Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'William Pennington' _publ_contact_author_email BILLP@CLEMSON.EDU _publ_section_title ; Complementary Halogen and Hydrogen Bonding: Sulfur***Iodine Interactions and Thioamide Ribbons ; loop_ _publ_author_name 'William Pennington' 'Hadi D Arman' 'Rebecca L. Gieseking' 'Timothy W. Hanks' # Attachment 'CCDC7245881.cif' data_cd1963a _database_code_depnum_ccdc_archive 'CCDC 724588' #TrackingRef 'CCDC7245881.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'thiourea-1,4-diiodo-2,3,5,6-tetrafluorobenzene (1/1)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H4 F4 I2 N2 S' _chemical_formula_weight 477.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 11.6519(18) _cell_length_b 8.6561(14) _cell_length_c 23.639(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.057(6) _cell_angle_gamma 90.00 _cell_volume 2383.8(7) _cell_formula_units_Z 8 _cell_measurement_temperature 163.1500 _cell_measurement_reflns_used 15113 _cell_measurement_theta_min 2.5051 _cell_measurement_theta_max 26.3714 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max .3 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1744 _exptl_absorpt_coefficient_mu 5.477 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.6279 _exptl_absorpt_process_details ? _exptl_special_details ; REQABA Empirical Absorption Correction, Version 1.1, R.A. Jacobson, Molecular Structure Corp., The Woodlands, TX, 1998. ; _diffrn_ambient_temperature 163.1500 _diffrn_source_power 2.0000 _diffrn_source_voltage 50.0000 _diffrn_source_current 40.0000 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury CCD (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6199 _diffrn_measurement_method dtprofit.ref _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_measurement_details ; scan: Number of images: 360 Slice: -90.0000 - 90.0000 Image width: 0.5000 Exp time: 25.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 0.0000 XTD: 27.8225 2theta: -0.0826 scan: Number of images: 120 Slice: -30.0000 - 30.0000 Image width: 0.5000 Exp time: 25.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 90.0000 XTD: 27.8225 2theta: -0.0826 ; _diffrn_measurement_device_details ; AFC8: Eulerian 3-circle ; _diffrn_standards_number NA _diffrn_standards_interval_count NA _diffrn_standards_interval_time NA _diffrn_standards_decay_% NA _diffrn_reflns_number 20285 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4863 _reflns_number_gt 4098 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear, V. 1.3 sp1 (Rigaku Corp., 2001)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2001)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2001)' _computing_structure_solution 'SHELXTL,VERSION 6.10 Sheldrick (2000)' _computing_structure_refinement 'SHELXTL,VERSION 6.10' _computing_molecular_graphics 'SHELXTL,VERSION 6.10' _computing_publication_material 'SHELXTL,VERSION 6.10' _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^)+(0.0021P)^2^+23.8126P] 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 calc _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4863 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.0979 _refine_ls_wR_factor_gt 0.0934 _refine_ls_goodness_of_fit_ref 1.189 _refine_ls_restrained_S_all 1.189 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.34584(4) 0.62227(6) 0.37944(2) 0.02660(13) Uani 1 1 d . . . I2 I 0.08474(5) 0.60603(6) 0.13764(2) 0.03551(15) Uani 1 1 d . . . I3 I 0.89987(5) 0.65088(6) 0.35860(2) 0.03025(14) Uani 1 1 d . . . I4 I 1.15354(4) 0.86623(6) 0.617176(19) 0.02514(12) Uani 1 1 d . . . S1 S 0.20706(16) 0.7329(2) 0.26097(8) 0.0231(4) Uani 1 1 d . . . S2 S 0.78730(16) 0.5449(2) 0.23613(8) 0.0240(4) Uani 1 1 d . . . F1 F 0.3069(4) 0.6711(6) 0.5117(2) 0.0328(10) Uani 1 1 d . . . F2 F 0.4154(4) 0.5649(6) 0.6031(2) 0.0357(11) Uani 1 1 d . . . F3 F 0.1614(4) 0.7220(5) 0.0160(2) 0.0347(11) Uani 1 1 d . . . F4 F 0.1006(4) 0.6404(6) -0.0889(2) 0.0391(12) Uani 1 1 d . . . F5 F 1.1054(4) 0.8828(6) 0.39150(19) 0.0351(11) Uani 1 1 d . . . F6 F 1.1985(4) 0.9643(6) 0.4898(2) 0.0353(11) Uani 1 1 d . . . F7 F 0.9286(4) 0.6585(6) 0.5863(2) 0.0364(11) Uani 1 1 d . . . F8 F 0.8379(4) 0.5700(6) 0.4874(2) 0.0356(11) Uani 1 1 d . . . N1 N 0.3851(6) 0.8628(7) 0.2122(3) 0.0289(14) Uani 1 1 d . . . H1A H 0.4477 0.8619 0.1934 0.035 Uiso 1 1 calc R . . H1B H 0.3568 0.9491 0.2234 0.035 Uiso 1 1 calc R . . N2 N 0.3775(6) 0.6010(8) 0.2063(3) 0.0299(14) Uani 1 1 d . . . H2A H 0.4401 0.6023 0.1876 0.036 Uiso 1 1 calc R . . H2B H 0.3444 0.5145 0.2135 0.036 Uiso 1 1 calc R . . N3 N 0.6107(6) 0.6769(7) 0.2863(3) 0.0291(14) Uani 1 1 d . . . H3A H 0.5441 0.6777 0.3014 0.035 Uiso 1 1 calc R . . H3B H 0.6479 0.7619 0.2822 0.035 Uiso 1 1 calc R . . N4 N 0.5997(6) 0.4166(8) 0.2754(3) 0.0297(15) Uani 1 1 d . . . H4A H 0.5330 0.4169 0.2905 0.036 Uiso 1 1 calc R . . H4B H 0.6293 0.3310 0.2643 0.036 Uiso 1 1 calc R . . C1 C 0.4411(6) 0.5531(9) 0.4509(3) 0.0238(15) Uani 1 1 d . . . C2 C 0.4015(6) 0.5857(9) 0.5050(3) 0.0236(15) Uani 1 1 d . . . C3 C 0.4596(7) 0.5327(9) 0.5527(3) 0.0277(17) Uani 1 1 d . . . C4 C 0.0319(7) 0.5422(9) 0.0554(3) 0.0280(17) Uani 1 1 d . . . C5 C 0.0810(6) 0.6108(9) 0.0087(4) 0.0271(16) Uani 1 1 d . . . C6 C 0.0507(7) 0.5695(9) -0.0459(4) 0.0272(16) Uani 1 1 d . . . C7 C 0.9701(7) 0.7212(8) 0.4366(3) 0.0240(16) Uani 1 1 d . . . C8 C 1.0618(6) 0.8230(9) 0.4390(3) 0.0241(15) Uani 1 1 d . . . C9 C 1.1095(6) 0.8650(8) 0.4898(3) 0.0219(14) Uani 1 1 d . . . C10 C 1.0684(6) 0.8110(8) 0.5409(3) 0.0204(15) Uani 1 1 d . . . C11 C 0.9745(6) 0.7140(8) 0.5387(3) 0.0214(15) Uani 1 1 d . . . C12 C 0.9275(6) 0.6682(9) 0.4874(3) 0.0230(15) Uani 1 1 d . . . C13 C 0.3323(7) 0.7310(8) 0.2239(3) 0.0228(15) Uani 1 1 d . . . C14 C 0.6557(7) 0.5457(9) 0.2694(3) 0.0230(15) 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 I1 0.0249(2) 0.0297(3) 0.0250(2) 0.00298(19) -0.00288(19) -0.0012(2) I2 0.0400(3) 0.0313(3) 0.0348(3) -0.0059(2) -0.0102(2) 0.0111(2) I3 0.0342(3) 0.0296(3) 0.0265(2) -0.0061(2) -0.0113(2) 0.0071(2) I4 0.0244(2) 0.0300(3) 0.0208(2) -0.00555(19) -0.00313(19) 0.00342(19) S1 0.0259(9) 0.0184(8) 0.0251(9) -0.0010(7) 0.0049(8) 0.0001(7) S2 0.0252(9) 0.0237(9) 0.0232(9) -0.0021(7) -0.0009(8) -0.0004(7) F1 0.029(2) 0.035(3) 0.035(2) -0.002(2) 0.002(2) 0.006(2) F2 0.037(3) 0.043(3) 0.027(2) -0.004(2) 0.006(2) 0.007(2) F3 0.024(2) 0.023(2) 0.057(3) -0.004(2) -0.005(2) -0.0040(18) F4 0.038(3) 0.035(3) 0.045(3) 0.008(2) 0.001(2) 0.004(2) F5 0.035(3) 0.047(3) 0.024(2) 0.014(2) -0.0004(19) -0.008(2) F6 0.028(3) 0.037(3) 0.041(3) 0.006(2) -0.004(2) -0.014(2) F7 0.037(3) 0.045(3) 0.028(2) 0.007(2) 0.002(2) -0.008(2) F8 0.029(3) 0.034(3) 0.043(3) 0.004(2) -0.006(2) -0.013(2) N1 0.037(4) 0.020(3) 0.030(3) -0.002(3) 0.013(3) -0.005(3) N2 0.029(3) 0.024(3) 0.037(4) -0.006(3) 0.009(3) -0.003(3) N3 0.031(4) 0.023(3) 0.034(4) -0.003(3) 0.009(3) -0.003(3) N4 0.033(4) 0.024(3) 0.032(4) -0.001(3) 0.007(3) -0.005(3) C1 0.021(4) 0.023(4) 0.026(4) 0.002(3) -0.002(3) -0.007(3) C2 0.015(3) 0.021(3) 0.035(4) 0.004(3) 0.002(3) -0.002(3) C3 0.037(5) 0.025(4) 0.021(4) 0.003(3) 0.000(3) -0.004(3) C4 0.025(4) 0.026(4) 0.033(4) 0.003(3) -0.011(3) 0.009(3) C5 0.019(3) 0.020(3) 0.042(4) -0.008(3) -0.004(3) 0.006(3) C6 0.023(4) 0.024(4) 0.034(4) 0.002(3) 0.003(3) 0.006(3) C7 0.025(4) 0.021(3) 0.026(4) -0.007(3) -0.009(3) 0.009(3) C8 0.022(4) 0.023(4) 0.027(4) 0.002(3) -0.001(3) 0.005(3) C9 0.019(3) 0.020(3) 0.027(4) 0.002(3) -0.005(3) -0.001(3) C10 0.024(4) 0.022(3) 0.015(3) -0.005(3) -0.010(3) 0.002(3) C11 0.021(4) 0.022(3) 0.021(3) 0.005(3) 0.001(3) 0.005(3) C12 0.015(3) 0.025(4) 0.029(4) -0.003(3) -0.003(3) -0.004(3) C13 0.029(4) 0.018(3) 0.021(3) -0.005(3) -0.006(3) 0.001(3) C14 0.028(4) 0.028(4) 0.014(3) 0.000(3) -0.004(3) -0.002(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.092(7) . ? I1 C2 3.042(8) . ? I1 C3 3.063(8) 3_666 ? I1 S1 3.3480(19) . ? I1 N3 3.853(7) . ? I1 N1 4.095(7) 2_545 ? I2 C4 2.102(8) . ? I2 C5 3.047(8) . ? I2 C6 3.062(8) 3_565 ? I2 S1 3.4036(19) . ? I2 N2 3.750(7) . ? I2 N4 4.029(7) 2 ? I3 C7 2.095(7) . ? I3 C8 3.043(8) . ? I3 C12 3.060(8) . ? I3 S2 3.2867(19) . ? I3 N3 3.757(7) . ? I3 N4 3.914(7) 2_655 ? I3 N1 3.931(7) 2_645 ? I4 C10 2.096(6) . ? I4 C9 3.046(7) . ? I4 C11 3.063(7) . ? I4 S2 3.2812(19) 4_676 ? I4 N2 3.888(7) 4_676 ? I4 N3 4.055(7) 4_676 ? S1 C13 1.716(9) . ? S1 N1 2.643(7) . ? S1 N2 2.648(7) . ? S1 N2 3.427(7) 2 ? S1 N1 3.442(7) 2_545 ? S1 N4 3.990(7) 2 ? S2 C14 1.736(8) . ? S2 N4 2.636(7) . ? S2 N3 2.652(7) . ? S2 I4 3.2812(19) 4_575 ? S2 N3 3.444(7) 2_645 ? S2 N4 3.489(7) 2_655 ? F1 C2 1.340(9) . ? F2 C3 1.336(10) . ? F2 N4 2.886(8) 3_666 ? F3 C5 1.352(9) . ? F4 C6 1.330(10) . ? F5 C8 1.344(9) . ? F6 C9 1.347(8) . ? F7 C11 1.342(9) . ? F8 C12 1.346(8) . ? N1 C13 1.328(10) . ? N1 N2 2.273(9) . ? N1 S1 3.442(7) 2 ? N1 N3 3.520(10) . ? N1 I3 3.931(7) 2_655 ? N1 I1 4.095(7) 2 ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N2 C13 1.313(10) . ? N2 N3 3.347(9) . ? N2 S1 3.427(7) 2_545 ? N2 N4 3.430(10) . ? N2 I4 3.888(7) 4_575 ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? N3 C14 1.316(10) . ? N3 N4 2.272(9) . ? N3 S2 3.444(7) 2_655 ? N3 I4 4.055(7) 4_575 ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? N4 C14 1.303(10) . ? N4 F2 2.886(8) 3_666 ? N4 S2 3.489(7) 2_645 ? N4 I3 3.914(7) 2_645 ? N4 S1 3.990(7) 2_545 ? N4 I2 4.029(7) 2_545 ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? C1 C3 1.379(11) 3_666 ? C1 C2 1.395(11) . ? C2 C3 1.383(10) . ? C3 C1 1.379(11) 3_666 ? C3 I1 3.063(8) 3_666 ? C4 C6 1.380(11) 3_565 ? C4 C5 1.385(12) . ? C5 C6 1.380(11) . ? C6 C4 1.380(11) 3_565 ? C6 I2 3.062(8) 3_565 ? C7 C12 1.385(11) . ? C7 C8 1.386(11) . ? C8 C9 1.363(10) . ? C9 C10 1.390(11) . ? C10 C11 1.379(10) . ? C11 C12 1.380(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 I1 C2 23.4(3) . . ? C1 I1 C3 22.3(3) . 3_666 ? C2 I1 C3 45.6(2) . 3_666 ? C1 I1 S1 176.8(2) . . ? C2 I1 S1 159.51(15) . . ? C3 I1 S1 154.83(16) 3_666 . ? C1 I1 N3 94.5(2) . . ? C2 I1 N3 114.31(17) . . ? C3 I1 N3 76.13(19) 3_666 . ? S1 I1 N3 82.32(11) . . ? C1 I1 N1 127.2(2) . 2_545 ? C2 I1 N1 125.81(16) . 2_545 ? C3 I1 N1 120.67(17) 3_666 2_545 ? S1 I1 N1 53.97(9) . 2_545 ? N3 I1 N1 106.89(14) . 2_545 ? C4 I2 C5 23.1(3) . . ? C4 I2 C6 22.5(3) . 3_565 ? C5 I2 C6 45.6(2) . 3_565 ? C4 I2 S1 171.0(2) . . ? C5 I2 S1 148.24(15) . . ? C6 I2 S1 165.70(16) 3_565 . ? C4 I2 N2 130.2(2) . . ? C5 I2 N2 115.41(18) . . ? C6 I2 N2 138.89(18) 3_565 . ? S1 I2 N2 43.11(11) . . ? C4 I2 N4 119.8(2) . 2 ? C5 I2 N4 120.22(16) . 2 ? C6 I2 N4 114.81(17) 3_565 2 ? S1 I2 N4 64.30(10) . 2 ? N2 I2 N4 106.04(14) . 2 ? C7 I3 C8 23.1(3) . . ? C7 I3 C12 22.6(3) . . ? C8 I3 C12 45.7(2) . . ? C7 I3 S2 179.2(2) . . ? C8 I3 S2 156.86(16) . . ? C12 I3 S2 157.39(14) . . ? C7 I3 N3 135.7(2) . . ? C8 I3 N3 142.69(17) . . ? C12 I3 N3 121.79(17) . . ? S2 I3 N3 43.61(11) . . ? C7 I3 N4 122.4(2) . 2_655 ? C8 I3 N4 101.98(18) . 2_655 ? C12 I3 N4 140.79(17) . 2_655 ? S2 I3 N4 57.16(10) . 2_655 ? N3 I3 N4 67.12(15) . 2_655 ? C7 I3 N1 108.5(2) . 2_645 ? C8 I3 N1 100.60(18) . 2_645 ? C12 I3 N1 113.50(17) . 2_645 ? S2 I3 N1 72.24(10) . 2_645 ? N3 I3 N1 114.68(14) . 2_645 ? N4 I3 N1 91.02(14) 2_655 2_645 ? C10 I4 C9 23.2(3) . . ? C10 I4 C11 22.4(3) . . ? C9 I4 C11 45.53(19) . . ? C10 I4 S2 179.6(2) . 4_676 ? C9 I4 S2 156.48(14) . 4_676 ? C11 I4 S2 157.98(15) . 4_676 ? C10 I4 N2 95.7(2) . 4_676 ? C9 I4 N2 114.20(17) . 4_676 ? C11 I4 N2 78.37(18) . 4_676 ? S2 I4 N2 84.45(11) 4_676 4_676 ? C10 I4 N3 139.6(2) . 4_676 ? C9 I4 N3 162.35(17) . 4_676 ? C11 I4 N3 117.54(17) . 4_676 ? S2 I4 N3 40.70(10) 4_676 4_676 ? N2 I4 N3 49.80(14) 4_676 4_676 ? C13 S1 N1 25.8(3) . . ? C13 S1 N2 25.1(3) . . ? N1 S1 N2 50.9(2) . . ? C13 S1 I1 91.3(2) . . ? N1 S1 I1 96.64(16) . . ? N2 S1 I1 85.98(16) . . ? C13 S1 I2 84.6(2) . . ? N1 S1 I2 94.78(15) . . ? N2 S1 I2 75.44(15) . . ? I1 S1 I2 144.33(6) . . ? C13 S1 N2 112.0(3) . 2 ? N1 S1 N2 86.24(19) . 2 ? N2 S1 N2 137.09(19) . 2 ? I1 S1 N2 102.32(12) . 2 ? I2 S1 N2 112.08(12) . 2 ? C13 S1 N1 110.9(3) . 2_545 ? N1 S1 N1 136.59(18) . 2_545 ? N2 S1 N1 85.86(19) . 2_545 ? I1 S1 N1 74.16(12) . 2_545 ? I2 S1 N1 74.35(12) . 2_545 ? N2 S1 N1 137.03(17) 2 2_545 ? C13 S1 N4 131.3(3) . 2 ? N1 S1 N4 116.35(19) . 2 ? N2 S1 N4 138.01(19) . 2 ? I1 S1 N4 135.31(11) . 2 ? I2 S1 N4 65.47(10) . 2 ? N2 S1 N4 54.44(15) 2 2 ? N1 S1 N4 97.42(16) 2_545 2 ? C14 S2 N4 25.4(3) . . ? C14 S2 N3 25.5(3) . . ? N4 S2 N3 50.9(2) . . ? C14 S2 I4 88.7(2) . 4_575 ? N4 S2 I4 90.95(15) . 4_575 ? N3 S2 I4 85.52(15) . 4_575 ? C14 S2 I3 86.7(2) . . ? N4 S2 I3 97.34(16) . . ? N3 S2 I3 77.67(15) . . ? I4 S2 I3 149.88(6) 4_575 . ? C14 S2 N3 112.5(3) . 2_645 ? N4 S2 N3 87.43(19) . 2_645 ? N3 S2 N3 137.72(19) . 2_645 ? I4 S2 N3 104.16(12) 4_575 2_645 ? I3 S2 N3 105.09(12) . 2_645 ? C14 S2 N4 111.7(3) . 2_655 ? N4 S2 N4 137.13(18) . 2_655 ? N3 S2 N4 86.26(19) . 2_655 ? I4 S2 N4 83.74(12) 4_575 2_655 ? I3 S2 N4 70.51(11) . 2_655 ? N3 S2 N4 135.15(17) 2_645 2_655 ? C3 F2 N4 158.6(5) . 3_666 ? C13 N1 N2 30.5(4) . . ? C13 N1 S1 34.2(4) . . ? N2 N1 S1 64.7(2) . . ? C13 N1 S1 127.9(5) . 2 ? N2 N1 S1 158.1(3) . 2 ? S1 N1 S1 93.7(2) . 2 ? C13 N1 N3 81.3(4) . . ? N2 N1 N3 66.6(3) . . ? S1 N1 N3 100.0(2) . . ? S1 N1 N3 124.5(2) 2 . ? C13 N1 I3 159.3(5) . 2_655 ? N2 N1 I3 129.1(3) . 2_655 ? S1 N1 I3 165.3(2) . 2_655 ? S1 N1 I3 72.03(12) 2 2_655 ? N3 N1 I3 91.49(19) . 2_655 ? C13 N1 I1 106.2(5) . 2 ? N2 N1 I1 119.3(3) . 2 ? S1 N1 I1 87.16(18) . 2 ? S1 N1 I1 51.87(10) 2 2 ? N3 N1 I1 172.4(2) . 2 ? I3 N1 I1 81.06(12) 2_655 2 ? C13 N1 H1A 120.0 . . ? N2 N1 H1A 89.5 . . ? S1 N1 H1A 154.2 . . ? S1 N1 H1A 112.0 2 . ? N3 N1 H1A 67.7 . . ? I3 N1 H1A 40.0 2_655 . ? I1 N1 H1A 106.7 2 . ? C13 N1 H1B 120.0 . . ? N2 N1 H1B 150.5 . . ? S1 N1 H1B 85.8 . . ? S1 N1 H1B 9.0 2 . ? N3 N1 H1B 122.1 . . ? I3 N1 H1B 80.3 2_655 . ? I1 N1 H1B 55.5 2 . ? H1A N1 H1B 120.0 . . ? C13 N2 N1 30.8(4) . . ? C13 N2 S1 33.6(4) . . ? N1 N2 S1 64.5(3) . . ? C13 N2 N3 88.8(5) . . ? N1 N2 N3 74.9(3) . . ? S1 N2 N3 104.3(2) . . ? C13 N2 S1 127.3(5) . 2_545 ? N1 N2 S1 157.6(3) . 2_545 ? S1 N2 S1 94.0(2) . 2_545 ? N3 N2 S1 106.8(2) . 2_545 ? C13 N2 N4 123.5(5) . . ? N1 N2 N4 114.0(3) . . ? S1 N2 N4 122.3(3) . . ? N3 N2 N4 39.15(17) . . ? S1 N2 N4 71.18(17) 2_545 . ? C13 N2 I2 76.1(4) . . ? N1 N2 I2 92.8(3) . . ? S1 N2 I2 61.45(14) . . ? N3 N2 I2 164.7(2) . . ? S1 N2 I2 81.13(14) 2_545 . ? N4 N2 I2 152.1(2) . . ? C13 N2 I4 116.7(5) . 4_575 ? N1 N2 I4 85.9(3) . 4_575 ? S1 N2 I4 150.3(2) . 4_575 ? N3 N2 I4 67.69(17) . 4_575 ? S1 N2 I4 115.75(18) 2_545 4_575 ? N4 N2 I4 70.56(17) . 4_575 ? I2 N2 I4 121.31(18) . 4_575 ? C13 N2 H2A 120.0 . . ? N1 N2 H2A 89.2 . . ? S1 N2 H2A 153.6 . . ? N3 N2 H2A 66.4 . . ? S1 N2 H2A 112.3 2_545 . ? N4 N2 H2A 67.1 . . ? I2 N2 H2A 123.4 . . ? I4 N2 H2A 3.9 4_575 . ? C13 N2 H2B 120.0 . . ? N1 N2 H2B 150.8 . . ? S1 N2 H2B 86.4 . . ? N3 N2 H2B 114.9 . . ? S1 N2 H2B 9.9 2_545 . ? N4 N2 H2B 80.7 . . ? I2 N2 H2B 71.9 . . ? I4 N2 H2B 123.2 4_575 . ? H2A N2 H2B 120.0 . . ? C14 N3 N4 29.7(4) . . ? C14 N3 S2 34.5(4) . . ? N4 N3 S2 64.2(3) . . ? C14 N3 N2 89.0(4) . . ? N4 N3 N2 72.4(3) . . ? S2 N3 N2 106.9(2) . . ? C14 N3 S2 127.7(5) . 2_655 ? N4 N3 S2 156.8(4) . 2_655 ? S2 N3 S2 93.3(2) . 2_655 ? N2 N3 S2 111.9(2) . 2_655 ? C14 N3 N1 122.8(5) . . ? N4 N3 N1 110.9(3) . . ? S2 N3 N1 123.6(3) . . ? N2 N3 N1 38.54(17) . . ? S2 N3 N1 75.96(17) 2_655 . ? C14 N3 I3 74.2(4) . . ? N4 N3 I3 92.3(3) . . ? S2 N3 I3 58.72(14) . . ? N2 N3 I3 163.2(2) . . ? S2 N3 I3 79.42(14) 2_655 . ? N1 N3 I3 155.3(2) . . ? C14 N3 I1 113.3(5) . . ? N4 N3 I1 84.2(3) . . ? S2 N3 I1 147.0(2) . . ? N2 N3 I1 69.41(17) . . ? S2 N3 I1 118.93(18) 2_655 . ? N1 N3 I1 75.05(18) . . ? I3 N3 I1 116.97(17) . . ? C14 N3 I4 64.2(4) . 4_575 ? N4 N3 I4 78.7(2) . 4_575 ? S2 N3 I4 53.78(13) . 4_575 ? N2 N3 I4 62.51(16) . 4_575 ? S2 N3 I4 83.36(15) 2_655 4_575 ? N1 N3 I4 69.88(16) . 4_575 ? I3 N3 I4 108.51(17) . 4_575 ? I1 N3 I4 131.80(18) . 4_575 ? C14 N3 H3A 120.0 . . ? N4 N3 H3A 90.3 . . ? S2 N3 H3A 154.4 . . ? N2 N3 H3A 60.4 . . ? S2 N3 H3A 111.9 2_655 . ? N1 N3 H3A 62.1 . . ? I3 N3 H3A 128.3 . . ? I1 N3 H3A 13.0 . . ? I4 N3 H3A 122.6 4_575 . ? C14 N3 H3B 120.0 . . ? N4 N3 H3B 149.7 . . ? S2 N3 H3B 85.5 . . ? N2 N3 H3B 120.7 . . ? S2 N3 H3B 10.2 2_655 . ? N1 N3 H3B 85.8 . . ? I3 N3 H3B 69.6 . . ? I1 N3 H3B 125.4 . . ? I4 N3 H3B 84.1 4_575 . ? H3A N3 H3B 120.0 . . ? C14 N4 N3 30.0(4) . . ? C14 N4 S2 34.9(4) . . ? N3 N4 S2 64.9(3) . . ? C14 N4 F2 95.8(5) . 3_666 ? N3 N4 F2 80.6(3) . 3_666 ? S2 N4 F2 113.1(3) . 3_666 ? C14 N4 N2 85.6(5) . . ? N3 N4 N2 68.5(3) . . ? S2 N4 N2 105.1(2) . . ? F2 N4 N2 112.9(3) 3_666 . ? C14 N4 S2 126.3(5) . 2_645 ? N3 N4 S2 154.5(3) . 2_645 ? S2 N4 S2 92.5(2) . 2_645 ? F2 N4 S2 99.1(2) 3_666 2_645 ? N2 N4 S2 132.4(2) . 2_645 ? C14 N4 I3 114.0(5) . 2_645 ? N3 N4 I3 132.4(3) . 2_645 ? S2 N4 I3 87.09(19) . 2_645 ? F2 N4 I3 147.1(2) 3_666 2_645 ? N2 N4 I3 84.28(18) . 2_645 ? S2 N4 I3 52.33(10) 2_645 2_645 ? C14 N4 S1 140.0(5) . 2_545 ? N3 N4 S1 117.9(3) . 2_545 ? S2 N4 S1 146.9(2) . 2_545 ? F2 N4 S1 99.6(2) 3_666 2_545 ? N2 N4 S1 54.38(15) . 2_545 ? S2 N4 S1 87.35(14) 2_645 2_545 ? I3 N4 S1 66.82(11) 2_645 2_545 ? C14 N4 I2 154.2(5) . 2_545 ? N3 N4 I2 129.3(3) . 2_545 ? S2 N4 I2 156.1(2) . 2_545 ? F2 N4 I2 59.09(16) 3_666 2_545 ? N2 N4 I2 98.5(2) . 2_545 ? S2 N4 I2 68.30(12) 2_645 2_545 ? I3 N4 I2 91.70(13) 2_645 2_545 ? S1 N4 I2 50.23(9) 2_545 2_545 ? C14 N4 H4A 120.0 . . ? N3 N4 H4A 90.0 . . ? S2 N4 H4A 154.8 . . ? F2 N4 H4A 61.0 3_666 . ? N2 N4 H4A 61.1 . . ? S2 N4 H4A 112.4 2_645 . ? I3 N4 H4A 110.6 2_645 . ? S1 N4 H4A 43.9 2_545 . ? I2 N4 H4A 45.3 2_545 . ? C14 N4 H4B 120.0 . . ? N3 N4 H4B 150.0 . . ? S2 N4 H4B 85.1 . . ? F2 N4 H4B 112.6 3_666 . ? N2 N4 H4B 124.0 . . ? S2 N4 H4B 13.6 2_645 . ? I3 N4 H4B 40.6 2_645 . ? S1 N4 H4B 87.4 2_545 . ? I2 N4 H4B 78.6 2_545 . ? H4A N4 H4B 120.0 . . ? C3 C1 C2 117.2(7) 3_666 . ? C3 C1 I1 122.5(6) 3_666 . ? C2 C1 I1 120.2(6) . . ? F1 C2 C3 118.5(7) . . ? F1 C2 C1 120.5(7) . . ? C3 C2 C1 121.0(7) . . ? F1 C2 I1 84.1(4) . . ? C3 C2 I1 157.3(6) . . ? C1 C2 I1 36.5(4) . . ? F2 C3 C1 120.3(7) . 3_666 ? F2 C3 C2 117.9(7) . . ? C1 C3 C2 121.8(8) 3_666 . ? F2 C3 I1 85.3(4) . 3_666 ? C1 C3 I1 35.2(4) 3_666 3_666 ? C2 C3 I1 156.8(6) . 3_666 ? C6 C4 C5 117.9(7) 3_565 . ? C6 C4 I2 121.7(6) 3_565 . ? C5 C4 I2 120.4(6) . . ? F3 C5 C6 117.9(8) . . ? F3 C5 C4 120.0(7) . . ? C6 C5 C4 122.1(7) . . ? F3 C5 I2 83.4(4) . . ? C6 C5 I2 158.6(6) . . ? C4 C5 I2 36.5(4) . . ? F4 C6 C5 119.2(7) . . ? F4 C6 C4 120.8(7) . 3_565 ? C5 C6 C4 120.0(8) . 3_565 ? F4 C6 I2 85.1(4) . 3_565 ? C5 C6 I2 155.7(6) . 3_565 ? C4 C6 I2 35.7(4) 3_565 3_565 ? C12 C7 C8 117.7(6) . . ? C12 C7 I3 121.8(5) . . ? C8 C7 I3 120.5(6) . . ? F5 C8 C9 118.6(7) . . ? F5 C8 C7 121.0(7) . . ? C9 C8 C7 120.4(7) . . ? F5 C8 I3 84.6(4) . . ? C9 C8 I3 156.7(6) . . ? C7 C8 I3 36.4(4) . . ? F6 C9 C8 118.1(7) . . ? F6 C9 C10 119.5(6) . . ? C8 C9 C10 122.4(7) . . ? F6 C9 I4 83.2(4) . . ? C8 C9 I4 158.5(6) . . ? C10 C9 I4 36.4(3) . . ? C11 C10 C9 117.2(6) . . ? C11 C10 I4 122.3(5) . . ? C9 C10 I4 120.4(5) . . ? F7 C11 C10 120.9(6) . . ? F7 C11 C12 118.3(7) . . ? C10 C11 C12 120.7(7) . . ? F7 C11 I4 85.7(4) . . ? C10 C11 I4 35.4(3) . . ? C12 C11 I4 155.6(6) . . ? F8 C12 C11 118.5(7) . . ? F8 C12 C7 120.0(6) . . ? C11 C12 C7 121.5(7) . . ? F8 C12 I3 84.4(4) . . ? C11 C12 I3 157.1(5) . . ? C7 C12 I3 35.6(4) . . ? N2 C13 N1 118.7(7) . . ? N2 C13 S1 121.3(6) . . ? N1 C13 S1 120.0(6) . . ? N4 C14 N3 120.3(7) . . ? N4 C14 S2 119.6(6) . . ? N3 C14 S2 120.0(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 I1 S1 C13 1(4) . . . . ? C2 I1 S1 C13 151.7(5) . . . . ? C3 I1 S1 C13 -25.1(4) 3_666 . . . ? N3 I1 S1 C13 6.1(3) . . . . ? N1 I1 S1 C13 -111.3(3) 2_545 . . . ? C1 I1 S1 N1 -25(4) . . . . ? C2 I1 S1 N1 126.4(4) . . . . ? C3 I1 S1 N1 -50.4(4) 3_666 . . . ? N3 I1 S1 N1 -19.23(18) . . . . ? N1 I1 S1 N1 -136.65(18) 2_545 . . . ? C1 I1 S1 N2 25(4) . . . . ? C2 I1 S1 N2 176.3(4) . . . . ? C3 I1 S1 N2 -0.6(4) 3_666 . . . ? N3 I1 S1 N2 30.60(17) . . . . ? N1 I1 S1 N2 -86.83(19) 2_545 . . . ? C1 I1 S1 I2 83(4) . . . . ? C2 I1 S1 I2 -125.8(4) . . . . ? C3 I1 S1 I2 57.4(4) 3_666 . . . ? N3 I1 S1 I2 88.59(14) . . . . ? N1 I1 S1 I2 -28.84(15) 2_545 . . . ? C1 I1 S1 N2 -112(4) . . . 2 ? C2 I1 S1 N2 38.8(4) . . . 2 ? C3 I1 S1 N2 -138.0(4) 3_666 . . 2 ? N3 I1 S1 N2 -106.81(16) . . . 2 ? N1 I1 S1 N2 135.77(17) 2_545 . . 2 ? C1 I1 S1 N1 112(4) . . . 2_545 ? C2 I1 S1 N1 -96.9(4) . . . 2_545 ? C3 I1 S1 N1 86.3(4) 3_666 . . 2_545 ? N3 I1 S1 N1 117.42(15) . . . 2_545 ? C1 I1 S1 N4 -164(4) . . . 2 ? C2 I1 S1 N4 -12.4(4) . . . 2 ? C3 I1 S1 N4 170.8(4) 3_666 . . 2 ? N3 I1 S1 N4 -158.08(18) . . . 2 ? N1 I1 S1 N4 84.50(19) 2_545 . . 2 ? C4 I2 S1 C13 -21.0(13) . . . . ? C5 I2 S1 C13 -34.1(4) . . . . ? C6 I2 S1 C13 129.6(6) 3_565 . . . ? N2 I2 S1 C13 23.7(3) . . . . ? N4 I2 S1 C13 -140.6(3) 2 . . . ? C4 I2 S1 N1 2.7(13) . . . . ? C5 I2 S1 N1 -10.3(3) . . . . ? C6 I2 S1 N1 153.3(6) 3_565 . . . ? N2 I2 S1 N1 47.5(2) . . . . ? N4 I2 S1 N1 -116.8(2) 2 . . . ? C4 I2 S1 N2 -44.7(13) . . . . ? C5 I2 S1 N2 -57.8(3) . . . . ? C6 I2 S1 N2 105.8(6) 3_565 . . . ? N4 I2 S1 N2 -164.3(2) 2 . . . ? C4 I2 S1 I1 -105.6(13) . . . . ? C5 I2 S1 I1 -118.7(3) . . . . ? C6 I2 S1 I1 44.9(6) 3_565 . . . ? N2 I2 S1 I1 -60.92(18) . . . . ? N4 I2 S1 I1 134.78(16) 2 . . . ? C4 I2 S1 N2 90.6(13) . . . 2 ? C5 I2 S1 N2 77.5(3) . . . 2 ? C6 I2 S1 N2 -118.8(6) 3_565 . . 2 ? N2 I2 S1 N2 135.3(2) . . . 2 ? N4 I2 S1 N2 -28.96(17) 2 . . 2 ? C4 I2 S1 N1 -134.5(13) . . . 2_545 ? C5 I2 S1 N1 -147.5(3) . . . 2_545 ? C6 I2 S1 N1 16.1(6) 3_565 . . 2_545 ? N2 I2 S1 N1 -89.7(2) . . . 2_545 ? N4 I2 S1 N1 105.98(17) 2 . . 2_545 ? C4 I2 S1 N4 119.6(13) . . . 2 ? C5 I2 S1 N4 106.5(3) . . . 2 ? C6 I2 S1 N4 -89.9(6) 3_565 . . 2 ? N2 I2 S1 N4 164.3(2) . . . 2 ? C7 I3 S2 C14 -57(17) . . . . ? C8 I3 S2 C14 -142.6(4) . . . . ? C12 I3 S2 C14 33.7(5) . . . . ? N3 I3 S2 C14 -24.1(3) . . . . ? N4 I3 S2 C14 -114.4(3) 2_655 . . . ? N1 I3 S2 C14 142.3(3) 2_645 . . . ? C7 I3 S2 N4 -80(17) . . . . ? C8 I3 S2 N4 -165.8(4) . . . . ? C12 I3 S2 N4 10.5(4) . . . . ? N3 I3 S2 N4 -47.2(2) . . . . ? N4 I3 S2 N4 -137.58(19) 2_655 . . . ? N1 I3 S2 N4 119.18(19) 2_645 . . . ? C7 I3 S2 N3 -33(17) . . . . ? C8 I3 S2 N3 -118.6(4) . . . . ? C12 I3 S2 N3 57.7(4) . . . . ? N4 I3 S2 N3 -90.38(19) 2_655 . . . ? N1 I3 S2 N3 166.39(19) 2_645 . . . ? C7 I3 S2 I4 24(17) . . . 4_575 ? C8 I3 S2 I4 -61.0(4) . . . 4_575 ? C12 I3 S2 I4 115.3(4) . . . 4_575 ? N3 I3 S2 I4 57.58(19) . . . 4_575 ? N4 I3 S2 I4 -32.80(17) 2_655 . . 4_575 ? N1 I3 S2 I4 -136.03(17) 2_645 . . 4_575 ? C7 I3 S2 N3 -170(17) . . . 2_645 ? C8 I3 S2 N3 104.9(4) . . . 2_645 ? C12 I3 S2 N3 -78.8(4) . . . 2_645 ? N3 I3 S2 N3 -136.51(19) . . . 2_645 ? N4 I3 S2 N3 133.11(17) 2_655 . . 2_645 ? N1 I3 S2 N3 29.88(16) 2_645 . . 2_645 ? C7 I3 S2 N4 57(17) . . . 2_655 ? C8 I3 S2 N4 -28.2(4) . . . 2_655 ? C12 I3 S2 N4 148.1(4) . . . 2_655 ? N3 I3 S2 N4 90.38(19) . . . 2_655 ? N1 I3 S2 N4 -103.23(16) 2_645 . . 2_655 ? N2 S1 N1 C13 -0.2(6) . . . . ? I1 S1 N1 C13 79.1(6) . . . . ? I2 S1 N1 C13 -67.0(6) . . . . ? N2 S1 N1 C13 -178.9(6) 2 . . . ? N1 S1 N1 C13 5.2(6) 2_545 . . . ? N4 S1 N1 C13 -132.0(6) 2 . . . ? C13 S1 N1 N2 0.2(6) . . . . ? I1 S1 N1 N2 79.3(2) . . . . ? I2 S1 N1 N2 -66.8(2) . . . . ? N2 S1 N1 N2 -178.71(16) 2 . . . ? N1 S1 N1 N2 5.4(2) 2_545 . . . ? N4 S1 N1 N2 -131.8(2) 2 . . . ? C13 S1 N1 S1 176.2(7) . . . 2 ? N2 S1 N1 S1 176.0(3) . . . 2 ? I1 S1 N1 S1 -104.74(13) . . . 2 ? I2 S1 N1 S1 109.12(13) . . . 2 ? N2 S1 N1 S1 -2.76(16) 2 . . 2 ? N1 S1 N1 S1 -178.67(17) 2_545 . . 2 ? N4 S1 N1 S1 44.2(2) 2 . . 2 ? C13 S1 N1 N3 -57.8(6) . . . . ? N2 S1 N1 N3 -58.0(3) . . . . ? I1 S1 N1 N3 21.27(19) . . . . ? I2 S1 N1 N3 -124.87(17) . . . . ? N2 S1 N1 N3 123.3(2) 2 . . . ? N1 S1 N1 N3 -52.66(19) 2_545 . . . ? N4 S1 N1 N3 170.18(17) 2 . . . ? C13 S1 N1 I3 161.5(13) . . . 2_655 ? N2 S1 N1 I3 161.3(11) . . . 2_655 ? I1 S1 N1 I3 -119.4(9) . . . 2_655 ? I2 S1 N1 I3 94.4(9) . . . 2_655 ? N2 S1 N1 I3 -17.5(9) 2 . . 2_655 ? N1 S1 N1 I3 166.6(9) 2_545 . . 2_655 ? N4 S1 N1 I3 29.5(10) 2 . . 2_655 ? C13 S1 N1 I1 124.7(6) . . . 2 ? N2 S1 N1 I1 124.5(3) . . . 2 ? I1 S1 N1 I1 -156.22(8) . . . 2 ? I2 S1 N1 I1 57.64(10) . . . 2 ? N2 S1 N1 I1 -54.24(14) 2 . . 2 ? N1 S1 N1 I1 129.85(12) 2_545 . . 2 ? N4 S1 N1 I1 -7.31(19) 2 . . 2 ? S1 N1 N2 C13 -0.2(7) . . . . ? S1 N1 N2 C13 -11.1(10) 2 . . . ? N3 N1 N2 C13 114.2(8) . . . . ? I3 N1 N2 C13 -174.2(8) 2_655 . . . ? I1 N1 N2 C13 -71.0(8) 2 . . . ? C13 N1 N2 S1 0.2(7) . . . . ? S1 N1 N2 S1 -10.9(8) 2 . . . ? N3 N1 N2 S1 114.4(2) . . . . ? I3 N1 N2 S1 -174.0(4) 2_655 . . . ? I1 N1 N2 S1 -70.8(3) 2 . . . ? C13 N1 N2 N3 -114.2(8) . . . . ? S1 N1 N2 N3 -114.4(2) . . . . ? S1 N1 N2 N3 -125.3(9) 2 . . . ? I3 N1 N2 N3 71.6(3) 2_655 . . . ? I1 N1 N2 N3 174.7(3) 2 . . . ? C13 N1 N2 S1 -16.9(10) . . . 2_545 ? S1 N1 N2 S1 -17.1(8) . . . 2_545 ? S1 N1 N2 S1 -28.0(16) 2 . . 2_545 ? N3 N1 N2 S1 97.4(9) . . . 2_545 ? I3 N1 N2 S1 169.0(6) 2_655 . . 2_545 ? I1 N1 N2 S1 -87.9(9) 2 . . 2_545 ? C13 N1 N2 N4 -115.6(8) . . . . ? S1 N1 N2 N4 -115.8(3) . . . . ? S1 N1 N2 N4 -126.7(8) 2 . . . ? N3 N1 N2 N4 -1.4(3) . . . . ? I3 N1 N2 N4 70.2(4) 2_655 . . . ? I1 N1 N2 N4 173.4(2) 2 . . . ? C13 N1 N2 I2 56.6(7) . . . . ? S1 N1 N2 I2 56.36(14) . . . . ? S1 N1 N2 I2 45.5(9) 2 . . . ? N3 N1 N2 I2 170.8(2) . . . . ? I3 N1 N2 I2 -117.6(3) 2_655 . . . ? I1 N1 N2 I2 -14.5(3) 2 . . . ? C13 N1 N2 I4 177.8(8) . . . 4_575 ? S1 N1 N2 I4 177.56(19) . . . 4_575 ? S1 N1 N2 I4 166.7(8) 2 . . 4_575 ? N3 N1 N2 I4 -67.99(16) . . . 4_575 ? I3 N1 N2 I4 3.6(3) 2_655 . . 4_575 ? I1 N1 N2 I4 106.8(2) 2 . . 4_575 ? N1 S1 N2 C13 0.2(6) . . . . ? I1 S1 N2 C13 -101.7(6) . . . . ? I2 S1 N2 C13 109.0(7) . . . . ? N2 S1 N2 C13 2.1(6) 2 . . . ? N1 S1 N2 C13 -176.1(7) 2_545 . . . ? N4 S1 N2 C13 87.4(7) 2 . . . ? C13 S1 N2 N1 -0.2(6) . . . . ? I1 S1 N2 N1 -101.9(2) . . . . ? I2 S1 N2 N1 108.8(2) . . . . ? N2 S1 N2 N1 1.9(2) 2 . . . ? N1 S1 N2 N1 -176.30(16) 2_545 . . . ? N4 S1 N2 N1 87.2(3) 2 . . . ? C13 S1 N2 N3 64.9(6) . . . . ? N1 S1 N2 N3 65.1(3) . . . . ? I1 S1 N2 N3 -36.83(19) . . . . ? I2 S1 N2 N3 173.9(2) . . . . ? N2 S1 N2 N3 67.0(2) 2 . . . ? N1 S1 N2 N3 -111.2(2) 2_545 . . . ? N4 S1 N2 N3 152.3(2) 2 . . . ? C13 S1 N2 S1 173.3(7) . . . 2_545 ? N1 S1 N2 S1 173.5(3) . . . 2_545 ? I1 S1 N2 S1 71.63(13) . . . 2_545 ? I2 S1 N2 S1 -77.65(12) . . . 2_545 ? N2 S1 N2 S1 175.44(17) 2 . . 2_545 ? N1 S1 N2 S1 -2.76(16) 2_545 . . 2_545 ? N4 S1 N2 S1 -99.2(3) 2 . . 2_545 ? C13 S1 N2 N4 103.1(7) . . . . ? N1 S1 N2 N4 103.3(4) . . . . ? I1 S1 N2 N4 1.4(3) . . . . ? I2 S1 N2 N4 -147.9(3) . . . . ? N2 S1 N2 N4 105.2(3) 2 . . . ? N1 S1 N2 N4 -73.0(3) 2_545 . . . ? N4 S1 N2 N4 -169.5(3) 2 . . . ? C13 S1 N2 I2 -109.0(7) . . . . ? N1 S1 N2 I2 -108.8(2) . . . . ? I1 S1 N2 I2 149.27(7) . . . . ? N2 S1 N2 I2 -106.92(10) 2 . . . ? N1 S1 N2 I2 74.89(12) 2_545 . . . ? N4 S1 N2 I2 -21.6(3) 2 . . . ? C13 S1 N2 I4 -5.1(6) . . . 4_575 ? N1 S1 N2 I4 -4.9(4) . . . 4_575 ? I1 S1 N2 I4 -106.8(5) . . . 4_575 ? I2 S1 N2 I4 103.9(5) . . . 4_575 ? N2 S1 N2 I4 -3.0(5) 2 . . 4_575 ? N1 S1 N2 I4 178.8(5) 2_545 . . 4_575 ? N4 S1 N2 I4 82.3(5) 2 . . 4_575 ? C4 I2 N2 C13 139.1(5) . . . . ? C5 I2 N2 C13 117.8(5) . . . . ? C6 I2 N2 C13 168.6(5) 3_565 . . . ? S1 I2 N2 C13 -32.6(4) . . . . ? N4 I2 N2 C13 -17.9(5) 2 . . . ? C4 I2 N2 N1 113.0(4) . . . . ? C5 I2 N2 N1 91.7(3) . . . . ? C6 I2 N2 N1 142.4(3) 3_565 . . . ? S1 I2 N2 N1 -58.8(2) . . . . ? N4 I2 N2 N1 -44.1(3) 2 . . . ? C4 I2 N2 S1 171.7(3) . . . . ? C5 I2 N2 S1 150.45(18) . . . . ? C6 I2 N2 S1 -158.8(2) 3_565 . . . ? N4 I2 N2 S1 14.70(18) 2 . . . ? C4 I2 N2 N3 148.8(9) . . . . ? C5 I2 N2 N3 127.5(9) . . . . ? C6 I2 N2 N3 178.2(9) 3_565 . . . ? S1 I2 N2 N3 -23.0(9) . . . . ? N4 I2 N2 N3 -8.3(10) 2 . . . ? C4 I2 N2 S1 -88.8(3) . . . 2_545 ? C5 I2 N2 S1 -110.04(19) . . . 2_545 ? C6 I2 N2 S1 -59.3(3) 3_565 . . 2_545 ? S1 I2 N2 S1 99.50(17) . . . 2_545 ? N4 I2 N2 S1 114.20(14) 2 . . 2_545 ? C4 I2 N2 N4 -82.4(6) . . . . ? C5 I2 N2 N4 -103.7(5) . . . . ? C6 I2 N2 N4 -53.0(6) 3_565 . . . ? S1 I2 N2 N4 105.8(6) . . . . ? N4 I2 N2 N4 120.5(5) 2 . . . ? C4 I2 N2 I4 26.1(4) . . . 4_575 ? C5 I2 N2 I4 4.8(3) . . . 4_575 ? C6 I2 N2 I4 55.5(4) 3_565 . . 4_575 ? S1 I2 N2 I4 -145.7(3) . . . 4_575 ? N4 I2 N2 I4 -130.98(19) 2 . . 4_575 ? N4 S2 N3 C14 1.5(6) . . . . ? I4 S2 N3 C14 96.4(6) 4_575 . . . ? I3 S2 N3 C14 -108.7(6) . . . . ? N3 S2 N3 C14 -9.8(6) 2_645 . . . ? N4 S2 N3 C14 -179.6(6) 2_655 . . . ? C14 S2 N3 N4 -1.5(6) . . . . ? I4 S2 N3 N4 94.9(2) 4_575 . . . ? I3 S2 N3 N4 -110.3(2) . . . . ? N3 S2 N3 N4 -11.3(2) 2_645 . . . ? N4 S2 N3 N4 178.89(16) 2_655 . . . ? C14 S2 N3 N2 -61.6(6) . . . . ? N4 S2 N3 N2 -60.1(3) . . . . ? I4 S2 N3 N2 34.8(2) 4_575 . . . ? I3 S2 N3 N2 -170.4(2) . . . . ? N3 S2 N3 N2 -71.4(2) 2_645 . . . ? N4 S2 N3 N2 118.8(2) 2_655 . . . ? C14 S2 N3 S2 -175.7(7) . . . 2_655 ? N4 S2 N3 S2 -174.2(3) . . . 2_655 ? I4 S2 N3 S2 -79.32(12) 4_575 . . 2_655 ? I3 S2 N3 S2 75.53(12) . . . 2_655 ? N3 S2 N3 S2 174.49(17) 2_645 . . 2_655 ? N4 S2 N3 S2 4.68(16) 2_655 . . 2_655 ? C14 S2 N3 N1 -100.4(7) . . . . ? N4 S2 N3 N1 -98.9(4) . . . . ? I4 S2 N3 N1 -4.0(3) 4_575 . . . ? I3 S2 N3 N1 150.8(3) . . . . ? N3 S2 N3 N1 -110.2(3) 2_645 . . . ? N4 S2 N3 N1 80.0(3) 2_655 . . . ? C14 S2 N3 I3 108.7(6) . . . . ? N4 S2 N3 I3 110.3(2) . . . . ? I4 S2 N3 I3 -154.86(7) 4_575 . . . ? N3 S2 N3 I3 98.96(11) 2_645 . . . ? N4 S2 N3 I3 -70.85(12) 2_655 . . . ? C14 S2 N3 I1 16.5(5) . . . . ? N4 S2 N3 I1 18.0(3) . . . . ? I4 S2 N3 I1 112.9(4) 4_575 . . . ? I3 S2 N3 I1 -92.2(4) . . . . ? N3 S2 N3 I1 6.7(4) 2_645 . . . ? N4 S2 N3 I1 -163.1(4) 2_655 . . . ? C14 S2 N3 I4 -96.4(6) . . . 4_575 ? N4 S2 N3 I4 -94.9(2) . . . 4_575 ? I3 S2 N3 I4 154.86(7) . . . 4_575 ? N3 S2 N3 I4 -106.18(10) 2_645 . . 4_575 ? N4 S2 N3 I4 84.01(12) 2_655 . . 4_575 ? C13 N2 N3 C14 179.2(7) . . . . ? N1 N2 N3 C14 -152.9(5) . . . . ? S1 N2 N3 C14 149.1(5) . . . . ? S1 N2 N3 C14 50.3(5) 2_545 . . . ? N4 N2 N3 C14 25.1(4) . . . . ? I2 N2 N3 C14 169.8(9) . . . . ? I4 N2 N3 C14 -61.2(4) 4_575 . . . ? C13 N2 N3 N4 154.1(6) . . . . ? N1 N2 N3 N4 -178.0(4) . . . . ? S1 N2 N3 N4 124.0(3) . . . . ? S1 N2 N3 N4 25.3(3) 2_545 . . . ? I2 N2 N3 N4 144.8(10) . . . . ? I4 N2 N3 N4 -86.2(3) 4_575 . . . ? C13 N2 N3 S2 -150.9(5) . . . . ? N1 N2 N3 S2 -123.0(3) . . . . ? S1 N2 N3 S2 179.0(2) . . . . ? S1 N2 N3 S2 80.3(3) 2_545 . . . ? N4 N2 N3 S2 55.0(3) . . . . ? I2 N2 N3 S2 -160.3(9) . . . . ? I4 N2 N3 S2 -31.26(18) 4_575 . . . ? C13 N2 N3 S2 -50.1(5) . . . 2_655 ? N1 N2 N3 S2 -22.3(3) . . . 2_655 ? S1 N2 N3 S2 -80.2(3) . . . 2_655 ? S1 N2 N3 S2 -178.98(19) 2_545 . . 2_655 ? N4 N2 N3 S2 155.7(4) . . . 2_655 ? I2 N2 N3 S2 -59.5(10) . . . 2_655 ? I4 N2 N3 S2 69.51(18) 4_575 . . 2_655 ? C13 N2 N3 N1 -27.9(4) . . . . ? S1 N2 N3 N1 -58.0(2) . . . . ? S1 N2 N3 N1 -156.7(4) 2_545 . . . ? N4 N2 N3 N1 178.0(4) . . . . ? I2 N2 N3 N1 -37.2(9) . . . . ? I4 N2 N3 N1 91.8(3) 4_575 . . . ? C13 N2 N3 I3 179.4(8) . . . . ? N1 N2 N3 I3 -152.7(8) . . . . ? S1 N2 N3 I3 149.3(8) . . . . ? S1 N2 N3 I3 50.6(9) 2_545 . . . ? N4 N2 N3 I3 25.3(8) . . . . ? I2 N2 N3 I3 170.0(6) . . . . ? I4 N2 N3 I3 -61.0(8) 4_575 . . . ? C13 N2 N3 I1 63.8(5) . . . . ? N1 N2 N3 I1 91.7(3) . . . . ? S1 N2 N3 I1 33.71(18) . . . . ? S1 N2 N3 I1 -65.04(17) 2_545 . . . ? N4 N2 N3 I1 -90.3(3) . . . . ? I2 N2 N3 I1 54.4(9) . . . . ? I4 N2 N3 I1 -176.55(15) 4_575 . . . ? C13 N2 N3 I4 -119.7(5) . . . 4_575 ? N1 N2 N3 I4 -91.8(3) . . . 4_575 ? S1 N2 N3 I4 -149.7(2) . . . 4_575 ? S1 N2 N3 I4 111.51(19) 2_545 . . 4_575 ? N4 N2 N3 I4 86.2(3) . . . 4_575 ? I2 N2 N3 I4 -129.0(10) . . . 4_575 ? C13 N1 N3 C14 60.6(7) . . . . ? N2 N1 N3 C14 32.7(6) . . . . ? S1 N1 N3 C14 89.4(6) . . . . ? S1 N1 N3 C14 -169.0(6) 2 . . . ? I3 N1 N3 C14 -99.9(6) 2_655 . . . ? I1 N1 N3 C14 -110.0(17) 2 . . . ? C13 N1 N3 N4 29.9(5) . . . . ? N2 N1 N3 N4 2.0(4) . . . . ? S1 N1 N3 N4 58.7(4) . . . . ? S1 N1 N3 N4 160.4(3) 2 . . . ? I3 N1 N3 N4 -130.5(3) 2_655 . . . ? I1 N1 N3 N4 -140.6(16) 2 . . . ? C13 N1 N3 S2 102.1(5) . . . . ? N2 N1 N3 S2 74.2(4) . . . . ? S1 N1 N3 S2 130.9(3) . . . . ? S1 N1 N3 S2 -127.5(3) 2 . . . ? I3 N1 N3 S2 -58.4(3) 2_655 . . . ? I1 N1 N3 S2 -68.4(18) 2 . . . ? C13 N1 N3 N2 27.9(4) . . . . ? S1 N1 N3 N2 56.7(2) . . . . ? S1 N1 N3 N2 158.3(4) 2 . . . ? I3 N1 N3 N2 -132.6(3) 2_655 . . . ? I1 N1 N3 N2 -142.7(18) 2 . . . ? C13 N1 N3 S2 -173.4(5) . . . 2_655 ? N2 N1 N3 S2 158.8(3) . . . 2_655 ? S1 N1 N3 S2 -144.6(2) . . . 2_655 ? S1 N1 N3 S2 -42.9(3) 2 . . 2_655 ? I3 N1 N3 S2 26.17(12) 2_655 . . 2_655 ? I1 N1 N3 S2 16.1(17) 2 . . 2_655 ? C13 N1 N3 I3 -170.6(6) . . . . ? N2 N1 N3 I3 161.5(6) . . . . ? S1 N1 N3 I3 -141.8(5) . . . . ? S1 N1 N3 I3 -40.2(7) 2 . . . ? I3 N1 N3 I3 28.9(6) 2_655 . . . ? I1 N1 N3 I3 19(2) 2 . . . ? C13 N1 N3 I1 -47.7(4) . . . . ? N2 N1 N3 I1 -75.6(3) . . . . ? S1 N1 N3 I1 -18.91(17) . . . . ? S1 N1 N3 I1 82.7(2) 2 . . . ? I3 N1 N3 I1 151.82(14) 2_655 . . . ? I1 N1 N3 I1 141.7(17) 2 . . . ? C13 N1 N3 I4 98.7(4) . . . 4_575 ? N2 N1 N3 I4 70.8(2) . . . 4_575 ? S1 N1 N3 I4 127.46(19) . . . 4_575 ? S1 N1 N3 I4 -130.9(2) 2 . . 4_575 ? I3 N1 N3 I4 -61.81(11) 2_655 . . 4_575 ? I1 N1 N3 I4 -71.9(17) 2 . . 4_575 ? C7 I3 N3 C14 -146.7(5) . . . . ? C8 I3 N3 C14 179.2(4) . . . . ? C12 I3 N3 C14 -123.6(5) . . . . ? S2 I3 N3 C14 33.9(4) . . . . ? N4 I3 N3 C14 99.7(5) 2_655 . . . ? N1 I3 N3 C14 19.6(5) 2_645 . . . ? C7 I3 N3 N4 -122.9(4) . . . . ? C8 I3 N3 N4 -157.0(3) . . . . ? C12 I3 N3 N4 -99.8(3) . . . . ? S2 I3 N3 N4 57.7(2) . . . . ? N4 I3 N3 N4 123.5(3) 2_655 . . . ? N1 I3 N3 N4 43.4(3) 2_645 . . . ? C7 I3 N3 S2 179.4(3) . . . . ? C8 I3 N3 S2 145.3(3) . . . . ? C12 I3 N3 S2 -157.51(18) . . . . ? N4 I3 N3 S2 65.78(15) 2_655 . . . ? N1 I3 N3 S2 -14.28(19) 2_645 . . . ? C7 I3 N3 N2 -147.0(8) . . . . ? C8 I3 N3 N2 179.0(8) . . . . ? C12 I3 N3 N2 -123.8(8) . . . . ? S2 I3 N3 N2 33.7(8) . . . . ? N4 I3 N3 N2 99.5(9) 2_655 . . . ? N1 I3 N3 N2 19.4(9) 2_645 . . . ? C7 I3 N3 S2 78.9(4) . . . 2_655 ? C8 I3 N3 S2 44.8(3) . . . 2_655 ? C12 I3 N3 S2 102.0(2) . . . 2_655 ? S2 I3 N3 S2 -100.44(17) . . . 2_655 ? N4 I3 N3 S2 -34.66(13) 2_655 . . 2_655 ? N1 I3 N3 S2 -114.72(14) 2_645 . . 2_655 ? C7 I3 N3 N1 76.2(7) . . . . ? C8 I3 N3 N1 42.1(7) . . . . ? C12 I3 N3 N1 99.4(6) . . . . ? S2 I3 N3 N1 -103.1(6) . . . . ? N4 I3 N3 N1 -37.4(6) 2_655 . . . ? N1 I3 N3 N1 -117.4(5) 2_645 . . . ? C7 I3 N3 I1 -38.3(4) . . . . ? C8 I3 N3 I1 -72.4(3) . . . . ? C12 I3 N3 I1 -15.2(3) . . . . ? S2 I3 N3 I1 142.4(3) . . . . ? N4 I3 N3 I1 -151.9(2) 2_655 . . . ? N1 I3 N3 I1 128.08(17) 2_645 . . . ? C7 I3 N3 I4 158.2(3) . . . 4_575 ? C8 I3 N3 I4 124.1(3) . . . 4_575 ? C12 I3 N3 I4 -178.70(18) . . . 4_575 ? S2 I3 N3 I4 -21.19(7) . . . 4_575 ? N4 I3 N3 I4 44.59(15) 2_655 . . 4_575 ? N1 I3 N3 I4 -35.5(2) 2_645 . . 4_575 ? C1 I1 N3 C14 74.8(5) . . . . ? C2 I1 N3 C14 87.6(5) . . . . ? C3 I1 N3 C14 62.0(5) 3_666 . . . ? S1 I1 N3 C14 -104.9(5) . . . . ? N1 I1 N3 C14 -56.3(5) 2_545 . . . ? C1 I1 N3 N4 80.9(3) . . . . ? C2 I1 N3 N4 93.8(3) . . . . ? C3 I1 N3 N4 68.2(3) 3_666 . . . ? S1 I1 N3 N4 -98.8(2) . . . . ? N1 I1 N3 N4 -50.1(3) 2_545 . . . ? C1 I1 N3 S2 64.7(5) . . . . ? C2 I1 N3 S2 77.5(5) . . . . ? C3 I1 N3 S2 51.9(4) 3_666 . . . ? S1 I1 N3 S2 -115.0(4) . . . . ? N1 I1 N3 S2 -66.4(4) 2_545 . . . ? C1 I1 N3 N2 154.3(3) . . . . ? C2 I1 N3 N2 167.1(2) . . . . ? C3 I1 N3 N2 141.5(2) 3_666 . . . ? S1 I1 N3 N2 -25.41(14) . . . . ? N1 I1 N3 N2 23.19(19) 2_545 . . . ? C1 I1 N3 S2 -101.3(3) . . . 2_655 ? C2 I1 N3 S2 -88.5(2) . . . 2_655 ? C3 I1 N3 S2 -114.1(2) 3_666 . . 2_655 ? S1 I1 N3 S2 78.97(19) . . . 2_655 ? N1 I1 N3 S2 127.57(19) 2_545 . . 2_655 ? C1 I1 N3 N1 -165.6(2) . . . . ? C2 I1 N3 N1 -152.76(19) . . . . ? C3 I1 N3 N1 -178.4(2) 3_666 . . . ? S1 I1 N3 N1 14.73(13) . . . . ? N1 I1 N3 N1 63.33(10) 2_545 . . . ? C1 I1 N3 I3 -8.7(3) . . . . ? C2 I1 N3 I3 4.1(3) . . . . ? C3 I1 N3 I3 -21.5(2) 3_666 . . . ? S1 I1 N3 I3 171.60(17) . . . . ? N1 I1 N3 I3 -139.80(17) 2_545 . . . ? C1 I1 N3 I4 150.2(3) . . . 4_575 ? C2 I1 N3 I4 163.0(2) . . . 4_575 ? C3 I1 N3 I4 137.4(3) 3_666 . . 4_575 ? S1 I1 N3 I4 -29.5(2) . . . 4_575 ? N1 I1 N3 I4 19.1(3) 2_545 . . 4_575 ? S2 N3 N4 C14 1.8(7) . . . . ? N2 N3 N4 C14 121.3(8) . . . . ? S2 N3 N4 C14 16.6(10) 2_655 . . . ? N1 N3 N4 C14 120.0(8) . . . . ? I3 N3 N4 C14 -51.6(7) . . . . ? I1 N3 N4 C14 -168.5(8) . . . . ? I4 N3 N4 C14 56.8(7) 4_575 . . . ? C14 N3 N4 S2 -1.8(7) . . . . ? N2 N3 N4 S2 119.5(2) . . . . ? S2 N3 N4 S2 14.8(8) 2_655 . . . ? N1 N3 N4 S2 118.2(3) . . . . ? I3 N3 N4 S2 -53.37(13) . . . . ? I1 N3 N4 S2 -170.25(19) . . . . ? I4 N3 N4 S2 55.05(11) 4_575 . . . ? C14 N3 N4 F2 119.4(8) . . . 3_666 ? S2 N3 N4 F2 121.2(2) . . . 3_666 ? N2 N3 N4 F2 -119.3(2) . . . 3_666 ? S2 N3 N4 F2 136.0(8) 2_655 . . 3_666 ? N1 N3 N4 F2 -120.6(3) . . . 3_666 ? I3 N3 N4 F2 67.79(19) . . . 3_666 ? I1 N3 N4 F2 -49.10(16) . . . 3_666 ? I4 N3 N4 F2 176.2(2) 4_575 . . 3_666 ? C14 N3 N4 N2 -121.3(8) . . . . ? S2 N3 N4 N2 -119.5(2) . . . . ? S2 N3 N4 N2 -104.7(8) 2_655 . . . ? N1 N3 N4 N2 -1.3(3) . . . . ? I3 N3 N4 N2 -172.9(2) . . . . ? I1 N3 N4 N2 70.21(16) . . . . ? I4 N3 N4 N2 -64.50(15) 4_575 . . . ? C14 N3 N4 S2 27.9(10) . . . 2_645 ? S2 N3 N4 S2 29.6(7) . . . 2_645 ? N2 N3 N4 S2 149.2(8) . . . 2_645 ? S2 N3 N4 S2 44.5(14) 2_655 . . 2_645 ? N1 N3 N4 S2 147.9(6) . . . 2_645 ? I3 N3 N4 S2 -23.7(8) . . . 2_645 ? I1 N3 N4 S2 -140.6(7) . . . 2_645 ? I4 N3 N4 S2 84.7(7) 4_575 . . 2_645 ? C14 N3 N4 I3 -61.6(8) . . . 2_645 ? S2 N3 N4 I3 -59.8(4) . . . 2_645 ? N2 N3 N4 I3 59.7(4) . . . 2_645 ? S2 N3 N4 I3 -45.0(11) 2_655 . . 2_645 ? N1 N3 N4 I3 58.4(5) . . . 2_645 ? I3 N3 N4 I3 -113.2(3) . . . 2_645 ? I1 N3 N4 I3 129.9(3) . . . 2_645 ? I4 N3 N4 I3 -4.8(4) 4_575 . . 2_645 ? C14 N3 N4 S1 -144.7(8) . . . 2_545 ? S2 N3 N4 S1 -143.0(3) . . . 2_545 ? N2 N3 N4 S1 -23.4(3) . . . 2_545 ? S2 N3 N4 S1 -128.1(7) 2_655 . . 2_545 ? N1 N3 N4 S1 -24.8(4) . . . 2_545 ? I3 N3 N4 S1 163.7(2) . . . 2_545 ? I1 N3 N4 S1 46.8(3) . . . 2_545 ? I4 N3 N4 S1 -87.9(2) 4_575 . . 2_545 ? C14 N3 N4 I2 155.4(8) . . . 2_545 ? S2 N3 N4 I2 157.2(4) . . . 2_545 ? N2 N3 N4 I2 -83.3(3) . . . 2_545 ? S2 N3 N4 I2 172.0(6) 2_655 . . 2_545 ? N1 N3 N4 I2 -84.6(4) . . . 2_545 ? I3 N3 N4 I2 103.8(3) . . . 2_545 ? I1 N3 N4 I2 -13.1(3) . . . 2_545 ? I4 N3 N4 I2 -147.8(3) 4_575 . . 2_545 ? N3 S2 N4 C14 -1.5(6) . . . . ? I4 S2 N4 C14 -85.0(6) 4_575 . . . ? I3 S2 N4 C14 66.0(6) . . . . ? N3 S2 N4 C14 170.9(6) 2_645 . . . ? N4 S2 N4 C14 -3.2(6) 2_655 . . . ? C14 S2 N4 N3 1.5(6) . . . . ? I4 S2 N4 N3 -83.4(2) 4_575 . . . ? I3 S2 N4 N3 67.5(2) . . . . ? N3 S2 N4 N3 172.42(15) 2_645 . . . ? N4 S2 N4 N3 -1.6(2) 2_655 . . . ? C14 S2 N4 F2 -65.1(6) . . . 3_666 ? N3 S2 N4 F2 -66.6(3) . . . 3_666 ? I4 S2 N4 F2 -150.1(2) 4_575 . . 3_666 ? I3 S2 N4 F2 0.9(3) . . . 3_666 ? N3 S2 N4 F2 105.8(3) 2_645 . . 3_666 ? N4 S2 N4 F2 -68.3(3) 2_655 . . 3_666 ? C14 S2 N4 N2 58.5(6) . . . . ? N3 S2 N4 N2 56.9(3) . . . . ? I4 S2 N4 N2 -26.5(2) 4_575 . . . ? I3 S2 N4 N2 124.46(19) . . . . ? N3 S2 N4 N2 -130.6(2) 2_645 . . . ? N4 S2 N4 N2 55.3(2) 2_655 . . . ? C14 S2 N4 S2 -166.2(7) . . . 2_645 ? N3 S2 N4 S2 -167.7(3) . . . 2_645 ? I4 S2 N4 S2 108.84(12) 4_575 . . 2_645 ? I3 S2 N4 S2 -100.19(13) . . . 2_645 ? N3 S2 N4 S2 4.70(16) 2_645 . . 2_645 ? N4 S2 N4 S2 -169.35(17) 2_655 . . 2_645 ? C14 S2 N4 I3 141.8(6) . . . 2_645 ? N3 S2 N4 I3 140.2(3) . . . 2_645 ? I4 S2 N4 I3 56.77(10) 4_575 . . 2_645 ? I3 S2 N4 I3 -152.26(9) . . . 2_645 ? N3 S2 N4 I3 -47.37(15) 2_645 . . 2_645 ? N4 S2 N4 I3 138.59(12) 2_655 . . 2_645 ? C14 S2 N4 S1 104.8(8) . . . 2_545 ? N3 S2 N4 S1 103.2(5) . . . 2_545 ? I4 S2 N4 S1 19.8(4) 4_575 . . 2_545 ? I3 S2 N4 S1 170.8(4) . . . 2_545 ? N3 S2 N4 S1 -84.4(4) 2_645 . . 2_545 ? N4 S2 N4 S1 101.6(4) 2_655 . . 2_545 ? C14 S2 N4 I2 -130.6(9) . . . 2_545 ? N3 S2 N4 I2 -132.1(7) . . . 2_545 ? I4 S2 N4 I2 144.4(6) 4_575 . . 2_545 ? I3 S2 N4 I2 -64.6(6) . . . 2_545 ? N3 S2 N4 I2 40.3(6) 2_645 . . 2_545 ? N4 S2 N4 I2 -133.8(6) 2_655 . . 2_545 ? C13 N2 N4 C14 -56.9(8) . . . . ? N1 N2 N4 C14 -23.3(6) . . . . ? S1 N2 N4 C14 -97.2(5) . . . . ? N3 N2 N4 C14 -25.4(4) . . . . ? S1 N2 N4 C14 -179.8(5) 2_545 . . . ? I2 N2 N4 C14 173.6(6) . . . . ? I4 N2 N4 C14 52.8(4) 4_575 . . . ? C13 N2 N4 N3 -31.5(7) . . . . ? N1 N2 N4 N3 2.1(4) . . . . ? S1 N2 N4 N3 -71.8(4) . . . . ? S1 N2 N4 N3 -154.4(3) 2_545 . . . ? I2 N2 N4 N3 -161.0(5) . . . . ? I4 N2 N4 N3 78.2(3) 4_575 . . . ? C13 N2 N4 S2 -86.2(7) . . . . ? N1 N2 N4 S2 -52.6(4) . . . . ? S1 N2 N4 S2 -126.5(3) . . . . ? N3 N2 N4 S2 -54.7(3) . . . . ? S1 N2 N4 S2 150.9(2) 2_545 . . . ? I2 N2 N4 S2 144.3(4) . . . . ? I4 N2 N4 S2 23.54(18) 4_575 . . . ? C13 N2 N4 F2 37.5(7) . . . 3_666 ? N1 N2 N4 F2 71.2(4) . . . 3_666 ? S1 N2 N4 F2 -2.7(4) . . . 3_666 ? N3 N2 N4 F2 69.0(3) . . . 3_666 ? S1 N2 N4 F2 -85.4(2) 2_545 . . 3_666 ? I2 N2 N4 F2 -92.0(5) . . . 3_666 ? I4 N2 N4 F2 147.3(2) 4_575 . . 3_666 ? C13 N2 N4 S2 165.8(6) . . . 2_645 ? N1 N2 N4 S2 -160.5(3) . . . 2_645 ? S1 N2 N4 S2 125.6(3) . . . 2_645 ? N3 N2 N4 S2 -162.6(5) . . . 2_645 ? S1 N2 N4 S2 43.0(3) 2_545 . . 2_645 ? I2 N2 N4 S2 36.4(7) . . . 2_645 ? I4 N2 N4 S2 -84.4(3) 4_575 . . 2_645 ? C13 N2 N4 I3 -171.7(6) . . . 2_645 ? N1 N2 N4 I3 -138.0(3) . . . 2_645 ? S1 N2 N4 I3 148.1(3) . . . 2_645 ? N3 N2 N4 I3 -140.1(3) . . . 2_645 ? S1 N2 N4 I3 65.48(12) 2_545 . . 2_645 ? I2 N2 N4 I3 58.9(5) . . . 2_645 ? I4 N2 N4 I3 -61.89(10) 4_575 . . 2_645 ? C13 N2 N4 S1 122.9(7) . . . 2_545 ? N1 N2 N4 S1 156.5(4) . . . 2_545 ? S1 N2 N4 S1 82.6(3) . . . 2_545 ? N3 N2 N4 S1 154.4(3) . . . 2_545 ? I2 N2 N4 S1 -6.6(5) . . . 2_545 ? I4 N2 N4 S1 -127.37(15) 4_575 . . 2_545 ? C13 N2 N4 I2 97.5(6) . . . 2_545 ? N1 N2 N4 I2 131.1(3) . . . 2_545 ? S1 N2 N4 I2 57.2(3) . . . 2_545 ? N3 N2 N4 I2 129.0(3) . . . 2_545 ? S1 N2 N4 I2 -25.38(13) 2_545 . . 2_545 ? I2 N2 N4 I2 -32.0(6) . . . 2_545 ? I4 N2 N4 I2 -152.75(16) 4_575 . . 2_545 ? C2 I1 C1 C3 176.2(11) . . . 3_666 ? S1 I1 C1 C3 -29(4) . . . 3_666 ? N3 I1 C1 C3 -34.5(6) . . . 3_666 ? N1 I1 C1 C3 80.7(7) 2_545 . . 3_666 ? C3 I1 C1 C2 -176.2(11) 3_666 . . . ? S1 I1 C1 C2 155(3) . . . . ? N3 I1 C1 C2 149.3(6) . . . . ? N1 I1 C1 C2 -95.5(6) 2_545 . . . ? C3 C1 C2 F1 178.6(7) 3_666 . . . ? I1 C1 C2 F1 -5.0(10) . . . . ? C3 C1 C2 C3 -0.4(12) 3_666 . . . ? I1 C1 C2 C3 176.0(6) . . . . ? C3 C1 C2 I1 -176.4(10) 3_666 . . . ? C1 I1 C2 F1 175.7(8) . . . . ? C3 I1 C2 F1 177.7(5) 3_666 . . . ? S1 I1 C2 F1 -0.4(7) . . . . ? N3 I1 C2 F1 141.8(3) . . . . ? N1 I1 C2 F1 -82.3(4) 2_545 . . . ? C1 I1 C2 C3 -9.0(12) . . . . ? C3 I1 C2 C3 -7.0(14) 3_666 . . . ? S1 I1 C2 C3 174.9(11) . . . . ? N3 I1 C2 C3 -42.9(14) . . . . ? N1 I1 C2 C3 93.1(14) 2_545 . . . ? C3 I1 C2 C1 2.0(6) 3_666 . . . ? S1 I1 C2 C1 -176.1(5) . . . . ? N3 I1 C2 C1 -33.9(6) . . . . ? N1 I1 C2 C1 102.0(6) 2_545 . . . ? N4 F2 C3 C1 8.1(18) 3_666 . . 3_666 ? N4 F2 C3 C2 -173.1(10) 3_666 . . . ? N4 F2 C3 I1 5.0(14) 3_666 . . 3_666 ? F1 C2 C3 F2 2.5(11) . . . . ? C1 C2 C3 F2 -178.4(7) . . . . ? I1 C2 C3 F2 -172.2(10) . . . . ? F1 C2 C3 C1 -178.6(7) . . . 3_666 ? C1 C2 C3 C1 0.4(13) . . . 3_666 ? I1 C2 C3 C1 6.7(19) . . . 3_666 ? F1 C2 C3 I1 -172.6(10) . . . 3_666 ? C1 C2 C3 I1 6.5(18) . . . 3_666 ? I1 C2 C3 I1 13(3) . . . 3_666 ? C5 I2 C4 C6 179.2(11) . . . 3_565 ? S1 I2 C4 C6 161.5(9) . . . 3_565 ? N2 I2 C4 C6 122.5(6) . . . 3_565 ? N4 I2 C4 C6 -83.1(6) 2 . . 3_565 ? C6 I2 C4 C5 -179.2(11) 3_565 . . . ? S1 I2 C4 C5 -17.7(18) . . . . ? N2 I2 C4 C5 -56.7(7) . . . . ? N4 I2 C4 C5 97.7(6) 2 . . . ? C6 C4 C5 F3 179.3(6) 3_565 . . . ? I2 C4 C5 F3 -1.5(9) . . . . ? C6 C4 C5 C6 -0.9(12) 3_565 . . . ? I2 C4 C5 C6 178.4(6) . . . . ? C6 C4 C5 I2 -179.2(11) 3_565 . . . ? C4 I2 C5 F3 178.7(8) . . . . ? C6 I2 C5 F3 179.1(5) 3_565 . . . ? S1 I2 C5 F3 -6.5(5) . . . . ? N2 I2 C5 F3 -46.3(4) . . . . ? N4 I2 C5 F3 82.8(4) 2 . . . ? C4 I2 C5 C6 -3.7(13) . . . . ? C6 I2 C5 C6 -3.3(15) 3_565 . . . ? S1 I2 C5 C6 171.1(13) . . . . ? N2 I2 C5 C6 131.3(14) . . . . ? N4 I2 C5 C6 -99.6(14) 2 . . . ? C6 I2 C5 C4 0.4(6) 3_565 . . . ? S1 I2 C5 C4 174.8(5) . . . . ? N2 I2 C5 C4 135.0(6) . . . . ? N4 I2 C5 C4 -95.9(6) 2 . . . ? F3 C5 C6 F4 -0.4(10) . . . . ? C4 C5 C6 F4 179.7(7) . . . . ? I2 C5 C6 F4 -177.7(10) . . . . ? F3 C5 C6 C4 -179.3(6) . . . 3_565 ? C4 C5 C6 C4 0.9(13) . . . 3_565 ? I2 C5 C6 C4 3.5(19) . . . 3_565 ? F3 C5 C6 I2 -177.0(9) . . . 3_565 ? C4 C5 C6 I2 3.1(18) . . . 3_565 ? I2 C5 C6 I2 6(3) . . . 3_565 ? C8 I3 C7 C12 -179.8(10) . . . . ? S2 I3 C7 C12 93(17) . . . . ? N3 I3 C7 C12 60.2(7) . . . . ? N4 I3 C7 C12 149.6(5) 2_655 . . . ? N1 I3 C7 C12 -106.8(6) 2_645 . . . ? C12 I3 C7 C8 179.8(10) . . . . ? S2 I3 C7 C8 -87(17) . . . . ? N3 I3 C7 C8 -120.0(6) . . . . ? N4 I3 C7 C8 -30.5(7) 2_655 . . . ? N1 I3 C7 C8 73.0(6) 2_645 . . . ? C12 C7 C8 F5 -178.0(7) . . . . ? I3 C7 C8 F5 2.2(10) . . . . ? C12 C7 C8 C9 1.8(11) . . . . ? I3 C7 C8 C9 -178.1(5) . . . . ? C12 C7 C8 I3 179.8(10) . . . . ? C7 I3 C8 F5 -178.1(8) . . . . ? C12 I3 C8 F5 -178.2(5) . . . . ? S2 I3 C8 F5 -0.2(7) . . . . ? N3 I3 C8 F5 -92.0(5) . . . . ? N4 I3 C8 F5 -24.1(4) 2_655 . . . ? N1 I3 C8 F5 69.2(4) 2_645 . . . ? C7 I3 C8 C9 4.2(12) . . . . ? C12 I3 C8 C9 4.1(13) . . . . ? S2 I3 C8 C9 -177.9(11) . . . . ? N3 I3 C8 C9 90.4(13) . . . . ? N4 I3 C8 C9 158.2(13) 2_655 . . . ? N1 I3 C8 C9 -108.5(13) 2_645 . . . ? C12 I3 C8 C7 -0.1(6) . . . . ? S2 I3 C8 C7 177.9(5) . . . . ? N3 I3 C8 C7 86.2(6) . . . . ? N4 I3 C8 C7 154.0(6) 2_655 . . . ? N1 I3 C8 C7 -112.7(6) 2_645 . . . ? F5 C8 C9 F6 -0.3(10) . . . . ? C7 C8 C9 F6 180.0(7) . . . . ? I3 C8 C9 F6 177.1(10) . . . . ? F5 C8 C9 C10 178.8(7) . . . . ? C7 C8 C9 C10 -1.0(11) . . . . ? I3 C8 C9 C10 -3.9(18) . . . . ? F5 C8 C9 I4 -173.4(11) . . . . ? C7 C8 C9 I4 6.9(19) . . . . ? I3 C8 C9 I4 4(3) . . . . ? C10 I4 C9 F6 174.9(8) . . . . ? C11 I4 C9 F6 176.9(5) . . . . ? S2 I4 C9 F6 -4.5(7) 4_676 . . . ? N2 I4 C9 F6 135.5(4) 4_676 . . . ? N3 I4 C9 F6 158.4(4) 4_676 . . . ? C10 I4 C9 C8 -11.2(13) . . . . ? C11 I4 C9 C8 -9.2(14) . . . . ? S2 I4 C9 C8 169.4(12) 4_676 . . . ? N2 I4 C9 C8 -50.5(15) 4_676 . . . ? N3 I4 C9 C8 -27.7(18) 4_676 . . . ? C11 I4 C9 C10 2.0(6) . . . . ? S2 I4 C9 C10 -179.4(5) 4_676 . . . ? N2 I4 C9 C10 -39.3(6) 4_676 . . . ? N3 I4 C9 C10 -16.5(9) 4_676 . . . ? F6 C9 C10 C11 177.7(6) . . . . ? C8 C9 C10 C11 -1.3(11) . . . . ? I4 C9 C10 C11 -176.4(10) . . . . ? F6 C9 C10 I4 -5.8(9) . . . . ? C8 C9 C10 I4 175.2(6) . . . . ? C9 I4 C10 C11 176.2(11) . . . . ? S2 I4 C10 C11 -148(31) 4_676 . . . ? N2 I4 C10 C11 -39.3(6) 4_676 . . . ? N3 I4 C10 C11 -11.4(8) 4_676 . . . ? C11 I4 C10 C9 -176.2(11) . . . . ? S2 I4 C10 C9 35(32) 4_676 . . . ? N2 I4 C10 C9 144.5(6) 4_676 . . . ? N3 I4 C10 C9 172.4(4) 4_676 . . . ? C9 C10 C11 F7 -179.1(7) . . . . ? I4 C10 C11 F7 4.5(10) . . . . ? C9 C10 C11 C12 2.7(11) . . . . ? I4 C10 C11 C12 -173.6(5) . . . . ? C9 C10 C11 I4 176.4(10) . . . . ? C10 I4 C11 F7 -176.1(8) . . . . ? C9 I4 C11 F7 -178.2(5) . . . . ? S2 I4 C11 F7 3.3(7) 4_676 . . . ? N2 I4 C11 F7 -36.1(4) 4_676 . . . ? N3 I4 C11 F7 -4.4(4) 4_676 . . . ? C9 I4 C11 C10 -2.1(6) . . . . ? S2 I4 C11 C10 179.4(5) 4_676 . . . ? N2 I4 C11 C10 140.0(6) 4_676 . . . ? N3 I4 C11 C10 171.7(6) 4_676 . . . ? C10 I4 C11 C12 13.4(11) . . . . ? C9 I4 C11 C12 11.3(12) . . . . ? S2 I4 C11 C12 -167.2(10) 4_676 . . . ? N2 I4 C11 C12 153.3(13) 4_676 . . . ? N3 I4 C11 C12 -174.9(12) 4_676 . . . ? F7 C11 C12 F8 0.0(10) . . . . ? C10 C11 C12 F8 178.2(7) . . . . ? I4 C11 C12 F8 169.2(9) . . . . ? F7 C11 C12 C7 179.8(7) . . . . ? C10 C11 C12 C7 -2.0(11) . . . . ? I4 C11 C12 C7 -11.0(17) . . . . ? F7 C11 C12 I3 -179.6(10) . . . . ? C10 C11 C12 I3 -1.3(18) . . . . ? I4 C11 C12 I3 -10(2) . . . . ? C8 C7 C12 F8 179.5(6) . . . . ? I3 C7 C12 F8 -0.7(10) . . . . ? C8 C7 C12 C11 -0.3(11) . . . . ? I3 C7 C12 C11 179.5(5) . . . . ? C8 C7 C12 I3 -179.8(10) . . . . ? C7 I3 C12 F8 179.4(9) . . . . ? C8 I3 C12 F8 179.5(5) . . . . ? S2 I3 C12 F8 1.5(7) . . . . ? N3 I3 C12 F8 44.9(5) . . . . ? N4 I3 C12 F8 136.9(3) 2_655 . . . ? N1 I3 C12 F8 -98.8(4) 2_645 . . . ? C7 I3 C12 C11 -1.0(12) . . . . ? C8 I3 C12 C11 -0.9(13) . . . . ? S2 I3 C12 C11 -178.9(11) . . . . ? N3 I3 C12 C11 -135.5(13) . . . . ? N4 I3 C12 C11 -43.5(15) 2_655 . . . ? N1 I3 C12 C11 80.8(14) 2_645 . . . ? C8 I3 C12 C7 0.1(6) . . . . ? S2 I3 C12 C7 -177.9(5) . . . . ? N3 I3 C12 C7 -134.5(6) . . . . ? N4 I3 C12 C7 -42.5(7) 2_655 . . . ? N1 I3 C12 C7 81.8(6) 2_645 . . . ? S1 N2 C13 N1 -179.6(11) . . . . ? N3 N2 C13 N1 61.7(7) . . . . ? S1 N2 C13 N1 172.0(5) 2_545 . . . ? N4 N2 C13 N1 81.0(8) . . . . ? I2 N2 C13 N1 -120.8(7) . . . . ? I4 N2 C13 N1 -2.5(9) 4_575 . . . ? N1 N2 C13 S1 179.6(11) . . . . ? N3 N2 C13 S1 -118.7(5) . . . . ? S1 N2 C13 S1 -8.4(9) 2_545 . . . ? N4 N2 C13 S1 -99.4(6) . . . . ? I2 N2 C13 S1 58.8(5) . . . . ? I4 N2 C13 S1 177.2(3) 4_575 . . . ? S1 N1 C13 N2 179.6(11) . . . . ? S1 N1 C13 N2 174.8(5) 2 . . . ? N3 N1 C13 N2 -57.9(6) . . . . ? I3 N1 C13 N2 12.9(18) 2_655 . . . ? I1 N1 C13 N2 120.9(6) 2 . . . ? N2 N1 C13 S1 -179.6(11) . . . . ? S1 N1 C13 S1 -4.9(9) 2 . . . ? N3 N1 C13 S1 122.5(5) . . . . ? I3 N1 C13 S1 -166.8(10) 2_655 . . . ? I1 N1 C13 S1 -58.8(6) 2 . . . ? N1 S1 C13 N2 -179.6(11) . . . . ? I1 S1 C13 N2 77.7(6) . . . . ? I2 S1 C13 N2 -66.8(6) . . . . ? N2 S1 C13 N2 -178.5(5) 2 . . . ? N1 S1 C13 N2 4.2(7) 2_545 . . . ? N4 S1 C13 N2 -117.1(6) 2 . . . ? N2 S1 C13 N1 179.6(11) . . . . ? I1 S1 C13 N1 -102.7(6) . . . . ? I2 S1 C13 N1 112.8(6) . . . . ? N2 S1 C13 N1 1.2(7) 2 . . . ? N1 S1 C13 N1 -176.2(4) 2_545 . . . ? N4 S1 C13 N1 62.5(7) 2 . . . ? S2 N4 C14 N3 177.2(11) . . . . ? F2 N4 C14 N3 -59.8(7) 3_666 . . . ? N2 N4 C14 N3 52.9(7) . . . . ? S2 N4 C14 N3 -165.6(5) 2_645 . . . ? I3 N4 C14 N3 134.6(6) 2_645 . . . ? S1 N4 C14 N3 52.6(11) 2_545 . . . ? I2 N4 C14 N3 -47.8(15) 2_545 . . . ? N3 N4 C14 S2 -177.2(11) . . . . ? F2 N4 C14 S2 123.0(5) 3_666 . . . ? N2 N4 C14 S2 -124.4(5) . . . . ? S2 N4 C14 S2 17.2(8) 2_645 . . . ? I3 N4 C14 S2 -42.6(7) 2_645 . . . ? S1 N4 C14 S2 -124.6(6) 2_545 . . . ? I2 N4 C14 S2 135.0(9) 2_545 . . . ? S2 N3 C14 N4 -177.2(11) . . . . ? N2 N3 C14 N4 -54.5(7) . . . . ? S2 N3 C14 N4 -171.8(5) 2_655 . . . ? N1 N3 C14 N4 -74.2(8) . . . . ? I3 N3 C14 N4 125.5(7) . . . . ? I1 N3 C14 N4 12.5(8) . . . . ? I4 N3 C14 N4 -114.3(7) 4_575 . . . ? N4 N3 C14 S2 177.2(11) . . . . ? N2 N3 C14 S2 122.7(5) . . . . ? S2 N3 C14 S2 5.4(9) 2_655 . . . ? N1 N3 C14 S2 103.0(6) . . . . ? I3 N3 C14 S2 -57.3(4) . . . . ? I1 N3 C14 S2 -170.3(3) . . . . ? I4 N3 C14 S2 63.0(4) 4_575 . . . ? N3 S2 C14 N4 177.2(10) . . . . ? I4 S2 C14 N4 94.9(6) 4_575 . . . ? I3 S2 C14 N4 -114.8(6) . . . . ? N3 S2 C14 N4 -9.9(7) 2_645 . . . ? N4 S2 C14 N4 177.7(4) 2_655 . . . ? N4 S2 C14 N3 -177.2(10) . . . . ? I4 S2 C14 N3 -82.3(6) 4_575 . . . ? I3 S2 C14 N3 67.9(6) . . . . ? N3 S2 C14 N3 172.9(4) 2_645 . . . ? N4 S2 C14 N3 0.4(7) 2_655 . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1B S1 0.86 2.60 3.442(7) 168.1 2 N1 H1A I3 0.86 3.32 3.931(7) 130.5 2_655 N2 H2B S1 0.86 2.58 3.427(7) 166.8 2_545 N2 H2A I4 0.86 3.03 3.888(7) 174.9 4_575 N3 H3A I1 0.86 3.02 3.853(7) 163.3 . N3 H3B S2 0.86 2.60 3.444(7) 166.4 2_655 N4 H4A I2 0.86 3.48 4.029(7) 124.5 2_545 N4 H4B S2 0.86 2.66 3.489(7) 162.0 2_645 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.789 _refine_diff_density_min -1.230 _refine_diff_density_rms 0.199 # Attachment 'CCDC724589.cif' data_cd2102a _database_code_depnum_ccdc_archive 'CCDC 724589' #TrackingRef 'CCDC724589.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ;2-mercaptobenzimidazole-1,2-diiodo-3,4,5,6-tetrafluorobenzene (1/1) ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H6 F4 I2 N2 S' _chemical_formula_weight 552.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2368(14) _cell_length_b 8.5594(15) _cell_length_c 12.643(3) _cell_angle_alpha 88.742(17) _cell_angle_beta 85.274(16) _cell_angle_gamma 66.509(10) _cell_volume 814.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4469 _cell_measurement_theta_min 3.0402 _cell_measurement_theta_max 26.3714 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 4.024 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7540 _exptl_absorpt_process_details ? _exptl_special_details ; REQABA Empirical Absorption Correction, Version 1.1, R.A. Jacobson, Molecular Structure Corp., The Woodlands, TX, 1998. ; _diffrn_ambient_temperature 293(2) _diffrn_source_power 2.0000 _diffrn_source_voltage 50.0000 _diffrn_source_current 40.0000 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury CCD (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6199 _diffrn_measurement_method dtprofit.ref _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_measurement_details ; scan: Number of images: 360 Slice: -90.0000 - 90.0000 Image width: 0.5000 Exp time: 25.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 0.0000 XTD: 27.8225 2theta: -0.0826 scan: Number of images: 120 Slice: -30.0000 - 30.0000 Image width: 0.5000 Exp time: 25.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 90.0000 XTD: 27.8225 2theta: -0.0826 ; _diffrn_measurement_device_details ; AFC8: Eulerian 3-circle ; _diffrn_standards_number NA _diffrn_standards_interval_count NA _diffrn_standards_interval_time NA _diffrn_standards_decay_% NA _diffrn_reflns_number 7873 _diffrn_reflns_av_R_equivalents 0.0648 _diffrn_reflns_av_sigmaI/netI 0.0843 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3288 _reflns_number_gt 1938 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear, V. 1.3 sp1 (Rigaku Corp., 2001)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2001)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2001)' _computing_structure_solution 'SHELXTL,VERSION 6.10 Sheldrick (2000)' _computing_structure_refinement 'SHELXTL,VERSION 6.10' _computing_molecular_graphics 'SHELXTL,VERSION 6.10' _computing_publication_material 'SHELXTL,VERSION 6.10' _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^)+(0.0011P)^2^+3.5103P] 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 calc _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3288 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1053 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.0884 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _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 0.59919(8) 0.17108(8) 0.28223(5) 0.05687(19) Uani 1 1 d . . . I2 I 0.27841(9) 0.43705(9) 0.49662(7) 0.0771(3) Uani 1 1 d . . . S1 S 0.5995(3) 0.2120(3) 0.02136(18) 0.0489(5) Uani 1 1 d . . . F1 F 0.4465(9) 0.2967(8) 0.7084(5) 0.099(2) Uani 1 1 d . . . F2 F 0.7365(10) 0.0387(9) 0.7585(4) 0.097(2) Uani 1 1 d . . . F3 F 0.9643(7) -0.1723(7) 0.6022(4) 0.0741(16) Uani 1 1 d . . . F4 F 0.8975(6) -0.1115(6) 0.3992(4) 0.0642(15) Uani 1 1 d . . . N1 N 0.3155(9) 0.4490(8) -0.0683(5) 0.0405(16) Uani 1 1 d . . . H1 H 0.3567 0.5297 -0.0575 0.049 Uiso 1 1 d R . . N2 N 0.3065(8) 0.1991(7) -0.0573(5) 0.0405(16) Uani 1 1 d . . . H2 H 0.3165 0.0934 -0.0396 0.049 Uiso 1 1 d R . . C1 C 0.6306(10) 0.1301(9) 0.4456(6) 0.0413(19) Uani 1 1 d . . . C2 C 0.5121(10) 0.2325(10) 0.5254(7) 0.050(2) Uani 1 1 d . . . C3 C 0.5560(14) 0.1979(13) 0.6290(7) 0.059(3) Uani 1 1 d . . . C4 C 0.7079(14) 0.0635(13) 0.6557(9) 0.066(3) Uani 1 1 d . . . C5 C 0.8169(12) -0.0390(11) 0.5780(7) 0.050(2) Uani 1 1 d . . . C6 C 0.7807(11) -0.0056(10) 0.4747(7) 0.046(2) Uani 1 1 d . . . C7 C 0.4027(11) 0.2873(9) -0.0355(6) 0.0376(18) Uani 1 1 d . . . C8 C 0.1632(10) 0.4612(9) -0.1112(6) 0.0378(18) Uani 1 1 d . . . C9 C 0.1543(10) 0.3050(10) -0.1056(6) 0.0409(19) Uani 1 1 d . . . C10 C 0.0179(12) 0.2761(11) -0.1419(7) 0.054(2) Uani 1 1 d . . . H10A H 0.0150 0.1687 -0.1369 0.065 Uiso 1 1 calc R . . C11 C -0.1146(12) 0.4075(14) -0.1858(8) 0.064(3) Uani 1 1 d . . . H11A H -0.2095 0.3910 -0.2111 0.077 Uiso 1 1 calc R . . C12 C -0.1061(12) 0.5662(13) -0.1922(7) 0.065(3) Uani 1 1 d . . . H12A H -0.1975 0.6549 -0.2221 0.078 Uiso 1 1 calc R . . C13 C 0.0290(11) 0.5982(11) -0.1571(7) 0.052(2) Uani 1 1 d . . . H13A H 0.0326 0.7053 -0.1630 0.063 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0553(4) 0.0644(4) 0.0524(4) 0.0055(3) -0.0116(3) -0.0243(3) I2 0.0513(4) 0.0546(4) 0.1166(7) -0.0074(4) 0.0035(4) -0.0132(3) S1 0.0576(13) 0.0360(10) 0.0566(14) 0.0091(9) -0.0236(11) -0.0193(10) F1 0.118(5) 0.096(5) 0.071(4) -0.030(3) 0.038(4) -0.038(4) F2 0.143(6) 0.140(6) 0.034(3) 0.018(3) -0.026(3) -0.080(5) F3 0.080(4) 0.075(4) 0.071(4) 0.019(3) -0.033(3) -0.031(3) F4 0.058(3) 0.063(3) 0.057(3) -0.004(3) 0.000(3) -0.009(3) N1 0.052(4) 0.028(3) 0.040(4) 0.001(3) -0.010(3) -0.013(3) N2 0.052(4) 0.028(3) 0.045(4) 0.003(3) -0.010(3) -0.018(3) C1 0.045(4) 0.034(4) 0.045(5) 0.004(3) 0.001(4) -0.016(4) C2 0.041(5) 0.042(5) 0.066(6) -0.008(4) 0.009(4) -0.018(4) C3 0.073(6) 0.069(6) 0.045(6) -0.022(5) 0.023(5) -0.043(5) C4 0.064(6) 0.069(7) 0.073(7) 0.006(6) -0.017(6) -0.034(6) C5 0.049(5) 0.045(5) 0.058(6) 0.007(4) -0.006(4) -0.022(4) C6 0.049(5) 0.044(5) 0.048(5) -0.006(4) 0.002(4) -0.022(4) C7 0.065(5) 0.026(4) 0.032(4) -0.001(3) -0.011(4) -0.027(4) C8 0.045(5) 0.032(4) 0.035(4) 0.003(3) -0.008(4) -0.012(4) C9 0.034(4) 0.049(5) 0.038(4) -0.005(4) 0.000(3) -0.016(4) C10 0.060(6) 0.047(5) 0.060(6) 0.003(4) -0.003(5) -0.027(5) C11 0.048(6) 0.080(7) 0.070(7) 0.008(6) -0.019(5) -0.028(5) C12 0.048(5) 0.077(7) 0.060(6) 0.020(5) -0.013(5) -0.014(5) C13 0.048(5) 0.050(5) 0.054(5) 0.003(4) -0.007(4) -0.015(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.107(8) . ? I1 C6 3.014(9) . ? I1 C2 3.106(9) . ? I1 F4 3.127(5) . ? I1 S1 3.309(2) . ? I1 I2 3.7157(13) . ? I1 I2 4.8639(13) 2_666 ? I2 C2 2.074(8) . ? I2 C3 2.994(12) . ? I2 C1 3.070(7) . ? I2 F1 3.110(7) . ? I2 F3 3.520(6) 1_465 ? I2 I2 4.2055(16) 2_666 ? I2 I2 4.2665(16) 2_566 ? I2 I1 4.8639(13) 2_666 ? S1 C7 1.703(8) . ? S1 N1 2.725(6) . ? S1 N2 2.727(7) . ? F1 C3 1.347(9) . ? F2 C4 1.338(11) . ? F3 C5 1.346(9) . ? F3 I2 3.520(6) 1_645 ? F4 C6 1.360(8) . ? N1 C7 1.355(9) . ? N1 C8 1.373(10) . ? N1 H1 0.9001 . ? N2 C7 1.340(9) . ? N2 C9 1.401(9) . ? N2 H2 0.9000 . ? C1 C2 1.391(10) . ? C1 C6 1.387(10) . ? C2 C3 1.382(12) . ? C3 C4 1.381(13) . ? C4 C5 1.344(12) . ? C5 C6 1.361(11) . ? C8 C9 1.367(10) . ? C8 C13 1.406(10) . ? C9 C10 1.359(11) . ? C10 C11 1.363(12) . ? C10 H10A 0.9300 . ? C11 C12 1.388(13) . ? C11 H11A 0.9300 . ? C12 C13 1.357(12) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 I1 C6 24.1(2) . . ? C1 I1 C2 21.8(2) . . ? C6 I1 C2 45.8(2) . . ? C1 I1 F4 49.6(2) . . ? C6 I1 F4 25.51(16) . . ? C2 I1 F4 71.34(17) . . ? C1 I1 S1 173.5(2) . . ? C6 I1 S1 149.85(16) . . ? C2 I1 S1 163.91(15) . . ? F4 I1 S1 124.48(10) . . ? C1 I1 I2 55.7(2) . . ? C6 I1 I2 79.77(15) . . ? C2 I1 I2 33.93(15) . . ? F4 I1 I2 105.25(9) . . ? S1 I1 I2 130.24(4) . . ? C1 I1 I2 58.0(2) . 2_666 ? C6 I1 I2 68.96(16) . 2_666 ? C2 I1 I2 52.32(16) . 2_666 ? F4 I1 I2 84.48(10) . 2_666 ? S1 I1 I2 121.44(4) . 2_666 ? I2 I1 I2 56.83(2) . 2_666 ? C2 I2 C3 23.9(3) . . ? C2 I2 C1 22.2(3) . . ? C3 I2 C1 46.0(2) . . ? C2 I2 F1 49.3(3) . . ? C3 I2 F1 25.41(17) . . ? C1 I2 F1 71.46(18) . . ? C2 I2 F3 143.5(3) . 1_465 ? C3 I2 F3 120.87(18) . 1_465 ? C1 I2 F3 161.44(18) . 1_465 ? F1 I2 F3 96.28(13) . 1_465 ? C2 I2 I1 56.7(2) . . ? C3 I2 I1 80.55(16) . . ? C1 I2 I1 34.55(15) . . ? F1 I2 I1 105.94(10) . . ? F3 I2 I1 152.45(9) 1_465 . ? C2 I2 I2 65.8(2) . 2_666 ? C3 I2 I2 67.38(19) . 2_666 ? C1 I2 I2 67.54(15) . 2_666 ? F1 I2 I2 73.52(13) . 2_666 ? F3 I2 I2 96.01(10) 1_465 2_666 ? I1 I2 I2 75.48(3) . 2_666 ? C2 I2 I2 139.9(2) . 2_566 ? C3 I2 I2 131.14(18) . 2_566 ? C1 I2 I2 139.09(16) . 2_566 ? F1 I2 I2 114.80(12) . 2_566 ? F3 I2 I2 58.38(9) 1_465 2_566 ? I1 I2 I2 122.56(3) . 2_566 ? I2 I2 I2 152.94(4) 2_666 2_566 ? C2 I2 I1 93.7(2) . 2_666 ? C3 I2 I1 78.04(18) . 2_666 ? C1 I2 I1 107.39(16) . 2_666 ? F1 I2 I1 62.93(12) . 2_666 ? F3 I2 I1 54.07(9) 1_465 2_666 ? I1 I2 I1 123.17(2) . 2_666 ? I2 I2 I1 47.69(2) 2_666 2_666 ? I2 I2 I1 111.03(3) 2_566 2_666 ? C7 S1 N1 23.8(3) . . ? C7 S1 N2 23.1(3) . . ? N1 S1 N2 46.91(19) . . ? C7 S1 I1 119.2(3) . . ? N1 S1 I1 120.65(15) . . ? N2 S1 I1 113.17(15) . . ? C3 F1 I2 72.5(6) . . ? C5 F3 I2 141.2(5) . 1_645 ? C6 F4 I1 72.6(4) . . ? C7 N1 C8 109.0(7) . . ? C7 N1 S1 30.5(4) . . ? C8 N1 S1 139.5(5) . . ? C7 N1 H1 120.8 . . ? C8 N1 H1 130.1 . . ? S1 N1 H1 90.3 . . ? C7 N2 C9 110.0(6) . . ? C7 N2 S1 29.9(4) . . ? C9 N2 S1 139.9(5) . . ? C7 N2 H2 131.7 . . ? C9 N2 H2 117.8 . . ? S1 N2 H2 102.1 . . ? C2 C1 C6 118.3(8) . . ? C2 C1 I1 124.0(6) . . ? C6 C1 I1 117.7(6) . . ? C2 C1 I2 34.3(4) . . ? C6 C1 I2 152.6(6) . . ? I1 C1 I2 89.7(2) . . ? C3 C2 C1 117.7(8) . . ? C3 C2 I2 118.7(6) . . ? C1 C2 I2 123.6(7) . . ? C3 C2 I1 151.8(6) . . ? C1 C2 I1 34.2(4) . . ? I2 C2 I1 89.4(3) . . ? F1 C3 C4 117.8(9) . . ? F1 C3 C2 119.5(9) . . ? C4 C3 C2 122.7(8) . . ? F1 C3 I2 82.1(6) . . ? C4 C3 I2 160.1(7) . . ? C2 C3 I2 37.4(4) . . ? F2 C4 C5 123.1(9) . . ? F2 C4 C3 118.1(9) . . ? C5 C4 C3 118.8(9) . . ? C4 C5 F3 119.8(9) . . ? C4 C5 C6 120.1(8) . . ? F3 C5 C6 120.1(8) . . ? F4 C6 C5 117.6(7) . . ? F4 C6 C1 120.1(7) . . ? C5 C6 C1 122.3(7) . . ? F4 C6 I1 81.9(4) . . ? C5 C6 I1 160.4(6) . . ? C1 C6 I1 38.2(4) . . ? N2 C7 N1 107.3(7) . . ? N2 C7 S1 127.0(6) . . ? N1 C7 S1 125.7(6) . . ? C9 C8 N1 108.4(6) . . ? C9 C8 C13 119.9(8) . . ? N1 C8 C13 131.7(8) . . ? C10 C9 C8 122.4(8) . . ? C10 C9 N2 132.3(8) . . ? C8 C9 N2 105.3(7) . . ? C9 C10 C11 118.8(9) . . ? C9 C10 H10A 120.6 . . ? C11 C10 H10A 120.6 . . ? C10 C11 C12 119.2(9) . . ? C10 C11 H11A 120.4 . . ? C12 C11 H11A 120.4 . . ? C13 C12 C11 123.2(9) . . ? C13 C12 H12A 118.4 . . ? C11 C12 H12A 118.4 . . ? C12 C13 C8 116.5(9) . . ? C12 C13 H13A 121.7 . . ? C8 C13 H13A 121.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 I1 I2 C2 1.0(4) . . . . ? C6 I1 I2 C2 1.1(3) . . . . ? F4 I1 I2 C2 2.4(3) . . . . ? S1 I1 I2 C2 -175.6(3) . . . . ? I2 I1 I2 C2 -70.3(3) 2_666 . . . ? C1 I1 I2 C3 2.4(3) . . . . ? C6 I1 I2 C3 2.5(3) . . . . ? C2 I1 I2 C3 1.4(3) . . . . ? F4 I1 I2 C3 3.8(2) . . . . ? S1 I1 I2 C3 -174.2(2) . . . . ? I2 I1 I2 C3 -68.92(19) 2_666 . . . ? C6 I1 I2 C1 0.1(3) . . . . ? C2 I1 I2 C1 -1.0(4) . . . . ? F4 I1 I2 C1 1.4(3) . . . . ? S1 I1 I2 C1 -176.6(3) . . . . ? I2 I1 I2 C1 -71.3(3) 2_666 . . . ? C1 I1 I2 F1 3.6(3) . . . . ? C6 I1 I2 F1 3.7(2) . . . . ? C2 I1 I2 F1 2.6(3) . . . . ? F4 I1 I2 F1 4.97(18) . . . . ? S1 I1 I2 F1 -173.00(15) . . . . ? I2 I1 I2 F1 -67.74(14) 2_666 . . . ? C1 I1 I2 F3 146.1(3) . . . 1_465 ? C6 I1 I2 F3 146.2(3) . . . 1_465 ? C2 I1 I2 F3 145.1(3) . . . 1_465 ? F4 I1 I2 F3 147.5(2) . . . 1_465 ? S1 I1 I2 F3 -30.5(2) . . . 1_465 ? I2 I1 I2 F3 74.8(2) 2_666 . . 1_465 ? C1 I1 I2 I2 71.3(3) . . . 2_666 ? C6 I1 I2 I2 71.47(17) . . . 2_666 ? C2 I1 I2 I2 70.3(3) . . . 2_666 ? F4 I1 I2 I2 72.71(11) . . . 2_666 ? S1 I1 I2 I2 -105.26(6) . . . 2_666 ? C1 I1 I2 I2 -130.8(3) . . . 2_566 ? C6 I1 I2 I2 -130.70(17) . . . 2_566 ? C2 I1 I2 I2 -131.8(3) . . . 2_566 ? F4 I1 I2 I2 -129.46(11) . . . 2_566 ? S1 I1 I2 I2 52.57(7) . . . 2_566 ? I2 I1 I2 I2 157.83(5) 2_666 . . 2_566 ? C1 I1 I2 I1 71.3(3) . . . 2_666 ? C6 I1 I2 I1 71.47(17) . . . 2_666 ? C2 I1 I2 I1 70.3(3) . . . 2_666 ? F4 I1 I2 I1 72.71(11) . . . 2_666 ? S1 I1 I2 I1 -105.26(6) . . . 2_666 ? I2 I1 I2 I1 0.0 2_666 . . 2_666 ? C1 I1 S1 C7 170.4(19) . . . . ? C6 I1 S1 C7 151.3(4) . . . . ? C2 I1 S1 C7 -44.0(7) . . . . ? F4 I1 S1 C7 147.3(3) . . . . ? I2 I1 S1 C7 -35.1(3) . . . . ? I2 I1 S1 C7 -106.3(3) 2_666 . . . ? C1 I1 S1 N1 -162.1(19) . . . . ? C6 I1 S1 N1 178.8(4) . . . . ? C2 I1 S1 N1 -16.5(6) . . . . ? F4 I1 S1 N1 174.8(2) . . . . ? I2 I1 S1 N1 -7.6(2) . . . . ? I2 I1 S1 N1 -78.76(19) 2_666 . . . ? C1 I1 S1 N2 145.5(19) . . . . ? C6 I1 S1 N2 126.4(4) . . . . ? C2 I1 S1 N2 -68.9(6) . . . . ? F4 I1 S1 N2 122.38(19) . . . . ? I2 I1 S1 N2 -60.00(16) . . . . ? I2 I1 S1 N2 -131.16(14) 2_666 . . . ? C2 I2 F1 C3 0.1(6) . . . . ? C1 I2 F1 C3 -0.6(5) . . . . ? F3 I2 F1 C3 -166.3(5) 1_465 . . . ? I1 I2 F1 C3 -2.7(5) . . . . ? I2 I2 F1 C3 -71.8(5) 2_666 . . . ? I2 I2 F1 C3 135.8(5) 2_566 . . . ? I1 I2 F1 C3 -122.3(5) 2_666 . . . ? C1 I1 F4 C6 -1.4(5) . . . . ? C2 I1 F4 C6 -1.4(5) . . . . ? S1 I1 F4 C6 175.3(4) . . . . ? I2 I1 F4 C6 -2.8(5) . . . . ? I2 I1 F4 C6 50.6(4) 2_666 . . . ? N2 S1 N1 C7 0.5(7) . . . . ? I1 S1 N1 C7 -93.7(7) . . . . ? C7 S1 N1 C8 -1.2(8) . . . . ? N2 S1 N1 C8 -0.7(7) . . . . ? I1 S1 N1 C8 -94.9(7) . . . . ? N1 S1 N2 C7 -0.5(7) . . . . ? I1 S1 N2 C7 110.6(7) . . . . ? C7 S1 N2 C9 1.5(8) . . . . ? N1 S1 N2 C9 1.0(7) . . . . ? I1 S1 N2 C9 112.0(7) . . . . ? C6 I1 C1 C2 178.8(12) . . . . ? F4 I1 C1 C2 -179.8(9) . . . . ? S1 I1 C1 C2 155.1(15) . . . . ? I2 I1 C1 C2 -1.5(6) . . . . ? I2 I1 C1 C2 67.7(7) 2_666 . . . ? C2 I1 C1 C6 -178.8(12) . . . . ? F4 I1 C1 C6 1.4(5) . . . . ? S1 I1 C1 C6 -24(2) . . . . ? I2 I1 C1 C6 179.7(7) . . . . ? I2 I1 C1 C6 -111.1(7) 2_666 . . . ? C6 I1 C1 I2 -179.7(7) . . . . ? C2 I1 C1 I2 1.5(6) . . . . ? F4 I1 C1 I2 -178.3(4) . . . . ? S1 I1 C1 I2 156.6(18) . . . . ? I2 I1 C1 I2 69.20(15) 2_666 . . . ? C3 I2 C1 C2 1.1(7) . . . . ? F1 I2 C1 C2 1.4(7) . . . . ? F3 I2 C1 C2 51.9(10) 1_465 . . . ? I1 I2 C1 C2 177.7(8) . . . . ? I2 I2 C1 C2 80.7(7) 2_666 . . . ? I2 I2 C1 C2 -105.4(7) 2_566 . . . ? I1 I2 C1 C2 53.9(7) 2_666 . . . ? C2 I2 C1 C6 2.8(12) . . . . ? C3 I2 C1 C6 3.9(12) . . . . ? F1 I2 C1 C6 4.2(12) . . . . ? F3 I2 C1 C6 54.7(15) 1_465 . . . ? I1 I2 C1 C6 -179.4(14) . . . . ? I2 I2 C1 C6 83.5(13) 2_666 . . . ? I2 I2 C1 C6 -102.6(12) 2_566 . . . ? I1 I2 C1 C6 56.8(13) 2_666 . . . ? C2 I2 C1 I1 -177.7(8) . . . . ? C3 I2 C1 I1 -176.7(4) . . . . ? F1 I2 C1 I1 -176.3(3) . . . . ? F3 I2 C1 I1 -125.9(5) 1_465 . . . ? I2 I2 C1 I1 -97.0(2) 2_666 . . . ? I2 I2 C1 I1 76.9(3) 2_566 . . . ? I1 I2 C1 I1 -123.8(2) 2_666 . . . ? C6 C1 C2 C3 3.3(12) . . . . ? I1 C1 C2 C3 -175.4(7) . . . . ? I2 C1 C2 C3 -178.1(12) . . . . ? C6 C1 C2 I2 -178.5(6) . . . . ? I1 C1 C2 I2 2.7(10) . . . . ? C6 C1 C2 I1 178.7(12) . . . . ? I2 C1 C2 I1 -2.7(10) . . . . ? C1 I2 C2 C3 178.1(13) . . . . ? F1 I2 C2 C3 -0.1(6) . . . . ? F3 I2 C2 C3 23.0(10) 1_465 . . . ? I1 I2 C2 C3 176.6(8) . . . . ? I2 I2 C2 C3 88.5(7) 2_666 . . . ? I2 I2 C2 C3 -80.7(8) 2_566 . . . ? I1 I2 C2 C3 48.7(7) 2_666 . . . ? C3 I2 C2 C1 -178.1(13) . . . . ? F1 I2 C2 C1 -178.3(9) . . . . ? F3 I2 C2 C1 -155.1(5) 1_465 . . . ? I1 I2 C2 C1 -1.5(6) . . . . ? I2 I2 C2 C1 -89.6(7) 2_666 . . . ? I2 I2 C2 C1 101.1(7) 2_566 . . . ? I1 I2 C2 C1 -129.4(7) 2_666 . . . ? C3 I2 C2 I1 -176.6(8) . . . . ? C1 I2 C2 I1 1.5(6) . . . . ? F1 I2 C2 I1 -176.7(4) . . . . ? F3 I2 C2 I1 -153.6(3) 1_465 . . . ? I2 I2 C2 I1 -88.07(18) 2_666 . . . ? I2 I2 C2 I1 102.7(3) 2_566 . . . ? I1 I2 C2 I1 -127.83(15) 2_666 . . . ? C1 I1 C2 C3 8.6(12) . . . . ? C6 I1 C2 C3 7.9(13) . . . . ? F4 I1 C2 C3 8.8(13) . . . . ? S1 I1 C2 C3 -161.4(10) . . . . ? I2 I1 C2 C3 -173.6(15) . . . . ? I2 I1 C2 C3 -88.8(14) 2_666 . . . ? C6 I1 C2 C1 -0.7(7) . . . . ? F4 I1 C2 C1 0.2(7) . . . . ? S1 I1 C2 C1 -170.0(6) . . . . ? I2 I1 C2 C1 177.7(9) . . . . ? I2 I1 C2 C1 -97.5(7) 2_666 . . . ? C1 I1 C2 I2 -177.7(9) . . . . ? C6 I1 C2 I2 -178.4(5) . . . . ? F4 I1 C2 I2 -177.6(3) . . . . ? S1 I1 C2 I2 12.2(8) . . . . ? I2 I1 C2 I2 84.8(2) 2_666 . . . ? I2 F1 C3 C4 -179.3(9) . . . . ? I2 F1 C3 C2 -0.2(7) . . . . ? C1 C2 C3 F1 178.5(8) . . . . ? I2 C2 C3 F1 0.3(12) . . . . ? I1 C2 C3 F1 173.0(8) . . . . ? C1 C2 C3 C4 -2.4(14) . . . . ? I2 C2 C3 C4 179.4(8) . . . . ? I1 C2 C3 C4 -8(2) . . . . ? C1 C2 C3 I2 178.2(12) . . . . ? I1 C2 C3 I2 172.8(17) . . . . ? C2 I2 C3 F1 -179.7(11) . . . . ? C1 I2 C3 F1 179.3(7) . . . . ? F3 I2 C3 F1 16.0(6) 1_465 . . . ? I1 I2 C3 F1 177.4(5) . . . . ? I2 I2 C3 F1 99.2(5) 2_666 . . . ? I2 I2 C3 F1 -57.3(6) 2_566 . . . ? I1 I2 C3 F1 50.3(5) 2_666 . . . ? C2 I2 C3 C4 -1.6(19) . . . . ? C1 I2 C3 C4 -3(2) . . . . ? F1 I2 C3 C4 178(2) . . . . ? F3 I2 C3 C4 -166(2) 1_465 . . . ? I1 I2 C3 C4 -4(2) . . . . ? I2 I2 C3 C4 -83(2) 2_666 . . . ? I2 I2 C3 C4 121(2) 2_566 . . . ? I1 I2 C3 C4 -132(2) 2_666 . . . ? C1 I2 C3 C2 -1.0(7) . . . . ? F1 I2 C3 C2 179.7(11) . . . . ? F3 I2 C3 C2 -164.3(7) 1_465 . . . ? I1 I2 C3 C2 -2.9(7) . . . . ? I2 I2 C3 C2 -81.0(7) 2_666 . . . ? I2 I2 C3 C2 122.5(7) 2_566 . . . ? I1 I2 C3 C2 -129.9(7) 2_666 . . . ? F1 C3 C4 F2 0.5(14) . . . . ? C2 C3 C4 F2 -178.6(9) . . . . ? I2 C3 C4 F2 -177.5(16) . . . . ? F1 C3 C4 C5 178.5(9) . . . . ? C2 C3 C4 C5 -0.6(15) . . . . ? I2 C3 C4 C5 1(3) . . . . ? F2 C4 C5 F3 -1.2(14) . . . . ? C3 C4 C5 F3 -179.0(8) . . . . ? F2 C4 C5 C6 -179.5(9) . . . . ? C3 C4 C5 C6 2.7(14) . . . . ? I2 F3 C5 C4 160.6(7) 1_645 . . . ? I2 F3 C5 C6 -21.2(13) 1_645 . . . ? I1 F4 C6 C5 -178.5(8) . . . . ? I1 F4 C6 C1 1.8(6) . . . . ? C4 C5 C6 F4 178.6(8) . . . . ? F3 C5 C6 F4 0.3(12) . . . . ? C4 C5 C6 C1 -1.7(14) . . . . ? F3 C5 C6 C1 -180.0(8) . . . . ? C4 C5 C6 I1 3(3) . . . . ? F3 C5 C6 I1 -175.1(14) . . . . ? C2 C1 C6 F4 178.3(8) . . . . ? I1 C1 C6 F4 -2.9(10) . . . . ? I2 C1 C6 F4 176.5(8) . . . . ? C2 C1 C6 C5 -1.4(13) . . . . ? I1 C1 C6 C5 177.4(7) . . . . ? I2 C1 C6 C5 -3.2(18) . . . . ? C2 C1 C6 I1 -178.8(11) . . . . ? I2 C1 C6 I1 179.4(16) . . . . ? C1 I1 C6 F4 177.5(9) . . . . ? C2 I1 C6 F4 178.1(6) . . . . ? S1 I1 C6 F4 -7.8(7) . . . . ? I2 I1 C6 F4 177.2(4) . . . . ? I2 I1 C6 F4 -124.5(5) 2_666 . . . ? C1 I1 C6 C5 -6.6(17) . . . . ? C2 I1 C6 C5 -6.0(18) . . . . ? F4 I1 C6 C5 176(2) . . . . ? S1 I1 C6 C5 168.2(17) . . . . ? I2 I1 C6 C5 -6.8(19) . . . . ? I2 I1 C6 C5 51.4(19) 2_666 . . . ? C2 I1 C6 C1 0.6(6) . . . . ? F4 I1 C6 C1 -177.5(9) . . . . ? S1 I1 C6 C1 174.8(6) . . . . ? I2 I1 C6 C1 -0.2(6) . . . . ? I2 I1 C6 C1 58.0(6) 2_666 . . . ? C9 N2 C7 N1 0.3(8) . . . . ? S1 N2 C7 N1 179.3(11) . . . . ? C9 N2 C7 S1 -179.0(6) . . . . ? C8 N1 C7 N2 -0.1(8) . . . . ? S1 N1 C7 N2 -179.3(10) . . . . ? C8 N1 C7 S1 179.2(6) . . . . ? N1 S1 C7 N2 179.1(12) . . . . ? I1 S1 C7 N2 -80.6(7) . . . . ? N2 S1 C7 N1 -179.1(12) . . . . ? I1 S1 C7 N1 100.3(7) . . . . ? C7 N1 C8 C9 -0.1(8) . . . . ? S1 N1 C8 C9 0.5(11) . . . . ? C7 N1 C8 C13 -179.2(8) . . . . ? S1 N1 C8 C13 -178.6(6) . . . . ? N1 C8 C9 C10 179.9(8) . . . . ? C13 C8 C9 C10 -0.8(12) . . . . ? N1 C8 C9 N2 0.3(8) . . . . ? C13 C8 C9 N2 179.5(7) . . . . ? C7 N2 C9 C10 -180.0(8) . . . . ? S1 N2 C9 C10 179.2(7) . . . . ? C7 N2 C9 C8 -0.4(8) . . . . ? S1 N2 C9 C8 -1.1(10) . . . . ? C8 C9 C10 C11 0.2(13) . . . . ? N2 C9 C10 C11 179.8(8) . . . . ? C9 C10 C11 C12 0.1(14) . . . . ? C10 C11 C12 C13 0.2(15) . . . . ? C11 C12 C13 C8 -0.8(14) . . . . ? C9 C8 C13 C12 1.1(12) . . . . ? N1 C8 C13 C12 -179.9(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S1 0.90 2.44 3.320(7) 167.6 2_665 N2 H2 S1 0.90 2.43 3.317(6) 167.1 2_655 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.655 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.128 # Attachment 'CCDC724667.cif' data_cd5104a _database_code_depnum_ccdc_archive 'CCDC 724667' #TrackingRef 'CCDC724667.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'ethylenethiourea-tetraiodoethylene (2/3)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 I12 N4 S2' _chemical_formula_weight 1799.18 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.504(2) _cell_length_b 8.2442(9) _cell_length_c 20.428(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.487(9) _cell_angle_gamma 90.00 _cell_volume 3263.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 8210 _cell_measurement_theta_min 2.7376 _cell_measurement_theta_max 26.0212 _exptl_crystal_description Tabular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3120 _exptl_absorpt_coefficient_mu 11.527 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.6859 _exptl_absorpt_process_details ? _exptl_special_details ; REQABA Empirical Absorption Correction, Version 1.1, R.A. Jacobson, Molecular Structure Corp., The Woodlands, TX, 1998. ; _diffrn_ambient_temperature 163(2) _diffrn_source_power 2.0000 _diffrn_source_voltage 50.0000 _diffrn_source_current 40.0000 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Sealed Tube' _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_detector CCD _diffrn_measurement_device ; Mercury CCD (2x2 bin mode) ; _diffrn_detector_area_resol_mean 14.6199 _diffrn_measurement_method dtprofit.ref _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_measurement_details ; scan: Number of images: 360 Slice: -90.0000 - 90.0000 Image width: 0.5000 Exp time: 25.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 0.0000 XTD: 27.8225 2theta: -0.0826 scan: Number of images: 120 Slice: -30.0000 - 30.0000 Image width: 0.5000 Exp time: 25.0000 Rotation axis: Omega Omega: 0.0000 Chi: 45.0000 Phi: 90.0000 XTD: 27.8225 2theta: -0.0826 ; _diffrn_measurement_device_details ; AFC8: Eulerian 3-circle ; _diffrn_standards_number NA _diffrn_standards_interval_count NA _diffrn_standards_interval_time NA _diffrn_standards_decay_% NA _diffrn_reflns_number 13808 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 26.02 _reflns_number_total 3191 _reflns_number_gt 3127 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear, V. 1.3 sp1 (Rigaku Corp., 2001)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2001)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2001)' _computing_structure_solution 'SHELXTL,VERSION 6.10 Sheldrick (2000)' _computing_structure_refinement 'SHELXTL,VERSION 6.10' _computing_molecular_graphics 'SHELXTL,VERSION 6.10' _computing_publication_material 'SHELXTL,VERSION 6.10' _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^)+(0.0046P)^2^+85.3322P] 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 calc _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3191 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0572 _refine_ls_wR_factor_gt 0.0568 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.089890(17) 0.94065(4) 0.266609(17) 0.01509(9) Uani 1 1 d . . . I2 I 0.089810(18) 0.49446(5) 0.269116(17) 0.01717(9) Uani 1 1 d . . . I3 I 0.14823(2) 1.20089(5) 0.435564(19) 0.02275(10) Uani 1 1 d . . . I4 I 0.12640(2) 1.30732(5) 0.597461(18) 0.02630(10) Uani 1 1 d . . . I5 I -0.03637(2) 1.17372(6) 0.395341(19) 0.02662(10) Uani 1 1 d . . . I6 I -0.05807(2) 1.30059(6) 0.55667(2) 0.03013(11) Uani 1 1 d . . . S1 S 0.22228(7) 1.20635(16) 0.27946(7) 0.0156(3) Uani 1 1 d . . . N1 N 0.2315(3) 1.3359(6) 0.1598(2) 0.0192(10) Uani 1 1 d . . . H1A H 0.2300 1.4334 0.1746 0.023 Uiso 1 1 calc R . . N2 N 0.2271(3) 1.0725(6) 0.1595(2) 0.0185(10) Uani 1 1 d . . . H2A H 0.2224 0.9758 0.1741 0.022 Uiso 1 1 calc R . . C1 C 0.0000 0.7974(10) 0.2500 0.0157(15) Uani 1 2 d S . . C2 C 0.0000 0.6368(11) 0.2500 0.0167(16) Uani 1 2 d S . . C3 C 0.0783(3) 1.2480(7) 0.5039(2) 0.0153(11) Uani 1 1 d . . . C4 C 0.0103(3) 1.2412(7) 0.4885(2) 0.0149(11) Uani 1 1 d . . . C5 C 0.2273(2) 1.2051(6) 0.1967(3) 0.0107(10) Uani 1 1 d . . . C6 C 0.2388(3) 1.2966(7) 0.0914(3) 0.0217(12) Uani 1 1 d . . . H6A H 0.2824 1.3352 0.0789 0.026 Uiso 1 1 calc R . . H6B H 0.2014 1.3424 0.0617 0.026 Uiso 1 1 calc R . . C7 C 0.2357(3) 1.1097(8) 0.0916(3) 0.0230(13) Uani 1 1 d . . . H7A H 0.1970 1.0702 0.0619 0.028 Uiso 1 1 calc R . . H7B H 0.2780 1.0630 0.0791 0.028 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 0.01125(16) 0.01809(18) 0.01591(17) -0.00234(13) 0.00137(12) -0.00368(13) I2 0.01340(17) 0.01892(19) 0.01898(18) 0.00270(14) 0.00096(13) 0.00506(13) I3 0.02030(19) 0.0284(2) 0.02046(19) -0.00123(15) 0.00618(14) 0.00105(16) I4 0.0348(2) 0.0287(2) 0.01403(18) -0.00290(15) -0.00313(15) -0.00984(18) I5 0.02066(19) 0.0389(2) 0.01872(19) -0.00338(16) -0.00453(15) 0.00021(17) I6 0.0281(2) 0.0399(3) 0.0247(2) 0.00240(18) 0.01322(16) 0.00625(18) S1 0.0196(7) 0.0121(6) 0.0151(6) 0.0001(5) 0.0018(5) -0.0009(5) N1 0.030(3) 0.011(2) 0.017(2) -0.0011(18) 0.002(2) 0.000(2) N2 0.028(3) 0.010(2) 0.017(2) -0.0003(18) 0.0014(19) 0.0009(19) C1 0.012(3) 0.019(4) 0.016(4) 0.000 0.000(3) 0.000 C2 0.014(4) 0.025(4) 0.012(3) 0.000 0.002(3) 0.000 C3 0.022(3) 0.015(3) 0.009(2) 0.000(2) 0.002(2) -0.001(2) C4 0.016(3) 0.019(3) 0.010(2) 0.001(2) 0.0034(19) 0.002(2) C5 0.005(2) 0.010(2) 0.016(2) 0.000(2) -0.0026(18) -0.0011(19) C6 0.030(3) 0.018(3) 0.018(3) 0.000(2) 0.007(2) -0.001(2) C7 0.031(3) 0.019(3) 0.020(3) -0.003(2) 0.009(2) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.109(5) . ? I1 S1 3.3736(14) . ? I1 I1 3.4954(8) 2 ? I1 I2 3.6788(7) . ? I1 I5 3.8661(7) 2 ? I2 C2 2.108(5) . ? I2 S1 3.4983(14) 1_545 ? I2 I2 3.5021(8) 2 ? I3 C3 2.095(5) . ? I3 I4 3.4939(7) . ? I3 I5 3.6083(7) . ? I3 S1 3.6465(15) . ? I4 C3 2.089(5) . ? I4 I6 3.6006(7) . ? I4 S1 3.6563(15) 7_576 ? I5 C4 2.090(5) . ? I5 I6 3.5283(7) . ? I5 I1 3.8661(7) 2 ? I6 C4 2.093(5) . ? S1 C5 1.705(5) . ? S1 N1 2.692(5) . ? S1 N2 2.698(5) . ? S1 I2 3.4983(14) 1_565 ? S1 I4 3.6563(15) 7_576 ? N1 C5 1.323(7) . ? N1 C6 1.458(7) . ? N1 H1A 0.8600 . ? N2 C5 1.331(7) . ? N2 C7 1.450(7) . ? N2 H2A 0.8600 . ? C1 C2 1.324(12) . ? C1 I1 2.109(5) 2 ? C2 I2 2.108(5) 2 ? C3 C4 1.329(8) . ? C6 C7 1.542(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 I1 S1 172.31(16) . . ? C1 I1 I1 34.05(19) . 2 ? S1 I1 I1 139.23(2) . 2 ? C1 I1 I2 55.99(18) . . ? S1 I1 I2 130.52(3) . . ? I1 I1 I2 90.040(8) 2 . ? C1 I1 I5 90.08(11) . 2 ? S1 I1 I5 82.77(3) . 2 ? I1 I1 I5 70.483(13) 2 2 ? I2 I1 I5 120.556(13) . 2 ? C2 I2 S1 169.04(17) . 1_545 ? C2 I2 I2 33.8(2) . 2 ? S1 I2 I2 136.62(2) 1_545 2 ? C2 I2 I1 56.1(2) . . ? S1 I2 I1 132.71(3) 1_545 . ? I2 I2 I1 89.936(8) 2 . ? C3 I3 I4 33.34(15) . . ? C3 I3 I5 57.00(15) . . ? I4 I3 I5 90.341(15) . . ? C3 I3 S1 158.79(15) . . ? I4 I3 S1 158.02(3) . . ? I5 I3 S1 106.57(3) . . ? C3 I4 I3 33.45(15) . . ? C3 I4 I6 56.71(15) . . ? I3 I4 I6 90.144(15) . . ? C3 I4 S1 149.97(16) . 7_576 ? I3 I4 S1 117.90(3) . 7_576 ? I6 I4 S1 150.06(3) . 7_576 ? C4 I5 I6 32.51(14) . . ? C4 I5 I3 56.98(14) . . ? I6 I5 I3 89.474(15) . . ? C4 I5 I1 163.57(15) . 2 ? I6 I5 I1 153.808(16) . 2 ? I3 I5 I1 113.062(15) . 2 ? C4 I6 I5 32.46(15) . . ? C4 I6 I4 57.46(15) . . ? I5 I6 I4 89.918(15) . . ? C5 S1 N1 23.7(2) . . ? C5 S1 N2 23.8(2) . . ? N1 S1 N2 47.55(15) . . ? C5 S1 I1 92.76(17) . . ? N1 S1 I1 108.42(12) . . ? N2 S1 I1 76.63(11) . . ? C5 S1 I2 93.96(18) . 1_565 ? N1 S1 I2 78.48(11) . 1_565 ? N2 S1 I2 108.90(11) . 1_565 ? I1 S1 I2 83.26(3) . 1_565 ? C5 S1 I3 160.07(17) . . ? N1 S1 I3 150.76(12) . . ? N2 S1 I3 147.87(12) . . ? I1 S1 I3 71.63(3) . . ? I2 S1 I3 72.45(3) 1_565 . ? C5 S1 I4 123.33(17) . 7_576 ? N1 S1 I4 120.34(12) . 7_576 ? N2 S1 I4 120.24(11) . 7_576 ? I1 S1 I4 125.79(4) . 7_576 ? I2 S1 I4 126.57(4) 1_565 7_576 ? I3 S1 I4 76.52(3) . 7_576 ? C5 N1 C6 112.6(5) . . ? C5 N1 S1 31.2(3) . . ? C6 N1 S1 143.8(4) . . ? C5 N1 H1A 123.7 . . ? C6 N1 H1A 123.7 . . ? S1 N1 H1A 92.5 . . ? C5 N2 C7 112.3(5) . . ? C5 N2 S1 31.2(3) . . ? C7 N2 S1 143.4(4) . . ? C5 N2 H2A 123.8 . . ? C7 N2 H2A 123.8 . . ? S1 N2 H2A 92.7 . . ? C2 C1 I1 124.05(18) . . ? C2 C1 I1 124.05(18) . 2 ? I1 C1 I1 111.9(4) . 2 ? C1 C2 I2 123.8(2) . 2 ? C1 C2 I2 123.8(2) . . ? I2 C2 I2 112.3(4) 2 . ? C4 C3 I4 124.0(4) . . ? C4 C3 I3 122.8(4) . . ? I4 C3 I3 113.2(3) . . ? C3 C4 I5 123.2(4) . . ? C3 C4 I6 121.8(4) . . ? I5 C4 I6 115.0(2) . . ? N1 C5 N2 109.9(5) . . ? N1 C5 S1 125.0(4) . . ? N2 C5 S1 125.0(4) . . ? N1 C6 C7 102.2(5) . . ? N1 C6 H6A 111.3 . . ? C7 C6 H6A 111.3 . . ? N1 C6 H6B 111.3 . . ? C7 C6 H6B 111.3 . . ? H6A C6 H6B 109.2 . . ? N2 C7 C6 102.8(5) . . ? N2 C7 H7A 111.2 . . ? C6 C7 H7A 111.2 . . ? N2 C7 H7B 111.2 . . ? C6 C7 H7B 111.2 . . ? H7A C7 H7B 109.1 . . ? 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 C1 I1 I2 C2 0.605(8) . . . . ? S1 I1 I2 C2 -174.25(3) . . . . ? I1 I1 I2 C2 1.145(12) 2 . . . ? I5 I1 I2 C2 -66.053(17) 2 . . . ? C1 I1 I2 S1 172.29(3) . . . 1_545 ? S1 I1 I2 S1 -2.57(3) . . . 1_545 ? I1 I1 I2 S1 172.83(3) 2 . . 1_545 ? I5 I1 I2 S1 105.63(4) 2 . . 1_545 ? C1 I1 I2 I2 1.140(12) . . . 2 ? S1 I1 I2 I2 -173.72(3) . . . 2 ? I1 I1 I2 I2 1.680(17) 2 . . 2 ? I5 I1 I2 I2 -65.52(2) 2 . . 2 ? I5 I3 I4 C3 -1.0(3) . . . . ? S1 I3 I4 C3 140.0(3) . . . . ? C3 I3 I4 I6 -1.7(3) . . . . ? I5 I3 I4 I6 -2.638(14) . . . . ? S1 I3 I4 I6 138.34(7) . . . . ? C3 I3 I4 S1 167.4(3) . . . 7_576 ? I5 I3 I4 S1 166.43(3) . . . 7_576 ? S1 I3 I4 S1 -52.60(9) . . . 7_576 ? C3 I3 I5 C4 0.9(3) . . . . ? I4 I3 I5 C4 1.58(19) . . . . ? S1 I3 I5 C4 -164.19(19) . . . . ? C3 I3 I5 I6 2.06(18) . . . . ? I4 I3 I5 I6 2.692(14) . . . . ? S1 I3 I5 I6 -163.08(3) . . . . ? C3 I3 I5 I1 -164.21(18) . . . 2 ? I4 I3 I5 I1 -163.570(15) . . . 2 ? S1 I3 I5 I1 30.66(3) . . . 2 ? I3 I5 I6 C4 -1.7(3) . . . . ? I1 I5 I6 C4 148.6(3) 2 . . . ? C4 I5 I6 I4 -0.9(3) . . . . ? I3 I5 I6 I4 -2.612(14) . . . . ? I1 I5 I6 I4 147.72(3) 2 . . . ? C3 I4 I6 C4 1.0(3) . . . . ? I3 I4 I6 C4 2.14(19) . . . . ? S1 I4 I6 C4 -158.23(19) 7_576 . . . ? C3 I4 I6 I5 1.60(18) . . . . ? I3 I4 I6 I5 2.698(14) . . . . ? S1 I4 I6 I5 -157.67(5) 7_576 . . . ? C1 I1 S1 C5 -58.0(8) . . . . ? I1 I1 S1 C5 -84.71(18) 2 . . . ? I2 I1 S1 C5 88.24(18) . . . . ? I5 I1 S1 C5 -36.21(18) 2 . . . ? C1 I1 S1 N1 -39.8(8) . . . . ? I1 I1 S1 N1 -66.49(13) 2 . . . ? I2 I1 S1 N1 106.46(12) . . . . ? I5 I1 S1 N1 -18.00(12) 2 . . . ? C1 I1 S1 N2 -75.7(8) . . . . ? I1 I1 S1 N2 -102.35(11) 2 . . . ? I2 I1 S1 N2 70.59(11) . . . . ? I5 I1 S1 N2 -53.86(11) 2 . . . ? C1 I1 S1 I2 35.6(8) . . . 1_565 ? I1 I1 S1 I2 8.96(5) 2 . . 1_565 ? I2 I1 S1 I2 -178.100(19) . . . 1_565 ? I5 I1 S1 I2 57.45(2) 2 . . 1_565 ? C1 I1 S1 I3 109.3(8) . . . . ? I1 I1 S1 I3 82.65(4) 2 . . . ? I2 I1 S1 I3 -104.40(3) . . . . ? I5 I1 S1 I3 131.15(2) 2 . . . ? C1 I1 S1 I4 166.5(7) . . . 7_576 ? I1 I1 S1 I4 139.82(4) 2 . . 7_576 ? I2 I1 S1 I4 -47.23(6) . . . 7_576 ? I5 I1 S1 I4 -171.68(5) 2 . . 7_576 ? C3 I3 S1 C5 -36.0(7) . . . . ? I4 I3 S1 C5 -138.4(5) . . . . ? I5 I3 S1 C5 0.5(6) . . . . ? C3 I3 S1 N1 19.2(5) . . . . ? I4 I3 S1 N1 -83.2(3) . . . . ? I5 I3 S1 N1 55.7(2) . . . . ? C3 I3 S1 N2 -85.0(5) . . . . ? I4 I3 S1 N2 172.5(2) . . . . ? I5 I3 S1 N2 -48.5(2) . . . . ? C3 I3 S1 I1 -75.9(4) . . . . ? I4 I3 S1 I1 -178.29(6) . . . . ? I5 I3 S1 I1 -39.35(3) . . . . ? C3 I3 S1 I2 12.7(4) . . . 1_565 ? I4 I3 S1 I2 -89.70(7) . . . 1_565 ? I5 I3 S1 I2 49.23(3) . . . 1_565 ? C3 I3 S1 I4 148.6(4) . . . 7_576 ? I4 I3 S1 I4 46.22(8) . . . 7_576 ? I5 I3 S1 I4 -174.852(18) . . . 7_576 ? N2 S1 N1 C5 -0.3(4) . . . . ? I1 S1 N1 C5 -50.9(5) . . . . ? I2 S1 N1 C5 -129.7(5) 1_565 . . . ? I3 S1 N1 C5 -136.0(5) . . . . ? I4 S1 N1 C5 104.5(5) 7_576 . . . ? C5 S1 N1 C6 -4.7(6) . . . . ? N2 S1 N1 C6 -5.0(6) . . . . ? I1 S1 N1 C6 -55.6(7) . . . . ? I2 S1 N1 C6 -134.4(7) 1_565 . . . ? I3 S1 N1 C6 -140.7(6) . . . . ? I4 S1 N1 C6 99.8(7) 7_576 . . . ? N1 S1 N2 C5 0.3(4) . . . . ? I1 S1 N2 C5 131.4(5) . . . . ? I2 S1 N2 C5 53.5(5) 1_565 . . . ? I3 S1 N2 C5 140.4(4) . . . . ? I4 S1 N2 C5 -104.7(5) 7_576 . . . ? C5 S1 N2 C7 4.8(6) . . . . ? N1 S1 N2 C7 5.1(6) . . . . ? I1 S1 N2 C7 136.2(7) . . . . ? I2 S1 N2 C7 58.3(7) 1_565 . . . ? I3 S1 N2 C7 145.2(6) . . . . ? I4 S1 N2 C7 -99.9(6) 7_576 . . . ? S1 I1 C1 C2 148.4(7) . . . . ? I1 I1 C1 C2 180.0 2 . . . ? I2 I1 C1 C2 -0.965(10) . . . . ? I5 I1 C1 C2 126.789(10) 2 . . . ? S1 I1 C1 I1 -31.6(7) . . . 2 ? I2 I1 C1 I1 179.035(10) . . . 2 ? I5 I1 C1 I1 -53.211(10) 2 . . 2 ? I1 C1 C2 I2 -178.320(17) . . . 2 ? I1 C1 C2 I2 1.680(17) 2 . . 2 ? I1 C1 C2 I2 1.680(17) . . . . ? I1 C1 C2 I2 -178.320(17) 2 . . . ? S1 I2 C2 C1 -147.0(6) 1_545 . . . ? I2 I2 C2 C1 180.0 2 . . . ? I1 I2 C2 C1 -0.962(10) . . . . ? S1 I2 C2 I2 33.0(6) 1_545 . . 2 ? I1 I2 C2 I2 179.038(10) . . . 2 ? I3 I4 C3 C4 -179.7(7) . . . . ? I6 I4 C3 C4 -1.7(4) . . . . ? S1 I4 C3 C4 157.7(4) 7_576 . . . ? I6 I4 C3 I3 178.0(3) . . . . ? S1 I4 C3 I3 -22.7(5) 7_576 . . . ? I4 I3 C3 C4 179.7(7) . . . . ? I5 I3 C3 C4 -1.5(4) . . . . ? S1 I3 C3 C4 41.4(8) . . . . ? I5 I3 C3 I4 178.8(3) . . . . ? S1 I3 C3 I4 -138.3(3) . . . . ? I4 C3 C4 I5 -177.8(3) . . . . ? I3 C3 C4 I5 2.6(7) . . . . ? I4 C3 C4 I6 2.8(7) . . . . ? I3 C3 C4 I6 -176.8(3) . . . . ? I6 I5 C4 C3 -179.4(7) . . . . ? I3 I5 C4 C3 -1.5(4) . . . . ? I1 I5 C4 C3 55.0(9) 2 . . . ? I3 I5 C4 I6 177.9(3) . . . . ? I1 I5 C4 I6 -125.6(4) 2 . . . ? I5 I6 C4 C3 179.4(7) . . . . ? I4 I6 C4 C3 -1.6(4) . . . . ? I4 I6 C4 I5 179.0(3) . . . . ? C6 N1 C5 N2 -3.5(6) . . . . ? S1 N1 C5 N2 179.5(7) . . . . ? C6 N1 C5 S1 177.0(4) . . . . ? C7 N2 C5 N1 3.6(6) . . . . ? S1 N2 C5 N1 -179.5(7) . . . . ? C7 N2 C5 S1 -176.9(4) . . . . ? N2 S1 C5 N1 179.5(8) . . . . ? I1 S1 C5 N1 132.5(4) . . . . ? I2 S1 C5 N1 49.1(5) 1_565 . . . ? I3 S1 C5 N1 95.0(7) . . . . ? I4 S1 C5 N1 -90.4(5) 7_576 . . . ? N1 S1 C5 N2 -179.5(8) . . . . ? I1 S1 C5 N2 -46.9(5) . . . . ? I2 S1 C5 N2 -130.4(4) 1_565 . . . ? I3 S1 C5 N2 -84.5(7) . . . . ? I4 S1 C5 N2 90.2(5) 7_576 . . . ? C5 N1 C6 C7 2.0(7) . . . . ? S1 N1 C6 C7 4.7(9) . . . . ? C5 N2 C7 C6 -2.1(7) . . . . ? S1 N2 C7 C6 -4.8(9) . . . . ? N1 C6 C7 N2 0.1(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A S1 0.86 2.57 3.380(5) 157.1 4 N2 H2A S1 0.86 2.60 3.371(5) 149.6 4_545 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.034 _refine_diff_density_min -1.497 _refine_diff_density_rms 0.185