8) 0.0068(8) -0.0021(7) C15 0.0204(12) 0.0177(12) 0.0176(12) 0.0005(9) 0.0066(10) -0.0013(9) C16 0.0194(12) 0.0167(12) 0.0180(12) -0.0002(9) 0.0051(10) -0.0002(9) C22 0.0306(15) 0.0302(16) 0.0259(15) 0.0070(12) 0.0121(13) -0.0038(13) C23 0.0265(15) 0.0308(16) 0.0253(15) 0.0085(12) 0.0048(12) 0.0046(12) C25 0.0258(14) 0.0282(16) 0.0306(16) 0.0115(13) 0.0120(12) -0.0013(12) C26 0.0215(13) 0.0275(15) 0.0341(17) 0.0098(13) 0.0085(12) 0.0058(11) N31 0.0165(10) 0.0242(12) 0.0128(9) -0.0007(8) 0.0045(8) -0.0020(8) O31 0.0154(9) 0.0365(12) 0.0197(10) -0.0001(9) 0.0065(8) -0.0025(8) C32 0.0205(12) 0.0209(13) 0.0136(11) -0.0002(9) 0.0053(9) -0.0009(10) C33 0.0200(12) 0.0211(12) 0.0121(10) -0.0007(9) 0.0036(9) -0.0014(10) N34 0.0167(10) 0.0226(11) 0.0126(9) -0.0008(8) 0.0032(8) -0.0019(8) O34 0.0149(9) 0.0329(12) 0.0224(10) -0.0007(9) 0.0049(8) -0.0021(8) C35 0.0210(12) 0.0212(13) 0.0141(11) -0.0008(9) 0.0038(9) -0.0015(10) C36 0.0212(12) 0.0204(13) 0.0150(11) -0.0001(9) 0.0063(9) -0.0018(10) C42 0.0264(14) 0.0235(14) 0.0278(15) 0.0006(12) 0.0107(12) 0.0045(11) C43 0.0257(14) 0.0216(14) 0.0263(15) 0.0029(11) 0.0043(12) -0.0044(11) C45 0.0259(14) 0.0244(15) 0.0320(16) 0.0024(12) 0.0078(13) 0.0051(12) C46 0.0293(15) 0.0215(14) 0.0310(16) 0.0011(12) 0.0131(13) -0.0056(11) C51 0.0186(12) 0.0278(14) 0.0176(12) -0.0067(10) 0.0070(10) -0.0032(10) I1 0.03347(12) 0.06824(18) 0.02345(10) -0.02239(11) 0.01364(9) -0.02269(12) C52 0.0164(11) 0.0219(13) 0.0179(12) 0.0001(10) 0.0057(9) 0.0018(9) I2 0.01995(8) 0.03419(11) 0.02804(10) 0.01187(8) 0.00843(7) 0.00565(7) C53 0.0193(12) 0.0202(13) 0.0218(13) -0.0046(10) 0.0061(10) -0.0009(10) F53 0.0348(11) 0.0210(9) 0.0368(11) -0.0088(8) 0.0106(9) -0.0060(8) C54 0.0167(11) 0.0287(14) 0.0150(11) -0.0041(10) 0.0039(9) 0.0003(10) F54 0.0276(10) 0.0445(12) 0.0166(8) -0.0074(8) 0.0045(7) -0.0021(8) C55 0.0241(13) 0.0256(15) 0.0245(14) 0.0022(11) 0.0088(11) 0.0008(11) F55 0.0489(13) 0.0336(11) 0.0314(11) 0.0121(9) 0.0148(10) 0.0015(10) C56 0.0271(14) 0.0190(13) 0.0278(15) -0.0055(11) 0.0098(12) -0.0036(11) F56 0.0547(15) 0.0216(10) 0.0443(13) -0.0099(9) 0.0157(11) -0.0106(9) C61 0.0181(11) 0.0213(13) 0.0172(11) 0.0001(10) 0.0056(9) 0.0013(9) I3 0.01962(8) 0.03036(10) 0.01587(8) -0.00067(7) 0.00635(6) 0.00061(7) C62 0.0170(11) 0.0211(13) 0.0216(13) 0.0020(10) 0.0074(10) 0.0002(9) I4 0.03054(11) 0.02059(9) 0.04164(13) 0.00139(8) 0.00915(9) -0.00396(8) C63 0.0165(11) 0.0348(16) 0.0189(12) 0.0048(11) 0.0076(10) 0.0029(11) F63 0.0263(10) 0.0541(14) 0.0263(10) 0.0169(10) 0.0080(8) 0.0021(9) C64 0.0194(13) 0.046(2) 0.0186(13) -0.0075(13) 0.0038(11) 0.0031(13) F64 0.0296(11) 0.0752(18) 0.0196(10) -0.0140(11) 0.0034(8) 0.0027(11) C65 0.0264(15) 0.0283(16) 0.0305(16) -0.0114(13) 0.0041(13) 0.0010(12) F65 0.0501(15) 0.0335(12) 0.0473(15) -0.0202(11) -0.0006(12) -0.0014(11) C66 0.0252(14) 0.0228(14) 0.0259(14) -0.0006(11) 0.0059(12) 0.0029(11) F66 0.0482(13) 0.0215(10) 0.0394(13) 0.0060(9) 0.0065(11) -0.0008(9) C71 0.0176(11) 0.0216(13) 0.0144(11) -0.0007(9) 0.0040(9) -0.0004(9) I5 0.02009(8) 0.03122(10) 0.02157(9) -0.01009(7) 0.00431(7) -0.00014(7) C72 0.0164(11) 0.0214(13) 0.0168(11) 0.0002(10) 0.0051(9) 0.0018(9) I6 0.02168(9) 0.02749(10) 0.02917(10) 0.01098(8) 0.00819(7) 0.00221(7) C73 0.0175(12) 0.0255(14) 0.0259(14) -0.0081(11) 0.0069(11) -0.0024(10) F73 0.0336(11) 0.0283(11) 0.0459(13) -0.0180(10) 0.0111(10) -0.0076(8) C74 0.0165(12) 0.049(2) 0.0153(12) -0.0075(12) 0.0039(10) 0.0006(12) F74 0.0247(10) 0.0805(19) 0.0191(9) -0.0189(11) 0.0048(8) -0.0027(11) C75 0.0231(14) 0.0428(19) 0.0182(13) 0.0085(13) 0.0065(11) 0.0046(13) F75 0.0438(13) 0.0673(17) 0.0221(10) 0.0216(11) 0.0098(9) 0.0087(12) C76 0.0242(14) 0.0244(14) 0.0252(14) 0.0062(11) 0.0081(11) 0.0029(11) F76 0.0486(14) 0.0242(10) 0.0458(14) 0.0116(10) 0.0103(11) -0.0006(9) C81 0.0175(11) 0.0257(14) 0.0166(12) -0.0020(10) 0.0037(9) 0.0011(10) I7 0.01837(8) 0.03695(11) 0.01563(8) -0.00294(7) 0.00461(6) 0.00048(7) C82 0.0176(11) 0.0238(14) 0.0212(13) -0.0040(10) 0.0071(10) -0.0017(10) I8 0.03313(11) 0.02461(10) 0.03594(12) -0.00515(8) 0.01221(9) -0.00651(8) C83 0.0178(12) 0.0304(15) 0.0206(13) 0.0026(11) 0.0080(10) 0.0007(11) F83 0.0306(10) 0.0396(12) 0.0259(10) 0.0102(9) 0.0098(8) -0.0013(9) C84 0.0198(12) 0.0370(17) 0.0153(12) -0.0043(11) 0.0029(10) 0.0018(11) F84 0.0340(11) 0.0544(14) 0.0154(9) -0.0079(9) 0.0013(8) 0.0004(10) C85 0.0219(13) 0.0260(15) 0.0239(14) -0.0069(11) 0.0024(11) 0.0019(11) F85 0.0411(12) 0.0283(11) 0.0365(12) -0.0128(9) 0.0001(10) -0.0006(9) C86 0.0223(13) 0.0242(14) 0.0195(13) -0.0001(11) 0.0028(10) 0.0040(10) F86 0.0439(12) 0.0245(10) 0.0307(11) 0.0065(8) 0.0041(9) 0.0044(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 N11 O11 1.302(3) . ? N11 C16 1.371(4) . ? N11 C12 1.371(4) . ? O11 I1 3.157(2) . ? C12 C13 1.377(4) . ? C12 C22 1.483(4) . ? C13 N14 1.363(4) . ? C13 C23 1.486(4) . ? N14 O14 1.312(3) . ? N14 C15 1.367(4) . ? O14 I5 2.918(2) . ? C15 C16 1.378(4) . ? C15 C25 1.491(4) . ? C16 C26 1.489(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N31 O31 1.300(3) . ? N31 C36 1.365(4) . ? N31 C32 1.369(4) . ? O31 I3 2.854(2) . ? C32 C33 1.380(4) . ? C32 C42 1.488(4) . ? C33 N34 1.364(4) . ? C33 C43 1.495(4) . ? N34 O34 1.303(3) . ? N34 C35 1.368(4) . ? O34 I7 2.870(2) . ? C35 C36 1.383(4) . ? C35 C45 1.485(4) . ? C36 C46 1.491(4) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C45 H45A 0.9800 . ? C45 H45B 0.9800 . ? C45 H45C 0.9800 . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C51 C56 1.385(5) . ? C51 C52 1.403(4) . ? C51 I1 2.079(3) . ? C52 C53 1.384(4) . ? C52 I2 2.089(3) . ? I2 O14 2.893(2) 2_646 ? C53 F53 1.335(4) . ? C53 C54 1.382(4) . ? C54 F54 1.336(3) . ? C54 C55 1.374(5) . ? C55 F55 1.327(4) . ? C55 C56 1.380(5) . ? C56 F56 1.336(4) . ? C61 C66 1.383(4) . ? C61 C62 1.398(4) . ? C61 I3 2.096(3) . ? C62 C63 1.383(4) . ? C62 I4 2.079(3) . ? I4 F53 3.182(2) 3_656 ? C63 F63 1.336(4) . ? C63 C64 1.381(5) . ? C64 F64 1.338(4) . ? C64 C65 1.374(6) . ? C65 F65 1.331(4) . ? C65 C66 1.384(5) . ? C66 F66 1.333(4) . ? C71 C76 1.388(4) . ? C71 C72 1.395(4) . ? C71 I5 2.088(3) . ? C72 C73 1.384(4) . ? C72 I6 2.085(3) . ? I6 O11 2.889(2) 2_646 ? C73 F73 1.337(4) . ? C73 C74 1.383(5) . ? C74 F74 1.332(4) . ? C74 C75 1.363(6) . ? C75 F75 1.336(4) . ? C75 C76 1.379(5) . ? C76 F76 1.331(4) . ? C81 C86 1.382(4) . ? C81 C82 1.397(4) . ? C81 I7 2.097(3) . ? C82 C83 1.384(4) . ? C82 I8 2.081(3) . ? I8 F73 3.121(2) 3_556 ? C83 F83 1.342(4) . ? C83 C84 1.376(5) . ? C84 F84 1.336(4) . ? C84 C85 1.374(5) . ? C85 F85 1.335(4) . ? C85 C86 1.382(4) . ? C86 F86 1.335(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 N11 C16 119.4(2) . . ? O11 N11 C12 119.3(2) . . ? C16 N11 C12 121.3(2) . . ? N11 O11 I1 110.78(16) . . ? N11 C12 C13 119.4(3) . . ? N11 C12 C22 115.6(3) . . ? C13 C12 C22 124.9(3) . . ? N14 C13 C12 119.0(3) . . ? N14 C13 C23 116.1(3) . . ? C12 C13 C23 124.9(3) . . ? O14 N14 C13 119.5(2) . . ? O14 N14 C15 118.6(2) . . ? C13 N14 C15 122.0(2) . . ? N14 O14 I5 99.57(15) . . ? N14 C15 C16 119.1(3) . . ? N14 C15 C25 115.7(3) . . ? C16 C15 C25 125.2(3) . . ? N11 C16 C15 119.2(3) . . ? N11 C16 C26 115.4(3) . . ? C15 C16 C26 125.4(3) . . ? C12 C22 H22A 109.5 . . ? C12 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C12 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C13 C23 H23A 109.5 . . ? C13 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C13 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C15 C25 H25A 109.5 . . ? C15 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C15 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C16 C26 H26A 109.5 . . ? C16 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C16 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O31 N31 C36 119.6(2) . . ? O31 N31 C32 119.1(3) . . ? C36 N31 C32 121.3(2) . . ? N31 O31 I3 111.33(16) . . ? N31 C32 C33 119.1(3) . . ? N31 C32 C42 115.5(3) . . ? C33 C32 C42 125.4(3) . . ? N34 C33 C32 119.6(3) . . ? N34 C33 C43 115.2(3) . . ? C32 C33 C43 125.2(3) . . ? O34 N34 C33 119.4(2) . . ? O34 N34 C35 119.1(2) . . ? C33 N34 C35 121.4(2) . . ? N34 O34 I7 102.21(16) . . ? N34 C35 C36 119.0(3) . . ? N34 C35 C45 115.9(3) . . ? C36 C35 C45 125.1(3) . . ? N31 C36 C35 119.5(3) . . ? N31 C36 C46 116.1(3) . . ? C35 C36 C46 124.4(3) . . ? C32 C42 H42A 109.5 . . ? C32 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C32 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C33 C43 H43A 109.5 . . ? C33 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C33 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C35 C45 H45A 109.5 . . ? C35 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C35 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C36 C46 H46A 109.5 . . ? C36 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C36 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C56 C51 C52 119.3(3) . . ? C56 C51 I1 116.9(2) . . ? C52 C51 I1 123.7(2) . . ? C51 I1 O11 146.17(10) . . ? C53 C52 C51 118.4(3) . . ? C53 C52 I2 118.8(2) . . ? C51 C52 I2 122.8(2) . . ? C52 I2 O14 171.12(9) . 2_646 ? F53 C53 C54 117.1(3) . . ? F53 C53 C52 121.4(3) . . ? C54 C53 C52 121.5(3) . . ? F54 C54 C55 119.3(3) . . ? F54 C54 C53 120.6(3) . . ? C55 C54 C53 120.1(3) . . ? F55 C55 C54 119.5(3) . . ? F55 C55 C56 121.5(3) . . ? C54 C55 C56 119.1(3) . . ? F56 C56 C55 117.6(3) . . ? F56 C56 C51 120.8(3) . . ? C55 C56 C51 121.6(3) . . ? C66 C61 C62 118.4(3) . . ? C66 C61 I3 118.2(2) . . ? C62 C61 I3 123.3(2) . . ? C61 I3 O31 168.41(9) . . ? C63 C62 C61 119.4(3) . . ? C63 C62 I4 117.6(2) . . ? C61 C62 I4 123.0(2) . . ? C62 I4 F53 164.23(9) . 3_656 ? F63 C63 C64 117.1(3) . . ? F63 C63 C62 121.4(3) . . ? C64 C63 C62 121.5(3) . . ? F64 C64 C65 120.3(3) . . ? F64 C64 C63 120.4(3) . . ? C65 C64 C63 119.3(3) . . ? F65 C65 C64 120.2(3) . . ? F65 C65 C66 120.1(4) . . ? C64 C65 C66 119.7(3) . . ? F66 C66 C61 120.5(3) . . ? F66 C66 C65 117.8(3) . . ? C61 C66 C65 121.7(3) . . ? C76 C71 C72 118.7(3) . . ? C76 C71 I5 117.0(2) . . ? C72 C71 I5 124.2(2) . . ? C71 I5 O14 167.54(9) . . ? C73 C72 C71 118.7(3) . . ? C73 C72 I6 117.3(2) . . ? C71 C72 I6 123.9(2) . . ? C72 I6 O11 163.06(9) . 2_646 ? F73 C73 C74 117.4(3) . . ? F73 C73 C72 121.0(3) . . ? C74 C73 C72 121.6(3) . . ? F74 C74 C75 120.5(3) . . ? F74 C74 C73 119.7(3) . . ? C75 C74 C73 119.8(3) . . ? F75 C75 C74 120.1(3) . . ? F75 C75 C76 120.5(3) . . ? C74 C75 C76 119.4(3) . . ? F76 C76 C75 117.9(3) . . ? F76 C76 C71 120.2(3) . . ? C75 C76 C71 121.8(3) . . ? C86 C81 C82 118.3(3) . . ? C86 C81 I7 117.8(2) . . ? C82 C81 I7 123.9(2) . . ? C81 I7 O34 168.44(9) . . ? C83 C82 C81 119.6(3) . . ? C83 C82 I8 118.0(2) . . ? C81 C82 I8 122.4(2) . . ? C82 I8 F73 161.79(9) . 3_556 ? F83 C83 C84 117.3(3) . . ? F83 C83 C82 121.5(3) . . ? C84 C83 C82 121.2(3) . . ? F84 C84 C85 119.7(3) . . ? F84 C84 C83 120.7(3) . . ? C85 C84 C83 119.6(3) . . ? F85 C85 C84 120.3(3) . . ? F85 C85 C86 120.2(3) . . ? C84 C85 C86 119.5(3) . . ? F86 C86 C81 120.7(3) . . ? F86 C86 C85 117.6(3) . . ? C81 C86 C85 121.8(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 C16 N11 O11 I1 84.6(2) . . . . ? C12 N11 O11 I1 -96.1(2) . . . . ? O11 N11 C12 C13 -178.3(2) . . . . ? C16 N11 C12 C13 1.0(4) . . . . ? O11 N11 C12 C22 1.9(4) . . . . ? C16 N11 C12 C22 -178.7(3) . . . . ? N11 C12 C13 N14 -1.5(4) . . . . ? C22 C12 C13 N14 178.2(3) . . . . ? N11 C12 C13 C23 176.9(3) . . . . ? C22 C12 C13 C23 -3.4(5) . . . . ? C12 C13 N14 O14 -179.0(2) . . . . ? C23 C13 N14 O14 2.5(4) . . . . ? C12 C13 N14 C15 0.8(4) . . . . ? C23 C13 N14 C15 -177.8(3) . . . . ? C13 N14 O14 I5 85.5(2) . . . . ? C15 N14 O14 I5 -94.2(2) . . . . ? O14 N14 C15 C16 -179.8(3) . . . . ? C13 N14 C15 C16 0.4(4) . . . . ? O14 N14 C15 C25 0.2(4) . . . . ? C13 N14 C15 C25 -179.5(3) . . . . ? O11 N11 C16 C15 179.6(3) . . . . ? C12 N11 C16 C15 0.2(4) . . . . ? O11 N11 C16 C26 0.6(4) . . . . ? C12 N11 C16 C26 -178.7(3) . . . . ? N14 C15 C16 N11 -0.9(4) . . . . ? C25 C15 C16 N11 179.0(3) . . . . ? N14 C15 C16 C26 177.9(3) . . . . ? C25 C15 C16 C26 -2.1(5) . . . . ? C36 N31 O31 I3 91.0(2) . . . . ? C32 N31 O31 I3 -89.2(2) . . . . ? O31 N31 C32 C33 178.1(2) . . . . ? C36 N31 C32 C33 -2.2(4) . . . . ? O31 N31 C32 C42 0.3(4) . . . . ? C36 N31 C32 C42 -180.0(3) . . . . ? N31 C32 C33 N34 1.2(4) . . . . ? C42 C32 C33 N34 178.7(3) . . . . ? N31 C32 C33 C43 -177.0(3) . . . . ? C42 C32 C33 C43 0.5(5) . . . . ? C32 C33 N34 O34 -177.8(2) . . . . ? C43 C33 N34 O34 0.5(4) . . . . ? C32 C33 N34 C35 1.3(4) . . . . ? C43 C33 N34 C35 179.7(3) . . . . ? C33 N34 O34 I7 91.7(2) . . . . ? C35 N34 O34 I7 -87.5(2) . . . . ? O34 N34 C35 C36 176.4(2) . . . . ? C33 N34 C35 C36 -2.7(4) . . . . ? O34 N34 C35 C45 -3.6(4) . . . . ? C33 N34 C35 C45 177.3(3) . . . . ? O31 N31 C36 C35 -179.5(2) . . . . ? C32 N31 C36 C35 0.8(4) . . . . ? O31 N31 C36 C46 -1.4(4) . . . . ? C32 N31 C36 C46 178.9(3) . . . . ? N34 C35 C36 N31 1.7(4) . . . . ? C45 C35 C36 N31 -178.4(3) . . . . ? N34 C35 C36 C46 -176.2(3) . . . . ? C45 C35 C36 C46 3.7(5) . . . . ? C56 C51 I1 O11 47.0(3) . . . . ? C52 C51 I1 O11 -128.9(2) . . . . ? N11 O11 I1 C51 59.3(3) . . . . ? C56 C51 C52 C53 -1.5(4) . . . . ? I1 C51 C52 C53 174.2(2) . . . . ? C56 C51 C52 I2 179.6(2) . . . . ? I1 C51 C52 I2 -4.6(3) . . . . ? C53 C52 I2 O14 -116.1(6) . . . 2_646 ? C51 C52 I2 O14 62.8(7) . . . 2_646 ? C51 C52 C53 F53 -178.6(3) . . . . ? I2 C52 C53 F53 0.3(4) . . . . ? C51 C52 C53 C54 0.5(4) . . . . ? I2 C52 C53 C54 179.4(2) . . . . ? F53 C53 C54 F54 -0.7(4) . . . . ? C52 C53 C54 F54 -179.8(3) . . . . ? F53 C53 C54 C55 179.7(3) . . . . ? C52 C53 C54 C55 0.5(4) . . . . ? F54 C54 C55 F55 -0.3(4) . . . . ? C53 C54 C55 F55 179.4(3) . . . . ? F54 C54 C55 C56 179.8(3) . . . . ? C53 C54 C55 C56 -0.5(5) . . . . ? F55 C55 C56 F56 -0.5(5) . . . . ? C54 C55 C56 F56 179.4(3) . . . . ? F55 C55 C56 C51 179.5(3) . . . . ? C54 C55 C56 C51 -0.6(5) . . . . ? C52 C51 C56 F56 -178.4(3) . . . . ? I1 C51 C56 F56 5.6(4) . . . . ? C52 C51 C56 C55 1.6(5) . . . . ? I1 C51 C56 C55 -174.4(2) . . . . ? C66 C61 I3 O31 -98.8(5) . . . . ? C62 C61 I3 O31 76.9(6) . . . . ? N31 O31 I3 C61 -2.5(6) . . . . ? C66 C61 C62 C63 1.7(4) . . . . ? I3 C61 C62 C63 -174.0(2) . . . . ? C66 C61 C62 I4 -176.6(2) . . . . ? I3 C61 C62 I4 7.7(3) . . . . ? C63 C62 I4 F53 -95.9(4) . . . 3_656 ? C61 C62 I4 F53 82.4(4) . . . 3_656 ? C61 C62 C63 F63 -179.7(3) . . . . ? I4 C62 C63 F63 -1.3(4) . . . . ? C61 C62 C63 C64 -0.2(4) . . . . ? I4 C62 C63 C64 178.1(2) . . . . ? F63 C63 C64 F64 -0.8(4) . . . . ? C62 C63 C64 F64 179.8(3) . . . . ? F63 C63 C64 C65 178.7(3) . . . . ? C62 C63 C64 C65 -0.7(5) . . . . ? F64 C64 C65 F65 -0.2(5) . . . . ? C63 C64 C65 F65 -179.6(3) . . . . ? F64 C64 C65 C66 179.7(3) . . . . ? C63 C64 C65 C66 0.2(5) . . . . ? C62 C61 C66 F66 177.8(3) . . . . ? I3 C61 C66 F66 -6.2(4) . . . . ? C62 C61 C66 C65 -2.2(5) . . . . ? I3 C61 C66 C65 173.7(3) . . . . ? F65 C65 C66 F66 1.1(5) . . . . ? C64 C65 C66 F66 -178.8(3) . . . . ? F65 C65 C66 C61 -178.9(3) . . . . ? C64 C65 C66 C61 1.2(5) . . . . ? C76 C71 I5 O14 -25.7(6) . . . . ? C72 C71 I5 O14 154.6(3) . . . . ? N14 O14 I5 C71 -56.6(5) . . . . ? C76 C71 C72 C73 -0.4(4) . . . . ? I5 C71 C72 C73 179.4(2) . . . . ? C76 C71 C72 I6 175.3(2) . . . . ? I5 C71 C72 I6 -4.9(3) . . . . ? C73 C72 I6 O11 72.5(4) . . . 2_646 ? C71 C72 I6 O11 -103.3(4) . . . 2_646 ? C71 C72 C73 F73 -178.6(3) . . . . ? I6 C72 C73 F73 5.4(4) . . . . ? C71 C72 C73 C74 0.9(4) . . . . ? I6 C72 C73 C74 -175.1(2) . . . . ? F73 C73 C74 F74 -2.7(4) . . . . ? C72 C73 C74 F74 177.8(3) . . . . ? F73 C73 C74 C75 178.4(3) . . . . ? C72 C73 C74 C75 -1.1(5) . . . . ? F74 C74 C75 F75 1.8(5) . . . . ? C73 C74 C75 F75 -179.4(3) . . . . ? F74 C74 C75 C76 -178.1(3) . . . . ? C73 C74 C75 C76 0.7(5) . . . . ? F75 C75 C76 F76 -0.9(5) . . . . ? C74 C75 C76 F76 179.0(3) . . . . ? F75 C75 C76 C71 179.9(3) . . . . ? C74 C75 C76 C71 -0.2(5) . . . . ? C72 C71 C76 F76 -179.1(3) . . . . ? I5 C71 C76 F76 1.1(4) . . . . ? C72 C71 C76 C75 0.0(5) . . . . ? I5 C71 C76 C75 -179.7(2) . . . . ? C86 C81 I7 O34 92.1(5) . . . . ? C82 C81 I7 O34 -85.7(6) . . . . ? N34 O34 I7 C81 -16.1(6) . . . . ? C86 C81 C82 C83 0.6(4) . . . . ? I7 C81 C82 C83 178.4(2) . . . . ? C86 C81 C82 I8 -178.1(2) . . . . ? I7 C81 C82 I8 -0.3(3) . . . . ? C83 C82 I8 F73 -123.0(3) . . . 3_556 ? C81 C82 I8 F73 55.6(5) . . . 3_556 ? C81 C82 C83 F83 -179.5(3) . . . . ? I8 C82 C83 F83 -0.8(4) . . . . ? C81 C82 C83 C84 -0.1(4) . . . . ? I8 C82 C83 C84 178.6(2) . . . . ? F83 C83 C84 F84 0.0(4) . . . . ? C82 C83 C84 F84 -179.4(3) . . . . ? F83 C83 C84 C85 179.7(3) . . . . ? C82 C83 C84 C85 0.3(5) . . . . ? F84 C84 C85 F85 -0.8(5) . . . . ? C83 C84 C85 F85 179.5(3) . . . . ? F84 C84 C85 C86 178.7(3) . . . . ? C83 C84 C85 C86 -1.0(5) . . . . ? C82 C81 C86 F86 177.7(3) . . . . ? I7 C81 C86 F86 -0.2(4) . . . . ? C82 C81 C86 C85 -1.3(5) . . . . ? I7 C81 C86 C85 -179.2(2) . . . . ? F85 C85 C86 F86 2.0(5) . . . . ? C84 C85 C86 F86 -177.5(3) . . . . ? F85 C85 C86 C81 -179.0(3) . . . . ? C84 C85 C86 C81 1.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 33.14 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 7.622 _refine_diff_density_min -6.171 _refine_diff_density_rms 0.184 _database_code_depnum_ccdc_archive 'CCDC 953683' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tw1237mA8D3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; TW-6-15 2,3,5,6-Me4-pyridine-1,4-dioxide, (1,3,5-F3-2,4,6-I3-benzene)2 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; (C8 H12 N2 O2) (C6 F3 I3)2 ; _chemical_formula_sum 'C20 H12 F6 I6 N2 O2' _chemical_formula_weight 1187.72 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9660(6) _cell_length_b 9.2821(7) _cell_length_c 10.1097(8) _cell_angle_alpha 100.812(3) _cell_angle_beta 106.262(2) _cell_angle_gamma 95.408(3) _cell_volume 696.28(9) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9888 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 33.29 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.833 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 534 _exptl_absorpt_coefficient_mu 6.755 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2211 _exptl_absorpt_correction_T_max 0.4515 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 18582 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 33.13 _reflns_number_total 4468 _reflns_number_gt 4255 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+0.8000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4468 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0220 _refine_ls_R_factor_gt 0.0204 _refine_ls_wR_factor_ref 0.0530 _refine_ls_wR_factor_gt 0.0522 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _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 C11 C 0.7118(3) 0.5175(3) 0.4630(2) 0.0162(4) Uani 1 1 d . . . I11 I 0.57832(2) 0.639302(17) 0.324676(16) 0.01707(4) Uani 1 1 d . . . C12 C 0.8355(3) 0.5847(3) 0.5912(3) 0.0170(4) Uani 1 1 d . . . F12 F 0.8655(2) 0.73319(17) 0.62913(16) 0.0231(3) Uani 1 1 d . . . C13 C 0.9296(3) 0.5059(3) 0.6824(2) 0.0167(4) Uani 1 1 d . . . I13 I 1.11585(2) 0.613179(17) 0.873884(16) 0.01806(4) Uani 1 1 d . . . C14 C 0.8972(3) 0.3522(3) 0.6380(3) 0.0165(4) Uani 1 1 d . . . F14 F 0.9839(2) 0.27184(17) 0.72349(17) 0.0231(3) Uani 1 1 d . . . C15 C 0.7777(3) 0.2784(3) 0.5097(3) 0.0166(4) Uani 1 1 d . . . I15 I 0.73381(2) 0.048603(17) 0.445962(18) 0.02161(5) Uani 1 1 d . . . C16 C 0.6852(3) 0.3646(3) 0.4257(3) 0.0166(4) Uani 1 1 d . . . F16 F 0.5614(2) 0.29483(17) 0.30455(15) 0.0224(3) Uani 1 1 d . . . N21 N 0.4526(3) 0.8893(2) 0.0582(2) 0.0162(4) Uani 1 1 d . . . O21 O 0.4028(2) 0.7812(2) 0.11228(19) 0.0207(4) Uani 1 1 d . . . C22 C 0.3680(3) 1.0103(3) 0.0637(2) 0.0170(4) Uani 1 1 d . . . C26 C 0.5833(3) 0.8763(3) -0.0043(2) 0.0170(4) Uani 1 1 d . . . C32 C 0.2313(4) 1.0097(3) 0.1378(3) 0.0230(5) Uani 1 1 d . . . H32A H 0.1792 1.1011 0.1362 0.034 Uiso 1 1 calc R . . H32B H 0.2860 1.0039 0.2360 0.034 Uiso 1 1 calc R . . H32C H 0.1386 0.9236 0.0902 0.034 Uiso 1 1 calc R . . C36 C 0.6641(4) 0.7386(3) -0.0022(3) 0.0228(5) Uani 1 1 d . . . H36A H 0.7567 0.7414 -0.0486 0.034 Uiso 1 1 calc R . . H36B H 0.5728 0.6521 -0.0524 0.034 Uiso 1 1 calc R . . H36C H 0.7160 0.7313 0.0960 0.034 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 C11 0.0183(11) 0.0155(10) 0.0168(10) 0.0063(8) 0.0059(8) 0.0053(8) I11 0.01933(8) 0.01532(7) 0.01712(8) 0.00613(5) 0.00428(5) 0.00437(5) C12 0.0176(11) 0.0151(10) 0.0179(11) 0.0033(8) 0.0048(8) 0.0023(8) F12 0.0298(8) 0.0141(7) 0.0211(7) 0.0021(5) 0.0026(6) 0.0028(6) C13 0.0152(10) 0.0177(10) 0.0156(10) 0.0035(8) 0.0021(8) 0.0024(8) I13 0.01760(8) 0.01797(8) 0.01593(7) 0.00285(5) 0.00198(5) 0.00115(5) C14 0.0149(10) 0.0152(10) 0.0187(11) 0.0054(8) 0.0028(8) 0.0021(8) F14 0.0225(8) 0.0187(7) 0.0243(8) 0.0089(6) -0.0020(6) 0.0044(6) C15 0.0168(11) 0.0127(9) 0.0193(11) 0.0025(8) 0.0048(8) 0.0008(8) I15 0.02328(9) 0.01336(7) 0.02537(9) 0.00413(6) 0.00329(6) 0.00220(6) C16 0.0163(10) 0.0166(10) 0.0155(10) 0.0030(8) 0.0034(8) 0.0006(8) F16 0.0259(8) 0.0177(7) 0.0166(7) 0.0035(5) -0.0033(5) -0.0001(6) N21 0.0172(9) 0.0147(9) 0.0131(9) 0.0032(7) -0.0007(7) 0.0017(7) O21 0.0236(9) 0.0182(8) 0.0186(8) 0.0096(7) 0.0008(6) 0.0019(7) C22 0.0186(11) 0.0174(10) 0.0134(10) 0.0038(8) 0.0017(8) 0.0039(8) C26 0.0191(11) 0.0162(10) 0.0132(10) 0.0026(8) 0.0008(8) 0.0040(8) C32 0.0237(12) 0.0241(12) 0.0229(12) 0.0062(10) 0.0087(9) 0.0055(10) C36 0.0268(13) 0.0210(12) 0.0233(12) 0.0098(9) 0.0063(9) 0.0114(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 C11 C16 1.379(3) . ? C11 C12 1.380(3) . ? C11 I11 2.086(2) . ? I11 O21 2.8331(16) . ? C12 F12 1.339(3) . ? C12 C13 1.384(3) . ? C13 C14 1.389(3) . ? C13 I13 2.081(2) . ? I13 O21 2.8809(18) 1_656 ? C14 F14 1.336(3) . ? C14 C15 1.382(3) . ? C15 C16 1.386(3) . ? C15 I15 2.074(2) . ? I15 I11 3.7398(4) 1_545 ? C16 F16 1.341(3) . ? N21 O21 1.310(3) . ? N21 C22 1.363(3) . ? N21 C26 1.364(3) . ? C22 C26 1.382(3) 2_675 ? C22 C32 1.485(4) . ? C26 C22 1.382(3) 2_675 ? C26 C36 1.485(3) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 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 C16 C11 C12 117.1(2) . . ? C16 C11 I11 120.49(17) . . ? C12 C11 I11 122.29(18) . . ? C11 I11 O21 173.62(8) . . ? F12 C12 C11 118.3(2) . . ? F12 C12 C13 118.5(2) . . ? C11 C12 C13 123.2(2) . . ? C12 C13 C14 116.8(2) . . ? C12 C13 I13 121.50(18) . . ? C14 C13 I13 121.70(17) . . ? C13 I13 O21 170.97(8) . 1_656 ? F14 C14 C15 118.4(2) . . ? F14 C14 C13 118.7(2) . . ? C15 C14 C13 122.9(2) . . ? C14 C15 C16 117.0(2) . . ? C14 C15 I15 121.91(17) . . ? C16 C15 I15 121.04(17) . . ? C15 I15 I11 170.79(7) . 1_545 ? F16 C16 C11 119.0(2) . . ? F16 C16 C15 118.0(2) . . ? C11 C16 C15 123.0(2) . . ? O21 N21 C22 118.3(2) . . ? O21 N21 C26 119.5(2) . . ? C22 N21 C26 122.2(2) . . ? N21 O21 I11 134.23(14) . . ? N21 C22 C26 118.9(2) . 2_675 ? N21 C22 C32 115.9(2) . . ? C26 C22 C32 125.2(2) 2_675 . ? N21 C26 C22 118.9(2) . 2_675 ? N21 C26 C36 116.4(2) . . ? C22 C26 C36 124.7(2) 2_675 . ? C22 C32 H32A 109.5 . . ? C22 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C22 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C26 C36 H36A 109.5 . . ? C26 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C26 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 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 C16 C11 I11 O21 -38.7(8) . . . . ? C12 C11 I11 O21 138.1(6) . . . . ? C16 C11 C12 F12 179.2(2) . . . . ? I11 C11 C12 F12 2.3(3) . . . . ? C16 C11 C12 C13 -1.0(4) . . . . ? I11 C11 C12 C13 -177.86(19) . . . . ? F12 C12 C13 C14 -178.8(2) . . . . ? C11 C12 C13 C14 1.3(4) . . . . ? F12 C12 C13 I13 -0.6(3) . . . . ? C11 C12 C13 I13 179.60(19) . . . . ? C12 C13 I13 O21 -62.0(6) . . . 1_656 ? C14 C13 I13 O21 116.1(5) . . . 1_656 ? C12 C13 C14 F14 -179.3(2) . . . . ? I13 C13 C14 F14 2.4(3) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? I13 C13 C14 C15 -178.24(19) . . . . ? F14 C14 C15 C16 177.7(2) . . . . ? C13 C14 C15 C16 -1.6(4) . . . . ? F14 C14 C15 I15 -1.1(3) . . . . ? C13 C14 C15 I15 179.52(19) . . . . ? C14 C15 I15 I11 124.3(4) . . . 1_545 ? C16 C15 I15 I11 -54.5(5) . . . 1_545 ? C12 C11 C16 F16 177.5(2) . . . . ? I11 C11 C16 F16 -5.6(3) . . . . ? C12 C11 C16 C15 -0.8(4) . . . . ? I11 C11 C16 C15 176.17(19) . . . . ? C14 C15 C16 F16 -176.2(2) . . . . ? I15 C15 C16 F16 2.6(3) . . . . ? C14 C15 C16 C11 2.0(4) . . . . ? I15 C15 C16 C11 -179.12(19) . . . . ? C22 N21 O21 I11 -122.5(2) . . . . ? C26 N21 O21 I11 58.9(3) . . . . ? C11 I11 O21 N21 -93.5(7) . . . . ? O21 N21 C22 C26 -178.6(2) . . . 2_675 ? C26 N21 C22 C26 -0.1(4) . . . 2_675 ? O21 N21 C22 C32 2.7(3) . . . . ? C26 N21 C22 C32 -178.8(2) . . . . ? O21 N21 C26 C22 178.6(2) . . . 2_675 ? C22 N21 C26 C22 0.1(4) . . . 2_675 ? O21 N21 C26 C36 -1.7(3) . . . . ? C22 N21 C26 C36 179.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.842 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 1.535 _refine_diff_density_min -0.912 _refine_diff_density_rms 0.134 #END _database_code_depnum_ccdc_archive 'CCDC 953684'