# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Waro Nakanishi' _publ_contact_author_email NAKANISI@SYS.WAKAYAMA-U.AC.JP _publ_section_title ; Structures and Dynamic Stereochemistry of 9-Arylselanyltriptycenes: X-ray Crystallographic, Spectroscopic and Theoretical Investigations ; loop_ _publ_author_name 'Waro Nakanishi' 'Satoko Hayashi' 'Mao Minoura' 'Takashi Nakamoto' 'Gaku Yamamoto' # Attachment '1a_Se_H_Rev.cif' data_1a_wn001_0m _database_code_depnum_ccdc_archive 'CCDC 704856' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H18 Se' _chemical_formula_weight 409.36 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 9.8178(5) _cell_length_b 15.3715(7) _cell_length_c 12.2627(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.809(1) _cell_angle_gamma 90.00 _cell_volume 1849.69(16) _cell_formula_units_Z 4 _cell_measurement_temperature 233 _cell_measurement_reflns_used 5421 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 28.17 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 2.037 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5801 _exptl_absorpt_correction_T_max 0.6861 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 233 _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 APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 10072 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4133 _reflns_number_gt 3598 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0327P)^2^+0.9850P] 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 4133 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0310 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0632 _refine_ls_wR_factor_gt 0.0600 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.103036(16) 0.106252(11) 0.441662(13) 0.01457(6) Uani 1 1 d . . . C1 C 0.20789(16) 0.18097(11) 0.34557(13) 0.0127(3) Uani 1 1 d . . . C2 C 0.14822(16) 0.17496(11) 0.22822(13) 0.0138(3) Uani 1 1 d . . . C3 C 0.03851(17) 0.12530(11) 0.19058(14) 0.0164(3) Uani 1 1 d . . . H3A H -0.0093 0.0901 0.2391 0.020 Uiso 1 1 calc R . . C4 C -0.00044(18) 0.12801(12) 0.07984(15) 0.0199(4) Uani 1 1 d . . . H4A H -0.0745 0.0944 0.0538 0.024 Uiso 1 1 calc R . . C5 C 0.06955(18) 0.17997(12) 0.00846(14) 0.0205(4) Uani 1 1 d . . . H5A H 0.0428 0.1813 -0.0658 0.025 Uiso 1 1 calc R . . C6 C 0.17967(18) 0.23055(12) 0.04591(14) 0.0182(4) Uani 1 1 d . . . H6A H 0.2267 0.2661 -0.0027 0.022 Uiso 1 1 calc R . . C7 C 0.21863(16) 0.22778(11) 0.15528(14) 0.0151(3) Uani 1 1 d . . . C8 C 0.33554(16) 0.27905(11) 0.20898(13) 0.0145(3) Uani 1 1 d . . . H8A H 0.3841 0.3161 0.1569 0.017 Uiso 1 1 calc R . . C9 C 0.27156(16) 0.33072(11) 0.29984(13) 0.0148(3) Uani 1 1 d . . . C10 C 0.27130(17) 0.42056(12) 0.31009(15) 0.0184(4) Uani 1 1 d . . . H10A H 0.3168 0.4553 0.2597 0.022 Uiso 1 1 calc R . . C11 C 0.20296(18) 0.45912(12) 0.39581(15) 0.0208(4) Uani 1 1 d . . . H11A H 0.2032 0.5200 0.4037 0.025 Uiso 1 1 calc R . . C12 C 0.13467(18) 0.40773(12) 0.46936(15) 0.0193(4) Uani 1 1 d . . . H12A H 0.0893 0.4339 0.5272 0.023 Uiso 1 1 calc R . . C13 C 0.13299(16) 0.31725(12) 0.45790(13) 0.0158(3) Uani 1 1 d . . . H13A H 0.0850 0.2828 0.5070 0.019 Uiso 1 1 calc R . . C14 C 0.20224(16) 0.27856(11) 0.37396(13) 0.0136(3) Uani 1 1 d . . . C15 C 0.35876(16) 0.15533(11) 0.33395(13) 0.0131(3) Uani 1 1 d . . . C16 C 0.42556(18) 0.08427(11) 0.37974(14) 0.0160(3) Uani 1 1 d . . . H16A H 0.3789 0.0455 0.4245 0.019 Uiso 1 1 calc R . . C17 C 0.56297(18) 0.07072(12) 0.35884(14) 0.0192(4) Uani 1 1 d . . . H17A H 0.6088 0.0224 0.3893 0.023 Uiso 1 1 calc R . . C18 C 0.63209(18) 0.12836(12) 0.29337(15) 0.0198(4) Uani 1 1 d . . . H18A H 0.7254 0.1201 0.2819 0.024 Uiso 1 1 calc R . . C19 C 0.56411(17) 0.19841(11) 0.24450(14) 0.0164(3) Uani 1 1 d . . . H19A H 0.6107 0.2369 0.1993 0.020 Uiso 1 1 calc R . . C20 C 0.42689(16) 0.21075(11) 0.26326(13) 0.0138(3) Uani 1 1 d . . . C21 C 0.19426(16) 0.11725(10) 0.58196(13) 0.0130(3) Uani 1 1 d . . . C22 C 0.13064(17) 0.07334(11) 0.66600(14) 0.0152(3) Uani 1 1 d . . . H22A H 0.0488 0.0431 0.6513 0.018 Uiso 1 1 calc R . . C23 C 0.18745(18) 0.07401(12) 0.77114(14) 0.0187(4) Uani 1 1 d . . . H23A H 0.1442 0.0443 0.8274 0.022 Uiso 1 1 calc R . . C24 C 0.30852(19) 0.11874(12) 0.79300(15) 0.0195(4) Uani 1 1 d . . . H24A H 0.3477 0.1190 0.8639 0.023 Uiso 1 1 calc R . . C25 C 0.37085(17) 0.16285(12) 0.70982(14) 0.0187(4) Uani 1 1 d . . . H25A H 0.4526 0.1930 0.7248 0.022 Uiso 1 1 calc R . . C26 C 0.31411(16) 0.16319(11) 0.60412(14) 0.0154(3) Uani 1 1 d . . . H26A H 0.3564 0.1942 0.5484 0.019 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 0.01511(9) 0.01566(9) 0.01292(9) 0.00105(6) -0.00002(6) -0.00445(6) C1 0.0133(7) 0.0123(8) 0.0125(7) 0.0017(6) 0.0008(6) -0.0010(6) C2 0.0145(8) 0.0140(8) 0.0130(8) -0.0002(6) -0.0002(6) 0.0037(6) C3 0.0164(8) 0.0142(8) 0.0186(9) -0.0002(7) -0.0004(6) 0.0025(6) C4 0.0182(8) 0.0192(9) 0.0221(9) -0.0047(7) -0.0058(7) 0.0017(7) C5 0.0240(9) 0.0235(9) 0.0137(8) -0.0012(7) -0.0039(7) 0.0075(7) C6 0.0211(9) 0.0186(9) 0.0150(8) 0.0032(7) 0.0019(7) 0.0048(7) C7 0.0151(8) 0.0143(8) 0.0159(8) 0.0007(6) 0.0009(6) 0.0037(6) C8 0.0151(8) 0.0139(8) 0.0145(8) 0.0023(6) 0.0020(6) -0.0002(6) C9 0.0128(7) 0.0154(8) 0.0160(8) 0.0010(7) -0.0015(6) 0.0009(6) C10 0.0179(8) 0.0153(8) 0.0218(9) 0.0023(7) -0.0010(7) -0.0012(7) C11 0.0225(9) 0.0125(8) 0.0273(10) -0.0011(7) -0.0022(7) 0.0029(7) C12 0.0180(8) 0.0205(9) 0.0193(9) -0.0038(7) -0.0011(7) 0.0048(7) C13 0.0141(8) 0.0181(9) 0.0153(8) 0.0013(7) 0.0002(6) 0.0011(6) C14 0.0128(7) 0.0131(8) 0.0148(8) -0.0001(6) -0.0036(6) 0.0009(6) C15 0.0145(8) 0.0135(8) 0.0112(7) -0.0021(6) -0.0004(6) -0.0005(6) C16 0.0207(8) 0.0142(8) 0.0133(8) 0.0007(6) 0.0020(6) 0.0006(7) C17 0.0212(9) 0.0177(9) 0.0186(9) 0.0002(7) -0.0008(7) 0.0067(7) C18 0.0156(8) 0.0236(9) 0.0202(9) -0.0028(7) 0.0030(7) 0.0046(7) C19 0.0175(8) 0.0175(9) 0.0144(8) -0.0014(7) 0.0034(6) -0.0014(7) C20 0.0168(8) 0.0124(8) 0.0122(8) -0.0010(6) -0.0010(6) 0.0004(6) C21 0.0139(8) 0.0121(8) 0.0129(8) -0.0012(6) 0.0004(6) 0.0021(6) C22 0.0164(8) 0.0124(8) 0.0170(8) -0.0013(7) 0.0022(6) -0.0021(6) C23 0.0233(9) 0.0178(9) 0.0152(8) 0.0007(7) 0.0023(7) -0.0008(7) C24 0.0232(9) 0.0192(9) 0.0158(8) -0.0022(7) -0.0029(7) 0.0010(7) C25 0.0152(8) 0.0191(9) 0.0218(9) -0.0034(7) -0.0012(7) -0.0020(7) C26 0.0144(8) 0.0147(8) 0.0174(8) 0.0004(7) 0.0039(6) -0.0011(6) _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 C21 1.9218(16) . ? Se1 C1 1.9606(16) . ? C1 C2 1.539(2) . ? C1 C14 1.541(2) . ? C1 C15 1.544(2) . ? C2 C3 1.387(2) . ? C2 C7 1.406(2) . ? C3 C4 1.400(2) . ? C3 H3A 0.9400 . ? C4 C5 1.384(3) . ? C4 H4A 0.9400 . ? C5 C6 1.398(3) . ? C5 H5A 0.9400 . ? C6 C7 1.384(2) . ? C6 H6A 0.9400 . ? C7 C8 1.525(2) . ? C8 C9 1.520(2) . ? C8 C20 1.520(2) . ? C8 H8A 0.9900 . ? C9 C10 1.387(2) . ? C9 C14 1.404(2) . ? C10 C11 1.397(3) . ? C10 H10A 0.9400 . ? C11 C12 1.388(3) . ? C11 H11A 0.9400 . ? C12 C13 1.398(2) . ? C12 H12A 0.9400 . ? C13 C14 1.386(2) . ? C13 H13A 0.9400 . ? C15 C16 1.384(2) . ? C15 C20 1.400(2) . ? C16 C17 1.397(2) . ? C16 H16A 0.9400 . ? C17 C18 1.387(3) . ? C17 H17A 0.9400 . ? C18 C19 1.392(3) . ? C18 H18A 0.9400 . ? C19 C20 1.387(2) . ? C19 H19A 0.9400 . ? C21 C26 1.392(2) . ? C21 C22 1.396(2) . ? C22 C23 1.389(2) . ? C22 H22A 0.9400 . ? C23 C24 1.392(3) . ? C23 H23A 0.9400 . ? C24 C25 1.383(3) . ? C24 H24A 0.9400 . ? C25 C26 1.395(2) . ? C25 H25A 0.9400 . ? C26 H26A 0.9400 . ? 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 C21 Se1 C1 104.35(7) . . ? C2 C1 C14 104.73(13) . . ? C2 C1 C15 103.68(12) . . ? C14 C1 C15 108.10(13) . . ? C2 C1 Se1 109.58(10) . . ? C14 C1 Se1 114.27(11) . . ? C15 C1 Se1 115.44(11) . . ? C3 C2 C7 119.89(15) . . ? C3 C2 C1 127.78(15) . . ? C7 C2 C1 112.33(14) . . ? C2 C3 C4 119.46(16) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C5 C4 C3 120.34(17) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C4 C5 C6 120.52(16) . . ? C4 C5 H5A 119.7 . . ? C6 C5 H5A 119.7 . . ? C7 C6 C5 119.25(16) . . ? C7 C6 H6A 120.4 . . ? C5 C6 H6A 120.4 . . ? C6 C7 C2 120.54(16) . . ? C6 C7 C8 125.74(15) . . ? C2 C7 C8 113.72(14) . . ? C9 C8 C20 106.95(13) . . ? C9 C8 C7 105.29(13) . . ? C20 C8 C7 104.94(13) . . ? C9 C8 H8A 113.0 . . ? C20 C8 H8A 113.0 . . ? C7 C8 H8A 113.0 . . ? C10 C9 C14 120.51(16) . . ? C10 C9 C8 126.07(15) . . ? C14 C9 C8 113.33(15) . . ? C9 C10 C11 119.55(16) . . ? C9 C10 H10A 120.2 . . ? C11 C10 H10A 120.2 . . ? C12 C11 C10 120.07(17) . . ? C12 C11 H11A 120.0 . . ? C10 C11 H11A 120.0 . . ? C11 C12 C13 120.37(16) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? C14 C13 C12 119.82(16) . . ? C14 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? C13 C14 C9 119.68(16) . . ? C13 C14 C1 127.41(15) . . ? C9 C14 C1 112.83(14) . . ? C16 C15 C20 120.12(15) . . ? C16 C15 C1 127.43(15) . . ? C20 C15 C1 112.35(14) . . ? C15 C16 C17 119.43(16) . . ? C15 C16 H16A 120.3 . . ? C17 C16 H16A 120.3 . . ? C18 C17 C16 120.25(16) . . ? C18 C17 H17A 119.9 . . ? C16 C17 H17A 119.9 . . ? C17 C18 C19 120.43(16) . . ? C17 C18 H18A 119.8 . . ? C19 C18 H18A 119.8 . . ? C20 C19 C18 119.29(16) . . ? C20 C19 H19A 120.4 . . ? C18 C19 H19A 120.4 . . ? C19 C20 C15 120.33(15) . . ? C19 C20 C8 125.76(15) . . ? C15 C20 C8 113.85(14) . . ? C26 C21 C22 119.77(15) . . ? C26 C21 Se1 125.92(13) . . ? C22 C21 Se1 114.31(12) . . ? C23 C22 C21 120.39(16) . . ? C23 C22 H22A 119.8 . . ? C21 C22 H22A 119.8 . . ? C22 C23 C24 119.88(16) . . ? C22 C23 H23A 120.1 . . ? C24 C23 H23A 120.1 . . ? C25 C24 C23 119.67(16) . . ? C25 C24 H24A 120.2 . . ? C23 C24 H24A 120.2 . . ? C24 C25 C26 120.94(16) . . ? C24 C25 H25A 119.5 . . ? C26 C25 H25A 119.5 . . ? C21 C26 C25 119.34(15) . . ? C21 C26 H26A 120.3 . . ? C25 C26 H26A 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 C21 Se1 C1 C2 177.66(10) . . . . ? C21 Se1 C1 C14 -65.19(12) . . . . ? C21 Se1 C1 C15 61.10(13) . . . . ? C14 C1 C2 C3 -123.50(17) . . . . ? C15 C1 C2 C3 123.26(17) . . . . ? Se1 C1 C2 C3 -0.5(2) . . . . ? C14 C1 C2 C7 56.56(17) . . . . ? C15 C1 C2 C7 -56.69(17) . . . . ? Se1 C1 C2 C7 179.55(11) . . . . ? C7 C2 C3 C4 0.4(2) . . . . ? C1 C2 C3 C4 -179.57(16) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? C4 C5 C6 C7 0.4(3) . . . . ? C5 C6 C7 C2 -0.2(3) . . . . ? C5 C6 C7 C8 -179.70(16) . . . . ? C3 C2 C7 C6 -0.2(2) . . . . ? C1 C2 C7 C6 179.78(15) . . . . ? C3 C2 C7 C8 179.39(15) . . . . ? C1 C2 C7 C8 -0.7(2) . . . . ? C6 C7 C8 C9 123.52(17) . . . . ? C2 C7 C8 C9 -56.02(18) . . . . ? C6 C7 C8 C20 -123.79(17) . . . . ? C2 C7 C8 C20 56.67(17) . . . . ? C20 C8 C9 C10 128.28(17) . . . . ? C7 C8 C9 C10 -120.45(17) . . . . ? C20 C8 C9 C14 -55.15(17) . . . . ? C7 C8 C9 C14 56.13(17) . . . . ? C14 C9 C10 C11 0.9(2) . . . . ? C8 C9 C10 C11 177.21(15) . . . . ? C9 C10 C11 C12 -0.7(3) . . . . ? C10 C11 C12 C13 -0.4(3) . . . . ? C11 C12 C13 C14 1.3(3) . . . . ? C12 C13 C14 C9 -1.2(2) . . . . ? C12 C13 C14 C1 -177.52(16) . . . . ? C10 C9 C14 C13 0.1(2) . . . . ? C8 C9 C14 C13 -176.73(14) . . . . ? C10 C9 C14 C1 176.93(14) . . . . ? C8 C9 C14 C1 0.14(19) . . . . ? C2 C1 C14 C13 120.05(17) . . . . ? C15 C1 C14 C13 -129.89(17) . . . . ? Se1 C1 C14 C13 0.1(2) . . . . ? C2 C1 C14 C9 -56.53(17) . . . . ? C15 C1 C14 C9 53.54(17) . . . . ? Se1 C1 C14 C9 -176.44(11) . . . . ? C2 C1 C15 C16 -116.95(17) . . . . ? C14 C1 C15 C16 132.26(17) . . . . ? Se1 C1 C15 C16 2.9(2) . . . . ? C2 C1 C15 C20 59.43(17) . . . . ? C14 C1 C15 C20 -51.35(17) . . . . ? Se1 C1 C15 C20 179.28(11) . . . . ? C20 C15 C16 C17 3.0(2) . . . . ? C1 C15 C16 C17 179.09(16) . . . . ? C15 C16 C17 C18 0.4(3) . . . . ? C16 C17 C18 C19 -2.4(3) . . . . ? C17 C18 C19 C20 1.0(3) . . . . ? C18 C19 C20 C15 2.5(2) . . . . ? C18 C19 C20 C8 -174.57(16) . . . . ? C16 C15 C20 C19 -4.4(2) . . . . ? C1 C15 C20 C19 178.87(15) . . . . ? C16 C15 C20 C8 172.92(15) . . . . ? C1 C15 C20 C8 -3.8(2) . . . . ? C9 C8 C20 C19 -125.32(17) . . . . ? C7 C8 C20 C19 123.17(17) . . . . ? C9 C8 C20 C15 57.49(18) . . . . ? C7 C8 C20 C15 -54.03(17) . . . . ? C1 Se1 C21 C26 -4.61(16) . . . . ? C1 Se1 C21 C22 175.91(12) . . . . ? C26 C21 C22 C23 -1.1(2) . . . . ? Se1 C21 C22 C23 178.42(13) . . . . ? C21 C22 C23 C24 0.0(3) . . . . ? C22 C23 C24 C25 0.5(3) . . . . ? C23 C24 C25 C26 0.0(3) . . . . ? C22 C21 C26 C25 1.6(2) . . . . ? Se1 C21 C26 C25 -177.86(13) . . . . ? C24 C25 C26 C21 -1.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 0.421 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.060 # Attachment '1b_Se_NMe2_Rev.cif' data_1b_wn006nm _database_code_depnum_ccdc_archive 'CCDC 704857' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H23 N Se' _chemical_formula_weight 452.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6439(4) _cell_length_b 11.2233(5) _cell_length_c 20.4121(8) _cell_angle_alpha 74.692(1) _cell_angle_beta 87.418(1) _cell_angle_gamma 77.849(1) _cell_volume 2083.08(15) _cell_formula_units_Z 4 _cell_measurement_temperature 233 _cell_measurement_reflns_used 6102 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.98 _exptl_crystal_description needle _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 1.818 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4635 _exptl_absorpt_correction_T_max 0.8391 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 233 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 11611 _diffrn_reflns_av_R_equivalents 0.0137 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.50 _reflns_number_total 8849 _reflns_number_gt 7573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0551P)^2^+1.3553P] 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 8849 _refine_ls_number_parameters 545 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0340 _refine_ls_wR_factor_ref 0.0980 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.77280(2) 0.29685(2) 0.319673(12) 0.01833(7) Uani 1 1 d . . . C1 C 0.8285(2) 0.1491(2) 0.28365(11) 0.0155(4) Uani 1 1 d . . . C2 C 0.6976(2) 0.1214(2) 0.25447(11) 0.0157(4) Uani 1 1 d . . . C3 C 0.5577(2) 0.1833(2) 0.25561(12) 0.0185(5) Uani 1 1 d . . . H3A H 0.5344 0.2534 0.2740 0.022 Uiso 1 1 calc R . . C4 C 0.4516(3) 0.1413(2) 0.22930(13) 0.0221(5) Uani 1 1 d . . . H4A H 0.3565 0.1831 0.2301 0.026 Uiso 1 1 calc R . . C5 C 0.4854(3) 0.0382(2) 0.20195(12) 0.0229(5) Uani 1 1 d . . . H5A H 0.4133 0.0108 0.1841 0.027 Uiso 1 1 calc R . . C6 C 0.6266(3) -0.0250(2) 0.20093(12) 0.0208(5) Uani 1 1 d . . . H6A H 0.6498 -0.0950 0.1825 0.025 Uiso 1 1 calc R . . C7 C 0.7318(2) 0.0163(2) 0.22724(11) 0.0168(4) Uani 1 1 d . . . C8 C 0.8892(2) -0.0477(2) 0.23437(11) 0.0169(4) Uani 1 1 d . . . H8A H 0.9122 -0.1223 0.2156 0.020 Uiso 1 1 calc R . . C9 C 0.9701(2) 0.0550(2) 0.20042(11) 0.0166(4) Uani 1 1 d . . . C10 C 1.0671(2) 0.0503(2) 0.14838(12) 0.0189(5) Uani 1 1 d . . . H10A H 1.0924 -0.0226 0.1325 0.023 Uiso 1 1 calc R . . C11 C 1.1267(3) 0.1553(2) 0.12000(12) 0.0208(5) Uani 1 1 d . . . H11A H 1.1939 0.1525 0.0853 0.025 Uiso 1 1 calc R . . C12 C 1.0877(3) 0.2637(2) 0.14253(12) 0.0211(5) Uani 1 1 d . . . H12A H 1.1267 0.3345 0.1222 0.025 Uiso 1 1 calc R . . C13 C 0.9910(2) 0.2683(2) 0.19502(12) 0.0192(5) Uani 1 1 d . . . H13A H 0.9641 0.3420 0.2101 0.023 Uiso 1 1 calc R . . C14 C 0.9348(2) 0.1627(2) 0.22486(11) 0.0161(4) Uani 1 1 d . . . C15 C 0.8859(2) 0.0253(2) 0.33759(11) 0.0147(4) Uani 1 1 d . . . C16 C 0.8954(2) 0.0088(2) 0.40707(12) 0.0178(5) Uani 1 1 d . . . H16A H 0.8744 0.0791 0.4253 0.021 Uiso 1 1 calc R . . C17 C 0.9361(3) -0.1121(2) 0.44980(12) 0.0214(5) Uani 1 1 d . . . H17A H 0.9418 -0.1236 0.4970 0.026 Uiso 1 1 calc R . . C18 C 0.9684(3) -0.2161(2) 0.42260(12) 0.0224(5) Uani 1 1 d . . . H18A H 0.9969 -0.2976 0.4515 0.027 Uiso 1 1 calc R . . C19 C 0.9588(2) -0.2003(2) 0.35266(12) 0.0191(5) Uani 1 1 d . . . H19A H 0.9800 -0.2706 0.3344 0.023 Uiso 1 1 calc R . . C20 C 0.9177(2) -0.0798(2) 0.31049(11) 0.0158(4) Uani 1 1 d . . . C21 C 0.9469(2) 0.3107(2) 0.35643(11) 0.0175(5) Uani 1 1 d . . . C22 C 0.9335(3) 0.4045(2) 0.39061(12) 0.0183(5) Uani 1 1 d . . . H22A H 0.8427 0.4502 0.3970 0.022 Uiso 1 1 calc R . . C23 C 1.0511(3) 0.4320(2) 0.41537(12) 0.0198(5) Uani 1 1 d . . . H23A H 1.0385 0.4971 0.4375 0.024 Uiso 1 1 calc R . . C24 C 1.1888(3) 0.3646(2) 0.40816(12) 0.0195(5) Uani 1 1 d . . . C25 C 1.2009(3) 0.2697(2) 0.37350(12) 0.0204(5) Uani 1 1 d . . . H25A H 1.2913 0.2231 0.3672 0.024 Uiso 1 1 calc R . . C26 C 1.0821(3) 0.2435(2) 0.34841(12) 0.0198(5) Uani 1 1 d . . . H26A H 1.0936 0.1793 0.3257 0.024 Uiso 1 1 calc R . . N1 N 1.3067(2) 0.3877(2) 0.43561(11) 0.0253(5) Uani 1 1 d . . . C27 C 1.2917(3) 0.5043(3) 0.45620(17) 0.0387(7) Uani 1 1 d . . . H27A H 1.2615 0.5758 0.4175 0.058 Uiso 1 1 calc R . . H27B H 1.3822 0.5092 0.4732 0.058 Uiso 1 1 calc R . . H27C H 1.2215 0.5057 0.4917 0.058 Uiso 1 1 calc R . . C28 C 1.4459(3) 0.3422(3) 0.41081(14) 0.0285(6) Uani 1 1 d . . . H28A H 1.4623 0.2513 0.4186 0.043 Uiso 1 1 calc R . . H28B H 1.5178 0.3637 0.4347 0.043 Uiso 1 1 calc R . . H28C H 1.4507 0.3812 0.3625 0.043 Uiso 1 1 calc R . . Se2 Se 0.43458(3) 0.53843(2) 0.212493(12) 0.02089(8) Uani 1 1 d . . . C29 C 0.2966(2) 0.6110(2) 0.13748(11) 0.0168(4) Uani 1 1 d . . . C30 C 0.3248(2) 0.5248(2) 0.08837(12) 0.0173(5) Uani 1 1 d . . . C31 C 0.4281(3) 0.4152(2) 0.09483(13) 0.0212(5) Uani 1 1 d . . . H31A H 0.4893 0.3847 0.1329 0.025 Uiso 1 1 calc R . . C32 C 0.4399(3) 0.3509(2) 0.04423(14) 0.0249(5) Uani 1 1 d . . . H32A H 0.5093 0.2766 0.0483 0.030 Uiso 1 1 calc R . . C33 C 0.3506(3) 0.3955(2) -0.01177(14) 0.0257(5) Uani 1 1 d . . . H33A H 0.3612 0.3524 -0.0460 0.031 Uiso 1 1 calc R . . C34 C 0.2444(3) 0.5046(2) -0.01807(13) 0.0232(5) Uani 1 1 d . . . H34A H 0.1823 0.5340 -0.0558 0.028 Uiso 1 1 calc R . . C35 C 0.2325(2) 0.5681(2) 0.03212(12) 0.0188(5) Uani 1 1 d . . . C36 C 0.1259(2) 0.6894(2) 0.03213(12) 0.0186(5) Uani 1 1 d . . . H36A H 0.0610 0.7190 -0.0078 0.022 Uiso 1 1 calc R . . C37 C 0.0485(2) 0.6627(2) 0.09929(12) 0.0176(5) Uani 1 1 d . . . C38 C -0.0969(3) 0.6771(2) 0.10603(13) 0.0207(5) Uani 1 1 d . . . H38A H -0.1566 0.7083 0.0675 0.025 Uiso 1 1 calc R . . C39 C -0.1538(3) 0.6448(2) 0.17074(13) 0.0226(5) Uani 1 1 d . . . H39A H -0.2525 0.6540 0.1760 0.027 Uiso 1 1 calc R . . C40 C -0.0653(3) 0.5992(2) 0.22704(13) 0.0217(5) Uani 1 1 d . . . H40A H -0.1047 0.5775 0.2705 0.026 Uiso 1 1 calc R . . C41 C 0.0824(3) 0.5848(2) 0.22059(12) 0.0191(5) Uani 1 1 d . . . H41A H 0.1418 0.5531 0.2592 0.023 Uiso 1 1 calc R . . C42 C 0.1391(2) 0.6181(2) 0.15643(12) 0.0173(5) Uani 1 1 d . . . C43 C 0.3067(2) 0.7434(2) 0.09307(11) 0.0161(4) Uani 1 1 d . . . C44 C 0.3950(2) 0.8199(2) 0.10272(12) 0.0182(5) Uani 1 1 d . . . H44A H 0.4591 0.7928 0.1396 0.022 Uiso 1 1 calc R . . C45 C 0.3876(3) 0.9382(2) 0.05685(12) 0.0211(5) Uani 1 1 d . . . H45A H 0.4464 0.9911 0.0635 0.025 Uiso 1 1 calc R . . C46 C 0.2950(3) 0.9785(2) 0.00189(13) 0.0244(5) Uani 1 1 d . . . H46A H 0.2914 1.0584 -0.0284 0.029 Uiso 1 1 calc R . . C47 C 0.2071(3) 0.9014(2) -0.00875(12) 0.0214(5) Uani 1 1 d . . . H47A H 0.1447 0.9281 -0.0463 0.026 Uiso 1 1 calc R . . C48 C 0.2133(2) 0.7847(2) 0.03680(11) 0.0177(5) Uani 1 1 d . . . C49 C 0.4210(3) 0.6599(2) 0.26466(12) 0.0194(5) Uani 1 1 d . . . C54 C 0.3019(3) 0.7504(2) 0.27192(13) 0.0245(5) Uani 1 1 d . . . H54A H 0.2180 0.7589 0.2479 0.029 Uiso 1 1 calc R . . C53 C 0.3064(3) 0.8277(3) 0.31428(15) 0.0299(6) Uani 1 1 d . . . H53A H 0.2255 0.8892 0.3178 0.036 Uiso 1 1 calc R . . C52 C 0.4284(3) 0.8166(3) 0.35207(14) 0.0309(6) Uani 1 1 d . . . C51 C 0.5478(3) 0.7263(3) 0.34431(13) 0.0293(6) Uani 1 1 d . . . H51A H 0.6315 0.7168 0.3687 0.035 Uiso 1 1 calc R . . C50 C 0.5439(3) 0.6503(3) 0.30071(13) 0.0250(5) Uani 1 1 d . . . H50A H 0.6258 0.5912 0.2955 0.030 Uiso 1 1 calc R . . N2 N 0.4278(3) 0.9009(3) 0.39291(15) 0.0517(9) Uani 1 1 d . . . C56 C 0.3111(3) 0.9220(3) 0.43527(18) 0.0414(8) Uani 1 1 d . . . H56A H 0.2238 0.9377 0.4097 0.062 Uiso 1 1 calc R . . H56B H 0.3141 0.9947 0.4520 0.062 Uiso 1 1 calc R . . H56C H 0.3148 0.8483 0.4733 0.062 Uiso 1 1 calc R . . C55 C 0.5647(3) 0.9045(3) 0.41836(15) 0.0348(7) Uani 1 1 d . . . H55A H 0.6026 0.8245 0.4503 0.052 Uiso 1 1 calc R . . H55B H 0.5535 0.9719 0.4410 0.052 Uiso 1 1 calc R . . H55C H 0.6295 0.9197 0.3808 0.052 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 0.01435(12) 0.01583(12) 0.02622(13) -0.01019(9) -0.00300(9) 0.00049(9) C1 0.0158(11) 0.0142(11) 0.0176(11) -0.0057(9) -0.0012(8) -0.0032(9) C2 0.0157(11) 0.0134(10) 0.0164(11) -0.0013(8) -0.0042(8) -0.0019(9) C3 0.0192(11) 0.0144(11) 0.0207(11) -0.0039(9) -0.0025(9) -0.0009(9) C4 0.0157(11) 0.0229(12) 0.0244(12) -0.0028(10) -0.0047(9) -0.0003(10) C5 0.0205(12) 0.0258(13) 0.0225(12) -0.0033(10) -0.0077(9) -0.0078(10) C6 0.0264(13) 0.0187(12) 0.0178(11) -0.0046(9) -0.0023(9) -0.0055(10) C7 0.0186(11) 0.0131(10) 0.0158(11) -0.0009(8) -0.0032(9) 0.0000(9) C8 0.0188(11) 0.0145(11) 0.0172(11) -0.0049(9) -0.0016(9) -0.0016(9) C9 0.0166(11) 0.0164(11) 0.0149(11) -0.0019(8) -0.0051(8) -0.0010(9) C10 0.0190(11) 0.0183(11) 0.0168(11) -0.0044(9) -0.0038(9) 0.0026(9) C11 0.0163(11) 0.0252(12) 0.0168(11) -0.0018(9) -0.0014(9) 0.0001(10) C12 0.0195(12) 0.0207(12) 0.0202(12) 0.0015(9) -0.0035(9) -0.0054(10) C13 0.0192(11) 0.0157(11) 0.0209(12) -0.0023(9) -0.0048(9) -0.0020(9) C14 0.0129(10) 0.0172(11) 0.0163(11) -0.0028(9) -0.0044(8) -0.0001(9) C15 0.0105(10) 0.0140(10) 0.0187(11) -0.0039(9) -0.0022(8) -0.0008(8) C16 0.0145(11) 0.0203(11) 0.0199(11) -0.0074(9) 0.0000(9) -0.0036(9) C17 0.0190(11) 0.0289(13) 0.0157(11) -0.0040(10) -0.0015(9) -0.0052(10) C18 0.0225(12) 0.0191(12) 0.0210(12) 0.0008(9) -0.0016(10) -0.0012(10) C19 0.0179(11) 0.0161(11) 0.0227(12) -0.0053(9) 0.0006(9) -0.0021(9) C20 0.0127(10) 0.0161(11) 0.0179(11) -0.0041(9) -0.0014(8) -0.0018(9) C21 0.0169(11) 0.0174(11) 0.0179(11) -0.0039(9) -0.0029(9) -0.0034(9) C22 0.0178(11) 0.0177(11) 0.0181(11) -0.0051(9) -0.0005(9) -0.0003(9) C23 0.0251(12) 0.0184(11) 0.0177(11) -0.0064(9) -0.0014(9) -0.0055(10) C24 0.0189(11) 0.0231(12) 0.0157(11) -0.0013(9) -0.0014(9) -0.0072(10) C25 0.0171(11) 0.0238(12) 0.0189(11) -0.0053(9) -0.0009(9) -0.0012(10) C26 0.0219(12) 0.0179(11) 0.0196(11) -0.0056(9) -0.0018(9) -0.0025(10) N1 0.0196(10) 0.0345(12) 0.0262(11) -0.0128(9) -0.0006(8) -0.0084(9) C27 0.0251(14) 0.0539(19) 0.0510(19) -0.0348(16) -0.0010(13) -0.0116(14) C28 0.0206(13) 0.0361(15) 0.0309(14) -0.0105(12) -0.0024(10) -0.0073(11) Se2 0.02199(13) 0.01792(13) 0.02003(13) -0.00272(9) -0.00797(9) 0.00076(10) C29 0.0158(11) 0.0178(11) 0.0165(11) -0.0039(9) -0.0027(8) -0.0028(9) C30 0.0171(11) 0.0162(11) 0.0190(11) -0.0037(9) 0.0015(9) -0.0058(9) C31 0.0190(11) 0.0181(11) 0.0253(12) -0.0033(9) 0.0008(9) -0.0040(10) C32 0.0206(12) 0.0205(12) 0.0356(14) -0.0109(11) 0.0060(10) -0.0052(10) C33 0.0239(13) 0.0283(13) 0.0328(14) -0.0184(11) 0.0081(11) -0.0108(11) C34 0.0212(12) 0.0298(13) 0.0230(12) -0.0111(10) 0.0007(10) -0.0094(10) C35 0.0176(11) 0.0209(12) 0.0199(11) -0.0058(9) 0.0008(9) -0.0075(10) C36 0.0175(11) 0.0209(12) 0.0167(11) -0.0043(9) -0.0041(9) -0.0020(9) C37 0.0196(11) 0.0142(11) 0.0191(11) -0.0047(9) -0.0012(9) -0.0031(9) C38 0.0193(11) 0.0179(11) 0.0257(12) -0.0073(10) -0.0037(9) -0.0029(9) C39 0.0179(11) 0.0184(12) 0.0340(14) -0.0100(10) 0.0026(10) -0.0057(10) C40 0.0261(12) 0.0160(11) 0.0247(12) -0.0068(9) 0.0067(10) -0.0077(10) C41 0.0248(12) 0.0147(11) 0.0182(11) -0.0041(9) -0.0015(9) -0.0047(9) C42 0.0184(11) 0.0116(10) 0.0219(12) -0.0044(9) -0.0007(9) -0.0029(9) C43 0.0162(11) 0.0147(11) 0.0159(11) -0.0029(8) 0.0013(8) -0.0011(9) C44 0.0161(11) 0.0199(11) 0.0190(11) -0.0067(9) 0.0020(9) -0.0029(9) C45 0.0224(12) 0.0191(12) 0.0231(12) -0.0061(10) 0.0064(10) -0.0077(10) C46 0.0300(13) 0.0165(11) 0.0231(12) -0.0010(9) 0.0049(10) -0.0029(10) C47 0.0220(12) 0.0218(12) 0.0172(11) -0.0031(9) -0.0011(9) 0.0006(10) C48 0.0190(11) 0.0172(11) 0.0159(11) -0.0044(9) 0.0008(9) -0.0013(9) C49 0.0219(12) 0.0205(12) 0.0149(11) -0.0020(9) -0.0021(9) -0.0054(10) C54 0.0193(12) 0.0314(14) 0.0259(13) -0.0109(11) -0.0019(10) -0.0070(11) C53 0.0192(12) 0.0405(16) 0.0372(15) -0.0203(13) 0.0052(11) -0.0100(12) C52 0.0235(13) 0.0537(18) 0.0258(13) -0.0204(13) 0.0084(11) -0.0191(13) C51 0.0203(12) 0.0495(17) 0.0234(13) -0.0121(12) -0.0009(10) -0.0150(12) C50 0.0198(12) 0.0335(14) 0.0221(12) -0.0053(10) -0.0009(10) -0.0086(11) N2 0.0292(13) 0.101(3) 0.0525(17) -0.0565(18) 0.0150(12) -0.0315(15) C56 0.0291(15) 0.0462(19) 0.057(2) -0.0313(16) -0.0046(14) -0.0010(14) C55 0.0324(15) 0.0512(18) 0.0323(15) -0.0213(14) 0.0024(12) -0.0207(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 C21 1.921(2) . ? Se1 C1 1.953(2) . ? C1 C15 1.540(3) . ? C1 C14 1.541(3) . ? C1 C2 1.541(3) . ? C2 C3 1.383(3) . ? C2 C7 1.405(3) . ? C3 C4 1.395(3) . ? C3 H3A 0.9400 . ? C4 C5 1.386(4) . ? C4 H4A 0.9400 . ? C5 C6 1.399(4) . ? C5 H5A 0.9400 . ? C6 C7 1.382(3) . ? C6 H6A 0.9400 . ? C7 C8 1.533(3) . ? C8 C20 1.523(3) . ? C8 C9 1.525(3) . ? C8 H8A 0.9900 . ? C9 C10 1.388(3) . ? C9 C14 1.398(3) . ? C10 C11 1.396(3) . ? C10 H10A 0.9400 . ? C11 C12 1.385(4) . ? C11 H11A 0.9400 . ? C12 C13 1.392(3) . ? C12 H12A 0.9400 . ? C13 C14 1.388(3) . ? C13 H13A 0.9400 . ? C15 C16 1.385(3) . ? C15 C20 1.403(3) . ? C16 C17 1.392(3) . ? C16 H16A 0.9400 . ? C17 C18 1.394(3) . ? C17 H17A 0.9400 . ? C18 C19 1.396(3) . ? C18 H18A 0.9400 . ? C19 C20 1.384(3) . ? C19 H19A 0.9400 . ? C21 C26 1.389(3) . ? C21 C22 1.391(3) . ? C22 C23 1.385(3) . ? C22 H22A 0.9400 . ? C23 C24 1.406(3) . ? C23 H23A 0.9400 . ? C24 N1 1.390(3) . ? C24 C25 1.409(3) . ? C25 C26 1.391(3) . ? C25 H25A 0.9400 . ? C26 H26A 0.9400 . ? N1 C28 1.452(3) . ? N1 C27 1.455(4) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C28 H28C 0.9700 . ? Se2 C49 1.921(2) . ? Se2 C29 1.961(2) . ? C29 C42 1.542(3) . ? C29 C43 1.544(3) . ? C29 C30 1.546(3) . ? C30 C31 1.391(3) . ? C30 C35 1.401(3) . ? C31 C32 1.396(3) . ? C31 H31A 0.9400 . ? C32 C33 1.380(4) . ? C32 H32A 0.9400 . ? C33 C34 1.402(4) . ? C33 H33A 0.9400 . ? C34 C35 1.382(3) . ? C34 H34A 0.9400 . ? C35 C36 1.524(3) . ? C36 C48 1.518(3) . ? C36 C37 1.520(3) . ? C36 H36A 0.9900 . ? C37 C38 1.382(3) . ? C37 C42 1.405(3) . ? C38 C39 1.394(4) . ? C38 H38A 0.9400 . ? C39 C40 1.380(4) . ? C39 H39A 0.9400 . ? C40 C41 1.403(3) . ? C40 H40A 0.9400 . ? C41 C42 1.384(3) . ? C41 H41A 0.9400 . ? C43 C44 1.383(3) . ? C43 C48 1.408(3) . ? C44 C45 1.397(3) . ? C44 H44A 0.9400 . ? C45 C46 1.383(4) . ? C45 H45A 0.9400 . ? C46 C47 1.393(4) . ? C46 H46A 0.9400 . ? C47 C48 1.382(3) . ? C47 H47A 0.9400 . ? C49 C50 1.393(3) . ? C49 C54 1.395(4) . ? C54 C53 1.385(4) . ? C54 H54A 0.9400 . ? C53 C52 1.402(4) . ? C53 H53A 0.9400 . ? C52 C51 1.398(4) . ? C52 N2 1.415(4) . ? C51 C50 1.393(4) . ? C51 H51A 0.9400 . ? C50 H50A 0.9400 . ? N2 C56 1.407(4) . ? N2 C55 1.453(4) . ? C56 H56A 0.9700 . ? C56 H56B 0.9700 . ? C56 H56C 0.9700 . ? C55 H55A 0.9700 . ? C55 H55B 0.9700 . ? C55 H55C 0.9700 . ? 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 C21 Se1 C1 103.44(10) . . ? C15 C1 C14 108.25(18) . . ? C15 C1 C2 103.14(17) . . ? C14 C1 C2 105.14(18) . . ? C15 C1 Se1 114.29(15) . . ? C14 C1 Se1 114.99(15) . . ? C2 C1 Se1 110.00(15) . . ? C3 C2 C7 119.9(2) . . ? C3 C2 C1 127.6(2) . . ? C7 C2 C1 112.44(19) . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C4 C5 C6 120.1(2) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C7 C6 C5 119.5(2) . . ? C7 C6 H6A 120.3 . . ? C5 C6 H6A 120.3 . . ? C6 C7 C2 120.4(2) . . ? C6 C7 C8 125.8(2) . . ? C2 C7 C8 113.69(19) . . ? C20 C8 C9 107.14(18) . . ? C20 C8 C7 103.52(18) . . ? C9 C8 C7 105.85(18) . . ? C20 C8 H8A 113.2 . . ? C9 C8 H8A 113.2 . . ? C7 C8 H8A 113.2 . . ? C10 C9 C14 120.3(2) . . ? C10 C9 C8 126.0(2) . . ? C14 C9 C8 113.7(2) . . ? C9 C10 C11 119.1(2) . . ? C9 C10 H10A 120.5 . . ? C11 C10 H10A 120.5 . . ? C12 C11 C10 120.5(2) . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C11 C12 C13 120.4(2) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? C14 C13 C12 119.3(2) . . ? C14 C13 H13A 120.4 . . ? C12 C13 H13A 120.4 . . ? C13 C14 C9 120.3(2) . . ? C13 C14 C1 126.9(2) . . ? C9 C14 C1 112.77(19) . . ? C16 C15 C20 119.9(2) . . ? C16 C15 C1 127.1(2) . . ? C20 C15 C1 112.70(19) . . ? C15 C16 C17 119.9(2) . . ? C15 C16 H16A 120.0 . . ? C17 C16 H16A 120.0 . . ? C16 C17 C18 120.0(2) . . ? C16 C17 H17A 120.0 . . ? C18 C17 H17A 120.0 . . ? C17 C18 C19 120.5(2) . . ? C17 C18 H18A 119.8 . . ? C19 C18 H18A 119.8 . . ? C20 C19 C18 119.2(2) . . ? C20 C19 H19A 120.4 . . ? C18 C19 H19A 120.4 . . ? C19 C20 C15 120.5(2) . . ? C19 C20 C8 125.6(2) . . ? C15 C20 C8 113.67(19) . . ? C26 C21 C22 118.1(2) . . ? C26 C21 Se1 126.89(17) . . ? C22 C21 Se1 114.85(17) . . ? C23 C22 C21 121.4(2) . . ? C23 C22 H22A 119.3 . . ? C21 C22 H22A 119.3 . . ? C22 C23 C24 121.4(2) . . ? C22 C23 H23A 119.3 . . ? C24 C23 H23A 119.3 . . ? N1 C24 C23 121.7(2) . . ? N1 C24 C25 121.7(2) . . ? C23 C24 C25 116.6(2) . . ? C26 C25 C24 121.5(2) . . ? C26 C25 H25A 119.2 . . ? C24 C25 H25A 119.2 . . ? C21 C26 C25 120.9(2) . . ? C21 C26 H26A 119.5 . . ? C25 C26 H26A 119.5 . . ? C24 N1 C28 118.4(2) . . ? C24 N1 C27 118.3(2) . . ? C28 N1 C27 115.0(2) . . ? N1 C27 H27A 109.5 . . ? N1 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N1 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N1 C28 H28A 109.5 . . ? N1 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N1 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C49 Se2 C29 107.42(10) . . ? C42 C29 C43 106.00(18) . . ? C42 C29 C30 104.87(18) . . ? C43 C29 C30 104.93(18) . . ? C42 C29 Se2 116.39(15) . . ? C43 C29 Se2 115.87(15) . . ? C30 C29 Se2 107.66(15) . . ? C31 C30 C35 119.9(2) . . ? C31 C30 C29 127.3(2) . . ? C35 C30 C29 112.8(2) . . ? C30 C31 C32 119.3(2) . . ? C30 C31 H31A 120.4 . . ? C32 C31 H31A 120.4 . . ? C33 C32 C31 120.6(2) . . ? C33 C32 H32A 119.7 . . ? C31 C32 H32A 119.7 . . ? C32 C33 C34 120.6(2) . . ? C32 C33 H33A 119.7 . . ? C34 C33 H33A 119.7 . . ? C35 C34 C33 118.8(2) . . ? C35 C34 H34A 120.6 . . ? C33 C34 H34A 120.6 . . ? C34 C35 C30 120.9(2) . . ? C34 C35 C36 125.5(2) . . ? C30 C35 C36 113.7(2) . . ? C48 C36 C37 105.39(18) . . ? C48 C36 C35 105.79(19) . . ? C37 C36 C35 106.01(19) . . ? C48 C36 H36A 113.0 . . ? C37 C36 H36A 113.0 . . ? C35 C36 H36A 113.0 . . ? C38 C37 C42 121.1(2) . . ? C38 C37 C36 125.0(2) . . ? C42 C37 C36 113.8(2) . . ? C37 C38 C39 119.1(2) . . ? C37 C38 H38A 120.4 . . ? C39 C38 H38A 120.4 . . ? C40 C39 C38 120.1(2) . . ? C40 C39 H39A 120.0 . . ? C38 C39 H39A 120.0 . . ? C39 C40 C41 121.1(2) . . ? C39 C40 H40A 119.4 . . ? C41 C40 H40A 119.4 . . ? C42 C41 C40 118.9(2) . . ? C42 C41 H41A 120.5 . . ? C40 C41 H41A 120.5 . . ? C41 C42 C37 119.6(2) . . ? C41 C42 C29 127.8(2) . . ? C37 C42 C29 112.6(2) . . ? C44 C43 C48 119.7(2) . . ? C44 C43 C29 127.6(2) . . ? C48 C43 C29 112.75(19) . . ? C43 C44 C45 119.1(2) . . ? C43 C44 H44A 120.5 . . ? C45 C44 H44A 120.5 . . ? C46 C45 C44 121.0(2) . . ? C46 C45 H45A 119.5 . . ? C44 C45 H45A 119.5 . . ? C45 C46 C47 120.3(2) . . ? C45 C46 H46A 119.8 . . ? C47 C46 H46A 119.8 . . ? C48 C47 C46 118.9(2) . . ? C48 C47 H47A 120.6 . . ? C46 C47 H47A 120.6 . . ? C47 C48 C43 121.1(2) . . ? C47 C48 C36 125.4(2) . . ? C43 C48 C36 113.6(2) . . ? C50 C49 C54 118.3(2) . . ? C50 C49 Se2 114.53(19) . . ? C54 C49 Se2 127.14(18) . . ? C53 C54 C49 120.5(2) . . ? C53 C54 H54A 119.8 . . ? C49 C54 H54A 119.8 . . ? C54 C53 C52 121.7(3) . . ? C54 C53 H53A 119.2 . . ? C52 C53 H53A 119.2 . . ? C51 C52 C53 117.6(2) . . ? C51 C52 N2 123.3(3) . . ? C53 C52 N2 119.0(3) . . ? C50 C51 C52 120.6(2) . . ? C50 C51 H51A 119.7 . . ? C52 C51 H51A 119.7 . . ? C49 C50 C51 121.3(3) . . ? C49 C50 H50A 119.3 . . ? C51 C50 H50A 119.3 . . ? C56 N2 C52 118.6(2) . . ? C56 N2 C55 116.3(2) . . ? C52 N2 C55 116.4(3) . . ? N2 C56 H56A 109.5 . . ? N2 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? N2 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? N2 C55 H55A 109.5 . . ? N2 C55 H55A 109.5 . . ? H55A C55 H55A 109.5 . . ? N2 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 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 C21 Se1 C1 C15 62.23(17) . . . . ? C21 Se1 C1 C14 -63.88(18) . . . . ? C21 Se1 C1 C2 177.68(15) . . . . ? C15 C1 C2 C3 118.6(2) . . . . ? C14 C1 C2 C3 -128.0(2) . . . . ? Se1 C1 C2 C3 -3.7(3) . . . . ? C15 C1 C2 C7 -58.2(2) . . . . ? C14 C1 C2 C7 55.1(2) . . . . ? Se1 C1 C2 C7 179.48(15) . . . . ? C7 C2 C3 C4 -0.4(3) . . . . ? C1 C2 C3 C4 -177.0(2) . . . . ? C2 C3 C4 C5 -0.1(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? C5 C6 C7 C2 -0.4(3) . . . . ? C5 C6 C7 C8 175.5(2) . . . . ? C3 C2 C7 C6 0.6(3) . . . . ? C1 C2 C7 C6 177.8(2) . . . . ? C3 C2 C7 C8 -175.7(2) . . . . ? C1 C2 C7 C8 1.4(3) . . . . ? C6 C7 C8 C20 -119.8(2) . . . . ? C2 C7 C8 C20 56.3(2) . . . . ? C6 C7 C8 C9 127.7(2) . . . . ? C2 C7 C8 C9 -56.2(2) . . . . ? C20 C8 C9 C10 125.5(2) . . . . ? C7 C8 C9 C10 -124.5(2) . . . . ? C20 C8 C9 C14 -56.6(2) . . . . ? C7 C8 C9 C14 53.4(2) . . . . ? C14 C9 C10 C11 -1.2(3) . . . . ? C8 C9 C10 C11 176.5(2) . . . . ? C9 C10 C11 C12 -1.2(3) . . . . ? C10 C11 C12 C13 1.6(4) . . . . ? C11 C12 C13 C14 0.4(4) . . . . ? C12 C13 C14 C9 -2.9(3) . . . . ? C12 C13 C14 C1 179.3(2) . . . . ? C10 C9 C14 C13 3.3(3) . . . . ? C8 C9 C14 C13 -174.7(2) . . . . ? C10 C9 C14 C1 -178.6(2) . . . . ? C8 C9 C14 C1 3.4(3) . . . . ? C15 C1 C14 C13 -130.5(2) . . . . ? C2 C1 C14 C13 119.8(2) . . . . ? Se1 C1 C14 C13 -1.4(3) . . . . ? C15 C1 C14 C9 51.5(2) . . . . ? C2 C1 C14 C9 -58.2(2) . . . . ? Se1 C1 C14 C9 -179.35(15) . . . . ? C14 C1 C15 C16 132.6(2) . . . . ? C2 C1 C15 C16 -116.4(2) . . . . ? Se1 C1 C15 C16 3.0(3) . . . . ? C14 C1 C15 C20 -53.6(2) . . . . ? C2 C1 C15 C20 57.5(2) . . . . ? Se1 C1 C15 C20 176.84(15) . . . . ? C20 C15 C16 C17 -0.2(3) . . . . ? C1 C15 C16 C17 173.2(2) . . . . ? C15 C16 C17 C18 0.5(3) . . . . ? C16 C17 C18 C19 -0.7(4) . . . . ? C17 C18 C19 C20 0.4(4) . . . . ? C18 C19 C20 C15 -0.1(3) . . . . ? C18 C19 C20 C8 -174.1(2) . . . . ? C16 C15 C20 C19 0.0(3) . . . . ? C1 C15 C20 C19 -174.4(2) . . . . ? C16 C15 C20 C8 174.6(2) . . . . ? C1 C15 C20 C8 0.3(3) . . . . ? C9 C8 C20 C19 -131.3(2) . . . . ? C7 C8 C20 C19 117.1(2) . . . . ? C9 C8 C20 C15 54.4(2) . . . . ? C7 C8 C20 C15 -57.2(2) . . . . ? C1 Se1 C21 C26 9.5(2) . . . . ? C1 Se1 C21 C22 -175.02(17) . . . . ? C26 C21 C22 C23 0.8(3) . . . . ? Se1 C21 C22 C23 -175.07(18) . . . . ? C21 C22 C23 C24 -1.3(4) . . . . ? C22 C23 C24 N1 -177.0(2) . . . . ? C22 C23 C24 C25 1.2(3) . . . . ? N1 C24 C25 C26 177.5(2) . . . . ? C23 C24 C25 C26 -0.7(3) . . . . ? C22 C21 C26 C25 -0.4(4) . . . . ? Se1 C21 C26 C25 174.99(18) . . . . ? C24 C25 C26 C21 0.3(4) . . . . ? C23 C24 N1 C28 -162.9(2) . . . . ? C25 C24 N1 C28 19.0(4) . . . . ? C23 C24 N1 C27 -16.2(4) . . . . ? C25 C24 N1 C27 165.8(2) . . . . ? C49 Se2 C29 C42 -72.46(18) . . . . ? C49 Se2 C29 C43 53.17(18) . . . . ? C49 Se2 C29 C30 170.23(14) . . . . ? C42 C29 C30 C31 -124.4(2) . . . . ? C43 C29 C30 C31 124.1(2) . . . . ? Se2 C29 C30 C31 0.1(3) . . . . ? C42 C29 C30 C35 55.8(2) . . . . ? C43 C29 C30 C35 -55.6(2) . . . . ? Se2 C29 C30 C35 -179.60(16) . . . . ? C35 C30 C31 C32 1.2(3) . . . . ? C29 C30 C31 C32 -178.5(2) . . . . ? C30 C31 C32 C33 0.2(4) . . . . ? C31 C32 C33 C34 -1.5(4) . . . . ? C32 C33 C34 C35 1.3(4) . . . . ? C33 C34 C35 C30 0.1(4) . . . . ? C33 C34 C35 C36 178.3(2) . . . . ? C31 C30 C35 C34 -1.4(3) . . . . ? C29 C30 C35 C34 178.4(2) . . . . ? C31 C30 C35 C36 -179.8(2) . . . . ? C29 C30 C35 C36 0.0(3) . . . . ? C34 C35 C36 C48 -122.3(2) . . . . ? C30 C35 C36 C48 56.0(2) . . . . ? C34 C35 C36 C37 126.1(2) . . . . ? C30 C35 C36 C37 -55.5(2) . . . . ? C48 C36 C37 C38 123.8(2) . . . . ? C35 C36 C37 C38 -124.3(2) . . . . ? C48 C36 C37 C42 -57.4(2) . . . . ? C35 C36 C37 C42 54.5(2) . . . . ? C42 C37 C38 C39 -1.1(3) . . . . ? C36 C37 C38 C39 177.7(2) . . . . ? C37 C38 C39 C40 0.1(3) . . . . ? C38 C39 C40 C41 0.2(4) . . . . ? C39 C40 C41 C42 0.5(3) . . . . ? C40 C41 C42 C37 -1.4(3) . . . . ? C40 C41 C42 C29 179.7(2) . . . . ? C38 C37 C42 C41 1.7(3) . . . . ? C36 C37 C42 C41 -177.2(2) . . . . ? C38 C37 C42 C29 -179.2(2) . . . . ? C36 C37 C42 C29 1.9(3) . . . . ? C43 C29 C42 C41 -127.2(2) . . . . ? C30 C29 C42 C41 122.1(2) . . . . ? Se2 C29 C42 C41 3.3(3) . . . . ? C43 C29 C42 C37 53.9(2) . . . . ? C30 C29 C42 C37 -56.8(2) . . . . ? Se2 C29 C42 C37 -175.68(16) . . . . ? C42 C29 C43 C44 126.1(2) . . . . ? C30 C29 C43 C44 -123.2(2) . . . . ? Se2 C29 C43 C44 -4.7(3) . . . . ? C42 C29 C43 C48 -54.6(2) . . . . ? C30 C29 C43 C48 56.1(2) . . . . ? Se2 C29 C43 C48 174.64(16) . . . . ? C48 C43 C44 C45 1.2(3) . . . . ? C29 C43 C44 C45 -179.5(2) . . . . ? C43 C44 C45 C46 -0.9(3) . . . . ? C44 C45 C46 C47 0.0(4) . . . . ? C45 C46 C47 C48 0.5(4) . . . . ? C46 C47 C48 C43 -0.2(3) . . . . ? C46 C47 C48 C36 -179.5(2) . . . . ? C44 C43 C48 C47 -0.7(3) . . . . ? C29 C43 C48 C47 179.9(2) . . . . ? C44 C43 C48 C36 178.6(2) . . . . ? C29 C43 C48 C36 -0.7(3) . . . . ? C37 C36 C48 C47 -124.1(2) . . . . ? C35 C36 C48 C47 123.8(2) . . . . ? C37 C36 C48 C43 56.5(2) . . . . ? C35 C36 C48 C43 -55.5(2) . . . . ? C29 Se2 C49 C50 -154.65(18) . . . . ? C29 Se2 C49 C54 28.3(2) . . . . ? C50 C49 C54 C53 -0.3(4) . . . . ? Se2 C49 C54 C53 176.7(2) . . . . ? C49 C54 C53 C52 -1.2(4) . . . . ? C54 C53 C52 C51 1.6(4) . . . . ? C54 C53 C52 N2 178.1(3) . . . . ? C53 C52 C51 C50 -0.4(4) . . . . ? N2 C52 C51 C50 -176.8(3) . . . . ? C54 C49 C50 C51 1.6(4) . . . . ? Se2 C49 C50 C51 -175.8(2) . . . . ? C52 C51 C50 C49 -1.2(4) . . . . ? C51 C52 N2 C56 -136.5(3) . . . . ? C53 C52 N2 C56 47.1(5) . . . . ? C51 C52 N2 C55 9.9(5) . . . . ? C53 C52 N2 C55 -166.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.924 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.924 _refine_diff_density_max 1.008 _refine_diff_density_min -0.707 _refine_diff_density_rms 0.085 # Attachment '1c_Se_OMe_Rev.cif' data_1c_wn002 _database_code_depnum_ccdc_archive 'CCDC 704858' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H20 O Se' _chemical_formula_weight 439.39 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)/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 11.5331(11) _cell_length_b 14.2581(14) _cell_length_c 12.4437(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.798(1) _cell_angle_gamma 90.00 _cell_volume 2045.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 233 _cell_measurement_reflns_used 4998 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 28.16 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 1.851 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4579 _exptl_absorpt_correction_T_max 0.7084 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 233 _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 APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 11209 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4570 _reflns_number_gt 3925 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0416P)^2^+0.4839P] 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 4570 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0365 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0772 _refine_ls_wR_factor_gt 0.0732 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.402006(15) 0.109206(13) 0.063719(15) 0.01736(7) Uani 1 1 d . . . C1 C 0.30056(15) 0.18294(12) 0.15483(14) 0.0146(4) Uani 1 1 d . . . C2 C 0.35729(15) 0.19150(13) 0.26838(15) 0.0162(4) Uani 1 1 d . . . C3 C 0.46263(16) 0.15400(13) 0.30513(16) 0.0198(4) Uani 1 1 d . . . H3A H 0.5077 0.1177 0.2592 0.024 Uiso 1 1 calc R . . C4 C 0.50061(17) 0.17094(15) 0.41124(16) 0.0245(4) Uani 1 1 d . . . H4A H 0.5713 0.1453 0.4368 0.029 Uiso 1 1 calc R . . C5 C 0.43544(18) 0.22492(15) 0.47894(16) 0.0257(5) Uani 1 1 d . . . H5A H 0.4625 0.2367 0.5497 0.031 Uiso 1 1 calc R . . C6 C 0.32925(17) 0.26212(14) 0.44221(16) 0.0223(4) Uani 1 1 d . . . H6A H 0.2848 0.2991 0.4880 0.027 Uiso 1 1 calc R . . C7 C 0.28994(16) 0.24410(13) 0.33794(15) 0.0177(4) Uani 1 1 d . . . C8 C 0.17640(16) 0.27919(13) 0.28639(15) 0.0163(4) Uani 1 1 d . . . H8A H 0.1291 0.3157 0.3366 0.020 Uiso 1 1 calc R . . C9 C 0.21185(15) 0.33574(13) 0.18922(14) 0.0155(4) Uani 1 1 d . . . C10 C 0.18725(15) 0.42970(13) 0.17075(15) 0.0178(4) Uani 1 1 d . . . H10A H 0.1423 0.4635 0.2191 0.021 Uiso 1 1 calc R . . C11 C 0.22964(16) 0.47365(13) 0.08006(15) 0.0194(4) Uani 1 1 d . . . H11A H 0.2125 0.5371 0.0664 0.023 Uiso 1 1 calc R . . C12 C 0.29727(16) 0.42342(14) 0.00991(15) 0.0182(4) Uani 1 1 d . . . H12A H 0.3264 0.4532 -0.0510 0.022 Uiso 1 1 calc R . . C13 C 0.32244(15) 0.32902(13) 0.02913(15) 0.0155(4) Uani 1 1 d . . . H13A H 0.3686 0.2955 -0.0185 0.019 Uiso 1 1 calc R . . C14 C 0.27939(15) 0.28503(12) 0.11835(14) 0.0145(4) Uani 1 1 d . . . C15 C 0.18024(15) 0.13987(13) 0.17226(15) 0.0161(4) Uani 1 1 d . . . C16 C 0.13554(17) 0.05764(14) 0.12818(16) 0.0216(4) Uani 1 1 d . . . H16A H 0.1808 0.0208 0.0830 0.026 Uiso 1 1 calc R . . C17 C 0.02325(18) 0.03002(15) 0.15118(17) 0.0269(5) Uani 1 1 d . . . H17A H -0.0071 -0.0258 0.1217 0.032 Uiso 1 1 calc R . . C18 C -0.04386(18) 0.08417(16) 0.21709(17) 0.0271(5) Uani 1 1 d . . . H18A H -0.1202 0.0657 0.2308 0.033 Uiso 1 1 calc R . . C19 C 0.00122(17) 0.16624(15) 0.26342(16) 0.0226(4) Uani 1 1 d . . . H19A H -0.0442 0.2029 0.3088 0.027 Uiso 1 1 calc R . . C20 C 0.11371(16) 0.19298(13) 0.24170(14) 0.0173(4) Uani 1 1 d . . . C21 C 0.32968(16) 0.11620(12) -0.07739(15) 0.0149(4) Uani 1 1 d . . . C22 C 0.39702(16) 0.08367(13) -0.16043(16) 0.0181(4) Uani 1 1 d . . . H22A H 0.4716 0.0597 -0.1446 0.022 Uiso 1 1 calc R . . C23 C 0.35579(16) 0.08609(13) -0.26570(16) 0.0187(4) Uani 1 1 d . . . H23A H 0.4018 0.0634 -0.3211 0.022 Uiso 1 1 calc R . . C24 C 0.24557(16) 0.12240(12) -0.28970(15) 0.0158(4) Uani 1 1 d . . . C25 C 0.17758(15) 0.15482(13) -0.20749(15) 0.0163(4) Uani 1 1 d . . . H25A H 0.1031 0.1789 -0.2234 0.020 Uiso 1 1 calc R . . C26 C 0.21946(16) 0.15177(13) -0.10151(15) 0.0170(4) Uani 1 1 d . . . H26A H 0.1732 0.1738 -0.0460 0.020 Uiso 1 1 calc R . . O1 O 0.21245(12) 0.12190(9) -0.39594(11) 0.0206(3) Uani 1 1 d . . . C27 C 0.09588(17) 0.14858(16) -0.42285(17) 0.0260(5) Uani 1 1 d . . . H27A H 0.0428 0.1096 -0.3836 0.039 Uiso 1 1 calc R . . H27B H 0.0812 0.1405 -0.4995 0.039 Uiso 1 1 calc R . . H27C H 0.0844 0.2138 -0.4038 0.039 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 0.01743(11) 0.01635(11) 0.01806(11) 0.00045(7) -0.00323(7) 0.00441(7) C1 0.0148(8) 0.0142(9) 0.0147(9) 0.0009(7) -0.0013(7) 0.0002(7) C2 0.0170(9) 0.0155(9) 0.0158(9) 0.0046(7) -0.0031(7) -0.0047(7) C3 0.0193(9) 0.0174(10) 0.0225(10) 0.0059(8) -0.0041(8) -0.0047(8) C4 0.0202(10) 0.0263(11) 0.0262(11) 0.0108(9) -0.0099(8) -0.0076(8) C5 0.0296(11) 0.0302(11) 0.0168(10) 0.0054(8) -0.0074(8) -0.0120(9) C6 0.0281(11) 0.0233(10) 0.0153(10) 0.0012(8) -0.0008(8) -0.0084(8) C7 0.0206(9) 0.0155(9) 0.0168(9) 0.0034(7) -0.0014(8) -0.0063(7) C8 0.0183(9) 0.0166(9) 0.0142(9) 0.0011(7) 0.0021(7) -0.0003(7) C9 0.0158(8) 0.0163(9) 0.0142(9) 0.0014(7) -0.0022(7) -0.0015(7) C10 0.0183(9) 0.0159(9) 0.0193(10) -0.0030(7) 0.0006(8) 0.0010(7) C11 0.0218(9) 0.0141(9) 0.0221(10) 0.0015(8) -0.0028(8) 0.0011(7) C12 0.0184(9) 0.0186(9) 0.0176(9) 0.0030(7) -0.0009(7) -0.0024(7) C13 0.0139(8) 0.0172(9) 0.0152(9) 0.0001(7) -0.0009(7) 0.0000(7) C14 0.0136(8) 0.0138(9) 0.0157(9) 0.0004(7) -0.0043(7) -0.0013(7) C15 0.0172(9) 0.0168(9) 0.0142(9) 0.0053(7) -0.0028(7) -0.0014(7) C16 0.0265(10) 0.0198(10) 0.0182(10) 0.0024(8) -0.0031(8) -0.0034(8) C17 0.0307(11) 0.0248(11) 0.0249(11) 0.0025(9) -0.0032(9) -0.0130(9) C18 0.0229(10) 0.0350(12) 0.0234(11) 0.0060(9) -0.0001(9) -0.0134(9) C19 0.0214(10) 0.0294(11) 0.0172(10) 0.0059(8) 0.0021(8) -0.0029(8) C20 0.0200(9) 0.0194(9) 0.0123(9) 0.0064(7) -0.0016(7) -0.0019(7) C21 0.0169(9) 0.0113(9) 0.0164(9) 0.0008(7) -0.0020(7) -0.0008(7) C22 0.0145(9) 0.0155(9) 0.0242(10) 0.0015(8) -0.0004(8) 0.0033(7) C23 0.0179(9) 0.0180(9) 0.0205(10) -0.0030(8) 0.0047(8) 0.0034(7) C24 0.0185(9) 0.0120(9) 0.0168(9) 0.0000(7) -0.0013(7) -0.0014(7) C25 0.0139(8) 0.0147(9) 0.0204(9) -0.0004(7) -0.0012(7) 0.0007(7) C26 0.0170(9) 0.0166(9) 0.0173(9) -0.0014(7) 0.0007(7) 0.0022(7) O1 0.0208(7) 0.0243(8) 0.0166(7) -0.0026(5) -0.0018(5) 0.0043(6) C27 0.0249(10) 0.0326(12) 0.0199(10) -0.0018(9) -0.0073(8) 0.0090(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 Se1 C21 1.9228(19) . ? Se1 C1 1.9603(18) . ? C1 C15 1.539(2) . ? C1 C14 1.542(2) . ? C1 C2 1.543(2) . ? C2 C3 1.391(3) . ? C2 C7 1.399(3) . ? C3 C4 1.399(3) . ? C3 H3A 0.9400 . ? C4 C5 1.381(3) . ? C4 H4A 0.9400 . ? C5 C6 1.398(3) . ? C5 H5A 0.9400 . ? C6 C7 1.385(3) . ? C6 H6A 0.9400 . ? C7 C8 1.524(3) . ? C8 C9 1.520(2) . ? C8 C20 1.522(3) . ? C8 H8A 0.9900 . ? C9 C10 1.387(3) . ? C9 C14 1.396(3) . ? C10 C11 1.393(3) . ? C10 H10A 0.9400 . ? C11 C12 1.388(3) . ? C11 H11A 0.9400 . ? C12 C13 1.396(3) . ? C12 H12A 0.9400 . ? C13 C14 1.381(3) . ? C13 H13A 0.9400 . ? C15 C16 1.387(3) . ? C15 C20 1.397(3) . ? C16 C17 1.392(3) . ? C16 H16A 0.9400 . ? C17 C18 1.381(3) . ? C17 H17A 0.9400 . ? C18 C19 1.398(3) . ? C18 H18A 0.9400 . ? C19 C20 1.387(3) . ? C19 H19A 0.9400 . ? C21 C22 1.391(3) . ? C21 C26 1.393(2) . ? C22 C23 1.380(3) . ? C22 H22A 0.9400 . ? C23 C24 1.396(3) . ? C23 H23A 0.9400 . ? C24 O1 1.365(2) . ? C24 C25 1.388(3) . ? C25 C26 1.391(3) . ? C25 H25A 0.9400 . ? C26 H26A 0.9400 . ? O1 C27 1.427(2) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C27 H27C 0.9700 . ? 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 C21 Se1 C1 104.52(7) . . ? C15 C1 C14 106.44(14) . . ? C15 C1 C2 105.11(14) . . ? C14 C1 C2 104.69(14) . . ? C15 C1 Se1 115.13(13) . . ? C14 C1 Se1 115.34(12) . . ? C2 C1 Se1 109.17(12) . . ? C3 C2 C7 119.91(17) . . ? C3 C2 C1 127.68(17) . . ? C7 C2 C1 112.41(15) . . ? C2 C3 C4 119.22(19) . . ? C2 C3 H3A 120.4 . . ? C4 C3 H3A 120.4 . . ? C5 C4 C3 120.78(18) . . ? C5 C4 H4A 119.6 . . ? C3 C4 H4A 119.6 . . ? C4 C5 C6 120.00(19) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 120.0 . . ? C7 C6 C5 119.6(2) . . ? C7 C6 H6A 120.2 . . ? C5 C6 H6A 120.2 . . ? C6 C7 C2 120.48(18) . . ? C6 C7 C8 125.80(18) . . ? C2 C7 C8 113.69(16) . . ? C9 C8 C20 105.91(15) . . ? C9 C8 C7 105.06(15) . . ? C20 C8 C7 106.29(15) . . ? C9 C8 H8A 113.0 . . ? C20 C8 H8A 113.0 . . ? C7 C8 H8A 113.0 . . ? C10 C9 C14 120.71(16) . . ? C10 C9 C8 125.83(17) . . ? C14 C9 C8 113.39(16) . . ? C9 C10 C11 119.58(17) . . ? C9 C10 H10A 120.2 . . ? C11 C10 H10A 120.2 . . ? C12 C11 C10 119.74(17) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? C11 C12 C13 120.51(17) . . ? C11 C12 H12A 119.7 . . ? C13 C12 H12A 119.7 . . ? C14 C13 C12 119.84(17) . . ? C14 C13 H13A 120.1 . . ? C12 C13 H13A 120.1 . . ? C13 C14 C9 119.62(16) . . ? C13 C14 C1 127.43(16) . . ? C9 C14 C1 112.91(15) . . ? C16 C15 C20 119.90(17) . . ? C16 C15 C1 127.38(17) . . ? C20 C15 C1 112.72(16) . . ? C15 C16 C17 119.64(19) . . ? C15 C16 H16A 120.2 . . ? C17 C16 H16A 120.2 . . ? C18 C17 C16 120.41(19) . . ? C18 C17 H17A 119.8 . . ? C16 C17 H17A 119.8 . . ? C17 C18 C19 120.32(19) . . ? C17 C18 H18A 119.8 . . ? C19 C18 H18A 119.8 . . ? C20 C19 C18 119.21(19) . . ? C20 C19 H19A 120.4 . . ? C18 C19 H19A 120.4 . . ? C19 C20 C15 120.46(18) . . ? C19 C20 C8 125.96(18) . . ? C15 C20 C8 113.58(16) . . ? C22 C21 C26 119.23(17) . . ? C22 C21 Se1 115.12(13) . . ? C26 C21 Se1 125.63(14) . . ? C23 C22 C21 120.86(17) . . ? C23 C22 H22A 119.6 . . ? C21 C22 H22A 119.6 . . ? C22 C23 C24 119.77(17) . . ? C22 C23 H23A 120.1 . . ? C24 C23 H23A 120.1 . . ? O1 C24 C25 124.65(16) . . ? O1 C24 C23 115.51(17) . . ? C25 C24 C23 119.84(18) . . ? C24 C25 C26 120.08(17) . . ? C24 C25 H25A 120.0 . . ? C26 C25 H25A 120.0 . . ? C25 C26 C21 120.22(17) . . ? C25 C26 H26A 119.9 . . ? C21 C26 H26A 119.9 . . ? C24 O1 C27 117.32(15) . . ? O1 C27 H27A 109.5 . . ? O1 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O1 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 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 C21 Se1 C1 C15 68.28(14) . . . . ? C21 Se1 C1 C14 -56.32(14) . . . . ? C21 Se1 C1 C2 -173.82(11) . . . . ? C15 C1 C2 C3 123.60(19) . . . . ? C14 C1 C2 C3 -124.45(19) . . . . ? Se1 C1 C2 C3 -0.4(2) . . . . ? C15 C1 C2 C7 -56.45(19) . . . . ? C14 C1 C2 C7 55.50(19) . . . . ? Se1 C1 C2 C7 179.52(12) . . . . ? C7 C2 C3 C4 -1.0(3) . . . . ? C1 C2 C3 C4 178.89(17) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C3 C4 C5 C6 1.0(3) . . . . ? C4 C5 C6 C7 0.3(3) . . . . ? C5 C6 C7 C2 -2.0(3) . . . . ? C5 C6 C7 C8 179.80(18) . . . . ? C3 C2 C7 C6 2.4(3) . . . . ? C1 C2 C7 C6 -177.58(16) . . . . ? C3 C2 C7 C8 -179.20(16) . . . . ? C1 C2 C7 C8 0.9(2) . . . . ? C6 C7 C8 C9 121.3(2) . . . . ? C2 C7 C8 C9 -57.07(19) . . . . ? C6 C7 C8 C20 -126.74(19) . . . . ? C2 C7 C8 C20 54.9(2) . . . . ? C20 C8 C9 C10 126.75(19) . . . . ? C7 C8 C9 C10 -120.99(19) . . . . ? C20 C8 C9 C14 -56.30(19) . . . . ? C7 C8 C9 C14 55.96(19) . . . . ? C14 C9 C10 C11 0.5(3) . . . . ? C8 C9 C10 C11 177.26(17) . . . . ? C9 C10 C11 C12 -0.9(3) . . . . ? C10 C11 C12 C13 0.5(3) . . . . ? C11 C12 C13 C14 0.3(3) . . . . ? C12 C13 C14 C9 -0.6(3) . . . . ? C12 C13 C14 C1 -177.98(16) . . . . ? C10 C9 C14 C13 0.2(3) . . . . ? C8 C9 C14 C13 -176.91(16) . . . . ? C10 C9 C14 C1 177.95(16) . . . . ? C8 C9 C14 C1 0.8(2) . . . . ? C15 C1 C14 C13 -128.20(18) . . . . ? C2 C1 C14 C13 120.80(19) . . . . ? Se1 C1 C14 C13 0.8(2) . . . . ? C15 C1 C14 C9 54.28(19) . . . . ? C2 C1 C14 C9 -56.72(19) . . . . ? Se1 C1 C14 C9 -176.70(12) . . . . ? C14 C1 C15 C16 126.79(19) . . . . ? C2 C1 C15 C16 -122.5(2) . . . . ? Se1 C1 C15 C16 -2.4(2) . . . . ? C14 C1 C15 C20 -53.68(19) . . . . ? C2 C1 C15 C20 57.02(19) . . . . ? Se1 C1 C15 C20 177.18(12) . . . . ? C20 C15 C16 C17 1.8(3) . . . . ? C1 C15 C16 C17 -178.70(18) . . . . ? C15 C16 C17 C18 0.3(3) . . . . ? C16 C17 C18 C19 -1.5(3) . . . . ? C17 C18 C19 C20 0.5(3) . . . . ? C18 C19 C20 C15 1.6(3) . . . . ? C18 C19 C20 C8 -179.20(18) . . . . ? C16 C15 C20 C19 -2.8(3) . . . . ? C1 C15 C20 C19 177.67(16) . . . . ? C16 C15 C20 C8 177.93(16) . . . . ? C1 C15 C20 C8 -1.6(2) . . . . ? C9 C8 C20 C19 -122.34(19) . . . . ? C7 C8 C20 C19 126.26(19) . . . . ? C9 C8 C20 C15 56.92(19) . . . . ? C7 C8 C20 C15 -54.48(19) . . . . ? C1 Se1 C21 C22 168.52(13) . . . . ? C1 Se1 C21 C26 -10.32(18) . . . . ? C26 C21 C22 C23 -0.2(3) . . . . ? Se1 C21 C22 C23 -179.08(14) . . . . ? C21 C22 C23 C24 0.6(3) . . . . ? C22 C23 C24 O1 179.95(16) . . . . ? C22 C23 C24 C25 -0.7(3) . . . . ? O1 C24 C25 C26 179.68(17) . . . . ? C23 C24 C25 C26 0.4(3) . . . . ? C24 C25 C26 C21 0.0(3) . . . . ? C22 C21 C26 C25 -0.1(3) . . . . ? Se1 C21 C26 C25 178.65(14) . . . . ? C25 C24 O1 C27 -6.1(3) . . . . ? C23 C24 O1 C27 173.21(17) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.316 _refine_diff_density_min -0.492 _refine_diff_density_rms 0.082 # Attachment '1d_SeCl_Rev.cif' data_1d_wn003 _database_code_depnum_ccdc_archive 'CCDC 704859' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H17 Cl Se' _chemical_formula_weight 443.81 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 11.8868(6) _cell_length_b 13.9067(7) _cell_length_c 22.8836(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3782.8(3) _cell_formula_units_Z 8 _cell_measurement_temperature 233 _cell_measurement_reflns_used 7272 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.16 _exptl_crystal_description Plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 2.135 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5667 _exptl_absorpt_correction_T_max 0.6747 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 233 _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 APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 19832 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4302 _reflns_number_gt 3644 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0500P)^2^+0.6888P] 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 4302 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0369 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0733 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _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 0.186158(18) 0.071636(15) 0.005031(8) 0.01975(8) Uani 1 1 d . . . C1 C 0.21874(16) 0.09935(14) -0.07721(8) 0.0146(4) Uani 1 1 d . . . C2 C 0.16765(15) 0.01759(14) -0.11447(8) 0.0145(4) Uani 1 1 d . . . C3 C 0.10779(16) -0.06176(14) -0.09529(9) 0.0181(4) Uani 1 1 d . . . H3A H 0.0947 -0.0708 -0.0552 0.022 Uiso 1 1 calc R . . C4 C 0.06683(16) -0.12833(14) -0.13580(9) 0.0200(4) Uani 1 1 d . . . H4A H 0.0270 -0.1827 -0.1227 0.024 Uiso 1 1 calc R . . C5 C 0.08441(16) -0.11481(15) -0.19483(9) 0.0210(4) Uani 1 1 d . . . H5A H 0.0558 -0.1596 -0.2218 0.025 Uiso 1 1 calc R . . C6 C 0.14442(16) -0.03493(14) -0.21476(9) 0.0184(4) Uani 1 1 d . . . H6A H 0.1565 -0.0258 -0.2550 0.022 Uiso 1 1 calc R . . C7 C 0.18594(15) 0.03078(14) -0.17450(8) 0.0149(4) Uani 1 1 d . . . C8 C 0.25172(15) 0.12179(14) -0.18879(8) 0.0151(4) Uani 1 1 d . . . H8A H 0.2644 0.1305 -0.2312 0.018 Uiso 1 1 calc R . . C9 C 0.18514(15) 0.20366(14) -0.16153(8) 0.0154(4) Uani 1 1 d . . . C10 C 0.14286(16) 0.28275(14) -0.19087(9) 0.0184(4) Uani 1 1 d . . . H10A H 0.1545 0.2895 -0.2313 0.022 Uiso 1 1 calc R . . C11 C 0.08248(16) 0.35269(14) -0.15990(9) 0.0215(4) Uani 1 1 d . . . H11A H 0.0542 0.4070 -0.1794 0.026 Uiso 1 1 calc R . . C12 C 0.06472(16) 0.34151(14) -0.10066(9) 0.0205(4) Uani 1 1 d . . . H12A H 0.0246 0.3888 -0.0800 0.025 Uiso 1 1 calc R . . C13 C 0.10550(15) 0.26105(14) -0.07099(9) 0.0170(4) Uani 1 1 d . . . H13A H 0.0917 0.2535 -0.0308 0.020 Uiso 1 1 calc R . . C14 C 0.16662(15) 0.19225(14) -0.10144(8) 0.0142(4) Uani 1 1 d . . . C15 C 0.34435(16) 0.10165(14) -0.09399(9) 0.0156(4) Uani 1 1 d . . . C16 C 0.43603(17) 0.09101(13) -0.05708(9) 0.0192(4) Uani 1 1 d . . . H16A H 0.4253 0.0820 -0.0168 0.023 Uiso 1 1 calc R . . C17 C 0.54455(17) 0.09379(14) -0.08048(10) 0.0223(4) Uani 1 1 d . . . H17A H 0.6072 0.0870 -0.0557 0.027 Uiso 1 1 calc R . . C18 C 0.56028(16) 0.10643(15) -0.13981(10) 0.0224(4) Uani 1 1 d . . . H18A H 0.6337 0.1081 -0.1551 0.027 Uiso 1 1 calc R . . C19 C 0.46901(16) 0.11671(14) -0.17706(9) 0.0192(4) Uani 1 1 d . . . H19A H 0.4802 0.1250 -0.2174 0.023 Uiso 1 1 calc R . . C20 C 0.36075(15) 0.11461(13) -0.15404(8) 0.0155(4) Uani 1 1 d . . . C21 C 0.25600(15) 0.17353(13) 0.04817(8) 0.0165(4) Uani 1 1 d . . . C22 C 0.25122(16) 0.16293(14) 0.10884(9) 0.0187(4) Uani 1 1 d . . . H22A H 0.2180 0.1078 0.1251 0.022 Uiso 1 1 calc R . . C23 C 0.29523(16) 0.23334(15) 0.14512(9) 0.0186(4) Uani 1 1 d . . . H23A H 0.2921 0.2263 0.1859 0.022 Uiso 1 1 calc R . . C24 C 0.34395(15) 0.31417(14) 0.12038(8) 0.0160(4) Uani 1 1 d . . . C25 C 0.35231(16) 0.32428(14) 0.06048(8) 0.0156(4) Uani 1 1 d . . . H25A H 0.3879 0.3786 0.0445 0.019 Uiso 1 1 calc R . . C26 C 0.30803(15) 0.25405(15) 0.02400(9) 0.0172(4) Uani 1 1 d . . . H26A H 0.3131 0.2608 -0.0168 0.021 Uiso 1 1 calc R . . Cl1 Cl 0.39610(4) 0.40586(4) 0.16461(2) 0.02175(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.02675(14) 0.01791(13) 0.01460(12) 0.00137(7) 0.00036(8) -0.00747(8) C1 0.0163(9) 0.0137(9) 0.0138(9) 0.0009(7) 0.0001(7) -0.0009(7) C2 0.0113(9) 0.0143(9) 0.0179(10) 0.0000(7) -0.0034(7) 0.0018(7) C3 0.0180(10) 0.0183(10) 0.0181(10) 0.0019(8) -0.0021(8) 0.0002(8) C4 0.0177(10) 0.0147(10) 0.0277(11) 0.0016(8) -0.0036(8) -0.0012(8) C5 0.0182(10) 0.0191(10) 0.0258(11) -0.0062(8) -0.0054(8) 0.0003(8) C6 0.0157(9) 0.0199(10) 0.0195(10) -0.0014(8) -0.0032(7) 0.0042(8) C7 0.0112(8) 0.0152(10) 0.0184(10) 0.0007(8) -0.0013(7) 0.0029(7) C8 0.0134(9) 0.0171(9) 0.0148(9) 0.0011(7) 0.0002(7) 0.0013(7) C9 0.0110(9) 0.0163(10) 0.0190(10) 0.0007(7) -0.0011(7) -0.0015(7) C10 0.0152(9) 0.0193(10) 0.0208(10) 0.0046(8) 0.0004(7) -0.0019(8) C11 0.0158(9) 0.0158(10) 0.0328(12) 0.0042(8) -0.0027(8) -0.0004(8) C12 0.0145(9) 0.0149(9) 0.0321(11) -0.0056(8) -0.0010(8) 0.0010(8) C13 0.0114(8) 0.0181(10) 0.0216(10) -0.0030(8) 0.0024(7) -0.0025(7) C14 0.0113(9) 0.0136(9) 0.0178(9) 0.0005(7) -0.0003(7) -0.0028(7) C15 0.0151(9) 0.0116(9) 0.0201(10) -0.0018(7) -0.0008(7) 0.0006(7) C16 0.0212(10) 0.0143(9) 0.0221(10) -0.0019(8) -0.0038(8) 0.0002(8) C17 0.0147(10) 0.0192(10) 0.0330(12) -0.0043(9) -0.0081(8) 0.0006(8) C18 0.0122(9) 0.0188(10) 0.0362(12) -0.0067(9) 0.0017(8) -0.0006(8) C19 0.0173(9) 0.0159(10) 0.0244(10) -0.0047(8) 0.0028(8) -0.0015(8) C20 0.0134(9) 0.0123(9) 0.0208(10) -0.0016(7) -0.0011(8) 0.0002(7) C21 0.0171(10) 0.0162(10) 0.0161(9) -0.0013(7) -0.0019(7) -0.0007(8) C22 0.0186(10) 0.0187(10) 0.0188(10) 0.0031(8) 0.0029(8) -0.0008(8) C23 0.0185(9) 0.0241(11) 0.0132(9) 0.0004(8) 0.0020(7) 0.0017(8) C24 0.0119(9) 0.0179(10) 0.0182(9) -0.0047(8) -0.0018(7) 0.0016(7) C25 0.0149(9) 0.0137(9) 0.0183(9) 0.0025(7) -0.0005(7) 0.0006(7) C26 0.0190(9) 0.0193(10) 0.0134(9) 0.0019(8) -0.0004(7) 0.0008(8) Cl1 0.0207(2) 0.0261(3) 0.0184(2) -0.00542(19) 0.00029(18) -0.0052(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 C21 1.9162(19) . ? Se1 C1 1.9598(19) . ? C1 C14 1.536(3) . ? C1 C15 1.542(3) . ? C1 C2 1.546(3) . ? C2 C3 1.384(3) . ? C2 C7 1.403(3) . ? C3 C4 1.398(3) . ? C3 H3A 0.9400 . ? C4 C5 1.380(3) . ? C4 H4A 0.9400 . ? C5 C6 1.397(3) . ? C5 H5A 0.9400 . ? C6 C7 1.388(3) . ? C6 H6A 0.9400 . ? C7 C8 1.523(3) . ? C8 C9 1.520(3) . ? C8 C20 1.524(3) . ? C8 H8A 0.9900 . ? C9 C10 1.383(3) . ? C9 C14 1.401(3) . ? C10 C11 1.401(3) . ? C10 H10A 0.9400 . ? C11 C12 1.381(3) . ? C11 H11A 0.9400 . ? C12 C13 1.396(3) . ? C12 H12A 0.9400 . ? C13 C14 1.389(3) . ? C13 H13A 0.9400 . ? C15 C16 1.387(3) . ? C15 C20 1.400(3) . ? C16 C17 1.397(3) . ? C16 H16A 0.9400 . ? C17 C18 1.382(3) . ? C17 H17A 0.9400 . ? C18 C19 1.387(3) . ? C18 H18A 0.9400 . ? C19 C20 1.391(3) . ? C19 H19A 0.9400 . ? C21 C22 1.397(3) . ? C21 C26 1.394(3) . ? C22 H22A 0.9400 . ? C22 C23 1.386(3) . ? C23 H23A 0.9400 . ? C23 C24 1.385(3) . ? C24 C25 1.382(3) . ? C25 C26 1.388(3) . ? C26 H26A 0.9400 . ? C25 H25A 0.9400 . ? C24 Cl1 1.7420(19) . ? 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 C21 Se1 C1 105.29(8) . . ? C14 C1 C15 106.45(15) . . ? C14 C1 C2 105.14(14) . . ? C15 C1 C2 104.98(15) . . ? C14 C1 Se1 115.61(13) . . ? C15 C1 Se1 115.76(13) . . ? C2 C1 Se1 107.90(12) . . ? C3 C2 C7 119.62(18) . . ? C3 C2 C1 127.85(18) . . ? C7 C2 C1 112.52(16) . . ? C2 C3 C4 119.79(19) . . ? C2 C3 H3A 120.1 . . ? C4 C3 H3A 120.1 . . ? C5 C4 C3 120.42(19) . . ? C5 C4 H4A 119.8 . . ? C3 C4 H4A 119.8 . . ? C4 C5 C6 120.35(18) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C7 C6 C5 119.24(19) . . ? C7 C6 H6A 120.4 . . ? C5 C6 H6A 120.4 . . ? C6 C7 C2 120.58(18) . . ? C6 C7 C8 125.94(18) . . ? C2 C7 C8 113.48(16) . . ? C9 C8 C7 105.48(15) . . ? C9 C8 C20 106.12(15) . . ? C7 C8 C20 105.66(15) . . ? C9 C8 H8A 113.0 . . ? C7 C8 H8A 113.0 . . ? C20 C8 H8A 113.0 . . ? C10 C9 C14 120.61(18) . . ? C10 C9 C8 125.82(17) . . ? C14 C9 C8 113.56(17) . . ? C9 C10 C11 119.51(19) . . ? C9 C10 H10A 120.2 . . ? C11 C10 H10A 120.2 . . ? C12 C11 C10 119.78(18) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? C11 C12 C13 120.98(18) . . ? C11 C12 H12A 119.5 . . ? C13 C12 H12A 119.5 . . ? C14 C13 C12 119.33(18) . . ? C14 C13 H13A 120.3 . . ? C12 C13 H13A 120.3 . . ? C13 C14 C9 119.77(18) . . ? C13 C14 C1 127.53(17) . . ? C9 C14 C1 112.70(16) . . ? C16 C15 C20 120.16(18) . . ? C16 C15 C1 127.38(18) . . ? C20 C15 C1 112.45(16) . . ? C15 C16 C17 119.29(19) . . ? C15 C16 H16A 120.4 . . ? C17 C16 H16A 120.4 . . ? C18 C17 C16 120.33(18) . . ? C18 C17 H17A 119.8 . . ? C16 C17 H17A 119.8 . . ? C17 C18 C19 120.73(18) . . ? C17 C18 H18A 119.6 . . ? C19 C18 H18A 119.6 . . ? C18 C19 C20 119.27(19) . . ? C18 C19 H19A 120.4 . . ? C20 C19 H19A 120.4 . . ? C19 C20 C15 120.22(18) . . ? C19 C20 C8 126.02(18) . . ? C15 C20 C8 113.73(16) . . ? C22 C21 C26 119.81(18) . . ? C26 C21 Se1 125.60(15) . . ? C22 C21 Se1 114.59(14) . . ? C25 C26 C21 119.67(18) . . ? C25 C26 H26A 120.2 . . ? C21 C26 H26A 120.2 . . ? C24 C25 C26 119.84(18) . . ? C24 C25 H25A 120.1 . . ? C26 C25 H25A 120.1 . . ? C25 C24 C23 121.21(18) . . ? C25 C24 Cl1 118.45(15) . . ? C23 C24 Cl1 120.35(15) . . ? C24 C23 C22 119.09(18) . . ? C24 C23 H23A 120.5 . . ? C22 C23 H23A 120.5 . . ? C23 C22 C21 120.34(18) . . ? C23 C22 H22A 119.8 . . ? C21 C22 H22A 119.8 . . ? 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 C21 Se1 C1 C14 -64.45(14) . . . . ? C21 Se1 C1 C15 61.00(15) . . . . ? C21 Se1 C1 C2 178.22(12) . . . . ? C14 C1 C2 C3 -123.2(2) . . . . ? C15 C1 C2 C3 124.7(2) . . . . ? Se1 C1 C2 C3 0.7(2) . . . . ? C14 C1 C2 C7 55.83(19) . . . . ? C15 C1 C2 C7 -56.3(2) . . . . ? Se1 C1 C2 C7 179.74(13) . . . . ? C7 C2 C3 C4 0.4(3) . . . . ? C1 C2 C3 C4 179.40(18) . . . . ? C2 C3 C4 C5 -0.8(3) . . . . ? C3 C4 C5 C6 0.7(3) . . . . ? C4 C5 C6 C7 -0.1(3) . . . . ? C5 C6 C7 C2 -0.3(3) . . . . ? C5 C6 C7 C8 -179.33(18) . . . . ? C3 C2 C7 C6 0.1(3) . . . . ? C1 C2 C7 C6 -179.01(16) . . . . ? C3 C2 C7 C8 179.28(16) . . . . ? C1 C2 C7 C8 0.2(2) . . . . ? C6 C7 C8 C9 122.87(19) . . . . ? C2 C7 C8 C9 -56.3(2) . . . . ? C6 C7 C8 C20 -124.99(19) . . . . ? C2 C7 C8 C20 55.9(2) . . . . ? C7 C8 C9 C10 -122.7(2) . . . . ? C20 C8 C9 C10 125.48(19) . . . . ? C7 C8 C9 C14 56.16(19) . . . . ? C20 C8 C9 C14 -55.7(2) . . . . ? C14 C9 C10 C11 1.0(3) . . . . ? C8 C9 C10 C11 179.78(18) . . . . ? C9 C10 C11 C12 -0.7(3) . . . . ? C10 C11 C12 C13 -0.4(3) . . . . ? C11 C12 C13 C14 1.2(3) . . . . ? C12 C13 C14 C9 -0.9(3) . . . . ? C12 C13 C14 C1 179.84(17) . . . . ? C10 C9 C14 C13 -0.2(3) . . . . ? C8 C9 C14 C13 -179.09(16) . . . . ? C10 C9 C14 C1 179.17(16) . . . . ? C8 C9 C14 C1 0.2(2) . . . . ? C15 C1 C14 C13 -125.8(2) . . . . ? C2 C1 C14 C13 123.18(19) . . . . ? Se1 C1 C14 C13 4.3(2) . . . . ? C15 C1 C14 C9 55.0(2) . . . . ? C2 C1 C14 C9 -56.09(19) . . . . ? Se1 C1 C14 C9 -174.95(13) . . . . ? C14 C1 C15 C16 126.6(2) . . . . ? C2 C1 C15 C16 -122.2(2) . . . . ? Se1 C1 C15 C16 -3.4(3) . . . . ? C14 C1 C15 C20 -54.5(2) . . . . ? C2 C1 C15 C20 56.6(2) . . . . ? Se1 C1 C15 C20 175.48(13) . . . . ? C20 C15 C16 C17 0.3(3) . . . . ? C1 C15 C16 C17 179.08(18) . . . . ? C15 C16 C17 C18 -0.4(3) . . . . ? C16 C17 C18 C19 0.1(3) . . . . ? C17 C18 C19 C20 0.3(3) . . . . ? C18 C19 C20 C15 -0.4(3) . . . . ? C18 C19 C20 C8 -178.06(18) . . . . ? C16 C15 C20 C19 0.1(3) . . . . ? C1 C15 C20 C19 -178.85(17) . . . . ? C16 C15 C20 C8 178.06(17) . . . . ? C1 C15 C20 C8 -0.9(2) . . . . ? C9 C8 C20 C19 -126.1(2) . . . . ? C7 C8 C20 C19 122.2(2) . . . . ? C9 C8 C20 C15 56.1(2) . . . . ? C7 C8 C20 C15 -55.6(2) . . . . ? C1 Se1 C21 C26 5.86(18) . . . . ? C1 Se1 C21 C22 -174.62(14) . . . . ? C22 C21 C26 C25 -1.6(3) . . . . ? Se1 C21 C26 C25 177.93(14) . . . . ? C21 C26 C25 C24 -0.4(3) . . . . ? C26 C25 C24 C23 2.2(3) . . . . ? C26 C25 C24 Cl1 -177.75(14) . . . . ? C25 C24 C23 C22 -1.9(3) . . . . ? Cl1 C24 C23 C22 177.96(15) . . . . ? C24 C23 C22 C21 0.0(3) . . . . ? C26 C21 C22 C23 1.8(3) . . . . ? Se1 C21 C22 C23 -177.78(14) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.445 _refine_diff_density_min -0.498 _refine_diff_density_rms 0.105 # Attachment '1f_Se_NO2_Rev.cif' data_1f_wn005 _database_code_depnum_ccdc_archive 'CCDC 704860' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H17 N O2 Se' _chemical_formula_weight 454.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.9805(4) _cell_length_b 14.0346(7) _cell_length_c 34.5168(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3866.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 233 _cell_measurement_reflns_used 6635 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.65 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 1.967 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5899 _exptl_absorpt_correction_T_max 0.6944 _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_special_details ; ? ; _diffrn_ambient_temperature 233 _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 APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 19949 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4416 _reflns_number_gt 3564 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0554P)^2^+3.3065P] 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 4416 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.170 _refine_ls_restrained_S_all 1.170 _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 0.16285(3) 0.129517(19) 0.178555(8) 0.01838(11) Uani 1 1 d . . . C1 C 0.2057(3) 0.09940(19) 0.12405(8) 0.0144(5) Uani 1 1 d . . . C2 C 0.1305(3) 0.17968(19) 0.09908(8) 0.0150(5) Uani 1 1 d . . . C3 C 0.0438(3) 0.25877(19) 0.11191(8) 0.0168(5) Uani 1 1 d . . . H3A H 0.0274 0.2688 0.1386 0.020 Uiso 1 1 calc R . . C4 C -0.0201(4) 0.3243(2) 0.08469(9) 0.0209(6) Uani 1 1 d . . . H4A H -0.0787 0.3786 0.0931 0.025 Uiso 1 1 calc R . . C5 C 0.0039(4) 0.3085(2) 0.04543(9) 0.0232(6) Uani 1 1 d . . . H5A H -0.0406 0.3516 0.0273 0.028 Uiso 1 1 calc R . . C6 C 0.0933(4) 0.2296(2) 0.03271(8) 0.0195(6) Uani 1 1 d . . . H6A H 0.1114 0.2200 0.0061 0.023 Uiso 1 1 calc R . . C7 C 0.1555(3) 0.16529(19) 0.05938(8) 0.0147(5) Uani 1 1 d . . . C8 C 0.2504(3) 0.07360(19) 0.05009(8) 0.0155(5) Uani 1 1 d . . . H8A H 0.2672 0.0637 0.0220 0.019 Uiso 1 1 calc R . . C9 C 0.4149(3) 0.08073(18) 0.07263(8) 0.0165(5) Uani 1 1 d . . . C10 C 0.5735(3) 0.07552(19) 0.05644(9) 0.0185(6) Uani 1 1 d . . . H10A H 0.5878 0.0653 0.0297 0.022 Uiso 1 1 calc R . . C11 C 0.7126(4) 0.0860(2) 0.08117(9) 0.0229(6) Uani 1 1 d . . . H11A H 0.8216 0.0821 0.0710 0.027 Uiso 1 1 calc R . . C12 C 0.6901(3) 0.1020(2) 0.12052(9) 0.0220(6) Uani 1 1 d . . . H12A H 0.7839 0.1093 0.1367 0.026 Uiso 1 1 calc R . . C13 C 0.5302(3) 0.10727(19) 0.13609(9) 0.0191(6) Uani 1 1 d . . . H13A H 0.5153 0.1187 0.1627 0.023 Uiso 1 1 calc R . . C14 C 0.3928(3) 0.09559(18) 0.11220(8) 0.0151(5) Uani 1 1 d . . . C15 C 0.1252(3) 0.00713(18) 0.10885(8) 0.0135(5) Uani 1 1 d . . . C16 C 0.0314(3) -0.05871(19) 0.12958(8) 0.0173(5) Uani 1 1 d . . . H16A H 0.0106 -0.0493 0.1561 0.021 Uiso 1 1 calc R . . C17 C -0.0316(4) -0.1387(2) 0.11077(9) 0.0218(6) Uani 1 1 d . . . H17A H -0.0944 -0.1837 0.1248 0.026 Uiso 1 1 calc R . . C18 C -0.0028(4) -0.1527(2) 0.07187(9) 0.0230(6) Uani 1 1 d . . . H18A H -0.0447 -0.2076 0.0596 0.028 Uiso 1 1 calc R . . C19 C 0.0887(4) -0.0857(2) 0.05032(9) 0.0199(6) Uani 1 1 d . . . H19A H 0.1067 -0.0945 0.0236 0.024 Uiso 1 1 calc R . . C20 C 0.1520(3) -0.00620(19) 0.06911(8) 0.0153(5) Uani 1 1 d . . . C21 C 0.2496(3) 0.02437(19) 0.20695(8) 0.0180(6) Uani 1 1 d . . . C22 C 0.2169(4) 0.0282(2) 0.24687(9) 0.0227(6) Uani 1 1 d . . . H22A H 0.1641 0.0820 0.2575 0.027 Uiso 1 1 calc R . . C23 C 0.2624(4) -0.0472(2) 0.27060(8) 0.0241(6) Uani 1 1 d . . . H23A H 0.2390 -0.0460 0.2973 0.029 Uiso 1 1 calc R . . C24 C 0.3432(4) -0.1244(2) 0.25402(9) 0.0254(7) Uani 1 1 d . . . C25 C 0.3843(4) -0.1273(2) 0.21525(9) 0.0252(7) Uani 1 1 d . . . H25A H 0.4444 -0.1792 0.2051 0.030 Uiso 1 1 calc R . . C26 C 0.3360(4) -0.0527(2) 0.19134(9) 0.0203(6) Uani 1 1 d . . . H26A H 0.3615 -0.0543 0.1648 0.024 Uiso 1 1 calc R . . N1 N 0.3807(4) -0.20759(19) 0.27813(8) 0.0329(7) Uani 1 1 d . . . O1 O 0.3033(4) -0.21641(19) 0.30866(8) 0.0474(7) Uani 1 1 d . . . O2 O 0.4839(3) -0.26518(17) 0.26592(7) 0.0405(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.02472(17) 0.01502(16) 0.01540(16) -0.00112(10) -0.00183(11) 0.00493(11) C1 0.0158(12) 0.0138(12) 0.0135(13) 0.0002(10) -0.0020(10) 0.0000(10) C2 0.0113(12) 0.0144(12) 0.0192(14) 0.0034(10) -0.0035(10) -0.0039(10) C3 0.0171(13) 0.0148(12) 0.0184(14) -0.0004(10) -0.0027(11) -0.0020(10) C4 0.0189(14) 0.0152(13) 0.0285(16) 0.0027(11) -0.0009(12) 0.0033(11) C5 0.0179(14) 0.0223(15) 0.0294(17) 0.0127(12) -0.0024(12) 0.0017(11) C6 0.0198(14) 0.0222(14) 0.0165(14) 0.0040(11) -0.0039(11) -0.0040(11) C7 0.0104(11) 0.0154(12) 0.0184(14) 0.0012(10) -0.0019(10) -0.0024(10) C8 0.0126(13) 0.0191(13) 0.0147(13) -0.0017(10) -0.0003(10) -0.0026(10) C9 0.0128(12) 0.0130(12) 0.0238(15) 0.0016(11) -0.0026(11) -0.0005(10) C10 0.0163(13) 0.0116(12) 0.0274(16) 0.0030(11) 0.0015(12) -0.0002(10) C11 0.0137(13) 0.0185(14) 0.0366(18) 0.0040(13) 0.0003(12) 0.0006(11) C12 0.0150(13) 0.0165(13) 0.0345(17) 0.0017(12) -0.0100(12) -0.0016(11) C13 0.0200(13) 0.0130(12) 0.0243(15) 0.0005(11) -0.0065(12) -0.0004(11) C14 0.0132(12) 0.0102(12) 0.0219(14) 0.0009(10) -0.0028(11) -0.0008(10) C15 0.0112(12) 0.0120(12) 0.0173(13) 0.0002(10) -0.0022(10) 0.0023(10) C16 0.0165(13) 0.0184(13) 0.0171(14) 0.0013(11) -0.0011(10) -0.0002(11) C17 0.0187(13) 0.0159(13) 0.0308(17) 0.0049(12) -0.0015(12) -0.0033(11) C18 0.0233(15) 0.0146(13) 0.0311(17) -0.0030(12) -0.0065(13) -0.0037(11) C19 0.0195(14) 0.0205(14) 0.0197(14) -0.0043(11) -0.0020(11) 0.0002(11) C20 0.0095(12) 0.0162(13) 0.0203(14) -0.0004(11) -0.0022(10) 0.0011(10) C21 0.0192(14) 0.0166(13) 0.0182(14) 0.0005(11) -0.0029(11) -0.0029(11) C22 0.0271(15) 0.0211(14) 0.0198(15) 0.0005(12) -0.0021(12) -0.0005(12) C23 0.0316(16) 0.0256(15) 0.0151(15) 0.0022(12) -0.0041(12) -0.0063(13) C24 0.0349(17) 0.0180(14) 0.0232(16) 0.0054(12) -0.0110(13) -0.0033(13) C25 0.0303(16) 0.0173(14) 0.0281(17) -0.0018(12) -0.0102(13) -0.0003(12) C26 0.0250(15) 0.0166(13) 0.0193(14) 0.0016(11) -0.0056(12) 0.0011(11) N1 0.0525(18) 0.0211(14) 0.0249(15) 0.0025(11) -0.0176(13) -0.0028(13) O1 0.079(2) 0.0369(15) 0.0260(13) 0.0133(11) -0.0073(14) -0.0003(14) O2 0.0555(16) 0.0235(12) 0.0424(15) 0.0057(10) -0.0214(13) 0.0062(12) _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 C21 1.902(3) . ? Se1 C1 1.958(3) . ? C1 C15 1.538(4) . ? C1 C2 1.540(4) . ? C1 C14 1.549(4) . ? C2 C3 1.381(4) . ? C2 C7 1.399(4) . ? C3 C4 1.410(4) . ? C3 H3A 0.9400 . ? C4 C5 1.386(4) . ? C4 H4A 0.9400 . ? C5 C6 1.389(4) . ? C5 H5A 0.9400 . ? C6 C7 1.382(4) . ? C6 H6A 0.9400 . ? C7 C8 1.527(4) . ? C8 C20 1.517(4) . ? C8 C9 1.529(4) . ? C8 H8A 0.9900 . ? C9 C10 1.386(4) . ? C9 C14 1.393(4) . ? C10 C11 1.408(4) . ? C10 H10A 0.9400 . ? C11 C12 1.388(4) . ? C11 H11A 0.9400 . ? C12 C13 1.387(4) . ? C12 H12A 0.9400 . ? C13 C14 1.381(4) . ? C13 H13A 0.9400 . ? C15 C16 1.388(4) . ? C15 C20 1.401(4) . ? C16 C17 1.391(4) . ? C16 H16A 0.9400 . ? C17 C18 1.376(4) . ? C17 H17A 0.9400 . ? C18 C19 1.404(4) . ? C18 H18A 0.9400 . ? C19 C20 1.386(4) . ? C19 H19A 0.9400 . ? C21 C26 1.391(4) . ? C21 C22 1.403(4) . ? C22 C23 1.387(4) . ? C22 H22A 0.9400 . ? C23 C24 1.385(4) . ? C23 H23A 0.9400 . ? C24 C25 1.378(5) . ? C24 N1 1.464(4) . ? C25 C26 1.387(4) . ? C25 H25A 0.9400 . ? C26 H26A 0.9400 . ? N1 O1 1.227(4) . ? N1 O2 1.229(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 C21 Se1 C1 105.31(12) . . ? C15 C1 C2 105.2(2) . . ? C15 C1 C14 106.5(2) . . ? C2 C1 C14 104.7(2) . . ? C15 C1 Se1 115.87(18) . . ? C2 C1 Se1 108.15(18) . . ? C14 C1 Se1 115.45(18) . . ? C3 C2 C7 120.1(2) . . ? C3 C2 C1 127.1(3) . . ? C7 C2 C1 112.8(2) . . ? C2 C3 C4 119.5(3) . . ? C2 C3 H3A 120.3 . . ? C4 C3 H3A 120.3 . . ? C5 C4 C3 119.8(3) . . ? C5 C4 H4A 120.1 . . ? C3 C4 H4A 120.1 . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5A 119.8 . . ? C6 C5 H5A 119.8 . . ? C7 C6 C5 119.7(3) . . ? C7 C6 H6A 120.2 . . ? C5 C6 H6A 120.2 . . ? C6 C7 C2 120.5(3) . . ? C6 C7 C8 126.1(3) . . ? C2 C7 C8 113.4(2) . . ? C20 C8 C7 106.0(2) . . ? C20 C8 C9 105.8(2) . . ? C7 C8 C9 105.3(2) . . ? C20 C8 H8A 113.0 . . ? C7 C8 H8A 113.0 . . ? C9 C8 H8A 113.0 . . ? C10 C9 C14 121.3(3) . . ? C10 C9 C8 125.2(3) . . ? C14 C9 C8 113.6(2) . . ? C9 C10 C11 118.1(3) . . ? C9 C10 H10A 121.0 . . ? C11 C10 H10A 121.0 . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C13 C12 C11 120.5(3) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C14 C13 C12 119.5(3) . . ? C14 C13 H13A 120.2 . . ? C12 C13 H13A 120.2 . . ? C13 C14 C9 120.2(3) . . ? C13 C14 C1 127.1(3) . . ? C9 C14 C1 112.7(2) . . ? C16 C15 C20 119.9(2) . . ? C16 C15 C1 127.6(2) . . ? C20 C15 C1 112.5(2) . . ? C15 C16 C17 119.4(3) . . ? C15 C16 H16A 120.3 . . ? C17 C16 H16A 120.3 . . ? C18 C17 C16 120.7(3) . . ? C18 C17 H17A 119.7 . . ? C16 C17 H17A 119.7 . . ? C17 C18 C19 120.5(3) . . ? C17 C18 H18A 119.7 . . ? C19 C18 H18A 119.7 . . ? C20 C19 C18 118.8(3) . . ? C20 C19 H19A 120.6 . . ? C18 C19 H19A 120.6 . . ? C19 C20 C15 120.7(3) . . ? C19 C20 C8 125.5(3) . . ? C15 C20 C8 113.8(2) . . ? C26 C21 C22 120.2(3) . . ? C26 C21 Se1 125.7(2) . . ? C22 C21 Se1 114.1(2) . . ? C23 C22 C21 120.1(3) . . ? C23 C22 H22A 119.9 . . ? C21 C22 H22A 119.9 . . ? C24 C23 C22 118.4(3) . . ? C24 C23 H23A 120.8 . . ? C22 C23 H23A 120.8 . . ? C25 C24 C23 122.3(3) . . ? C25 C24 N1 118.7(3) . . ? C23 C24 N1 118.9(3) . . ? C24 C25 C26 119.3(3) . . ? C24 C25 H25A 120.3 . . ? C26 C25 H25A 120.3 . . ? C25 C26 C21 119.6(3) . . ? C25 C26 H26A 120.2 . . ? C21 C26 H26A 120.2 . . ? O1 N1 O2 124.4(3) . . ? O1 N1 C24 117.8(3) . . ? O2 N1 C24 117.8(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 C21 Se1 C1 C15 59.5(2) . . . . ? C21 Se1 C1 C2 177.25(17) . . . . ? C21 Se1 C1 C14 -65.9(2) . . . . ? C15 C1 C2 C3 122.9(3) . . . . ? C14 C1 C2 C3 -125.0(3) . . . . ? Se1 C1 C2 C3 -1.4(3) . . . . ? C15 C1 C2 C7 -56.0(3) . . . . ? C14 C1 C2 C7 56.0(3) . . . . ? Se1 C1 C2 C7 179.58(18) . . . . ? C7 C2 C3 C4 0.4(4) . . . . ? C1 C2 C3 C4 -178.5(2) . . . . ? C2 C3 C4 C5 0.4(4) . . . . ? C3 C4 C5 C6 -1.3(4) . . . . ? C4 C5 C6 C7 1.4(4) . . . . ? C5 C6 C7 C2 -0.7(4) . . . . ? C5 C6 C7 C8 177.7(2) . . . . ? C3 C2 C7 C6 -0.3(4) . . . . ? C1 C2 C7 C6 178.8(2) . . . . ? C3 C2 C7 C8 -178.8(2) . . . . ? C1 C2 C7 C8 0.3(3) . . . . ? C6 C7 C8 C20 -123.0(3) . . . . ? C2 C7 C8 C20 55.4(3) . . . . ? C6 C7 C8 C9 125.2(3) . . . . ? C2 C7 C8 C9 -56.4(3) . . . . ? C20 C8 C9 C10 125.0(3) . . . . ? C7 C8 C9 C10 -123.1(3) . . . . ? C20 C8 C9 C14 -56.4(3) . . . . ? C7 C8 C9 C14 55.5(3) . . . . ? C14 C9 C10 C11 -0.2(4) . . . . ? C8 C9 C10 C11 178.3(2) . . . . ? C9 C10 C11 C12 -0.6(4) . . . . ? C10 C11 C12 C13 0.4(4) . . . . ? C11 C12 C13 C14 0.6(4) . . . . ? C12 C13 C14 C9 -1.4(4) . . . . ? C12 C13 C14 C1 -179.7(3) . . . . ? C10 C9 C14 C13 1.2(4) . . . . ? C8 C9 C14 C13 -177.4(2) . . . . ? C10 C9 C14 C1 179.8(2) . . . . ? C8 C9 C14 C1 1.1(3) . . . . ? C15 C1 C14 C13 -127.4(3) . . . . ? C2 C1 C14 C13 121.5(3) . . . . ? Se1 C1 C14 C13 2.8(4) . . . . ? C15 C1 C14 C9 54.2(3) . . . . ? C2 C1 C14 C9 -56.9(3) . . . . ? Se1 C1 C14 C9 -175.64(18) . . . . ? C2 C1 C15 C16 -122.0(3) . . . . ? C14 C1 C15 C16 127.2(3) . . . . ? Se1 C1 C15 C16 -2.7(3) . . . . ? C2 C1 C15 C20 56.6(3) . . . . ? C14 C1 C15 C20 -54.1(3) . . . . ? Se1 C1 C15 C20 175.98(18) . . . . ? C20 C15 C16 C17 1.6(4) . . . . ? C1 C15 C16 C17 -179.9(2) . . . . ? C15 C16 C17 C18 -0.5(4) . . . . ? C16 C17 C18 C19 -0.9(4) . . . . ? C17 C18 C19 C20 1.2(4) . . . . ? C18 C19 C20 C15 -0.1(4) . . . . ? C18 C19 C20 C8 -178.8(3) . . . . ? C16 C15 C20 C19 -1.3(4) . . . . ? C1 C15 C20 C19 179.9(2) . . . . ? C16 C15 C20 C8 177.5(2) . . . . ? C1 C15 C20 C8 -1.2(3) . . . . ? C7 C8 C20 C19 123.9(3) . . . . ? C9 C8 C20 C19 -124.7(3) . . . . ? C7 C8 C20 C15 -54.9(3) . . . . ? C9 C8 C20 C15 56.5(3) . . . . ? C1 Se1 C21 C26 4.4(3) . . . . ? C1 Se1 C21 C22 -174.4(2) . . . . ? C26 C21 C22 C23 -3.6(4) . . . . ? Se1 C21 C22 C23 175.3(2) . . . . ? C21 C22 C23 C24 1.4(4) . . . . ? C22 C23 C24 C25 2.1(5) . . . . ? C22 C23 C24 N1 -175.5(3) . . . . ? C23 C24 C25 C26 -3.4(5) . . . . ? N1 C24 C25 C26 174.2(3) . . . . ? C24 C25 C26 C21 1.1(4) . . . . ? C22 C21 C26 C25 2.3(4) . . . . ? Se1 C21 C26 C25 -176.4(2) . . . . ? C25 C24 N1 O1 -159.4(3) . . . . ? C23 C24 N1 O1 18.3(4) . . . . ? C25 C24 N1 O2 18.6(4) . . . . ? C23 C24 N1 O2 -163.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.663 _refine_diff_density_min -0.814 _refine_diff_density_rms 0.102