# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Francesco Demartin' _publ_contact_author_email francesco.demartin@unimi.it loop_ _publ_author_name 'M.C. Aragoni' 'M. Arca' 'C. Caltagirone' 'C. Castellano' 'F. Demartin' ; A.Garau ; 'F. Isaia' 'V. Lippolis' 'R. Montis' 'A. Pintus' data_HL1I3 _database_code_depnum_ccdc_archive 'CCDC 865996' #TrackingRef 'web_deposit_cif_file_0_FrancescoDemartin_1328621263.HL1I3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 I3 N4 S' _chemical_formula_weight 621.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 16.011(3) _cell_length_b 5.9870(12) _cell_length_c 19.649(4) _cell_angle_alpha 90.00 _cell_angle_beta 111.46(3) _cell_angle_gamma 90.00 _cell_volume 1752.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 26.64 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 5.464 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.782 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'SMART CCD diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13774 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.08 _reflns_number_total 3407 _reflns_number_gt 2365 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0273P)^2^+3.7700P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3407 _refine_ls_number_parameters 184 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0700 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.5000 0.5000 0.0000 0.05348(16) Uani 1 2 d S . . I2 I 0.47109(3) 0.32727(9) -0.14648(3) 0.06693(15) Uani 1 1 d . . . I3 I 1.0000 0.0000 0.0000 0.05448(16) Uani 1 2 d S . . I4 I 1.07536(3) 0.33669(8) 0.11450(3) 0.07203(16) Uani 1 1 d . . . S S 0.66456(12) 0.0009(3) 0.04890(9) 0.0586(4) Uani 1 1 d . . . N1 N 0.8200(3) 0.7724(8) 0.2285(2) 0.0471(12) Uani 1 1 d . . . HN1 H 0.8059 0.8106 0.2651 0.057 Uiso 1 1 calc R . . N2 N 0.7062(3) 0.1813(8) 0.1102(2) 0.0396(10) Uani 1 1 d . . . N3 N 0.7618(3) 0.2898(7) 0.0204(2) 0.0429(11) Uani 1 1 d . . . N4 N 0.7360(3) 0.0616(8) -0.1877(3) 0.0449(11) Uani 1 1 d . . . C1 C 0.7836(4) 0.5937(9) 0.1895(3) 0.0445(14) Uani 1 1 d . . . H1 H 0.7429 0.5110 0.2029 0.053 Uiso 1 1 calc R . . C2 C 0.8786(4) 0.8930(11) 0.2105(3) 0.0554(16) Uani 1 1 d . . . H2 H 0.9040 1.0191 0.2379 0.066 Uiso 1 1 calc R . . C3 C 0.9029(4) 0.8358(12) 0.1521(4) 0.0647(18) Uani 1 1 d . . . H3 H 0.9441 0.9217 0.1403 0.078 Uiso 1 1 calc R . . C4 C 0.8644(4) 0.6474(11) 0.1114(3) 0.0557(16) Uani 1 1 d . . . H4 H 0.8797 0.6049 0.0719 0.067 Uiso 1 1 calc R . . C5 C 0.8030(3) 0.5235(9) 0.1302(3) 0.0416(13) Uani 1 1 d . . . C6 C 0.7571(3) 0.3294(9) 0.0872(3) 0.0400(12) Uani 1 1 d . . . C7 C 0.7138(4) 0.1114(9) -0.0077(3) 0.0413(13) Uani 1 1 d . . . C8 C 0.7013(4) 0.0252(9) -0.0811(3) 0.0425(13) Uani 1 1 d . . . C9 C 0.6464(4) -0.1544(11) -0.1122(3) 0.0596(16) Uani 1 1 d . . . H9 H 0.6165 -0.2289 -0.0863 0.072 Uiso 1 1 calc R . . C10 C 0.6361(5) -0.2232(11) -0.1824(4) 0.0637(18) Uani 1 1 d . . . H10 H 0.5997 -0.3443 -0.2041 0.076 Uiso 1 1 calc R . . C11 C 0.6805(4) -0.1090(10) -0.2188(3) 0.0540(16) Uani 1 1 d . . . H11 H 0.6723 -0.1502 -0.2664 0.065 Uiso 1 1 calc R . . C12 C 0.7464(4) 0.1277(9) -0.1209(3) 0.0418(13) Uani 1 1 d . . . H12 H 0.7850 0.2459 -0.1001 0.050 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 0.0428(3) 0.0543(3) 0.0594(4) 0.0071(3) 0.0141(3) -0.0033(3) I2 0.0600(3) 0.0788(3) 0.0600(3) 0.0001(2) 0.0197(2) -0.0052(2) I3 0.0549(3) 0.0540(3) 0.0597(4) 0.0156(3) 0.0271(3) 0.0091(3) I4 0.0747(3) 0.0576(3) 0.0779(3) 0.0047(2) 0.0209(3) 0.0084(2) S 0.0737(11) 0.0562(9) 0.0537(10) 0.0036(8) 0.0324(8) -0.0052(9) N1 0.060(3) 0.055(3) 0.034(3) -0.001(2) 0.026(2) 0.009(2) N2 0.050(3) 0.054(3) 0.024(2) 0.014(2) 0.025(2) 0.012(2) N3 0.045(3) 0.046(3) 0.042(3) 0.001(2) 0.021(2) -0.003(2) N4 0.053(3) 0.049(3) 0.039(3) 0.005(2) 0.025(2) 0.010(2) C1 0.050(3) 0.045(3) 0.042(3) 0.009(3) 0.021(3) 0.007(3) C2 0.054(4) 0.064(4) 0.050(4) -0.011(3) 0.020(3) -0.004(3) C3 0.052(4) 0.082(5) 0.069(5) -0.011(4) 0.033(3) -0.016(4) C4 0.048(3) 0.073(4) 0.054(4) -0.011(3) 0.028(3) -0.004(3) C5 0.039(3) 0.050(3) 0.038(3) 0.005(3) 0.018(2) 0.011(3) C6 0.042(3) 0.047(3) 0.035(3) 0.006(3) 0.019(2) 0.012(3) C7 0.046(3) 0.047(3) 0.034(3) 0.007(2) 0.018(3) 0.009(3) C8 0.049(3) 0.043(3) 0.043(3) 0.000(3) 0.026(3) -0.003(3) C9 0.072(4) 0.066(4) 0.052(4) -0.008(3) 0.036(3) -0.016(4) C10 0.070(4) 0.068(4) 0.059(4) -0.015(3) 0.030(4) -0.020(3) C11 0.070(4) 0.060(4) 0.038(3) -0.004(3) 0.028(3) 0.005(3) C12 0.042(3) 0.045(3) 0.042(3) 0.007(3) 0.019(3) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 I2 2.9313(7) . ? I1 I2 2.9313(7) 3_665 ? I3 I4 2.9316(8) . ? I3 I4 2.9316(8) 3_755 ? S N2 1.573(5) . ? S C7 1.713(5) . ? N1 C1 1.320(7) . ? N1 C2 1.331(8) . ? N2 C6 1.387(7) . ? N3 C7 1.314(7) . ? N3 C6 1.363(7) . ? N4 C12 1.321(7) . ? N4 C11 1.344(8) . ? C1 C5 1.377(7) . ? C2 C3 1.383(9) . ? C3 C4 1.390(9) . ? C4 C5 1.387(8) . ? C5 C6 1.466(8) . ? C7 C8 1.476(8) . ? C8 C9 1.381(8) . ? C8 C12 1.387(7) . ? C9 C10 1.391(9) . ? C10 C11 1.362(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I2 I1 I2 180.00(2) . 3_665 ? I4 I3 I4 180.000(17) . 3_755 ? N2 S C7 93.7(3) . . ? C1 N1 C2 119.3(5) . . ? C6 N2 S 108.9(3) . . ? C7 N3 C6 108.4(4) . . ? C12 N4 C11 120.1(5) . . ? N1 C1 C5 123.4(5) . . ? N1 C2 C3 121.7(6) . . ? C2 C3 C4 118.6(6) . . ? C5 C4 C3 119.3(6) . . ? C1 C5 C4 117.6(5) . . ? C1 C5 C6 120.7(5) . . ? C4 C5 C6 121.6(5) . . ? N3 C6 N2 116.7(5) . . ? N3 C6 C5 120.1(5) . . ? N2 C6 C5 123.3(5) . . ? N3 C7 C8 122.9(5) . . ? N3 C7 S 112.3(4) . . ? C8 C7 S 124.7(4) . . ? C9 C8 C12 118.3(5) . . ? C9 C8 C7 122.7(5) . . ? C12 C8 C7 119.0(5) . . ? C8 C9 C10 119.6(6) . . ? C11 C10 C9 118.5(6) . . ? N4 C11 C10 121.9(6) . . ? N4 C12 C8 121.6(5) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 26.08 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.806 _refine_diff_density_min -0.601 _refine_diff_density_rms 0.107 # Attachment 'web_deposit_cif_file_1_FrancescoDemartin_1328621263.HL1I5.cif' data_HL1I5 _database_code_depnum_ccdc_archive 'CCDC 865997' #TrackingRef 'web_deposit_cif_file_1_FrancescoDemartin_1328621263.HL1I5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 I5 N4 S' _chemical_formula_weight 875.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' 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' _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 15.9100(10) _cell_length_b 8.3920(10) _cell_length_c 16.0900(10) _cell_angle_alpha 90.00 _cell_angle_beta 101.140(10) _cell_angle_gamma 90.00 _cell_volume 2107.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6031 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 24.82 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.760 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 7.478 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.791 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'SMART CCD diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21947 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.2600 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.55 _reflns_number_total 4854 _reflns_number_gt 2220 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0153P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4854 _refine_ls_number_parameters 203 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0549 _refine_ls_wR_factor_gt 0.0532 _refine_ls_goodness_of_fit_ref 0.624 _refine_ls_restrained_S_all 0.624 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.009 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 0.71417(3) 0.48583(7) 1.16500(3) 0.08419(16) Uani 1 1 d . . . I2 I 0.73340(2) 0.47833(5) 0.99170(2) 0.05615(11) Uani 1 1 d . . . I3 I 0.74337(3) 0.44125(7) 0.81042(3) 0.08253(16) Uani 1 1 d . . . I4 I 0.56600(3) 0.62817(5) 0.74162(3) 0.06952(14) Uani 1 1 d . . . I5 I 0.41236(3) 0.78381(6) 0.68691(3) 0.08867(17) Uani 1 1 d . . . S S 0.22055(17) 0.5630(3) 0.41492(12) 0.0784(11) Uani 0.711(10) 1 d P . . S' S 0.3028(3) 0.4750(5) 0.4316(2) 0.092(2) Uani 0.307(11) 1 d P . . N1 N 0.4677(3) 0.2201(5) 0.6923(3) 0.0499(12) Uani 1 1 d . . . HN1 H 0.4701 0.1970 0.7448 0.060 Uiso 1 1 calc R . . N2 N 0.3028(3) 0.4750(5) 0.4316(2) 0.092(2) Uani 0.703(16) 1 d P . . N2' N 0.22055(17) 0.5630(3) 0.41492(12) 0.0784(11) Uani 0.299(16) 1 d P . . N3 N 0.2559(3) 0.4724(5) 0.5642(3) 0.0434(11) Uani 1 1 d . . . N4 N 0.0396(3) 0.6680(6) 0.6432(3) 0.0544(13) Uani 1 1 d . . . C1 C 0.4016(3) 0.2995(7) 0.6516(3) 0.0486(14) Uani 1 1 d . . . H1 H 0.3582 0.3280 0.6800 0.058 Uiso 1 1 calc R . . C2 C 0.5313(4) 0.1740(8) 0.6546(4) 0.0655(18) Uani 1 1 d . . . H2 H 0.5771 0.1156 0.6843 0.079 Uiso 1 1 calc R . . C3 C 0.5281(4) 0.2142(8) 0.5717(4) 0.0721(19) Uani 1 1 d . . . H3 H 0.5728 0.1854 0.5451 0.087 Uiso 1 1 calc R . . C4 C 0.4596(4) 0.2962(8) 0.5276(3) 0.0589(16) Uani 1 1 d . . . H4 H 0.4569 0.3208 0.4708 0.071 Uiso 1 1 calc R . . C5 C 0.3945(3) 0.3422(6) 0.5678(3) 0.0430(13) Uani 1 1 d . . . C6 C 0.3188(4) 0.4311(6) 0.5238(3) 0.0460(14) Uani 1 1 d . . . C7 C 0.1961(4) 0.5472(6) 0.5104(3) 0.0451(14) Uani 1 1 d . . . C8 C 0.1183(3) 0.6133(6) 0.5338(3) 0.0427(13) Uani 1 1 d . . . C9 C 0.0561(4) 0.6926(7) 0.4768(4) 0.0582(16) Uani 1 1 d . . . H9 H 0.0613 0.7014 0.4204 0.070 Uiso 1 1 calc R . . C10 C -0.0129(4) 0.7582(8) 0.5030(4) 0.0720(19) Uani 1 1 d . . . H10 H -0.0554 0.8101 0.4647 0.086 Uiso 1 1 calc R . . C11 C -0.0184(4) 0.7459(7) 0.5872(4) 0.0647(17) Uani 1 1 d . . . H11 H -0.0643 0.7938 0.6055 0.078 Uiso 1 1 calc R . . C12 C 0.1054(4) 0.6053(7) 0.6179(3) 0.0499(14) Uani 1 1 d . . . H12 H 0.1461 0.5524 0.6576 0.060 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 0.0822(3) 0.1153(4) 0.0533(2) -0.0050(3) 0.0086(2) 0.0220(3) I2 0.0486(2) 0.0522(2) 0.0662(2) 0.0045(2) 0.00749(18) 0.0064(2) I3 0.0823(3) 0.1107(4) 0.0595(3) 0.0051(3) 0.0261(2) 0.0103(3) I4 0.0843(3) 0.0719(3) 0.0576(2) -0.0131(2) 0.0268(2) -0.0198(3) I5 0.0906(4) 0.0683(3) 0.1059(4) -0.0007(3) 0.0161(3) -0.0118(3) S 0.107(2) 0.0873(19) 0.0435(13) 0.0083(11) 0.0209(12) 0.0256(15) S' 0.129(4) 0.087(3) 0.078(3) -0.002(2) 0.063(2) 0.002(3) N1 0.050(3) 0.060(3) 0.040(3) -0.001(2) 0.009(2) -0.005(3) N2 0.129(4) 0.087(3) 0.078(3) -0.002(2) 0.063(2) 0.002(3) N2' 0.107(2) 0.0873(19) 0.0435(13) 0.0083(11) 0.0209(12) 0.0256(15) N3 0.047(3) 0.042(3) 0.043(2) -0.002(2) 0.013(2) -0.006(2) N4 0.045(3) 0.068(3) 0.049(3) -0.004(3) 0.006(2) 0.006(3) C1 0.039(3) 0.056(4) 0.055(4) -0.006(3) 0.018(3) -0.009(3) C2 0.054(4) 0.075(5) 0.073(4) 0.007(4) 0.028(4) 0.002(3) C3 0.073(5) 0.092(5) 0.062(4) -0.002(4) 0.038(4) 0.002(4) C4 0.068(4) 0.073(4) 0.039(3) -0.002(3) 0.018(3) 0.005(4) C5 0.051(3) 0.041(3) 0.042(3) -0.012(3) 0.023(3) -0.008(3) C6 0.061(4) 0.039(3) 0.039(3) -0.007(3) 0.014(3) -0.006(3) C7 0.056(4) 0.040(3) 0.042(3) -0.008(3) 0.017(3) -0.007(3) C8 0.052(3) 0.035(3) 0.040(3) -0.003(3) 0.005(3) -0.006(3) C9 0.077(5) 0.054(4) 0.044(3) 0.000(3) 0.014(3) -0.003(4) C10 0.062(5) 0.086(5) 0.067(4) 0.014(4) 0.010(4) 0.019(4) C11 0.059(4) 0.062(4) 0.075(5) -0.008(4) 0.020(4) 0.001(4) C12 0.050(4) 0.058(4) 0.039(3) 0.000(3) 0.002(3) 0.004(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 I2 2.8639(6) . ? I2 I3 2.9679(6) . ? I4 I5 2.7613(7) . ? S S' 1.482(4) . ? S C7 1.662(5) . ? S' C6 1.501(6) . ? N1 C1 1.308(6) . ? N1 C2 1.334(6) . ? N3 C7 1.315(6) . ? N3 C6 1.340(6) . ? N4 C12 1.305(6) . ? N4 C11 1.330(7) . ? C1 C5 1.379(7) . ? C2 C3 1.367(8) . ? C3 C4 1.366(8) . ? C4 C5 1.378(7) . ? C5 C6 1.477(7) . ? C7 C8 1.470(7) . ? C8 C9 1.384(7) . ? C8 C12 1.407(7) . ? C9 C10 1.366(8) . ? C10 C11 1.378(8) . ? 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 I1 I2 I3 174.38(2) . . ? S' S C7 98.6(3) . . ? S S' C6 106.0(3) . . ? C1 N1 C2 121.9(5) . . ? C7 N3 C6 108.5(4) . . ? C12 N4 C11 118.7(5) . . ? N1 C1 C5 121.8(5) . . ? N1 C2 C3 118.9(6) . . ? C4 C3 C2 120.5(6) . . ? C3 C4 C5 119.6(5) . . ? C4 C5 C1 117.4(5) . . ? C4 C5 C6 122.3(5) . . ? C1 C5 C6 120.4(5) . . ? N3 C6 C5 120.9(4) . . ? N3 C6 S' 114.6(5) . . ? C5 C6 S' 124.4(4) . . ? N3 C7 C8 123.3(4) . . ? N3 C7 S 112.2(4) . . ? C8 C7 S 124.5(4) . . ? C9 C8 C12 116.2(5) . . ? C9 C8 C7 122.7(5) . . ? C12 C8 C7 121.0(5) . . ? C10 C9 C8 120.2(5) . . ? C9 C10 C11 118.8(6) . . ? N4 C11 C10 122.4(6) . . ? N4 C12 C8 123.7(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.566 _refine_diff_density_min -0.871 _refine_diff_density_rms 0.094 # Attachment 'web_deposit_cif_file_2_FrancescoDemartin_1328621263.HL1IBr2.cif' data_HL1IBr2 _database_code_depnum_ccdc_archive 'CCDC 865998' #TrackingRef 'web_deposit_cif_file_2_FrancescoDemartin_1328621263.HL1IBr2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 Br2 I N4 S' _chemical_formula_weight 528.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 '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 11.773(2) _cell_length_b 8.0600(10) _cell_length_c 18.058(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.440(10) _cell_angle_gamma 90.00 _cell_volume 1625.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 3.35 _cell_measurement_theta_max 22.54 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.158 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 7.009 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.523 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'SMART CCD diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7647 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.1707 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 23.32 _reflns_number_total 2330 _reflns_number_gt 1681 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0252P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2330 _refine_ls_number_parameters 185 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0640 _refine_ls_wR_factor_gt 0.0630 _refine_ls_goodness_of_fit_ref 0.841 _refine_ls_restrained_S_all 0.841 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.002 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 I I 0.42262(4) 0.86842(5) 0.67959(2) 0.04106(15) Uani 1 1 d . . . Br1 Br 0.50260(6) 0.71390(9) 0.57075(4) 0.0517(2) Uani 1 1 d . . . Br2 Br 0.33860(6) 1.03356(9) 0.78114(4) 0.0484(2) Uani 1 1 d . . . S S 0.66875(18) 0.6654(3) 0.98617(12) 0.0426(10) Uani 0.672(10) 1 d P . . S' S 0.7119(3) 0.5578(5) 0.9313(3) 0.0619(18) Uani 0.314(11) 1 d P . . N1 N 0.4904(4) 0.3301(6) 0.6680(3) 0.0365(13) Uani 1 1 d . . . HN1 H 0.4231 0.3195 0.6314 0.044 Uiso 1 1 calc R . . N2 N 0.7119(3) 0.5578(5) 0.9313(3) 0.0619(18) Uani 0.678(16) 1 d P . . N2' N 0.66875(18) 0.6654(3) 0.98617(12) 0.0426(10) Uani 0.320(16) 1 d P . . N3 N 0.4965(4) 0.5738(6) 0.8732(3) 0.0316(12) Uani 1 1 d . . . N4 N 0.2256(4) 0.8161(6) 0.9385(3) 0.0394(13) Uani 1 1 d . . . C1 C 0.4920(5) 0.4039(7) 0.7345(3) 0.0333(15) Uani 1 1 d . . . H1 H 0.4205 0.4388 0.7410 0.040 Uiso 1 1 calc R . . C2 C 0.5894(6) 0.2722(8) 0.6562(4) 0.0444(17) Uani 1 1 d . . . H2 H 0.5852 0.2187 0.6097 0.053 Uiso 1 1 calc R . . C3 C 0.6981(5) 0.2926(9) 0.7137(4) 0.0498(19) Uani 1 1 d . . . H3 H 0.7681 0.2552 0.7057 0.060 Uiso 1 1 calc R . . C4 C 0.7028(5) 0.3692(8) 0.7836(4) 0.0424(17) Uani 1 1 d . . . H4 H 0.7755 0.3800 0.8232 0.051 Uiso 1 1 calc R . . C5 C 0.5989(5) 0.4292(7) 0.7939(3) 0.0314(15) Uani 1 1 d . . . C6 C 0.5988(5) 0.5186(7) 0.8639(3) 0.0293(15) Uani 1 1 d . . . C7 C 0.5215(5) 0.6578(7) 0.9407(3) 0.0323(15) Uani 1 1 d . . . C8 C 0.4313(5) 0.7363(7) 0.9669(3) 0.0298(15) Uani 1 1 d . . . C9 C 0.4579(5) 0.8162(8) 1.0380(3) 0.0379(16) Uani 1 1 d . . . H9 H 0.5362 0.8169 1.0717 0.045 Uiso 1 1 calc R . . C10 C 0.3685(6) 0.8955(8) 1.0594(4) 0.0451(18) Uani 1 1 d . . . H10 H 0.3854 0.9476 1.1077 0.054 Uiso 1 1 calc R . . C11 C 0.2544(5) 0.8949(8) 1.0074(4) 0.0401(16) Uani 1 1 d . . . H11 H 0.1946 0.9514 1.0205 0.048 Uiso 1 1 calc R . . C12 C 0.3127(5) 0.7391(8) 0.9188(3) 0.0336(15) Uani 1 1 d . . . H12 H 0.2931 0.6851 0.8709 0.040 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 I 0.0345(2) 0.0394(3) 0.0426(3) 0.0047(2) 0.00270(18) -0.0045(2) Br1 0.0430(4) 0.0588(5) 0.0535(4) -0.0095(4) 0.0156(3) -0.0004(4) Br2 0.0473(4) 0.0582(5) 0.0346(4) -0.0021(3) 0.0055(3) -0.0055(4) S 0.0362(14) 0.0422(16) 0.0386(14) -0.0048(11) -0.0033(10) 0.0020(10) S' 0.043(2) 0.047(3) 0.104(4) 0.003(2) 0.036(2) -0.0014(18) N1 0.029(3) 0.035(3) 0.041(3) 0.000(3) 0.004(2) -0.004(2) N2 0.043(2) 0.047(3) 0.104(4) 0.003(2) 0.036(2) -0.0014(18) N2' 0.0362(14) 0.0422(16) 0.0386(14) -0.0048(11) -0.0033(10) 0.0020(10) N3 0.027(3) 0.034(3) 0.032(3) 0.003(2) 0.007(2) -0.001(2) N4 0.041(3) 0.044(3) 0.033(3) 0.001(3) 0.012(3) 0.001(3) C1 0.025(3) 0.036(4) 0.036(4) 0.003(3) 0.007(3) -0.003(3) C2 0.044(4) 0.045(4) 0.046(4) -0.007(3) 0.017(3) 0.001(3) C3 0.031(4) 0.054(5) 0.063(5) -0.005(4) 0.013(3) 0.006(3) C4 0.035(4) 0.048(4) 0.040(4) -0.005(4) 0.005(3) 0.008(3) C5 0.029(3) 0.027(3) 0.037(4) 0.006(3) 0.008(3) -0.001(3) C6 0.024(3) 0.027(3) 0.033(4) 0.007(3) 0.005(3) -0.001(3) C7 0.036(3) 0.024(3) 0.034(4) 0.006(3) 0.007(3) -0.002(3) C8 0.032(3) 0.027(4) 0.030(3) 0.005(3) 0.010(3) 0.000(3) C9 0.038(4) 0.039(4) 0.034(4) 0.005(3) 0.008(3) 0.000(3) C10 0.049(4) 0.040(4) 0.045(4) 0.001(3) 0.013(3) -0.004(3) C11 0.037(4) 0.042(4) 0.047(4) 0.008(3) 0.021(3) 0.003(3) C12 0.034(4) 0.039(4) 0.028(3) 0.000(3) 0.010(3) 0.000(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 I Br2 2.6946(9) . ? I Br1 2.7332(9) . ? S S' 1.520(4) . ? S C7 1.668(6) . ? S' C6 1.526(6) . ? N1 C2 1.334(7) . ? N1 C1 1.335(7) . ? N3 C7 1.343(7) . ? N3 C6 1.344(7) . ? N4 C12 1.338(7) . ? N4 C11 1.342(8) . ? C1 C5 1.387(8) . ? C2 C3 1.379(8) . ? C3 C4 1.392(9) . ? C4 C5 1.381(8) . ? C5 C6 1.456(8) . ? C7 C8 1.439(8) . ? C8 C9 1.380(8) . ? C8 C12 1.392(7) . ? C9 C10 1.386(8) . ? C10 C11 1.375(8) . ? 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 Br2 I Br1 176.91(3) . . ? S' S C7 99.6(3) . . ? S S' C6 104.5(3) . . ? C2 N1 C1 122.4(5) . . ? C7 N3 C6 109.4(5) . . ? C12 N4 C11 118.4(5) . . ? N1 C1 C5 120.8(6) . . ? N1 C2 C3 119.2(6) . . ? C2 C3 C4 119.8(6) . . ? C5 C4 C3 119.6(6) . . ? C4 C5 C1 118.1(6) . . ? C4 C5 C6 122.3(5) . . ? C1 C5 C6 119.6(6) . . ? N3 C6 C5 121.3(5) . . ? N3 C6 S' 114.9(5) . . ? C5 C6 S' 123.7(5) . . ? N3 C7 C8 123.2(5) . . ? N3 C7 S 111.2(5) . . ? C8 C7 S 125.6(5) . . ? C9 C8 C12 117.4(6) . . ? C9 C8 C7 122.5(5) . . ? C12 C8 C7 120.0(5) . . ? C8 C9 C10 120.4(6) . . ? C11 C10 C9 118.1(6) . . ? N4 C11 C10 122.7(6) . . ? N4 C12 C8 122.9(6) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 23.32 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.739 _refine_diff_density_min -0.620 _refine_diff_density_rms 0.097 # Attachment 'web_deposit_cif_file_3_FrancescoDemartin_1328621263.HL2I3.cif' data_HL2I3 _database_code_depnum_ccdc_archive 'CCDC 865999' #TrackingRef 'web_deposit_cif_file_3_FrancescoDemartin_1328621263.HL2I3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 I6 N8 O S2' _chemical_formula_weight 1318.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 '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 10.905(4) _cell_length_b 11.753(10) _cell_length_c 16.185(6) _cell_angle_alpha 75.08(4) _cell_angle_beta 72.27(3) _cell_angle_gamma 80.78(5) _cell_volume 1901.7(19) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.62 _cell_measurement_theta_max 14.32 _exptl_crystal_description pseudoprism _exptl_crystal_colour brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1220 _exptl_absorpt_coefficient_mu 5.045 _exptl_absorpt_correction_type semiempirical _exptl_absorpt_correction_T_min 0.520 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details Psi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'ENRAF NONIUS CAD4 diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5248 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0620 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 22.98 _reflns_number_total 5248 _reflns_number_gt 3180 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1038P)^2^+10.8705P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5248 _refine_ls_number_parameters 414 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.1253 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.2001 _refine_ls_wR_factor_gt 0.1750 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.008 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 0.05148(4) 1.16024(4) 0.28935(4) 0.10625(19) Uani 1 1 d . . . I2 I 0.16133(3) 0.95019(3) 0.39370(2) 0.07782(12) Uani 1 1 d . . . I3 I 0.27687(4) 0.73671(4) 0.48697(3) 0.09167(15) Uani 1 1 d . . . I4 I 0.36061(4) 0.45069(4) 0.65321(3) 0.10625(17) Uani 1 1 d . . . I5 I 0.28313(3) 0.22703(3) 0.76570(2) 0.07953(12) Uani 1 1 d . . . I6 I 0.18986(4) 0.00320(4) 0.88777(3) 0.10186(18) Uani 1 1 d . . . S1 S -0.00649(16) 0.47466(15) 0.38176(13) 0.0820(7) Uani 0.6946(19) 1 d P . . N2' N -0.00649(16) 0.47466(15) 0.38176(13) 0.0820(7) Uani 0.302(2) 1 d P . . N2 N 0.0048(3) 0.5990(3) 0.3240(2) 0.0931(11) Uani 0.697(2) 1 d P . . S1' S 0.0048(3) 0.5990(3) 0.3240(2) 0.0931(11) Uani 0.300(2) 1 d P . . N1 N 0.2970(3) 0.1468(3) 0.5474(2) 0.0562(12) Uani 1 1 d . . . N3 N 0.2180(3) 0.5357(3) 0.3433(2) 0.0491(11) Uani 1 1 d . . . N4 N 0.2921(4) 0.9384(3) 0.1410(2) 0.0595(13) Uani 1 1 d . . . C1 C 0.3192(4) 0.3390(4) 0.4556(3) 0.0632(17) Uani 1 1 d . . . H1 H 0.3689 0.4028 0.4285 0.076 Uiso 1 1 calc R . . C2 C 0.3657(4) 0.2400(4) 0.5052(3) 0.0644(16) Uani 1 1 d . . . H2 H 0.4490 0.2366 0.5103 0.077 Uiso 1 1 calc R . . C3 C 0.1815(5) 0.1499(4) 0.5391(3) 0.0709(19) Uani 1 1 d . . . H3 H 0.1347 0.0844 0.5675 0.085 Uiso 1 1 calc R . . C4 C 0.1255(4) 0.2466(4) 0.4896(3) 0.0663(17) Uani 1 1 d . . . H4 H 0.0421 0.2469 0.4857 0.080 Uiso 1 1 calc R . . C5 C 0.1970(4) 0.3438(3) 0.4458(3) 0.0483(14) Uani 1 1 d . . . C6 C 0.1434(4) 0.4508(4) 0.3922(3) 0.0508(14) Uani 1 1 d . . . C7 C 0.1420(4) 0.6214(4) 0.3033(3) 0.0543(15) Uani 1 1 d . . . C8 C 0.1961(4) 0.7319(3) 0.2454(3) 0.0505(14) Uani 1 1 d . . . C9 C 0.1185(4) 0.8169(4) 0.1980(3) 0.0571(15) Uani 1 1 d . . . H9 H 0.0356 0.8032 0.2006 0.068 Uiso 1 1 calc R . . C10 C 0.1714(5) 0.9195(4) 0.1484(3) 0.0699(18) Uani 1 1 d . . . H10 H 0.1216 0.9780 0.1189 0.084 Uiso 1 1 calc R . . C11 C 0.3672(5) 0.8571(4) 0.1853(3) 0.0591(16) Uani 1 1 d . . . H11 H 0.4498 0.8729 0.1816 0.071 Uiso 1 1 calc R . . C12 C 0.3204(4) 0.7516(3) 0.2353(3) 0.0469(14) Uani 1 1 d . . . H12 H 0.3734 0.6936 0.2624 0.056 Uiso 1 1 calc R . . S2 S 0.31606(14) 0.37921(12) 0.17993(10) 0.0595(5) Uani 0.7308(18) 1 d P . . N6' N 0.31606(14) 0.37921(12) 0.17993(10) 0.0595(5) Uani 0.271(2) 1 d P . . N6 N 0.3299(3) 0.5023(2) 0.12011(17) 0.0733(10) Uani 0.729(2) 1 d P . . S2' S 0.3299(3) 0.5023(2) 0.12011(17) 0.0733(10) Uani 0.272(2) 1 d P . . N5 N 0.6067(3) 0.0477(3) 0.3553(2) 0.0561(13) Uani 1 1 d . . . N7 N 0.5322(3) 0.4457(3) 0.1538(2) 0.0504(12) Uani 1 1 d . . . N8 N 0.6122(3) 0.8550(3) -0.0442(2) 0.0493(11) Uani 1 1 d . . . C13 C 0.6262(4) 0.2456(4) 0.2738(3) 0.0563(15) Uani 1 1 d . . . H13 H 0.6731 0.3116 0.2539 0.068 Uiso 1 1 calc R . . C14 C 0.6707(5) 0.1431(5) 0.3269(3) 0.0695(18) Uani 1 1 d . . . H14 H 0.7463 0.1422 0.3424 0.083 Uiso 1 1 calc R . . C15 C 0.4990(4) 0.0500(4) 0.3343(3) 0.0646(17) Uani 1 1 d . . . H15 H 0.4558 -0.0182 0.3560 0.078 Uiso 1 1 calc R . . C16 C 0.4428(5) 0.1479(4) 0.2813(3) 0.0615(16) Uani 1 1 d . . . H16 H 0.3663 0.1455 0.2678 0.074 Uiso 1 1 calc R . . C17 C 0.5130(4) 0.2499(3) 0.2505(3) 0.0498(14) Uani 1 1 d . . . C18 C 0.4620(4) 0.3566(4) 0.1971(3) 0.0460(14) Uani 1 1 d . . . C19 C 0.4634(4) 0.5309(3) 0.1085(2) 0.0417(12) Uani 1 1 d . . . C20 C 0.5128(4) 0.6430(3) 0.0541(3) 0.0447(13) Uani 1 1 d . . . C21 C 0.4432(5) 0.7245(4) 0.0049(3) 0.0604(16) Uani 1 1 d . . . H21 H 0.3629 0.7105 0.0026 0.072 Uiso 1 1 calc R . . C22 C 0.4992(5) 0.8303(4) -0.0421(3) 0.0603(16) Uani 1 1 d . . . H22 H 0.4515 0.8874 -0.0743 0.072 Uiso 1 1 calc R . . C23 C 0.6825(4) 0.7744(4) 0.0008(3) 0.0566(15) Uani 1 1 d . . . H23 H 0.7642 0.7907 -0.0011 0.068 Uiso 1 1 calc R . . C24 C 0.6370(4) 0.6653(4) 0.0513(3) 0.0544(15) Uani 1 1 d . . . H24 H 0.6876 0.6094 0.0820 0.065 Uiso 1 1 calc R . . O O 1.1323(4) 0.6251(4) -0.0367(5) 0.191(4) Uani 1 1 d . . . C25 C 1.0975(6) 0.5468(8) -0.1517(4) 0.161(4) Uani 1 1 d . . . C26 C 1.0631(7) 0.6663(8) -0.1032(5) 0.142(3) Uani 1 1 d . . . C27 C 1.0048(4) 0.6337(4) 0.0720(3) 0.1660(13) Uani 1 1 d P . . C28 C 1.0109(5) 0.4708(8) 0.1340(3) 0.232(4) Uani 1 1 d P . . 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 0.0843(2) 0.0741(2) 0.1433(4) -0.0157(2) -0.0129(2) -0.0089(2) I2 0.06871(17) 0.07844(18) 0.0834(2) -0.03508(15) 0.00728(16) -0.02584(15) I3 0.0892(2) 0.1081(3) 0.0831(2) -0.0178(2) -0.02693(17) -0.0236(2) I4 0.1061(3) 0.0951(3) 0.1297(3) -0.0403(2) -0.0345(2) -0.0143(2) I5 0.07639(17) 0.0988(2) 0.07639(17) -0.03873(16) -0.03769(13) 0.01965(17) I6 0.1026(2) 0.1093(3) 0.0876(2) -0.0062(2) -0.04215(19) 0.0137(2) S1 0.0780(9) 0.0546(9) 0.1019(12) 0.0181(9) -0.0311(8) -0.0190(8) N2' 0.0780(9) 0.0546(9) 0.1019(12) 0.0181(9) -0.0311(8) -0.0190(8) N2 0.0836(14) 0.0720(18) 0.124(2) 0.0088(16) -0.0560(13) -0.0029(14) S1' 0.0836(14) 0.0720(18) 0.124(2) 0.0088(16) -0.0560(13) -0.0029(14) N1 0.0653(18) 0.050(2) 0.0616(19) -0.0090(16) -0.0336(14) -0.0040(16) N3 0.0655(18) 0.0298(16) 0.0496(18) 0.0010(14) -0.0183(15) -0.0085(15) N4 0.072(2) 0.049(2) 0.0597(19) -0.0134(16) -0.0196(16) -0.0101(17) C1 0.060(2) 0.041(2) 0.082(3) 0.005(2) -0.025(2) -0.007(2) C2 0.060(2) 0.049(3) 0.086(3) 0.008(2) -0.0362(19) -0.0160(19) C3 0.087(3) 0.040(3) 0.074(3) 0.020(2) -0.032(2) -0.007(2) C4 0.058(2) 0.047(2) 0.094(3) 0.013(2) -0.037(2) -0.0198(19) C5 0.068(2) 0.031(2) 0.042(2) 0.0010(17) -0.0130(18) -0.0148(18) C6 0.063(2) 0.040(2) 0.047(2) -0.0020(18) -0.0195(18) -0.0032(19) C7 0.080(2) 0.043(2) 0.042(2) -0.0037(18) -0.0194(18) -0.015(2) C8 0.072(2) 0.0272(19) 0.057(2) -0.0105(17) -0.0247(18) -0.0021(18) C9 0.075(2) 0.041(2) 0.059(2) 0.001(2) -0.0371(18) 0.000(2) C10 0.100(3) 0.040(3) 0.070(3) 0.004(2) -0.044(2) 0.004(2) C11 0.067(2) 0.048(2) 0.059(2) -0.017(2) -0.019(2) 0.016(2) C12 0.078(2) 0.0192(18) 0.044(2) -0.0016(16) -0.0264(18) 0.0036(18) S2 0.0651(8) 0.0407(7) 0.0631(8) -0.0016(6) -0.0098(7) -0.0095(6) N6' 0.0651(8) 0.0407(7) 0.0631(8) -0.0016(6) -0.0098(7) -0.0095(6) N6 0.0898(15) 0.0572(15) 0.0750(15) -0.0168(12) -0.0338(12) 0.0127(13) S2' 0.0898(15) 0.0572(15) 0.0750(15) -0.0168(12) -0.0338(12) 0.0127(13) N5 0.0653(19) 0.0408(19) 0.058(2) 0.0035(17) -0.0200(16) -0.0105(16) N7 0.0609(18) 0.0355(17) 0.0569(18) -0.0106(15) -0.0185(15) -0.0052(15) N8 0.0645(18) 0.0338(16) 0.0519(18) -0.0033(14) -0.0185(14) -0.0161(14) C13 0.062(2) 0.042(2) 0.063(3) 0.001(2) -0.0176(19) -0.0184(18) C14 0.066(2) 0.072(3) 0.072(3) -0.001(2) -0.030(2) -0.011(2) C15 0.074(3) 0.058(3) 0.058(3) -0.006(2) -0.010(2) -0.023(2) C16 0.074(2) 0.044(2) 0.059(3) 0.015(2) -0.023(2) -0.017(2) C17 0.071(2) 0.031(2) 0.045(2) -0.0051(17) -0.0123(19) -0.0097(18) C18 0.059(2) 0.034(2) 0.040(2) -0.0025(17) -0.0114(17) -0.0033(18) C19 0.055(2) 0.037(2) 0.0368(18) -0.0147(15) -0.0175(15) 0.0043(17) C20 0.065(2) 0.0282(18) 0.045(2) -0.0082(16) -0.0163(17) -0.0121(16) C21 0.072(3) 0.053(3) 0.060(2) -0.011(2) -0.025(2) -0.003(2) C22 0.089(3) 0.039(2) 0.048(2) 0.006(2) -0.031(2) 0.006(2) C23 0.073(2) 0.028(2) 0.074(2) -0.0006(19) -0.0407(18) 0.0031(19) C24 0.074(2) 0.035(2) 0.058(2) -0.0019(19) -0.0364(18) 0.008(2) O 0.051(2) 0.089(3) 0.381(8) 0.021(4) -0.050(3) -0.004(2) C25 0.102(3) 0.279(8) 0.061(3) -0.032(4) -0.038(3) 0.116(4) C26 0.092(4) 0.174(7) 0.098(5) 0.063(5) -0.001(4) -0.036(4) C27 0.1251(19) 0.221(2) 0.268(2) -0.2266(15) -0.1572(15) 0.1377(19) C28 0.093(3) 0.477(10) 0.034(2) -0.006(4) -0.010(2) 0.140(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 I2 2.919(2) . ? I2 I3 2.891(2) . ? I4 I5 2.872(2) . ? I5 I6 2.969(2) . ? S1 N2 1.520(3) . ? S1 C6 1.666(5) . ? N2 C7 1.482(6) . ? N1 C3 1.300(7) . ? N1 C2 1.340(6) . ? N3 C6 1.321(5) . ? N3 C7 1.358(5) . ? N4 C10 1.334(7) . ? N4 C11 1.361(6) . ? C1 C2 1.355(6) . ? C1 C5 1.380(7) . ? C3 C4 1.384(7) . ? C4 C5 1.395(6) . ? C5 C6 1.478(6) . ? C7 C8 1.481(6) . ? C8 C12 1.365(6) . ? C8 C9 1.426(6) . ? C9 C10 1.369(6) . ? C11 C12 1.374(6) . ? S2 N6 1.520(3) . ? S2 C18 1.666(5) . ? N6 C19 1.492(5) . ? N5 C15 1.313(7) . ? N5 C14 1.321(6) . ? N7 C18 1.314(5) . ? N7 C19 1.349(5) . ? N8 C22 1.300(6) . ? N8 C23 1.330(6) . ? C13 C17 1.386(7) . ? C13 C14 1.399(6) . ? C15 C16 1.422(6) . ? C16 C17 1.423(6) . ? C17 C18 1.462(6) . ? C19 C20 1.464(5) . ? C20 C21 1.368(6) . ? C20 C24 1.405(7) . ? C21 C22 1.404(6) . ? C23 C24 1.406(6) . ? O C26 1.440(11) . ? O C27 1.896(7) . ? C25 C28 1.167(9) 2_765 ? C25 C26 1.717(13) . ? C27 C28 1.920(9) . ? C28 C25 1.167(9) 2_765 ? 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 I3 I2 I1 176.42(2) . . ? I4 I5 I6 176.719(18) . . ? N2 S1 C6 97.2(2) . . ? C7 N2 S1 105.7(2) . . ? C3 N1 C2 118.9(4) . . ? C6 N3 C7 106.5(4) . . ? C10 N4 C11 121.0(4) . . ? C2 C1 C5 119.0(4) . . ? N1 C2 C1 122.9(5) . . ? N1 C3 C4 122.7(4) . . ? C3 C4 C5 118.4(5) . . ? C1 C5 C4 118.1(4) . . ? C1 C5 C6 120.3(4) . . ? C4 C5 C6 121.6(4) . . ? N3 C6 C5 120.2(4) . . ? N3 C6 S1 113.8(3) . . ? C5 C6 S1 125.9(3) . . ? N3 C7 C8 120.1(4) . . ? N3 C7 N2 116.3(3) . . ? C8 C7 N2 123.5(4) . . ? C12 C8 C9 119.8(4) . . ? C12 C8 C7 120.7(4) . . ? C9 C8 C7 119.5(4) . . ? C10 C9 C8 117.1(5) . . ? N4 C10 C9 122.2(4) . . ? N4 C11 C12 119.6(5) . . ? C8 C12 C11 120.1(4) . . ? N6 S2 C18 97.7(2) . . ? C19 N6 S2 106.4(2) . . ? C15 N5 C14 119.3(4) . . ? C18 N7 C19 109.6(4) . . ? C22 N8 C23 118.4(4) . . ? C17 C13 C14 120.8(4) . . ? N5 C14 C13 120.9(5) . . ? N5 C15 C16 125.7(4) . . ? C15 C16 C17 114.6(5) . . ? C13 C17 C16 118.8(4) . . ? C13 C17 C18 122.2(4) . . ? C16 C17 C18 119.0(4) . . ? N7 C18 C17 121.7(4) . . ? N7 C18 S2 112.2(3) . . ? C17 C18 S2 126.0(3) . . ? N7 C19 C20 123.7(4) . . ? N7 C19 N6 114.0(3) . . ? C20 C19 N6 122.3(3) . . ? C21 C20 C24 119.5(4) . . ? C21 C20 C19 122.1(4) . . ? C24 C20 C19 118.3(4) . . ? C20 C21 C22 116.7(5) . . ? N8 C22 C21 125.3(4) . . ? N8 C23 C24 121.9(4) . . ? C23 C24 C20 118.1(4) . . ? C26 O C27 104.2(4) . . ? C28 C25 C26 93.7(7) 2_765 . ? O C26 C25 100.0(6) . . ? O C27 C28 100.7(3) . . ? C25 C28 C27 100.7(6) 2_765 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 22.98 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.430 _refine_diff_density_min -1.672 _refine_diff_density_rms 0.173 # Attachment 'web_deposit_cif_file_4_FrancescoDemartin_1328621263.HL2IBr2.cif' data_HL2IBr2 _database_code_depnum_ccdc_archive 'CCDC 866000' #TrackingRef 'web_deposit_cif_file_4_FrancescoDemartin_1328621263.HL2IBr2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H9 Br2 I N4 S' _chemical_formula_weight 528.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.3060(9) _cell_length_b 24.8569(18) _cell_length_c 14.2466(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.290(10) _cell_angle_gamma 90.00 _cell_volume 4704.2(6) _cell_formula_units_Z 12 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 3.34 _cell_measurement_theta_max 20.54 _exptl_crystal_description prism _exptl_crystal_colour 'dark orange' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2976 _exptl_absorpt_coefficient_mu 7.266 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.652 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 'SMART CCD diffractometer' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43707 _diffrn_reflns_av_R_equivalents 0.0544 _diffrn_reflns_av_sigmaI/netI 0.0699 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 26.04 _reflns_number_total 9265 _reflns_number_gt 5581 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0912P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9265 _refine_ls_number_parameters 553 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1710 _refine_ls_wR_factor_gt 0.1622 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.007 _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 0.62275(5) 0.84709(3) 0.51279(5) 0.0398(2) Uani 1 1 d . . . Br1 Br 0.58957(9) 0.74050(4) 0.53986(7) 0.0438(3) Uani 1 1 d . . . Br2 Br 0.65761(10) 0.95503(5) 0.48254(8) 0.0559(4) Uani 1 1 d . . . I2 I 0.28551(5) 0.48829(3) 0.54838(5) 0.0419(2) Uani 1 1 d . . . Br3 Br 0.36335(11) 0.39498(5) 0.48563(9) 0.0629(4) Uani 1 1 d . . . Br4 Br 0.19429(10) 0.57664(5) 0.62058(10) 0.0636(4) Uani 1 1 d . . . I3 I 0.18574(5) 0.67643(3) 0.13101(5) 0.0391(2) Uani 1 1 d . . . Br5 Br 0.21260(10) 0.56555(5) 0.10569(10) 0.0570(3) Uani 1 1 d . . . Br6 Br 0.15976(8) 0.78539(4) 0.15079(7) 0.0358(3) Uani 1 1 d . . . S1A S 0.3377(3) 0.28616(17) 0.7082(3) 0.0431(16) Uani 0.520(14) 1 d P . . S1A' S 0.3421(4) 0.2298(2) 0.7068(4) 0.052(2) Uani 0.414(14) 1 d P . . N1A N 0.1157(6) 0.4522(3) 0.8223(6) 0.039(2) Uani 1 1 d . . . HN1A H 0.0927 0.4831 0.8376 0.047 Uiso 1 1 calc R . . N2A' N 0.3377(3) 0.28616(17) 0.7082(3) 0.0431(16) Uani 0.443(18) 1 d P . . N2A N 0.3421(4) 0.2298(2) 0.7068(4) 0.052(2) Uani 0.549(18) 1 d P . . N3A N 0.1802(6) 0.2538(3) 0.7743(6) 0.0318(19) Uani 1 1 d . . . N4A N 0.1442(7) 0.0519(3) 0.8028(6) 0.039(2) Uani 1 1 d . . . C1A C 0.0964(7) 0.3571(4) 0.8119(7) 0.034(2) Uani 1 1 d . . . H1A H 0.0577 0.3266 0.8218 0.041 Uiso 1 1 calc R . . C2A C 0.0612(8) 0.4077(4) 0.8332(7) 0.038(3) Uani 1 1 d . . . H2A H -0.0027 0.4109 0.8560 0.046 Uiso 1 1 calc R . . C3A C 0.2075(8) 0.4480(4) 0.7870(7) 0.041(3) Uani 1 1 d . . . H3A H 0.2463 0.4787 0.7802 0.049 Uiso 1 1 calc R . . C4A C 0.2445(8) 0.3985(4) 0.7608(7) 0.037(2) Uani 1 1 d . . . H4A H 0.3060 0.3964 0.7332 0.044 Uiso 1 1 calc R . . C5A C 0.1905(7) 0.3526(4) 0.7755(6) 0.031(2) Uani 1 1 d . . . C6A C 0.2297(7) 0.2990(4) 0.7566(6) 0.032(2) Uani 1 1 d . . . C7A C 0.2360(7) 0.2107(4) 0.7511(7) 0.034(2) Uani 1 1 d . . . C8A C 0.2041(7) 0.1561(4) 0.7652(6) 0.030(2) Uani 1 1 d . . . C9A C 0.2608(8) 0.1121(4) 0.7401(7) 0.041(3) Uani 1 1 d . . . H9A H 0.3207 0.1177 0.7108 0.050 Uiso 1 1 calc R . . C10A C 0.2297(8) 0.0599(4) 0.7580(7) 0.040(3) Uani 1 1 d . . . H10A H 0.2674 0.0307 0.7393 0.048 Uiso 1 1 calc R . . C11A C 0.0860(8) 0.0941(4) 0.8269(7) 0.038(3) Uani 1 1 d . . . H11A H 0.0265 0.0877 0.8563 0.046 Uiso 1 1 calc R . . C12A C 0.1143(8) 0.1462(4) 0.8083(7) 0.038(3) Uani 1 1 d . . . H12A H 0.0735 0.1747 0.8243 0.045 Uiso 1 1 calc R . . S1B S 0.8633(4) 0.7843(2) 0.9835(3) 0.063(2) Uani 0.600(16) 1 d P . . S1B' S 0.8641(4) 0.7309(2) 0.9870(3) 0.044(2) Uani 0.377(16) 1 d P . . N1B N 1.0805(6) 0.9522(3) 0.8627(6) 0.039(2) Uani 1 1 d . . . HN1B H 1.1030 0.9833 0.8475 0.047 Uiso 1 1 calc R . . N2B N 0.8641(4) 0.7309(2) 0.9870(3) 0.044(2) Uani 0.61(2) 1 d P . . N2B' N 0.8633(4) 0.7843(2) 0.9835(3) 0.063(2) Uani 0.39(2) 1 d P . . N3B N 1.0203(6) 0.7532(3) 0.9101(5) 0.0310(19) Uani 1 1 d . . . N4B N 1.0510(7) 0.5509(3) 0.8759(6) 0.039(2) Uani 1 1 d . . . C1B C 1.1004(7) 0.8584(4) 0.8722(7) 0.038(3) Uani 1 1 d . . . H1B H 1.1388 0.8281 0.8603 0.046 Uiso 1 1 calc R . . C2B C 1.1352(8) 0.9083(4) 0.8497(8) 0.043(3) Uani 1 1 d . . . H2B H 1.1980 0.9115 0.8248 0.052 Uiso 1 1 calc R . . C3B C 0.9893(8) 0.9481(4) 0.9002(7) 0.040(3) Uani 1 1 d . . . H3B H 0.9510 0.9788 0.9086 0.049 Uiso 1 1 calc R . . C4B C 0.9524(8) 0.8981(4) 0.9261(7) 0.034(2) Uani 1 1 d . . . H4B H 0.8902 0.8954 0.9525 0.041 Uiso 1 1 calc R . . C5B C 1.0093(7) 0.8524(4) 0.9122(6) 0.028(2) Uani 1 1 d . . . C6B C 0.9706(7) 0.7989(4) 0.9348(7) 0.033(2) Uani 1 1 d . . . C7B C 0.9650(8) 0.7116(4) 0.9363(7) 0.036(2) Uani 1 1 d . . . C8B C 0.9966(8) 0.6559(4) 0.9172(6) 0.033(2) Uani 1 1 d . . . C9B C 0.9323(8) 0.6123(4) 0.9348(6) 0.039(3) Uani 1 1 d . . . H9B H 0.8705 0.6184 0.9604 0.046 Uiso 1 1 calc R . . C10B C 0.9620(8) 0.5596(4) 0.9134(7) 0.038(3) Uani 1 1 d . . . H10B H 0.9200 0.5308 0.9251 0.045 Uiso 1 1 calc R . . C11B C 1.1125(8) 0.5921(4) 0.8589(8) 0.044(3) Uani 1 1 d . . . H11B H 1.1733 0.5850 0.8323 0.052 Uiso 1 1 calc R . . C12B C 1.0883(7) 0.6452(4) 0.8796(7) 0.038(3) Uani 1 1 d . . . H12B H 1.1330 0.6729 0.8684 0.045 Uiso 1 1 calc R . . S1C S 0.3323(4) 0.8078(2) 0.9456(5) 0.070(3) Uani 0.369(16) 1 d P . . S1C' S 0.3179(3) 0.75185(18) 0.9440(3) 0.0614(18) Uani 0.640(16) 1 d P . . N1C N 0.4814(6) 0.9704(3) 0.7526(6) 0.043(2) Uani 1 1 d . . . HN1C H 0.4991 1.0016 0.7330 0.051 Uiso 1 1 calc R . . N2C N 0.3179(3) 0.75185(18) 0.9440(3) 0.0614(18) Uani 0.37(2) 1 d P . . N2C' N 0.3323(4) 0.8078(2) 0.9456(5) 0.070(3) Uani 0.64(2) 1 d P . . N3C N 0.4119(6) 0.7713(3) 0.8046(6) 0.035(2) Uani 1 1 d . . . N4C N 0.4437(7) 0.5683(3) 0.7871(7) 0.050(3) Uani 1 1 d . . . C1C C 0.4585(8) 0.8773(4) 0.7259(8) 0.041(3) Uani 1 1 d . . . H1C H 0.4640 0.8479 0.6863 0.050 Uiso 1 1 calc R . . C2C C 0.4870(8) 0.9272(4) 0.6984(8) 0.045(3) Uani 1 1 d . . . H2C H 0.5114 0.9311 0.6389 0.054 Uiso 1 1 calc R . . C3C C 0.4469(8) 0.9642(4) 0.8398(8) 0.045(3) Uani 1 1 d . . . H3C H 0.4455 0.9938 0.8795 0.054 Uiso 1 1 calc R . . C4C C 0.4148(8) 0.9162(4) 0.8704(8) 0.042(3) Uani 1 1 d . . . H4C H 0.3884 0.9134 0.9293 0.050 Uiso 1 1 calc R . . C5C C 0.4212(7) 0.8712(4) 0.8144(8) 0.036(2) Uani 1 1 d . . . C6C C 0.3907(7) 0.8174(4) 0.8485(8) 0.037(2) Uani 1 1 d . . . C7C C 0.3773(7) 0.7304(4) 0.8541(8) 0.035(2) Uani 1 1 d . . . C8C C 0.3937(7) 0.6743(4) 0.8290(8) 0.037(2) Uani 1 1 d . . . C9C C 0.3741(7) 0.6343(4) 0.8911(8) 0.044(3) Uani 1 1 d . . . H9C H 0.3443 0.6421 0.9469 0.053 Uiso 1 1 calc R . . C10C C 0.4000(8) 0.5807(4) 0.8692(8) 0.049(3) Uani 1 1 d . . . H10C H 0.3871 0.5533 0.9113 0.059 Uiso 1 1 calc R . . C11C C 0.4571(9) 0.6090(5) 0.7255(8) 0.053(3) Uani 1 1 d . . . H11C H 0.4823 0.6008 0.6677 0.063 Uiso 1 1 calc R . . C12C C 0.4349(8) 0.6619(4) 0.7449(8) 0.044(3) Uani 1 1 d . . . H12C H 0.4476 0.6889 0.7019 0.052 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 0.0404(4) 0.0442(4) 0.0349(4) -0.0060(3) 0.0023(3) 0.0060(3) Br1 0.0542(7) 0.0410(6) 0.0358(6) 0.0026(5) -0.0002(5) -0.0051(5) Br2 0.0789(9) 0.0392(6) 0.0510(7) -0.0047(5) 0.0150(7) 0.0029(6) I2 0.0438(4) 0.0401(4) 0.0419(4) 0.0076(3) 0.0036(3) -0.0069(3) Br3 0.0680(9) 0.0649(8) 0.0540(8) -0.0196(6) -0.0108(7) 0.0165(7) Br4 0.0666(9) 0.0507(8) 0.0737(9) -0.0114(7) 0.0046(7) 0.0107(7) I3 0.0385(4) 0.0376(4) 0.0415(4) 0.0032(3) 0.0049(3) -0.0044(3) Br5 0.0563(8) 0.0383(7) 0.0767(9) 0.0005(6) 0.0067(7) 0.0015(6) Br6 0.0460(6) 0.0243(5) 0.0366(6) -0.0101(4) -0.0024(5) 0.0100(4) S1A 0.036(3) 0.045(3) 0.048(3) 0.010(2) 0.005(2) -0.013(2) S1A' 0.048(3) 0.066(4) 0.044(3) -0.010(3) 0.006(3) 0.021(3) N1A 0.044(6) 0.029(5) 0.043(5) 0.001(4) -0.002(4) 0.009(4) N2A' 0.036(3) 0.045(3) 0.048(3) 0.010(2) 0.005(2) -0.013(2) N2A 0.048(3) 0.066(4) 0.044(3) -0.010(3) 0.006(3) 0.021(3) N3A 0.026(4) 0.036(5) 0.033(5) 0.002(4) 0.003(4) 0.003(4) N4A 0.046(6) 0.037(5) 0.033(5) 0.005(4) -0.002(4) -0.007(4) C1A 0.037(6) 0.028(5) 0.037(6) -0.001(4) -0.001(5) 0.000(4) C2A 0.025(6) 0.049(7) 0.040(6) 0.005(5) -0.001(5) 0.007(5) C3A 0.036(6) 0.045(6) 0.042(6) 0.007(5) 0.006(5) 0.003(5) C4A 0.031(6) 0.044(6) 0.036(6) 0.007(5) 0.005(5) -0.002(5) C5A 0.029(6) 0.040(6) 0.024(5) -0.001(4) 0.001(4) 0.001(5) C6A 0.036(6) 0.038(6) 0.021(5) 0.005(4) 0.000(4) 0.004(5) C7A 0.030(6) 0.039(6) 0.034(6) -0.009(5) 0.000(5) 0.005(5) C8A 0.029(5) 0.032(5) 0.027(5) -0.003(4) -0.005(4) -0.005(4) C9A 0.031(6) 0.056(7) 0.037(6) -0.009(5) 0.004(5) -0.003(5) C10A 0.034(6) 0.037(6) 0.049(7) 0.003(5) 0.001(5) 0.006(5) C11A 0.042(7) 0.030(6) 0.043(6) 0.004(5) 0.002(5) -0.004(5) C12A 0.047(7) 0.028(5) 0.039(6) -0.009(5) 0.009(5) -0.002(5) S1B 0.069(4) 0.066(4) 0.056(3) -0.012(2) 0.005(3) 0.025(3) S1B' 0.034(3) 0.060(4) 0.039(3) 0.012(2) 0.004(2) -0.017(2) N1B 0.049(6) 0.029(5) 0.037(5) 0.002(4) -0.006(4) -0.009(4) N2B 0.034(3) 0.060(4) 0.039(3) 0.012(2) 0.004(2) -0.017(2) N2B' 0.069(4) 0.066(4) 0.056(3) -0.012(2) 0.005(3) 0.025(3) N3B 0.030(5) 0.030(4) 0.033(5) 0.002(4) 0.001(4) -0.002(4) N4B 0.047(6) 0.030(5) 0.040(5) -0.002(4) -0.006(5) 0.004(4) C1B 0.032(6) 0.037(6) 0.046(7) -0.003(5) 0.003(5) 0.009(5) C2B 0.034(6) 0.044(7) 0.051(7) -0.004(5) 0.002(5) 0.008(5) C3B 0.046(7) 0.037(6) 0.038(6) -0.002(5) 0.004(5) -0.001(5) C4B 0.035(6) 0.034(6) 0.033(6) -0.006(4) -0.001(5) 0.002(5) C5B 0.028(5) 0.029(5) 0.028(5) 0.001(4) -0.005(4) -0.001(4) C6B 0.032(6) 0.042(6) 0.026(5) 0.000(4) -0.001(4) 0.003(5) C7B 0.038(6) 0.048(6) 0.022(5) 0.000(5) -0.003(5) 0.011(5) C8B 0.041(6) 0.034(5) 0.024(5) -0.002(4) -0.001(5) -0.001(5) C9B 0.035(6) 0.056(7) 0.023(5) -0.001(5) -0.008(5) 0.000(5) C10B 0.043(7) 0.034(6) 0.036(6) 0.001(5) -0.003(5) -0.006(5) C11B 0.037(6) 0.042(7) 0.051(7) 0.000(5) 0.002(5) -0.006(5) C12B 0.028(6) 0.036(6) 0.050(7) 0.002(5) 0.005(5) -0.008(5) S1C 0.053(4) 0.063(5) 0.095(5) -0.033(4) 0.009(3) 0.018(3) S1C' 0.063(3) 0.055(3) 0.068(3) 0.014(2) 0.023(2) -0.011(2) N1C 0.041(5) 0.027(5) 0.061(6) 0.000(4) 0.005(5) 0.001(4) N2C 0.063(3) 0.055(3) 0.068(3) 0.014(2) 0.023(2) -0.011(2) N2C' 0.053(4) 0.063(5) 0.095(5) -0.033(4) 0.009(3) 0.018(3) N3C 0.025(5) 0.026(4) 0.054(6) -0.002(4) 0.002(4) -0.002(4) N4C 0.045(6) 0.026(5) 0.078(7) 0.002(5) -0.002(5) -0.003(4) C1C 0.035(6) 0.028(5) 0.063(8) 0.005(5) 0.010(6) 0.004(5) C2C 0.040(7) 0.038(6) 0.058(7) 0.003(5) 0.007(6) 0.001(5) C3C 0.046(7) 0.030(6) 0.060(8) -0.010(5) 0.000(6) 0.004(5) C4C 0.050(7) 0.028(6) 0.047(7) -0.003(5) 0.003(6) 0.007(5) C5C 0.020(5) 0.032(5) 0.056(7) 0.000(5) -0.001(5) 0.005(4) C6C 0.025(5) 0.030(5) 0.055(7) 0.004(5) 0.006(5) 0.009(4) C7C 0.024(5) 0.025(5) 0.057(7) 0.004(5) 0.002(5) 0.000(4) C8C 0.031(6) 0.027(5) 0.053(7) 0.001(5) 0.005(5) 0.002(5) C9C 0.028(6) 0.041(6) 0.064(8) 0.002(6) 0.001(6) -0.007(5) C10C 0.051(7) 0.034(6) 0.061(8) 0.011(6) 0.004(6) -0.002(5) C11C 0.050(8) 0.052(8) 0.056(8) -0.006(6) 0.011(6) -0.005(6) C12C 0.040(6) 0.027(6) 0.064(8) 0.008(5) 0.007(6) 0.000(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 Br1 2.7171(13) . ? I1 Br2 2.7610(14) . ? I2 Br3 2.7125(14) . ? I2 Br4 2.7382(14) . ? I3 Br6 2.7468(11) . ? I3 Br5 2.8052(13) . ? S1A S1A' 1.403(7) . ? S1A C6A 1.661(11) . ? S1A' C7A 1.648(12) . ? N1A C2A 1.338(12) . ? N1A C3A 1.352(13) . ? N3A C6A 1.334(12) . ? N3A C7A 1.356(12) . ? N4A C10A 1.350(13) . ? N4A C11A 1.359(13) . ? C1A C2A 1.382(13) . ? C1A C5A 1.387(13) . ? C3A C4A 1.383(14) . ? C4A C5A 1.372(13) . ? C5A C6A 1.460(13) . ? C7A C8A 1.440(13) . ? C8A C9A 1.387(14) . ? C8A C12A 1.396(13) . ? C9A C10A 1.392(14) . ? C11A C12A 1.378(13) . ? S1B S1B' 1.329(7) . ? S1B C6B 1.663(11) . ? S1B' C7B 1.632(11) . ? N1B C2B 1.332(12) . ? N1B C3B 1.357(13) . ? N3B C7B 1.333(13) . ? N3B C6B 1.371(12) . ? N4B C11B 1.341(13) . ? N4B C10B 1.344(13) . ? C1B C2B 1.368(14) . ? C1B C5B 1.377(13) . ? C3B C4B 1.394(13) . ? C4B C5B 1.385(13) . ? C5B C6B 1.468(13) . ? C7B C8B 1.477(14) . ? C8B C12B 1.387(14) . ? C8B C9B 1.413(14) . ? C9B C10B 1.406(14) . ? C11B C12B 1.394(14) . ? S1C S1C' 1.405(7) . ? S1C C6C 1.643(12) . ? S1C' C7C 1.632(12) . ? N1C C2C 1.329(13) . ? N1C C3C 1.357(13) . ? N3C C7C 1.335(12) . ? N3C C6C 1.344(12) . ? N4C C11C 1.356(14) . ? N4C C10C 1.370(14) . ? C1C C2C 1.359(14) . ? C1C C5C 1.390(14) . ? C3C C4C 1.348(14) . ? C4C C5C 1.380(14) . ? C5C C6C 1.486(14) . ? C7C C8C 1.458(13) . ? C8C C9C 1.367(14) . ? C8C C12C 1.381(14) . ? C9C C10C 1.415(15) . ? C11C C12C 1.380(14) . ? 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 Br1 I1 Br2 179.09(4) . . ? Br3 I2 Br4 174.55(5) . . ? Br6 I3 Br5 178.49(5) . . ? S1A' S1A C6A 103.6(5) . . ? S1A S1A' C7A 104.2(5) . . ? C2A N1A C3A 119.1(9) . . ? C6A N3A C7A 109.7(8) . . ? C10A N4A C11A 120.9(9) . . ? C2A C1A C5A 118.7(9) . . ? N1A C2A C1A 122.3(10) . . ? N1A C3A C4A 120.8(10) . . ? C5A C4A C3A 120.1(10) . . ? C4A C5A C1A 118.8(9) . . ? C4A C5A C6A 122.3(9) . . ? C1A C5A C6A 118.8(9) . . ? N3A C6A C5A 123.2(9) . . ? N3A C6A S1A 111.4(7) . . ? C5A C6A S1A 125.4(8) . . ? N3A C7A C8A 122.8(9) . . ? N3A C7A S1A' 111.0(8) . . ? C8A C7A S1A' 126.2(8) . . ? C9A C8A C12A 117.8(9) . . ? C9A C8A C7A 122.5(9) . . ? C12A C8A C7A 119.7(9) . . ? C8A C9A C10A 121.0(10) . . ? N4A C10A C9A 119.5(9) . . ? N4A C11A C12A 120.6(10) . . ? C11A C12A C8A 120.0(9) . . ? S1B' S1B C6B 103.2(5) . . ? S1B S1B' C7B 106.4(5) . . ? C2B N1B C3B 120.0(9) . . ? C7B N3B C6B 106.8(8) . . ? C11B N4B C10B 120.6(9) . . ? C2B C1B C5B 120.8(9) . . ? N1B C2B C1B 121.1(10) . . ? N1B C3B C4B 120.6(10) . . ? C5B C4B C3B 119.3(10) . . ? C1B C5B C4B 118.2(9) . . ? C1B C5B C6B 121.1(9) . . ? C4B C5B C6B 120.6(9) . . ? N3B C6B C5B 120.9(9) . . ? N3B C6B S1B 111.4(7) . . ? C5B C6B S1B 127.6(8) . . ? N3B C7B C8B 120.5(9) . . ? N3B C7B S1B' 112.2(8) . . ? C8B C7B S1B' 127.3(9) . . ? C12B C8B C9B 118.4(9) . . ? C12B C8B C7B 121.2(9) . . ? C9B C8B C7B 120.4(9) . . ? C10B C9B C8B 119.7(10) . . ? N4B C10B C9B 120.1(9) . . ? N4B C11B C12B 122.3(10) . . ? C8B C12B C11B 118.9(9) . . ? S1C' S1C C6C 101.5(5) . . ? S1C S1C' C7C 105.4(5) . . ? C2C N1C C3C 118.2(9) . . ? C7C N3C C6C 108.4(9) . . ? C11C N4C C10C 117.6(9) . . ? C2C C1C C5C 118.8(10) . . ? N1C C2C C1C 122.9(11) . . ? C4C C3C N1C 121.8(10) . . ? C3C C4C C5C 120.0(11) . . ? C4C C5C C1C 118.2(10) . . ? C4C C5C C6C 120.9(10) . . ? C1C C5C C6C 120.9(9) . . ? N3C C6C C5C 123.1(10) . . ? N3C C6C S1C 113.0(8) . . ? C5C C6C S1C 123.8(8) . . ? N3C C7C C8C 122.5(10) . . ? N3C C7C S1C' 111.3(7) . . ? C8C C7C S1C' 126.2(8) . . ? C9C C8C C12C 119.9(10) . . ? C9C C8C C7C 120.1(10) . . ? C12C C8C C7C 119.9(9) . . ? C8C C9C C10C 119.0(11) . . ? N4C C10C C9C 121.3(10) . . ? N4C C11C C12C 122.9(11) . . ? C11C C12C C8C 119.2(10) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.997 _refine_diff_density_min -0.976 _refine_diff_density_rms 0.180 # Attachment 'web_deposit_cif_file_5_FrancescoDemartin_1328621263.L12I2.cif' data_L12I2 _database_code_depnum_ccdc_archive 'CCDC 866001' #TrackingRef 'web_deposit_cif_file_5_FrancescoDemartin_1328621263.L12I2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 I4 N4 S' _chemical_formula_weight 747.88 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' 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' _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 10.406(3) _cell_length_b 17.329(4) _cell_length_c 10.443(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.05(3) _cell_angle_gamma 90.00 _cell_volume 1859.7(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.92 _cell_measurement_theta_max 12.73 _exptl_crystal_description prism _exptl_crystal_colour 'dark brown' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 6.813 _exptl_absorpt_correction_type semiempirical _exptl_absorpt_correction_T_min 0.810 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details psi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'ENRAF NONIUS CAD4 DIFFRACTOMETER' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count 100 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2015 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 26.91 _reflns_number_total 2015 _reflns_number_gt 1272 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0230P)^2^+1.3632P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2015 _refine_ls_number_parameters 98 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0617 _refine_ls_wR_factor_gt 0.0531 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.006 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 0.23731(4) 0.11310(2) 0.89294(3) 0.05180(13) Uani 1 1 d . . . I2 I 0.32758(5) 0.01680(3) 1.09812(4) 0.07048(17) Uani 1 1 d . . . S S 0.0225(3) 0.09503(17) 0.3221(3) 0.0766(15) Uani 0.491(14) 1 d P . . N1 N 0.1552(4) 0.2011(3) 0.7078(4) 0.0515(12) Uani 1 1 d . . . N2 N 0.0225(3) 0.09503(17) 0.3221(3) 0.0766(15) Uani 0.51(2) 1 d P . . N3 N 0.0000 0.2302(4) 0.2500 0.0422(15) Uani 1 2 d S . . C1 C 0.1122(5) 0.1722(4) 0.5902(5) 0.0479(14) Uani 1 1 d . . . H1 H 0.1070 0.1190 0.5799 0.057 Uiso 1 1 calc R . . C2 C 0.1610(6) 0.2772(4) 0.7229(6) 0.0544(15) Uani 1 1 d . . . H2 H 0.1911 0.2973 0.8046 0.065 Uiso 1 1 calc R . . C3 C 0.1244(6) 0.3268(4) 0.6221(6) 0.0572(16) Uani 1 1 d . . . H3 H 0.1289 0.3799 0.6357 0.069 Uiso 1 1 calc R . . C4 C 0.0805(5) 0.2976(3) 0.5002(6) 0.0514(15) Uani 1 1 d . . . H4 H 0.0551 0.3307 0.4307 0.062 Uiso 1 1 calc R . . C5 C 0.0750(5) 0.2189(3) 0.4829(5) 0.0427(13) Uani 1 1 d . . . C6 C 0.0322(5) 0.1841(3) 0.3537(5) 0.0442(13) 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 0.0592(2) 0.0565(2) 0.03843(19) -0.00498(18) 0.00371(15) -0.0023(2) I2 0.1052(4) 0.0517(3) 0.0499(3) 0.0036(2) -0.0022(2) -0.0003(3) S 0.103(3) 0.065(2) 0.0562(18) 0.0199(13) -0.0066(14) 0.0053(16) N1 0.053(3) 0.063(3) 0.037(3) 0.003(2) 0.003(2) 0.005(3) N2 0.103(3) 0.065(2) 0.0562(18) 0.0199(13) -0.0066(14) 0.0053(16) N3 0.047(4) 0.040(4) 0.039(4) 0.000 0.003(3) 0.000 C1 0.051(4) 0.048(3) 0.042(3) -0.001(3) 0.001(3) 0.003(3) C2 0.055(4) 0.063(4) 0.044(3) -0.011(3) 0.002(3) 0.003(3) C3 0.071(4) 0.055(4) 0.044(3) -0.004(3) 0.005(3) 0.007(3) C4 0.051(4) 0.055(4) 0.046(3) 0.003(3) 0.004(3) 0.008(3) C5 0.034(3) 0.051(4) 0.043(3) 0.003(3) 0.002(2) 0.001(3) C6 0.041(3) 0.054(4) 0.037(3) 0.001(3) 0.003(2) 0.000(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 N1 2.505(5) . ? I1 I2 2.7613(10) . ? S N2 1.505(5) 2 ? S S 1.505(5) 2 ? S C6 1.578(6) . ? N1 C2 1.328(7) . ? N1 C1 1.336(7) . ? N3 C6 1.345(6) 2 ? N3 C6 1.345(6) . ? C1 C5 1.386(7) . ? C2 C3 1.366(8) . ? C3 C4 1.379(8) . ? C4 C5 1.377(7) . ? C5 C6 1.481(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 N1 I1 I2 179.65(12) . . ? N2 S S 0.0(3) 2 2 ? N2 S C6 102.0(2) 2 . ? S S C6 102.0(2) 2 . ? C2 N1 C1 118.9(5) . . ? C2 N1 I1 120.6(4) . . ? C1 N1 I1 120.4(4) . . ? C6 N3 C6 107.1(6) 2 . ? N1 C1 C5 122.4(6) . . ? N1 C2 C3 122.1(6) . . ? C2 C3 C4 119.4(6) . . ? C5 C4 C3 119.0(6) . . ? C4 C5 C1 118.1(5) . . ? C4 C5 C6 121.6(5) . . ? C1 C5 C6 120.3(5) . . ? N3 C6 C5 119.5(5) . . ? N3 C6 S 114.4(4) . . ? C5 C6 S 126.1(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.91 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.526 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.129