Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Prof. Vito Lippolis' _publ_contact_author_email lippolis@unica.it loop_ _publ_author_name 'Vito Lippolis' 'M. Carla Aragoni' 'Massimiliano Arca' 'Francesco Demartin' 'F. A. Devillanova' 'Alessandra Garau' 'Francesco Isaia' 'Gaetano Verani' data_da027 _database_code_depnum_ccdc_archive 'CCDC 265084' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Br I N2 S' _chemical_formula_weight 385.06 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 7.221(2) _cell_length_b 9.820(2) _cell_length_c 17.157(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.60(2) _cell_angle_gamma 90.00 _cell_volume 1210.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.02 _cell_measurement_theta_max 12.47 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.112 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 6.082 _exptl_absorpt_correction_type semiempirical _exptl_absorpt_correction_T_min 0.610 _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 'CAD4 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 2514 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2129 _reflns_number_gt 1630 _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^)+(0.0457P)^2^+1.2878P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2129 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0793 _refine_ls_wR_factor_gt 0.0715 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 I I 0.44640(5) 0.05501(3) 0.851067(17) 0.05486(14) Uani 1 1 d . . . Br Br 0.13319(10) -0.02960(7) 0.75978(4) 0.0843(2) Uani 1 1 d . . . S S 0.7438(2) 0.10691(14) 0.94505(9) 0.0700(4) Uani 1 1 d . . . N1 N 0.7254(5) 0.3608(4) 1.00593(19) 0.0429(8) Uani 1 1 d . . . N2 N 0.7958(5) 0.3602(4) 0.88501(19) 0.0444(8) Uani 1 1 d . . . C1 C 0.7525(6) 0.2805(5) 0.9446(3) 0.0472(10) Uani 1 1 d . . . C2 C 0.7546(5) 0.4952(5) 0.9858(2) 0.0385(9) Uani 1 1 d . . . C3 C 0.7519(6) 0.6146(5) 1.0284(3) 0.0460(10) Uani 1 1 d . . . H3 H 0.7233 0.6150 1.0801 0.055 Uiso 1 1 calc R . . C4 C 0.7938(6) 0.7332(5) 0.9905(3) 0.0526(11) Uani 1 1 d . . . H4 H 0.7929 0.8156 1.0172 0.063 Uiso 1 1 calc R . . C5 C 0.8374(6) 0.7320(5) 0.9131(3) 0.0495(11) Uani 1 1 d . . . H5 H 0.8659 0.8137 0.8896 0.059 Uiso 1 1 calc R . . C6 C 0.8397(6) 0.6141(5) 0.8706(3) 0.0462(10) Uani 1 1 d . . . H6 H 0.8670 0.6140 0.8187 0.055 Uiso 1 1 calc R . . C7 C 0.7990(6) 0.4946(5) 0.9088(2) 0.0392(9) Uani 1 1 d . . . C8 C 0.8473(8) 0.3132(6) 0.8087(3) 0.0654(14) Uani 1 1 d . . . H8A H 0.8564 0.2157 0.8089 0.078 Uiso 1 1 calc R . . H8B H 0.9651 0.3518 0.7992 0.078 Uiso 1 1 calc R . . H8C H 0.7540 0.3414 0.7682 0.078 Uiso 1 1 calc R . . C9 C 0.6795(7) 0.3139(6) 1.0828(3) 0.0562(12) Uani 1 1 d . . . H9A H 0.6116 0.2299 1.0769 0.067 Uiso 1 1 calc R . . H9B H 0.6048 0.3813 1.1055 0.067 Uiso 1 1 calc R . . H9C H 0.7921 0.2998 1.1164 0.067 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 0.0798(2) 0.03795(18) 0.0506(2) -0.00145(14) 0.02578(15) -0.00471(16) Br 0.0901(5) 0.0886(5) 0.0728(4) 0.0063(3) 0.0005(3) -0.0149(4) S 0.0963(11) 0.0368(7) 0.0745(9) 0.0066(6) -0.0044(8) -0.0033(7) N1 0.044(2) 0.044(2) 0.0416(18) 0.0049(16) 0.0047(15) -0.0009(17) N2 0.054(2) 0.039(2) 0.0396(18) -0.0003(16) 0.0006(16) 0.0009(17) C1 0.050(3) 0.040(2) 0.050(2) 0.007(2) -0.0010(19) -0.004(2) C2 0.034(2) 0.037(2) 0.044(2) 0.0038(19) 0.0031(17) -0.0011(18) C3 0.043(2) 0.050(3) 0.045(2) -0.002(2) 0.0050(19) 0.005(2) C4 0.050(3) 0.042(3) 0.067(3) -0.009(2) 0.008(2) 0.002(2) C5 0.046(3) 0.040(3) 0.063(3) 0.008(2) 0.008(2) 0.002(2) C6 0.049(3) 0.046(3) 0.045(2) 0.004(2) 0.0061(19) 0.001(2) C7 0.040(2) 0.038(2) 0.040(2) 0.0016(19) 0.0020(17) 0.0013(19) C8 0.096(4) 0.055(3) 0.047(3) -0.008(2) 0.014(3) 0.001(3) C9 0.055(3) 0.060(3) 0.055(3) 0.015(2) 0.013(2) -0.005(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 I S 2.6072(17) . ? I Br 2.7509(10) . ? S C1 1.706(5) . ? N1 C1 1.344(6) . ? N1 C2 1.386(6) . ? N1 C9 1.465(5) . ? N2 C1 1.348(5) . ? N2 C7 1.382(6) . ? N2 C8 1.469(5) . ? C2 C3 1.383(6) . ? C2 C7 1.388(6) . ? C3 C4 1.382(7) . ? C4 C5 1.394(6) . ? C5 C6 1.369(6) . ? C6 C7 1.390(6) . ? 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 S I Br 173.28(3) . . ? C1 S I 102.75(17) . . ? C1 N1 C2 109.0(3) . . ? C1 N1 C9 125.7(4) . . ? C2 N1 C9 125.2(4) . . ? C1 N2 C7 109.2(3) . . ? C1 N2 C8 126.2(4) . . ? C7 N2 C8 124.4(4) . . ? N1 C1 N2 108.4(4) . . ? N1 C1 S 125.0(3) . . ? N2 C1 S 126.5(4) . . ? C3 C2 N1 131.7(4) . . ? C3 C2 C7 121.5(4) . . ? N1 C2 C7 106.7(4) . . ? C4 C3 C2 116.8(4) . . ? C3 C4 C5 121.4(4) . . ? C6 C5 C4 122.0(4) . . ? C5 C6 C7 116.6(4) . . ? N2 C7 C2 106.7(4) . . ? N2 C7 C6 131.7(4) . . ? C2 C7 C6 121.6(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.780 _refine_diff_density_min -0.760 _refine_diff_density_rms 0.104 data_DEV132 _database_code_depnum_ccdc_archive 'CCDC 265085' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Br1.28 I0.72 N2 Se' _chemical_formula_weight 418.80 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' Se Se -0.0929 2.2259 '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 13.404(3) _cell_length_b 9.997(3) _cell_length_c 9.485(2) _cell_angle_alpha 90.00 _cell_angle_beta 108.840(10) _cell_angle_gamma 90.00 _cell_volume 1202.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.72 _cell_measurement_theta_max 13.42 _exptl_crystal_description prism _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 9.186 _exptl_absorpt_correction_type semiempirical _exptl_absorpt_correction_T_min 0.706 _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 'CAD4 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 1120 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 24.97 _reflns_number_total 1052 _reflns_number_gt 788 _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^)+(0.0280P)^2^+2.9900P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1052 _refine_ls_number_parameters 67 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0614 _refine_ls_wR_factor_gt 0.0565 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 I I -0.17655(3) 0.06713(4) 0.51907(5) 0.06148(18) Uani 0.361(18) 1 d P . . Br Br -0.17655(3) 0.06713(4) 0.51907(5) 0.06148(18) Uani 0.64(3) 1 d P . . Se Se 0.0000 0.06497(5) 0.7500 0.0524(2) Uani 1 2 d S . . N1 N 0.0642(2) 0.3313(3) 0.7023(4) 0.0375(8) Uani 1 1 d . . . C1 C 0.0000 0.2544(5) 0.7500 0.0388(13) Uani 1 2 d S . . C2 C 0.0411(3) 0.4647(3) 0.7199(4) 0.0354(9) Uani 1 1 d . . . C3 C 0.0839(3) 0.5836(4) 0.6888(5) 0.0449(10) Uani 1 1 d . . . H3 H 0.1388 0.5842 0.6491 0.054 Uiso 1 1 calc R . . C4 C 0.0411(3) 0.6985(4) 0.7197(5) 0.0557(12) Uani 1 1 d . . . H4 H 0.0673 0.7800 0.6998 0.067 Uiso 1 1 calc R . . C5 C 0.1476(3) 0.2861(4) 0.6457(5) 0.0523(11) Uani 1 1 d . . . H5A H 0.2137 0.2864 0.7250 0.063 Uiso 1 1 calc R . . H5B H 0.1517 0.3451 0.5679 0.063 Uiso 1 1 calc R . . H5C H 0.1322 0.1971 0.6068 0.063 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I 0.0652(3) 0.0497(3) 0.0802(3) -0.0146(2) 0.0383(2) -0.01048(19) Br 0.0652(3) 0.0497(3) 0.0802(3) -0.0146(2) 0.0383(2) -0.01048(19) Se 0.0641(4) 0.0226(3) 0.0874(5) 0.000 0.0477(4) 0.000 N1 0.0421(17) 0.0236(16) 0.056(2) 0.0013(14) 0.0281(16) 0.0025(13) C1 0.042(3) 0.025(3) 0.056(4) 0.000 0.025(3) 0.000 C2 0.038(2) 0.0267(19) 0.044(2) 0.0012(15) 0.0174(18) 0.0008(15) C3 0.045(2) 0.033(2) 0.062(3) 0.005(2) 0.025(2) -0.0040(18) C4 0.065(3) 0.028(2) 0.082(3) 0.006(2) 0.036(3) -0.006(2) C5 0.059(3) 0.040(2) 0.074(3) -0.001(2) 0.043(2) 0.006(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 I Se 2.6553(7) . ? Se C1 1.894(5) . ? Se Br 2.6553(7) 2_556 ? Se I 2.6553(7) 2_556 ? N1 C1 1.337(4) . ? N1 C2 1.391(4) . ? N1 C5 1.459(4) . ? C1 N1 1.337(4) 2_556 ? C2 C3 1.392(5) . ? C2 C2 1.394(7) 2_556 ? C3 C4 1.358(6) . ? C4 C4 1.397(8) 2_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Se Br 89.534(14) . 2_556 ? C1 Se I 89.534(14) . 2_556 ? Br Se I 0.00(2) 2_556 2_556 ? C1 Se I 89.534(14) . . ? Br Se I 179.07(3) 2_556 . ? I Se I 179.07(3) 2_556 . ? C1 N1 C2 108.5(3) . . ? C1 N1 C5 126.8(3) . . ? C2 N1 C5 124.6(3) . . ? N1 C1 N1 109.8(4) . 2_556 ? N1 C1 Se 125.1(2) . . ? N1 C1 Se 125.1(2) 2_556 . ? N1 C2 C3 132.1(3) . . ? N1 C2 C2 106.57(18) . 2_556 ? C3 C2 C2 121.4(2) . 2_556 ? C4 C3 C2 116.5(4) . . ? C3 C4 C4 122.2(2) . 2_556 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.375 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.075