# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1635 data_seooph _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H24 O5 Se' _chemical_formula_weight 411.34 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.0174(8) _cell_length_b 20.717(3) _cell_length_c 7.6596(10) _cell_angle_alpha 90.00 _cell_angle_beta 108.215(3) _cell_angle_gamma 90.00 _cell_volume 907.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2914 _cell_measurement_theta_min 2.8 _cell_measurement_theta_max 27.65 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.506 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 2.096 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5756 _exptl_absorpt_correction_T_max 0.6452 _exptl_absorpt_process_details 'Bruker SHELXTL' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ' omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5619 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 28.60 _reflns_number_total 3223 _reflns_number_gt 2792 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT & SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0318P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.017(9) _refine_ls_number_reflns 3210 _refine_ls_number_parameters 298 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0588 _refine_ls_wR_factor_gt 0.0568 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.75936(6) 0.76454(2) 0.75850(4) 0.02942(8) Uani 1 1 d . . . C1 C 0.2444(5) 0.96044(16) 0.7237(4) 0.0228(7) Uani 1 1 d . . . C2 C 0.4873(5) 0.93178(17) 0.8195(4) 0.0217(7) Uani 1 1 d . . . H2 H 0.559(6) 0.9533(18) 0.937(5) 0.033 Uiso 1 1 d . . . C3 C 0.4748(6) 0.85916(15) 0.8458(4) 0.0223(6) Uani 1 1 d . . . H3A H 0.591(6) 0.8422(18) 0.952(5) 0.033 Uiso 1 1 d . . . H3B H 0.331(6) 0.8478(18) 0.856(5) 0.033 Uiso 1 1 d . . . C4 C 0.5178(5) 0.83116(15) 0.6725(4) 0.0210(6) Uani 1 1 d . . . H4 H 0.383(6) 0.8159(17) 0.593(5) 0.031 Uiso 1 1 d . . . C5 C 0.5953(5) 0.88840(15) 0.5781(4) 0.0222(6) Uani 1 1 d . . . H5B H 0.744(6) 0.8805(18) 0.569(4) 0.033 Uiso 1 1 d . . . C6 C 0.4219(5) 0.91003(16) 0.3962(4) 0.0226(6) Uani 1 1 d . . . H6A H 0.493(5) 0.9457(18) 0.343(4) 0.034 Uiso 1 1 d . . . H6B H 0.389(6) 0.8743(18) 0.311(5) 0.034 Uiso 1 1 d . . . C7 C 0.1737(5) 0.93264(14) 0.3937(4) 0.0192(6) Uani 1 1 d . . . C8 C 0.1504(5) 1.00399(15) 0.3431(4) 0.0231(6) Uani 1 1 d . . . H8A H 0.185(6) 1.0095(18) 0.235(5) 0.035 Uiso 1 1 d . . . C9 C 0.2977(6) 1.04597(16) 0.4985(5) 0.0291(7) Uani 1 1 d . . . H9A H 0.453(7) 1.037(2) 0.512(5) 0.044 Uiso 1 1 d . . . H9B H 0.279(6) 1.092(2) 0.461(5) 0.044 Uiso 1 1 d . . . C10 C 0.2390(6) 1.03169(17) 0.6734(5) 0.0285(7) Uani 1 1 d . . . H10A H 0.340(7) 1.052(2) 0.767(5) 0.043 Uiso 1 1 d . . . H10B H 0.071(7) 1.044(2) 0.665(5) 0.043 Uiso 1 1 d . . . O11 O 0.1271(3) 0.92173(10) 0.5667(2) 0.0190(4) Uani 1 1 d . . . O12 O 0.6414(3) 0.94055(10) 0.7110(3) 0.0230(4) Uani 1 1 d . . . C13 C -0.0095(6) 0.89167(17) 0.2560(4) 0.0235(6) Uani 1 1 d . . . H13A H -0.163(7) 0.9046(18) 0.247(4) 0.035 Uiso 1 1 d . . . H13B H 0.000(6) 0.8966(18) 0.138(5) 0.035 Uiso 1 1 d . . . H13C H 0.018(7) 0.847(2) 0.295(5) 0.035 Uiso 1 1 d . . . O14 O -0.0951(4) 1.02265(10) 0.3029(3) 0.0246(5) Uani 1 1 d . . . C15 C -0.1670(6) 1.07262(17) 0.1846(5) 0.0267(8) Uani 1 1 d . . . C16 C -0.4144(7) 1.08937(19) 0.1617(6) 0.0299(8) Uani 1 1 d . . . H16A H -0.475(7) 1.119(2) 0.075(5) 0.045 Uiso 1 1 d . . . H16B H -0.423(7) 1.104(2) 0.263(6) 0.045 Uiso 1 1 d . . . H16C H -0.514(7) 1.054(2) 0.109(5) 0.045 Uiso 1 1 d . . . O17 O -0.0444(5) 1.09885(13) 0.1086(4) 0.0431(7) Uani 1 1 d . . . O18 O 0.1270(4) 0.95013(13) 0.8543(3) 0.0270(6) Uani 1 1 d . . . H18 H 0.018(7) 0.956(2) 0.813(6) 0.040 Uiso 1 1 d . . . C19 C 0.8137(6) 0.73851(15) 0.5367(4) 0.0254(7) Uani 1 1 d . . . C20 C 0.6457(6) 0.74185(16) 0.3642(4) 0.0298(7) Uani 1 1 d . . . H20 H 0.494(6) 0.7557(19) 0.350(4) 0.036 Uiso 1 1 d . . . C21 C 0.6960(7) 0.71973(17) 0.2098(5) 0.0353(8) Uani 1 1 d . . . H21 H 0.581(7) 0.7236(19) 0.100(5) 0.042 Uiso 1 1 d . . . C22 C 0.9126(7) 0.69197(17) 0.2272(5) 0.0382(9) Uani 1 1 d . . . H22 H 0.944(6) 0.676(2) 0.119(5) 0.046 Uiso 1 1 d . . . C23 C 1.0784(7) 0.68832(17) 0.3969(6) 0.0362(8) Uani 1 1 d . . . H23 H 1.218(7) 0.670(2) 0.411(5) 0.043 Uiso 1 1 d . . . C24 C 1.0329(6) 0.71238(16) 0.5526(5) 0.0294(7) Uani 1 1 d . . . H24 H 1.146(7) 0.7113(19) 0.670(5) 0.044 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 Se1 0.03539(16) 0.02981(14) 0.02408(13) 0.00341(16) 0.01078(10) 0.01146(17) C1 0.0174(15) 0.0274(16) 0.0231(16) -0.0042(13) 0.0057(12) -0.0016(13) C2 0.0172(15) 0.0294(18) 0.0179(15) -0.0013(13) 0.0046(12) -0.0009(13) C3 0.0201(15) 0.0249(16) 0.0223(15) 0.0002(12) 0.0074(12) 0.0026(12) C4 0.0196(15) 0.0229(16) 0.0191(14) 0.0004(12) 0.0041(12) 0.0028(12) C5 0.0180(15) 0.0259(17) 0.0234(14) -0.0021(13) 0.0076(12) 0.0008(12) C6 0.0230(16) 0.0239(17) 0.0233(14) 0.0024(13) 0.0105(12) 0.0021(12) C7 0.0176(14) 0.0226(15) 0.0187(13) 0.0035(12) 0.0074(11) 0.0013(12) C8 0.0187(15) 0.0254(17) 0.0261(15) 0.0036(13) 0.0085(12) 0.0001(12) C9 0.0236(17) 0.0223(17) 0.0380(18) 0.0033(14) 0.0049(14) -0.0002(13) C10 0.0295(18) 0.0257(18) 0.0276(16) -0.0051(14) 0.0049(13) 0.0026(14) O11 0.0169(10) 0.0239(11) 0.0173(9) -0.0012(8) 0.0072(8) -0.0009(8) O12 0.0162(10) 0.0235(11) 0.0297(10) -0.0041(9) 0.0076(8) -0.0025(9) C13 0.0211(15) 0.0289(18) 0.0193(14) 0.0008(13) 0.0046(12) -0.0019(13) O14 0.0198(11) 0.0275(12) 0.0263(10) 0.0083(9) 0.0070(8) 0.0039(9) C15 0.030(2) 0.0266(18) 0.0210(16) 0.0038(14) 0.0046(14) 0.0047(14) C16 0.031(2) 0.025(2) 0.0318(19) 0.0037(15) 0.0062(16) 0.0041(15) O17 0.0480(16) 0.0411(16) 0.0473(15) 0.0228(13) 0.0252(14) 0.0085(13) O18 0.0185(12) 0.0435(16) 0.0193(12) -0.0017(11) 0.0065(10) 0.0066(12) C19 0.0361(18) 0.0177(14) 0.0268(15) 0.0000(12) 0.0162(14) -0.0019(13) C20 0.0327(18) 0.0255(17) 0.0327(16) -0.0008(13) 0.0123(14) -0.0019(14) C21 0.052(2) 0.0236(17) 0.0325(18) -0.0027(14) 0.0166(16) -0.0073(15) C22 0.066(3) 0.0194(18) 0.042(2) -0.0034(15) 0.034(2) -0.0017(17) C23 0.041(2) 0.0232(18) 0.053(2) 0.0009(16) 0.0278(18) 0.0026(15) C24 0.0327(19) 0.0216(17) 0.0375(18) 0.0032(15) 0.0162(15) -0.0002(14) _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 C19 1.906(3) . ? Se1 C4 1.963(3) . ? C1 O18 1.410(3) . ? C1 O11 1.434(3) . ? C1 C10 1.524(5) . ? C1 C2 1.535(4) . ? C2 O12 1.437(4) . ? C2 C3 1.523(5) . ? C2 H2 0.97(4) . ? C3 C4 1.543(4) . ? C3 H3A 0.96(4) . ? C3 H3B 0.92(4) . ? C4 C5 1.535(4) . ? C4 H4 0.90(3) . ? C5 O12 1.450(3) . ? C5 C6 1.524(4) . ? C5 H5B 0.93(3) . ? C6 C7 1.560(4) . ? C6 H6A 1.00(4) . ? C6 H6B 0.96(4) . ? C7 O11 1.456(3) . ? C7 C8 1.523(4) . ? C7 C13 1.524(4) . ? C8 O14 1.464(3) . ? C8 C9 1.516(4) . ? C8 H8A 0.92(3) . ? C9 C10 1.517(5) . ? C9 H9A 0.93(4) . ? C9 H9B 0.99(4) . ? C10 H10A 0.89(4) . ? C10 H10B 1.02(4) . ? C13 H13A 0.94(4) . ? C13 H13B 0.93(3) . ? C13 H13C 0.97(4) . ? O14 C15 1.354(4) . ? C15 O17 1.203(4) . ? C15 C16 1.485(5) . ? C16 H16A 0.90(4) . ? C16 H16B 0.85(4) . ? C16 H16C 0.94(4) . ? O18 H18 0.64(4) . ? C19 C20 1.392(4) . ? C19 C24 1.395(4) . ? C20 C21 1.387(5) . ? C20 H20 0.93(3) . ? C21 C22 1.392(5) . ? C21 H21 0.91(4) . ? C22 C23 1.371(5) . ? C22 H22 0.97(4) . ? C23 C24 1.397(5) . ? C23 H23 0.90(4) . ? C24 H24 0.94(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19 Se1 C4 102.43(12) . . ? O18 C1 O11 106.6(2) . . ? O18 C1 C10 110.5(3) . . ? O11 C1 C10 111.3(2) . . ? O18 C1 C2 102.5(2) . . ? O11 C1 C2 109.3(2) . . ? C10 C1 C2 116.0(3) . . ? O12 C2 C3 105.6(3) . . ? O12 C2 C1 111.4(2) . . ? C3 C2 C1 111.5(3) . . ? O12 C2 H2 107(2) . . ? C3 C2 H2 111(2) . . ? C1 C2 H2 110(2) . . ? C2 C3 C4 103.3(2) . . ? C2 C3 H3A 115(2) . . ? C4 C3 H3A 108(2) . . ? C2 C3 H3B 110(2) . . ? C4 C3 H3B 113(2) . . ? H3A C3 H3B 107(3) . . ? C5 C4 C3 105.8(2) . . ? C5 C4 Se1 113.5(2) . . ? C3 C4 Se1 106.33(19) . . ? C5 C4 H4 107(2) . . ? C3 C4 H4 111(2) . . ? Se1 C4 H4 113(2) . . ? O12 C5 C6 110.4(2) . . ? O12 C5 C4 105.4(2) . . ? C6 C5 C4 115.8(2) . . ? O12 C5 H5B 102(2) . . ? C6 C5 H5B 112(2) . . ? C4 C5 H5B 110(2) . . ? C5 C6 C7 118.6(2) . . ? C5 C6 H6A 109.4(19) . . ? C7 C6 H6A 107.7(19) . . ? C5 C6 H6B 109(2) . . ? C7 C6 H6B 103(2) . . ? H6A C6 H6B 108(3) . . ? O11 C7 C8 110.7(2) . . ? O11 C7 C13 103.9(2) . . ? C8 C7 C13 112.0(2) . . ? O11 C7 C6 113.5(2) . . ? C8 C7 C6 107.8(2) . . ? C13 C7 C6 108.9(2) . . ? O14 C8 C9 108.5(2) . . ? O14 C8 C7 108.4(2) . . ? C9 C8 C7 111.8(3) . . ? O14 C8 H8A 106(2) . . ? C9 C8 H8A 113(2) . . ? C7 C8 H8A 109(2) . . ? C8 C9 C10 109.9(3) . . ? C8 C9 H9A 107(2) . . ? C10 C9 H9A 112(2) . . ? C8 C9 H9B 110(2) . . ? C10 C9 H9B 114(2) . . ? H9A C9 H9B 104(3) . . ? C9 C10 C1 114.8(3) . . ? C9 C10 H10A 110(3) . . ? C1 C10 H10A 107(3) . . ? C9 C10 H10B 113(2) . . ? C1 C10 H10B 102(2) . . ? H10A C10 H10B 110(3) . . ? C1 O11 C7 119.5(2) . . ? C2 O12 C5 107.2(2) . . ? C7 C13 H13A 112(2) . . ? C7 C13 H13B 111(2) . . ? H13A C13 H13B 105(3) . . ? C7 C13 H13C 107(2) . . ? H13A C13 H13C 111(3) . . ? H13B C13 H13C 111(3) . . ? C15 O14 C8 115.6(2) . . ? O17 C15 O14 123.6(3) . . ? O17 C15 C16 125.5(3) . . ? O14 C15 C16 110.9(3) . . ? C15 C16 H16A 114(3) . . ? C15 C16 H16B 109(3) . . ? H16A C16 H16B 108(4) . . ? C15 C16 H16C 110(2) . . ? H16A C16 H16C 99(3) . . ? H16B C16 H16C 117(4) . . ? C1 O18 H18 106(4) . . ? C20 C19 C24 119.2(3) . . ? C20 C19 Se1 123.8(2) . . ? C24 C19 Se1 116.9(2) . . ? C21 C20 C19 120.4(3) . . ? C21 C20 H20 117.8(19) . . ? C19 C20 H20 121.6(19) . . ? C20 C21 C22 120.1(3) . . ? C20 C21 H21 117(2) . . ? C22 C21 H21 123(2) . . ? C23 C22 C21 119.7(3) . . ? C23 C22 H22 121(2) . . ? C21 C22 H22 119(2) . . ? C22 C23 C24 120.7(3) . . ? C22 C23 H23 121(2) . . ? C24 C23 H23 118(3) . . ? C19 C24 C23 119.7(3) . . ? C19 C24 H24 118(2) . . ? C23 C24 H24 122(2) . . ? 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 O18 C1 C2 O12 -177.0(2) . . . . ? O11 C1 C2 O12 70.2(3) . . . . ? C10 C1 C2 O12 -56.5(3) . . . . ? O18 C1 C2 C3 65.4(3) . . . . ? O11 C1 C2 C3 -47.4(3) . . . . ? C10 C1 C2 C3 -174.2(3) . . . . ? O12 C2 C3 C4 -28.5(3) . . . . ? C1 C2 C3 C4 92.6(3) . . . . ? C2 C3 C4 C5 10.0(3) . . . . ? C2 C3 C4 Se1 131.0(2) . . . . ? C19 Se1 C4 C5 -59.9(2) . . . . ? C19 Se1 C4 C3 -175.8(2) . . . . ? C3 C4 C5 O12 11.6(3) . . . . ? Se1 C4 C5 O12 -104.6(2) . . . . ? C3 C4 C5 C6 -110.8(3) . . . . ? Se1 C4 C5 C6 133.0(2) . . . . ? O12 C5 C6 C7 -60.1(3) . . . . ? C4 C5 C6 C7 59.5(4) . . . . ? C5 C6 C7 O11 -8.0(4) . . . . ? C5 C6 C7 C8 115.0(3) . . . . ? C5 C6 C7 C13 -123.2(3) . . . . ? O11 C7 C8 O14 -66.9(3) . . . . ? C13 C7 C8 O14 48.6(3) . . . . ? C6 C7 C8 O14 168.4(2) . . . . ? O11 C7 C8 C9 52.7(3) . . . . ? C13 C7 C8 C9 168.2(3) . . . . ? C6 C7 C8 C9 -71.9(3) . . . . ? O14 C8 C9 C10 65.5(3) . . . . ? C7 C8 C9 C10 -54.1(3) . . . . ? C8 C9 C10 C1 50.8(4) . . . . ? O18 C1 C10 C9 -163.6(3) . . . . ? O11 C1 C10 C9 -45.4(4) . . . . ? C2 C1 C10 C9 80.4(4) . . . . ? O18 C1 O11 C7 166.4(2) . . . . ? C10 C1 O11 C7 45.9(3) . . . . ? C2 C1 O11 C7 -83.5(3) . . . . ? C8 C7 O11 C1 -50.2(3) . . . . ? C13 C7 O11 C1 -170.6(2) . . . . ? C6 C7 O11 C1 71.2(3) . . . . ? C3 C2 O12 C5 37.6(3) . . . . ? C1 C2 O12 C5 -83.6(3) . . . . ? C6 C5 O12 C2 95.3(3) . . . . ? C4 C5 O12 C2 -30.5(3) . . . . ? C9 C8 O14 C15 85.6(3) . . . . ? C7 C8 O14 C15 -152.7(3) . . . . ? C8 O14 C15 O17 3.5(5) . . . . ? C8 O14 C15 C16 -177.1(3) . . . . ? C4 Se1 C19 C20 -28.2(3) . . . . ? C4 Se1 C19 C24 154.4(2) . . . . ? C24 C19 C20 C21 -0.3(5) . . . . ? Se1 C19 C20 C21 -177.6(2) . . . . ? C19 C20 C21 C22 2.2(5) . . . . ? C20 C21 C22 C23 -1.9(5) . . . . ? C21 C22 C23 C24 -0.3(5) . . . . ? C20 C19 C24 C23 -1.8(5) . . . . ? Se1 C19 C24 C23 175.7(3) . . . . ? C22 C23 C24 C19 2.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 28.60 _diffrn_measured_fraction_theta_full 0.902 _refine_diff_density_max 0.370 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.054 data_PHSECL _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H23 Cl O4 Se' _chemical_formula_sum 'C19 H23 Cl O4 Se' _chemical_formula_weight 429.78 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.2491(2) _cell_length_b 21.3577(10) _cell_length_c 16.4109(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.709(3) _cell_angle_gamma 90.00 _cell_volume 1839.66(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12766 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 26.0 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 2.207 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.916 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius kappaCCD area detector' _diffrn_measurement_method 'phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 12734 _diffrn_reflns_av_R_equivalents 0.101 _diffrn_reflns_av_sigmaI/netI 0.158 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6208 _reflns_number_gt 4081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (????, 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC version 5.1 (Bruker, 1997)' _computing_publication_material 'SHELXl-97; PLATON (Spek, 1999)' _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^)+(0.0233P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens 'methyl H atoms from delta-F, other placed geometrically' _refine_ls_hydrogen_treatment 'methyl H atoms as part of rigid rotating group, others riding' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0027(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.000(12) _refine_ls_number_reflns 6208 _refine_ls_number_parameters 454 _refine_ls_number_restraints 39 _refine_ls_R_factor_all 0.116 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.103 _refine_ls_wR_factor_gt 0.0894 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.970 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se Se -0.29915(13) 0.32889(5) 0.06235(5) 0.0323(2) Uani 1 1 d . . . Cl Cl 0.2086(4) 0.49252(11) 0.26816(14) 0.0460(6) Uani 1 1 d . . . O O 0.2999(8) 0.4488(2) 0.0022(3) 0.0250(13) Uani 1 1 d . . . C1 C 0.1032(12) 0.4012(4) -0.0056(5) 0.0264(19) Uani 1 1 d . . . H1A H 0.1842 0.3589 -0.0072 0.032 Uiso 1 1 calc R . . C2 C -0.0777(12) 0.4046(3) 0.0656(5) 0.0233(18) Uani 1 1 d . . . H2A H -0.1915 0.4414 0.0553 0.028 Uiso 1 1 calc R . . C3 C 0.0418(15) 0.4142(4) 0.1491(5) 0.033(2) Uani 1 1 d . . . H3A H 0.1596 0.3789 0.1601 0.039 Uiso 1 1 calc R . . H3B H -0.0948 0.4121 0.1901 0.039 Uiso 1 1 calc R . . C4 C 0.1881(15) 0.4752(4) 0.1617(5) 0.031(2) Uani 1 1 d . . . H4A H 0.3637 0.4705 0.1395 0.037 Uiso 1 1 calc R . . C5 C 0.0541(14) 0.5304(3) 0.1194(5) 0.0267(19) Uani 1 1 d . . . O5 O -0.1717(10) 0.5412(3) 0.1335(4) 0.0388(15) Uani 1 1 d . . . C6 C 0.1946(14) 0.5698(4) 0.0577(5) 0.0300(19) Uani 1 1 d . . . H6A H 0.3806 0.5644 0.0655 0.036 Uiso 1 1 calc R . . H6B H 0.1537 0.6146 0.0661 0.036 Uiso 1 1 calc R . . C7 C 0.1190(13) 0.5507(3) -0.0290(5) 0.0257(19) Uani 1 1 d . . . H7A H -0.0640 0.5395 -0.0303 0.031 Uiso 1 1 calc R . . H7B H 0.1431 0.5869 -0.0658 0.031 Uiso 1 1 calc R . . C8 C 0.2698(13) 0.4967(3) -0.0596(4) 0.0221(17) Uani 1 1 d . . . H8A H 0.4423 0.5121 -0.0753 0.027 Uiso 1 1 calc R . . C9 C 0.1552(12) 0.4580(3) -0.1315(5) 0.0238(18) Uani 1 1 d . . . C10 C -0.0280(13) 0.4152(4) -0.0893(5) 0.0293(19) Uani 1 1 d . . . H10A H -0.0543 0.3762 -0.1209 0.035 Uiso 1 1 calc R . . H10B H -0.1946 0.4360 -0.0818 0.035 Uiso 1 1 calc R . . C11 C 0.3493(13) 0.4220(4) -0.1797(5) 0.032(2) Uani 1 1 d . . . H11A H 0.2630 0.3991 -0.2239 0.048 Uiso 1 1 calc R . . H11B H 0.4381 0.3923 -0.1438 0.048 Uiso 1 1 calc R . . H11C H 0.4729 0.4512 -0.2029 0.048 Uiso 1 1 calc R . . C12 C 0.1121(13) 0.5443(3) -0.2270(5) 0.0235(18) Uani 1 1 d . . . C13 C -0.0645(13) 0.5718(4) -0.2884(5) 0.0286(19) Uani 1 1 d . . . H13A H 0.0034 0.6120 -0.3071 0.043 Uiso 1 1 calc R . . H13B H -0.2317 0.5784 -0.2639 0.043 Uiso 1 1 calc R . . H13C H -0.0820 0.5433 -0.3349 0.043 Uiso 1 1 calc R . . O13 O 0.3246(8) 0.5616(2) -0.2133(3) 0.0300(13) Uani 1 1 d . . . C1P C -0.0438(11) 0.2664(3) 0.0854(4) 0.0270(17) Uani 1 1 d D . . C2P C 0.0734(11) 0.2342(3) 0.0240(4) 0.032(2) Uani 1 1 d D . . H2P H 0.0233 0.2414 -0.0310 0.038 Uiso 1 1 calc R . . C3P C 0.2644(11) 0.1911(3) 0.0415(5) 0.039(2) Uani 1 1 d D . . H3P H 0.3443 0.1689 -0.0013 0.047 Uiso 1 1 calc R . . C4P C 0.3376(13) 0.1808(3) 0.1212(5) 0.042(2) Uani 1 1 d D . . H4P H 0.4691 0.1516 0.1333 0.051 Uiso 1 1 calc R . . C5P C 0.2203(13) 0.2127(3) 0.1834(5) 0.041(2) Uani 1 1 d D . . H5P H 0.2700 0.2054 0.2385 0.049 Uiso 1 1 calc R . . C6P C 0.0298(12) 0.2555(3) 0.1653(4) 0.036(2) Uani 1 1 d D . . H6P H -0.0510 0.2776 0.2081 0.044 Uiso 1 1 calc R . . Se' Se 1.01692(12) 0.26738(5) 0.65213(5) 0.0263(2) Uani 1 1 d . . . Cl' Cl 0.5240(4) 0.16402(11) 0.38712(14) 0.0394(5) Uani 1 1 d . . . O' O 0.4330(8) 0.3505(2) 0.5138(3) 0.0210(12) Uani 1 1 d . . . C1' C 0.6207(12) 0.3418(3) 0.5784(5) 0.0210(18) Uani 1 1 d . . . H1'A H 0.5319 0.3310 0.6301 0.025 Uiso 1 1 calc R . . C2' C 0.8002(12) 0.2885(3) 0.5555(4) 0.0220(18) Uani 1 1 d . . . H2'A H 0.9167 0.3052 0.5130 0.026 Uiso 1 1 calc R . . C3' C 0.6769(13) 0.2298(4) 0.5201(5) 0.029(2) Uani 1 1 d . . . H3'A H 0.5497 0.2140 0.5591 0.034 Uiso 1 1 calc R . . H3'B H 0.8093 0.1972 0.5142 0.034 Uiso 1 1 calc R . . C4' C 0.5439(13) 0.2401(3) 0.4365(5) 0.0267(19) Uani 1 1 d . . . H4'A H 0.3691 0.2575 0.4444 0.032 Uiso 1 1 calc R . . C5' C 0.6936(14) 0.2822(4) 0.3811(4) 0.027(2) Uani 1 1 d . . . O5' O 0.9159(8) 0.2713(3) 0.3661(3) 0.0352(13) Uani 1 1 d . . . C6' C 0.5703(13) 0.3413(3) 0.3480(4) 0.0264(19) Uani 1 1 d . . . H6'A H 0.3828 0.3366 0.3490 0.032 Uiso 1 1 calc R . . H6'B H 0.6211 0.3474 0.2906 0.032 Uiso 1 1 calc R . . C7' C 0.6482(14) 0.3996(4) 0.3982(5) 0.029(2) Uani 1 1 d . . . H7'A H 0.8269 0.3949 0.4172 0.034 Uiso 1 1 calc R . . H7'B H 0.6383 0.4372 0.3630 0.034 Uiso 1 1 calc R . . C8' C 0.4744(12) 0.4086(3) 0.4723(5) 0.0216(18) Uani 1 1 d . . . H8'A H 0.3069 0.4261 0.4536 0.026 Uiso 1 1 calc R . . C9' C 0.5869(13) 0.4506(4) 0.5404(5) 0.0230(18) Uani 1 1 d . . . C10' C 0.7521(13) 0.4045(3) 0.5883(4) 0.0228(18) Uani 1 1 d . . . H10C H 0.9265 0.4029 0.5661 0.027 Uiso 1 1 calc R . . H10D H 0.7627 0.4165 0.6465 0.027 Uiso 1 1 calc R . . C11' C 0.3800(13) 0.4794(4) 0.5934(5) 0.0271(19) Uani 1 1 d . . . H11D H 0.4596 0.5052 0.6361 0.041 Uiso 1 1 calc R . . H11E H 0.2803 0.4460 0.6186 0.041 Uiso 1 1 calc R . . H11F H 0.2676 0.5056 0.5596 0.041 Uiso 1 1 calc R . . C12' C 0.6583(14) 0.5438(3) 0.4600(5) 0.0238(19) Uani 1 1 d . . . O12 O -0.0014(8) 0.4961(2) -0.1872(3) 0.0245(12) Uani 1 1 d . . . O12' O 0.7536(8) 0.5003(2) 0.5113(3) 0.0230(12) Uani 1 1 d . . . C13' C 0.8505(14) 0.5928(4) 0.4435(6) 0.041(2) Uani 1 1 d . . . H13D H 0.7898 0.6196 0.3987 0.062 Uiso 1 1 calc R . . H13E H 1.0115 0.5731 0.4282 0.062 Uiso 1 1 calc R . . H13F H 0.8773 0.6183 0.4925 0.062 Uiso 1 1 calc R . . O13' O 0.4441(9) 0.5424(2) 0.4331(3) 0.0288(14) Uani 1 1 d . . . C1P' C 0.7568(12) 0.2324(3) 0.7211(4) 0.0237(18) Uani 1 1 d D . . C2P' C 0.6832(12) 0.1706(3) 0.7125(4) 0.031(2) Uani 1 1 d D . . H2P' H 0.7630 0.1445 0.6735 0.037 Uiso 1 1 calc R . . C3P' C 0.4911(13) 0.1469(4) 0.7615(4) 0.033(2) Uani 1 1 d D . . H3P' H 0.4387 0.1046 0.7557 0.039 Uiso 1 1 calc R . . C4P' C 0.3772(14) 0.1847(3) 0.8182(5) 0.031(2) Uani 1 1 d D . . H4P' H 0.2434 0.1686 0.8506 0.037 Uiso 1 1 calc R . . C5P' C 0.4557(13) 0.2458(4) 0.8285(5) 0.044(3) Uani 1 1 d D . . H5P' H 0.3798 0.2713 0.8689 0.052 Uiso 1 1 calc R . . C6P' C 0.6456(12) 0.2697(4) 0.7798(4) 0.0310(17) Uani 1 1 d D . . H6P' H 0.6999 0.3118 0.7867 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 0.0192(4) 0.0316(5) 0.0460(6) -0.0001(5) 0.0017(3) -0.0018(4) Cl 0.0605(14) 0.0459(15) 0.0314(14) -0.0013(12) -0.0055(11) -0.0053(11) O 0.020(3) 0.019(3) 0.035(4) 0.005(3) -0.006(2) -0.002(2) C1 0.016(4) 0.028(5) 0.035(5) -0.001(4) -0.008(3) -0.006(3) C2 0.017(4) 0.021(4) 0.032(5) 0.004(4) 0.004(3) -0.005(3) C3 0.032(4) 0.031(5) 0.035(6) -0.009(5) 0.001(4) 0.002(4) C4 0.032(4) 0.030(5) 0.029(5) -0.001(4) 0.004(4) 0.000(3) C5 0.035(5) 0.023(5) 0.022(5) -0.015(4) -0.003(4) 0.002(3) O5 0.033(3) 0.037(4) 0.047(4) 0.000(3) 0.007(3) 0.003(3) C6 0.023(4) 0.025(4) 0.042(6) 0.006(4) -0.006(3) -0.001(3) C7 0.022(4) 0.024(5) 0.031(5) -0.001(4) 0.001(3) -0.005(3) C8 0.023(4) 0.017(4) 0.026(5) 0.005(4) -0.002(3) -0.001(3) C9 0.018(4) 0.029(5) 0.025(5) -0.002(4) -0.002(3) -0.001(3) C10 0.026(4) 0.029(5) 0.033(5) -0.005(4) -0.004(3) -0.006(3) C11 0.028(4) 0.042(5) 0.025(5) -0.007(4) -0.005(4) 0.000(4) C12 0.023(4) 0.025(5) 0.023(5) -0.009(4) 0.001(3) -0.007(3) C13 0.022(4) 0.031(5) 0.033(5) -0.001(4) -0.004(3) -0.001(3) O13 0.019(3) 0.037(3) 0.034(4) -0.004(3) -0.003(2) -0.001(2) C1P 0.024(4) 0.015(4) 0.042(5) 0.003(5) 0.004(3) -0.005(4) C2P 0.034(5) 0.028(5) 0.032(5) 0.008(4) -0.006(4) -0.004(4) C3P 0.038(5) 0.032(5) 0.048(7) 0.001(5) 0.006(4) 0.007(4) C4P 0.037(5) 0.026(5) 0.064(7) 0.008(5) -0.007(5) 0.004(4) C5P 0.053(6) 0.036(6) 0.032(6) 0.002(5) -0.005(4) 0.002(4) C6P 0.042(5) 0.038(6) 0.029(6) 0.009(5) 0.007(4) -0.003(4) Se' 0.0169(4) 0.0326(5) 0.0292(5) 0.0017(5) -0.0012(3) -0.0001(4) Cl' 0.0463(12) 0.0305(12) 0.0413(15) -0.0085(11) -0.0071(10) -0.0010(10) O' 0.017(2) 0.021(3) 0.025(3) 0.000(2) -0.009(2) 0.0005(19) C1' 0.025(4) 0.016(5) 0.021(5) 0.002(4) -0.005(3) -0.002(3) C2' 0.022(4) 0.027(5) 0.018(4) 0.005(3) 0.002(3) 0.004(3) C3' 0.023(4) 0.034(5) 0.029(5) 0.001(4) 0.006(3) -0.004(3) C4' 0.019(4) 0.027(4) 0.035(5) -0.005(4) 0.000(3) 0.008(3) C5' 0.032(5) 0.032(5) 0.016(4) -0.005(4) -0.001(3) 0.001(3) O5' 0.026(3) 0.046(3) 0.034(3) -0.004(3) 0.008(2) 0.013(3) C6' 0.027(4) 0.030(5) 0.023(5) 0.011(4) 0.001(3) 0.005(3) C7' 0.023(4) 0.030(5) 0.033(5) 0.000(4) 0.003(4) 0.000(3) C8' 0.016(4) 0.019(4) 0.030(5) 0.007(4) -0.001(3) 0.006(3) C9' 0.017(4) 0.028(5) 0.024(5) 0.001(4) -0.002(3) -0.006(3) C10' 0.027(4) 0.027(5) 0.015(5) -0.007(4) -0.005(3) -0.001(3) C11' 0.019(4) 0.031(5) 0.031(5) 0.008(4) 0.002(3) -0.001(3) C12' 0.025(4) 0.023(5) 0.024(5) -0.001(4) 0.009(4) 0.003(3) O12 0.017(3) 0.026(3) 0.031(3) -0.003(3) -0.006(2) -0.002(2) O12' 0.009(2) 0.025(3) 0.035(3) 0.007(3) 0.000(2) -0.008(2) C13' 0.027(5) 0.031(5) 0.065(7) 0.015(5) 0.003(4) 0.004(3) O13' 0.020(3) 0.032(3) 0.034(4) 0.006(3) -0.001(2) 0.006(2) C1P' 0.028(4) 0.023(5) 0.020(5) 0.005(4) -0.002(3) 0.002(3) C2P' 0.023(4) 0.035(5) 0.034(5) 0.004(4) 0.003(4) 0.003(4) C3P' 0.031(5) 0.043(6) 0.025(5) 0.004(4) -0.001(4) -0.001(4) C4P' 0.030(5) 0.032(5) 0.031(6) 0.007(4) 0.005(4) -0.003(4) C5P' 0.028(5) 0.056(7) 0.047(7) 0.000(5) 0.009(4) 0.012(4) C6P' 0.033(4) 0.026(4) 0.034(5) -0.003(5) -0.001(3) 0.000(4) _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 C1P 1.926(7) . ? Se C2 1.992(7) . ? Cl C4 1.788(8) . ? O C8 1.447(8) . ? O C1 1.453(8) . ? C1 C2 1.516(10) . ? C1 C10 1.559(10) . ? C2 C3 1.514(11) . ? C3 C4 1.524(10) . ? C4 C5 1.535(11) . ? C5 O5 1.232(8) . ? C5 C6 1.516(10) . ? C6 C7 1.527(10) . ? C7 C8 1.488(9) . ? C8 C9 1.556(10) . ? C9 O12 1.469(9) . ? C9 C10 1.501(10) . ? C9 C11 1.509(10) . ? C12 O13 1.193(8) . ? C12 O12 1.360(8) . ? C12 C13 1.483(10) . ? C1P C2P 1.372(7) . ? C1P C6P 1.382(7) . ? C2P C3P 1.388(7) . ? C3P C4P 1.376(7) . ? C4P C5P 1.380(7) . ? C5P C6P 1.385(7) . ? Se' C1P' 1.935(7) . ? Se' C2' 1.991(7) . ? Cl' C4' 1.818(7) . ? O' C8' 1.433(8) . ? O' C1' 1.450(8) . ? C1' C10' 1.513(9) . ? C1' C2' 1.529(9) . ? C2' C3' 1.522(10) . ? C3' C4' 1.548(11) . ? C4' C5' 1.506(10) . ? C5' O5' 1.218(8) . ? C5' C6' 1.517(10) . ? C6' C7' 1.544(10) . ? C7' C8' 1.542(10) . ? C8' C9' 1.544(10) . ? C9' O12' 1.460(8) . ? C9' C10' 1.525(10) . ? C9' C11' 1.530(10) . ? C12' O13' 1.203(8) . ? C12' O12' 1.346(9) . ? C12' C13' 1.482(10) . ? C1P' C2P' 1.382(7) . ? C1P' C6P' 1.384(7) . ? C2P' C3P' 1.392(7) . ? C3P' C4P' 1.375(7) . ? C4P' C5P' 1.377(7) . ? C5P' C6P' 1.383(7) . ? 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 C1P Se C2 98.8(3) . . ? C8 O C1 111.2(5) . . ? O C1 C2 110.5(6) . . ? O C1 C10 104.4(6) . . ? C2 C1 C10 113.3(6) . . ? C3 C2 C1 116.6(6) . . ? C3 C2 Se 111.6(5) . . ? C1 C2 Se 108.2(5) . . ? C2 C3 C4 116.1(7) . . ? C3 C4 C5 111.6(6) . . ? C3 C4 Cl 109.5(6) . . ? C5 C4 Cl 107.7(5) . . ? O5 C5 C6 119.9(7) . . ? O5 C5 C4 119.7(7) . . ? C6 C5 C4 120.3(6) . . ? C5 C6 C7 110.5(6) . . ? C8 C7 C6 112.8(6) . . ? O C8 C7 111.4(6) . . ? O C8 C9 101.1(5) . . ? C7 C8 C9 117.7(6) . . ? O12 C9 C10 105.5(5) . . ? O12 C9 C11 109.4(6) . . ? C10 C9 C11 111.9(6) . . ? O12 C9 C8 112.7(6) . . ? C10 C9 C8 102.6(6) . . ? C11 C9 C8 114.3(6) . . ? C9 C10 C1 104.1(5) . . ? O13 C12 O12 123.9(7) . . ? O13 C12 C13 125.5(7) . . ? O12 C12 C13 110.6(6) . . ? C2P C1P C6P 119.3(6) . . ? C2P C1P Se 121.4(5) . . ? C6P C1P Se 119.2(5) . . ? C1P C2P C3P 120.6(7) . . ? C4P C3P C2P 119.7(7) . . ? C3P C4P C5P 120.2(7) . . ? C4P C5P C6P 119.6(7) . . ? C1P C6P C5P 120.5(7) . . ? C1P' Se' C2' 98.8(3) . . ? C8' O' C1' 110.6(5) . . ? O' C1' C10' 105.7(5) . . ? O' C1' C2' 109.3(5) . . ? C10' C1' C2' 113.8(6) . . ? C3' C2' C1' 116.5(5) . . ? C3' C2' Se' 110.7(5) . . ? C1' C2' Se' 108.7(5) . . ? C2' C3' C4' 114.0(6) . . ? C5' C4' C3' 112.8(6) . . ? C5' C4' Cl' 107.0(5) . . ? C3' C4' Cl' 107.0(5) . . ? O5' C5' C4' 121.1(7) . . ? O5' C5' C6' 119.5(7) . . ? C4' C5' C6' 119.3(6) . . ? C5' C6' C7' 111.8(6) . . ? C8' C7' C6' 111.5(6) . . ? O' C8' C7' 111.2(6) . . ? O' C8' C9' 102.6(6) . . ? C7' C8' C9' 114.7(6) . . ? O12' C9' C10' 107.4(5) . . ? O12' C9' C11' 109.0(6) . . ? C10' C9' C11' 111.7(6) . . ? O12' C9' C8' 114.3(6) . . ? C10' C9' C8' 102.0(6) . . ? C11' C9' C8' 112.2(6) . . ? C1' C10' C9' 105.1(6) . . ? O13' C12' O12' 123.4(7) . . ? O13' C12' C13' 125.8(7) . . ? O12' C12' C13' 110.7(6) . . ? C12 O12 C9 118.2(5) . . ? C12' O12' C9' 119.1(5) . . ? C2P' C1P' C6P' 120.0(6) . . ? C2P' C1P' Se' 120.5(5) . . ? C6P' C1P' Se' 119.5(5) . . ? C1P' C2P' C3P' 119.4(6) . . ? C4P' C3P' C2P' 120.2(7) . . ? C3P' C4P' C5P' 120.5(7) . . ? C4P' C5P' C6P' 119.7(7) . . ? C5P' C6P' C1P' 120.2(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 O C1 C2 -111.1(6) . . . . ? C8 O C1 C10 11.0(7) . . . . ? O C1 C2 C3 -42.6(9) . . . . ? C10 C1 C2 C3 -159.4(6) . . . . ? O C1 C2 Se -169.4(4) . . . . ? C10 C1 C2 Se 73.9(7) . . . . ? C1P Se C2 C3 -62.8(5) . . . . ? C1P Se C2 C1 66.7(5) . . . . ? C1 C2 C3 C4 62.5(9) . . . . ? Se C2 C3 C4 -172.5(5) . . . . ? C2 C3 C4 C5 38.9(9) . . . . ? C2 C3 C4 Cl 158.0(5) . . . . ? C3 C4 C5 O5 53.5(9) . . . . ? Cl C4 C5 O5 -66.7(8) . . . . ? C3 C4 C5 C6 -123.8(8) . . . . ? Cl C4 C5 C6 116.0(6) . . . . ? O5 C5 C6 C7 -76.5(9) . . . . ? C4 C5 C6 C7 100.7(7) . . . . ? C5 C6 C7 C8 -85.0(7) . . . . ? C1 O C8 C7 93.9(7) . . . . ? C1 O C8 C9 -32.0(6) . . . . ? C6 C7 C8 O 42.8(8) . . . . ? C6 C7 C8 C9 159.0(6) . . . . ? O C8 C9 O12 153.3(5) . . . . ? C7 C8 C9 O12 31.8(8) . . . . ? O C8 C9 C10 40.4(6) . . . . ? C7 C8 C9 C10 -81.2(7) . . . . ? O C8 C9 C11 -80.9(7) . . . . ? C7 C8 C9 C11 157.5(7) . . . . ? O12 C9 C10 C1 -152.4(6) . . . . ? C11 C9 C10 C1 88.7(7) . . . . ? C8 C9 C10 C1 -34.2(7) . . . . ? O C1 C10 C9 15.7(7) . . . . ? C2 C1 C10 C9 136.0(6) . . . . ? C2 Se C1P C2P -95.5(4) . . . . ? C2 Se C1P C6P 82.0(4) . . . . ? C6P C1P C2P C3P -0.2(2) . . . . ? Se C1P C2P C3P 177.4(4) . . . . ? C1P C2P C3P C4P -0.2(2) . . . . ? C2P C3P C4P C5P 0.5(4) . . . . ? C3P C4P C5P C6P -0.4(6) . . . . ? C2P C1P C6P C5P 0.2(4) . . . . ? Se C1P C6P C5P -177.4(4) . . . . ? C4P C5P C6P C1P 0.1(6) . . . . ? C8' O' C1' C10' 12.0(7) . . . . ? C8' O' C1' C2' -110.9(6) . . . . ? O' C1' C2' C3' -44.4(8) . . . . ? C10' C1' C2' C3' -162.3(6) . . . . ? O' C1' C2' Se' -170.3(4) . . . . ? C10' C1' C2' Se' 71.8(7) . . . . ? C1P' Se' C2' C3' -61.0(5) . . . . ? C1P' Se' C2' C1' 68.2(5) . . . . ? C1' C2' C3' C4' 65.3(8) . . . . ? Se' C2' C3' C4' -169.8(5) . . . . ? C2' C3' C4' C5' 40.5(9) . . . . ? C2' C3' C4' Cl' 157.8(5) . . . . ? C3' C4' C5' O5' 53.5(9) . . . . ? Cl' C4' C5' O5' -63.8(8) . . . . ? C3' C4' C5' C6' -122.4(7) . . . . ? Cl' C4' C5' C6' 120.3(6) . . . . ? O5' C5' C6' C7' -77.9(8) . . . . ? C4' C5' C6' C7' 98.1(8) . . . . ? C5' C6' C7' C8' -86.0(7) . . . . ? C1' O' C8' C7' 92.0(7) . . . . ? C1' O' C8' C9' -31.1(6) . . . . ? C6' C7' C8' O' 44.7(8) . . . . ? C6' C7' C8' C9' 160.5(6) . . . . ? O' C8' C9' O12' 152.7(5) . . . . ? C7' C8' C9' O12' 32.0(8) . . . . ? O' C8' C9' C10' 37.1(6) . . . . ? C7' C8' C9' C10' -83.6(7) . . . . ? O' C8' C9' C11' -82.5(7) . . . . ? C7' C8' C9' C11' 156.8(6) . . . . ? O' C1' C10' C9' 12.7(7) . . . . ? C2' C1' C10' C9' 132.7(6) . . . . ? O12' C9' C10' C1' -150.8(6) . . . . ? C11' C9' C10' C1' 89.7(7) . . . . ? C8' C9' C10' C1' -30.3(7) . . . . ? O13 C12 O12 C9 -8.0(10) . . . . ? C13 C12 O12 C9 172.4(6) . . . . ? C10 C9 O12 C12 172.6(6) . . . . ? C11 C9 O12 C12 -66.9(8) . . . . ? C8 C9 O12 C12 61.5(8) . . . . ? O13' C12' O12' C9' -3.8(10) . . . . ? C13' C12' O12' C9' 175.1(6) . . . . ? C10' C9' O12' C12' 173.2(6) . . . . ? C11' C9' O12' C12' -65.7(8) . . . . ? C8' C9' O12' C12' 60.8(8) . . . . ? C2' Se' C1P' C2P' 83.3(6) . . . . ? C2' Se' C1P' C6P' -97.2(6) . . . . ? C6P' C1P' C2P' C3P' 2.1(11) . . . . ? Se' C1P' C2P' C3P' -178.4(6) . . . . ? C1P' C2P' C3P' C4P' -0.4(11) . . . . ? C2P' C3P' C4P' C5P' -1.5(12) . . . . ? C3P' C4P' C5P' C6P' 1.8(12) . . . . ? C4P' C5P' C6P' C1P' -0.2(12) . . . . ? C2P' C1P' C6P' C5P' -1.8(11) . . . . ? Se' C1P' C6P' C5P' 178.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.934 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.934 _refine_diff_density_max 0.62 _refine_diff_density_min -0.45 _refine_diff_density_rms 0.09