# 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_compound_2 _database_code_depnum_ccdc_archive 'CCDC 907134' #TrackingRef 'compound_2.cif' #=================================================================== #=================================================================== # 5. CHEMICAL DATA #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C16 F8 I2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 F8 I2' _chemical_formula_weight 597.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source I I -0.4742 1.8119 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=================================================================== # 6. CRYSTAL DATA #=================================================================== _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 11.8260(5) _cell_length_b 5.0779(2) _cell_length_c 14.4717(6) _cell_angle_alpha 90 _cell_angle_beta 113.431(2) _cell_angle_gamma 90 _cell_volume 797.38(6) _cell_formula_units_Z 2 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 7288 _cell_measurement_theta_min 1.88 _cell_measurement_theta_max 25.32 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.490 _exptl_crystal_density_method none _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 4.027 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5437 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details 'SADABS, Bruker, 2008b' _exptl_special_details ; Diffractometer operator E. Herdtweck scanspeed 10 s per frame dx 50 2016 frames measured in 5 data sets phi-scan with delta_phi = 0.50 omega-scans with delta_omega = 0.50 ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'rotating anode FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Bruker APEX-II CCD ' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 16 # 8 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 8968 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.32 _reflns_number_total 1371 _reflns_number_gt 1314 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX II Control Software (Bruker, 2008a)' _computing_cell_refinement 'SAINT (Bruker, 2008b)' _computing_data_reduction 'SAINT (Bruker, 2008b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2010)' _computing_publication_material 'PLATON (Spek, 2010)' #=================================================================== # 8. REFINEMENT DATA #=================================================================== _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs 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 sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0204P)^2^+2.2924P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_extinction_method none _refine_ls_number_reflns 1371 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0233 _refine_ls_R_factor_gt 0.0223 _refine_ls_wR_factor_ref 0.0550 _refine_ls_wR_factor_gt 0.0545 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 1.065 _refine_diff_density_min -0.695 _refine_diff_density_rms 0.087 #=================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS #=================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags I1 I Uani 0.37017(2) 0.91511(5) 0.25294(2) 1.000 0.0356(1) . . F1 F Uani 0.1562(2) 0.5148(4) 0.23555(16) 1.000 0.0316(7) . . F2 F Uani 0.0245(2) 0.4442(4) 0.34691(18) 1.000 0.0346(7) . . F3 F Uani 0.0625(2) 0.7535(5) 0.50943(18) 1.000 0.0406(8) . . F4 F Uani 0.2321(2) 1.1411(5) 0.55844(17) 1.000 0.0392(8) . . C1 C Uani 0.4559(3) 1.4024(7) 0.4837(3) 1.000 0.0271(10) . . C2 C Uani 0.3794(3) 1.2312(7) 0.4546(3) 1.000 0.0257(10) . . C3 C Uani 0.2874(3) 1.0300(6) 0.4235(3) 1.000 0.0229(10) . . C4 C Uani 0.2667(3) 0.8698(6) 0.3391(3) 1.000 0.0218(10) . . C5 C Uani 0.1779(3) 0.6749(6) 0.3148(3) 1.000 0.0221(10) . . C6 C Uani 0.1095(3) 0.6350(6) 0.3716(3) 1.000 0.0239(10) . . C7 C Uani 0.1283(3) 0.7914(7) 0.4545(3) 1.000 0.0268(11) . . C8 C Uani 0.2161(3) 0.9879(7) 0.4805(3) 1.000 0.0296(10) . . 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 0.0331(2) 0.0436(2) 0.0386(2) 0.0111(1) 0.0233(1) 0.0030(1) F1 0.0353(12) 0.0333(11) 0.0260(12) -0.0049(9) 0.0120(10) -0.0008(9) F2 0.0300(12) 0.0327(11) 0.0404(14) -0.0079(9) 0.0133(10) -0.0163(9) F3 0.0451(13) 0.0445(13) 0.0462(15) -0.0104(11) 0.0330(12) -0.0183(11) F4 0.0472(14) 0.0408(12) 0.0342(14) -0.0110(10) 0.0212(11) -0.0132(10) C1 0.0207(17) 0.0244(17) 0.032(2) 0.0093(14) 0.0061(16) 0.0025(14) C2 0.0206(17) 0.0225(17) 0.030(2) 0.0074(14) 0.0058(15) -0.0004(14) C3 0.0176(16) 0.0211(16) 0.026(2) 0.0060(13) 0.0043(14) -0.0006(13) C4 0.0175(16) 0.0235(16) 0.026(2) 0.0081(13) 0.0103(15) 0.0034(13) C5 0.0192(16) 0.0219(16) 0.0212(19) 0.0009(13) 0.0037(14) 0.0030(13) C6 0.0177(16) 0.0212(16) 0.029(2) 0.0010(13) 0.0052(15) -0.0048(13) C7 0.0239(18) 0.0288(18) 0.032(2) 0.0000(15) 0.0156(16) -0.0047(14) C8 0.0229(18) 0.0189(16) 0.038(2) -0.0044(15) 0.0025(16) -0.0032(14) #================================================================== # 10. MOLECULAR GEOMETRY #=================================================================== loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C4 2.078(4) . . yes F1 C5 1.345(4) . . yes F2 C6 1.338(4) . . yes F3 C7 1.329(5) . . yes F4 C8 1.320(5) . . yes C1 C2 1.204(5) . . no C1 C1 1.379(5) . 3_686 no C2 C3 1.429(5) . . no C3 C4 1.406(5) . . no C3 C8 1.411(6) . . no C4 C5 1.383(5) . . no C5 C6 1.378(6) . . no C6 C7 1.381(5) . . no C7 C8 1.380(5) . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C1 C2 179.4(4) 3_686 . . no C1 C2 C3 177.7(4) . . . no C2 C3 C4 122.4(4) . . . no C2 C3 C8 118.8(3) . . . no C4 C3 C8 118.8(3) . . . no I1 C4 C3 121.1(3) . . . yes I1 C4 C5 119.7(3) . . . yes C3 C4 C5 119.2(4) . . . no F1 C5 C4 121.2(3) . . . yes F1 C5 C6 117.5(3) . . . yes C4 C5 C6 121.3(3) . . . no F2 C6 C5 120.3(3) . . . yes F2 C6 C7 119.5(3) . . . yes C5 C6 C7 120.2(3) . . . no F3 C7 C6 120.4(3) . . . yes F3 C7 C8 119.8(3) . . . yes C6 C7 C8 119.8(4) . . . no F4 C8 C3 119.6(3) . . . yes F4 C8 C7 119.7(4) . . . yes C3 C8 C7 120.7(3) . . . no # End of Crystallographic Information File data_k09110 _database_code_depnum_ccdc_archive 'CCDC 907557' #TrackingRef 'web_deposit_cif_file_0_MarkS.Taylor_1351046475.compound_6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H36 N, C16 F8 I2, I' _chemical_formula_sum 'C32 H36 F8 I3 N' _chemical_formula_weight 967.32 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' I I -0.4742 1.8119 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.7911(4) _cell_length_b 30.7832(10) _cell_length_c 8.3658(1) _cell_angle_alpha 90.00 _cell_angle_beta 96.2920(19) _cell_angle_gamma 90.00 _cell_volume 3530.17(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 12445 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _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 1.820 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1864 _exptl_absorpt_coefficient_mu 2.721 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.677 _exptl_absorpt_correction_T_max 0.768 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12445 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6063 _reflns_number_gt 5333 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SIR-92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0413P)^2^+27.6591P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.51(3) _refine_ls_number_reflns 6063 _refine_ls_number_parameters 401 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.0965 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.07691(4) -0.10960(2) 0.55609(6) 0.03673(17) Uani 1 1 d . . . I2 I 0.36690(4) 0.117863(19) 0.13435(6) 0.03530(17) Uani 1 1 d . . . I3 I 0.21408(6) 0.208121(17) 0.10738(8) 0.03324(14) Uani 1 1 d . . . F1 F -0.1219(5) -0.0922(2) 0.6942(8) 0.0513(16) Uani 1 1 d . . . F2 F -0.2226(5) -0.0204(2) 0.7489(9) 0.0630(19) Uani 1 1 d . . . F3 F -0.1579(6) 0.0590(2) 0.6567(9) 0.071(2) Uani 1 1 d . . . F4 F 0.0040(5) 0.06442(19) 0.5074(9) 0.0596(18) Uani 1 1 d . . . F5 F 0.5635(5) 0.10588(19) -0.0225(8) 0.0491(16) Uani 1 1 d . . . F6 F 0.6754(5) 0.0382(2) -0.0688(9) 0.0597(18) Uani 1 1 d . . . F7 F 0.6292(6) -0.0423(2) 0.0334(9) 0.068(2) Uani 1 1 d . . . F8 F 0.4679(5) -0.05308(18) 0.1873(8) 0.0538(17) Uani 1 1 d . . . C1 C 0.1171(8) -0.0063(3) 0.4470(13) 0.038(2) Uani 1 1 d . . . C2 C 0.1898(8) 0.0000(3) 0.3836(12) 0.034(2) Uani 1 1 d . . . C3 C 0.2738(8) 0.0073(3) 0.3111(13) 0.038(2) Uani 1 1 d . . . C4 C 0.3445(8) 0.0144(3) 0.2483(12) 0.034(2) Uani 1 1 d . . . C5 C 0.0295(8) -0.0118(3) 0.5219(12) 0.035(2) Uani 1 1 d . . . C6 C -0.0049(7) -0.0524(3) 0.5717(12) 0.031(2) Uani 1 1 d . . . C7 C -0.0873(8) -0.0540(3) 0.6447(13) 0.041(2) Uani 1 1 d . . . C8 C -0.1410(8) -0.0170(4) 0.6745(14) 0.048(3) Uani 1 1 d . . . C9 C -0.1107(10) 0.0228(4) 0.6275(15) 0.053(3) Uani 1 1 d . . . C10 C -0.0270(8) 0.0249(3) 0.5515(13) 0.043(3) Uani 1 1 d . . . C11 C 0.4292(8) 0.0219(3) 0.1700(11) 0.033(2) Uani 1 1 d . . . C12 C 0.4551(8) 0.0627(3) 0.1110(13) 0.035(2) Uani 1 1 d . . . C13 C 0.5375(7) 0.0674(3) 0.0330(12) 0.036(2) Uani 1 1 d . . . C14 C 0.5946(8) 0.0324(3) 0.0082(13) 0.044(3) Uani 1 1 d . . . C15 C 0.5714(9) -0.0080(4) 0.0580(15) 0.043(3) Uani 1 1 d . . . C16 C 0.4905(8) -0.0130(3) 0.1380(12) 0.040(3) Uani 1 1 d . . . N1 N 0.0397(5) 0.2317(2) 0.5993(8) 0.0286(16) Uani 1 1 d . . . C17 C -0.0300(7) 0.2577(3) 0.4840(11) 0.036(2) Uani 1 1 d . . . H17A H -0.0579 0.2813 0.5454 0.044 Uiso 1 1 calc R . . H17B H -0.0845 0.2385 0.4422 0.044 Uiso 1 1 calc R . . C18 C 0.0128(8) 0.2780(3) 0.3413(12) 0.043(2) Uani 1 1 d . . . H18A H 0.0481 0.2557 0.2852 0.052 Uiso 1 1 calc R . . H18B H 0.0597 0.3011 0.3792 0.052 Uiso 1 1 calc R . . C19 C -0.0700(10) 0.2972(4) 0.2257(15) 0.066(4) Uani 1 1 d . . . H19A H -0.1129 0.2735 0.1805 0.079 Uiso 1 1 calc R . . H19B H -0.1096 0.3169 0.2861 0.079 Uiso 1 1 calc R . . C20 C -0.0336(12) 0.3214(6) 0.0938(18) 0.095(6) Uani 1 1 d . . . H20A H -0.0885 0.3348 0.0274 0.142 Uiso 1 1 calc R . . H20B H 0.0007 0.3015 0.0278 0.142 Uiso 1 1 calc R . . H20C H 0.0115 0.3441 0.1381 0.142 Uiso 1 1 calc R . . C21 C -0.0115(6) 0.2202(3) 0.7446(11) 0.035(2) Uani 1 1 d . . . H21A H -0.0358 0.2474 0.7894 0.042 Uiso 1 1 calc R . . H21B H 0.0372 0.2075 0.8274 0.042 Uiso 1 1 calc R . . C22 C -0.0967(8) 0.1886(3) 0.7147(12) 0.041(2) Uani 1 1 d . . . H22A H -0.1422 0.1986 0.6224 0.049 Uiso 1 1 calc R . . H22B H -0.0723 0.1594 0.6885 0.049 Uiso 1 1 calc R . . C23 C -0.1497(7) 0.1859(4) 0.8652(13) 0.045(3) Uani 1 1 d . . . H23A H -0.1027 0.1776 0.9581 0.054 Uiso 1 1 calc R . . H23B H -0.1763 0.2149 0.8877 0.054 Uiso 1 1 calc R . . C24 C -0.2322(10) 0.1531(5) 0.8458(17) 0.070(4) Uani 1 1 d . . . H24A H -0.2689 0.1545 0.9396 0.105 Uiso 1 1 calc R . . H24B H -0.2052 0.1239 0.8369 0.105 Uiso 1 1 calc R . . H24C H -0.2758 0.1598 0.7484 0.105 Uiso 1 1 calc R . . C25 C 0.1302(6) 0.2590(3) 0.6573(11) 0.033(2) Uani 1 1 d . . . H25A H 0.1708 0.2420 0.7399 0.039 Uiso 1 1 calc R . . H25B H 0.1688 0.2630 0.5653 0.039 Uiso 1 1 calc R . . C26 C 0.1130(8) 0.3033(3) 0.7269(13) 0.046(2) Uani 1 1 d . . . H26A H 0.0838 0.3227 0.6402 0.055 Uiso 1 1 calc R . . H26B H 0.0660 0.3006 0.8078 0.055 Uiso 1 1 calc R . . C27 C 0.2056(9) 0.3232(3) 0.8044(13) 0.049(3) Uani 1 1 d . . . H27A H 0.2533 0.3244 0.7243 0.059 Uiso 1 1 calc R . . H27B H 0.2331 0.3041 0.8933 0.059 Uiso 1 1 calc R . . C28 C 0.1929(11) 0.3686(4) 0.8707(15) 0.063(4) Uani 1 1 d . . . H28A H 0.2549 0.3785 0.9274 0.095 Uiso 1 1 calc R . . H28B H 0.1430 0.3681 0.9455 0.095 Uiso 1 1 calc R . . H28C H 0.1727 0.3885 0.7818 0.095 Uiso 1 1 calc R . . C29 C 0.0748(7) 0.1917(3) 0.5186(10) 0.032(2) Uani 1 1 d . . . H29A H 0.1123 0.2013 0.4305 0.039 Uiso 1 1 calc R . . H29B H 0.0169 0.1757 0.4688 0.039 Uiso 1 1 calc R . . C30 C 0.1376(8) 0.1604(3) 0.6246(12) 0.042(2) Uani 1 1 d . . . H30A H 0.1856 0.1769 0.6975 0.050 Uiso 1 1 calc R . . H30B H 0.0960 0.1435 0.6914 0.050 Uiso 1 1 calc R . . C31 C 0.1907(8) 0.1297(3) 0.5243(11) 0.038(2) Uani 1 1 d . . . H31A H 0.2338 0.1465 0.4602 0.045 Uiso 1 1 calc R . . H31B H 0.1427 0.1140 0.4486 0.045 Uiso 1 1 calc R . . C32 C 0.2516(8) 0.0969(3) 0.6281(13) 0.046(3) Uani 1 1 d . . . H32A H 0.2907 0.0796 0.5604 0.070 Uiso 1 1 calc R . . H32B H 0.2084 0.0776 0.6809 0.070 Uiso 1 1 calc R . . H32C H 0.2950 0.1123 0.7099 0.070 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 0.0342(4) 0.0381(3) 0.0386(4) -0.0063(3) 0.0071(3) 0.0037(3) I2 0.0320(3) 0.0323(3) 0.0423(4) -0.0035(3) 0.0072(3) 0.0005(3) I3 0.0359(3) 0.0280(3) 0.0361(3) 0.0032(3) 0.0052(2) -0.0004(3) F1 0.046(4) 0.055(4) 0.057(4) 0.002(3) 0.020(3) -0.005(3) F2 0.040(4) 0.083(5) 0.070(4) -0.006(4) 0.020(3) 0.018(4) F3 0.071(5) 0.053(4) 0.089(6) -0.015(4) 0.006(4) 0.028(4) F4 0.066(5) 0.033(3) 0.078(5) 0.005(3) -0.002(4) 0.004(3) F5 0.044(4) 0.042(3) 0.063(4) 0.001(3) 0.017(3) -0.006(3) F6 0.056(4) 0.066(4) 0.062(4) -0.008(3) 0.031(3) 0.006(3) F7 0.070(5) 0.051(4) 0.086(5) -0.014(4) 0.015(4) 0.025(4) F8 0.065(5) 0.031(3) 0.065(4) 0.003(3) 0.004(3) 0.003(3) C1 0.043(6) 0.037(5) 0.035(6) -0.001(4) 0.002(5) 0.001(5) C2 0.041(6) 0.030(5) 0.031(6) 0.000(4) 0.001(4) 0.004(4) C3 0.034(6) 0.037(5) 0.042(6) -0.003(4) -0.005(5) -0.002(4) C4 0.035(6) 0.033(5) 0.034(6) 0.003(4) -0.003(4) -0.001(4) C5 0.040(6) 0.036(5) 0.027(5) 0.001(4) -0.005(4) 0.004(4) C6 0.024(5) 0.043(5) 0.027(5) -0.002(4) 0.008(4) 0.001(4) C7 0.042(6) 0.043(6) 0.038(6) 0.005(4) 0.009(5) 0.001(5) C8 0.028(6) 0.065(7) 0.050(7) -0.011(5) 0.007(5) 0.015(5) C9 0.070(10) 0.045(6) 0.041(6) -0.004(5) -0.006(6) -0.001(6) C10 0.041(6) 0.041(6) 0.045(6) 0.001(5) -0.003(5) -0.001(5) C11 0.046(6) 0.029(5) 0.025(5) -0.003(4) 0.007(4) -0.004(4) C12 0.034(6) 0.027(5) 0.046(6) -0.005(4) 0.008(4) -0.001(4) C13 0.032(5) 0.038(5) 0.039(6) -0.005(4) 0.012(4) -0.007(4) C14 0.046(7) 0.042(6) 0.044(7) -0.007(4) 0.012(5) 0.005(5) C15 0.032(6) 0.063(7) 0.036(6) -0.007(6) 0.007(4) 0.016(6) C16 0.057(7) 0.019(4) 0.043(6) -0.010(4) -0.005(5) -0.002(4) N1 0.027(4) 0.029(4) 0.031(4) 0.007(3) 0.010(3) 0.007(3) C17 0.039(5) 0.032(5) 0.038(5) 0.003(4) 0.008(4) 0.002(4) C18 0.051(6) 0.040(5) 0.040(6) 0.014(4) 0.008(5) 0.018(5) C19 0.074(9) 0.069(9) 0.058(8) 0.024(6) 0.016(6) 0.034(7) C20 0.099(12) 0.118(14) 0.071(10) 0.047(9) 0.030(8) 0.045(10) C21 0.024(5) 0.045(5) 0.039(5) 0.003(4) 0.013(4) 0.006(4) C22 0.047(6) 0.040(6) 0.038(6) -0.004(4) 0.011(4) 0.004(5) C23 0.038(6) 0.051(6) 0.050(6) 0.007(5) 0.022(5) 0.009(5) C24 0.058(8) 0.087(10) 0.070(9) -0.010(7) 0.032(7) -0.020(8) C25 0.031(5) 0.028(5) 0.039(5) 0.007(4) 0.004(4) 0.007(4) C26 0.051(7) 0.039(6) 0.048(6) -0.003(5) 0.009(5) 0.010(5) C27 0.061(7) 0.040(6) 0.047(6) 0.005(5) 0.003(5) -0.008(5) C28 0.089(10) 0.045(7) 0.057(8) -0.013(5) 0.017(7) -0.026(7) C29 0.038(5) 0.031(5) 0.029(5) 0.001(3) 0.009(4) 0.011(4) C30 0.057(7) 0.033(5) 0.036(6) 0.007(4) 0.010(5) 0.013(5) C31 0.057(7) 0.027(5) 0.030(5) -0.004(4) 0.007(4) 0.002(5) C32 0.058(8) 0.034(5) 0.048(7) 0.000(4) 0.007(5) 0.016(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 I1 C6 2.104(9) . ? I1 I3 3.5752(9) 2 ? I2 C12 2.112(10) . ? I2 I3 3.4797(8) . ? F1 C7 1.352(12) . ? F2 C8 1.348(12) . ? F3 C9 1.327(14) . ? F4 C10 1.353(12) . ? F5 C13 1.334(11) . ? F6 C14 1.358(12) . ? F7 C15 1.350(12) . ? F8 C16 1.348(11) . ? C1 C2 1.200(14) . ? C1 C5 1.431(15) . ? C2 C3 1.383(14) . ? C3 C4 1.178(14) . ? C4 C11 1.420(14) . ? C5 C10 1.409(15) . ? C5 C6 1.415(14) . ? C6 C7 1.349(13) . ? C7 C8 1.396(15) . ? C8 C9 1.365(16) . ? C9 C10 1.379(17) . ? C11 C12 1.409(13) . ? C11 C16 1.410(14) . ? C12 C13 1.379(13) . ? C13 C14 1.364(14) . ? C14 C15 1.363(15) . ? C15 C16 1.371(15) . ? N1 C29 1.508(11) . ? N1 C21 1.513(11) . ? N1 C17 1.515(12) . ? N1 C25 1.539(12) . ? C17 C18 1.523(13) . ? C18 C19 1.533(15) . ? C19 C20 1.465(18) . ? C21 C22 1.526(14) . ? C22 C23 1.526(13) . ? C23 C24 1.516(16) . ? C25 C26 1.512(13) . ? C26 C27 1.498(15) . ? C27 C28 1.523(15) . ? C29 C30 1.517(12) . ? C30 C31 1.505(13) . ? C31 C32 1.523(12) . ? 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 I1 I3 169.5(3) . 2 ? C12 I2 I3 171.0(3) . . ? C2 C1 C5 177.5(11) . . ? C1 C2 C3 179.7(13) . . ? C4 C3 C2 178.5(11) . . ? C3 C4 C11 178.4(12) . . ? C10 C5 C6 116.6(10) . . ? C10 C5 C1 119.4(9) . . ? C6 C5 C1 124.0(9) . . ? C7 C6 C5 119.4(9) . . ? C7 C6 I1 118.8(7) . . ? C5 C6 I1 121.5(7) . . ? C6 C7 F1 121.0(9) . . ? C6 C7 C8 122.8(10) . . ? F1 C7 C8 116.2(9) . . ? F2 C8 C9 120.1(10) . . ? F2 C8 C7 120.4(10) . . ? C9 C8 C7 119.6(10) . . ? F3 C9 C8 121.9(12) . . ? F3 C9 C10 119.7(11) . . ? C8 C9 C10 118.4(11) . . ? F4 C10 C9 118.3(10) . . ? F4 C10 C5 118.4(10) . . ? C9 C10 C5 123.3(10) . . ? C12 C11 C16 115.6(9) . . ? C12 C11 C4 124.0(9) . . ? C16 C11 C4 120.3(9) . . ? C13 C12 C11 121.0(9) . . ? C13 C12 I2 118.1(7) . . ? C11 C12 I2 120.9(7) . . ? F5 C13 C14 117.8(9) . . ? F5 C13 C12 121.7(9) . . ? C14 C13 C12 120.5(9) . . ? F6 C14 C15 119.8(9) . . ? F6 C14 C13 119.1(9) . . ? C15 C14 C13 121.1(10) . . ? F7 C15 C14 120.3(10) . . ? F7 C15 C16 120.8(10) . . ? C14 C15 C16 118.8(9) . . ? F8 C16 C15 118.6(9) . . ? F8 C16 C11 118.3(9) . . ? C15 C16 C11 123.0(9) . . ? C29 N1 C21 111.7(7) . . ? C29 N1 C17 111.1(7) . . ? C21 N1 C17 108.4(6) . . ? C29 N1 C25 107.4(7) . . ? C21 N1 C25 107.9(7) . . ? C17 N1 C25 110.3(7) . . ? N1 C17 C18 116.2(8) . . ? C17 C18 C19 109.1(9) . . ? C20 C19 C18 112.2(12) . . ? N1 C21 C22 115.9(8) . . ? C23 C22 C21 109.2(8) . . ? C24 C23 C22 111.6(10) . . ? C26 C25 N1 117.3(8) . . ? C27 C26 C25 111.8(9) . . ? C26 C27 C28 113.9(11) . . ? N1 C29 C30 116.6(7) . . ? C31 C30 C29 110.8(8) . . ? C30 C31 C32 111.7(8) . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 1.131 _refine_diff_density_min -1.462 _refine_diff_density_rms 0.138