# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Nick Hadjiliadis' _publ_contact_author_email NHADJIS@UOI.GR _publ_section_title ; Structural motifs of diiodine complexes with amides and thioamides. ; loop_ _publ_author_name 'Nick Hadjiliadis' 'Ghada Corban' 'Sotiris Hadjikakou' 'George E Kostakis' ; N.Kourkoumelis ; 'Maciej Kubicki' 'Ioanna-Efpraxia Parigoridi' 'Vassilis Psycharis' 'Catherine Raptopoulou' data_1 _database_code_depnum_ccdc_archive 'CCDC 679938' _database_code_CSD 605961 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Di-2-pyrymidonium dichloride-di-iodide ; _chemical_name_common 'Di-2-pyrymidonium dichloride-di-iodide' _chemical_melting_point ? _chemical_formula_moiety 'C4 H5 N2 O, 0.5(I2), Cl' _chemical_formula_sum 'C4 H5 Cl I N2 O' _chemical_formula_weight 259.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.849(2) _cell_length_b 10.448(2) _cell_length_c 9.570(3) _cell_angle_alpha 90.00 _cell_angle_beta 102.55(1) _cell_angle_gamma 90.00 _cell_volume 766.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 294(1) _cell_measurement_reflns_used 2251 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 2.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 4.454 _exptl_absorpt_correction_T_min 0.39 _exptl_absorpt_correction_T_max 0.64 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) (compiled Mar 23 2006,23:39:28) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'KUMA KM4CCD' _diffrn_measurement_method \w-scan _diffrn_detector_area_resol_mean 8.1929 _diffrn_reflns_number 5992 _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.25 _reflns_number_total 1386 _reflns_number_gt 1014 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD Version 1.171.29.9 Oxford Diffraction, 2006) ; _computing_cell_refinement ; CrysAlis RED Version 1.171.29.9 Oxford Diffraction, 2006) ; _computing_data_reduction ; CrysAlis RED Version 1.171.29.9 Oxford Diffraction, 2006) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Siemens, 1989)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1386 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 N1 N 0.5367(6) 0.1850(5) 0.3248(5) 0.0406(13) Uani 1 1 d . . . H1 H 0.4708 0.1225 0.2878 0.049 Uiso 1 1 calc R . . C2 C 0.6781(9) 0.2162(6) 0.2657(7) 0.0415(16) Uani 1 1 d . . . O2 O 0.7141(8) 0.1597(5) 0.1655(6) 0.0682(16) Uani 1 1 d . . . N3 N 0.7730(7) 0.3169(5) 0.3340(6) 0.0412(13) Uani 1 1 d . . . H3 H 0.8638 0.3410 0.3043 0.049 Uiso 1 1 calc R . . C4 C 0.7332(9) 0.3798(7) 0.4435(7) 0.0449(17) Uani 1 1 d . . . H4 H 0.8022 0.4484 0.4837 0.054 Uiso 1 1 calc R . . C5 C 0.5954(10) 0.3459(7) 0.4967(7) 0.0468(18) Uani 1 1 d . . . H5 H 0.5680 0.3896 0.5736 0.056 Uiso 1 1 calc R . . C6 C 0.4977(9) 0.2464(7) 0.4352(8) 0.0436(17) Uani 1 1 d . . . H6 H 0.4019 0.2205 0.4706 0.052 Uiso 1 1 calc R . . I1 I 0.61675(5) 0.52274(4) 0.91617(5) 0.0442(2) Uani 1 1 d . . . Cl1 Cl 0.8810(2) 0.58455(17) 0.73236(18) 0.0440(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.037(3) 0.037(3) 0.045(3) -0.001(3) 0.003(3) -0.006(2) C2 0.043(4) 0.035(4) 0.048(4) 0.004(3) 0.013(3) 0.005(3) O2 0.088(4) 0.064(4) 0.062(3) -0.019(3) 0.035(3) -0.005(3) N3 0.035(3) 0.045(3) 0.046(3) 0.000(3) 0.013(3) -0.006(3) C4 0.056(5) 0.037(4) 0.039(4) -0.002(3) 0.003(3) -0.007(3) C5 0.068(5) 0.036(4) 0.042(4) -0.002(3) 0.024(4) 0.000(4) C6 0.045(4) 0.047(4) 0.042(4) 0.009(3) 0.017(3) 0.010(3) I1 0.0393(3) 0.0485(3) 0.0449(3) -0.0012(2) 0.0095(2) 0.0020(2) Cl1 0.0439(10) 0.0416(10) 0.0510(10) 0.0014(8) 0.0201(8) -0.0001(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.327(8) . ? N1 C2 1.389(8) . ? N1 H1 0.8600 . ? C2 O2 1.210(8) . ? C2 N3 1.371(8) . ? N3 C4 1.330(8) . ? N3 H3 0.8600 . ? C4 C5 1.339(9) . ? C4 H4 0.9300 . ? C5 C6 1.348(10) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? I1 I1 2.7270(11) 3_667 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C2 123.6(6) . . ? C6 N1 H1 118.2 . . ? C2 N1 H1 118.2 . . ? O2 C2 N3 123.8(6) . . ? O2 C2 N1 123.6(6) . . ? N3 C2 N1 112.6(6) . . ? C4 N3 C2 124.0(5) . . ? C4 N3 H3 118.0 . . ? C2 N3 H3 118.0 . . ? N3 C4 C5 121.1(6) . . ? N3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 117.9(6) . . ? C4 C5 H5 121.1 . . ? C6 C5 H5 121.1 . . ? N1 C6 C5 120.8(6) . . ? N1 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? 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 H1 Cl1 0.86 2.30 3.121(6) 159.3 4_565 N3 H3 Cl1 0.86 2.25 3.096(5) 169.6 3_766 C4 H4 Cl1 0.93 2.73 3.489(7) 139.9 . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.103 _refine_diff_density_min -0.567 _refine_diff_density_rms 0.157 data_sotirtzd _database_code_depnum_ccdc_archive 'CCDC 682861' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H10 I6 N2 S4' _chemical_formula_weight 999.80 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 15.8350(18) _cell_length_b 9.520(2) _cell_length_c 28.461(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.436(7) _cell_angle_gamma 90.00 _cell_volume 4189.8(12) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parall _exptl_crystal_colour red _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3536 _exptl_absorpt_coefficient_mu 9.284 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.29 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-AXIS SPIDER Image Plate' _diffrn_measurement_method '\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28608 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4122 _reflns_number_gt 4018 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear, Rigaku MSC, 2005' _computing_cell_refinement 'CrystalClear, Rigaku MSC, 2005' _computing_data_reduction 'CrystalClear, Rigaku MSC, 2005' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0000P)^2^+29.9932P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.000446(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4122 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0526 _refine_ls_wR_factor_gt 0.0520 _refine_ls_goodness_of_fit_ref 1.293 _refine_ls_restrained_S_all 1.293 _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 0.11510(2) -0.00339(4) 0.206725(11) 0.02761(9) Uani 1 1 d . . . I2 I 0.14100(2) -0.30356(4) 0.227363(12) 0.03505(10) Uani 1 1 d . . . S1 S 0.09747(8) 0.26966(14) 0.19478(5) 0.0302(3) Uani 1 1 d . . . S2 S -0.05599(9) 0.45652(14) 0.18071(5) 0.0342(3) Uani 1 1 d . . . N1 N -0.0710(2) 0.1835(5) 0.17887(14) 0.0252(9) Uani 1 1 d . . . C1 C -0.0120(3) 0.2901(5) 0.18468(16) 0.0241(10) Uani 1 1 d . . . C2 C -0.1617(4) 0.2353(6) 0.1643(2) 0.0331(12) Uani 1 1 d . . . C3 C -0.1636(4) 0.3891(6) 0.1787(2) 0.0363(12) Uani 1 1 d . . . I3 I -0.43329(2) 0.62820(3) 0.054158(10) 0.02455(9) Uani 1 1 d . . . I4 I -0.28926(2) 0.43621(3) 0.046172(12) 0.02935(9) Uani 1 1 d . . . S3 S -0.56228(8) 0.79632(13) 0.05267(5) 0.0286(3) Uani 1 1 d . . . S4 S -0.56925(8) 1.10703(13) 0.05238(5) 0.0290(3) Uani 1 1 d . . . N2 N -0.4290(3) 0.9737(5) 0.08434(16) 0.0267(9) Uani 1 1 d . . . C5 C -0.5114(3) 0.9531(5) 0.06549(15) 0.0216(9) Uani 1 1 d . . . C6 C -0.4782(3) 1.2097(6) 0.0845(2) 0.0302(11) Uani 1 1 d . . . C7 C -0.3986(3) 1.1204(5) 0.0864(2) 0.0283(11) Uani 1 1 d . . . I6 I -0.19728(2) 0.92998(4) 0.060845(12) 0.03243(9) Uani 1 1 d . . . I5 I -0.17798(3) 0.81842(4) 0.152687(13) 0.03844(10) Uani 1 1 d . . . HN2 H -0.398(4) 0.909(7) 0.093(2) 0.038(18) Uiso 1 1 d . . . H2A H -0.194(5) 0.188(9) 0.182(3) 0.08(3) Uiso 1 1 d . . . H2B H -0.184(4) 0.221(7) 0.127(2) 0.047(17) Uiso 1 1 d . . . H3A H -0.198(5) 0.441(8) 0.153(3) 0.08(2) Uiso 1 1 d . . . H3B H -0.176(4) 0.407(6) 0.212(2) 0.043(17) Uiso 1 1 d . . . H6A H -0.486(3) 1.230(5) 0.1177(18) 0.017(12) Uiso 1 1 d . . . H6B H -0.475(5) 1.288(8) 0.074(3) 0.06(2) Uiso 1 1 d . . . H7A H -0.355(3) 1.128(5) 0.1168(19) 0.022(13) Uiso 1 1 d . . . H7B H -0.373(4) 1.132(6) 0.066(2) 0.029(16) Uiso 1 1 d . . . HN1 H -0.0602 0.1088 0.1780 0.021 Uiso 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 0.02759(17) 0.02811(18) 0.02705(16) 0.00119(12) 0.00570(13) 0.00376(13) I2 0.0441(2) 0.02603(18) 0.03653(18) 0.00500(14) 0.01201(15) 0.00340(15) S1 0.0278(6) 0.0248(6) 0.0376(7) 0.0009(5) 0.0060(5) 0.0007(5) S2 0.0375(7) 0.0252(7) 0.0406(7) -0.0023(5) 0.0098(6) 0.0003(6) N1 0.0148(18) 0.034(2) 0.026(2) 0.0080(17) 0.0031(15) -0.0006(17) C1 0.033(3) 0.022(2) 0.018(2) -0.0003(18) 0.0059(18) 0.001(2) C2 0.026(3) 0.026(3) 0.046(3) -0.003(2) 0.006(2) 0.000(2) C3 0.040(3) 0.036(3) 0.031(3) -0.003(2) 0.004(2) 0.010(3) I3 0.03392(17) 0.01493(15) 0.02466(15) -0.00159(11) 0.00599(12) -0.00420(13) I4 0.02819(17) 0.02267(17) 0.03581(17) 0.00524(13) 0.00386(13) 0.00139(13) S3 0.0279(6) 0.0177(6) 0.0416(7) -0.0066(5) 0.0105(5) -0.0057(5) S4 0.0256(6) 0.0181(6) 0.0411(7) 0.0025(5) 0.0021(5) 0.0001(5) N2 0.025(2) 0.016(2) 0.039(2) -0.0004(17) 0.0044(18) 0.0015(18) C5 0.027(2) 0.020(2) 0.019(2) -0.0011(17) 0.0073(18) -0.001(2) C6 0.029(3) 0.015(2) 0.046(3) -0.002(2) 0.006(2) -0.002(2) C7 0.027(3) 0.020(3) 0.039(3) -0.003(2) 0.010(2) -0.008(2) I6 0.03020(18) 0.02621(18) 0.04210(19) -0.00479(14) 0.01047(14) 0.00465(14) I5 0.0482(2) 0.0299(2) 0.0413(2) -0.00434(15) 0.01854(16) -0.00029(17) _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 S1 2.6287(14) . ? I1 I2 2.9285(8) . ? S1 C1 1.706(5) . ? S2 C1 1.725(5) . ? S2 C3 1.810(6) . ? N1 C1 1.365(6) . ? N1 C2 1.491(6) . ? N1 HN1 0.7328 . ? C2 C3 1.523(8) . ? C2 H2A 0.91(8) . ? C2 H2B 1.05(6) . ? C3 H3A 0.95(8) . ? C3 H3B 1.02(6) . ? I3 S3 2.5882(13) . ? I3 I4 2.9694(6) . ? S3 C5 1.698(5) . ? S4 C5 1.726(5) . ? S4 C6 1.817(5) . ? N2 C5 1.313(6) . ? N2 C7 1.475(6) . ? N2 HN2 0.79(6) . ? C6 C7 1.511(7) . ? C6 H6A 1.00(5) . ? C6 H6B 0.81(8) . ? C7 H7A 0.98(5) . ? C7 H7B 0.77(6) . ? I6 I5 2.7767(7) . ? 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 S1 I1 I2 175.81(3) . . ? C1 S1 I1 102.14(17) . . ? C1 S2 C3 92.3(3) . . ? C1 N1 C2 112.4(4) . . ? C1 N1 HN1 124.5 . . ? C2 N1 HN1 122.0 . . ? N1 C1 S1 125.4(4) . . ? N1 C1 S2 114.8(4) . . ? S1 C1 S2 119.8(3) . . ? N1 C2 C3 108.4(4) . . ? N1 C2 H2A 108(5) . . ? C3 C2 H2A 107(5) . . ? N1 C2 H2B 110(3) . . ? C3 C2 H2B 112(4) . . ? H2A C2 H2B 112(6) . . ? C2 C3 S2 106.1(4) . . ? C2 C3 H3A 110(5) . . ? S2 C3 H3A 103(5) . . ? C2 C3 H3B 115(4) . . ? S2 C3 H3B 107(3) . . ? H3A C3 H3B 115(6) . . ? S3 I3 I4 174.80(3) . . ? C5 S3 I3 101.74(17) . . ? C5 S4 C6 91.2(2) . . ? C5 N2 C7 116.5(4) . . ? C5 N2 HN2 120(5) . . ? C7 N2 HN2 123(5) . . ? N2 C5 S3 127.1(4) . . ? N2 C5 S4 113.3(4) . . ? S3 C5 S4 119.6(3) . . ? C7 C6 S4 106.3(4) . . ? C7 C6 H6A 110(3) . . ? S4 C6 H6A 109(3) . . ? C7 C6 H6B 114(5) . . ? S4 C6 H6B 115(5) . . ? H6A C6 H6B 101(6) . . ? N2 C7 C6 105.5(4) . . ? N2 C7 H7A 105(3) . . ? C6 C7 H7A 114(3) . . ? N2 C7 H7B 109(4) . . ? C6 C7 H7B 117(4) . . ? H7A C7 H7B 105(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.736 _refine_diff_density_min -0.733 _refine_diff_density_rms 0.150