Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Anca Silvestru' _publ_contact_author_address ; Faculty of Chemistry & Chemical Engineering Babes-Bolyai University Str. Arany Janos Nr. 11 Cluj-Napoca RO-400028 ROMANIA ; _publ_contact_author_email ANCAS@CHEM.UBBCLUJ.RO _publ_section_title ; Solid state structure and solution behaviour of organoselenium(II) compounds containing 2-{X(CH2CH2)2NCH2}C6H4 groups (X = O, NMe) ; _publ_author_address 'Arany Janos No11, Cluj-Napoca, 400028, Romania' loop_ _publ_author_name 'Silvestru Anca' 'Anca beleaga' 'Calin Deleanu' 'Monika Kulcsar' 'Alina Nicolescu' 'Cristian Silvestru' ; C.Todasca ; # Attachment 'Compound 3 - CCDC 608159.cif' data_157rich _database_code_depnum_ccdc_archive 'CCDC 608159' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 Cl N O Se' _chemical_formula_sum 'C11 H14 Cl N O Se' _chemical_formula_weight 290.64 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.476(2) _cell_length_b 8.939(2) _cell_length_c 15.576(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1180.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 5345 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 28.04 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.31 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 3.381 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2691 _exptl_absorpt_correction_T_max 0.3489 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9422 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0394 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 26.36 _reflns_number_total 2418 _reflns_number_gt 2358 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0054P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.019(8) _refine_ls_number_reflns 2418 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0227 _refine_ls_wR_factor_ref 0.0522 _refine_ls_wR_factor_gt 0.0519 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6958(2) 0.2003(3) 0.14758(15) 0.0286(5) Uani 1 1 d . . . C2 C 0.6016(3) 0.1008(3) 0.10248(16) 0.0332(5) Uani 1 1 d . . . C3 C 0.4452(3) 0.0800(3) 0.12800(18) 0.0426(7) Uani 1 1 d . . . H3 H 0.3814 0.0129 0.0984 0.051 Uiso 1 1 calc R . . C4 C 0.3853(3) 0.1577(3) 0.1964(2) 0.0490(7) Uani 1 1 d . . . H4 H 0.2809 0.1442 0.2129 0.059 Uiso 1 1 calc R . . C5 C 0.4802(4) 0.2558(3) 0.24066(19) 0.0489(8) Uani 1 1 d . . . H5 H 0.4392 0.3083 0.2872 0.059 Uiso 1 1 calc R . . C6 C 0.6361(3) 0.2777(3) 0.21693(17) 0.0390(6) Uani 1 1 d . . . H6 H 0.6997 0.3438 0.2474 0.047 Uiso 1 1 calc R . . C7 C 0.6729(3) 0.0260(3) 0.02577(19) 0.0402(6) Uani 1 1 d . . . H7A H 0.6247 -0.0713 0.0171 0.048 Uiso 1 1 calc R . . H7B H 0.6545 0.0860 -0.0252 0.048 Uiso 1 1 calc R . . C8 C 0.9289(4) -0.0076(3) -0.04215(16) 0.0411(6) Uani 1 1 d . . . H8A H 0.9130 0.0814 -0.0767 0.049 Uiso 1 1 calc R . . H8B H 0.8864 -0.0924 -0.0734 0.049 Uiso 1 1 calc R . . C9 C 1.1028(4) -0.0307(3) -0.02739(19) 0.0454(7) Uani 1 1 d . . . H9A H 1.1554 -0.0429 -0.0822 0.054 Uiso 1 1 calc R . . H9B H 1.1465 0.0570 0.0005 0.054 Uiso 1 1 calc R . . C10 C 1.0559(3) -0.1418(3) 0.10581(18) 0.0371(6) Uani 1 1 d . . . H10A H 1.0998 -0.0555 0.1351 0.045 Uiso 1 1 calc R . . H10B H 1.0769 -0.2293 0.1408 0.045 Uiso 1 1 calc R . . C11 C 0.8798(3) -0.1218(3) 0.09664(17) 0.0339(5) Uani 1 1 d . . . H11A H 0.8340 -0.2115 0.0721 0.041 Uiso 1 1 calc R . . H11B H 0.8331 -0.1062 0.1528 0.041 Uiso 1 1 calc R . . Cl1 Cl 0.95888(9) 0.45750(7) 0.17494(5) 0.04732(18) Uani 1 1 d . . . N1 N 0.8442(2) 0.0088(2) 0.04042(13) 0.0302(5) Uani 1 1 d . . . O1 O 1.1317(2) -0.1589(2) 0.02453(13) 0.0470(5) Uani 1 1 d . . . Se1 Se 0.90816(3) 0.22009(3) 0.104533(15) 0.03006(8) 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 C1 0.0226(11) 0.0285(13) 0.0346(12) 0.0058(10) 0.0007(9) -0.0013(9) C2 0.0293(12) 0.0294(12) 0.0409(13) 0.0012(11) -0.0064(13) 0.0007(10) C3 0.0359(15) 0.0355(14) 0.0563(18) 0.0039(12) -0.0096(12) -0.0064(11) C4 0.0288(16) 0.0499(16) 0.068(2) 0.0077(15) 0.0086(13) -0.0025(13) C5 0.0433(15) 0.055(2) 0.0484(16) -0.0055(14) 0.0152(13) -0.0009(14) C6 0.0371(13) 0.0430(14) 0.0368(13) -0.0069(12) 0.0037(10) -0.0076(12) C7 0.0359(14) 0.0389(15) 0.0460(16) -0.0072(12) -0.0147(12) 0.0040(12) C8 0.0539(18) 0.0364(14) 0.0330(13) -0.0018(11) 0.0030(13) 0.0051(13) C9 0.0534(17) 0.0370(14) 0.0458(15) 0.0015(12) 0.0165(15) 0.0040(14) C10 0.0342(14) 0.0305(13) 0.0468(14) 0.0027(12) -0.0016(12) 0.0033(10) C11 0.0342(13) 0.0264(12) 0.0412(14) 0.0011(11) -0.0015(11) -0.0035(9) Cl1 0.0542(4) 0.0396(4) 0.0482(4) -0.0127(3) 0.0126(3) -0.0172(3) N1 0.0320(11) 0.0280(11) 0.0306(11) -0.0033(9) -0.0035(9) 0.0021(9) O1 0.0471(11) 0.0382(10) 0.0556(12) -0.0022(9) 0.0111(9) 0.0117(9) Se1 0.02811(12) 0.02936(12) 0.03270(12) -0.00070(10) 0.00346(10) -0.00272(10) _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 C1 C6 1.379(3) . ? C1 C2 1.386(3) . ? C1 Se1 1.929(2) . ? C2 C3 1.397(3) . ? C2 C7 1.496(4) . ? C3 C4 1.370(4) . ? C4 C5 1.375(4) . ? C5 C6 1.386(4) . ? C7 N1 1.478(3) . ? C8 N1 1.480(3) . ? C8 C9 1.506(4) . ? C9 O1 1.423(3) . ? C10 O1 1.428(3) . ? C10 C11 1.511(3) . ? C11 N1 1.490(3) . ? Cl1 Se1 2.4270(8) . ? N1 Se1 2.204(2) . ? 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 C1 C2 120.5(2) . . ? C6 C1 Se1 124.65(18) . . ? C2 C1 Se1 114.83(18) . . ? C1 C2 C3 119.2(2) . . ? C1 C2 C7 117.3(2) . . ? C3 C2 C7 123.4(2) . . ? C4 C3 C2 120.4(2) . . ? C3 C4 C5 119.8(2) . . ? C4 C5 C6 120.9(3) . . ? C1 C6 C5 119.2(3) . . ? N1 C7 C2 108.6(2) . . ? N1 C8 C9 110.9(2) . . ? O1 C9 C8 111.4(2) . . ? O1 C10 C11 111.9(2) . . ? N1 C11 C10 110.39(19) . . ? C7 N1 C8 110.7(2) . . ? C7 N1 C11 111.8(2) . . ? C8 N1 C11 109.53(19) . . ? C7 N1 Se1 102.87(15) . . ? C8 N1 Se1 111.06(15) . . ? C11 N1 Se1 110.80(14) . . ? C9 O1 C10 109.88(19) . . ? C1 Se1 N1 81.33(9) . . ? C1 Se1 Cl1 95.07(8) . . ? N1 Se1 Cl1 175.92(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.1(4) . . . . ? Se1 C1 C2 C3 -179.24(18) . . . . ? C6 C1 C2 C7 177.5(2) . . . . ? Se1 C1 C2 C7 -1.9(3) . . . . ? C1 C2 C3 C4 0.5(4) . . . . ? C7 C2 C3 C4 -176.7(3) . . . . ? C2 C3 C4 C5 -0.6(4) . . . . ? C3 C4 C5 C6 0.2(5) . . . . ? C2 C1 C6 C5 -0.6(4) . . . . ? Se1 C1 C6 C5 178.7(2) . . . . ? C4 C5 C6 C1 0.4(4) . . . . ? C1 C2 C7 N1 30.7(3) . . . . ? C3 C2 C7 N1 -152.1(2) . . . . ? N1 C8 C9 O1 58.1(3) . . . . ? O1 C10 C11 N1 -56.8(3) . . . . ? C2 C7 N1 C8 -157.8(2) . . . . ? C2 C7 N1 C11 79.8(3) . . . . ? C2 C7 N1 Se1 -39.1(2) . . . . ? C9 C8 N1 C7 -178.0(2) . . . . ? C9 C8 N1 C11 -54.3(3) . . . . ? C9 C8 N1 Se1 68.4(2) . . . . ? C10 C11 N1 C7 176.5(2) . . . . ? C10 C11 N1 C8 53.5(3) . . . . ? C10 C11 N1 Se1 -69.4(2) . . . . ? C8 C9 O1 C10 -59.5(3) . . . . ? C11 C10 O1 C9 59.3(3) . . . . ? C6 C1 Se1 N1 163.6(2) . . . . ? C2 C1 Se1 N1 -17.04(17) . . . . ? C6 C1 Se1 Cl1 -18.3(2) . . . . ? C2 C1 Se1 Cl1 161.02(17) . . . . ? C7 N1 Se1 C1 31.69(17) . . . . ? C8 N1 Se1 C1 150.10(17) . . . . ? C11 N1 Se1 C1 -87.93(16) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.389 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.051 # Attachment 'Compound 6 - CCDC 608160.cif' data_227rich _database_code_depnum_ccdc_archive 'CCDC 608160' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H17 I N2 Se' _chemical_formula_sum 'C12 H17 I N2 Se' _chemical_formula_weight 395.14 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.8591(13) _cell_length_b 15.772(3) _cell_length_c 11.3391(19) _cell_angle_alpha 90.00 _cell_angle_beta 96.523(3) _cell_angle_gamma 90.00 _cell_volume 1396.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3145 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 22.83 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.879 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 4.878 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4023 _exptl_absorpt_correction_T_max 0.4807 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14655 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2850 _reflns_number_gt 2543 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0462P)^2^+0.7398P] 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 2850 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1170 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 1.264 _refine_ls_restrained_S_all 1.264 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0443(7) 0.6505(4) 0.2693(5) 0.0328(13) Uani 1 1 d . . . C2 C 1.1003(8) 0.7229(4) 0.3329(5) 0.0383(14) Uani 1 1 d . . . C3 C 1.2622(8) 0.7529(4) 0.3195(6) 0.0467(17) Uani 1 1 d . . . H3 H 1.3025 0.8007 0.3619 0.056 Uiso 1 1 calc R . . C4 C 1.3650(9) 0.7146(5) 0.2459(6) 0.0518(18) Uani 1 1 d . . . H4 H 1.4735 0.7361 0.2388 0.062 Uiso 1 1 calc R . . C5 C 1.3081(8) 0.6454(5) 0.1836(6) 0.0475(16) Uani 1 1 d . . . H5 H 1.3781 0.6197 0.1331 0.057 Uiso 1 1 calc R . . C6 C 1.1460(8) 0.6115(4) 0.1934(6) 0.0415(15) Uani 1 1 d . . . H6 H 1.1074 0.5638 0.1500 0.050 Uiso 1 1 calc R . . C7 C 0.9785(9) 0.7641(4) 0.4061(6) 0.0465(16) Uani 1 1 d . . . H7A H 1.0413 0.7959 0.4703 0.056 Uiso 1 1 calc R . . H7B H 0.9055 0.8033 0.3577 0.056 Uiso 1 1 calc R . . C8 C 0.9687(9) 0.6553(4) 0.5579(6) 0.0468(16) Uani 1 1 d . . . H8A H 1.0089 0.6969 0.6177 0.056 Uiso 1 1 calc R . . H8B H 1.0679 0.6267 0.5329 0.056 Uiso 1 1 calc R . . C9 C 0.8549(9) 0.5912(4) 0.6107(6) 0.0531(18) Uani 1 1 d . . . H9A H 0.8251 0.5464 0.5535 0.064 Uiso 1 1 calc R . . H9B H 0.9174 0.5659 0.6806 0.064 Uiso 1 1 calc R . . C10 C 0.6063(9) 0.6672(4) 0.5368(6) 0.0513(17) Uani 1 1 d . . . H10A H 0.4996 0.6917 0.5558 0.062 Uiso 1 1 calc R . . H10B H 0.5794 0.6233 0.4777 0.062 Uiso 1 1 calc R . . C11 C 0.7137(8) 0.7348(4) 0.4876(6) 0.0419(15) Uani 1 1 d . . . H11A H 0.6501 0.7602 0.4182 0.050 Uiso 1 1 calc R . . H11B H 0.7397 0.7789 0.5465 0.050 Uiso 1 1 calc R . . C12 C 0.5918(13) 0.5688(5) 0.6969(8) 0.083(3) Uani 1 1 d . . . H12A H 0.5831 0.5180 0.6501 0.124 Uiso 1 1 calc R . . H12B H 0.4796 0.5922 0.7001 0.124 Uiso 1 1 calc R . . H12C H 0.6426 0.5559 0.7758 0.124 Uiso 1 1 calc R . . I1 I 0.75612(6) 0.51405(3) 0.09694(4) 0.05278(19) Uani 1 1 d . . . N1 N 0.8735(6) 0.6985(3) 0.4550(4) 0.0344(11) Uani 1 1 d . . . N2 N 0.6986(8) 0.6304(3) 0.6431(5) 0.0519(15) Uani 1 1 d . . . Se1 Se 0.81960(8) 0.61071(4) 0.29516(5) 0.03546(19) 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 C1 0.034(3) 0.035(3) 0.029(3) 0.007(2) 0.001(2) 0.001(3) C2 0.042(4) 0.038(3) 0.035(3) 0.002(3) 0.001(3) -0.001(3) C3 0.044(4) 0.043(4) 0.051(4) 0.007(3) -0.008(3) -0.014(3) C4 0.037(4) 0.069(5) 0.048(4) 0.009(4) 0.001(3) -0.007(4) C5 0.040(4) 0.060(5) 0.043(4) 0.005(3) 0.007(3) 0.009(3) C6 0.038(4) 0.042(4) 0.044(4) -0.004(3) 0.003(3) 0.001(3) C7 0.064(4) 0.035(3) 0.041(4) -0.006(3) 0.010(3) -0.012(3) C8 0.048(4) 0.048(4) 0.043(4) 0.000(3) -0.003(3) 0.006(3) C9 0.061(5) 0.053(4) 0.044(4) 0.011(3) 0.002(3) 0.013(4) C10 0.058(5) 0.045(4) 0.052(4) -0.005(3) 0.010(4) 0.012(3) C11 0.051(4) 0.036(3) 0.038(3) -0.003(3) 0.004(3) 0.009(3) C12 0.103(7) 0.071(6) 0.083(6) 0.022(5) 0.043(6) 0.000(5) I1 0.0568(3) 0.0547(3) 0.0478(3) -0.0223(2) 0.0103(2) -0.0150(2) N1 0.039(3) 0.038(3) 0.026(2) -0.006(2) -0.003(2) 0.006(2) N2 0.070(4) 0.043(3) 0.046(3) 0.001(3) 0.022(3) 0.012(3) Se1 0.0348(3) 0.0374(4) 0.0345(3) -0.0040(2) 0.0058(3) -0.0011(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 C1 C6 1.384(8) . ? C1 C2 1.394(8) . ? C1 Se1 1.928(6) . ? C2 C3 1.383(9) . ? C2 C7 1.486(9) . ? C3 C4 1.367(9) . ? C3 H3 0.9300 . ? C4 C5 1.349(9) . ? C4 H4 0.9300 . ? C5 C6 1.398(9) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.471(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.479(7) . ? C8 C9 1.516(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.459(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N2 1.455(9) . ? C10 C11 1.505(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N1 1.465(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N2 1.461(9) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? I1 Se1 2.7148(8) . ? N1 Se1 2.282(4) . ? 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 C1 C2 121.0(6) . . ? C6 C1 Se1 123.6(5) . . ? C2 C1 Se1 115.4(4) . . ? C3 C2 C1 117.6(6) . . ? C3 C2 C7 124.8(6) . . ? C1 C2 C7 117.5(5) . . ? C4 C3 C2 122.0(6) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C5 C4 C3 119.6(7) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 121.2(6) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.4(6) . . ? C1 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? N1 C7 C2 109.1(5) . . ? N1 C7 H7A 109.9 . . ? C2 C7 H7A 109.9 . . ? N1 C7 H7B 109.9 . . ? C2 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? N1 C8 C9 110.5(5) . . ? N1 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? N1 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N2 C9 C8 111.6(6) . . ? N2 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? N2 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? N2 C10 C11 110.0(6) . . ? N2 C10 H10A 109.7 . . ? C11 C10 H10A 109.7 . . ? N2 C10 H10B 109.7 . . ? C11 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? N1 C11 C10 110.5(5) . . ? N1 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? N1 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 N1 C7 110.7(5) . . ? C11 N1 C8 110.6(5) . . ? C7 N1 C8 111.5(5) . . ? C11 N1 Se1 110.5(4) . . ? C7 N1 Se1 100.9(3) . . ? C8 N1 Se1 112.2(4) . . ? C10 N2 C9 108.4(5) . . ? C10 N2 C12 110.8(7) . . ? C9 N2 C12 111.3(6) . . ? C1 Se1 N1 80.4(2) . . ? C1 Se1 I1 98.18(17) . . ? N1 Se1 I1 176.76(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.4(9) . . . . ? Se1 C1 C2 C3 178.6(4) . . . . ? C6 C1 C2 C7 176.0(6) . . . . ? Se1 C1 C2 C7 -4.0(7) . . . . ? C1 C2 C3 C4 0.7(9) . . . . ? C7 C2 C3 C4 -176.4(6) . . . . ? C2 C3 C4 C5 0.2(10) . . . . ? C3 C4 C5 C6 -0.5(10) . . . . ? C2 C1 C6 C5 1.2(9) . . . . ? Se1 C1 C6 C5 -178.9(5) . . . . ? C4 C5 C6 C1 -0.2(10) . . . . ? C3 C2 C7 N1 -148.2(6) . . . . ? C1 C2 C7 N1 34.7(8) . . . . ? N1 C8 C9 N2 -55.7(7) . . . . ? N2 C10 C11 N1 61.0(7) . . . . ? C10 C11 N1 C7 179.6(5) . . . . ? C10 C11 N1 C8 -56.3(6) . . . . ? C10 C11 N1 Se1 68.7(5) . . . . ? C2 C7 N1 C11 -158.2(5) . . . . ? C2 C7 N1 C8 78.1(6) . . . . ? C2 C7 N1 Se1 -41.2(5) . . . . ? C9 C8 N1 C11 53.4(7) . . . . ? C9 C8 N1 C7 177.0(5) . . . . ? C9 C8 N1 Se1 -70.6(6) . . . . ? C11 C10 N2 C9 -61.5(7) . . . . ? C11 C10 N2 C12 176.1(6) . . . . ? C8 C9 N2 C10 59.5(7) . . . . ? C8 C9 N2 C12 -178.4(6) . . . . ? C6 C1 Se1 N1 163.8(5) . . . . ? C2 C1 Se1 N1 -16.3(4) . . . . ? C6 C1 Se1 I1 -19.2(5) . . . . ? C2 C1 Se1 I1 160.8(4) . . . . ? C11 N1 Se1 C1 149.5(4) . . . . ? C7 N1 Se1 C1 32.4(4) . . . . ? C8 N1 Se1 C1 -86.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.946 _refine_diff_density_min -0.943 _refine_diff_density_rms 0.144 # Attachment 'Compound_2_-_CCDC_608161_-_corrected.cif' data_231rich _database_code_depnum_ccdc_archive 'CCDC 608161' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H34 N4 Se2' _chemical_formula_sum 'C24 H34 N4 Se2' _chemical_formula_weight 536.47 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' Se Se -0.0929 2.2259 '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 ' _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 15.7733(13) _cell_length_b 9.5329(8) _cell_length_c 17.4030(14) _cell_angle_alpha 90.00 _cell_angle_beta 110.053(2) _cell_angle_gamma 90.00 _cell_volume 2458.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 4392 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 23.44 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 3.026 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3189 _exptl_absorpt_correction_T_max 0.5168 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19212 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0412 _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 -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5007 _reflns_number_gt 4136 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0458P)^2^+1.3171P] 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 5007 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _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 C1 C 1.0110(2) 0.1678(3) 0.2432(2) 0.0352(7) Uani 1 1 d . . . C2 C 1.1002(2) 0.1293(4) 0.2569(2) 0.0384(8) Uani 1 1 d . . . C3 C 1.1645(2) 0.1611(4) 0.3316(2) 0.0479(9) Uani 1 1 d . . . H3 H 1.2242 0.1355 0.3416 0.057 Uiso 1 1 calc R . . C4 C 1.1422(3) 0.2300(4) 0.3917(2) 0.0531(10) Uani 1 1 d . . . H4 H 1.1867 0.2513 0.4414 0.064 Uiso 1 1 calc R . . C5 C 1.0543(3) 0.2669(4) 0.3779(2) 0.0499(9) Uani 1 1 d . . . H5 H 1.0389 0.3122 0.4185 0.060 Uiso 1 1 calc R . . C6 C 0.9884(2) 0.2371(4) 0.3035(2) 0.0418(8) Uani 1 1 d . . . H6 H 0.9289 0.2635 0.2940 0.050 Uiso 1 1 calc R . . C7 C 1.1262(2) 0.0575(4) 0.1913(2) 0.0446(9) Uani 1 1 d . . . H7A H 1.1070 0.1149 0.1423 0.054 Uiso 1 1 calc R . . H7B H 1.1914 0.0494 0.2094 0.054 Uiso 1 1 calc R . . C8 C 1.1225(3) -0.1774(4) 0.2392(2) 0.0495(9) Uani 1 1 d . . . H8A H 1.1092 -0.1426 0.2862 0.059 Uiso 1 1 calc R . . H8B H 1.1876 -0.1823 0.2539 0.059 Uiso 1 1 calc R . . C9 C 1.0830(3) -0.3226(4) 0.2177(3) 0.0565(11) Uani 1 1 d . . . H9A H 1.1083 -0.3846 0.2641 0.068 Uiso 1 1 calc R . . H9B H 1.0182 -0.3188 0.2051 0.068 Uiso 1 1 calc R . . C11 C 1.1031(3) -0.1375(4) 0.0993(2) 0.0488(9) Uani 1 1 d . . . H11A H 1.1675 -0.1391 0.1095 0.059 Uiso 1 1 calc R . . H11B H 1.0752 -0.0766 0.0529 0.059 Uiso 1 1 calc R . . C10 C 1.0657(3) -0.2831(5) 0.0796(3) 0.0580(11) Uani 1 1 d . . . H10A H 1.0005 -0.2800 0.0648 0.070 Uiso 1 1 calc R . . H10B H 1.0794 -0.3185 0.0330 0.070 Uiso 1 1 calc R . . C12 C 1.0701(4) -0.5195(5) 0.1294(3) 0.0835(16) Uani 1 1 d . . . H12A H 1.0053 -0.5199 0.1109 0.125 Uiso 1 1 calc R . . H12B H 1.0933 -0.5761 0.1777 0.125 Uiso 1 1 calc R . . H12C H 1.0901 -0.5569 0.0873 0.125 Uiso 1 1 calc R . . C13 C 0.7165(2) 0.2355(4) 0.12384(19) 0.0370(8) Uani 1 1 d . . . C14 C 0.6581(3) 0.3185(4) 0.1489(2) 0.0445(9) Uani 1 1 d . . . C15 C 0.5764(3) 0.2603(5) 0.1473(3) 0.0569(11) Uani 1 1 d . . . H15 H 0.5365 0.3147 0.1634 0.068 Uiso 1 1 calc R . . C16 C 0.5537(3) 0.1249(5) 0.1226(3) 0.0653(12) Uani 1 1 d . . . H16 H 0.4990 0.0880 0.1223 0.078 Uiso 1 1 calc R . . C17 C 0.6118(3) 0.0439(4) 0.0984(3) 0.0575(11) Uani 1 1 d . . . H17 H 0.5965 -0.0482 0.0817 0.069 Uiso 1 1 calc R . . C18 C 0.6931(2) 0.0986(4) 0.0988(2) 0.0439(9) Uani 1 1 d . . . H18 H 0.7322 0.0434 0.0821 0.053 Uiso 1 1 calc R . . C19 C 0.6836(3) 0.4649(4) 0.1771(2) 0.0536(10) Uani 1 1 d . . . H19A H 0.6321 0.5127 0.1835 0.064 Uiso 1 1 calc R . . H19B H 0.7317 0.4636 0.2298 0.064 Uiso 1 1 calc R . . C20 C 0.7667(3) 0.6639(4) 0.1525(2) 0.0537(10) Uani 1 1 d . . . H20A H 0.8170 0.6377 0.2008 0.064 Uiso 1 1 calc R . . H20B H 0.7297 0.7309 0.1687 0.064 Uiso 1 1 calc R . . C21 C 0.8013(3) 0.7293(4) 0.0911(3) 0.0591(11) Uani 1 1 d . . . H21A H 0.8369 0.8115 0.1148 0.071 Uiso 1 1 calc R . . H21B H 0.8402 0.6633 0.0767 0.071 Uiso 1 1 calc R . . C23 C 0.6396(2) 0.5761(4) 0.0435(2) 0.0448(9) Uani 1 1 d . . . H23A H 0.5982 0.6390 0.0567 0.054 Uiso 1 1 calc R . . H23B H 0.6069 0.4918 0.0195 0.054 Uiso 1 1 calc R . . C22 C 0.6757(3) 0.6461(4) -0.0171(2) 0.0524(10) Uani 1 1 d . . . H22A H 0.7134 0.5804 -0.0333 0.063 Uiso 1 1 calc R . . H22B H 0.6257 0.6722 -0.0657 0.063 Uiso 1 1 calc R . . C24 C 0.7609(4) 0.8371(5) -0.0415(3) 0.0867(17) Uani 1 1 d . . . H24A H 0.7943 0.7703 -0.0611 0.130 Uiso 1 1 calc R . . H24B H 0.7996 0.9140 -0.0159 0.130 Uiso 1 1 calc R . . H24C H 0.7108 0.8714 -0.0866 0.130 Uiso 1 1 calc R . . N1 N 1.08654(19) -0.0812(3) 0.17160(17) 0.0396(7) Uani 1 1 d . . . N2 N 1.1027(2) -0.3768(3) 0.1478(2) 0.0540(8) Uani 1 1 d . . . N3 N 0.7137(2) 0.5406(3) 0.11755(17) 0.0404(7) Uani 1 1 d . . . N4 N 0.7277(2) 0.7696(3) 0.01778(19) 0.0527(8) Uani 1 1 d . . . Se1 Se 0.92173(2) 0.12238(4) 0.13868(2) 0.04549(13) Uani 1 1 d . . . Se2 Se 0.82600(2) 0.32069(4) 0.11909(2) 0.04267(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 C1 0.0325(17) 0.0335(18) 0.0370(18) -0.0010(14) 0.0087(14) -0.0039(14) C2 0.0378(19) 0.0326(18) 0.047(2) 0.0029(15) 0.0180(16) -0.0027(14) C3 0.0319(19) 0.050(2) 0.055(2) -0.0003(18) 0.0068(17) 0.0015(16) C4 0.049(2) 0.055(2) 0.044(2) -0.0074(19) 0.0016(18) 0.0011(19) C5 0.053(2) 0.054(2) 0.042(2) -0.0069(18) 0.0161(18) 0.0042(19) C6 0.0341(18) 0.047(2) 0.045(2) -0.0020(17) 0.0150(16) 0.0013(15) C7 0.040(2) 0.044(2) 0.058(2) 0.0005(18) 0.0269(18) 0.0009(16) C8 0.057(2) 0.047(2) 0.044(2) 0.0001(18) 0.0170(18) 0.0000(18) C9 0.067(3) 0.046(2) 0.059(3) 0.004(2) 0.026(2) -0.005(2) C11 0.057(2) 0.049(2) 0.047(2) -0.0015(18) 0.0254(19) 0.0035(18) C10 0.059(3) 0.065(3) 0.055(2) -0.017(2) 0.024(2) -0.005(2) C12 0.093(4) 0.052(3) 0.110(4) -0.024(3) 0.040(3) -0.020(3) C13 0.0327(18) 0.041(2) 0.0323(17) 0.0098(15) 0.0052(14) -0.0020(15) C14 0.051(2) 0.045(2) 0.038(2) 0.0077(17) 0.0152(17) 0.0070(17) C15 0.049(2) 0.065(3) 0.063(3) 0.014(2) 0.027(2) 0.013(2) C16 0.047(2) 0.066(3) 0.084(3) 0.017(3) 0.024(2) -0.005(2) C17 0.053(2) 0.044(2) 0.070(3) 0.007(2) 0.015(2) -0.0079(19) C18 0.0354(19) 0.044(2) 0.050(2) 0.0053(17) 0.0120(16) 0.0010(16) C19 0.074(3) 0.047(2) 0.041(2) 0.0015(18) 0.021(2) 0.011(2) C20 0.065(3) 0.039(2) 0.044(2) -0.0068(17) 0.0010(19) -0.0026(19) C21 0.056(3) 0.043(2) 0.072(3) -0.008(2) 0.012(2) -0.0099(19) C23 0.041(2) 0.044(2) 0.046(2) 0.0028(17) 0.0090(16) 0.0029(16) C22 0.059(2) 0.053(3) 0.040(2) 0.0043(18) 0.0095(19) 0.0002(19) C24 0.123(5) 0.068(3) 0.085(4) 0.004(3) 0.056(4) -0.019(3) N1 0.0407(16) 0.0414(17) 0.0400(16) -0.0001(13) 0.0181(13) 0.0043(13) N2 0.052(2) 0.0454(19) 0.066(2) -0.0083(17) 0.0222(17) -0.0066(15) N3 0.0464(17) 0.0328(16) 0.0358(16) -0.0015(12) 0.0061(13) 0.0021(13) N4 0.071(2) 0.0399(18) 0.0504(19) 0.0015(15) 0.0254(17) -0.0027(17) Se1 0.0393(2) 0.0495(2) 0.0434(2) -0.01080(17) 0.00872(16) -0.00048(16) Se2 0.0356(2) 0.0436(2) 0.0433(2) 0.00438(16) 0.00645(15) -0.00501(15) _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 C1 C6 1.385(5) . ? C1 C2 1.394(5) . ? C1 Se1 1.929(3) . ? C2 C3 1.381(5) . ? C2 C7 1.503(5) . ? C3 C4 1.379(5) . ? C3 H3 0.9300 . ? C4 C5 1.370(5) . ? C4 H4 0.9300 . ? C5 C6 1.383(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.453(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.445(5) . ? C8 C9 1.512(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.450(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C11 N1 1.471(4) . ? C11 C10 1.501(6) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C10 N2 1.440(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C12 N2 1.451(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C18 1.385(5) . ? C13 C14 1.393(5) . ? C13 Se2 1.937(3) . ? C14 C15 1.394(5) . ? C14 C19 1.488(5) . ? C15 C16 1.368(6) . ? C15 H15 0.9300 . ? C16 C17 1.371(6) . ? C16 H16 0.9300 . ? C17 C18 1.382(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 N3 1.469(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 N3 1.450(5) . ? C20 C21 1.494(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 N4 1.451(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C23 N3 1.452(4) . ? C23 C22 1.514(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C22 N4 1.444(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C24 N4 1.458(5) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? Se1 Se2 2.3700(5) . ? 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 C1 C2 120.2(3) . . ? C6 C1 Se1 121.8(3) . . ? C2 C1 Se1 118.0(3) . . ? C3 C2 C1 118.4(3) . . ? C3 C2 C7 120.7(3) . . ? C1 C2 C7 120.9(3) . . ? C4 C3 C2 121.5(3) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C5 C4 C3 119.7(4) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 120.2(4) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 120.0(3) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? N1 C7 C2 112.7(3) . . ? N1 C7 H7A 109.0 . . ? C2 C7 H7A 109.0 . . ? N1 C7 H7B 109.0 . . ? C2 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? N1 C8 C9 111.5(3) . . ? N1 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N1 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? N2 C9 C8 110.2(3) . . ? N2 C9 H9A 109.6 . . ? C8 C9 H9A 109.6 . . ? N2 C9 H9B 109.6 . . ? C8 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? N1 C11 C10 111.2(3) . . ? N1 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 . . ? N1 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? N2 C10 C11 111.6(3) . . ? N2 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? N2 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 120.1(3) . . ? C18 C13 Se2 121.8(3) . . ? C14 C13 Se2 118.0(3) . . ? C13 C14 C15 118.2(4) . . ? C13 C14 C19 120.2(3) . . ? C15 C14 C19 121.6(4) . . ? C16 C15 C14 121.5(4) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 119.8(4) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C18 120.2(4) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 120.2(4) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? N3 C19 C14 110.1(3) . . ? N3 C19 H19A 109.6 . . ? C14 C19 H19A 109.6 . . ? N3 C19 H19B 109.6 . . ? C14 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? N3 C20 C21 109.7(3) . . ? N3 C20 H20A 109.7 . . ? C21 C20 H20A 109.7 . . ? N3 C20 H20B 109.7 . . ? C21 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? N4 C21 C20 111.2(3) . . ? N4 C21 H21A 109.4 . . ? C20 C21 H21A 109.4 . . ? N4 C21 H21B 109.4 . . ? C20 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? N3 C23 C22 109.9(3) . . ? N3 C23 H23A 109.7 . . ? C22 C23 H23A 109.7 . . ? N3 C23 H23B 109.7 . . ? C22 C23 H23B 109.7 . . ? H23A C23 H23B 108.2 . . ? N4 C22 C23 111.2(3) . . ? N4 C22 H22A 109.4 . . ? C23 C22 H22A 109.4 . . ? N4 C22 H22B 109.4 . . ? C23 C22 H22B 109.4 . . ? H22A C22 H22B 108.0 . . ? N4 C24 H24A 109.5 . . ? N4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C8 N1 C7 111.6(3) . . ? C8 N1 C11 109.2(3) . . ? C7 N1 C11 110.2(3) . . ? C10 N2 C9 109.1(3) . . ? C10 N2 C12 112.7(4) . . ? C9 N2 C12 111.0(3) . . ? C20 N3 C23 110.9(3) . . ? C20 N3 C19 112.4(3) . . ? C23 N3 C19 112.6(3) . . ? C22 N4 C21 108.8(3) . . ? C22 N4 C24 110.6(3) . . ? C21 N4 C24 111.4(4) . . ? C1 Se1 Se2 100.34(10) . . ? C13 Se2 Se1 101.13(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.5(5) . . . . ? Se1 C1 C2 C3 -179.9(3) . . . . ? C6 C1 C2 C7 -178.4(3) . . . . ? Se1 C1 C2 C7 1.3(4) . . . . ? C1 C2 C3 C4 -0.4(6) . . . . ? C7 C2 C3 C4 178.4(4) . . . . ? C2 C3 C4 C5 0.7(6) . . . . ? C3 C4 C5 C6 -0.9(6) . . . . ? C4 C5 C6 C1 1.0(6) . . . . ? C2 C1 C6 C5 -0.7(5) . . . . ? Se1 C1 C6 C5 179.6(3) . . . . ? C3 C2 C7 N1 115.6(4) . . . . ? C1 C2 C7 N1 -65.6(4) . . . . ? N1 C8 C9 N2 59.4(5) . . . . ? N1 C11 C10 N2 -57.0(4) . . . . ? C18 C13 C14 C15 -0.4(5) . . . . ? Se2 C13 C14 C15 175.9(3) . . . . ? C18 C13 C14 C19 179.0(3) . . . . ? Se2 C13 C14 C19 -4.6(4) . . . . ? C13 C14 C15 C16 0.6(6) . . . . ? C19 C14 C15 C16 -178.9(4) . . . . ? C14 C15 C16 C17 -0.3(7) . . . . ? C15 C16 C17 C18 -0.1(7) . . . . ? C16 C17 C18 C13 0.2(6) . . . . ? C14 C13 C18 C17 0.1(5) . . . . ? Se2 C13 C18 C17 -176.1(3) . . . . ? C13 C14 C19 N3 49.8(5) . . . . ? C15 C14 C19 N3 -130.7(4) . . . . ? N3 C20 C21 N4 59.3(4) . . . . ? N3 C23 C22 N4 -57.3(4) . . . . ? C9 C8 N1 C7 -178.5(3) . . . . ? C9 C8 N1 C11 -56.4(4) . . . . ? C2 C7 N1 C8 -66.8(4) . . . . ? C2 C7 N1 C11 171.6(3) . . . . ? C10 C11 N1 C8 55.0(4) . . . . ? C10 C11 N1 C7 177.9(3) . . . . ? C11 C10 N2 C9 58.3(4) . . . . ? C11 C10 N2 C12 -177.8(4) . . . . ? C8 C9 N2 C10 -58.7(4) . . . . ? C8 C9 N2 C12 176.5(4) . . . . ? C21 C20 N3 C23 -57.5(4) . . . . ? C21 C20 N3 C19 175.5(3) . . . . ? C22 C23 N3 C20 56.4(4) . . . . ? C22 C23 N3 C19 -176.7(3) . . . . ? C14 C19 N3 C20 -160.7(3) . . . . ? C14 C19 N3 C23 73.2(4) . . . . ? C23 C22 N4 C21 58.2(4) . . . . ? C23 C22 N4 C24 -179.2(4) . . . . ? C20 C21 N4 C22 -59.4(4) . . . . ? C20 C21 N4 C24 178.4(3) . . . . ? C6 C1 Se1 Se2 35.3(3) . . . . ? C2 C1 Se1 Se2 -144.4(2) . . . . ? C18 C13 Se2 Se1 -30.3(3) . . . . ? C14 C13 Se2 Se1 153.4(2) . . . . ? C1 Se1 Se2 C13 -113.97(14) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.697 _refine_diff_density_min -0.408 _refine_diff_density_rms 0.075 # Attachment 'Compound 5 - CCDC 608162.cif' data_238rich _database_code_depnum_ccdc_archive 'CCDC 608162' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H14 I N O Se' _chemical_formula_sum 'C11 H14 I N O Se' _chemical_formula_weight 382.09 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' _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 8.2818(7) _cell_length_b 14.3309(12) _cell_length_c 10.7167(9) _cell_angle_alpha 90.00 _cell_angle_beta 97.3370(10) _cell_angle_gamma 90.00 _cell_volume 1261.50(18) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3825 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 26.04 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.012 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 5.399 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.260 _exptl_absorpt_correction_T_max 0.5528 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9982 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2578 _reflns_number_gt 2407 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0222P)^2^+0.9789P] 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 2578 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0354 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0667 _refine_ls_wR_factor_gt 0.0652 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.174 _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 C1 C 0.7246(4) 0.1247(3) 0.7676(3) 0.0329(8) Uani 1 1 d . . . C2 C 0.6243(4) 0.2017(3) 0.7796(4) 0.0378(9) Uani 1 1 d . . . C3 C 0.5556(5) 0.2124(4) 0.8896(4) 0.0523(11) Uani 1 1 d . . . H3 H 0.4893 0.2637 0.8988 0.063 Uiso 1 1 calc R . . C4 C 0.5831(6) 0.1489(4) 0.9853(4) 0.0603(14) Uani 1 1 d . . . H4 H 0.5372 0.1576 1.0592 0.072 Uiso 1 1 calc R . . C5 C 0.6793(6) 0.0718(4) 0.9718(4) 0.0588(13) Uani 1 1 d . . . H5 H 0.6957 0.0278 1.0360 0.071 Uiso 1 1 calc R . . C6 C 0.7516(5) 0.0594(3) 0.8632(4) 0.0435(10) Uani 1 1 d . . . H6 H 0.8175 0.0079 0.8546 0.052 Uiso 1 1 calc R . . C7 C 0.5990(5) 0.2685(3) 0.6718(4) 0.0402(9) Uani 1 1 d . . . H7A H 0.4970 0.3016 0.6726 0.048 Uiso 1 1 calc R . . H7B H 0.6867 0.3138 0.6783 0.048 Uiso 1 1 calc R . . C8 C 0.6209(5) 0.2756(3) 0.4474(4) 0.0366(9) Uani 1 1 d . . . H8A H 0.7257 0.3064 0.4643 0.044 Uiso 1 1 calc R . . H8B H 0.5371 0.3232 0.4371 0.044 Uiso 1 1 calc R . . C9 C 0.6148(5) 0.2192(3) 0.3282(4) 0.0424(9) Uani 1 1 d . . . H9A H 0.6292 0.2605 0.2587 0.051 Uiso 1 1 calc R . . H9B H 0.7036 0.1746 0.3367 0.051 Uiso 1 1 calc R . . C10 C 0.4418(6) 0.1104(3) 0.4018(4) 0.0501(11) Uani 1 1 d . . . H10A H 0.5279 0.0641 0.4113 0.060 Uiso 1 1 calc R . . H10B H 0.3390 0.0779 0.3819 0.060 Uiso 1 1 calc R . . C11 C 0.4414(4) 0.1622(3) 0.5236(4) 0.0402(9) Uani 1 1 d . . . H11A H 0.3503 0.2053 0.5166 0.048 Uiso 1 1 calc R . . H11B H 0.4284 0.1183 0.5905 0.048 Uiso 1 1 calc R . . I1 I 1.08198(3) 0.01463(2) 0.69359(3) 0.04835(11) Uani 1 1 d . . . N1 N 0.5959(3) 0.2146(2) 0.5548(3) 0.0313(7) Uani 1 1 d . . . O1 O 0.4653(4) 0.1710(2) 0.3011(3) 0.0508(7) Uani 1 1 d . . . Se1 Se 0.81358(4) 0.11792(2) 0.60993(3) 0.03100(11) 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 C1 0.0314(19) 0.042(2) 0.0263(18) -0.0030(15) 0.0059(15) -0.0087(16) C2 0.0292(19) 0.048(2) 0.037(2) -0.0087(17) 0.0049(16) -0.0027(17) C3 0.037(2) 0.079(3) 0.042(2) -0.014(2) 0.0087(19) 0.002(2) C4 0.046(3) 0.102(4) 0.036(2) -0.011(3) 0.018(2) -0.013(3) C5 0.060(3) 0.083(4) 0.032(2) 0.012(2) 0.003(2) -0.019(3) C6 0.043(2) 0.048(2) 0.039(2) 0.0054(18) 0.0053(18) -0.0040(19) C7 0.039(2) 0.037(2) 0.045(2) -0.0090(17) 0.0049(17) 0.0084(17) C8 0.034(2) 0.029(2) 0.046(2) 0.0066(16) 0.0037(17) 0.0032(16) C9 0.048(2) 0.042(2) 0.038(2) 0.0072(18) 0.0062(18) 0.0053(19) C10 0.052(3) 0.045(2) 0.049(2) 0.004(2) -0.010(2) -0.012(2) C11 0.0271(19) 0.047(2) 0.045(2) 0.0041(18) -0.0004(16) -0.0046(17) I1 0.04645(18) 0.04869(18) 0.04867(18) 0.00106(12) 0.00130(13) 0.01977(12) N1 0.0284(15) 0.0307(16) 0.0344(16) 0.0012(13) 0.0025(12) 0.0032(13) O1 0.0572(19) 0.0527(18) 0.0386(16) 0.0039(13) -0.0089(13) -0.0010(15) Se1 0.0323(2) 0.0309(2) 0.0302(2) 0.00041(14) 0.00540(15) 0.00183(15) _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 C1 C6 1.385(5) . ? C1 C2 1.397(5) . ? C1 Se1 1.930(3) . ? C2 C3 1.382(5) . ? C2 C7 1.494(5) . ? C3 C4 1.368(7) . ? C3 H3 0.9300 . ? C4 C5 1.380(7) . ? C4 H4 0.9300 . ? C5 C6 1.387(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.470(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.481(5) . ? C8 C9 1.507(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O1 1.415(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O1 1.418(5) . ? C10 C11 1.502(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N1 1.484(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? I1 Se1 2.7252(5) . ? N1 Se1 2.291(3) . ? 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 C1 C2 120.5(4) . . ? C6 C1 Se1 124.7(3) . . ? C2 C1 Se1 114.7(3) . . ? C3 C2 C1 118.7(4) . . ? C3 C2 C7 123.8(4) . . ? C1 C2 C7 117.5(3) . . ? C4 C3 C2 121.3(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.8(4) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C4 C5 C6 120.5(4) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 119.3(4) . . ? C1 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? N1 C7 C2 107.9(3) . . ? N1 C7 H7A 110.1 . . ? C2 C7 H7A 110.1 . . ? N1 C7 H7B 110.1 . . ? C2 C7 H7B 110.1 . . ? H7A C7 H7B 108.4 . . ? N1 C8 C9 110.5(3) . . ? N1 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? N1 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? O1 C9 C8 111.7(3) . . ? O1 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? O1 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 107.9 . . ? O1 C10 C11 112.0(3) . . ? O1 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? O1 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? N1 C11 C10 110.4(3) . . ? N1 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? N1 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C7 N1 C8 111.4(3) . . ? C7 N1 C11 112.3(3) . . ? C8 N1 C11 109.0(3) . . ? C7 N1 Se1 99.8(2) . . ? C8 N1 Se1 111.9(2) . . ? C11 N1 Se1 112.3(2) . . ? C9 O1 C10 110.2(3) . . ? C1 Se1 N1 79.58(13) . . ? C1 Se1 I1 97.24(11) . . ? N1 Se1 I1 174.52(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.4(6) . . . . ? Se1 C1 C2 C3 -179.8(3) . . . . ? C6 C1 C2 C7 -179.2(3) . . . . ? Se1 C1 C2 C7 -0.4(4) . . . . ? C1 C2 C3 C4 -0.6(6) . . . . ? C7 C2 C3 C4 -180.0(4) . . . . ? C2 C3 C4 C5 -1.0(7) . . . . ? C3 C4 C5 C6 1.6(7) . . . . ? C2 C1 C6 C5 -0.7(6) . . . . ? Se1 C1 C6 C5 -179.4(3) . . . . ? C4 C5 C6 C1 -0.8(7) . . . . ? C3 C2 C7 N1 -145.4(4) . . . . ? C1 C2 C7 N1 35.2(4) . . . . ? N1 C8 C9 O1 57.8(4) . . . . ? O1 C10 C11 N1 -57.5(4) . . . . ? C2 C7 N1 C8 -162.9(3) . . . . ? C2 C7 N1 C11 74.5(4) . . . . ? C2 C7 N1 Se1 -44.6(3) . . . . ? C9 C8 N1 C7 -179.2(3) . . . . ? C9 C8 N1 C11 -54.8(4) . . . . ? C9 C8 N1 Se1 70.1(3) . . . . ? C10 C11 N1 C7 178.4(3) . . . . ? C10 C11 N1 C8 54.6(4) . . . . ? C10 C11 N1 Se1 -70.0(3) . . . . ? C8 C9 O1 C10 -58.9(4) . . . . ? C11 C10 O1 C9 58.9(5) . . . . ? C6 C1 Se1 N1 158.1(3) . . . . ? C2 C1 Se1 N1 -20.6(3) . . . . ? C6 C1 Se1 I1 -26.4(3) . . . . ? C2 C1 Se1 I1 154.9(3) . . . . ? C7 N1 Se1 C1 36.9(2) . . . . ? C8 N1 Se1 C1 154.8(3) . . . . ? C11 N1 Se1 C1 -82.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.580 _refine_diff_density_min -0.841 _refine_diff_density_rms 0.096 # Attachment 'Compound 4 - CCDC 619305.cif' data_235rich _database_code_depnum_ccdc_archive 'CCDC 619305' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H15 Br2 N O Se' _chemical_formula_sum 'C11 H15 Br2 N O Se' _chemical_formula_weight 416.02 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' Se Se -0.0929 2.2259 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pna2(1) ' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 16.141(2) _cell_length_b 12.6448(16) _cell_length_c 6.9126(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1410.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3007 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 25.24 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.959 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 8.306 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2165 _exptl_absorpt_correction_T_max 0.6075 _exptl_absorpt_process_details 'Bruker, 2001.' _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11006 _diffrn_reflns_av_R_equivalents 0.0678 _diffrn_reflns_av_sigmaI/netI 0.0685 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 26.41 _reflns_number_total 2867 _reflns_number_gt 2414 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0467P)^2^+0.6457P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(3) _refine_ls_number_reflns 2867 _refine_ls_number_parameters 149 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0685 _refine_ls_wR_factor_ref 0.1298 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 1.173 _refine_ls_restrained_S_all 1.173 _refine_ls_shift/su_max 0.028 _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 C1 C 0.8238(5) 0.1233(6) 0.5889(12) 0.0236(19) Uani 1 1 d . . . C2 C 0.8084(4) 0.2175(6) 0.4973(12) 0.0230(18) Uani 1 1 d . . . C3 C 0.8315(6) 0.3116(8) 0.5828(16) 0.044(3) Uani 1 1 d . . . H3 H 0.8211 0.3760 0.5225 0.053 Uiso 1 1 calc R . . C4 C 0.8709(6) 0.3074(9) 0.7627(17) 0.047(3) Uani 1 1 d . . . H4 H 0.8864 0.3700 0.8235 0.057 Uiso 1 1 calc R . . C5 C 0.8873(6) 0.2123(10) 0.8514(14) 0.046(3) Uani 1 1 d . . . H5 H 0.9146 0.2105 0.9700 0.055 Uiso 1 1 calc R . . C6 C 0.8632(5) 0.1204(8) 0.7636(13) 0.033(2) Uani 1 1 d . . . H6 H 0.8737 0.0557 0.8230 0.039 Uiso 1 1 calc R . . C7 C 0.7682(5) 0.2232(7) 0.3021(14) 0.034(2) Uani 1 1 d . . . H7A H 0.7950 0.1732 0.2159 0.041 Uiso 1 1 calc R . . H7B H 0.7759 0.2935 0.2489 0.041 Uiso 1 1 calc R . . C8 C 0.6430(6) 0.1712(10) 0.1191(12) 0.049(3) Uani 1 1 d . . . H8A H 0.6720 0.1100 0.0682 0.059 Uiso 1 1 calc R . . H8B H 0.6514 0.2296 0.0303 0.059 Uiso 1 1 calc R . . C9 C 0.5508(6) 0.1468(9) 0.1350(17) 0.058(3) Uani 1 1 d . . . H9A H 0.5287 0.1305 0.0080 0.070 Uiso 1 1 calc R . . H9B H 0.5426 0.0856 0.2174 0.070 Uiso 1 1 calc R . . C10 C 0.5375(6) 0.2591(10) 0.3984(16) 0.055(3) Uani 1 1 d . . . H10A H 0.5284 0.1991 0.4833 0.066 Uiso 1 1 calc R . . H10B H 0.5059 0.3183 0.4487 0.066 Uiso 1 1 calc R . . C11 C 0.6278(6) 0.2868(9) 0.3978(15) 0.044(3) Uani 1 1 d . . . H11A H 0.6364 0.3510 0.3237 0.053 Uiso 1 1 calc R . . H11B H 0.6463 0.2996 0.5293 0.053 Uiso 1 1 calc R . . N1 N 0.6772(4) 0.1990(6) 0.3114(11) 0.0248(16) Uani 1 1 d . . . O1 O 0.5091(4) 0.2342(6) 0.2128(11) 0.059(2) Uani 1 1 d . . . Se1 Se 0.79053(6) -0.00833(7) 0.46945(16) 0.0397(3) Uani 1 1 d . . . Br1 Br 0.91953(8) -0.02793(11) 0.2893(2) 0.0757(5) Uani 1 1 d . . . Br2 Br 0.63994(6) 0.02143(8) 0.66432(14) 0.0460(3) Uani 1 1 d . . . H2 H 0.671(4) 0.145(5) 0.381(10) 0.000(18) 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 C1 0.015(4) 0.027(5) 0.028(5) -0.006(4) -0.005(3) -0.001(4) C2 0.012(4) 0.031(4) 0.026(5) -0.011(4) 0.003(4) -0.001(3) C3 0.039(6) 0.033(6) 0.059(8) -0.003(5) -0.015(5) 0.000(5) C4 0.029(6) 0.053(7) 0.060(7) -0.034(6) 0.008(6) -0.003(5) C5 0.034(6) 0.090(9) 0.014(5) -0.011(5) -0.003(4) -0.014(6) C6 0.023(5) 0.048(6) 0.027(5) -0.003(4) -0.005(4) 0.003(4) C7 0.041(5) 0.033(5) 0.028(5) -0.001(4) 0.000(5) -0.007(4) C8 0.053(7) 0.075(8) 0.021(6) -0.006(5) -0.009(5) 0.015(6) C9 0.042(6) 0.078(9) 0.056(8) -0.018(7) -0.026(6) 0.002(6) C10 0.033(6) 0.078(9) 0.054(7) 0.001(6) -0.003(5) 0.021(6) C11 0.051(7) 0.049(6) 0.034(6) -0.003(5) -0.019(5) 0.019(5) N1 0.032(4) 0.024(4) 0.019(4) 0.009(4) -0.003(3) -0.001(3) O1 0.041(4) 0.083(6) 0.053(5) -0.009(4) -0.021(3) 0.015(4) Se1 0.0485(5) 0.0211(4) 0.0496(6) -0.0039(5) -0.0173(5) 0.0016(4) Br1 0.0497(7) 0.0808(10) 0.0967(12) -0.0475(10) 0.0010(7) 0.0109(7) Br2 0.0528(6) 0.0465(6) 0.0387(6) 0.0027(6) 0.0035(5) -0.0135(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 C1 C6 1.366(11) . ? C1 C2 1.371(11) . ? C1 Se1 1.934(8) . ? C2 C3 1.380(12) . ? C2 C7 1.499(12) . ? C3 C4 1.398(14) . ? C4 C5 1.375(16) . ? C5 C6 1.368(13) . ? C7 N1 1.501(11) . ? C8 N1 1.481(11) . ? C8 C9 1.524(13) . ? C9 O1 1.402(12) . ? C10 O1 1.398(11) . ? C10 C11 1.500(13) . ? C11 N1 1.492(12) . ? Se1 Br1 2.4389(18) . ? Se1 Br2 2.8043(15) . ? 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 C1 C2 121.1(8) . . ? C6 C1 Se1 118.9(7) . . ? C2 C1 Se1 120.0(6) . . ? C1 C2 C3 120.1(8) . . ? C1 C2 C7 122.4(7) . . ? C3 C2 C7 117.5(8) . . ? C2 C3 C4 118.1(10) . . ? C5 C4 C3 121.2(10) . . ? C6 C5 C4 119.3(9) . . ? C1 C6 C5 120.1(10) . . ? C2 C7 N1 112.0(7) . . ? N1 C8 C9 110.3(8) . . ? O1 C9 C8 109.7(9) . . ? O1 C10 C11 111.6(9) . . ? N1 C11 C10 110.3(9) . . ? C8 N1 C11 109.7(7) . . ? C8 N1 C7 112.0(8) . . ? C11 N1 C7 112.8(7) . . ? C10 O1 C9 111.8(8) . . ? C1 Se1 Br1 93.9(2) . . ? C1 Se1 Br2 85.4(2) . . ? Br1 Se1 Br2 177.34(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.2(13) . . . . ? Se1 C1 C2 C3 179.5(7) . . . . ? C6 C1 C2 C7 177.6(8) . . . . ? Se1 C1 C2 C7 -1.7(11) . . . . ? C1 C2 C3 C4 0.4(14) . . . . ? C7 C2 C3 C4 -178.4(8) . . . . ? C2 C3 C4 C5 0.8(15) . . . . ? C3 C4 C5 C6 -1.2(15) . . . . ? C2 C1 C6 C5 0.7(13) . . . . ? Se1 C1 C6 C5 -179.9(7) . . . . ? C4 C5 C6 C1 0.5(14) . . . . ? C1 C2 C7 N1 73.6(10) . . . . ? C3 C2 C7 N1 -107.6(9) . . . . ? N1 C8 C9 O1 57.9(12) . . . . ? O1 C10 C11 N1 -56.0(13) . . . . ? C9 C8 N1 C11 -54.1(12) . . . . ? C9 C8 N1 C7 179.8(8) . . . . ? C10 C11 N1 C8 52.9(12) . . . . ? C10 C11 N1 C7 178.5(8) . . . . ? C2 C7 N1 C8 -161.9(8) . . . . ? C2 C7 N1 C11 73.8(10) . . . . ? C11 C10 O1 C9 60.8(13) . . . . ? C8 C9 O1 C10 -60.9(12) . . . . ? C6 C1 Se1 Br1 -91.2(7) . . . . ? C2 C1 Se1 Br1 88.2(7) . . . . ? C6 C1 Se1 Br2 91.4(6) . . . . ? C2 C1 Se1 Br2 -89.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.771 _refine_diff_density_min -0.725 _refine_diff_density_rms 0.137 data_248rich _database_code_depnum_ccdc_archive 'CCDC 619306' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H28 N2 O2 Se2' _chemical_formula_sum 'C22 H28 N2 O2 Se2' _chemical_formula_weight 510.38 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' Se Se -0.0929 2.2259 '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 ' _symmetry_space_group_name_Hall '-P 2ybc' 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 12.0689(14) _cell_length_b 18.435(2) _cell_length_c 10.1788(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.069(2) _cell_angle_gamma 90.00 _cell_volume 2261.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 3493 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 21.98 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.499 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 3.289 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3609 _exptl_absorpt_correction_T_max 0.5685 _exptl_absorpt_process_details 'Bruker, 2001.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18027 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4622 _reflns_number_gt 3734 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0470P)^2^+0.5463P] 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 4622 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1090 _refine_ls_wR_factor_gt 0.1024 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.126 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4941(3) 0.13309(19) 0.4308(4) 0.0445(8) Uani 1 1 d . . . C2 C 0.5807(3) 0.0837(2) 0.4522(4) 0.0520(10) Uani 1 1 d . . . C3 C 0.6253(4) 0.0528(2) 0.3420(5) 0.0703(13) Uani 1 1 d . . . H3 H 0.6844 0.0207 0.3537 0.084 Uiso 1 1 calc R . . C4 C 0.5848(4) 0.0683(3) 0.2163(5) 0.0754(14) Uani 1 1 d . . . H4 H 0.6158 0.0467 0.1443 0.090 Uiso 1 1 calc R . . C5 C 0.4978(4) 0.1160(2) 0.1985(4) 0.0669(12) Uani 1 1 d . . . H5 H 0.4687 0.1261 0.1141 0.080 Uiso 1 1 calc R . . C6 C 0.4537(3) 0.1488(2) 0.3049(4) 0.0526(10) Uani 1 1 d . . . H6 H 0.3961 0.1820 0.2919 0.063 Uiso 1 1 calc R . . C7 C 0.6237(4) 0.0622(2) 0.5885(4) 0.0662(12) Uani 1 1 d . . . H7A H 0.5723 0.0281 0.6247 0.079 Uiso 1 1 calc R . . H7B H 0.6944 0.0376 0.5824 0.079 Uiso 1 1 calc R . . C8 C 0.7285(3) 0.1693(2) 0.6434(4) 0.0601(11) Uani 1 1 d . . . H8A H 0.7166 0.1862 0.5535 0.072 Uiso 1 1 calc R . . H8B H 0.7975 0.1422 0.6497 0.072 Uiso 1 1 calc R . . C9 C 0.7369(4) 0.2330(3) 0.7342(4) 0.0753(14) Uani 1 1 d . . . H9A H 0.7986 0.2633 0.7112 0.090 Uiso 1 1 calc R . . H9B H 0.6696 0.2616 0.7239 0.090 Uiso 1 1 calc R . . C10 C 0.6634(4) 0.1666(3) 0.8994(4) 0.0802(14) Uani 1 1 d . . . H10A H 0.5955 0.1947 0.8908 0.096 Uiso 1 1 calc R . . H10B H 0.6739 0.1514 0.9904 0.096 Uiso 1 1 calc R . . C11 C 0.6520(4) 0.1013(3) 0.8135(4) 0.0730(13) Uani 1 1 d . . . H11A H 0.7176 0.0711 0.8263 0.088 Uiso 1 1 calc R . . H11B H 0.5883 0.0731 0.8375 0.088 Uiso 1 1 calc R . . C12 C 0.1657(3) 0.18740(18) 0.4546(3) 0.0385(8) Uani 1 1 d . . . C13 C 0.0589(3) 0.2142(2) 0.4663(3) 0.0454(9) Uani 1 1 d . . . C14 C -0.0301(3) 0.1695(2) 0.4299(4) 0.0576(11) Uani 1 1 d . . . H14 H -0.1021 0.1867 0.4357 0.069 Uiso 1 1 calc R . . C15 C -0.0134(4) 0.0993(2) 0.3850(4) 0.0605(11) Uani 1 1 d . . . H15 H -0.0737 0.0699 0.3607 0.073 Uiso 1 1 calc R . . C16 C 0.0918(4) 0.0740(2) 0.3768(4) 0.0539(10) Uani 1 1 d . . . H16 H 0.1033 0.0268 0.3481 0.065 Uiso 1 1 calc R . . C17 C 0.1814(3) 0.11748(19) 0.4107(3) 0.0452(9) Uani 1 1 d . . . H17 H 0.2530 0.0997 0.4040 0.054 Uiso 1 1 calc R . . C18 C 0.0408(3) 0.2892(2) 0.5190(4) 0.0551(10) Uani 1 1 d . . . H18A H -0.0377 0.3008 0.5102 0.066 Uiso 1 1 calc R . . H18B H 0.0635 0.2905 0.6118 0.066 Uiso 1 1 calc R . . C19 C 0.1150(4) 0.4111(2) 0.5205(4) 0.0633(12) Uani 1 1 d . . . H19A H 0.1507 0.4024 0.6067 0.076 Uiso 1 1 calc R . . H19B H 0.0424 0.4318 0.5325 0.076 Uiso 1 1 calc R . . C20 C 0.1833(5) 0.4632(2) 0.4455(5) 0.0795(14) Uani 1 1 d . . . H20A H 0.1890 0.5088 0.4930 0.095 Uiso 1 1 calc R . . H20B H 0.2576 0.4439 0.4399 0.095 Uiso 1 1 calc R . . C21 C 0.1256(5) 0.4097(2) 0.2491(4) 0.0742(14) Uani 1 1 d . . . H21A H 0.1983 0.3887 0.2388 0.089 Uiso 1 1 calc R . . H21B H 0.0922 0.4193 0.1621 0.089 Uiso 1 1 calc R . . C22 C 0.0554(4) 0.3570(2) 0.3182(4) 0.0558(10) Uani 1 1 d . . . H22A H -0.0190 0.3764 0.3233 0.067 Uiso 1 1 calc R . . H22B H 0.0503 0.3120 0.2690 0.067 Uiso 1 1 calc R . . N1 N 0.6381(2) 0.12261(16) 0.6764(3) 0.0486(8) Uani 1 1 d . . . N2 N 0.1027(2) 0.34303(15) 0.4498(3) 0.0400(7) Uani 1 1 d . . . O1 O 0.7529(3) 0.21056(19) 0.8671(3) 0.0776(9) Uani 1 1 d . . . O2 O 0.1377(3) 0.47592(15) 0.3193(3) 0.0772(9) Uani 1 1 d . . . Se1 Se 0.43020(3) 0.17612(2) 0.58340(4) 0.05199(14) Uani 1 1 d . . . Se2 Se 0.28914(3) 0.251970(19) 0.49478(4) 0.05024(14) 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 C1 0.039(2) 0.0386(19) 0.056(2) -0.0018(17) 0.0045(17) -0.0019(16) C2 0.044(2) 0.044(2) 0.067(3) -0.0034(19) -0.0001(19) 0.0027(17) C3 0.057(3) 0.057(3) 0.099(4) -0.005(3) 0.015(3) 0.012(2) C4 0.080(4) 0.074(3) 0.075(3) -0.011(3) 0.029(3) 0.000(3) C5 0.072(3) 0.069(3) 0.061(3) 0.006(2) 0.014(2) 0.004(2) C6 0.048(2) 0.054(2) 0.057(2) 0.0059(19) 0.0064(19) 0.0010(19) C7 0.058(3) 0.053(3) 0.086(3) 0.010(2) -0.012(2) 0.011(2) C8 0.039(2) 0.077(3) 0.064(3) 0.007(2) 0.0000(19) -0.005(2) C9 0.073(3) 0.078(3) 0.074(3) 0.004(3) -0.005(3) -0.033(3) C10 0.078(3) 0.104(4) 0.059(3) 0.007(3) 0.008(3) -0.011(3) C11 0.072(3) 0.077(3) 0.069(3) 0.022(3) -0.005(2) -0.013(3) C12 0.041(2) 0.040(2) 0.0337(17) 0.0018(14) -0.0008(15) -0.0029(15) C13 0.043(2) 0.049(2) 0.045(2) 0.0140(17) 0.0088(17) 0.0102(18) C14 0.036(2) 0.070(3) 0.067(3) 0.022(2) 0.0072(19) 0.001(2) C15 0.054(3) 0.063(3) 0.064(3) 0.007(2) -0.004(2) -0.018(2) C16 0.067(3) 0.045(2) 0.050(2) -0.0030(17) 0.003(2) -0.008(2) C17 0.045(2) 0.046(2) 0.045(2) 0.0003(16) 0.0055(17) 0.0034(17) C18 0.054(2) 0.058(2) 0.056(2) 0.007(2) 0.021(2) 0.017(2) C19 0.092(3) 0.057(3) 0.041(2) -0.0103(19) -0.001(2) 0.012(2) C20 0.103(4) 0.053(3) 0.081(3) -0.008(2) -0.011(3) -0.019(3) C21 0.119(4) 0.054(3) 0.051(2) 0.004(2) 0.010(3) -0.003(3) C22 0.071(3) 0.051(2) 0.044(2) 0.0015(18) -0.010(2) 0.000(2) N1 0.0365(17) 0.0483(18) 0.060(2) 0.0105(15) -0.0050(15) 0.0021(14) N2 0.0468(17) 0.0395(16) 0.0335(15) -0.0007(12) 0.0013(13) 0.0082(13) O1 0.071(2) 0.096(2) 0.065(2) -0.0010(18) -0.0064(16) -0.0205(19) O2 0.119(3) 0.0465(17) 0.066(2) 0.0041(15) 0.0043(19) -0.0075(17) Se1 0.0465(2) 0.0549(3) 0.0535(2) -0.00486(18) -0.00767(18) 0.01243(18) Se2 0.0423(2) 0.0405(2) 0.0665(3) -0.00634(18) -0.00953(19) 0.00443(16) _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 C1 C6 1.377(5) . ? C1 C2 1.395(5) . ? C1 Se1 1.940(4) . ? C2 C3 1.392(6) . ? C2 C7 1.508(5) . ? C3 C4 1.375(6) . ? C3 H3 0.9300 . ? C4 C5 1.374(6) . ? C4 H4 0.9300 . ? C5 C6 1.373(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.434(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.444(5) . ? C8 C9 1.493(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 O1 1.418(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O1 1.402(5) . ? C10 C11 1.491(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N1 1.452(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.381(5) . ? C12 C13 1.391(5) . ? C12 Se2 1.934(3) . ? C13 C14 1.389(5) . ? C13 C18 1.503(5) . ? C14 C15 1.390(6) . ? C14 H14 0.9300 . ? C15 C16 1.360(6) . ? C15 H15 0.9300 . ? C16 C17 1.376(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 N2 1.448(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 N2 1.450(4) . ? C19 C20 1.502(6) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 O2 1.390(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 O2 1.417(5) . ? C21 C22 1.491(6) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 N2 1.451(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? Se1 Se2 2.3458(5) . ? 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 C1 C2 120.5(4) . . ? C6 C1 Se1 121.5(3) . . ? C2 C1 Se1 117.9(3) . . ? C3 C2 C1 117.4(4) . . ? C3 C2 C7 120.3(4) . . ? C1 C2 C7 122.3(4) . . ? C4 C3 C2 122.1(4) . . ? C4 C3 H3 118.9 . . ? C2 C3 H3 118.9 . . ? C5 C4 C3 119.1(4) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C6 C5 C4 120.3(4) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C1 120.5(4) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? N1 C7 C2 113.2(3) . . ? N1 C7 H7A 108.9 . . ? C2 C7 H7A 108.9 . . ? N1 C7 H7B 108.9 . . ? C2 C7 H7B 108.9 . . ? H7A C7 H7B 107.8 . . ? N1 C8 C9 110.6(3) . . ? N1 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? O1 C9 C8 111.3(4) . . ? O1 C9 H9A 109.4 . . ? C8 C9 H9A 109.4 . . ? O1 C9 H9B 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? O1 C10 C11 112.2(4) . . ? O1 C10 H10A 109.2 . . ? C11 C10 H10A 109.2 . . ? O1 C10 H10B 109.2 . . ? C11 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? N1 C11 C10 110.3(4) . . ? N1 C11 H11A 109.6 . . ? C10 C11 H11A 109.6 . . ? N1 C11 H11B 109.6 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C17 C12 C13 120.2(3) . . ? C17 C12 Se2 121.7(3) . . ? C13 C12 Se2 118.0(3) . . ? C14 C13 C12 118.2(3) . . ? C14 C13 C18 121.1(3) . . ? C12 C13 C18 120.7(3) . . ? C13 C14 C15 121.1(4) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? C16 C15 C14 119.5(4) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 120.6(4) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C12 120.3(4) . . ? C16 C17 H17 119.8 . . ? C12 C17 H17 119.8 . . ? N2 C18 C13 111.6(3) . . ? N2 C18 H18A 109.3 . . ? C13 C18 H18A 109.3 . . ? N2 C18 H18B 109.3 . . ? C13 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? N2 C19 C20 110.2(3) . . ? N2 C19 H19A 109.6 . . ? C20 C19 H19A 109.6 . . ? N2 C19 H19B 109.6 . . ? C20 C19 H19B 109.6 . . ? H19A C19 H19B 108.1 . . ? O2 C20 C19 112.1(4) . . ? O2 C20 H20A 109.2 . . ? C19 C20 H20A 109.2 . . ? O2 C20 H20B 109.2 . . ? C19 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? O2 C21 C22 111.7(3) . . ? O2 C21 H21A 109.3 . . ? C22 C21 H21A 109.3 . . ? O2 C21 H21B 109.3 . . ? C22 C21 H21B 109.3 . . ? H21A C21 H21B 107.9 . . ? N2 C22 C21 110.2(3) . . ? N2 C22 H22A 109.6 . . ? C21 C22 H22A 109.6 . . ? N2 C22 H22B 109.6 . . ? C21 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? C7 N1 C8 112.7(3) . . ? C7 N1 C11 113.2(3) . . ? C8 N1 C11 109.6(3) . . ? C18 N2 C19 113.2(3) . . ? C18 N2 C22 112.5(3) . . ? C19 N2 C22 109.2(3) . . ? C10 O1 C9 108.9(3) . . ? C20 O2 C21 110.2(3) . . ? C1 Se1 Se2 104.30(11) . . ? C12 Se2 Se1 104.45(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.4(6) . . . . ? Se1 C1 C2 C3 179.6(3) . . . . ? C6 C1 C2 C7 -177.0(4) . . . . ? Se1 C1 C2 C7 1.2(5) . . . . ? C1 C2 C3 C4 -1.7(6) . . . . ? C7 C2 C3 C4 176.7(4) . . . . ? C2 C3 C4 C5 0.3(7) . . . . ? C3 C4 C5 C6 1.3(7) . . . . ? C4 C5 C6 C1 -1.6(6) . . . . ? C2 C1 C6 C5 0.2(6) . . . . ? Se1 C1 C6 C5 -177.9(3) . . . . ? C3 C2 C7 N1 137.3(4) . . . . ? C1 C2 C7 N1 -44.4(5) . . . . ? N1 C8 C9 O1 58.4(5) . . . . ? O1 C10 C11 N1 -57.9(5) . . . . ? C17 C12 C13 C14 -1.4(5) . . . . ? Se2 C12 C13 C14 176.2(3) . . . . ? C17 C12 C13 C18 177.6(3) . . . . ? Se2 C12 C13 C18 -4.9(4) . . . . ? C12 C13 C14 C15 1.0(5) . . . . ? C18 C13 C14 C15 -178.0(3) . . . . ? C13 C14 C15 C16 0.2(6) . . . . ? C14 C15 C16 C17 -1.0(6) . . . . ? C15 C16 C17 C12 0.6(6) . . . . ? C13 C12 C17 C16 0.6(5) . . . . ? Se2 C12 C17 C16 -176.8(3) . . . . ? C14 C13 C18 N2 -128.9(4) . . . . ? C12 C13 C18 N2 52.2(5) . . . . ? N2 C19 C20 O2 57.4(5) . . . . ? O2 C21 C22 N2 -57.8(5) . . . . ? C2 C7 N1 C8 -69.6(4) . . . . ? C2 C7 N1 C11 165.3(4) . . . . ? C9 C8 N1 C7 177.6(3) . . . . ? C9 C8 N1 C11 -55.4(5) . . . . ? C10 C11 N1 C7 -178.5(4) . . . . ? C10 C11 N1 C8 54.8(5) . . . . ? C13 C18 N2 C19 -162.5(3) . . . . ? C13 C18 N2 C22 73.1(4) . . . . ? C20 C19 N2 C18 178.0(4) . . . . ? C20 C19 N2 C22 -55.9(5) . . . . ? C21 C22 N2 C18 -177.0(3) . . . . ? C21 C22 N2 C19 56.5(4) . . . . ? C11 C10 O1 C9 59.1(5) . . . . ? C8 C9 O1 C10 -59.0(5) . . . . ? C19 C20 O2 C21 -57.3(5) . . . . ? C22 C21 O2 C20 57.7(5) . . . . ? C6 C1 Se1 Se2 -1.0(3) . . . . ? C2 C1 Se1 Se2 -179.1(3) . . . . ? C17 C12 Se2 Se1 -35.3(3) . . . . ? C13 C12 Se2 Se1 147.2(2) . . . . ? C1 Se1 Se2 C12 80.94(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.664 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.070