Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Carl Schiesser' _publ_contact_author_address ; School of Chemistry The University of Melbourne 30 Flemington Road The University of Melbourne Victoria 3010 AUSTRALIA ; _publ_contact_author_email DIRECTOR@FREERADICAL.ORG.AU _publ_section_title ; On the Stability of 2-Aminoselenophene-3-carboxylates: Potential Dual-Acting Selenium - Containing Allosteric Enhancers of A1 Adenosine Receptor Binding ; loop_ _publ_author_name 'Carl Schiesser' 'Kylee M. Aumann' 'Peter J. Scammells' 'Jonathan M. White' data_jmwka1lt _database_code_depnum_ccdc_archive 'CCDC 633017' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 N O3 Se' _chemical_formula_weight 376.30 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 ' 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 8.0161(9) _cell_length_b 10.6336(13) _cell_length_c 18.746(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.498(2) _cell_angle_gamma 90.00 _cell_volume 1594.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 4731 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.53 _exptl_crystal_description hexagonal _exptl_crystal_colour yellow _exptl_crystal_size_min 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_max 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 2.369 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(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 9581 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.56 _reflns_number_total 3629 _reflns_number_gt 3177 _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^)+(0.0539P)^2^+0.0984P] 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 3629 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0831 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 C6' C 0.0294(12) 1.1267(7) 0.2264(4) 0.036(2) Uani 0.368(10) 1 d P A 1 H6'1 H 0.1282 1.1757 0.2403 0.044 Uiso 0.368(10) 1 calc PR A 1 H6'2 H -0.0424 1.1260 0.2662 0.044 Uiso 0.368(10) 1 calc PR A 1 C5' C -0.0611(12) 1.1863(8) 0.1629(4) 0.0310(17) Uani 0.368(10) 1 d P A 1 H5'1 H -0.1044 1.2674 0.1765 0.037 Uiso 0.368(10) 1 calc PR A 1 H5'2 H -0.1551 1.1338 0.1469 0.037 Uiso 0.368(10) 1 calc PR A 1 C6 C -0.0576(7) 1.1014(4) 0.2078(2) 0.0315(11) Uani 0.632(10) 1 d P A 2 H6A H -0.1557 1.0724 0.1797 0.038 Uiso 0.632(10) 1 calc PR A 2 H6B H -0.0900 1.1176 0.2560 0.038 Uiso 0.632(10) 1 calc PR A 2 C5 C 0.0061(7) 1.2222(4) 0.1757(2) 0.0321(10) Uani 0.632(10) 1 d P A 2 H5A H -0.0807 1.2858 0.1761 0.038 Uiso 0.632(10) 1 calc PR A 2 H5B H 0.1016 1.2524 0.2051 0.038 Uiso 0.632(10) 1 calc PR A 2 C1 C 0.2847(2) 0.92572(16) 0.02340(9) 0.0238(3) Uani 1 1 d . A . C2 C 0.2201(2) 1.04566(16) 0.02216(9) 0.0233(3) Uani 1 1 d . . . C3 C 0.1423(2) 1.08075(16) 0.08741(9) 0.0239(3) Uani 1 1 d . A . C8 C 0.1487(2) 0.98986(17) 0.13750(9) 0.0281(4) Uani 1 1 d . A . C7 C 0.0780(3) 0.9982(2) 0.20979(11) 0.0361(5) Uani 1 1 d . . . C4 C 0.0565(2) 1.20433(19) 0.10011(10) 0.0291(4) Uani 1 1 d . . . C9 C 0.2366(2) 1.12363(17) -0.04147(9) 0.0244(3) Uani 1 1 d . . . C10 C 0.1935(3) 1.32145(18) -0.09654(10) 0.0347(4) Uani 1 1 d . . . H10A H 0.1371 1.2846 -0.1388 0.042 Uiso 1 1 calc R . . H10B H 0.3102 1.3339 -0.1056 0.042 Uiso 1 1 calc R . . C11 C 0.1139(3) 1.44393(19) -0.07893(12) 0.0446(5) Uani 1 1 d . . . H11A H -0.0012 1.4301 -0.0699 0.067 Uiso 1 1 calc R . . H11B H 0.1207 1.5008 -0.1184 0.067 Uiso 1 1 calc R . . H11C H 0.1712 1.4795 -0.0372 0.067 Uiso 1 1 calc R . . C12 C 0.4163(2) 0.74983(17) -0.03320(10) 0.0283(4) Uani 1 1 d . . . C13 C 0.4834(2) 0.70568(18) -0.10132(9) 0.0272(4) Uani 1 1 d . . . C14 C 0.5371(2) 0.58163(18) -0.10363(10) 0.0326(4) Uani 1 1 d . . . H14 H 0.5337 0.5311 -0.0633 0.039 Uiso 1 1 calc R . . C15 C 0.5958(3) 0.53295(19) -0.16611(11) 0.0380(5) Uani 1 1 d . . . H15 H 0.6335 0.4503 -0.1671 0.046 Uiso 1 1 calc R . . C16 C 0.5985(3) 0.6060(2) -0.22631(11) 0.0367(4) Uani 1 1 d . . . H16 H 0.6352 0.5723 -0.2684 0.044 Uiso 1 1 calc R . . C17 C 0.5466(2) 0.7296(2) -0.22428(10) 0.0349(4) Uani 1 1 d . . . H17 H 0.5490 0.7792 -0.2651 0.042 Uiso 1 1 calc R . . C18 C 0.4910(2) 0.78024(19) -0.16191(10) 0.0317(4) Uani 1 1 d . . . H18 H 0.4587 0.8642 -0.1606 0.038 Uiso 1 1 calc R . . N1 N 0.3641(2) 0.87124(15) -0.03191(8) 0.0257(3) Uani 1 1 d . . . O1 O 0.40489(19) 0.68107(13) 0.01876(7) 0.0366(3) Uani 1 1 d . . . O2 O 0.29961(17) 1.08795(12) -0.09574(6) 0.0297(3) Uani 1 1 d . . . O3 O 0.17842(17) 1.23995(12) -0.03530(6) 0.0301(3) Uani 1 1 d . . . Se Se 0.25570(2) 0.843264(17) 0.108982(9) 0.02972(9) Uani 1 1 d . . . H1 H 0.369(3) 0.921(2) -0.0668(12) 0.033(6) Uiso 1 1 d . . . H4B H 0.131(3) 1.279(2) 0.0928(12) 0.040(6) Uiso 1 1 d . . . H4A H -0.035(3) 1.220(2) 0.0617(12) 0.035(6) Uiso 1 1 d . . . H7B H 0.010(3) 0.926(3) 0.2148(15) 0.062(8) Uiso 1 1 d . . . H7A H 0.157(4) 0.996(2) 0.2411(15) 0.065(9) 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 C6' 0.040(5) 0.044(3) 0.025(3) -0.005(2) 0.008(3) -0.008(3) C5' 0.030(4) 0.035(4) 0.028(3) -0.007(3) 0.003(3) 0.000(3) C6 0.032(2) 0.0392(19) 0.0239(16) -0.0067(14) 0.0083(15) -0.0067(16) C5 0.035(2) 0.030(2) 0.0316(19) -0.0049(15) 0.0105(16) -0.0047(17) C1 0.0260(8) 0.0258(8) 0.0197(8) -0.0006(7) 0.0006(6) -0.0029(7) C2 0.0257(8) 0.0247(8) 0.0194(8) -0.0010(6) 0.0018(6) -0.0032(7) C3 0.0253(8) 0.0262(8) 0.0204(8) -0.0030(7) 0.0014(6) -0.0026(7) C8 0.0320(9) 0.0319(10) 0.0205(8) -0.0017(7) 0.0037(7) 0.0008(7) C7 0.0435(12) 0.0445(12) 0.0210(9) 0.0025(8) 0.0070(8) 0.0019(10) C4 0.0332(10) 0.0287(10) 0.0258(9) -0.0026(8) 0.0047(8) 0.0024(8) C9 0.0275(9) 0.0232(8) 0.0227(8) -0.0010(7) 0.0018(7) -0.0016(7) C10 0.0528(12) 0.0264(9) 0.0262(9) 0.0071(7) 0.0125(9) 0.0041(9) C11 0.0720(16) 0.0282(10) 0.0349(11) 0.0057(9) 0.0129(10) 0.0113(10) C12 0.0318(9) 0.0274(9) 0.0255(9) -0.0005(7) 0.0012(7) 0.0011(7) C13 0.0286(9) 0.0270(9) 0.0260(9) -0.0015(7) 0.0009(7) 0.0021(7) C14 0.0400(11) 0.0263(9) 0.0318(10) -0.0014(8) 0.0047(8) 0.0007(8) C15 0.0476(12) 0.0276(9) 0.0394(11) -0.0082(8) 0.0083(9) 0.0007(9) C16 0.0390(11) 0.0415(11) 0.0303(10) -0.0125(9) 0.0069(8) -0.0004(9) C17 0.0360(11) 0.0432(11) 0.0258(9) 0.0017(8) 0.0039(8) 0.0042(9) C18 0.0354(10) 0.0307(10) 0.0293(9) 0.0028(8) 0.0041(8) 0.0082(8) N1 0.0319(8) 0.0234(7) 0.0221(7) 0.0010(6) 0.0039(6) 0.0019(6) O1 0.0538(9) 0.0287(7) 0.0284(7) 0.0057(5) 0.0105(6) 0.0086(6) O2 0.0424(7) 0.0258(7) 0.0218(6) 0.0001(5) 0.0086(5) 0.0010(6) O3 0.0453(8) 0.0226(6) 0.0235(6) 0.0027(5) 0.0106(5) 0.0029(5) Se 0.03811(14) 0.02865(13) 0.02280(12) 0.00536(7) 0.00513(8) 0.00365(7) _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 C6' C7 1.461(7) . ? C6' C5' 1.496(12) . ? C6' H6'1 0.9700 . ? C6' H6'2 0.9700 . ? C5' C4 1.564(7) . ? C5' H5'1 0.9700 . ? C5' H5'2 0.9700 . ? C6 C5 1.521(7) . ? C6 C7 1.544(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C5 C4 1.509(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C1 C2 1.376(2) . ? C1 N1 1.377(2) . ? C1 Se 1.8554(17) . ? C2 C3 1.455(2) . ? C2 C9 1.465(2) . ? C3 C8 1.346(2) . ? C3 C4 1.509(3) . ? C8 C7 1.503(2) . ? C8 Se 1.8728(18) . ? C7 H7B 0.95(3) . ? C7 H7A 0.83(3) . ? C4 H4B 1.01(2) . ? C4 H4A 1.01(2) . ? C9 O2 1.223(2) . ? C9 O3 1.329(2) . ? C10 O3 1.449(2) . ? C10 C11 1.496(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 O1 1.226(2) . ? C12 N1 1.358(2) . ? C12 C13 1.492(2) . ? C13 C14 1.389(3) . ? C13 C18 1.389(3) . ? C14 C15 1.389(3) . ? C14 H14 0.9300 . ? C15 C16 1.371(3) . ? C15 H15 0.9300 . ? C16 C17 1.380(3) . ? C16 H16 0.9300 . ? C17 C18 1.386(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? N1 H1 0.84(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 C7 C6' C5' 110.5(7) . . ? C7 C6' H6'1 109.6 . . ? C5' C6' H6'1 109.6 . . ? C7 C6' H6'2 109.6 . . ? C5' C6' H6'2 109.6 . . ? H6'1 C6' H6'2 108.1 . . ? C6' C5' C4 111.4(7) . . ? C6' C5' H5'1 109.3 . . ? C4 C5' H5'1 109.3 . . ? C6' C5' H5'2 109.3 . . ? C4 C5' H5'2 109.3 . . ? H5'1 C5' H5'2 108.0 . . ? C5 C6 C7 110.9(4) . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C7 C6 H6B 109.5 . . ? H6A C6 H6B 108.0 . . ? C4 C5 C6 112.4(4) . . ? C4 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? C4 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C2 C1 N1 124.61(15) . . ? C2 C1 Se 112.68(12) . . ? N1 C1 Se 122.71(13) . . ? C1 C2 C3 113.80(15) . . ? C1 C2 C9 119.04(15) . . ? C3 C2 C9 127.15(15) . . ? C8 C3 C2 113.73(16) . . ? C8 C3 C4 120.89(16) . . ? C2 C3 C4 125.36(15) . . ? C3 C8 C7 125.90(17) . . ? C3 C8 Se 113.39(13) . . ? C7 C8 Se 120.70(14) . . ? C6' C7 C8 111.5(3) . . ? C6' C7 C6 31.0(3) . . ? C8 C7 C6 108.92(19) . . ? C6' C7 H7B 125.0(17) . . ? C8 C7 H7B 106.9(16) . . ? C6 C7 H7B 99.8(17) . . ? C6' C7 H7A 94.1(19) . . ? C8 C7 H7A 108.8(19) . . ? C6 C7 H7A 122.2(19) . . ? H7B C7 H7A 109(2) . . ? C3 C4 C5 114.1(2) . . ? C3 C4 C5' 108.3(3) . . ? C5 C4 C5' 25.9(2) . . ? C3 C4 H4B 112.6(13) . . ? C5 C4 H4B 102.9(13) . . ? C5' C4 H4B 126.1(13) . . ? C3 C4 H4A 110.4(13) . . ? C5 C4 H4A 115.3(12) . . ? C5' C4 H4A 96.6(13) . . ? H4B C4 H4A 100.4(18) . . ? O2 C9 O3 121.72(16) . . ? O2 C9 C2 124.32(16) . . ? O3 C9 C2 113.95(14) . . ? O3 C10 C11 106.77(15) . . ? O3 C10 H10A 110.4 . . ? C11 C10 H10A 110.4 . . ? O3 C10 H10B 110.4 . . ? C11 C10 H10B 110.4 . . ? H10A C10 H10B 108.6 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O1 C12 N1 121.00(17) . . ? O1 C12 C13 122.74(17) . . ? N1 C12 C13 116.24(16) . . ? C14 C13 C18 119.18(17) . . ? C14 C13 C12 117.01(16) . . ? C18 C13 C12 123.79(17) . . ? C15 C14 C13 120.11(18) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 120.42(19) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 119.78(17) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C16 C17 C18 120.46(18) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C13 120.00(19) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? C12 N1 C1 124.78(16) . . ? C12 N1 H1 123.5(15) . . ? C1 N1 H1 111.5(14) . . ? C9 O3 C10 116.15(14) . . ? C1 Se C8 86.40(8) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.809 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.074 # Attachment 'B700812K-9-NO2.cif' data_jmwka2 _database_code_depnum_ccdc_archive 'CCDC 633018' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 N2 O5 Se' _chemical_formula_weight 421.30 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6394(10) _cell_length_b 10.0481(11) _cell_length_c 10.1555(11) _cell_angle_alpha 93.933(2) _cell_angle_beta 101.874(2) _cell_angle_gamma 117.258(2) _cell_volume 840.57(16) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2905 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.43 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_min 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_max 0.2 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.665 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 2.267 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 1.00 _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 5132 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0372 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3646 _reflns_number_gt 3311 _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^)+(0.0475P)^2^+0.4717P] 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 3646 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0897 _refine_ls_wR_factor_gt 0.0865 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _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 0.8788(3) 0.7024(3) 0.4693(2) 0.0220(4) Uani 1 1 d . . . C2 C 0.9623(3) 0.8177(3) 0.4047(2) 0.0208(4) Uani 1 1 d . . . C3 C 0.8583(3) 0.8585(3) 0.3111(2) 0.0219(4) Uani 1 1 d . . . C8 C 0.7001(3) 0.7750(3) 0.3050(2) 0.0235(5) Uani 1 1 d . . . C7 C 0.5643(3) 0.7913(3) 0.2187(3) 0.0270(5) Uani 1 1 d . . . H7A H 0.5307 0.8462 0.2757 0.032 Uiso 1 1 calc R . . H7B H 0.4723 0.6911 0.1792 0.032 Uiso 1 1 calc R . . C6 C 0.6172(4) 0.8758(4) 0.1059(3) 0.0389(6) Uani 1 1 d . . . H6A H 0.6223 0.8090 0.0356 0.047 Uiso 1 1 calc R . . H6B H 0.5381 0.9056 0.0645 0.047 Uiso 1 1 calc R . . C5 C 0.7792(3) 1.0143(3) 0.1597(3) 0.0394(7) Uani 1 1 d . . . H5A H 0.7715 1.0825 0.2266 0.047 Uiso 1 1 calc R . . H5B H 0.8083 1.0667 0.0849 0.047 Uiso 1 1 calc R . . C4 C 0.9136(3) 0.9804(3) 0.2262(2) 0.0256(5) Uani 1 1 d . . . H4B H 0.9514 0.9481 0.1553 0.031 Uiso 1 1 calc R . . H4A H 1.0040 1.0729 0.2840 0.031 Uiso 1 1 calc R . . C9 C 1.1375(3) 0.8835(3) 0.4324(2) 0.0230(5) Uani 1 1 d . . . C10 C 1.3765(3) 1.0559(3) 0.3797(3) 0.0283(5) Uani 1 1 d . . . H10A H 1.4085 0.9775 0.3753 0.034 Uiso 1 1 calc R . . H10B H 1.4324 1.1222 0.4689 0.034 Uiso 1 1 calc R . . C11 C 1.4174(4) 1.1454(5) 0.2688(4) 0.0528(9) Uani 1 1 d . . . H11A H 1.3602 1.0788 0.1812 0.079 Uiso 1 1 calc R . . H11B H 1.5319 1.1916 0.2788 0.079 Uiso 1 1 calc R . . H11C H 1.3864 1.2233 0.2751 0.079 Uiso 1 1 calc R . . C12 C 0.8697(3) 0.5329(3) 0.6301(2) 0.0246(5) Uani 1 1 d . . . C13 C 0.9701(3) 0.4915(3) 0.7344(2) 0.0225(4) Uani 1 1 d . . . C14 C 0.8853(3) 0.3755(3) 0.7998(3) 0.0262(5) Uani 1 1 d . . . H14 H 0.7728 0.3274 0.7762 0.031 Uiso 1 1 calc R . . C15 C 0.9670(3) 0.3311(3) 0.8994(3) 0.0282(5) Uani 1 1 d . . . H15 H 0.9108 0.2534 0.9436 0.034 Uiso 1 1 calc R . . C16 C 1.1329(3) 0.4039(3) 0.9321(2) 0.0244(5) Uani 1 1 d . . . C17 C 1.2212(3) 0.5168(3) 0.8677(3) 0.0262(5) Uani 1 1 d . . . H17 H 1.3336 0.5622 0.8902 0.031 Uiso 1 1 calc R . . C18 C 1.1376(3) 0.5610(3) 0.7682(3) 0.0263(5) Uani 1 1 d . . . H18 H 1.1946 0.6380 0.7237 0.032 Uiso 1 1 calc R . . N1 N 0.9509(3) 0.6440(2) 0.5636(2) 0.0234(4) Uani 1 1 d . . . N2 N 1.2193(3) 0.3583(3) 1.0408(2) 0.0305(5) Uani 1 1 d . . . O2 O 1.2195(2) 0.8467(2) 0.51495(18) 0.0287(4) Uani 1 1 d . . . O3 O 1.2029(2) 0.98768(19) 0.35818(17) 0.0260(4) Uani 1 1 d . . . O1 O 0.7230(2) 0.4697(2) 0.6067(2) 0.0365(4) Uani 1 1 d . . . O4 O 1.1389(3) 0.2569(3) 1.0956(2) 0.0505(6) Uani 1 1 d . . . O5 O 1.3665(2) 0.4235(2) 1.0706(2) 0.0407(5) Uani 1 1 d . . . Se1 Se 0.65726(3) 0.62951(3) 0.41824(2) 0.02477(10) Uani 1 1 d . . . H1 H 1.049(4) 0.688(4) 0.576(3) 0.037(9) 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 0.0173(10) 0.0241(11) 0.0240(11) 0.0069(9) 0.0032(9) 0.0101(9) C2 0.0181(11) 0.0221(11) 0.0206(10) 0.0045(8) 0.0038(8) 0.0088(9) C3 0.0220(11) 0.0215(11) 0.0216(10) 0.0046(9) 0.0042(9) 0.0105(9) C8 0.0234(12) 0.0219(11) 0.0240(11) 0.0073(9) 0.0054(9) 0.0100(9) C7 0.0211(11) 0.0282(12) 0.0318(12) 0.0081(10) 0.0052(10) 0.0125(10) C6 0.0322(15) 0.0479(17) 0.0394(15) 0.0174(13) 0.0067(12) 0.0216(13) C5 0.0307(14) 0.0402(15) 0.0453(16) 0.0239(13) 0.0060(12) 0.0150(13) C4 0.0219(11) 0.0256(12) 0.0256(11) 0.0086(9) 0.0033(9) 0.0092(10) C9 0.0217(11) 0.0230(11) 0.0233(11) 0.0065(9) 0.0070(9) 0.0092(9) C10 0.0161(11) 0.0340(13) 0.0338(13) 0.0133(11) 0.0072(9) 0.0101(10) C11 0.0267(15) 0.076(2) 0.0563(19) 0.0445(18) 0.0176(14) 0.0179(16) C12 0.0215(12) 0.0252(11) 0.0285(12) 0.0098(9) 0.0067(9) 0.0116(10) C13 0.0202(11) 0.0222(11) 0.0253(11) 0.0066(9) 0.0058(9) 0.0103(9) C14 0.0189(11) 0.0267(12) 0.0321(12) 0.0107(10) 0.0082(9) 0.0090(10) C15 0.0245(12) 0.0257(12) 0.0337(13) 0.0139(10) 0.0104(10) 0.0094(10) C16 0.0268(12) 0.0236(11) 0.0242(11) 0.0064(9) 0.0049(9) 0.0137(10) C17 0.0198(11) 0.0250(12) 0.0296(12) 0.0073(10) 0.0043(9) 0.0078(10) C18 0.0203(11) 0.0256(12) 0.0322(12) 0.0142(10) 0.0088(10) 0.0085(10) N1 0.0167(10) 0.0248(10) 0.0276(10) 0.0106(8) 0.0052(8) 0.0086(8) N2 0.0287(11) 0.0300(11) 0.0316(11) 0.0103(9) 0.0042(9) 0.0144(10) O2 0.0184(8) 0.0342(9) 0.0309(9) 0.0142(7) 0.0042(7) 0.0106(7) O3 0.0165(8) 0.0280(9) 0.0313(9) 0.0133(7) 0.0060(7) 0.0082(7) O1 0.0193(9) 0.0397(11) 0.0503(12) 0.0258(9) 0.0085(8) 0.0120(8) O4 0.0374(12) 0.0542(13) 0.0575(14) 0.0387(12) 0.0097(10) 0.0177(10) O5 0.0264(10) 0.0398(11) 0.0473(12) 0.0149(9) -0.0015(8) 0.0127(9) Se1 0.01717(13) 0.02524(14) 0.03203(15) 0.01191(10) 0.00724(9) 0.00923(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 C2 1.374(3) . ? C1 N1 1.386(3) . ? C1 Se1 1.851(2) . ? C2 C3 1.454(3) . ? C2 C9 1.458(3) . ? C3 C8 1.347(3) . ? C3 C4 1.505(3) . ? C8 C7 1.501(3) . ? C8 Se1 1.872(2) . ? C7 C6 1.507(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C6 C5 1.493(4) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C5 C4 1.526(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C4 H4B 0.9700 . ? C4 H4A 0.9700 . ? C9 O2 1.226(3) . ? C9 O3 1.327(3) . ? C10 O3 1.447(3) . ? C10 C11 1.493(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 O1 1.216(3) . ? C12 N1 1.355(3) . ? C12 C13 1.496(3) . ? C13 C18 1.385(3) . ? C13 C14 1.387(3) . ? C14 C15 1.378(3) . ? C14 H14 0.9300 . ? C15 C16 1.371(3) . ? C15 H15 0.9300 . ? C16 C17 1.373(3) . ? C16 N2 1.471(3) . ? C17 C18 1.387(3) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? N1 H1 0.81(4) . ? N2 O5 1.216(3) . ? N2 O4 1.217(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 C2 C1 N1 124.1(2) . . ? C2 C1 Se1 113.62(16) . . ? N1 C1 Se1 122.24(17) . . ? C1 C2 C3 113.2(2) . . ? C1 C2 C9 119.6(2) . . ? C3 C2 C9 127.1(2) . . ? C8 C3 C2 113.5(2) . . ? C8 C3 C4 120.7(2) . . ? C2 C3 C4 125.8(2) . . ? C3 C8 C7 125.9(2) . . ? C3 C8 Se1 113.87(17) . . ? C7 C8 Se1 120.28(18) . . ? C8 C7 C6 110.5(2) . . ? C8 C7 H7A 109.5 . . ? C6 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C5 C6 C7 111.0(2) . . ? C5 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? C5 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C6 C5 C4 113.9(2) . . ? C6 C5 H5A 108.8 . . ? C4 C5 H5A 108.8 . . ? C6 C5 H5B 108.8 . . ? C4 C5 H5B 108.8 . . ? H5A C5 H5B 107.7 . . ? C3 C4 C5 112.4(2) . . ? C3 C4 H4B 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4A 109.1 . . ? H4B C4 H4A 107.9 . . ? O2 C9 O3 121.9(2) . . ? O2 C9 C2 124.2(2) . . ? O3 C9 C2 113.91(19) . . ? O3 C10 C11 106.9(2) . . ? O3 C10 H10A 110.4 . . ? C11 C10 H10A 110.4 . . ? O3 C10 H10B 110.4 . . ? C11 C10 H10B 110.4 . . ? H10A C10 H10B 108.6 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O1 C12 N1 122.0(2) . . ? O1 C12 C13 121.5(2) . . ? N1 C12 C13 116.5(2) . . ? C18 C13 C14 119.6(2) . . ? C18 C13 C12 124.5(2) . . ? C14 C13 C12 115.9(2) . . ? C15 C14 C13 120.4(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 118.6(2) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C15 C16 C17 122.9(2) . . ? C15 C16 N2 118.2(2) . . ? C17 C16 N2 118.8(2) . . ? C16 C17 C18 117.9(2) . . ? C16 C17 H17 121.0 . . ? C18 C17 H17 121.0 . . ? C13 C18 C17 120.6(2) . . ? C13 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C12 N1 C1 124.4(2) . . ? C12 N1 H1 125(2) . . ? C1 N1 H1 111(2) . . ? O5 N2 O4 123.8(2) . . ? O5 N2 C16 118.3(2) . . ? O4 N2 C16 117.9(2) . . ? C9 O3 C10 116.55(18) . . ? C1 Se1 C8 85.76(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 N1 C1 C2 C3 -179.6(2) . . . . ? Se1 C1 C2 C3 0.6(3) . . . . ? N1 C1 C2 C9 1.3(4) . . . . ? Se1 C1 C2 C9 -178.46(16) . . . . ? C1 C2 C3 C8 -0.4(3) . . . . ? C9 C2 C3 C8 178.6(2) . . . . ? C1 C2 C3 C4 179.7(2) . . . . ? C9 C2 C3 C4 -1.3(4) . . . . ? C2 C3 C8 C7 179.5(2) . . . . ? C4 C3 C8 C7 -0.6(4) . . . . ? C2 C3 C8 Se1 0.0(3) . . . . ? C4 C3 C8 Se1 179.89(17) . . . . ? C3 C8 C7 C6 18.5(4) . . . . ? Se1 C8 C7 C6 -161.95(19) . . . . ? C8 C7 C6 C5 -46.2(3) . . . . ? C7 C6 C5 C4 59.6(3) . . . . ? C8 C3 C4 C5 10.8(3) . . . . ? C2 C3 C4 C5 -169.4(2) . . . . ? C6 C5 C4 C3 -40.2(3) . . . . ? C1 C2 C9 O2 -2.8(4) . . . . ? C3 C2 C9 O2 178.4(2) . . . . ? C1 C2 C9 O3 176.4(2) . . . . ? C3 C2 C9 O3 -2.5(3) . . . . ? O1 C12 C13 C18 -178.6(2) . . . . ? N1 C12 C13 C18 1.4(4) . . . . ? O1 C12 C13 C14 1.3(4) . . . . ? N1 C12 C13 C14 -178.8(2) . . . . ? C18 C13 C14 C15 1.1(4) . . . . ? C12 C13 C14 C15 -178.7(2) . . . . ? C13 C14 C15 C16 0.0(4) . . . . ? C14 C15 C16 C17 -1.5(4) . . . . ? C14 C15 C16 N2 178.6(2) . . . . ? C15 C16 C17 C18 1.9(4) . . . . ? N2 C16 C17 C18 -178.3(2) . . . . ? C14 C13 C18 C17 -0.7(4) . . . . ? C12 C13 C18 C17 179.1(2) . . . . ? C16 C17 C18 C13 -0.7(4) . . . . ? O1 C12 N1 C1 3.5(4) . . . . ? C13 C12 N1 C1 -176.5(2) . . . . ? C2 C1 N1 C12 178.3(2) . . . . ? Se1 C1 N1 C12 -1.9(3) . . . . ? C15 C16 N2 O5 -179.5(2) . . . . ? C17 C16 N2 O5 0.6(3) . . . . ? C15 C16 N2 O4 0.6(4) . . . . ? C17 C16 N2 O4 -179.2(2) . . . . ? O2 C9 O3 C10 -0.1(3) . . . . ? C2 C9 O3 C10 -179.2(2) . . . . ? C11 C10 O3 C9 169.5(3) . . . . ? C2 C1 Se1 C8 -0.48(18) . . . . ? N1 C1 Se1 C8 179.7(2) . . . . ? C3 C8 Se1 C1 0.27(18) . . . . ? C7 C8 Se1 C1 -179.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.941 _refine_diff_density_max 0.943 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.090