# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email chhbsia@chem.iitb.ac.in _publ_contact_author_name 'Harkesh B. Singh' loop_ _publ_author_name 'K. Selvakumar' 'Harkesh B. Singh' 'Nidhi Goel' 'Udai P. Singh' 'Ray J.Butcher' data_25 _database_code_depnum_ccdc_archive 'CCDC 823627' #TrackingRef 'Combined.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 O4 Se' _chemical_formula_sum 'C18 H16 O4 Se' _chemical_formula_weight 375.27 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' 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' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1010(7) _cell_length_b 10.8845(9) _cell_length_c 17.6635(15) _cell_angle_alpha 90.00 _cell_angle_beta 94.607(4) _cell_angle_gamma 90.00 _cell_volume 1552.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9576 _cell_measurement_theta_min 2.675 _cell_measurement_theta_max 31.563 _exptl_crystal_description chunk _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.606 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 2.437 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.398 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _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 'Oxford Diffraction CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24122 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 33.29 _reflns_number_total 5896 _reflns_number_gt 4213 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1998)' _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^)+(0.0490P)^2^+0.2089P] 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 5896 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0875 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.15771(2) 0.588638(17) 0.647915(10) 0.03174(7) Uani 1 1 d . . . O1 O 0.3602(2) 0.66095(14) 0.45276(9) 0.0540(4) Uani 1 1 d . . . O2 O 0.27731(18) 0.68098(12) 0.56981(8) 0.0394(3) Uani 1 1 d . . . O3 O 0.04766(16) 0.45699(15) 0.70590(7) 0.0400(3) Uani 1 1 d . . . O4 O -0.02760(19) 0.25904(16) 0.69796(8) 0.0505(4) Uani 1 1 d . . . C1 C 0.1102(2) 0.25725(17) 0.54226(10) 0.0335(4) Uani 1 1 d . . . H1A H 0.0659 0.1806 0.5522 0.040 Uiso 1 1 calc R . . C2 C 0.1856(2) 0.27646(17) 0.47405(10) 0.0305(3) Uani 1 1 d . . . C3 C 0.2458(2) 0.39427(16) 0.45843(10) 0.0321(4) Uani 1 1 d . . . H3A H 0.2923 0.4088 0.4128 0.038 Uiso 1 1 calc R . . C4 C 0.2362(2) 0.48923(16) 0.51072(9) 0.0301(3) Uani 1 1 d . . . C5 C 0.1657(2) 0.46272(17) 0.57633(9) 0.0303(3) Uani 1 1 d . . . C6 C 0.1012(2) 0.35123(17) 0.59474(10) 0.0313(4) Uani 1 1 d . . . C7 C 0.2992(2) 0.61883(18) 0.50668(11) 0.0359(4) Uani 1 1 d . . . C8 C 0.0330(2) 0.34898(19) 0.67089(10) 0.0357(4) Uani 1 1 d . . . C9 C 0.2106(2) 0.16673(17) 0.42176(10) 0.0342(4) Uani 1 1 d . . . C10 C 0.3301(4) 0.0782(2) 0.46611(15) 0.0618(7) Uani 1 1 d . . . H10A H 0.4366 0.1165 0.4751 0.093 Uiso 1 1 calc R . . H10B H 0.3408 0.0044 0.4371 0.093 Uiso 1 1 calc R . . H10C H 0.2876 0.0583 0.5138 0.093 Uiso 1 1 calc R . . C11 C 0.0457(3) 0.10151(18) 0.39998(13) 0.0443(5) Uani 1 1 d . . . H11A H -0.0244 0.1542 0.3678 0.066 Uiso 1 1 calc R . . H11B H -0.0079 0.0827 0.4451 0.066 Uiso 1 1 calc R . . H11C H 0.0662 0.0268 0.3734 0.066 Uiso 1 1 calc R . . C12 C 0.2875(3) 0.2044(2) 0.34957(12) 0.0491(5) Uani 1 1 d . . . H12A H 0.2179 0.2640 0.3227 0.074 Uiso 1 1 calc R . . H12B H 0.2983 0.1335 0.3180 0.074 Uiso 1 1 calc R . . H12C H 0.3949 0.2394 0.3624 0.074 Uiso 1 1 calc R . . C13 C 0.3615(2) 0.56868(15) 0.71039(9) 0.0277(3) Uani 1 1 d . . . C14 C 0.3788(2) 0.64005(18) 0.77525(11) 0.0360(4) Uani 1 1 d . . . H14A H 0.2940 0.6919 0.7879 0.043 Uiso 1 1 calc R . . C15 C 0.5256(3) 0.6324(2) 0.82086(12) 0.0455(5) Uani 1 1 d . . . H15A H 0.5407 0.6799 0.8646 0.055 Uiso 1 1 calc R . . C16 C 0.6489(3) 0.5549(2) 0.80158(13) 0.0461(5) Uani 1 1 d . . . H16A H 0.7476 0.5507 0.8322 0.055 Uiso 1 1 calc R . . C17 C 0.6282(2) 0.4833(2) 0.73742(13) 0.0428(5) Uani 1 1 d . . . H17A H 0.7124 0.4305 0.7254 0.051 Uiso 1 1 calc R . . C18 C 0.4836(2) 0.48915(18) 0.69056(10) 0.0354(4) Uani 1 1 d . . . H18A H 0.4689 0.4410 0.6470 0.043 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 0.02852(10) 0.03658(11) 0.02992(10) -0.00302(7) 0.00106(6) 0.00568(7) O1 0.0732(12) 0.0465(9) 0.0446(8) 0.0036(7) 0.0189(8) -0.0106(8) O2 0.0493(8) 0.0317(6) 0.0372(7) -0.0006(5) 0.0031(6) -0.0014(6) O3 0.0312(7) 0.0561(8) 0.0336(7) -0.0050(6) 0.0089(5) -0.0026(6) O4 0.0469(8) 0.0655(10) 0.0405(8) 0.0038(7) 0.0126(6) -0.0194(8) C1 0.0306(8) 0.0359(9) 0.0337(8) 0.0009(7) -0.0001(7) -0.0037(7) C2 0.0282(8) 0.0346(8) 0.0282(8) 0.0004(6) -0.0016(6) 0.0012(7) C3 0.0324(9) 0.0386(9) 0.0253(7) 0.0015(6) 0.0032(6) -0.0003(7) C4 0.0293(8) 0.0332(8) 0.0276(8) 0.0022(6) 0.0003(6) 0.0007(7) C5 0.0274(8) 0.0360(9) 0.0273(8) -0.0018(7) 0.0000(6) 0.0015(7) C6 0.0246(8) 0.0409(10) 0.0283(8) 0.0019(7) 0.0012(6) -0.0024(7) C7 0.0388(10) 0.0350(9) 0.0338(9) 0.0020(7) 0.0019(8) 0.0017(8) C8 0.0249(8) 0.0519(12) 0.0306(8) -0.0016(8) 0.0043(6) -0.0047(8) C9 0.0370(9) 0.0338(9) 0.0312(8) -0.0024(7) -0.0008(7) 0.0039(7) C10 0.0704(17) 0.0607(15) 0.0515(13) -0.0066(11) -0.0125(12) 0.0316(13) C11 0.0542(13) 0.0360(10) 0.0421(11) -0.0047(8) 0.0008(9) -0.0082(9) C12 0.0566(13) 0.0513(13) 0.0411(11) -0.0151(9) 0.0149(9) -0.0083(11) C13 0.0252(8) 0.0300(8) 0.0282(8) 0.0008(6) 0.0034(6) 0.0010(6) C14 0.0373(10) 0.0358(9) 0.0347(9) -0.0065(7) 0.0021(7) 0.0051(8) C15 0.0491(12) 0.0481(11) 0.0375(10) -0.0089(9) -0.0068(9) -0.0006(10) C16 0.0343(10) 0.0541(12) 0.0481(11) 0.0056(10) -0.0081(9) -0.0009(9) C17 0.0296(9) 0.0460(11) 0.0533(12) 0.0026(9) 0.0067(8) 0.0097(8) C18 0.0314(9) 0.0405(10) 0.0351(9) -0.0057(7) 0.0066(7) 0.0037(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 Se1 C5 1.8694(18) . ? Se1 C13 1.9230(17) . ? Se1 O3 2.0109(15) . ? Se1 O2 2.0166(14) . ? O1 C7 1.199(2) . ? O2 C7 1.328(2) . ? O3 C8 1.329(2) . ? O4 C8 1.211(2) . ? C1 C6 1.386(3) . ? C1 C2 1.410(3) . ? C1 H1A 0.9300 . ? C2 C3 1.407(3) . ? C2 C9 1.533(3) . ? C3 C4 1.392(2) . ? C3 H3A 0.9300 . ? C4 C5 1.363(2) . ? C4 C7 1.504(3) . ? C5 C6 1.371(3) . ? C6 C8 1.495(3) . ? C9 C12 1.520(3) . ? C9 C11 1.534(3) . ? C9 C10 1.536(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C18 1.381(2) . ? C13 C14 1.382(2) . ? C14 C15 1.384(3) . ? C14 H14A 0.9300 . ? C15 C16 1.371(3) . ? C15 H15A 0.9300 . ? C16 C17 1.374(3) . ? C16 H16A 0.9300 . ? C17 C18 1.380(3) . ? C17 H17A 0.9300 . ? C18 H18A 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 C5 Se1 C13 103.33(7) . . ? C5 Se1 O3 82.12(7) . . ? C13 Se1 O3 91.29(6) . . ? C5 Se1 O2 81.84(7) . . ? C13 Se1 O2 90.65(7) . . ? O3 Se1 O2 163.86(6) . . ? C7 O2 Se1 115.11(12) . . ? C8 O3 Se1 114.83(12) . . ? C6 C1 C2 120.78(17) . . ? C6 C1 H1A 119.6 . . ? C2 C1 H1A 119.6 . . ? C3 C2 C1 118.92(17) . . ? C3 C2 C9 121.82(16) . . ? C1 C2 C9 119.12(16) . . ? C4 C3 C2 120.52(17) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C5 C4 C3 117.14(17) . . ? C5 C4 C7 113.94(16) . . ? C3 C4 C7 128.88(17) . . ? C4 C5 C6 125.65(17) . . ? C4 C5 Se1 117.35(14) . . ? C6 C5 Se1 117.00(13) . . ? C5 C6 C1 116.94(17) . . ? C5 C6 C8 113.80(16) . . ? C1 C6 C8 129.25(17) . . ? O1 C7 O2 124.30(19) . . ? O1 C7 C4 124.02(18) . . ? O2 C7 C4 111.67(16) . . ? O4 C8 O3 123.73(18) . . ? O4 C8 C6 124.03(18) . . ? O3 C8 C6 112.24(16) . . ? C12 C9 C2 112.22(16) . . ? C12 C9 C11 108.77(16) . . ? C2 C9 C11 110.91(16) . . ? C12 C9 C10 108.3(2) . . ? C2 C9 C10 106.86(15) . . ? C11 C9 C10 109.75(18) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 122.39(16) . . ? C18 C13 Se1 121.66(13) . . ? C14 C13 Se1 115.94(13) . . ? C13 C14 C15 118.28(18) . . ? C13 C14 H14A 120.9 . . ? C15 C14 H14A 120.9 . . ? C16 C15 C14 120.10(19) . . ? C16 C15 H15A 120.0 . . ? C14 C15 H15A 120.0 . . ? C15 C16 C17 120.68(19) . . ? C15 C16 H16A 119.7 . . ? C17 C16 H16A 119.7 . . ? C16 C17 C18 120.67(19) . . ? C16 C17 H17A 119.7 . . ? C18 C17 H17A 119.7 . . ? C17 C18 C13 117.87(18) . . ? C17 C18 H18A 121.1 . . ? C13 C18 H18A 121.1 . . ? 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 C5 Se1 O2 C7 2.86(13) . . . . ? C13 Se1 O2 C7 106.23(13) . . . . ? O3 Se1 O2 C7 9.3(3) . . . . ? C5 Se1 O3 C8 0.66(13) . . . . ? C13 Se1 O3 C8 -102.61(13) . . . . ? O2 Se1 O3 C8 -5.8(3) . . . . ? C6 C1 C2 C3 -2.6(3) . . . . ? C6 C1 C2 C9 173.14(15) . . . . ? C1 C2 C3 C4 2.2(3) . . . . ? C9 C2 C3 C4 -173.42(16) . . . . ? C2 C3 C4 C5 -0.5(3) . . . . ? C2 C3 C4 C7 177.06(17) . . . . ? C3 C4 C5 C6 -1.1(3) . . . . ? C7 C4 C5 C6 -178.94(16) . . . . ? C3 C4 C5 Se1 178.37(13) . . . . ? C7 C4 C5 Se1 0.5(2) . . . . ? C13 Se1 C5 C4 -90.45(14) . . . . ? O3 Se1 C5 C4 -179.91(14) . . . . ? O2 Se1 C5 C4 -1.72(13) . . . . ? C13 Se1 C5 C6 89.02(14) . . . . ? O3 Se1 C5 C6 -0.44(13) . . . . ? O2 Se1 C5 C6 177.75(14) . . . . ? C4 C5 C6 C1 0.7(3) . . . . ? Se1 C5 C6 C1 -178.75(13) . . . . ? C4 C5 C6 C8 179.59(16) . . . . ? Se1 C5 C6 C8 0.2(2) . . . . ? C2 C1 C6 C5 1.2(2) . . . . ? C2 C1 C6 C8 -177.51(16) . . . . ? Se1 O2 C7 O1 176.15(17) . . . . ? Se1 O2 C7 C4 -3.22(19) . . . . ? C5 C4 C7 O1 -177.50(19) . . . . ? C3 C4 C7 O1 4.9(3) . . . . ? C5 C4 C7 O2 1.9(2) . . . . ? C3 C4 C7 O2 -175.71(17) . . . . ? Se1 O3 C8 O4 178.77(15) . . . . ? Se1 O3 C8 C6 -0.72(18) . . . . ? C5 C6 C8 O4 -179.11(18) . . . . ? C1 C6 C8 O4 -0.3(3) . . . . ? C5 C6 C8 O3 0.4(2) . . . . ? C1 C6 C8 O3 179.14(17) . . . . ? C3 C2 C9 C12 -6.5(2) . . . . ? C1 C2 C9 C12 177.87(17) . . . . ? C3 C2 C9 C11 -128.38(18) . . . . ? C1 C2 C9 C11 56.0(2) . . . . ? C3 C2 C9 C10 112.0(2) . . . . ? C1 C2 C9 C10 -63.6(2) . . . . ? C5 Se1 C13 C18 9.58(17) . . . . ? O3 Se1 C13 C18 91.79(16) . . . . ? O2 Se1 C13 C18 -72.19(16) . . . . ? C5 Se1 C13 C14 -171.45(15) . . . . ? O3 Se1 C13 C14 -89.24(15) . . . . ? O2 Se1 C13 C14 106.79(15) . . . . ? C18 C13 C14 C15 1.2(3) . . . . ? Se1 C13 C14 C15 -177.78(16) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C14 C15 C16 C17 -0.5(4) . . . . ? C15 C16 C17 C18 0.8(4) . . . . ? C16 C17 C18 C13 -0.1(3) . . . . ? C14 C13 C18 C17 -0.9(3) . . . . ? Se1 C13 C18 C17 177.99(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C14 H14A O4 0.93 2.31 3.196(2) 158.8 2_556 C18 H18A O1 0.93 2.58 3.346(2) 140.1 3_666 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.347 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.073 #===END data_27 _database_code_depnum_ccdc_archive 'CCDC 823628' #TrackingRef 'Combined.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H26 N2 O2 Se' _chemical_formula_weight 525.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.7943 1.1372 '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 1 21/c 1' 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 10.01795(14) _cell_length_b 24.1373(2) _cell_length_c 11.14207(15) _cell_angle_alpha 90.00 _cell_angle_beta 115.5854(17) _cell_angle_gamma 90.00 _cell_volume 2430.03(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 8105 _cell_measurement_theta_min 4.3960 _cell_measurement_theta_max 77.2898 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3685 _exptl_crystal_size_mid 0.2828 _exptl_crystal_size_min 0.1482 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 2.332 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.94992 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11509 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.77 _diffrn_reflns_theta_max 77.50 _reflns_number_total 5095 _reflns_number_gt 4477 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.0654P)^2^] 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 5095 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0317 _refine_ls_wR_factor_ref 0.0859 _refine_ls_wR_factor_gt 0.0840 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.004 _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 Se Se 0.548062(17) 0.561097(6) 0.677310(16) 0.03274(8) Uani 1 1 d . . . O1 O 0.45096(17) 0.72674(5) 0.63936(15) 0.0502(3) Uani 1 1 d . . . O2 O 0.8404(2) 0.49897(6) 0.5361(2) 0.0654(5) Uani 1 1 d . . . N1 N 0.45768(16) 0.63444(6) 0.69643(15) 0.0370(3) Uani 1 1 d . . . N2 N 0.68236(16) 0.50220(6) 0.63928(15) 0.0376(3) Uani 1 1 d . . . C1 C 0.64415(18) 0.60814(7) 0.60541(16) 0.0337(3) Uani 1 1 d . . . C2 C 0.60862(17) 0.66324(7) 0.59678(16) 0.0345(3) Uani 1 1 d . . . C3 C 0.67959(18) 0.69856(7) 0.54382(16) 0.0369(3) Uani 1 1 d . . . H3A H 0.6577 0.7362 0.5361 0.044 Uiso 1 1 calc R . . C4 C 0.78331(18) 0.67814(7) 0.50214(16) 0.0368(3) Uani 1 1 d . . . C5 C 0.81255(19) 0.62070(7) 0.51172(17) 0.0386(3) Uani 1 1 d . . . H5A H 0.8802 0.6066 0.4831 0.046 Uiso 1 1 calc R . . C6 C 0.74201(18) 0.58510(7) 0.56310(16) 0.0365(3) Uani 1 1 d . . . C7 C 0.49764(19) 0.67948(7) 0.64607(16) 0.0366(3) Uani 1 1 d . . . C8 C 0.35670(18) 0.63635(7) 0.75461(16) 0.0360(3) Uani 1 1 d . . . C9 C 0.24967(19) 0.59503(7) 0.72464(18) 0.0415(3) Uani 1 1 d . . . H9A H 0.2408 0.5677 0.6628 0.050 Uiso 1 1 calc R . . C10 C 0.1564(2) 0.59497(9) 0.7877(2) 0.0501(4) Uani 1 1 d . . . H10A H 0.0865 0.5670 0.7694 0.060 Uiso 1 1 calc R . . C11 C 0.1671(3) 0.63629(9) 0.8775(2) 0.0559(5) Uani 1 1 d . . . H11A H 0.1037 0.6364 0.9185 0.067 Uiso 1 1 calc R . . C12 C 0.2721(2) 0.67740(9) 0.9059(2) 0.0515(4) Uani 1 1 d . . . H12A H 0.2787 0.7052 0.9659 0.062 Uiso 1 1 calc R . . C13 C 0.3678(2) 0.67758(8) 0.84603(18) 0.0414(3) Uani 1 1 d . . . H13A H 0.4392 0.7051 0.8667 0.050 Uiso 1 1 calc R . . C14 C 0.8659(2) 0.71626(8) 0.44734(18) 0.0430(4) Uani 1 1 d . . . C15 C 0.8166(3) 0.77674(9) 0.4386(3) 0.0614(6) Uani 1 1 d . . . H15A H 0.8370 0.7901 0.5259 0.092 Uiso 1 1 calc R . . H15B H 0.7123 0.7793 0.3825 0.092 Uiso 1 1 calc R . . H15C H 0.8696 0.7988 0.4017 0.092 Uiso 1 1 calc R . . C16 C 1.0314(3) 0.71384(13) 0.5389(3) 0.0790(9) Uani 1 1 d . . . H16A H 1.0481 0.7242 0.6275 0.118 Uiso 1 1 calc R . . H16B H 1.0832 0.7390 0.5071 0.118 Uiso 1 1 calc R . . H16C H 1.0670 0.6768 0.5397 0.118 Uiso 1 1 calc R . . C17 C 0.8366(4) 0.69722(12) 0.3076(3) 0.0744(7) Uani 1 1 d . . . H17A H 0.8872 0.7213 0.2723 0.112 Uiso 1 1 calc R . . H17B H 0.7322 0.6984 0.2513 0.112 Uiso 1 1 calc R . . H17C H 0.8719 0.6600 0.3113 0.112 Uiso 1 1 calc R . . C18 C 0.7617(2) 0.52354(7) 0.57742(19) 0.0407(4) Uani 1 1 d . . . C19 C 0.67836(19) 0.44524(7) 0.66883(17) 0.0373(3) Uani 1 1 d . . . C20 C 0.7571(2) 0.40408(8) 0.63851(19) 0.0444(4) Uani 1 1 d . . . H20A H 0.8146 0.4131 0.5945 0.053 Uiso 1 1 calc R . . C21 C 0.7488(3) 0.34927(8) 0.6748(2) 0.0541(5) Uani 1 1 d . . . H21A H 0.8020 0.3221 0.6549 0.065 Uiso 1 1 calc R . . C22 C 0.6641(3) 0.33443(8) 0.7391(2) 0.0550(5) Uani 1 1 d . . . H22A H 0.6607 0.2978 0.7633 0.066 Uiso 1 1 calc R . . C23 C 0.5845(3) 0.37471(9) 0.7671(2) 0.0546(5) Uani 1 1 d . . . H23A H 0.5259 0.3652 0.8097 0.066 Uiso 1 1 calc R . . C24 C 0.5911(3) 0.42933(8) 0.7323(2) 0.0514(5) Uani 1 1 d . . . H24A H 0.5361 0.4560 0.7515 0.062 Uiso 1 1 calc R . . C25 C 0.6811(2) 0.56051(6) 0.86644(17) 0.0362(3) Uani 1 1 d . . . C26 C 0.8315(2) 0.56611(9) 0.9093(2) 0.0502(4) Uani 1 1 d . . . H26A H 0.8710 0.5712 0.8484 0.060 Uiso 1 1 calc R . . C27 C 0.9233(3) 0.56406(10) 1.0450(2) 0.0606(6) Uani 1 1 d . . . H27A H 1.0250 0.5680 1.0754 0.073 Uiso 1 1 calc R . . C28 C 0.8635(3) 0.55614(10) 1.1347(2) 0.0606(6) Uani 1 1 d . . . H28A H 0.9252 0.5543 1.2254 0.073 Uiso 1 1 calc R . . C29 C 0.7124(3) 0.55091(11) 1.0898(2) 0.0627(6) Uani 1 1 d . . . H29A H 0.6725 0.5460 1.1505 0.075 Uiso 1 1 calc R . . C30 C 0.6193(2) 0.55294(10) 0.9546(2) 0.0521(5) Uani 1 1 d . . . H30A H 0.5174 0.5493 0.9240 0.063 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se 0.02930(11) 0.03286(11) 0.03830(11) -0.00101(6) 0.01672(8) -0.00169(5) O1 0.0604(8) 0.0387(6) 0.0642(8) 0.0092(5) 0.0389(7) 0.0128(6) O2 0.0808(11) 0.0407(7) 0.1104(14) -0.0055(7) 0.0749(11) 0.0006(7) N1 0.0355(7) 0.0350(7) 0.0457(7) 0.0005(5) 0.0226(6) 0.0031(5) N2 0.0383(7) 0.0320(7) 0.0481(8) -0.0028(5) 0.0241(6) -0.0001(5) C1 0.0329(7) 0.0355(7) 0.0360(7) 0.0012(6) 0.0180(6) -0.0027(6) C2 0.0332(7) 0.0363(8) 0.0342(7) 0.0016(6) 0.0149(6) 0.0014(6) C3 0.0385(8) 0.0354(7) 0.0375(8) 0.0032(6) 0.0170(6) 0.0007(6) C4 0.0351(8) 0.0420(8) 0.0334(7) 0.0022(6) 0.0148(6) -0.0024(6) C5 0.0364(8) 0.0416(8) 0.0439(8) -0.0018(6) 0.0231(7) -0.0010(7) C6 0.0338(8) 0.0377(8) 0.0408(8) -0.0034(6) 0.0188(6) -0.0017(6) C7 0.0371(8) 0.0361(8) 0.0386(8) 0.0022(6) 0.0184(6) 0.0034(6) C8 0.0314(7) 0.0390(8) 0.0393(8) 0.0019(6) 0.0169(6) 0.0051(6) C9 0.0369(8) 0.0406(8) 0.0476(9) -0.0030(7) 0.0188(7) 0.0009(7) C10 0.0399(9) 0.0506(10) 0.0639(12) 0.0018(9) 0.0264(8) -0.0046(8) C11 0.0537(11) 0.0639(13) 0.0673(13) 0.0002(10) 0.0423(10) -0.0008(9) C12 0.0570(11) 0.0552(11) 0.0523(10) -0.0078(8) 0.0331(9) -0.0010(9) C13 0.0405(8) 0.0410(9) 0.0448(9) -0.0035(7) 0.0205(7) -0.0033(7) C14 0.0422(9) 0.0459(9) 0.0452(9) 0.0092(7) 0.0227(7) -0.0009(7) C15 0.0731(15) 0.0482(11) 0.0771(15) 0.0177(10) 0.0458(13) 0.0014(10) C16 0.0412(11) 0.0906(19) 0.0974(19) 0.0432(16) 0.0227(12) -0.0067(11) C17 0.110(2) 0.0708(15) 0.0637(14) 0.0028(11) 0.0581(15) -0.0117(14) C18 0.0394(8) 0.0364(8) 0.0535(10) -0.0061(7) 0.0269(7) -0.0040(7) C19 0.0346(8) 0.0340(8) 0.0402(8) -0.0045(6) 0.0131(6) -0.0045(6) C20 0.0433(9) 0.0382(8) 0.0517(10) -0.0032(7) 0.0204(8) -0.0009(7) C21 0.0605(12) 0.0357(9) 0.0641(12) -0.0019(8) 0.0250(10) 0.0064(8) C22 0.0678(13) 0.0350(9) 0.0558(11) 0.0022(8) 0.0206(10) -0.0037(9) C23 0.0629(12) 0.0450(10) 0.0628(12) 0.0027(8) 0.0336(10) -0.0089(9) C24 0.0578(12) 0.0387(9) 0.0698(13) -0.0010(9) 0.0390(11) -0.0007(8) C25 0.0362(8) 0.0338(8) 0.0368(8) 0.0011(6) 0.0140(6) 0.0006(6) C26 0.0390(10) 0.0614(12) 0.0487(10) -0.0025(8) 0.0175(8) -0.0050(8) C27 0.0422(11) 0.0737(15) 0.0540(12) -0.0039(9) 0.0096(9) -0.0045(9) C28 0.0624(14) 0.0641(13) 0.0414(10) -0.0009(8) 0.0094(9) 0.0007(10) C29 0.0660(14) 0.0795(15) 0.0468(11) 0.0076(10) 0.0285(11) 0.0007(12) C30 0.0444(10) 0.0676(13) 0.0459(10) 0.0069(8) 0.0210(8) 0.0015(9) _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 Se C1 1.8772(15) . ? Se C25 1.9472(17) . ? Se N1 2.0411(13) . ? Se N2 2.1220(13) . ? O1 C7 1.223(2) . ? O2 C18 1.224(2) . ? N1 C7 1.360(2) . ? N1 C8 1.419(2) . ? N2 C18 1.358(2) . ? N2 C19 1.418(2) . ? C1 C2 1.369(2) . ? C1 C6 1.375(2) . ? C2 C3 1.394(2) . ? C2 C7 1.490(2) . ? C3 C4 1.398(2) . ? C3 H3A 0.9300 . ? C4 C5 1.411(2) . ? C4 C14 1.530(2) . ? C5 C6 1.384(2) . ? C5 H5A 0.9300 . ? C6 C18 1.498(2) . ? C8 C13 1.394(2) . ? C8 C9 1.395(2) . ? C9 C10 1.390(3) . ? C9 H9A 0.9300 . ? C10 C11 1.384(3) . ? C10 H10A 0.9300 . ? C11 C12 1.380(3) . ? C11 H11A 0.9300 . ? C12 C13 1.384(2) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C17 1.525(3) . ? C14 C16 1.527(3) . ? C14 C15 1.531(3) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C19 C24 1.395(3) . ? C19 C20 1.398(2) . ? C20 C21 1.396(3) . ? C20 H20A 0.9300 . ? C21 C22 1.373(3) . ? C21 H21A 0.9300 . ? C22 C23 1.376(3) . ? C22 H22A 0.9300 . ? C23 C24 1.384(3) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? C25 C26 1.376(3) . ? C25 C30 1.381(3) . ? C26 C27 1.390(3) . ? C26 H26A 0.9300 . ? C27 C28 1.383(4) . ? C27 H27A 0.9300 . ? C28 C29 1.380(4) . ? C28 H28A 0.9300 . ? C29 C30 1.389(3) . ? C29 H29A 0.9300 . ? C30 H30A 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 Se C25 103.22(7) . . ? C1 Se N1 81.50(6) . . ? C25 Se N1 91.18(6) . . ? C1 Se N2 80.44(6) . . ? C25 Se N2 90.83(7) . . ? N1 Se N2 161.81(6) . . ? C7 N1 C8 123.88(14) . . ? C7 N1 Se 115.29(10) . . ? C8 N1 Se 120.79(11) . . ? C18 N2 C19 124.52(14) . . ? C18 N2 Se 114.06(11) . . ? C19 N2 Se 121.28(11) . . ? C2 C1 C6 124.80(15) . . ? C2 C1 Se 116.86(11) . . ? C6 C1 Se 118.32(12) . . ? C1 C2 C3 117.33(15) . . ? C1 C2 C7 116.26(14) . . ? C3 C2 C7 126.40(15) . . ? C2 C3 C4 120.86(15) . . ? C2 C3 H3A 119.6 . . ? C4 C3 H3A 119.6 . . ? C3 C4 C5 118.75(15) . . ? C3 C4 C14 121.87(16) . . ? C5 C4 C14 119.38(15) . . ? C6 C5 C4 120.98(15) . . ? C6 C5 H5A 119.5 . . ? C4 C5 H5A 119.5 . . ? C1 C6 C5 117.24(15) . . ? C1 C6 C18 116.43(14) . . ? C5 C6 C18 126.34(14) . . ? O1 C7 N1 126.71(15) . . ? O1 C7 C2 123.34(15) . . ? N1 C7 C2 109.95(14) . . ? C13 C8 C9 119.72(15) . . ? C13 C8 N1 120.65(15) . . ? C9 C8 N1 119.57(15) . . ? C10 C9 C8 119.63(17) . . ? C10 C9 H9A 120.2 . . ? C8 C9 H9A 120.2 . . ? C11 C10 C9 120.36(18) . . ? C11 C10 H10A 119.8 . . ? C9 C10 H10A 119.8 . . ? C12 C11 C10 119.86(17) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? C11 C12 C13 120.62(18) . . ? C11 C12 H12A 119.7 . . ? C13 C12 H12A 119.7 . . ? C12 C13 C8 119.79(18) . . ? C12 C13 H13A 120.1 . . ? C8 C13 H13A 120.1 . . ? C17 C14 C16 110.2(2) . . ? C17 C14 C4 109.10(17) . . ? C16 C14 C4 109.18(15) . . ? C17 C14 C15 107.91(19) . . ? C16 C14 C15 107.8(2) . . ? C4 C14 C15 112.59(15) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O2 C18 N2 128.32(17) . . ? O2 C18 C6 121.13(16) . . ? N2 C18 C6 110.55(14) . . ? C24 C19 C20 118.01(17) . . ? C24 C19 N2 118.12(16) . . ? C20 C19 N2 123.88(16) . . ? C21 C20 C19 119.53(18) . . ? C21 C20 H20A 120.2 . . ? C19 C20 H20A 120.2 . . ? C22 C21 C20 121.72(19) . . ? C22 C21 H21A 119.1 . . ? C20 C21 H21A 119.1 . . ? C21 C22 C23 118.88(19) . . ? C21 C22 H22A 120.6 . . ? C23 C22 H22A 120.6 . . ? C22 C23 C24 120.5(2) . . ? C22 C23 H23A 119.8 . . ? C24 C23 H23A 119.8 . . ? C23 C24 C19 121.36(19) . . ? C23 C24 H24A 119.3 . . ? C19 C24 H24A 119.3 . . ? C26 C25 C30 121.74(18) . . ? C26 C25 Se 120.67(14) . . ? C30 C25 Se 117.57(14) . . ? C25 C26 C27 119.0(2) . . ? C25 C26 H26A 120.5 . . ? C27 C26 H26A 120.5 . . ? C28 C27 C26 120.1(2) . . ? C28 C27 H27A 120.0 . . ? C26 C27 H27A 120.0 . . ? C29 C28 C27 120.0(2) . . ? C29 C28 H28A 120.0 . . ? C27 C28 H28A 120.0 . . ? C28 C29 C30 120.5(2) . . ? C28 C29 H29A 119.7 . . ? C30 C29 H29A 119.7 . . ? C25 C30 C29 118.6(2) . . ? C25 C30 H30A 120.7 . . ? C29 C30 H30A 120.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 Se N1 C7 3.36(13) . . . . ? C25 Se N1 C7 106.55(13) . . . . ? N2 Se N1 C7 10.3(3) . . . . ? C1 Se N1 C8 -178.70(14) . . . . ? C25 Se N1 C8 -75.51(14) . . . . ? N2 Se N1 C8 -171.77(16) . . . . ? C1 Se N2 C18 -3.86(13) . . . . ? C25 Se N2 C18 -107.13(14) . . . . ? N1 Se N2 C18 -10.8(3) . . . . ? C1 Se N2 C19 -179.65(14) . . . . ? C25 Se N2 C19 77.08(14) . . . . ? N1 Se N2 C19 173.40(16) . . . . ? C25 Se C1 C2 -91.02(13) . . . . ? N1 Se C1 C2 -1.80(13) . . . . ? N2 Se C1 C2 -179.61(14) . . . . ? C25 Se C1 C6 90.22(14) . . . . ? N1 Se C1 C6 179.43(14) . . . . ? N2 Se C1 C6 1.62(13) . . . . ? C6 C1 C2 C3 -1.5(3) . . . . ? Se C1 C2 C3 179.86(12) . . . . ? C6 C1 C2 C7 178.84(16) . . . . ? Se C1 C2 C7 0.2(2) . . . . ? C1 C2 C3 C4 -0.3(2) . . . . ? C7 C2 C3 C4 179.32(16) . . . . ? C2 C3 C4 C5 1.5(2) . . . . ? C2 C3 C4 C14 -178.25(16) . . . . ? C3 C4 C5 C6 -1.0(2) . . . . ? C14 C4 C5 C6 178.78(16) . . . . ? C2 C1 C6 C5 2.0(3) . . . . ? Se C1 C6 C5 -179.37(13) . . . . ? C2 C1 C6 C18 -178.04(16) . . . . ? Se C1 C6 C18 0.6(2) . . . . ? C4 C5 C6 C1 -0.7(3) . . . . ? C4 C5 C6 C18 179.32(16) . . . . ? C8 N1 C7 O1 -2.4(3) . . . . ? Se N1 C7 O1 175.44(15) . . . . ? C8 N1 C7 C2 178.22(15) . . . . ? Se N1 C7 C2 -3.92(18) . . . . ? C1 C2 C7 O1 -176.84(17) . . . . ? C3 C2 C7 O1 3.5(3) . . . . ? C1 C2 C7 N1 2.5(2) . . . . ? C3 C2 C7 N1 -177.11(16) . . . . ? C7 N1 C8 C13 -45.8(3) . . . . ? Se N1 C8 C13 136.46(14) . . . . ? C7 N1 C8 C9 137.22(18) . . . . ? Se N1 C8 C9 -40.5(2) . . . . ? C13 C8 C9 C10 -0.9(3) . . . . ? N1 C8 C9 C10 176.15(17) . . . . ? C8 C9 C10 C11 1.4(3) . . . . ? C9 C10 C11 C12 -0.8(4) . . . . ? C10 C11 C12 C13 -0.4(4) . . . . ? C11 C12 C13 C8 0.9(3) . . . . ? C9 C8 C13 C12 -0.3(3) . . . . ? N1 C8 C13 C12 -177.30(18) . . . . ? C3 C4 C14 C17 -122.3(2) . . . . ? C5 C4 C14 C17 57.9(2) . . . . ? C3 C4 C14 C16 117.2(2) . . . . ? C5 C4 C14 C16 -62.6(2) . . . . ? C3 C4 C14 C15 -2.6(2) . . . . ? C5 C4 C14 C15 177.70(18) . . . . ? C19 N2 C18 O2 0.6(3) . . . . ? Se N2 C18 O2 -175.0(2) . . . . ? C19 N2 C18 C6 -179.46(15) . . . . ? Se N2 C18 C6 4.91(19) . . . . ? C1 C6 C18 O2 176.1(2) . . . . ? C5 C6 C18 O2 -3.9(3) . . . . ? C1 C6 C18 N2 -3.8(2) . . . . ? C5 C6 C18 N2 176.17(17) . . . . ? C18 N2 C19 C24 -179.66(19) . . . . ? Se N2 C19 C24 -4.3(2) . . . . ? C18 N2 C19 C20 0.5(3) . . . . ? Se N2 C19 C20 175.87(14) . . . . ? C24 C19 C20 C21 -1.4(3) . . . . ? N2 C19 C20 C21 178.37(18) . . . . ? C19 C20 C21 C22 0.4(3) . . . . ? C20 C21 C22 C23 0.6(3) . . . . ? C21 C22 C23 C24 -0.7(4) . . . . ? C22 C23 C24 C19 -0.3(4) . . . . ? C20 C19 C24 C23 1.4(3) . . . . ? N2 C19 C24 C23 -178.4(2) . . . . ? C1 Se C25 C26 -31.48(16) . . . . ? N1 Se C25 C26 -113.03(15) . . . . ? N2 Se C25 C26 48.89(15) . . . . ? C1 Se C25 C30 150.07(15) . . . . ? N1 Se C25 C30 68.53(15) . . . . ? N2 Se C25 C30 -129.56(15) . . . . ? C30 C25 C26 C27 0.0(3) . . . . ? Se C25 C26 C27 -178.36(16) . . . . ? C25 C26 C27 C28 0.4(3) . . . . ? C26 C27 C28 C29 -0.8(4) . . . . ? C27 C28 C29 C30 0.7(4) . . . . ? C26 C25 C30 C29 -0.1(3) . . . . ? Se C25 C30 C29 178.33(17) . . . . ? C28 C29 C30 C25 -0.3(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C9 H9A O2 0.93 2.57 3.484(3) 167.5 3_666 C12 H12A O1 0.93 2.56 3.362(3) 145.4 4_576 C22 H22A O1 0.93 2.53 3.357(2) 147.9 2_646 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 67.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.671 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.057 #===END data_29 _database_code_depnum_ccdc_archive 'CCDC 823629' #TrackingRef 'Combined.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H22 O4 Se' _chemical_formula_sum 'C20 H22 O4 Se' _chemical_formula_weight 405.34 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' 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/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.292(3) _cell_length_b 10.3574(19) _cell_length_c 15.966(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.061(8) _cell_angle_gamma 90.00 _cell_volume 1864.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9546 _cell_measurement_theta_min 2.634 _cell_measurement_theta_max 31.012 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 2.034 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6273 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _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 'Bruker Apex 2' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17061 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.27 _reflns_number_total 4053 _reflns_number_gt 3315 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker Apex 2' _computing_cell_refinement 'Bruker Apex 2' _computing_data_reduction 'Bruker Apex 2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1998)' _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^)+(0.0426P)^2^+0.3395P] 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 4053 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0789 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 Se1 Se 0.486829(18) 0.238947(18) 0.173333(12) 0.03671(8) Uani 1 1 d . . . O1 O 0.38875(14) 0.02778(13) 0.25987(10) 0.0468(4) Uani 1 1 d . . . O2 O 0.41636(13) 0.02357(12) 0.39994(9) 0.0426(3) Uani 1 1 d . . . O3 O 0.36617(13) 0.52848(14) 0.14445(8) 0.0438(3) Uani 1 1 d . . . O4 O 0.47270(14) 0.64024(13) 0.24171(8) 0.0445(4) Uani 1 1 d . . . C1 C 0.41707(15) 0.30877(18) 0.27114(11) 0.0279(4) Uani 1 1 d . . . C2 C 0.39798(15) 0.44076(17) 0.28256(11) 0.0283(4) Uani 1 1 d . . . C3 C 0.35708(15) 0.48672(17) 0.35732(11) 0.0289(4) Uani 1 1 d . . . H3A H 0.3472 0.5752 0.3637 0.035 Uiso 1 1 calc R . . C4 C 0.33038(15) 0.40591(16) 0.42291(11) 0.0268(4) Uani 1 1 d . . . C5 C 0.34543(16) 0.27477(17) 0.40976(12) 0.0307(4) Uani 1 1 d . . . H5A H 0.3262 0.2176 0.4518 0.037 Uiso 1 1 calc R . . C6 C 0.38810(16) 0.22529(17) 0.33633(12) 0.0294(4) Uani 1 1 d . . . C7 C 0.28054(16) 0.45606(17) 0.50409(11) 0.0311(4) Uani 1 1 d . . . C8 C 0.3084(2) 0.5989(2) 0.51829(14) 0.0566(6) Uani 1 1 d . . . H8A H 0.2796 0.6257 0.5711 0.085 Uiso 1 1 calc R . . H8B H 0.2705 0.6489 0.4739 0.085 Uiso 1 1 calc R . . H8C H 0.3926 0.6119 0.5188 0.085 Uiso 1 1 calc R . . C9 C 0.3326(2) 0.3798(2) 0.57981(12) 0.0457(5) Uani 1 1 d . . . H9A H 0.3001 0.4119 0.6301 0.069 Uiso 1 1 calc R . . H9B H 0.4173 0.3899 0.5837 0.069 Uiso 1 1 calc R . . H9C H 0.3132 0.2901 0.5730 0.069 Uiso 1 1 calc R . . C10 C 0.14657(18) 0.4379(2) 0.49785(14) 0.0506(6) Uani 1 1 d . . . H10A H 0.1134 0.4694 0.5481 0.076 Uiso 1 1 calc R . . H10B H 0.1284 0.3478 0.4912 0.076 Uiso 1 1 calc R . . H10C H 0.1134 0.4849 0.4504 0.076 Uiso 1 1 calc R . . C11 C 0.60226(16) 0.36982(18) 0.15402(11) 0.0324(4) Uani 1 1 d . . . C12 C 0.68637(19) 0.4047(2) 0.21627(13) 0.0447(5) Uani 1 1 d . . . H12A H 0.6843 0.3683 0.2694 0.054 Uiso 1 1 calc R . . C13 C 0.7734(2) 0.4936(2) 0.19956(15) 0.0541(6) Uani 1 1 d . . . H13A H 0.8285 0.5188 0.2418 0.065 Uiso 1 1 calc R . . C14 C 0.7785(2) 0.5450(2) 0.11998(16) 0.0534(6) Uani 1 1 d . . . H14A H 0.8371 0.6046 0.1087 0.064 Uiso 1 1 calc R . . C15 C 0.6970(2) 0.5082(2) 0.05757(14) 0.0488(5) Uani 1 1 d . . . H15A H 0.7015 0.5415 0.0037 0.059 Uiso 1 1 calc R . . C16 C 0.60845(18) 0.4217(2) 0.07484(12) 0.0392(5) Uani 1 1 d . . . H16A H 0.5525 0.3983 0.0327 0.047 Uiso 1 1 calc R . . C17 C 0.39753(16) 0.08338(18) 0.32627(13) 0.0340(4) Uani 1 1 d . . . C18 C 0.4183(2) -0.1152(2) 0.39687(17) 0.0600(7) Uani 1 1 d . . . H18A H 0.4364 -0.1487 0.4521 0.090 Uiso 1 1 calc R . . H18B H 0.4778 -0.1430 0.3600 0.090 Uiso 1 1 calc R . . H18D H 0.3422 -0.1464 0.3764 0.090 Uiso 1 1 calc R . . C19 C 0.41017(16) 0.53814(18) 0.21394(11) 0.0313(4) Uani 1 1 d . . . C20 C 0.4876(3) 0.7424(2) 0.18151(15) 0.0606(8) Uani 1 1 d . . . H20D H 0.5427 0.8050 0.2048 0.091 Uiso 1 1 calc R . . H20A H 0.4125 0.7832 0.1685 0.091 Uiso 1 1 calc R . . H20B H 0.5174 0.7068 0.1313 0.091 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 0.04408(13) 0.03333(13) 0.03370(12) -0.00859(8) 0.01122(9) -0.00105(8) O1 0.0599(10) 0.0319(8) 0.0494(9) -0.0094(7) 0.0108(7) -0.0042(7) O2 0.0536(9) 0.0262(7) 0.0487(9) 0.0029(6) 0.0101(7) 0.0053(6) O3 0.0502(9) 0.0515(9) 0.0293(7) 0.0042(6) -0.0023(6) 0.0056(7) O4 0.0688(10) 0.0298(7) 0.0349(7) 0.0057(6) 0.0035(7) -0.0061(7) C1 0.0263(9) 0.0307(10) 0.0268(9) -0.0045(7) 0.0026(7) -0.0002(7) C2 0.0278(9) 0.0293(10) 0.0278(9) -0.0004(7) 0.0020(7) 0.0016(7) C3 0.0296(9) 0.0252(9) 0.0319(9) -0.0013(7) 0.0010(7) 0.0022(7) C4 0.0237(8) 0.0278(9) 0.0288(9) -0.0008(7) 0.0022(7) -0.0005(7) C5 0.0307(9) 0.0299(10) 0.0320(9) 0.0016(8) 0.0067(8) -0.0014(7) C6 0.0260(9) 0.0262(9) 0.0363(10) -0.0025(8) 0.0038(7) -0.0003(7) C7 0.0339(10) 0.0304(10) 0.0298(9) -0.0011(8) 0.0084(8) 0.0009(7) C8 0.0900(19) 0.0365(13) 0.0458(13) -0.0118(10) 0.0265(12) -0.0058(12) C9 0.0556(14) 0.0503(13) 0.0314(10) -0.0018(9) 0.0032(9) 0.0055(10) C10 0.0365(12) 0.0698(16) 0.0468(13) -0.0017(11) 0.0130(10) 0.0068(10) C11 0.0330(10) 0.0339(10) 0.0310(9) -0.0036(8) 0.0081(8) 0.0050(8) C12 0.0446(12) 0.0603(14) 0.0294(10) -0.0004(9) 0.0040(9) -0.0009(10) C13 0.0404(12) 0.0724(17) 0.0494(13) -0.0105(12) 0.0001(10) -0.0092(11) C14 0.0444(13) 0.0538(15) 0.0636(16) 0.0032(12) 0.0166(11) -0.0073(10) C15 0.0484(13) 0.0569(15) 0.0422(12) 0.0094(10) 0.0124(10) 0.0021(10) C16 0.0411(11) 0.0451(12) 0.0314(10) -0.0010(9) 0.0013(9) 0.0048(9) C17 0.0298(10) 0.0275(10) 0.0454(11) -0.0010(9) 0.0099(8) -0.0007(7) C18 0.0852(19) 0.0265(11) 0.0699(16) 0.0085(11) 0.0202(14) 0.0085(11) C19 0.0338(10) 0.0297(10) 0.0307(10) 0.0000(8) 0.0063(8) 0.0087(7) C20 0.100(2) 0.0348(14) 0.0489(15) 0.0129(10) 0.0177(15) -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 C11 1.9169(19) . ? Se1 C1 1.9270(18) . ? Se1 O1 2.8430(15) . ? O1 C17 1.206(2) . ? O2 C17 1.336(2) . ? O2 C18 1.438(2) . ? O3 C19 1.195(2) . ? O4 C19 1.334(2) . ? O4 C20 1.445(2) . ? C1 C2 1.397(3) . ? C1 C6 1.405(3) . ? C2 C3 1.387(2) . ? C2 C19 1.501(3) . ? C3 C4 1.386(2) . ? C3 H3A 0.9300 . ? C4 C5 1.386(2) . ? C4 C7 1.531(2) . ? C5 C6 1.389(3) . ? C5 H5A 0.9300 . ? C6 C17 1.483(2) . ? C7 C10 1.522(3) . ? C7 C8 1.527(3) . ? C7 C9 1.535(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C16 1.379(3) . ? C11 C12 1.386(3) . ? C12 C13 1.383(3) . ? C12 H12A 0.9300 . ? C13 C14 1.381(3) . ? C13 H13A 0.9300 . ? C14 C15 1.373(3) . ? C14 H14A 0.9300 . ? C15 C16 1.382(3) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18D 0.9600 . ? C20 H20D 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? 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 C11 Se1 C1 100.13(8) . . ? C11 Se1 O1 155.24(6) . . ? C1 Se1 O1 73.03(6) . . ? C17 O1 Se1 92.52(12) . . ? C17 O2 C18 115.80(17) . . ? C19 O4 C20 115.94(16) . . ? C2 C1 C6 117.50(16) . . ? C2 C1 Se1 123.05(13) . . ? C6 C1 Se1 119.39(14) . . ? C3 C2 C1 120.58(16) . . ? C3 C2 C19 116.44(16) . . ? C1 C2 C19 122.78(16) . . ? C4 C3 C2 122.60(17) . . ? C4 C3 H3A 118.7 . . ? C2 C3 H3A 118.7 . . ? C5 C4 C3 116.35(17) . . ? C5 C4 C7 120.94(16) . . ? C3 C4 C7 122.63(16) . . ? C4 C5 C6 122.69(17) . . ? C4 C5 H5A 118.7 . . ? C6 C5 H5A 118.7 . . ? C5 C6 C1 120.21(16) . . ? C5 C6 C17 119.16(17) . . ? C1 C6 C17 120.58(17) . . ? C10 C7 C8 109.02(18) . . ? C10 C7 C4 108.15(15) . . ? C8 C7 C4 111.85(16) . . ? C10 C7 C9 109.01(17) . . ? C8 C7 C9 108.30(17) . . ? C4 C7 C9 110.46(15) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 119.30(19) . . ? C16 C11 Se1 119.43(14) . . ? C12 C11 Se1 121.01(15) . . ? C13 C12 C11 120.2(2) . . ? C13 C12 H12A 119.9 . . ? C11 C12 H12A 119.9 . . ? C14 C13 C12 119.9(2) . . ? C14 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? C15 C14 C13 120.1(2) . . ? C15 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C14 C15 C16 119.9(2) . . ? C14 C15 H15A 120.0 . . ? C16 C15 H15A 120.0 . . ? C11 C16 C15 120.57(19) . . ? C11 C16 H16A 119.7 . . ? C15 C16 H16A 119.7 . . ? O1 C17 O2 123.65(17) . . ? O1 C17 C6 124.44(19) . . ? O2 C17 C6 111.91(17) . . ? O2 C18 H18A 109.5 . . ? O2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O2 C18 H18D 109.5 . . ? H18A C18 H18D 109.5 . . ? H18B C18 H18D 109.5 . . ? O3 C19 O4 124.13(18) . . ? O3 C19 C2 124.86(18) . . ? O4 C19 C2 110.95(15) . . ? O4 C20 H20D 109.5 . . ? O4 C20 H20A 109.5 . . ? H20D C20 H20A 109.5 . . ? O4 C20 H20B 109.5 . . ? H20D C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? 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 C11 Se1 O1 C17 51.4(2) . . . . ? C1 Se1 O1 C17 -25.72(12) . . . . ? C11 Se1 C1 C2 37.37(16) . . . . ? O1 Se1 C1 C2 -167.13(16) . . . . ? C11 Se1 C1 C6 -139.81(14) . . . . ? O1 Se1 C1 C6 15.68(13) . . . . ? C6 C1 C2 C3 2.9(2) . . . . ? Se1 C1 C2 C3 -174.34(13) . . . . ? C6 C1 C2 C19 -171.89(16) . . . . ? Se1 C1 C2 C19 10.9(2) . . . . ? C1 C2 C3 C4 -1.7(3) . . . . ? C19 C2 C3 C4 173.42(16) . . . . ? C2 C3 C4 C5 -0.7(3) . . . . ? C2 C3 C4 C7 -177.49(16) . . . . ? C3 C4 C5 C6 1.8(3) . . . . ? C7 C4 C5 C6 178.67(17) . . . . ? C4 C5 C6 C1 -0.6(3) . . . . ? C4 C5 C6 C17 -177.90(17) . . . . ? C2 C1 C6 C5 -1.8(3) . . . . ? Se1 C1 C6 C5 175.53(13) . . . . ? C2 C1 C6 C17 175.47(17) . . . . ? Se1 C1 C6 C17 -7.2(2) . . . . ? C5 C4 C7 C10 -78.5(2) . . . . ? C3 C4 C7 C10 98.1(2) . . . . ? C5 C4 C7 C8 161.40(18) . . . . ? C3 C4 C7 C8 -22.0(2) . . . . ? C5 C4 C7 C9 40.7(2) . . . . ? C3 C4 C7 C9 -142.68(18) . . . . ? C1 Se1 C11 C16 -130.17(15) . . . . ? O1 Se1 C11 C16 158.52(13) . . . . ? C1 Se1 C11 C12 55.68(17) . . . . ? O1 Se1 C11 C12 -15.6(3) . . . . ? C16 C11 C12 C13 1.9(3) . . . . ? Se1 C11 C12 C13 176.02(17) . . . . ? C11 C12 C13 C14 -1.8(3) . . . . ? C12 C13 C14 C15 0.2(4) . . . . ? C13 C14 C15 C16 1.4(4) . . . . ? C12 C11 C16 C15 -0.3(3) . . . . ? Se1 C11 C16 C15 -174.59(16) . . . . ? C14 C15 C16 C11 -1.3(3) . . . . ? Se1 O1 C17 O2 -148.91(17) . . . . ? Se1 O1 C17 C6 31.48(19) . . . . ? C18 O2 C17 O1 -3.9(3) . . . . ? C18 O2 C17 C6 175.76(17) . . . . ? C5 C6 C17 O1 150.48(19) . . . . ? C1 C6 C17 O1 -26.8(3) . . . . ? C5 C6 C17 O2 -29.2(2) . . . . ? C1 C6 C17 O2 153.53(16) . . . . ? C20 O4 C19 O3 -1.0(3) . . . . ? C20 O4 C19 C2 -178.40(17) . . . . ? C3 C2 C19 O3 -126.0(2) . . . . ? C1 C2 C19 O3 49.0(3) . . . . ? C3 C2 C19 O4 51.3(2) . . . . ? C1 C2 C19 O4 -133.71(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C15 H15A O3 0.93 2.55 3.288(3) 136.3 3_665 _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.259 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.059 #===END data_31 _database_code_depnum_ccdc_archive 'CCDC 823630' #TrackingRef 'Combined.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 O2 Se' _chemical_formula_sum 'C18 H22 O2 Se' _chemical_formula_weight 349.32 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' 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 1 21/n 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.4749(4) _cell_length_b 20.7654(6) _cell_length_c 9.4830(5) _cell_angle_alpha 90.00 _cell_angle_beta 119.536(6) _cell_angle_gamma 90.00 _cell_volume 1623.31(15) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9034 _cell_measurement_theta_min 4.6862 _cell_measurement_theta_max 32.4491 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 2.315 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.50754 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 19227 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.70 _diffrn_reflns_theta_max 32.53 _reflns_number_total 5417 _reflns_number_gt 3654 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0173P)^2^+6.7024P] 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 SHELXL _refine_ls_extinction_coef 0.0054(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5417 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0934 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1396 _refine_ls_wR_factor_gt 0.1337 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.135 _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 Se Se 0.86382(5) 0.03943(2) 0.76405(5) 0.03172(14) Uani 1 1 d . . . O1 O 0.5525(4) 0.06064(15) 0.2162(3) 0.0343(7) Uani 1 1 d . . . H1O H 0.4919 0.0286 0.1743 0.041 Uiso 1 1 calc R . . O2 O 0.6342(4) 0.04015(15) 0.9718(4) 0.0377(7) Uani 1 1 d . . . H2O H 0.6324 0.0454 1.0588 0.045 Uiso 1 1 calc R . . C1 C 0.6497(4) 0.07637(17) 0.6487(4) 0.0218(7) Uani 1 1 d . . . C2 C 0.5772(5) 0.10065(18) 0.7353(4) 0.0254(8) Uani 1 1 d . . . C3 C 0.4235(4) 0.12660(19) 0.6495(5) 0.0254(8) Uani 1 1 d . . . H3A H 0.3746 0.1437 0.7081 0.030 Uiso 1 1 calc R . . C4 C 0.3376(4) 0.12879(17) 0.4822(4) 0.0213(7) Uani 1 1 d . . . C5 C 0.4123(4) 0.10419(18) 0.3983(4) 0.0224(7) Uani 1 1 d . . . H5A H 0.3556 0.1052 0.2832 0.027 Uiso 1 1 calc R . . C6 C 0.5678(4) 0.07823(17) 0.4793(4) 0.0212(7) Uani 1 1 d . . . C7 C 0.6463(5) 0.0517(2) 0.3851(5) 0.0293(8) Uani 1 1 d . . . H7A H 0.7528 0.0729 0.4242 0.035 Uiso 1 1 calc R . . H7B H 0.6663 0.0051 0.4079 0.035 Uiso 1 1 calc R . . C8 C 0.6604(5) 0.1000(2) 0.9180(5) 0.0299(9) Uani 1 1 d . . . H8A H 0.7782 0.1072 0.9635 0.036 Uiso 1 1 calc R . . H8B H 0.6169 0.1352 0.9562 0.036 Uiso 1 1 calc R . . C9 C 0.1668(4) 0.15899(19) 0.3957(5) 0.0252(8) Uani 1 1 d . . . C10 C 0.1778(5) 0.2294(2) 0.4538(6) 0.0373(10) Uani 1 1 d . . . H10A H 0.0723 0.2505 0.3901 0.056 Uiso 1 1 calc R . . H10B H 0.2600 0.2525 0.4395 0.056 Uiso 1 1 calc R . . H10C H 0.2081 0.2297 0.5687 0.056 Uiso 1 1 calc R . . C11 C 0.0548(5) 0.1211(2) 0.4365(6) 0.0387(10) Uani 1 1 d . . . H11A H 0.0429 0.0771 0.3943 0.058 Uiso 1 1 calc R . . H11B H -0.0517 0.1420 0.3872 0.058 Uiso 1 1 calc R . . H11C H 0.1009 0.1196 0.5544 0.058 Uiso 1 1 calc R . . C12 C 0.0942(5) 0.1606(2) 0.2125(5) 0.0359(10) Uani 1 1 d . . . H12A H 0.0732 0.1165 0.1702 0.054 Uiso 1 1 calc R . . H12B H 0.1704 0.1815 0.1853 0.054 Uiso 1 1 calc R . . H12C H -0.0078 0.1848 0.1639 0.054 Uiso 1 1 calc R . . C13 C 0.9912(4) 0.1159(2) 0.8069(4) 0.0258(8) Uani 1 1 d . . . C14 C 1.1594(5) 0.1077(2) 0.8947(5) 0.0318(9) Uani 1 1 d . . . H14A H 1.2050 0.0660 0.9276 0.038 Uiso 1 1 calc R . . C15 C 1.2589(5) 0.1614(3) 0.9331(5) 0.0390(11) Uani 1 1 d . . . H15A H 1.3733 0.1563 0.9939 0.047 Uiso 1 1 calc R . . C16 C 1.1945(6) 0.2216(3) 0.8845(5) 0.0400(11) Uani 1 1 d . . . H16A H 1.2641 0.2578 0.9096 0.048 Uiso 1 1 calc R . . C17 C 1.0296(6) 0.2297(2) 0.7998(6) 0.0383(10) Uani 1 1 d . . . H17A H 0.9853 0.2717 0.7688 0.046 Uiso 1 1 calc R . . C18 C 0.9264(5) 0.1770(2) 0.7588(5) 0.0308(9) Uani 1 1 d . . . H18A H 0.8122 0.1828 0.6981 0.037 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 Se 0.02636(19) 0.0274(2) 0.0322(2) 0.00317(19) 0.00743(15) 0.00523(17) O1 0.0411(17) 0.0410(17) 0.0245(14) 0.0001(12) 0.0189(13) 0.0019(13) O2 0.0585(19) 0.0345(15) 0.0254(14) 0.0014(13) 0.0246(14) -0.0029(15) C1 0.0201(16) 0.0210(16) 0.0206(17) 0.0013(13) 0.0073(13) -0.0004(13) C2 0.0282(18) 0.0252(18) 0.0192(17) -0.0008(14) 0.0088(15) -0.0037(14) C3 0.0255(17) 0.0304(19) 0.0258(19) -0.0029(15) 0.0169(15) -0.0020(15) C4 0.0214(15) 0.0201(16) 0.0227(17) 0.0001(13) 0.0110(14) -0.0007(13) C5 0.0231(16) 0.0243(17) 0.0185(16) 0.0019(14) 0.0094(13) -0.0003(13) C6 0.0241(16) 0.0177(15) 0.0225(17) -0.0007(13) 0.0122(14) -0.0007(13) C7 0.0289(19) 0.034(2) 0.028(2) -0.0001(16) 0.0166(16) 0.0022(16) C8 0.0311(19) 0.035(2) 0.0190(18) 0.0037(16) 0.0087(15) -0.0014(16) C9 0.0221(16) 0.0274(18) 0.0266(19) 0.0019(15) 0.0124(15) 0.0033(14) C10 0.036(2) 0.031(2) 0.038(2) -0.0042(18) 0.0130(19) 0.0031(18) C11 0.031(2) 0.042(2) 0.050(3) 0.002(2) 0.025(2) 0.0014(19) C12 0.0242(18) 0.049(3) 0.028(2) 0.0012(19) 0.0074(16) 0.0104(17) C13 0.0242(17) 0.034(2) 0.0180(17) -0.0032(15) 0.0095(14) 0.0002(15) C14 0.0260(18) 0.047(2) 0.0235(19) 0.0017(18) 0.0129(16) 0.0079(17) C15 0.0235(19) 0.067(3) 0.025(2) -0.005(2) 0.0110(16) -0.002(2) C16 0.037(2) 0.053(3) 0.031(2) -0.005(2) 0.0177(19) -0.014(2) C17 0.040(2) 0.036(2) 0.034(2) 0.0010(19) 0.0150(19) -0.0019(19) C18 0.0242(18) 0.037(2) 0.027(2) 0.0034(17) 0.0091(16) 0.0029(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se C13 1.914(4) . ? Se C1 1.927(3) . ? O1 C7 1.410(5) . ? O1 H1O 0.8400 . ? O2 C8 1.412(5) . ? O2 H2O 0.8400 . ? C1 C6 1.398(5) . ? C1 C2 1.399(5) . ? C2 C3 1.380(5) . ? C2 C8 1.509(5) . ? C3 C4 1.382(5) . ? C3 H3A 0.9500 . ? C4 C5 1.397(5) . ? C4 C9 1.542(5) . ? C5 C6 1.391(5) . ? C5 H5A 0.9500 . ? C6 C7 1.520(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C11 1.516(6) . ? C9 C12 1.522(6) . ? C9 C10 1.547(6) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C18 1.384(6) . ? C13 C14 1.397(5) . ? C14 C15 1.388(7) . ? C14 H14A 0.9500 . ? C15 C16 1.367(7) . ? C15 H15A 0.9500 . ? C16 C17 1.371(6) . ? C16 H16A 0.9500 . ? C17 C18 1.389(6) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? 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 C13 Se C1 99.64(16) . . ? C7 O1 H1O 109.5 . . ? C8 O2 H2O 109.5 . . ? C6 C1 C2 120.6(3) . . ? C6 C1 Se 119.7(3) . . ? C2 C1 Se 119.7(3) . . ? C3 C2 C1 118.4(3) . . ? C3 C2 C8 118.8(4) . . ? C1 C2 C8 122.7(3) . . ? C2 C3 C4 122.8(4) . . ? C2 C3 H3A 118.6 . . ? C4 C3 H3A 118.6 . . ? C3 C4 C5 117.8(3) . . ? C3 C4 C9 119.6(3) . . ? C5 C4 C9 122.7(3) . . ? C6 C5 C4 121.5(3) . . ? C6 C5 H5A 119.2 . . ? C4 C5 H5A 119.2 . . ? C5 C6 C1 118.8(3) . . ? C5 C6 C7 120.5(3) . . ? C1 C6 C7 120.6(3) . . ? O1 C7 C6 113.8(3) . . ? O1 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? O1 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? O2 C8 C2 109.7(3) . . ? O2 C8 H8A 109.7 . . ? C2 C8 H8A 109.7 . . ? O2 C8 H8B 109.7 . . ? C2 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C11 C9 C12 108.9(4) . . ? C11 C9 C4 109.6(3) . . ? C12 C9 C4 112.4(3) . . ? C11 C9 C10 109.4(4) . . ? C12 C9 C10 107.4(3) . . ? C4 C9 C10 109.0(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 119.9(4) . . ? C18 C13 Se 124.0(3) . . ? C14 C13 Se 116.1(3) . . ? C15 C14 C13 119.1(4) . . ? C15 C14 H14A 120.5 . . ? C13 C14 H14A 120.5 . . ? C16 C15 C14 120.9(4) . . ? C16 C15 H15A 119.6 . . ? C14 C15 H15A 119.6 . . ? C15 C16 C17 120.0(4) . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? C16 C17 C18 120.7(4) . . ? C16 C17 H17A 119.7 . . ? C18 C17 H17A 119.7 . . ? C13 C18 C17 119.5(4) . . ? C13 C18 H18A 120.3 . . ? C17 C18 H18A 120.3 . . ? 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 C13 Se C1 C6 94.9(3) . . . . ? C13 Se C1 C2 -85.6(3) . . . . ? C6 C1 C2 C3 -0.2(6) . . . . ? Se C1 C2 C3 -179.7(3) . . . . ? C6 C1 C2 C8 -179.8(4) . . . . ? Se C1 C2 C8 0.7(5) . . . . ? C1 C2 C3 C4 0.9(6) . . . . ? C8 C2 C3 C4 -179.5(4) . . . . ? C2 C3 C4 C5 -0.8(6) . . . . ? C2 C3 C4 C9 -179.6(4) . . . . ? C3 C4 C5 C6 0.0(5) . . . . ? C9 C4 C5 C6 178.8(3) . . . . ? C4 C5 C6 C1 0.6(5) . . . . ? C4 C5 C6 C7 179.9(3) . . . . ? C2 C1 C6 C5 -0.5(5) . . . . ? Se C1 C6 C5 179.0(3) . . . . ? C2 C1 C6 C7 -179.8(3) . . . . ? Se C1 C6 C7 -0.3(5) . . . . ? C5 C6 C7 O1 4.3(5) . . . . ? C1 C6 C7 O1 -176.3(3) . . . . ? C3 C2 C8 O2 95.0(4) . . . . ? C1 C2 C8 O2 -85.5(5) . . . . ? C3 C4 C9 C11 -61.9(5) . . . . ? C5 C4 C9 C11 119.3(4) . . . . ? C3 C4 C9 C12 176.9(4) . . . . ? C5 C4 C9 C12 -1.9(5) . . . . ? C3 C4 C9 C10 57.9(5) . . . . ? C5 C4 C9 C10 -120.9(4) . . . . ? C1 Se C13 C18 -0.1(4) . . . . ? C1 Se C13 C14 178.9(3) . . . . ? C18 C13 C14 C15 0.4(6) . . . . ? Se C13 C14 C15 -178.6(3) . . . . ? C13 C14 C15 C16 -0.8(6) . . . . ? C14 C15 C16 C17 1.4(7) . . . . ? C15 C16 C17 C18 -1.6(7) . . . . ? C14 C13 C18 C17 -0.6(6) . . . . ? Se C13 C18 C17 178.3(3) . . . . ? C16 C17 C18 C13 1.3(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1O O2 0.84 1.94 2.753(4) 163.4 3_656 O2 H2O O1 0.84 2.00 2.813(4) 161.7 1_556 _diffrn_measured_fraction_theta_max 0.916 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.754 _refine_diff_density_min -0.545 _refine_diff_density_rms 0.105 #===END