# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email mugesh@ipc.iisc.ernet.in _publ_contact_author_name 'G. Mugesh' loop_ _publ_author_name 'Devappa S. Lamani' 'Debasish Bhowmick' 'Govindasamy Mugesh' data_dsome _database_code_depnum_ccdc_archive 'CCDC 869454' #TrackingRef 'DS-SP3OMe.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 N2 O4 Se' _chemical_formula_sum 'C28 H24 N2 O4 Se' _chemical_formula_weight 531.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 10.6590(14) _cell_length_b 11.1175(8) _cell_length_c 11.4796(8) _cell_angle_alpha 115.030(3) _cell_angle_beta 100.751(4) _cell_angle_gamma 101.470(4) _cell_volume 1150.49(19) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 20.09 _exptl_crystal_description 'needle shape' _exptl_crystal_colour white _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 1.672 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.7629 _exptl_absorpt_correction_T_max 0.9058 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 scan' _diffrn_detector_area_resol_mean 0.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25383 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 33.27 _reflns_number_total 13603 _reflns_number_gt 10679 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker kappa apex ccd' _computing_cell_refinement 'Bruker kappa apex ccd' _computing_data_reduction 'Bruker saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1999)' _computing_publication_material WinGX _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^)+(0.0411P)^2^+0.1768P] 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 0.333(19) _refine_ls_number_reflns 13603 _refine_ls_number_parameters 635 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0851 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 2.106 _refine_ls_shift/su_mean 0.356 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 Se1 Se 0.47543(2) 0.26352(2) 0.22271(2) 0.03071(15) Uani 1 1 d . . . Se2 Se 0.53025(2) 0.73625(2) -0.22166(2) 0.03107(15) Uani 1 1 d . . . O1 O 0.5490(5) 0.0696(5) -0.1385(4) 0.0453(12) Uani 1 1 d . . . O2 O 0.9977(5) 0.3523(7) 0.0027(5) 0.0579(15) Uani 1 1 d . . . N2 N 0.3527(5) 0.3199(6) 0.3445(5) 0.0344(13) Uani 1 1 d . . . O4 O 0.1141(6) 0.1930(6) 0.6220(5) 0.0596(15) Uani 1 1 d . . . O5 O 0.8959(6) 0.8102(6) -0.6153(6) 0.0647(16) Uani 1 1 d . . . O6 O 0.6920(5) 0.4798(5) -0.4827(5) 0.0458(12) Uani 1 1 d . . . N4 N 0.4239(5) 0.7851(6) -0.0839(5) 0.0334(12) Uani 1 1 d . . . O8 O 0.0089(5) 0.6499(7) -0.0034(6) 0.0631(16) Uani 1 1 d . . . N1 N 0.5857(5) 0.2179(5) 0.0886(4) 0.0330(12) Uani 1 1 d . . . C37 C 0.5740(6) 0.4782(7) -0.3257(6) 0.0381(15) Uani 1 1 d . . . C44 C 0.8160(7) 0.8591(8) -0.0531(7) 0.0438(17) Uani 1 1 d . . . C49 C 0.4955(6) 0.8730(7) 0.0442(6) 0.0365(15) Uani 1 1 d . . . C1 C 0.5067(6) 0.1278(5) -0.0406(4) 0.0296(12) Uani 1 1 d . . . C2 C 0.3627(6) 0.1028(7) -0.0586(6) 0.0332(13) Uani 1 1 d . . . C3 C 0.3252(6) 0.1583(6) 0.0618(6) 0.0329(14) Uani 1 1 d . . . C4 C 0.1930(6) 0.1430(7) 0.0533(7) 0.0390(15) Uani 1 1 d . . . H4 H 0.1674 0.1788 0.1311 0.047 Uiso 1 1 calc R . . C5 C 0.0955(7) 0.0723(8) -0.0753(7) 0.0477(18) Uani 1 1 d . . . H5 H 0.0053 0.0619 -0.0818 0.057 Uiso 1 1 calc R . . C6 C 0.1320(7) 0.0196(8) -0.1885(7) 0.0492(19) Uani 1 1 d . . . H6 H 0.0668 -0.0249 -0.2724 0.059 Uiso 1 1 calc R . . C7 C 0.2671(7) 0.0310(7) -0.1815(6) 0.0421(16) Uani 1 1 d . . . H7 H 0.2909 -0.0100 -0.2598 0.050 Uiso 1 1 calc R . . C8 C 0.7234(6) 0.2627(6) 0.1293(5) 0.0302(12) Uani 1 1 d . . . C9 C 0.7977(7) 0.3087(7) 0.2669(6) 0.0434(17) Uani 1 1 d . . . H9 H 0.7529 0.3022 0.3273 0.052 Uiso 1 1 calc R . . C10 C 0.9345(7) 0.3619(9) 0.3077(7) 0.055(2) Uani 1 1 d . . . H10 H 0.9819 0.3893 0.3962 0.066 Uiso 1 1 calc R . . C11 C 1.0053(7) 0.3767(8) 0.2230(8) 0.0519(18) Uani 1 1 d . . . H11 H 1.0986 0.4125 0.2542 0.062 Uiso 1 1 calc R . . C12 C 0.9385(7) 0.3391(8) 0.0951(8) 0.0426(16) Uani 1 1 d . . . C13 C 1.1323(6) 0.4343(8) 0.0506(9) 0.063(2) Uani 1 1 d . . . H13A H 1.1452 0.5213 0.1283 0.095 Uiso 1 1 calc R . . H13B H 1.1557 0.4521 -0.0187 0.095 Uiso 1 1 calc R . . H13C H 1.1884 0.3858 0.0751 0.095 Uiso 1 1 calc R . . C14 C 0.7956(6) 0.2802(7) 0.0454(7) 0.0402(16) Uani 1 1 d . . . H14 H 0.7505 0.2534 -0.0436 0.048 Uiso 1 1 calc R . . C15 C 0.3577(7) 0.4555(7) 0.3962(6) 0.0387(15) Uani 1 1 d . . . C16 C 0.4285(6) 0.5219(6) 0.3287(6) 0.0312(13) Uani 1 1 d . . . C17 C 0.4350(7) 0.6577(7) 0.3504(7) 0.0434(17) Uani 1 1 d . . . H17 H 0.3981 0.7118 0.4129 0.052 Uiso 1 1 calc R . . C18 C 0.4959(8) 0.7101(9) 0.2791(8) 0.0496(19) Uani 1 1 d . . . H18 H 0.4952 0.7978 0.2903 0.059 Uiso 1 1 calc R . . C19 C 0.5579(7) 0.6361(7) 0.1916(7) 0.0437(17) Uani 1 1 d . . . H19 H 0.6011 0.6748 0.1465 0.052 Uiso 1 1 calc R . . C20 C 0.5558(7) 0.4997(7) 0.1704(6) 0.0405(16) Uani 1 1 d . . . H20 H 0.5979 0.4481 0.1124 0.049 Uiso 1 1 calc R . . C21 C 0.4899(6) 0.4474(7) 0.2382(6) 0.0338(14) Uani 1 1 d . . . O3 O 0.3124(5) 0.5219(5) 0.4835(5) 0.0485(12) Uani 1 1 d . . . H22 H 0.2778 0.5727 0.5503 0.058 Uiso 1 1 calc R . . C22 C 0.2955(6) 0.2244(7) 0.3863(6) 0.0366(14) Uani 1 1 d . . . C23 C 0.3066(8) 0.0948(8) 0.3322(7) 0.051(2) Uani 1 1 d . . . H24 H 0.3501 0.0690 0.2667 0.061 Uiso 1 1 calc R . . C24 C 0.2538(8) -0.0024(8) 0.3726(8) 0.057(2) Uani 1 1 d . . . H25 H 0.2609 -0.0920 0.3321 0.069 Uiso 1 1 calc R . . C25 C 0.1929(7) 0.0339(7) 0.4700(7) 0.0496(18) Uani 1 1 d . . . H26 H 0.1619 -0.0287 0.4999 0.060 Uiso 1 1 calc R . . C26 C 0.1772(6) 0.1654(8) 0.5247(7) 0.0427(17) Uani 1 1 d . . . C28 C 0.0700(8) 0.3115(8) 0.6646(7) 0.059(2) Uani 1 1 d . . . H28A H 0.1455 0.3941 0.7005 0.089 Uiso 1 1 calc R . . H28B H 0.0284 0.3168 0.7331 0.089 Uiso 1 1 calc R . . H28C H 0.0061 0.3046 0.5892 0.089 Uiso 1 1 calc R . . C27 C 0.2269(6) 0.2632(7) 0.4865(6) 0.0362(15) Uani 1 1 d . . . H29 H 0.2162 0.3514 0.5245 0.043 Uiso 1 1 calc R . . N3 N 0.6528(5) 0.6815(5) -0.3434(5) 0.0343(12) Uani 1 1 d . . . H30 H 0.7275 0.7115 -0.2727 0.041 Uiso 1 1 calc R . . C29 C 0.7109(6) 0.7728(5) -0.3900(6) 0.0342(13) Uani 1 1 d . . . C30 C 0.6971(8) 0.9084(8) -0.3311(8) 0.054(2) Uani 1 1 d . . . H32 H 0.6558 0.9348 -0.2637 0.064 Uiso 1 1 calc R . . C31 C 0.7452(8) 0.9993(8) -0.3747(8) 0.059(2) Uani 1 1 d . . . H33 H 0.7318 1.0863 -0.3403 0.071 Uiso 1 1 calc R . . C32 C 0.8138(7) 0.9646(8) -0.4693(7) 0.054(2) Uani 1 1 d . . . H34 H 0.8488 1.0285 -0.4963 0.064 Uiso 1 1 calc R . . C33 C 0.8291(7) 0.8350(7) -0.5222(6) 0.0423(17) Uani 1 1 d . . . C35 C 0.9345(9) 0.6875(10) -0.6596(9) 0.076(3) Uani 1 1 d . . . H36A H 0.9828 0.6831 -0.5828 0.114 Uiso 1 1 calc R . . H36B H 0.9911 0.6891 -0.7153 0.114 Uiso 1 1 calc R . . H36C H 0.8558 0.6071 -0.7108 0.114 Uiso 1 1 calc R . . C34 C 0.7779(6) 0.7386(7) -0.4811(6) 0.0390(16) Uani 1 1 d . . . H37 H 0.7902 0.6511 -0.5169 0.047 Uiso 1 1 calc R . . C36 C 0.6459(6) 0.5455(6) -0.3930(5) 0.0307(13) Uani 1 1 d . . . C38 C 0.5112(6) 0.5536(7) -0.2394(6) 0.0307(13) Uani 1 1 d . . . C39 C 0.4483(6) 0.4978(8) -0.1687(6) 0.0391(15) Uani 1 1 d . . . H40 H 0.4067 0.5478 -0.1089 0.047 Uiso 1 1 calc R . . C40 C 0.4498(7) 0.3695(8) -0.1900(7) 0.0512(19) Uani 1 1 d . . . H41 H 0.4089 0.3321 -0.1426 0.061 Uiso 1 1 calc R . . C41 C 0.5087(8) 0.2908(8) -0.2782(8) 0.0483(19) Uani 1 1 d . . . H42 H 0.5051 0.2012 -0.2925 0.058 Uiso 1 1 calc R . . C42 C 0.5735(7) 0.3480(7) -0.3453(7) 0.0423(17) Uani 1 1 d . . . H43 H 0.6165 0.2981 -0.4035 0.051 Uiso 1 1 calc R . . C43 C 0.6809(5) 0.8422(6) -0.0547(6) 0.0317(13) Uani 1 1 d . . . C45 C 0.9071(7) 0.9265(8) 0.0711(8) 0.0501(19) Uani 1 1 d . . . H45 H 0.9974 0.9375 0.0778 0.060 Uiso 1 1 calc R . . C46 C 0.8716(8) 0.9804(9) 0.1898(8) 0.054(2) Uani 1 1 d . . . H46 H 0.9374 1.0267 0.2734 0.064 Uiso 1 1 calc R . . C47 C 0.7407(7) 0.9647(7) 0.1823(7) 0.0459(17) Uani 1 1 d . . . H47 H 0.7160 0.9997 0.2607 0.055 Uiso 1 1 calc R . . C48 C 0.6426(6) 0.8956(6) 0.0560(6) 0.0313(13) Uani 1 1 d . . . C50 C 0.2762(6) 0.7322(7) -0.1313(6) 0.0371(14) Uani 1 1 d . . . C51 C 0.2050(7) 0.7165(8) -0.0473(6) 0.0393(15) Uani 1 1 d . . . H50 H 0.2505 0.7431 0.0414 0.047 Uiso 1 1 calc R . . C52 C 0.0691(7) 0.6625(8) -0.0933(8) 0.0471(18) Uani 1 1 d . . . C53 C -0.1300(6) 0.5610(10) -0.0560(10) 0.085(3) Uani 1 1 d . . . H52A H -0.1853 0.5980 -0.0992 0.127 Uiso 1 1 calc R . . H52B H -0.1600 0.5580 0.0168 0.127 Uiso 1 1 calc R . . H52C H -0.1364 0.4683 -0.1204 0.127 Uiso 1 1 calc R . . C54 C 0.0006(7) 0.6205(8) -0.2290(7) 0.055(2) Uani 1 1 d . . . H53 H -0.0923 0.5800 -0.2634 0.066 Uiso 1 1 calc R . . C55 C 0.0741(8) 0.6409(9) -0.3078(8) 0.056(2) Uani 1 1 d . . . H54 H 0.0302 0.6172 -0.3962 0.068 Uiso 1 1 calc R . . C56 C 0.2132(7) 0.6965(8) -0.2591(7) 0.0479(18) Uani 1 1 d . . . H55 H 0.2621 0.7088 -0.3145 0.058 Uiso 1 1 calc R . . O7 O 0.4580(5) 0.9286(5) 0.1389(4) 0.0510(13) Uani 1 1 d . . . H56A H 0.3665 0.9123 0.1281 0.061 Uiso 1 1 calc R . . H56B H 0.5201 0.9882 0.2237 0.061 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 Se1 0.0330(3) 0.0323(4) 0.0262(3) 0.0139(3) 0.0092(3) 0.0089(3) Se2 0.0338(4) 0.0327(4) 0.0271(3) 0.0142(3) 0.0104(3) 0.0104(3) O1 0.046(3) 0.045(2) 0.029(2) 0.0027(19) 0.0156(19) 0.013(2) O2 0.035(3) 0.087(4) 0.062(3) 0.043(3) 0.021(2) 0.017(3) N2 0.041(3) 0.035(3) 0.030(3) 0.015(2) 0.015(2) 0.013(3) O4 0.077(3) 0.061(4) 0.052(3) 0.032(3) 0.035(3) 0.016(3) O5 0.074(4) 0.064(4) 0.078(4) 0.040(3) 0.055(3) 0.023(3) O6 0.064(3) 0.037(3) 0.041(3) 0.017(2) 0.029(2) 0.019(2) N4 0.027(2) 0.040(3) 0.039(3) 0.022(2) 0.014(2) 0.013(2) O8 0.032(2) 0.082(4) 0.087(4) 0.051(4) 0.021(3) 0.015(3) N1 0.039(3) 0.033(3) 0.0194(19) 0.0082(18) 0.0070(18) 0.007(2) C37 0.037(3) 0.041(3) 0.026(3) 0.016(2) -0.001(2) 0.003(3) C44 0.037(4) 0.047(4) 0.043(4) 0.023(3) 0.007(3) 0.003(3) C49 0.037(3) 0.035(3) 0.041(3) 0.021(3) 0.013(3) 0.011(3) C1 0.041(3) 0.028(2) 0.0183(17) 0.0079(17) 0.0128(19) 0.012(2) C2 0.039(3) 0.030(3) 0.032(3) 0.016(2) 0.016(2) 0.008(2) C3 0.044(3) 0.027(3) 0.029(3) 0.014(2) 0.013(2) 0.010(2) C4 0.033(3) 0.039(3) 0.043(3) 0.017(3) 0.015(3) 0.009(3) C5 0.033(3) 0.051(4) 0.041(3) 0.020(3) -0.004(2) -0.003(3) C6 0.040(4) 0.050(4) 0.038(3) 0.015(3) -0.001(3) 0.000(3) C7 0.040(3) 0.042(3) 0.028(3) 0.012(2) 0.001(2) 0.002(3) C8 0.037(3) 0.031(3) 0.022(2) 0.0130(19) 0.0049(19) 0.013(2) C9 0.051(4) 0.055(4) 0.026(3) 0.020(3) 0.007(3) 0.024(3) C10 0.041(4) 0.067(5) 0.036(4) 0.014(3) -0.007(3) 0.019(4) C11 0.031(3) 0.061(4) 0.066(4) 0.029(3) 0.016(3) 0.019(3) C12 0.034(3) 0.045(4) 0.051(4) 0.023(4) 0.012(3) 0.019(3) C13 0.043(4) 0.074(5) 0.098(5) 0.058(4) 0.026(3) 0.025(3) C14 0.024(3) 0.046(3) 0.046(3) 0.022(3) 0.005(2) 0.006(2) C15 0.040(4) 0.040(4) 0.033(3) 0.018(3) 0.006(3) 0.011(3) C16 0.033(3) 0.029(3) 0.033(3) 0.014(2) 0.009(2) 0.013(2) C17 0.045(4) 0.036(4) 0.043(4) 0.013(3) 0.010(3) 0.015(3) C18 0.058(5) 0.041(4) 0.046(4) 0.024(3) 0.004(3) 0.014(4) C19 0.057(4) 0.035(4) 0.037(3) 0.021(3) 0.014(3) 0.004(3) C20 0.051(4) 0.035(3) 0.035(3) 0.018(3) 0.010(3) 0.010(3) C21 0.035(3) 0.031(3) 0.028(3) 0.013(2) 0.003(2) 0.004(3) O3 0.050(3) 0.052(3) 0.047(3) 0.019(2) 0.025(2) 0.027(2) C22 0.030(3) 0.053(3) 0.029(2) 0.020(2) 0.017(2) 0.010(2) C23 0.062(5) 0.047(4) 0.049(4) 0.023(4) 0.033(4) 0.013(4) C24 0.065(4) 0.047(4) 0.066(4) 0.033(3) 0.028(3) 0.007(3) C25 0.062(4) 0.038(3) 0.053(4) 0.028(3) 0.015(3) 0.012(3) C26 0.032(3) 0.058(4) 0.038(3) 0.024(3) 0.013(3) 0.009(3) C28 0.078(5) 0.053(4) 0.051(4) 0.023(3) 0.036(4) 0.019(4) C27 0.036(3) 0.046(4) 0.025(3) 0.013(3) 0.012(2) 0.018(3) N3 0.036(3) 0.035(3) 0.030(2) 0.014(2) 0.012(2) 0.011(2) C29 0.042(3) 0.025(2) 0.032(2) 0.0137(19) 0.004(2) 0.008(2) C30 0.076(5) 0.042(4) 0.064(5) 0.030(4) 0.042(4) 0.032(4) C31 0.086(5) 0.040(3) 0.066(4) 0.024(3) 0.041(4) 0.032(3) C32 0.049(4) 0.062(5) 0.051(4) 0.031(4) 0.021(3) 0.004(3) C33 0.049(4) 0.040(4) 0.031(3) 0.015(3) 0.013(3) 0.003(3) C35 0.073(6) 0.076(6) 0.081(6) 0.028(5) 0.054(5) 0.020(5) C34 0.037(3) 0.038(3) 0.039(3) 0.019(3) 0.013(3) 0.004(3) C36 0.029(3) 0.035(3) 0.025(2) 0.010(2) 0.010(2) 0.011(2) C38 0.029(3) 0.034(3) 0.025(2) 0.014(2) 0.003(2) 0.007(2) C39 0.039(3) 0.044(4) 0.031(3) 0.019(3) 0.009(3) 0.006(3) C40 0.059(4) 0.051(4) 0.047(4) 0.032(3) 0.006(3) 0.010(4) C41 0.057(5) 0.032(4) 0.053(4) 0.021(3) 0.009(4) 0.013(3) C42 0.049(4) 0.038(4) 0.041(4) 0.020(3) 0.010(3) 0.016(3) C43 0.025(3) 0.032(3) 0.033(3) 0.016(2) 0.002(2) 0.003(2) C45 0.034(3) 0.054(4) 0.065(4) 0.031(4) 0.018(3) 0.011(3) C46 0.047(4) 0.056(5) 0.044(4) 0.025(4) -0.003(3) 0.000(4) C47 0.056(4) 0.041(4) 0.034(3) 0.016(3) 0.015(3) 0.007(3) C48 0.034(3) 0.024(3) 0.028(2) 0.011(2) 0.001(2) 0.004(2) C50 0.027(3) 0.032(3) 0.049(3) 0.016(2) 0.011(2) 0.012(2) C51 0.042(3) 0.049(4) 0.035(3) 0.024(3) 0.012(2) 0.019(3) C52 0.035(4) 0.051(5) 0.061(5) 0.031(4) 0.017(3) 0.016(3) C53 0.023(3) 0.115(7) 0.124(7) 0.078(6) 0.009(4) 0.001(4) C54 0.037(3) 0.054(4) 0.054(4) 0.015(3) -0.008(3) 0.016(3) C55 0.059(5) 0.060(5) 0.045(4) 0.024(4) 0.005(3) 0.025(4) C56 0.043(4) 0.050(4) 0.046(4) 0.019(3) 0.014(3) 0.015(3) O7 0.043(3) 0.062(3) 0.037(2) 0.013(2) 0.017(2) 0.016(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 Se1 C3 1.915(6) . ? Se1 C21 1.948(7) . ? Se1 N1 2.064(5) . ? Se1 N2 2.080(5) . ? Se2 C38 1.917(7) . ? Se2 C43 1.957(5) . ? Se2 N4 2.066(5) . ? Se2 N3 2.075(5) . ? O1 C1 1.255(6) . ? O2 C12 1.374(8) . ? O2 C13 1.398(8) . ? N2 C15 1.352(9) . ? N2 C22 1.418(8) . ? O4 C26 1.366(8) . ? O4 C28 1.408(9) . ? O5 C33 1.356(8) . ? O5 C35 1.415(10) . ? O6 C36 1.237(7) . ? N4 C49 1.329(8) . ? N4 C50 1.471(7) . ? O8 C52 1.353(9) . ? O8 C53 1.454(8) . ? N1 C1 1.362(6) . ? N1 C8 1.370(8) . ? C37 C42 1.367(10) . ? C37 C38 1.378(9) . ? C37 C36 1.492(9) . ? C44 C45 1.352(9) . ? C44 C43 1.410(9) . ? C49 O7 1.190(7) . ? C49 C48 1.508(9) . ? C1 C2 1.462(8) . ? C2 C7 1.361(8) . ? C2 C3 1.426(8) . ? C3 C4 1.365(9) . ? C4 C5 1.413(8) . ? C4 H4 0.9300 . ? C5 C6 1.349(10) . ? C5 H5 0.9300 . ? C6 C7 1.404(9) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C14 1.391(9) . ? C8 C9 1.440(7) . ? C9 C10 1.365(10) . ? C9 H9 0.9300 . ? C10 C11 1.379(11) . ? C10 H10 0.9300 . ? C11 C12 1.346(10) . ? C11 H11 0.9300 . ? C12 C14 1.428(9) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14 0.9300 . ? C15 O3 1.216(8) . ? C15 C16 1.482(9) . ? C16 C21 1.390(9) . ? C16 C17 1.408(9) . ? C17 C18 1.372(11) . ? C17 H17 0.9300 . ? C18 C19 1.373(11) . ? C18 H18 0.9300 . ? C19 C20 1.425(10) . ? C19 H19 0.9300 . ? C20 C21 1.364(10) . ? C20 H20 0.9300 . ? O3 H22 0.9300 . ? C22 C23 1.346(10) . ? C22 C27 1.435(8) . ? C23 C24 1.407(10) . ? C23 H24 0.9300 . ? C24 C25 1.352(10) . ? C24 H25 0.9300 . ? C25 C26 1.385(11) . ? C25 H26 0.9300 . ? C26 C27 1.385(10) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C27 H29 0.9300 . ? N3 C36 1.351(8) . ? N3 C29 1.426(8) . ? N3 H30 0.9100 . ? C29 C34 1.341(9) . ? C29 C30 1.419(9) . ? C30 C31 1.361(10) . ? C30 H32 0.9300 . ? C31 C32 1.384(10) . ? C31 H33 0.9300 . ? C32 C33 1.365(11) . ? C32 H34 0.9300 . ? C33 C34 1.400(9) . ? C35 H36A 0.9600 . ? C35 H36B 0.9600 . ? C35 H36C 0.9600 . ? C34 H37 0.9300 . ? C38 C39 1.400(9) . ? C39 C40 1.346(10) . ? C39 H40 0.9300 . ? C40 C41 1.375(12) . ? C40 H41 0.9300 . ? C41 C42 1.383(10) . ? C41 H42 0.9300 . ? C42 H43 0.9300 . ? C43 C48 1.336(9) . ? C45 C46 1.397(11) . ? C45 H45 0.9300 . ? C46 C47 1.353(10) . ? C46 H46 0.9300 . ? C47 C48 1.399(9) . ? C47 H47 0.9300 . ? C50 C56 1.340(9) . ? C50 C51 1.377(9) . ? C51 C52 1.356(9) . ? C51 H50 0.9300 . ? C52 C54 1.415(10) . ? C53 H52A 0.9601 . ? C53 H52B 0.9601 . ? C53 H52C 0.9601 . ? C54 C55 1.361(12) . ? C54 H53 0.9300 . ? C55 C56 1.388(10) . ? C55 H54 0.9300 . ? C56 H55 0.9300 . ? O7 H56A 0.9300 . ? O7 H56B 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 Se1 C21 97.5(3) . . ? C3 Se1 N1 83.4(2) . . ? C21 Se1 N1 93.1(2) . . ? C3 Se1 N2 92.6(2) . . ? C21 Se1 N2 81.7(3) . . ? N1 Se1 N2 173.0(2) . . ? C38 Se2 C43 98.1(3) . . ? C38 Se2 N4 93.0(2) . . ? C43 Se2 N4 80.8(2) . . ? C38 Se2 N3 82.7(2) . . ? C43 Se2 N3 93.8(2) . . ? N4 Se2 N3 172.6(2) . . ? C12 O2 C13 117.7(6) . . ? C15 N2 C22 126.1(6) . . ? C15 N2 Se1 114.7(4) . . ? C22 N2 Se1 117.9(4) . . ? C26 O4 C28 119.4(6) . . ? C33 O5 C35 118.1(6) . . ? C49 N4 C50 123.5(5) . . ? C49 N4 Se2 116.5(4) . . ? C50 N4 Se2 119.8(4) . . ? C52 O8 C53 117.4(7) . . ? C1 N1 C8 124.7(5) . . ? C1 N1 Se1 112.2(4) . . ? C8 N1 Se1 122.7(3) . . ? C42 C37 C38 120.9(7) . . ? C42 C37 C36 121.4(6) . . ? C38 C37 C36 117.7(6) . . ? C45 C44 C43 115.1(6) . . ? O7 C49 N4 129.3(6) . . ? O7 C49 C48 122.2(6) . . ? N4 C49 C48 108.5(5) . . ? O1 C1 N1 125.1(6) . . ? O1 C1 C2 121.0(5) . . ? N1 C1 C2 113.9(4) . . ? C7 C2 C3 120.3(6) . . ? C7 C2 C1 123.5(6) . . ? C3 C2 C1 116.1(5) . . ? C4 C3 C2 119.6(6) . . ? C4 C3 Se1 126.6(5) . . ? C2 C3 Se1 113.5(5) . . ? C3 C4 C5 119.2(6) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 120.6(7) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.9(6) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.5 . . ? C2 C7 C6 119.2(6) . . ? C2 C7 H7 120.3 . . ? C6 C7 H7 120.6 . . ? N1 C8 C14 121.8(5) . . ? N1 C8 C9 120.2(5) . . ? C14 C8 C9 117.6(6) . . ? C10 C9 C8 119.2(6) . . ? C10 C9 H9 120.7 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 122.6(7) . . ? C9 C10 H10 118.6 . . ? C11 C10 H10 118.8 . . ? C12 C11 C10 119.6(6) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.5 . . ? C11 C12 O2 124.8(6) . . ? C11 C12 C14 120.5(7) . . ? O2 C12 C14 114.6(6) . . ? O2 C13 H13A 109.4 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 C14 C12 120.3(6) . . ? C8 C14 H14 119.9 . . ? C12 C14 H14 119.8 . . ? O3 C15 N2 129.2(7) . . ? O3 C15 C16 120.7(6) . . ? N2 C15 C16 110.2(6) . . ? C21 C16 C17 117.9(6) . . ? C21 C16 C15 119.4(6) . . ? C17 C16 C15 122.7(6) . . ? C18 C17 C16 119.8(7) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.1 . . ? C17 C18 C19 121.6(8) . . ? C17 C18 H18 119.1 . . ? C19 C18 H18 119.3 . . ? C18 C19 C20 119.7(7) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.1 . . ? C21 C20 C19 117.7(7) . . ? C21 C20 H20 121.1 . . ? C19 C20 H20 121.2 . . ? C20 C21 C16 123.3(7) . . ? C20 C21 Se1 124.0(6) . . ? C16 C21 Se1 112.7(5) . . ? C15 O3 H22 179.9 . . ? C23 C22 N2 119.5(5) . . ? C23 C22 C27 119.0(6) . . ? N2 C22 C27 121.4(6) . . ? C22 C23 C24 121.5(7) . . ? C22 C23 H24 119.2 . . ? C24 C23 H24 119.3 . . ? C25 C24 C23 120.3(7) . . ? C25 C24 H25 119.7 . . ? C23 C24 H25 120.0 . . ? C24 C25 C26 119.2(7) . . ? C24 C25 H26 120.4 . . ? C26 C25 H26 120.4 . . ? O4 C26 C25 115.3(7) . . ? O4 C26 C27 122.7(7) . . ? C25 C26 C27 121.9(6) . . ? O4 C28 H28A 109.5 . . ? O4 C28 H28B 109.6 . . ? H28A C28 H28B 109.5 . . ? O4 C28 H28C 109.3 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C27 C22 117.9(6) . . ? C26 C27 H29 121.2 . . ? C22 C27 H29 120.9 . . ? C36 N3 C29 125.3(5) . . ? C36 N3 Se2 112.7(4) . . ? C29 N3 Se2 120.6(4) . . ? C36 N3 H30 93.9 . . ? C29 N3 H30 94.0 . . ? Se2 N3 H30 94.0 . . ? C34 C29 C30 120.1(6) . . ? C34 C29 N3 124.2(5) . . ? C30 C29 N3 115.8(6) . . ? C31 C30 C29 119.0(7) . . ? C31 C30 H32 120.5 . . ? C29 C30 H32 120.5 . . ? C30 C31 C32 121.2(7) . . ? C30 C31 H33 119.3 . . ? C32 C31 H33 119.5 . . ? C33 C32 C31 118.8(7) . . ? C33 C32 H34 120.6 . . ? C31 C32 H34 120.6 . . ? O5 C33 C32 114.5(6) . . ? O5 C33 C34 124.5(7) . . ? C32 C33 C34 121.0(6) . . ? O5 C35 H36A 109.6 . . ? O5 C35 H36B 109.4 . . ? H36A C35 H36B 109.5 . . ? O5 C35 H36C 109.4 . . ? H36A C35 H36C 109.5 . . ? H36B C35 H36C 109.5 . . ? C29 C34 C33 119.7(6) . . ? C29 C34 H37 120.3 . . ? C33 C34 H37 119.9 . . ? O6 C36 N3 126.5(6) . . ? O6 C36 C37 121.7(6) . . ? N3 C36 C37 111.8(5) . . ? C37 C38 C39 119.8(7) . . ? C37 C38 Se2 113.9(5) . . ? C39 C38 Se2 126.2(5) . . ? C40 C39 C38 117.9(7) . . ? C40 C39 H40 121.0 . . ? C38 C39 H40 121.1 . . ? C39 C40 C41 123.3(8) . . ? C39 C40 H41 118.4 . . ? C41 C40 H41 118.3 . . ? C40 C41 C42 118.5(7) . . ? C40 C41 H42 120.7 . . ? C42 C41 H42 120.8 . . ? C37 C42 C41 119.6(7) . . ? C37 C42 H43 120.2 . . ? C41 C42 H43 120.2 . . ? C48 C43 C44 124.0(6) . . ? C48 C43 Se2 113.3(4) . . ? C44 C43 Se2 122.7(5) . . ? C44 C45 C46 122.9(7) . . ? C44 C45 H45 118.5 . . ? C46 C45 H45 118.6 . . ? C47 C46 C45 119.5(7) . . ? C47 C46 H46 120.3 . . ? C45 C46 H46 120.2 . . ? C46 C47 C48 119.8(7) . . ? C46 C47 H47 119.9 . . ? C48 C47 H47 120.3 . . ? C43 C48 C47 118.6(6) . . ? C43 C48 C49 120.2(5) . . ? C47 C48 C49 121.1(6) . . ? C56 C50 C51 121.1(6) . . ? C56 C50 N4 118.2(6) . . ? C51 C50 N4 120.7(6) . . ? C52 C51 C50 120.4(6) . . ? C52 C51 H50 119.8 . . ? C50 C51 H50 119.7 . . ? O8 C52 C51 115.8(7) . . ? O8 C52 C54 124.6(6) . . ? C51 C52 C54 119.5(7) . . ? O8 C53 H52A 109.5 . . ? O8 C53 H52B 109.5 . . ? H52A C53 H52B 109.5 . . ? O8 C53 H52C 109.4 . . ? H52A C53 H52C 109.5 . . ? H52B C53 H52C 109.5 . . ? C55 C54 C52 118.3(6) . . ? C55 C54 H53 120.6 . . ? C52 C54 H53 121.1 . . ? C54 C55 C56 121.4(7) . . ? C54 C55 H54 119.2 . . ? C56 C55 H54 119.4 . . ? C50 C56 C55 119.3(7) . . ? C50 C56 H55 120.7 . . ? C55 C56 H55 120.0 . . ? C49 O7 H56A 119.8 . . ? C49 O7 H56B 120.2 . . ? H56A O7 H56B 120.0 . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 33.27 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.384 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.056 # Attachment 'DSBr.cif' data_c18 _database_code_depnum_ccdc_archive 'CCDC 869455' #TrackingRef 'DSBr.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H16 Br2 N2 O6 Se' _chemical_formula_sum 'C27 H16 Br2 N2 O6 Se' _chemical_formula_weight 703.20 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' Br Br -0.2901 2.4595 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 21.023(2) _cell_length_b 13.153(2) _cell_length_c 11.8836(18) _cell_angle_alpha 90.00 _cell_angle_beta 121.836(7) _cell_angle_gamma 90.00 _cell_volume 2791.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.673 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 4.250 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5105 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 10237 _diffrn_reflns_av_R_equivalents 0.0803 _diffrn_reflns_av_sigmaI/netI 0.1168 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.59 _reflns_number_total 3218 _reflns_number_gt 1501 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1999)' _computing_publication_material WinGX _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^ > 2\s(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^)+(0.0875P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3218 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1612 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1843 _refine_ls_wR_factor_gt 0.1485 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 0.961 _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 Se1 Se 0.5000 0.06856(6) 0.7500 0.0513(3) Uani 1 2 d S . . Br1 Br 0.84081(6) -0.19680(7) 0.90628(13) 0.1304(5) Uani 1 1 d . . . N1 N 0.5670(3) 0.0780(3) 0.6712(5) 0.0535(12) Uani 1 1 d . . . O1 O 0.5505(2) 0.1143(4) 0.4667(4) 0.0784(13) Uani 1 1 d . . . O2 O 0.4676(6) 0.4467(7) 0.8254(12) 0.229(5) Uani 1 1 d . . . O3 O 0.5756(11) 0.5526(12) 0.8217(13) 0.460(16) Uani 1 1 d . . . C1 C 0.4394(3) 0.1641(4) 0.6085(6) 0.0539(15) Uani 1 1 d . . . C2 C 0.3773(4) 0.2128(5) 0.5936(7) 0.0728(19) Uani 1 1 d . . . H2 H 0.3620 0.2038 0.6536 0.087 Uiso 1 1 calc R . . C3 C 0.3388(4) 0.2758(6) 0.4842(9) 0.096(3) Uani 1 1 d . . . H3 H 0.2969 0.3111 0.4702 0.115 Uiso 1 1 calc R . . C4 C 0.3621(5) 0.2867(6) 0.3958(8) 0.102(3) Uani 1 1 d . . . H4 H 0.3355 0.3298 0.3235 0.123 Uiso 1 1 calc R . . C5 C 0.4232(4) 0.2359(6) 0.4115(8) 0.084(2) Uani 1 1 d . . . H5 H 0.4371 0.2424 0.3495 0.101 Uiso 1 1 calc R . . C6 C 0.4636(4) 0.1748(4) 0.5220(7) 0.0608(17) Uani 1 1 d . . . C7 C 0.5305(3) 0.1198(4) 0.5470(6) 0.0563(15) Uani 1 1 d . . . C8 C 0.6318(3) 0.0175(4) 0.7249(6) 0.0565(15) Uani 1 1 d . . . C9 C 0.6498(4) -0.0491(6) 0.8292(7) 0.087(2) Uani 1 1 d . . . H9 H 0.6180 -0.0531 0.8613 0.104 Uiso 1 1 calc R . . C10 C 0.7124(4) -0.1085(6) 0.8856(8) 0.092(2) Uani 1 1 d . . . H10 H 0.7236 -0.1500 0.9571 0.110 Uiso 1 1 calc R . . C11 C 0.7590(4) -0.1071(6) 0.8373(8) 0.082(2) Uani 1 1 d . . . C12 C 0.7443(4) -0.0431(6) 0.7374(9) 0.093(3) Uani 1 1 d . . . H12 H 0.7763 -0.0414 0.7055 0.111 Uiso 1 1 calc R . . C13 C 0.6820(4) 0.0200(5) 0.6819(8) 0.076(2) Uani 1 1 d . . . H13 H 0.6736 0.0648 0.6149 0.092 Uiso 1 1 calc R . . C14 C 0.5000 0.4939(11) 0.7500 0.134(5) Uani 1 2 d S . . 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 Se1 0.0470(5) 0.0520(5) 0.0688(6) 0.000 0.0402(5) 0.000 Br1 0.1028(8) 0.1084(8) 0.2182(13) 0.0377(7) 0.1108(9) 0.0471(6) N1 0.050(3) 0.055(3) 0.073(3) -0.001(3) 0.044(3) -0.001(2) O1 0.074(3) 0.106(3) 0.076(3) -0.003(3) 0.054(3) -0.013(3) O2 0.286(13) 0.205(8) 0.341(13) -0.004(9) 0.265(12) -0.022(9) O3 0.57(4) 0.49(3) 0.210(15) -0.050(15) 0.125(17) -0.24(3) C1 0.050(4) 0.046(3) 0.064(4) 0.003(3) 0.030(3) 0.000(3) C2 0.059(4) 0.067(4) 0.097(5) 0.014(4) 0.044(4) 0.009(4) C3 0.064(5) 0.097(6) 0.127(7) 0.041(5) 0.050(5) 0.024(4) C4 0.082(6) 0.107(7) 0.103(7) 0.045(5) 0.039(5) 0.007(5) C5 0.068(5) 0.095(5) 0.090(5) 0.025(5) 0.043(4) 0.006(5) C6 0.056(4) 0.056(4) 0.081(5) 0.005(3) 0.044(4) -0.006(3) C7 0.056(4) 0.055(4) 0.069(4) -0.003(3) 0.041(4) -0.013(3) C8 0.057(4) 0.057(4) 0.076(4) -0.010(3) 0.049(4) -0.010(3) C9 0.077(5) 0.107(6) 0.108(6) 0.028(5) 0.071(5) 0.036(4) C10 0.085(6) 0.108(6) 0.107(6) 0.032(5) 0.068(5) 0.040(5) C11 0.079(5) 0.074(5) 0.124(6) 0.016(5) 0.074(5) 0.017(4) C12 0.081(6) 0.082(5) 0.159(8) 0.004(5) 0.092(6) 0.011(5) C13 0.073(5) 0.072(5) 0.111(6) 0.007(4) 0.067(4) 0.001(4) C14 0.147(14) 0.092(10) 0.167(15) 0.000 0.085(13) 0.000 _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Se1 C1 1.941(6) 2_656 ? Se1 C1 1.941(6) . ? Se1 N1 2.067(4) . ? Se1 N1 2.067(4) 2_656 ? Br1 C11 1.881(7) . ? N1 C7 1.369(7) . ? N1 C8 1.406(8) . ? O1 C7 1.231(6) . ? O2 C14 1.515(9) . ? O3 C14 1.555(17) . ? C1 C6 1.373(8) . ? C1 C2 1.381(9) . ? C2 C3 1.387(10) . ? C3 C4 1.379(11) . ? C4 C5 1.371(10) . ? C5 C6 1.384(9) . ? C6 C7 1.466(8) . ? C8 C13 1.396(8) . ? C8 C9 1.397(9) . ? C9 C10 1.365(9) . ? C10 C11 1.371(9) . ? C11 C12 1.351(10) . ? C12 C13 1.389(9) . ? C14 O2 1.515(9) 2_656 ? C14 O3 1.555(17) 2_656 ? 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 Se1 C1 99.3(3) 2_656 . ? C1 Se1 N1 93.5(2) 2_656 . ? C1 Se1 N1 82.0(2) . . ? C1 Se1 N1 82.0(2) 2_656 2_656 ? C1 Se1 N1 93.5(2) . 2_656 ? N1 Se1 N1 173.1(3) . 2_656 ? C7 N1 C8 125.2(5) . . ? C7 N1 Se1 112.5(4) . . ? C8 N1 Se1 119.2(4) . . ? C6 C1 C2 123.7(6) . . ? C6 C1 Se1 112.5(4) . . ? C2 C1 Se1 123.7(5) . . ? C1 C2 C3 116.2(7) . . ? C4 C3 C2 120.7(7) . . ? C5 C4 C3 121.9(7) . . ? C4 C5 C6 118.3(7) . . ? C1 C6 C5 119.1(6) . . ? C1 C6 C7 119.4(6) . . ? C5 C6 C7 121.4(6) . . ? O1 C7 N1 125.8(6) . . ? O1 C7 C6 123.8(6) . . ? N1 C7 C6 110.5(5) . . ? C13 C8 C9 115.9(6) . . ? C13 C8 N1 123.9(6) . . ? C9 C8 N1 120.2(5) . . ? C10 C9 C8 122.3(6) . . ? C9 C10 C11 120.2(7) . . ? C12 C11 C10 119.6(7) . . ? C12 C11 Br1 120.4(5) . . ? C10 C11 Br1 120.0(6) . . ? C11 C12 C13 120.7(6) . . ? C12 C13 C8 121.2(7) . . ? O2 C14 O2 131.7(12) 2_656 . ? O2 C14 O3 83.1(8) 2_656 . ? O2 C14 O3 121.8(7) . . ? O2 C14 O3 121.8(7) 2_656 2_656 ? O2 C14 O3 83.1(8) . 2_656 ? O3 C14 O3 120.4(18) . 2_656 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.565 _refine_diff_density_min -0.628 _refine_diff_density_rms 0.097 # Attachment 'SeAr4Ch3.cif' data_dssear4ch3_0m _database_code_depnum_ccdc_archive 'CCDC 869456' #TrackingRef 'SeAr4Ch3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 N2 O2 Se' _chemical_formula_sum 'C28 H24 N2 O2 Se' _chemical_formula_weight 499.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C12/c1 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 27.425(6) _cell_length_b 5.1133(9) _cell_length_c 17.468(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.987(13) _cell_angle_gamma 90.00 _cell_volume 2302.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'needle shape' _exptl_crystal_colour white _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 1.660 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.7629 _exptl_absorpt_correction_T_max 0.9058 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 scan' _diffrn_detector_area_resol_mean 0.3 _diffrn_reflns_number 27185 _diffrn_reflns_av_R_equivalents 0.0657 _diffrn_reflns_av_sigmaI/netI 0.0883 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 36.71 _reflns_number_total 5162 _reflns_number_gt 2444 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker kappa apex ccd' _computing_cell_refinement 'Bruker kappa apex ccd' _computing_data_reduction 'Bruker saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ortep-III _computing_publication_material WinGX1.80.05 _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^)+(0.0793P)^2^+0.0771P] 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 5162 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1427 _refine_ls_R_factor_gt 0.0513 _refine_ls_wR_factor_ref 0.1565 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 0.930 _refine_ls_restrained_S_all 0.930 _refine_ls_shift/su_max 0.195 _refine_ls_shift/su_mean 0.006 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.0000 -0.25137(6) 0.2500 0.03555(13) Uani 1 2 d S . . O1 O 0.03882(7) -0.1352(3) 0.09841(12) 0.0445(4) Uani 1 1 d . . . N1 N 0.05985(8) 0.2940(3) 0.12236(13) 0.0323(5) Uani 1 1 d . . . H1 H 0.0476 0.4444 0.1285 0.039 Uiso 1 1 calc R . . C1 C -0.04157(8) 0.0059(4) 0.17578(14) 0.0292(5) Uani 1 1 d . . . C2 C -0.08991(9) 0.0634(5) 0.17958(16) 0.0389(6) Uani 1 1 d . . . H2 H -0.1025 -0.0330 0.2140 0.047 Uiso 1 1 calc R . . C3 C -0.11969(10) 0.2604(5) 0.1334(2) 0.0456(7) Uani 1 1 d . . . H3 H -0.1521 0.2964 0.1368 0.055 Uiso 1 1 calc R . . C4 C -0.10162(9) 0.4054(5) 0.08201(17) 0.0434(6) Uani 1 1 d . . . H4 H -0.1218 0.5393 0.0509 0.052 Uiso 1 1 calc R . . C5 C -0.05360(9) 0.3513(5) 0.07694(15) 0.0358(5) Uani 1 1 d . . . H5 H -0.0413 0.4506 0.0428 0.043 Uiso 1 1 calc R . . C6 C -0.02325(8) 0.1493(4) 0.12258(13) 0.0273(4) Uani 1 1 d . . . C7 C 0.02771(8) 0.0873(4) 0.11320(13) 0.0287(5) Uani 1 1 d . . . C8 C 0.11133(9) 0.2885(4) 0.12289(16) 0.0322(5) Uani 1 1 d . . . C9 C 0.12906(10) 0.1059(5) 0.07974(17) 0.0456(6) Uani 1 1 d . . . H9 H 0.1068 -0.0226 0.0494 0.055 Uiso 1 1 calc R . . C10 C 0.17952(11) 0.1153(6) 0.0820(2) 0.0561(8) Uani 1 1 d . . . H10 H 0.1910 -0.0097 0.0533 0.067 Uiso 1 1 calc R . . C11 C 0.21399(11) 0.3047(6) 0.1255(2) 0.0522(8) Uani 1 1 d . . . C12 C 0.26913(13) 0.3161(9) 0.1260(3) 0.0826(12) Uani 1 1 d . . . H12A H 0.2709 0.4301 0.0834 0.124 Uiso 1 1 calc R . . H12B H 0.2802 0.1438 0.1174 0.124 Uiso 1 1 calc R . . H12C H 0.2914 0.3815 0.1776 0.124 Uiso 1 1 calc R . . C13 C 0.19570(10) 0.4861(6) 0.1672(2) 0.0610(8) Uani 1 1 d . . . H13 H 0.2178 0.6165 0.1967 0.073 Uiso 1 1 calc R . . C14 C 0.14545(10) 0.4786(6) 0.16610(19) 0.0503(7) Uani 1 1 d . . . H14 H 0.1342 0.6036 0.1950 0.060 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.0424(2) 0.02518(17) 0.0395(2) 0.000 0.01461(16) 0.000 O1 0.0535(11) 0.0222(8) 0.0719(13) -0.0036(8) 0.0398(10) -0.0013(8) N1 0.0302(10) 0.0222(9) 0.0470(13) -0.0032(7) 0.0163(9) -0.0002(7) C1 0.0267(10) 0.0244(10) 0.0356(12) -0.0031(9) 0.0093(9) -0.0016(8) C2 0.0311(12) 0.0417(13) 0.0462(15) 0.0011(11) 0.0160(11) -0.0029(10) C3 0.0281(12) 0.0481(16) 0.0610(19) -0.0013(13) 0.0158(12) 0.0050(10) C4 0.0339(13) 0.0386(14) 0.0501(16) 0.0026(11) 0.0046(12) 0.0102(10) C5 0.0378(13) 0.0314(11) 0.0361(14) 0.0005(10) 0.0098(11) 0.0001(10) C6 0.0287(11) 0.0208(9) 0.0320(12) -0.0041(9) 0.0099(9) -0.0017(8) C7 0.0332(11) 0.0249(10) 0.0313(12) -0.0003(9) 0.0153(9) -0.0009(8) C8 0.0320(11) 0.0283(12) 0.0382(13) 0.0060(9) 0.0144(10) 0.0002(8) C9 0.0440(14) 0.0407(15) 0.0615(18) -0.0073(12) 0.0300(13) -0.0061(11) C10 0.0512(17) 0.0546(19) 0.076(2) 0.0040(16) 0.0398(16) 0.0074(14) C11 0.0319(13) 0.064(2) 0.063(2) 0.0201(15) 0.0196(13) 0.0041(12) C12 0.0388(17) 0.109(3) 0.105(3) 0.012(3) 0.032(2) 0.0027(18) C13 0.0373(15) 0.0620(19) 0.079(2) -0.0019(17) 0.0143(15) -0.0137(13) C14 0.0373(14) 0.0467(15) 0.0672(19) -0.0125(14) 0.0181(13) -0.0062(11) _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 Se1 C1 1.924(2) 2 ? Se1 C1 1.924(2) . ? O1 C7 1.228(3) . ? N1 C7 1.350(3) . ? N1 C8 1.409(3) . ? N1 H1 0.8600 . ? C1 C2 1.382(3) . ? C1 C6 1.404(3) . ? C2 C3 1.372(4) . ? C2 H2 0.9300 . ? C3 C4 1.380(4) . ? C3 H3 0.9300 . ? C4 C5 1.378(3) . ? C4 H4 0.9300 . ? C5 C6 1.394(3) . ? C5 H5 0.9300 . ? C6 C7 1.496(3) . ? C8 C14 1.381(3) . ? C8 C9 1.388(4) . ? C9 C10 1.372(4) . ? C9 H9 0.9300 . ? C10 C11 1.385(5) . ? C10 H10 0.9300 . ? C11 C13 1.376(4) . ? C11 C12 1.510(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.372(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Se1 C1 93.72(13) 2 . ? C7 N1 C8 126.68(19) . . ? C7 N1 H1 116.7 . . ? C8 N1 H1 116.7 . . ? C2 C1 C6 119.1(2) . . ? C2 C1 Se1 118.07(18) . . ? C6 C1 Se1 122.62(16) . . ? C3 C2 C1 121.1(2) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C2 C3 C4 120.2(2) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.8(2) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 119.1(2) . . ? C5 C6 C7 119.5(2) . . ? C1 C6 C7 121.4(2) . . ? O1 C7 N1 123.5(2) . . ? O1 C7 C6 121.9(2) . . ? N1 C7 C6 114.69(18) . . ? C14 C8 C9 118.2(2) . . ? C14 C8 N1 118.7(2) . . ? C9 C8 N1 123.1(2) . . ? C10 C9 C8 119.9(3) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 122.2(3) . . ? C9 C10 H10 118.9 . . ? C11 C10 H10 118.9 . . ? C13 C11 C10 117.3(3) . . ? C13 C11 C12 121.1(3) . . ? C10 C11 C12 121.7(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C11 121.3(3) . . ? C14 C13 H13 119.3 . . ? C11 C13 H13 119.3 . . ? C13 C14 C8 121.1(3) . . ? C13 C14 H14 119.4 . . ? C8 C14 H14 119.4 . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 36.71 _diffrn_measured_fraction_theta_full 0.898 _refine_diff_density_max 0.440 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.097 _atom_sites_special_details ; The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.2, Nqual = 0, Ralpha = 0.055 ; # Attachment 'SeNHOMe.cif' data_c20 _database_code_depnum_ccdc_archive 'CCDC 869457' #TrackingRef 'SeNHOMe.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 N2 O4 Se' _chemical_formula_sum 'C28 H N2 O4 Se' _chemical_formula_weight 532.27 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 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 10.1344(3) _cell_length_b 10.3521(3) _cell_length_c 12.1801(4) _cell_angle_alpha 82.512(2) _cell_angle_beta 78.896(2) _cell_angle_gamma 79.956(2) _cell_volume 1228.50(6) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1079.8 _exptl_absorpt_coefficient_mu 1.563 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5105 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 25054 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0527 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 30.97 _reflns_number_total 13330 _reflns_number_gt 9202 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1999)' _computing_publication_material WinGX _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^)+(0.0537P)^2^+0.3255P] 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 0.38(2) _refine_ls_number_reflns 13330 _refine_ls_number_parameters 634 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 4.433 _refine_ls_shift/su_mean 0.394 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 Se1 Se 0.35171(3) 0.41207(3) 1.06609(3) 0.0436(2) Uani 1 1 d . . . Se2 Se 0.64564(3) 0.56320(3) -0.06441(3) 0.0433(2) Uani 1 1 d . . . N1 N -0.0472(6) 0.6347(7) 1.2204(6) 0.0388(15) Uani 1 1 d . . . N2 N 0.5319(6) 0.4388(6) 0.7350(5) 0.0426(16) Uani 1 1 d . . . O3 O 0.2323(8) 0.6734(8) 0.4758(6) 0.073(2) Uani 1 1 d . . . N3 N 0.4731(4) 0.5381(6) 0.2663(5) 0.0339(13) Uani 1 1 d . . . O5 O 0.7671(7) 0.3037(8) 0.5224(6) 0.073(2) Uani 1 1 d . . . O6 O 0.6733(6) 0.6060(7) 0.2001(6) 0.0601(18) Uani 1 1 d . . . O7 O 0.8650(7) -0.0105(6) -0.3389(6) 0.0645(18) Uani 1 1 d . . . O8 O 0.8164(6) 0.4015(6) -0.2046(6) 0.0549(17) Uani 1 1 d . . . O2 O 0.1794(6) 0.5715(6) 1.2097(6) 0.0612(18) Uani 1 1 d . . . C90 C 0.1153(15) 1.1210(11) 1.3700(12) 0.090(4) Uani 1 1 d . . . O1 O 0.3210(5) 0.3691(7) 0.7983(6) 0.0549(16) Uani 1 1 d . . . N4 N 1.0448(5) 0.3363(6) -0.2165(6) 0.0388(14) Uani 1 1 d . . . H4A H 1.0823 0.3186 -0.1539 0.047 Uiso 1 1 calc R . . H4B H 1.1002 0.3837 -0.2662 0.047 Uiso 1 1 calc R . . C1 C 0.1761(7) 0.3574(8) 1.0845(6) 0.0337(16) Uani 1 1 d . . . C2 C 0.0574(7) 0.4306(7) 1.1403(6) 0.0319(15) Uani 1 1 d . . . C3 C -0.0669(7) 0.3861(9) 1.1483(7) 0.044(2) Uani 1 1 d . . . H3 H -0.1452 0.4338 1.1859 0.053 Uiso 1 1 calc R . . C4 C -0.0776(7) 0.2789(9) 1.1044(8) 0.047(2) Uani 1 1 d . . . H4 H -0.1622 0.2528 1.1106 0.056 Uiso 1 1 calc R . . C5 C 0.0399(9) 0.2044(9) 1.0483(8) 0.048(2) Uani 1 1 d . . . H5 H 0.0334 0.1282 1.0182 0.057 Uiso 1 1 calc R . . C6 C 0.1611(8) 0.2439(7) 1.0383(7) 0.0410(18) Uani 1 1 d . . . H6 H 0.2377 0.1949 0.9998 0.049 Uiso 1 1 calc R . . C7 C 0.0689(7) 0.5537(8) 1.1936(7) 0.0341(17) Uani 1 1 d . . . C8 C -0.0639(7) 0.7604(8) 1.2593(6) 0.0362(17) Uani 1 1 d . . . C9 C 0.0433(8) 0.8162(8) 1.2826(8) 0.045(2) Uani 1 1 d . . . H9 H 0.1312 0.7695 1.2734 0.054 Uiso 1 1 calc R . . C10 C 0.0179(10) 0.9410(9) 1.3191(7) 0.046(2) Uani 1 1 d . . . C11 C -0.1135(10) 1.0096(10) 1.3346(8) 0.058(2) Uani 1 1 d . . . H11 H -0.1301 1.0943 1.3571 0.070 Uiso 1 1 calc R . . C12 C -0.2161(10) 0.9540(10) 1.3172(10) 0.079(3) Uani 1 1 d . . . H12 H -0.3048 0.9972 1.3350 0.095 Uiso 1 1 calc R . . C13 C -0.1938(9) 0.8337(10) 1.2735(9) 0.064(3) Uani 1 1 d . . . H13 H -0.2654 0.8019 1.2536 0.076 Uiso 1 1 calc R . . O10 O 0.1276(7) 0.9859(7) 1.3352(7) 0.081(2) Uani 1 1 d . . . C15 C 0.4703(7) 0.2646(8) 1.0023(6) 0.0398(18) Uani 1 1 d . . . C16 C 0.5350(9) 0.1682(9) 1.0697(8) 0.049(2) Uani 1 1 d . . . H16 H 0.5100 0.1674 1.1473 0.059 Uiso 1 1 calc R . . C17 C 0.6375(9) 0.0709(9) 1.0253(9) 0.058(3) Uani 1 1 d . . . H17 H 0.6826 0.0079 1.0726 0.069 Uiso 1 1 calc R . . C18 C 0.6700(9) 0.0697(9) 0.9124(7) 0.052(2) Uani 1 1 d . . . H18 H 0.7354 0.0024 0.8831 0.062 Uiso 1 1 calc R . . C19 C 0.6117(6) 0.1617(7) 0.8408(7) 0.0387(19) Uani 1 1 d . . . H19 H 0.6390 0.1593 0.7636 0.046 Uiso 1 1 calc R . . C20 C 0.5077(6) 0.2630(7) 0.8840(6) 0.0317(16) Uani 1 1 d . . . C21 C 0.4445(7) 0.3645(8) 0.8033(6) 0.0376(18) Uani 1 1 d . . . C22 C 0.4909(7) 0.5453(8) 0.6565(6) 0.0377(18) Uani 1 1 d . . . C23 C 0.5725(9) 0.6434(9) 0.6271(7) 0.053(2) Uani 1 1 d . . . H23 H 0.6494 0.6410 0.6588 0.063 Uiso 1 1 calc R . . C24 C 0.5346(11) 0.7436(11) 0.5493(9) 0.066(3) Uani 1 1 d . . . H24 H 0.5895 0.8088 0.5273 0.079 Uiso 1 1 calc R . . C25 C 0.4203(12) 0.7539(10) 0.5015(8) 0.061(3) Uani 1 1 d . . . H25 H 0.3972 0.8258 0.4509 0.074 Uiso 1 1 calc R . . C26 C 0.3402(9) 0.6546(9) 0.5305(7) 0.0482(19) Uani 1 1 d . . . C27 C 0.3728(8) 0.5519(9) 0.6070(7) 0.0408(19) Uani 1 1 d . . . H27 H 0.3184 0.4860 0.6270 0.049 Uiso 1 1 calc R . . C28 C 0.1437(9) 0.5831(10) 0.5099(8) 0.071(3) Uani 1 1 d . . . H28A H 0.1923 0.4958 0.5009 0.107 Uiso 1 1 calc R . . H28B H 0.0732 0.6011 0.4651 0.107 Uiso 1 1 calc R . . H28C H 0.1039 0.5895 0.5876 0.107 Uiso 1 1 calc R . . C29 C 0.5265(6) 0.7100(7) 0.0040(6) 0.0347(16) Uani 1 1 d . . . C30 C 0.4855(7) 0.7145(8) 0.1170(7) 0.0356(17) Uani 1 1 d . . . C31 C 0.5546(7) 0.6165(7) 0.1983(6) 0.0327(16) Uani 1 1 d . . . C32 C 0.5117(8) 0.4305(8) 0.3457(7) 0.0422(19) Uani 1 1 d . . . C33 C 0.6232(8) 0.4231(9) 0.3943(7) 0.045(2) Uani 1 1 d . . . H33 H 0.6784 0.4885 0.3766 0.054 Uiso 1 1 calc R . . C34 C 0.6528(9) 0.3143(10) 0.4716(7) 0.058(2) Uani 1 1 d . . . C35 C 0.5722(12) 0.2198(11) 0.5020(9) 0.071(3) Uani 1 1 d . . . H35 H 0.5929 0.1503 0.5556 0.085 Uiso 1 1 calc R . . C36 C 0.4593(13) 0.2276(11) 0.4531(9) 0.073(3) Uani 1 1 d . . . H36 H 0.4038 0.1626 0.4714 0.087 Uiso 1 1 calc R . . C37 C 0.4295(9) 0.3364(10) 0.3746(8) 0.057(3) Uani 1 1 d . . . H37 H 0.3523 0.3440 0.3421 0.068 Uiso 1 1 calc R . . C38 C 0.8602(10) 0.3991(11) 0.4929(10) 0.082(3) Uani 1 1 d . . . H38A H 0.8891 0.4087 0.4129 0.123 Uiso 1 1 calc R . . H38B H 0.9380 0.3693 0.5289 0.123 Uiso 1 1 calc R . . H38C H 0.8151 0.4826 0.5175 0.123 Uiso 1 1 calc R . . C39 C 0.3893(8) 0.8134(8) 0.1571(8) 0.047(2) Uani 1 1 d . . . H39 H 0.3654 0.8175 0.2343 0.056 Uiso 1 1 calc R . . C40 C 0.3245(8) 0.9105(8) 0.0840(8) 0.055(2) Uani 1 1 d . . . H40 H 0.2562 0.9766 0.1116 0.066 Uiso 1 1 calc R . . C41 C 0.3665(9) 0.9035(9) -0.0303(7) 0.053(2) Uani 1 1 d . . . H41 H 0.3271 0.9675 -0.0802 0.064 Uiso 1 1 calc R . . C42 C 0.4643(8) 0.8050(9) -0.0721(8) 0.048(2) Uani 1 1 d . . . H42 H 0.4893 0.8006 -0.1492 0.057 Uiso 1 1 calc R . . C43 C 0.8205(7) 0.6176(8) -0.0815(6) 0.0308(16) Uani 1 1 d . . . C44 C 0.9366(6) 0.5419(8) -0.1387(6) 0.0341(16) Uani 1 1 d . . . C45 C 0.9260(7) 0.4231(8) -0.1881(6) 0.0380(18) Uani 1 1 d . . . C46 C 1.0596(8) 0.2119(7) -0.2608(6) 0.0415(18) Uani 1 1 d . . . C47 C 1.1938(7) 0.1430(9) -0.2793(9) 0.058(2) Uani 1 1 d . . . H47 H 1.2665 0.1819 -0.2701 0.070 Uiso 1 1 calc R . . C48 C 1.2149(10) 0.0185(11) -0.3108(9) 0.067(3) Uani 1 1 d . . . H48 H 1.3014 -0.0307 -0.3145 0.081 Uiso 1 1 calc R . . C49 C 1.1091(9) -0.0390(9) -0.3383(8) 0.057(2) Uani 1 1 d . . . H49 H 1.1261 -0.1205 -0.3670 0.068 Uiso 1 1 calc R . . C50 C 0.9800(10) 0.0328(9) -0.3200(8) 0.050(2) Uani 1 1 d . . . C51 C 0.8800(12) -0.1394(9) -0.3616(9) 0.068(3) Uani 1 1 d . . . H51A H 0.9424 -0.1516 -0.4308 0.101 Uiso 1 1 calc R . . H51B H 0.7933 -0.1601 -0.3682 0.101 Uiso 1 1 calc R . . H51C H 0.9147 -0.1965 -0.3015 0.101 Uiso 1 1 calc R . . C52 C 0.9571(9) 0.1574(8) -0.2818(7) 0.044(2) Uani 1 1 d . . . H52 H 0.8691 0.2038 -0.2706 0.053 Uiso 1 1 calc R . . C53 C 1.0618(8) 0.5853(8) -0.1469(7) 0.0415(18) Uani 1 1 d . . . H53 H 1.1402 0.5369 -0.1836 0.050 Uiso 1 1 calc R . . C54 C 1.0722(9) 0.7015(9) -0.1005(7) 0.050(2) Uani 1 1 d . . . H54 H 1.1562 0.7293 -0.1075 0.060 Uiso 1 1 calc R . . C55 C 0.9591(8) 0.7707(9) -0.0465(7) 0.045(2) Uani 1 1 d . . . H55 H 0.9650 0.8468 -0.0157 0.055 Uiso 1 1 calc R . . C56 C 0.8307(7) 0.7289(8) -0.0359(7) 0.0382(17) Uani 1 1 d . . . H56 H 0.7532 0.7771 0.0022 0.046 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 Se1 0.0295(4) 0.0459(5) 0.0576(6) -0.0218(4) -0.0037(4) -0.0037(4) Se2 0.0294(4) 0.0444(5) 0.0583(6) -0.0226(4) -0.0041(4) -0.0031(4) N1 0.034(3) 0.035(4) 0.039(4) -0.006(3) 0.005(3) 0.004(3) N2 0.052(3) 0.039(4) 0.034(3) -0.006(3) 0.002(2) -0.010(3) O3 0.077(5) 0.085(5) 0.053(4) 0.009(4) -0.029(4) 0.003(4) N3 0.0146(16) 0.045(3) 0.044(3) 0.000(3) -0.0153(18) -0.0029(19) O5 0.064(4) 0.088(6) 0.066(5) 0.013(4) -0.034(4) 0.002(4) O6 0.033(3) 0.076(4) 0.069(4) 0.018(3) -0.019(3) -0.008(3) O7 0.067(4) 0.051(4) 0.082(4) -0.019(3) -0.022(3) -0.008(3) O8 0.028(3) 0.058(4) 0.084(5) -0.034(3) -0.010(3) 0.001(3) O2 0.034(3) 0.059(4) 0.099(5) -0.047(4) -0.018(3) 0.008(3) C90 0.125(9) 0.045(6) 0.107(9) -0.024(6) -0.025(7) -0.015(6) O1 0.022(2) 0.064(4) 0.077(4) 0.011(3) -0.014(2) -0.008(2) N4 0.025(2) 0.044(4) 0.050(3) -0.005(3) -0.016(2) -0.002(2) C1 0.032(3) 0.033(4) 0.036(4) 0.005(3) -0.013(3) -0.005(3) C2 0.033(3) 0.031(3) 0.030(4) -0.009(3) -0.004(3) 0.002(3) C3 0.025(3) 0.057(5) 0.048(5) 0.002(4) 0.001(3) -0.010(3) C4 0.030(3) 0.050(5) 0.063(6) 0.001(4) -0.010(3) -0.014(3) C5 0.052(5) 0.036(5) 0.058(6) -0.008(4) -0.003(4) -0.016(4) C6 0.049(4) 0.033(4) 0.042(4) -0.015(3) -0.006(3) -0.002(3) C7 0.031(3) 0.037(4) 0.037(4) -0.005(3) -0.009(3) -0.007(3) C8 0.029(3) 0.049(4) 0.031(4) -0.007(3) -0.005(3) -0.003(3) C9 0.035(4) 0.040(5) 0.058(5) -0.013(4) -0.003(3) -0.004(3) C10 0.049(5) 0.042(5) 0.043(5) -0.012(4) 0.004(4) -0.004(4) C11 0.075(6) 0.041(5) 0.055(5) -0.013(4) -0.008(4) 0.005(4) C12 0.055(5) 0.051(6) 0.116(9) -0.018(6) 0.008(5) 0.017(5) C13 0.053(5) 0.061(6) 0.079(6) -0.024(5) -0.015(4) 0.001(4) O10 0.064(4) 0.060(4) 0.126(6) -0.050(4) -0.007(4) -0.009(3) C15 0.035(3) 0.045(4) 0.042(4) -0.024(3) 0.003(3) -0.010(3) C16 0.056(5) 0.049(5) 0.037(5) 0.005(4) -0.006(4) -0.002(4) C17 0.050(5) 0.035(5) 0.081(7) -0.007(4) -0.011(4) 0.011(4) C18 0.057(5) 0.047(5) 0.043(4) -0.012(4) 0.002(3) 0.008(4) C19 0.027(3) 0.037(4) 0.048(5) -0.010(4) -0.006(3) 0.010(3) C20 0.025(3) 0.031(4) 0.040(4) -0.011(3) -0.003(3) -0.004(3) C21 0.032(3) 0.043(4) 0.042(4) -0.014(4) -0.014(3) -0.001(3) C22 0.033(3) 0.047(5) 0.032(4) -0.010(4) -0.009(3) 0.003(3) C23 0.069(5) 0.052(5) 0.041(5) 0.006(4) -0.008(4) -0.031(4) C24 0.084(6) 0.053(6) 0.066(7) 0.006(5) -0.019(5) -0.025(5) C25 0.079(6) 0.056(6) 0.043(5) 0.006(4) -0.017(4) 0.006(5) C26 0.052(4) 0.055(5) 0.039(4) -0.012(4) -0.005(3) -0.009(3) C27 0.041(4) 0.046(5) 0.033(4) 0.000(4) -0.007(3) -0.002(4) C28 0.056(5) 0.098(8) 0.049(5) 0.012(5) -0.027(4) 0.020(5) C29 0.023(3) 0.028(3) 0.050(4) 0.004(3) -0.011(3) 0.003(2) C30 0.025(3) 0.035(4) 0.046(5) -0.001(3) -0.008(3) -0.002(3) C31 0.023(3) 0.030(3) 0.043(4) -0.008(3) -0.001(3) 0.000(3) C32 0.049(4) 0.040(5) 0.036(4) -0.009(4) 0.001(3) -0.009(4) C33 0.041(4) 0.052(5) 0.042(5) -0.012(4) -0.012(4) 0.004(4) C34 0.062(5) 0.062(5) 0.042(5) -0.006(4) -0.022(4) 0.027(4) C35 0.109(7) 0.051(6) 0.054(6) 0.003(5) -0.021(5) -0.015(5) C36 0.110(9) 0.060(6) 0.055(6) 0.006(5) -0.017(6) -0.037(6) C37 0.054(5) 0.064(6) 0.057(6) -0.011(5) -0.022(4) -0.005(4) C38 0.056(5) 0.109(8) 0.093(7) -0.025(6) -0.029(5) -0.016(5) C39 0.044(4) 0.048(5) 0.045(4) -0.010(4) 0.005(3) -0.009(4) C40 0.035(4) 0.035(4) 0.085(6) 0.000(4) -0.008(4) 0.014(3) C41 0.052(4) 0.053(5) 0.043(5) 0.018(4) -0.010(3) 0.010(4) C42 0.041(4) 0.051(6) 0.049(5) -0.008(4) -0.008(4) 0.001(4) C43 0.028(3) 0.031(4) 0.031(4) -0.005(3) 0.000(3) -0.003(3) C44 0.028(3) 0.040(4) 0.033(4) 0.011(3) -0.010(2) -0.008(3) C45 0.029(3) 0.043(5) 0.037(4) -0.008(3) -0.001(3) 0.008(3) C46 0.044(4) 0.028(4) 0.042(4) -0.004(3) 0.002(3) 0.013(3) C47 0.024(3) 0.060(6) 0.088(6) -0.025(5) -0.009(3) 0.013(3) C48 0.049(5) 0.065(7) 0.084(7) -0.028(5) -0.015(5) 0.021(5) C49 0.055(5) 0.042(5) 0.066(6) -0.020(4) 0.006(4) 0.006(4) C50 0.057(5) 0.044(5) 0.047(5) -0.004(4) -0.010(4) -0.003(4) C51 0.088(7) 0.049(5) 0.075(6) -0.021(4) -0.026(5) -0.014(5) C52 0.042(4) 0.044(5) 0.043(5) -0.009(4) -0.005(3) 0.006(4) C53 0.036(3) 0.040(4) 0.049(5) -0.012(3) -0.009(3) 0.001(3) C54 0.047(4) 0.049(5) 0.060(6) -0.007(4) -0.007(4) -0.021(4) C55 0.050(5) 0.039(5) 0.053(5) -0.005(4) -0.020(4) -0.010(4) C56 0.029(3) 0.038(4) 0.045(4) 0.003(3) -0.005(3) -0.007(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 Se1 C15 1.921(7) . ? Se1 C1 1.924(7) . ? Se2 C43 1.917(7) . ? Se2 C29 1.940(7) . ? N1 C7 1.331(9) . ? N1 C8 1.414(10) . ? N2 C21 1.362(10) . ? N2 C22 1.422(10) . ? O3 C26 1.360(11) . ? O3 C28 1.379(13) . ? N3 C31 1.350(9) . ? N3 C32 1.429(10) . ? O5 C34 1.397(11) . ? O5 C38 1.448(13) . ? O6 C31 1.193(8) . ? O7 C51 1.374(11) . ? O7 C50 1.388(11) . ? O8 C45 1.228(9) . ? O2 C7 1.223(8) . ? C90 O10 1.492(12) . ? O1 C21 1.257(8) . ? N4 C45 1.385(9) . ? N4 C46 1.434(10) . ? N4 H4A 0.9000 . ? N4 H4B 0.9000 . ? C1 C2 1.409(10) . ? C1 C6 1.410(10) . ? C2 C3 1.397(10) . ? C2 C7 1.535(10) . ? C3 C4 1.322(12) . ? C3 H3 0.9300 . ? C4 C5 1.408(12) . ? C4 H4 0.9300 . ? C5 C6 1.340(11) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C13 1.392(11) . ? C8 C9 1.405(10) . ? C9 C10 1.387(11) . ? C9 H9 0.9300 . ? C10 O10 1.334(11) . ? C10 C11 1.386(13) . ? C11 C12 1.336(15) . ? C11 H11 0.9300 . ? C12 C13 1.384(14) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C15 C16 1.366(11) . ? C15 C20 1.418(10) . ? C16 C17 1.395(13) . ? C16 H16 0.9300 . ? C17 C18 1.352(13) . ? C17 H17 0.9300 . ? C18 C19 1.342(11) . ? C18 H18 0.9300 . ? C19 C20 1.426(9) . ? C19 H19 0.9300 . ? C20 C21 1.489(11) . ? C22 C23 1.389(12) . ? C22 C27 1.429(10) . ? C23 C24 1.366(12) . ? C23 H23 0.9300 . ? C24 C25 1.375(14) . ? C24 H24 0.9300 . ? C25 C26 1.388(15) . ? C25 H25 0.9300 . ? C26 C27 1.359(12) . ? C27 H27 0.9300 . ? C28 H28A 0.9611 . ? C28 H28B 0.9611 . ? C28 H28C 0.9612 . ? C29 C30 1.364(11) . ? C29 C42 1.412(11) . ? C30 C39 1.355(11) . ? C30 C31 1.502(10) . ? C32 C37 1.359(12) . ? C32 C33 1.360(11) . ? C33 C34 1.400(12) . ? C33 H33 0.9300 . ? C34 C35 1.352(16) . ? C35 C36 1.374(15) . ? C35 H35 0.9300 . ? C36 C37 1.409(13) . ? C36 H36 0.9300 . ? C37 H37 0.9300 . ? C38 H38A 0.9608 . ? C38 H38B 0.9608 . ? C38 H38C 0.9609 . ? C39 C40 1.413(12) . ? C39 H39 0.9300 . ? C40 C41 1.383(13) . ? C40 H40 0.9300 . ? C41 C42 1.367(12) . ? C41 H41 0.9300 . ? C42 H42 0.9300 . ? C43 C56 1.370(11) . ? C43 C44 1.411(10) . ? C44 C53 1.400(10) . ? C44 C45 1.467(11) . ? C46 C52 1.344(11) . ? C46 C47 1.413(10) . ? C47 C48 1.362(13) . ? C47 H47 0.9300 . ? C48 C49 1.424(14) . ? C48 H48 0.9300 . ? C49 C50 1.381(12) . ? C49 H49 0.9300 . ? C50 C52 1.395(12) . ? C51 H51A 0.9600 . ? C51 H51B 0.9600 . ? C51 H51C 0.9600 . ? C52 H52 0.9300 . ? C53 C54 1.421(11) . ? C53 H53 0.9300 . ? C54 C55 1.344(12) . ? C54 H54 0.9300 . ? C55 C56 1.420(10) . ? C55 H55 0.9300 . ? C56 H56 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 Se1 C1 101.9(3) . . ? C43 Se2 C29 101.7(3) . . ? C7 N1 C8 127.4(6) . . ? C21 N2 C22 123.8(6) . . ? C26 O3 C28 114.9(7) . . ? C31 N3 C32 127.4(5) . . ? C34 O5 C38 121.6(8) . . ? C51 O7 C50 116.7(8) . . ? C45 N4 C46 127.7(6) . . ? C45 N4 H4A 105.2 . . ? C46 N4 H4A 105.6 . . ? C45 N4 H4B 105.3 . . ? C46 N4 H4B 105.4 . . ? H4A N4 H4B 106.0 . . ? C2 C1 C6 117.3(7) . . ? C2 C1 Se1 122.0(6) . . ? C6 C1 Se1 120.6(6) . . ? C3 C2 C1 118.7(7) . . ? C3 C2 C7 122.0(7) . . ? C1 C2 C7 119.2(7) . . ? C4 C3 C2 122.5(8) . . ? C4 C3 H3 118.7 . . ? C2 C3 H3 118.8 . . ? C3 C4 C5 119.6(7) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C6 C5 C4 119.8(8) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 122.0(8) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 118.8 . . ? O2 C7 N1 124.3(7) . . ? O2 C7 C2 120.0(7) . . ? N1 C7 C2 115.7(6) . . ? C13 C8 N1 117.9(7) . . ? C13 C8 C9 118.3(8) . . ? N1 C8 C9 123.8(7) . . ? C10 C9 C8 119.9(8) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.0 . . ? O10 C10 C9 114.8(8) . . ? O10 C10 C11 125.1(9) . . ? C9 C10 C11 120.0(9) . . ? C12 C11 C10 119.9(9) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 121.7(9) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C12 C13 C8 119.7(9) . . ? C12 C13 H13 120.0 . . ? C8 C13 H13 120.2 . . ? C10 O10 C90 120.3(9) . . ? C16 C15 C20 118.4(7) . . ? C16 C15 Se1 120.2(6) . . ? C20 C15 Se1 120.8(6) . . ? C15 C16 C17 121.8(9) . . ? C15 C16 H16 119.1 . . ? C17 C16 H16 119.1 . . ? C18 C17 C16 118.8(8) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.5 . . ? C19 C18 C17 122.7(8) . . ? C19 C18 H18 118.5 . . ? C17 C18 H18 118.8 . . ? C18 C19 C20 119.5(8) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.0 . . ? C19 C20 C15 118.6(7) . . ? C19 C20 C21 118.8(7) . . ? C15 C20 C21 122.6(7) . . ? O1 C21 N2 125.8(8) . . ? O1 C21 C20 119.0(7) . . ? N2 C21 C20 115.0(6) . . ? C23 C22 N2 117.2(6) . . ? C23 C22 C27 120.4(8) . . ? N2 C22 C27 122.4(7) . . ? C24 C23 C22 116.9(8) . . ? C24 C23 H23 121.7 . . ? C22 C23 H23 121.4 . . ? C23 C24 C25 124.1(10) . . ? C23 C24 H24 118.0 . . ? C25 C24 H24 117.9 . . ? C26 C25 C24 118.6(9) . . ? C26 C25 H25 120.4 . . ? C24 C25 H25 121.0 . . ? C27 C26 O3 126.4(9) . . ? C27 C26 C25 120.2(8) . . ? O3 C26 C25 113.4(9) . . ? C26 C27 C22 119.8(8) . . ? C26 C27 H27 120.1 . . ? C22 C27 H27 120.0 . . ? O3 C28 H28A 109.2 . . ? O3 C28 H28B 109.4 . . ? H28A C28 H28B 109.4 . . ? O3 C28 H28C 110.2 . . ? H28A C28 H28C 109.3 . . ? H28B C28 H28C 109.4 . . ? C30 C29 C42 120.1(7) . . ? C30 C29 Se2 124.3(5) . . ? C42 C29 Se2 114.7(6) . . ? C29 C30 C39 120.3(7) . . ? C29 C30 C31 120.3(7) . . ? C39 C30 C31 119.2(8) . . ? O6 C31 N3 122.6(7) . . ? O6 C31 C30 122.5(7) . . ? N3 C31 C30 114.8(6) . . ? C37 C32 C33 120.4(8) . . ? C37 C32 N3 117.3(7) . . ? C33 C32 N3 122.2(7) . . ? C32 C33 C34 118.2(9) . . ? C32 C33 H33 120.9 . . ? C34 C33 H33 120.9 . . ? C35 C34 O5 118.1(9) . . ? C35 C34 C33 122.4(9) . . ? O5 C34 C33 119.4(10) . . ? C34 C35 C36 119.3(10) . . ? C34 C35 H35 120.7 . . ? C36 C35 H35 120.0 . . ? C35 C36 C37 118.6(10) . . ? C35 C36 H36 120.7 . . ? C37 C36 H36 120.8 . . ? C32 C37 C36 121.1(8) . . ? C32 C37 H37 119.7 . . ? C36 C37 H37 119.3 . . ? O5 C38 H38A 109.1 . . ? O5 C38 H38B 109.4 . . ? H38A C38 H38B 109.4 . . ? O5 C38 H38C 110.2 . . ? H38A C38 H38C 109.3 . . ? H38B C38 H38C 109.4 . . ? C30 C39 C40 121.4(8) . . ? C30 C39 H39 119.6 . . ? C40 C39 H39 119.0 . . ? C41 C40 C39 117.4(7) . . ? C41 C40 H40 121.2 . . ? C39 C40 H40 121.4 . . ? C42 C41 C40 121.9(7) . . ? C42 C41 H41 119.1 . . ? C40 C41 H41 119.0 . . ? C41 C42 C29 118.8(8) . . ? C41 C42 H42 120.6 . . ? C29 C42 H42 120.6 . . ? C56 C43 C44 121.0(7) . . ? C56 C43 Se2 119.1(5) . . ? C44 C43 Se2 119.9(6) . . ? C53 C44 C43 117.3(7) . . ? C53 C44 C45 121.6(7) . . ? C43 C44 C45 121.1(6) . . ? O8 C45 N4 121.1(7) . . ? O8 C45 C44 121.5(7) . . ? N4 C45 C44 117.4(6) . . ? C52 C46 C47 119.7(8) . . ? C52 C46 N4 125.2(7) . . ? C47 C46 N4 115.1(7) . . ? C48 C47 C46 118.8(9) . . ? C48 C47 H47 120.7 . . ? C46 C47 H47 120.5 . . ? C47 C48 C49 122.3(8) . . ? C47 C48 H48 118.8 . . ? C49 C48 H48 118.8 . . ? C50 C49 C48 116.3(8) . . ? C50 C49 H49 121.8 . . ? C48 C49 H49 121.9 . . ? C49 C50 O7 123.7(9) . . ? C49 C50 C52 121.3(9) . . ? O7 C50 C52 115.0(8) . . ? O7 C51 H51A 109.0 . . ? O7 C51 H51B 109.7 . . ? H51A C51 H51B 109.5 . . ? O7 C51 H51C 109.7 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C46 C52 C50 121.3(8) . . ? C46 C52 H52 119.4 . . ? C50 C52 H52 119.3 . . ? C44 C53 C54 121.7(8) . . ? C44 C53 H53 119.2 . . ? C54 C53 H53 119.1 . . ? C55 C54 C53 119.2(8) . . ? C55 C54 H54 120.4 . . ? C53 C54 H54 120.5 . . ? C54 C55 C56 120.6(8) . . ? C54 C55 H55 119.6 . . ? C56 C55 H55 119.8 . . ? C43 C56 C55 120.3(7) . . ? C43 C56 H56 120.1 . . ? C55 C56 H56 119.7 . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 30.97 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.573 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.060 # Attachment 'SeSPOMe.cif' data_dssear42meo2_0m _database_code_depnum_ccdc_archive 'CCDC 869458' #TrackingRef 'SeSPOMe.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H22 N2 O4 Se' _chemical_formula_sum 'C28 H22 N2 O4 Se' _chemical_formula_weight 529.44 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 P12(1)/c1 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 15.0038(7) _cell_length_b 9.2872(4) _cell_length_c 17.4994(7) _cell_angle_alpha 90.00 _cell_angle_beta 105.640(2) _cell_angle_gamma 90.00 _cell_volume 2348.14(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 20.09 _exptl_crystal_description 'needle shape' _exptl_crystal_colour white _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 1.638 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.7629 _exptl_absorpt_correction_T_max 0.9058 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 scan' _diffrn_detector_area_resol_mean 0.3 _diffrn_reflns_number 24595 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 20.87 _reflns_number_total 2472 _reflns_number_gt 1999 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker kappa apex ccd' _computing_cell_refinement 'Bruker kappa apex ccd' _computing_data_reduction 'Bruker saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ortep-III _computing_publication_material WinGX1.80.05 _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^)+(0.0349P)^2^+0.5518P] 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 2472 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0651 _refine_ls_wR_factor_gt 0.0592 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.086 _refine_ls_shift/su_mean 0.003 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 Se1 Se 0.71605(2) 0.11852(3) 0.466334(19) 0.03380(15) Uani 1 1 d . . . O1 O 0.59869(18) 0.2727(3) 0.52339(16) 0.0730(9) Uani 1 1 d . . . O2 O 0.5008(2) -0.0152(4) 0.27765(19) 0.1104(13) Uani 1 1 d . . . O3 O 0.96612(17) 0.3028(3) 0.56599(15) 0.0595(7) Uani 1 1 d . . . O4 O 0.83550(18) 0.1814(3) 0.67154(14) 0.0579(7) Uani 1 1 d . . . N1 N 0.57734(18) 0.1040(3) 0.39362(16) 0.0399(7) Uani 1 1 d . . . N2 N 0.85152(17) 0.1327(3) 0.52457(15) 0.0338(7) Uani 1 1 d . . . C1 C 0.7415(2) 0.0228(3) 0.37640(19) 0.0345(9) Uani 1 1 d . . . C2 C 0.8297(3) -0.0028(4) 0.3690(2) 0.0436(10) Uani 1 1 d . . . H2 H 0.8817 0.0260 0.4084 0.052 Uiso 1 1 calc R . . C3 C 0.8385(3) -0.0721(4) 0.3018(3) 0.0576(11) Uani 1 1 d . . . H3 H 0.8972 -0.0893 0.2954 0.069 Uiso 1 1 calc R . . C4 C 0.7618(3) -0.1160(4) 0.2441(2) 0.0622(12) Uani 1 1 d . . . H4 H 0.7689 -0.1640 0.1994 0.075 Uiso 1 1 calc R . . C5 C 0.6747(3) -0.0895(4) 0.2517(2) 0.0562(11) Uani 1 1 d . . . H5 H 0.6230 -0.1197 0.2125 0.067 Uiso 1 1 calc R . . C6 C 0.6636(3) -0.0171(4) 0.3187(2) 0.0428(9) Uani 1 1 d . . . C7 C 0.5714(3) 0.0235(4) 0.3280(3) 0.0571(11) Uani 1 1 d . . . C8 C 0.4991(2) 0.1418(4) 0.4202(2) 0.0406(9) Uani 1 1 d . . . C9 C 0.5099(3) 0.2292(4) 0.4867(2) 0.0487(10) Uani 1 1 d . . . C10 C 0.6162(3) 0.3654(5) 0.5900(3) 0.0818(14) Uani 1 1 d . . . H10A H 0.5794 0.4510 0.5764 0.123 Uiso 1 1 calc R . . H10B H 0.6806 0.3909 0.6056 0.123 Uiso 1 1 calc R . . H10C H 0.6004 0.3173 0.6331 0.123 Uiso 1 1 calc R . . C11 C 0.4356(3) 0.2698(4) 0.5147(2) 0.0634(12) Uani 1 1 d . . . H11 H 0.4447 0.3275 0.5596 0.076 Uiso 1 1 calc R . . C12 C 0.3474(3) 0.2234(5) 0.4748(3) 0.0717(13) Uani 1 1 d . . . H12 H 0.2968 0.2512 0.4924 0.086 Uiso 1 1 calc R . . C13 C 0.3352(3) 0.1380(5) 0.4105(3) 0.0676(13) Uani 1 1 d . . . H13 H 0.2761 0.1065 0.3842 0.081 Uiso 1 1 calc R . . C14 C 0.4098(3) 0.0966(4) 0.3831(2) 0.0544(11) Uani 1 1 d . . . H14 H 0.3998 0.0372 0.3388 0.065 Uiso 1 1 calc R . . C15 C 0.8893(3) 0.2654(4) 0.5258(2) 0.0386(9) Uani 1 1 d . . . C16 C 0.8248(2) 0.3632(4) 0.46867(19) 0.0368(9) Uani 1 1 d . . . C17 C 0.8482(3) 0.5000(4) 0.4498(2) 0.0488(10) Uani 1 1 d . . . H17 H 0.9072 0.5359 0.4730 0.059 Uiso 1 1 calc R . . C18 C 0.7848(3) 0.5828(4) 0.3969(2) 0.0554(11) Uani 1 1 d . . . H18 H 0.8010 0.6746 0.3842 0.066 Uiso 1 1 calc R . . C19 C 0.6969(3) 0.5311(4) 0.3625(2) 0.0516(10) Uani 1 1 d . . . H19 H 0.6544 0.5888 0.3271 0.062 Uiso 1 1 calc R . . C20 C 0.6711(2) 0.3944(4) 0.37998(19) 0.0400(9) Uani 1 1 d . . . H20 H 0.6121 0.3588 0.3566 0.048 Uiso 1 1 calc R . . C21 C 0.7364(2) 0.3128(3) 0.43353(19) 0.0330(9) Uani 1 1 d . . . C22 C 0.8885(2) 0.0299(4) 0.5859(2) 0.0376(9) Uani 1 1 d . . . C23 C 0.8802(2) 0.0575(4) 0.6620(2) 0.0444(10) Uani 1 1 d . . . C24 C 0.8021(3) 0.1930(5) 0.7402(2) 0.0790(14) Uani 1 1 d . . . H24A H 0.7611 0.1143 0.7413 0.119 Uiso 1 1 calc R . . H24B H 0.7694 0.2823 0.7386 0.119 Uiso 1 1 calc R . . H24C H 0.8534 0.1903 0.7869 0.119 Uiso 1 1 calc R . . C25 C 0.9157(3) -0.0410(5) 0.7228(2) 0.0596(12) Uani 1 1 d . . . H25 H 0.9128 -0.0223 0.7743 0.071 Uiso 1 1 calc R . . C26 C 0.9548(3) -0.1651(5) 0.7057(3) 0.0708(14) Uani 1 1 d . . . H26 H 0.9793 -0.2300 0.7463 0.085 Uiso 1 1 calc R . . C27 C 0.9590(3) -0.1972(5) 0.6296(3) 0.0697(13) Uani 1 1 d . . . H27 H 0.9834 -0.2844 0.6186 0.084 Uiso 1 1 calc R . . C28 C 0.9262(2) -0.0972(4) 0.5702(2) 0.0493(10) Uani 1 1 d . . . H28 H 0.9297 -0.1165 0.5190 0.059 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 Se1 0.0291(2) 0.0375(2) 0.0315(2) 0.00186(18) 0.00247(16) -0.00522(18) O1 0.0437(19) 0.100(2) 0.076(2) -0.0454(18) 0.0171(15) -0.0116(16) O2 0.047(2) 0.162(3) 0.097(3) -0.075(3) -0.0226(19) 0.006(2) O3 0.0360(17) 0.0668(18) 0.0635(18) 0.0104(14) -0.0076(15) -0.0209(14) O4 0.073(2) 0.0606(19) 0.0420(17) 0.0008(13) 0.0199(15) -0.0006(16) N1 0.0305(19) 0.0465(19) 0.0350(18) -0.0053(16) -0.0046(15) -0.0021(15) N2 0.0274(17) 0.0387(18) 0.0307(17) 0.0053(15) 0.0001(13) -0.0057(15) C1 0.037(2) 0.028(2) 0.036(2) 0.0024(17) 0.005(2) -0.0036(18) C2 0.048(3) 0.042(2) 0.039(2) -0.0005(19) 0.009(2) -0.0037(19) C3 0.059(3) 0.056(3) 0.062(3) -0.007(2) 0.023(3) 0.002(2) C4 0.084(4) 0.058(3) 0.048(3) -0.007(2) 0.023(3) 0.009(3) C5 0.064(3) 0.053(3) 0.041(3) -0.008(2) -0.005(2) 0.001(2) C6 0.044(3) 0.038(2) 0.040(2) -0.0031(19) 0.001(2) -0.0001(19) C7 0.041(3) 0.060(3) 0.058(3) -0.012(2) -0.009(2) 0.000(2) C8 0.030(3) 0.041(2) 0.045(2) 0.008(2) 0.001(2) -0.0021(19) C9 0.033(3) 0.053(3) 0.060(3) 0.005(2) 0.012(2) -0.001(2) C10 0.070(3) 0.094(4) 0.076(3) -0.039(3) 0.011(3) -0.004(3) C11 0.051(3) 0.064(3) 0.080(3) 0.000(2) 0.027(3) 0.000(2) C12 0.050(4) 0.080(4) 0.095(4) 0.024(3) 0.036(3) 0.006(3) C13 0.038(3) 0.084(3) 0.081(4) 0.032(3) 0.015(3) -0.009(3) C14 0.042(3) 0.059(3) 0.058(3) 0.018(2) 0.005(2) -0.013(2) C15 0.033(2) 0.048(3) 0.035(2) 0.0034(19) 0.008(2) -0.008(2) C16 0.042(2) 0.036(2) 0.032(2) -0.0019(18) 0.0086(19) -0.008(2) C17 0.050(3) 0.045(3) 0.049(3) 0.000(2) 0.009(2) -0.013(2) C18 0.078(3) 0.033(2) 0.054(3) 0.006(2) 0.016(3) -0.009(2) C19 0.063(3) 0.041(3) 0.046(3) 0.007(2) 0.006(2) 0.013(2) C20 0.041(2) 0.043(2) 0.034(2) -0.0019(19) 0.0055(19) 0.002(2) C21 0.041(2) 0.033(2) 0.024(2) 0.0004(17) 0.0086(18) -0.0010(19) C22 0.020(2) 0.046(3) 0.042(3) 0.007(2) -0.0007(18) -0.0063(19) C23 0.030(2) 0.054(3) 0.043(3) 0.008(2) 0.000(2) -0.011(2) C24 0.084(3) 0.102(4) 0.055(3) -0.013(3) 0.025(3) -0.005(3) C25 0.043(3) 0.080(3) 0.048(3) 0.020(3) -0.002(2) -0.014(3) C26 0.046(3) 0.076(4) 0.082(4) 0.046(3) 0.003(3) -0.001(3) C27 0.047(3) 0.061(3) 0.094(4) 0.019(3) 0.006(3) 0.012(2) C28 0.040(2) 0.051(3) 0.053(3) 0.012(2) 0.005(2) 0.010(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 Se1 C1 1.933(3) . ? Se1 C21 1.942(3) . ? Se1 N2 2.018(2) . ? Se1 N1 2.131(3) . ? O1 C9 1.375(4) . ? O1 C10 1.415(4) . ? O2 C7 1.234(4) . ? O3 C15 1.227(4) . ? O4 C23 1.365(4) . ? O4 C24 1.425(4) . ? N1 C7 1.353(4) . ? N1 C8 1.419(4) . ? N2 C15 1.355(4) . ? N2 C22 1.432(4) . ? C1 C6 1.374(4) . ? C1 C2 1.384(4) . ? C2 C3 1.378(5) . ? C2 H2 0.9300 . ? C3 C4 1.373(5) . ? C3 H3 0.9300 . ? C4 C5 1.371(5) . ? C4 H4 0.9300 . ? C5 C6 1.399(5) . ? C5 H5 0.9300 . ? C6 C7 1.485(5) . ? C8 C14 1.387(5) . ? C8 C9 1.392(5) . ? C9 C11 1.384(5) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.388(5) . ? C11 H11 0.9300 . ? C12 C13 1.349(6) . ? C12 H12 0.9300 . ? C13 C14 1.385(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.497(5) . ? C16 C17 1.381(4) . ? C16 C21 1.385(4) . ? C17 C18 1.371(5) . ? C17 H17 0.9300 . ? C18 C19 1.380(5) . ? C18 H18 0.9300 . ? C19 C20 1.384(5) . ? C19 H19 0.9300 . ? C20 C21 1.384(4) . ? C20 H20 0.9300 . ? C22 C28 1.368(5) . ? C22 C23 1.394(5) . ? C23 C25 1.396(5) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.362(6) . ? C25 H25 0.9300 . ? C26 C27 1.383(6) . ? C26 H26 0.9300 . ? C27 C28 1.381(5) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Se1 C21 96.06(13) . . ? C1 Se1 N2 92.74(13) . . ? C21 Se1 N2 82.63(13) . . ? C1 Se1 N1 81.98(13) . . ? C21 Se1 N1 95.07(13) . . ? N2 Se1 N1 174.01(10) . . ? C9 O1 C10 120.3(3) . . ? C23 O4 C24 117.6(3) . . ? C7 N1 C8 123.0(3) . . ? C7 N1 Se1 111.9(2) . . ? C8 N1 Se1 123.3(2) . . ? C15 N2 C22 121.2(3) . . ? C15 N2 Se1 115.3(2) . . ? C22 N2 Se1 118.0(2) . . ? C6 C1 C2 122.0(3) . . ? C6 C1 Se1 114.0(3) . . ? C2 C1 Se1 124.0(3) . . ? C3 C2 C1 118.3(3) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C4 C3 C2 120.8(4) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 120.0(4) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 118.4(3) . . ? C1 C6 C7 119.0(3) . . ? C5 C6 C7 122.6(4) . . ? O2 C7 N1 127.9(4) . . ? O2 C7 C6 119.5(4) . . ? N1 C7 C6 112.5(3) . . ? C14 C8 C9 116.6(3) . . ? C14 C8 N1 123.5(4) . . ? C9 C8 N1 120.0(3) . . ? O1 C9 C11 121.8(4) . . ? O1 C9 C8 116.1(3) . . ? C11 C9 C8 122.1(4) . . ? O1 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 C12 119.2(4) . . ? C9 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C13 C12 C11 119.9(4) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.8(4) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C8 121.5(4) . . ? C13 C14 H14 119.2 . . ? C8 C14 H14 119.2 . . ? O3 C15 N2 126.2(3) . . ? O3 C15 C16 123.3(3) . . ? N2 C15 C16 110.4(3) . . ? C17 C16 C21 118.7(3) . . ? C17 C16 C15 123.9(3) . . ? C21 C16 C15 117.5(3) . . ? C18 C17 C16 120.1(4) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 120.5(3) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C20 120.9(3) . . ? C18 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C19 C20 C21 117.6(3) . . ? C19 C20 H20 121.2 . . ? C21 C20 H20 121.2 . . ? C16 C21 C20 122.2(3) . . ? C16 C21 Se1 113.0(2) . . ? C20 C21 Se1 124.8(3) . . ? C28 C22 C23 119.9(3) . . ? C28 C22 N2 121.5(3) . . ? C23 C22 N2 118.5(3) . . ? O4 C23 C22 116.5(3) . . ? O4 C23 C25 123.9(4) . . ? C22 C23 C25 119.6(4) . . ? O4 C24 H24A 109.5 . . ? O4 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O4 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C23 119.0(4) . . ? C26 C25 H25 120.5 . . ? C23 C25 H25 120.5 . . ? C25 C26 C27 121.9(4) . . ? C25 C26 H26 119.0 . . ? C27 C26 H26 119.0 . . ? C26 C27 C28 118.6(4) . . ? C26 C27 H27 120.7 . . ? C28 C27 H27 120.7 . . ? C22 C28 C27 120.8(4) . . ? C22 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 20.87 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.194 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.041 _atom_sites_special_details ; The structure was solved using Patterson Methods, followed by a Tangent Expansion (ShelXS). RE = 0.1, Nqual = -1, Ralpha = 0.066 ;