# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'J. Woollins' _publ_contact_author_address ; Department of Chemistry University of St Andrews St Andrews FIFE SCOTLAND KY16 9ST UNITED KINGDOM ; _publ_contact_author_email JDW3@ST-ANDREWS.AC.UK _publ_section_title ; Unexpected four and eight membered organo P-Se heterocycles ; loop_ _publ_author_name J.Woolins 'Guoxiong Hua.' 'Yang Li.' A.M.Z.Slawin data_p21c_2 _database_code_depnum_ccdc_archive 'CCDC 629191' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H20 P2 Se6,C H Cl3' _chemical_formula_sum 'C29 H21 Cl3 P2 Se6' _chemical_formula_weight 1011.51 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.3239(15) _cell_length_b 13.9985(16) _cell_length_c 17.2947(19) _cell_angle_alpha 90.00 _cell_angle_beta 95.309(3) _cell_angle_gamma 90.00 _cell_volume 3211.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 7343 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 25.99 _exptl_crystal_description Needle _exptl_crystal_colour Orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.092 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 7.206 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4112 _exptl_absorpt_correction_T_max 0.7615 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16397 _diffrn_reflns_av_R_equivalents 0.1124 _diffrn_reflns_av_sigmaI/netI 0.0970 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 27.66 _reflns_number_total 5871 _reflns_number_gt 4081 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0274P)^2^+49.0100P] 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 5871 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1188 _refine_ls_R_factor_gt 0.0729 _refine_ls_wR_factor_ref 0.1353 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 0.51797(8) 0.62983(7) 0.11798(6) 0.0197(2) Uani 1 1 d . . . Se2 Se 0.62332(8) 0.48777(7) 0.28036(5) 0.0179(2) Uani 1 1 d . . . Se3 Se 0.55143(8) 0.51911(8) 0.39616(5) 0.0217(3) Uani 1 1 d . . . Se11 Se 0.17255(8) 0.50901(7) 0.58761(5) 0.0182(2) Uani 1 1 d . . . Se12 Se 0.31744(8) 0.72394(7) 0.55852(5) 0.0174(2) Uani 1 1 d . . . Se13 Se 0.42475(8) 0.71409(7) 0.45874(5) 0.0191(2) Uani 1 1 d . . . P1 P 0.4850(2) 0.52893(17) 0.20286(13) 0.0138(5) Uani 1 1 d . . . P11 P 0.2093(2) 0.61203(18) 0.50624(13) 0.0145(5) Uani 1 1 d . . . C1 C 0.4284(8) 0.4205(7) 0.1622(5) 0.016(2) Uani 1 1 d . . . C2 C 0.3926(8) 0.4137(7) 0.0850(5) 0.018(2) Uani 1 1 d . . . H2 H 0.4010 0.4651 0.0504 0.022 Uiso 1 1 calc R . . C3 C 0.3438(8) 0.3298(7) 0.0586(6) 0.023(2) Uani 1 1 d . . . H3 H 0.3192 0.3245 0.0055 0.027 Uiso 1 1 calc R . . C4 C 0.3306(8) 0.2544(8) 0.1083(6) 0.023(2) Uani 1 1 d . . . H4 H 0.2947 0.1987 0.0906 0.028 Uiso 1 1 calc R . . C5 C 0.3707(9) 0.2621(7) 0.1838(6) 0.022(2) Uani 1 1 d . . . H5 H 0.3641 0.2100 0.2182 0.027 Uiso 1 1 calc R . . C6 C 0.4200(9) 0.3424(8) 0.2112(6) 0.028(3) Uani 1 1 d . . . H6 H 0.4486 0.3451 0.2635 0.033 Uiso 1 1 calc R . . C7 C 0.4259(7) 0.5674(6) 0.3492(5) 0.0098(19) Uani 1 1 d . . . C8 C 0.4007(8) 0.5725(7) 0.2720(5) 0.014(2) Uani 1 1 d . . . C9 C 0.3037(8) 0.6147(7) 0.2373(5) 0.020(2) Uani 1 1 d . . . C10 C 0.2893(9) 0.7138(7) 0.2437(6) 0.022(2) Uani 1 1 d . . . H10 H 0.3407 0.7524 0.2694 0.027 Uiso 1 1 calc R . . C11 C 0.2006(9) 0.7551(8) 0.2126(6) 0.029(3) Uani 1 1 d . . . H11 H 0.1902 0.8218 0.2179 0.034 Uiso 1 1 calc R . . C12 C 0.1260(9) 0.6986(8) 0.1734(6) 0.028(3) Uani 1 1 d . . . H12 H 0.0650 0.7271 0.1517 0.033 Uiso 1 1 calc R . . C13 C 0.1403(9) 0.6020(9) 0.1659(6) 0.033(3) Uani 1 1 d . . . H13 H 0.0891 0.5640 0.1391 0.039 Uiso 1 1 calc R . . C14 C 0.2297(8) 0.5591(8) 0.1976(5) 0.021(2) Uani 1 1 d . . . H14 H 0.2397 0.4924 0.1919 0.025 Uiso 1 1 calc R . . C15 C 0.3630(7) 0.6029(7) 0.4094(5) 0.015(2) Uani 1 1 d . . . C16 C 0.2776(8) 0.5634(7) 0.4279(5) 0.017(2) Uani 1 1 d . . . C17 C 0.2326(8) 0.4734(7) 0.3913(5) 0.017(2) Uani 1 1 d . . . C18 C 0.2892(9) 0.3906(7) 0.3933(6) 0.024(2) Uani 1 1 d . . . H18 H 0.3552 0.3905 0.4193 0.029 Uiso 1 1 calc R . . C19 C 0.2508(9) 0.3069(8) 0.3578(6) 0.027(3) Uani 1 1 d . . . H19 H 0.2910 0.2508 0.3571 0.032 Uiso 1 1 calc R . . C20 C 0.1519(9) 0.3080(8) 0.3233(6) 0.027(3) Uani 1 1 d . . . H20 H 0.1242 0.2518 0.2989 0.033 Uiso 1 1 calc R . . C21 C 0.0937(9) 0.3894(8) 0.3240(6) 0.028(3) Uani 1 1 d . . . H21 H 0.0258 0.3887 0.3017 0.034 Uiso 1 1 calc R . . C22 C 0.1347(8) 0.4720(8) 0.3574(5) 0.023(2) Uani 1 1 d . . . H22 H 0.0951 0.5285 0.3570 0.028 Uiso 1 1 calc R . . C23 C 0.1024(8) 0.6757(7) 0.4627(5) 0.016(2) Uani 1 1 d . . . C24 C 0.1078(9) 0.7308(8) 0.3959(6) 0.0259(17) Uani 1 1 d . . . H24 H 0.1686 0.7317 0.3712 0.031 Uiso 1 1 calc R . . C25 C 0.0288(8) 0.7824(8) 0.3661(6) 0.0259(17) Uani 1 1 d . . . H25 H 0.0349 0.8193 0.3206 0.031 Uiso 1 1 calc R . . C26 C -0.0594(8) 0.7835(8) 0.3990(6) 0.026(3) Uani 1 1 d . . . H26 H -0.1137 0.8224 0.3781 0.032 Uiso 1 1 calc R . . C27 C -0.0694(8) 0.7264(8) 0.4640(6) 0.024(2) Uani 1 1 d . . . H27 H -0.1317 0.7246 0.4867 0.029 Uiso 1 1 calc R . . C28 C 0.0098(8) 0.6736(8) 0.4950(6) 0.021(2) Uani 1 1 d . . . H28 H 0.0024 0.6348 0.5391 0.025 Uiso 1 1 calc R . . C29 C 0.2066(9) 1.0229(9) 0.3861(7) 0.036(3) Uani 1 1 d . . . H29 H 0.2520 1.0800 0.3885 0.02(3) Uiso 1 1 calc R . . Cl1 Cl 0.1261(3) 1.0344(3) 0.4612(2) 0.0651(12) Uani 1 1 d . . . Cl2 Cl 0.1328(2) 1.0258(2) 0.29554(17) 0.0364(7) Uani 1 1 d . . . Cl3 Cl 0.2819(3) 0.9225(2) 0.39654(18) 0.0388(7) 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 0.0209(6) 0.0215(5) 0.0169(5) 0.0080(4) 0.0021(4) 0.0007(4) Se2 0.0172(5) 0.0232(5) 0.0132(4) 0.0011(4) 0.0014(4) 0.0061(4) Se3 0.0186(6) 0.0355(6) 0.0107(4) 0.0017(4) -0.0001(4) 0.0094(5) Se11 0.0217(6) 0.0191(5) 0.0137(4) 0.0035(4) 0.0016(4) -0.0003(4) Se12 0.0186(6) 0.0198(5) 0.0139(4) -0.0043(4) 0.0018(4) -0.0017(4) Se13 0.0211(6) 0.0201(5) 0.0164(5) -0.0042(4) 0.0033(4) -0.0055(4) P1 0.0175(14) 0.0139(12) 0.0098(10) 0.0019(9) 0.0006(10) 0.0006(10) P11 0.0165(14) 0.0170(13) 0.0102(11) -0.0004(9) 0.0018(10) 0.0002(10) C1 0.022(6) 0.014(5) 0.015(4) -0.005(4) 0.008(4) 0.004(4) C2 0.017(6) 0.029(6) 0.010(4) 0.005(4) 0.006(4) 0.005(4) C3 0.026(7) 0.025(6) 0.016(5) -0.004(4) -0.003(4) 0.000(5) C4 0.021(6) 0.025(6) 0.023(5) -0.006(4) -0.005(4) -0.004(5) C5 0.034(7) 0.010(5) 0.024(5) 0.000(4) 0.007(5) 0.000(5) C6 0.031(7) 0.033(6) 0.019(5) 0.000(5) 0.005(5) -0.001(5) C7 0.014(5) 0.011(5) 0.005(4) -0.002(3) 0.002(4) 0.000(4) C8 0.018(5) 0.016(5) 0.011(4) 0.001(4) 0.009(4) 0.004(4) C9 0.020(6) 0.023(6) 0.015(5) 0.004(4) -0.004(4) 0.005(4) C10 0.033(7) 0.013(5) 0.022(5) 0.008(4) 0.004(5) 0.003(5) C11 0.037(7) 0.023(6) 0.028(6) 0.006(5) 0.015(5) 0.013(5) C12 0.031(7) 0.040(7) 0.014(5) 0.020(5) 0.009(5) 0.021(5) C13 0.028(7) 0.057(8) 0.012(5) 0.004(5) -0.009(5) 0.006(6) C14 0.023(6) 0.027(6) 0.014(5) 0.004(4) 0.003(4) 0.000(5) C15 0.013(5) 0.019(5) 0.011(4) 0.007(4) -0.002(4) -0.001(4) C16 0.020(6) 0.028(6) 0.005(4) 0.002(4) 0.000(4) 0.002(4) C17 0.024(6) 0.017(5) 0.009(4) 0.001(4) 0.001(4) -0.007(4) C18 0.035(7) 0.015(5) 0.023(5) 0.005(4) 0.002(5) 0.004(5) C19 0.029(7) 0.022(6) 0.029(6) 0.004(5) 0.005(5) 0.001(5) C20 0.037(7) 0.030(6) 0.017(5) -0.004(4) 0.010(5) -0.005(5) C21 0.027(7) 0.035(7) 0.023(5) -0.008(5) 0.001(5) -0.009(5) C22 0.023(6) 0.031(6) 0.016(5) -0.010(4) 0.007(4) 0.001(5) C23 0.024(6) 0.016(5) 0.009(4) -0.004(4) 0.002(4) -0.008(4) C24 0.022(4) 0.033(4) 0.025(4) 0.016(3) 0.010(3) 0.002(3) C25 0.022(4) 0.033(4) 0.025(4) 0.016(3) 0.010(3) 0.002(3) C26 0.021(6) 0.028(6) 0.029(6) 0.009(5) -0.004(5) 0.014(5) C27 0.020(6) 0.027(6) 0.027(5) 0.000(5) 0.008(5) 0.001(5) C28 0.023(6) 0.025(6) 0.015(5) 0.001(4) -0.001(4) 0.004(5) C29 0.021(6) 0.042(7) 0.047(7) -0.012(6) 0.010(6) -0.009(6) Cl1 0.050(2) 0.108(3) 0.0403(18) -0.030(2) 0.0173(17) -0.010(2) Cl2 0.0348(18) 0.0403(17) 0.0345(15) -0.0006(13) 0.0044(13) 0.0031(14) Cl3 0.046(2) 0.0303(16) 0.0398(16) 0.0054(13) 0.0005(14) -0.0023(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 P1 2.113(3) . ? Se2 P1 2.252(3) . ? Se2 Se3 2.3401(14) . ? Se3 C7 1.914(9) . ? Se11 P11 2.104(3) . ? Se12 P11 2.260(3) . ? Se12 Se13 2.3447(15) . ? Se13 C15 1.923(9) . ? P1 C1 1.807(10) . ? P1 C8 1.821(10) . ? P11 C23 1.787(10) . ? P11 C16 1.833(10) . ? C1 C2 1.378(12) . ? C1 C6 1.394(14) . ? C2 C3 1.399(15) . ? C2 H2 0.9500 . ? C3 C4 1.383(15) . ? C3 H3 0.9500 . ? C4 C5 1.368(14) . ? C4 H4 0.9500 . ? C5 C6 1.365(15) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.348(12) . ? C7 C15 1.480(13) . ? C8 C9 1.496(13) . ? C9 C14 1.387(14) . ? C9 C10 1.406(14) . ? C10 C11 1.379(15) . ? C10 H10 0.9500 . ? C11 C12 1.396(17) . ? C11 H11 0.9500 . ? C12 C13 1.373(17) . ? C12 H12 0.9500 . ? C13 C14 1.400(15) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.331(14) . ? C16 C17 1.509(14) . ? C17 C22 1.380(14) . ? C17 C18 1.382(14) . ? C18 C19 1.398(15) . ? C18 H18 0.9500 . ? C19 C20 1.396(16) . ? C19 H19 0.9500 . ? C20 C21 1.379(16) . ? C20 H20 0.9500 . ? C21 C22 1.382(15) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.395(13) . ? C23 C28 1.401(15) . ? C24 C25 1.341(15) . ? C24 H24 0.9500 . ? C25 C26 1.352(16) . ? C25 H25 0.9500 . ? C26 C27 1.397(15) . ? C26 H26 0.9500 . ? C27 C28 1.357(15) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 Cl3 1.726(13) . ? C29 Cl1 1.767(13) . ? C29 Cl2 1.771(12) . ? C29 H29 1.0000 . ? 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 P1 Se2 Se3 94.83(8) . . ? C7 Se3 Se2 96.6(3) . . ? P11 Se12 Se13 94.27(8) . . ? C15 Se13 Se12 96.3(3) . . ? C1 P1 C8 106.1(5) . . ? C1 P1 Se1 113.4(3) . . ? C8 P1 Se1 114.4(3) . . ? C1 P1 Se2 107.8(3) . . ? C8 P1 Se2 102.4(3) . . ? Se1 P1 Se2 111.91(12) . . ? C23 P11 C16 107.7(4) . . ? C23 P11 Se11 113.5(3) . . ? C16 P11 Se11 113.7(3) . . ? C23 P11 Se12 106.1(3) . . ? C16 P11 Se12 102.2(3) . . ? Se11 P11 Se12 112.75(11) . . ? C2 C1 C6 119.6(9) . . ? C2 C1 P1 122.0(8) . . ? C6 C1 P1 118.4(7) . . ? C1 C2 C3 118.9(9) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 121.3(9) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C5 C4 C3 118.2(9) . . ? C5 C4 H4 120.9 . . ? C3 C4 H4 120.9 . . ? C6 C5 C4 121.9(10) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C5 C6 C1 119.9(9) . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C8 C7 C15 124.9(8) . . ? C8 C7 Se3 124.5(7) . . ? C15 C7 Se3 110.5(6) . . ? C7 C8 C9 123.0(9) . . ? C7 C8 P1 121.4(7) . . ? C9 C8 P1 115.6(6) . . ? C14 C9 C10 119.8(10) . . ? C14 C9 C8 121.7(9) . . ? C10 C9 C8 118.5(9) . . ? C11 C10 C9 120.0(10) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 119.9(10) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C13 C12 C11 120.3(10) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.4(11) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C9 C14 C13 119.6(10) . . ? C9 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C16 C15 C7 125.6(9) . . ? C16 C15 Se13 124.7(8) . . ? C7 C15 Se13 109.7(7) . . ? C15 C16 C17 124.2(9) . . ? C15 C16 P11 121.2(8) . . ? C17 C16 P11 114.5(7) . . ? C22 C17 C18 119.4(9) . . ? C22 C17 C16 120.9(9) . . ? C18 C17 C16 119.7(9) . . ? C17 C18 C19 121.1(10) . . ? C17 C18 H18 119.5 . . ? C19 C18 H18 119.5 . . ? C20 C19 C18 118.1(10) . . ? C20 C19 H19 121.0 . . ? C18 C19 H19 121.0 . . ? C21 C20 C19 121.0(10) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 119.6(11) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C17 C22 C21 120.8(10) . . ? C17 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C24 C23 C28 117.2(10) . . ? C24 C23 P11 121.6(8) . . ? C28 C23 P11 121.2(7) . . ? C25 C24 C23 121.2(11) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C24 C25 C26 121.7(10) . . ? C24 C25 H25 119.1 . . ? C26 C25 H25 119.1 . . ? C25 C26 C27 119.0(10) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? C28 C27 C26 120.0(11) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C23 120.8(10) . . ? C27 C28 H28 119.6 . . ? C23 C28 H28 119.6 . . ? Cl3 C29 Cl1 112.6(7) . . ? Cl3 C29 Cl2 112.4(7) . . ? Cl1 C29 Cl2 108.8(7) . . ? Cl3 C29 H29 107.6 . . ? Cl1 C29 H29 107.6 . . ? Cl2 C29 H29 107.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag P1 Se2 Se3 C7 -3.8(3) . . . . ? P11 Se12 Se13 C15 -9.5(3) . . . . ? Se3 Se2 P1 C1 -106.9(3) . . . . ? Se3 Se2 P1 C8 4.7(3) . . . . ? Se3 Se2 P1 Se1 127.75(10) . . . . ? Se13 Se12 P11 C23 -103.0(3) . . . . ? Se13 Se12 P11 C16 9.8(3) . . . . ? Se13 Se12 P11 Se11 132.27(11) . . . . ? C8 P1 C1 C2 114.1(9) . . . . ? Se1 P1 C1 C2 -12.3(10) . . . . ? Se2 P1 C1 C2 -136.7(8) . . . . ? C8 P1 C1 C6 -65.0(9) . . . . ? Se1 P1 C1 C6 168.6(8) . . . . ? Se2 P1 C1 C6 44.2(9) . . . . ? C6 C1 C2 C3 3.3(15) . . . . ? P1 C1 C2 C3 -175.8(8) . . . . ? C1 C2 C3 C4 0.3(16) . . . . ? C2 C3 C4 C5 -2.9(17) . . . . ? C3 C4 C5 C6 2.0(17) . . . . ? C4 C5 C6 C1 1.6(18) . . . . ? C2 C1 C6 C5 -4.2(17) . . . . ? P1 C1 C6 C5 174.9(9) . . . . ? Se2 Se3 C7 C8 1.9(8) . . . . ? Se2 Se3 C7 C15 -175.1(6) . . . . ? C15 C7 C8 C9 -0.6(15) . . . . ? Se3 C7 C8 C9 -177.2(7) . . . . ? C15 C7 C8 P1 178.6(7) . . . . ? Se3 C7 C8 P1 2.1(12) . . . . ? C1 P1 C8 C7 108.0(9) . . . . ? Se1 P1 C8 C7 -126.2(7) . . . . ? Se2 P1 C8 C7 -4.9(9) . . . . ? C1 P1 C8 C9 -72.7(8) . . . . ? Se1 P1 C8 C9 53.1(8) . . . . ? Se2 P1 C8 C9 174.4(7) . . . . ? C7 C8 C9 C14 -112.7(11) . . . . ? P1 C8 C9 C14 68.0(12) . . . . ? C7 C8 C9 C10 69.2(14) . . . . ? P1 C8 C9 C10 -110.1(9) . . . . ? C14 C9 C10 C11 2.1(16) . . . . ? C8 C9 C10 C11 -179.7(10) . . . . ? C9 C10 C11 C12 -1.4(16) . . . . ? C10 C11 C12 C13 0.4(16) . . . . ? C11 C12 C13 C14 0.0(17) . . . . ? C10 C9 C14 C13 -1.7(15) . . . . ? C8 C9 C14 C13 -179.8(10) . . . . ? C12 C13 C14 C9 0.6(16) . . . . ? C8 C7 C15 C16 71.4(14) . . . . ? Se3 C7 C15 C16 -111.7(9) . . . . ? C8 C7 C15 Se13 -109.8(9) . . . . ? Se3 C7 C15 Se13 67.2(7) . . . . ? Se12 Se13 C15 C16 8.4(8) . . . . ? Se12 Se13 C15 C7 -170.5(5) . . . . ? C7 C15 C16 C17 1.8(15) . . . . ? Se13 C15 C16 C17 -176.9(7) . . . . ? C7 C15 C16 P11 177.7(7) . . . . ? Se13 C15 C16 P11 -1.1(12) . . . . ? C23 P11 C16 C15 104.2(8) . . . . ? Se11 P11 C16 C15 -129.1(7) . . . . ? Se12 P11 C16 C15 -7.3(8) . . . . ? C23 P11 C16 C17 -79.6(8) . . . . ? Se11 P11 C16 C17 47.1(7) . . . . ? Se12 P11 C16 C17 168.9(6) . . . . ? C15 C16 C17 C22 -125.4(11) . . . . ? P11 C16 C17 C22 58.5(11) . . . . ? C15 C16 C17 C18 56.1(13) . . . . ? P11 C16 C17 C18 -120.0(9) . . . . ? C22 C17 C18 C19 3.6(16) . . . . ? C16 C17 C18 C19 -177.8(9) . . . . ? C17 C18 C19 C20 -3.0(16) . . . . ? C18 C19 C20 C21 0.2(17) . . . . ? C19 C20 C21 C22 1.9(17) . . . . ? C18 C17 C22 C21 -1.4(15) . . . . ? C16 C17 C22 C21 -180.0(9) . . . . ? C20 C21 C22 C17 -1.3(16) . . . . ? C16 P11 C23 C24 -38.6(10) . . . . ? Se11 P11 C23 C24 -165.5(7) . . . . ? Se12 P11 C23 C24 70.2(8) . . . . ? C16 P11 C23 C28 142.4(8) . . . . ? Se11 P11 C23 C28 15.6(9) . . . . ? Se12 P11 C23 C28 -108.7(8) . . . . ? C28 C23 C24 C25 2.6(16) . . . . ? P11 C23 C24 C25 -176.4(9) . . . . ? C23 C24 C25 C26 -0.1(18) . . . . ? C24 C25 C26 C27 -2.4(18) . . . . ? C25 C26 C27 C28 2.3(16) . . . . ? C26 C27 C28 C23 0.3(16) . . . . ? C24 C23 C28 C27 -2.7(15) . . . . ? P11 C23 C28 C27 176.3(8) . . . . ? _diffrn_measured_fraction_theta_max 0.783 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.949 _refine_diff_density_min -0.934 _refine_diff_density_rms 0.212 # Attachment '5.cif' data_p21c _database_code_depnum_ccdc_archive 'CCDC 629192' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H23 P Se2' _chemical_formula_sum 'C18 H23 P Se2' _chemical_formula_weight 428.25 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' P P 0.1023 0.0942 '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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1765(10) _cell_length_b 25.499(3) _cell_length_c 9.2946(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.984(3) _cell_angle_gamma 90.00 _cell_volume 1935.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 7696 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 28.16 _exptl_crystal_description Prism _exptl_crystal_colour Orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 3.897 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5096 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10297 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0405 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.45 _reflns_number_total 3523 _reflns_number_gt 2993 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+1.1519P] 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 3523 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.169 _refine_ls_restrained_S_all 1.169 _refine_ls_shift/su_max 0.007 _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 1.25588(5) 0.026753(17) 0.41290(4) 0.01954(14) Uani 1 1 d . . . Se2 Se 0.90358(4) 0.095651(15) 0.58065(4) 0.01450(13) Uani 1 1 d . . . P1 P 1.16459(11) 0.06358(4) 0.59345(10) 0.0123(2) Uani 1 1 d . . . C1 C 1.2027(4) 0.02858(15) 0.7621(4) 0.0138(8) Uani 1 1 d . . . C2 C 1.1471(5) 0.05019(18) 0.8884(5) 0.0225(9) Uani 1 1 d . . . H2 H 1.0829 0.0812 0.8845 0.027 Uiso 1 1 calc R . . C3 C 1.1858(5) 0.02628(18) 1.0194(5) 0.0261(10) Uani 1 1 d . . . H3 H 1.1483 0.0409 1.1057 0.031 Uiso 1 1 calc R . . C4 C 1.2794(5) -0.01910(17) 1.0244(5) 0.0221(9) Uani 1 1 d . . . H4 H 1.3054 -0.0355 1.1144 0.026 Uiso 1 1 calc R . . C5 C 1.3352(5) -0.04071(17) 0.8997(5) 0.0206(9) Uani 1 1 d . . . H5 H 1.4000 -0.0716 0.9042 0.025 Uiso 1 1 calc R . . C6 C 1.2962(5) -0.01695(16) 0.7673(4) 0.0166(8) Uani 1 1 d . . . H6 H 1.3332 -0.0318 0.6810 0.020 Uiso 1 1 calc R . . C7 C 1.0587(4) 0.15384(15) 0.6120(4) 0.0126(8) Uani 1 1 d . . . C8 C 1.2113(4) 0.13251(15) 0.6241(4) 0.0139(8) Uani 1 1 d . . . C9 C 1.3774(5) 0.15797(17) 0.6516(4) 0.0195(9) Uani 1 1 d . . . C10 C 1.4401(7) 0.1766(3) 0.5082(6) 0.0576(19) Uani 1 1 d . . . H10A H 1.4450 0.1469 0.4420 0.086 Uiso 1 1 calc R . . H10B H 1.5498 0.1917 0.5245 0.086 Uiso 1 1 calc R . . H10C H 1.3657 0.2033 0.4664 0.086 Uiso 1 1 calc R . . C11 C 1.3679(6) 0.2035(2) 0.7581(7) 0.0396(13) Uani 1 1 d . . . H11A H 1.3041 0.2322 0.7131 0.059 Uiso 1 1 calc R . . H11B H 1.4787 0.2158 0.7852 0.059 Uiso 1 1 calc R . . H11C H 1.3148 0.1915 0.8444 0.059 Uiso 1 1 calc R . . C12 C 1.4983(5) 0.11785(19) 0.7197(6) 0.0312(11) Uani 1 1 d . . . H12A H 1.4589 0.1059 0.8119 0.047 Uiso 1 1 calc R . . H12B H 1.6061 0.1343 0.7357 0.047 Uiso 1 1 calc R . . H12C H 1.5071 0.0878 0.6548 0.047 Uiso 1 1 calc R . . C13 C 1.0049(4) 0.20676(16) 0.6178(4) 0.0156(8) Uani 1 1 d . . . C14 C 0.9549(5) 0.25099(16) 0.6238(4) 0.0151(8) Uani 1 1 d . . . C15 C 0.9045(4) 0.30643(16) 0.6335(4) 0.0157(8) Uani 1 1 d . . . C16 C 0.8513(6) 0.32597(17) 0.4813(5) 0.0270(10) Uani 1 1 d . . . H16A H 0.9417 0.3214 0.4173 0.040 Uiso 1 1 calc R . . H16B H 0.8219 0.3632 0.4856 0.040 Uiso 1 1 calc R . . H16C H 0.7563 0.3057 0.4442 0.040 Uiso 1 1 calc R . . C17 C 0.7620(5) 0.31068(18) 0.7339(5) 0.0253(10) Uani 1 1 d . . . H17A H 0.6681 0.2908 0.6932 0.038 Uiso 1 1 calc R . . H17B H 0.7311 0.3476 0.7439 0.038 Uiso 1 1 calc R . . H17C H 0.7958 0.2964 0.8287 0.038 Uiso 1 1 calc R . . C18 C 1.0493(5) 0.33926(19) 0.6938(5) 0.0289(10) Uani 1 1 d . . . H18A H 1.0832 0.3267 0.7905 0.043 Uiso 1 1 calc R . . H18B H 1.0165 0.3761 0.6989 0.043 Uiso 1 1 calc R . . H18C H 1.1410 0.3359 0.6306 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.0278(2) 0.0178(3) 0.0134(2) -0.00242(17) 0.00422(16) 0.00506(16) Se2 0.0133(2) 0.0133(2) 0.0167(2) -0.00037(16) -0.00133(14) 0.00081(14) P1 0.0155(5) 0.0101(5) 0.0113(5) 0.0003(4) 0.0000(4) 0.0026(4) C1 0.0149(18) 0.014(2) 0.013(2) 0.0019(16) -0.0025(15) -0.0026(14) C2 0.029(2) 0.020(2) 0.018(2) 0.0042(18) 0.0041(17) 0.0083(17) C3 0.033(2) 0.031(3) 0.014(2) 0.0017(19) 0.0046(18) 0.0080(19) C4 0.027(2) 0.022(2) 0.017(2) 0.0062(18) -0.0065(17) -0.0040(17) C5 0.023(2) 0.013(2) 0.025(2) 0.0031(18) -0.0051(17) 0.0019(16) C6 0.021(2) 0.015(2) 0.015(2) -0.0027(17) -0.0006(15) 0.0005(15) C7 0.0186(18) 0.0077(19) 0.0116(19) 0.0029(16) 0.0010(15) 0.0011(14) C8 0.0181(19) 0.013(2) 0.0104(19) 0.0042(16) 0.0001(15) 0.0027(15) C9 0.0173(19) 0.021(2) 0.020(2) -0.0002(19) 0.0029(16) -0.0039(16) C10 0.046(3) 0.090(5) 0.036(3) 0.023(3) -0.001(3) -0.041(3) C11 0.020(2) 0.027(3) 0.070(4) -0.019(3) -0.015(2) 0.0020(19) C12 0.016(2) 0.025(3) 0.052(3) -0.008(2) -0.005(2) 0.0006(18) C13 0.0146(18) 0.019(2) 0.013(2) 0.0006(17) -0.0012(15) 0.0002(16) C14 0.0170(19) 0.014(2) 0.014(2) 0.0004(17) -0.0011(15) 0.0026(15) C15 0.0203(19) 0.013(2) 0.014(2) 0.0022(17) 0.0019(15) 0.0025(15) C16 0.046(3) 0.015(2) 0.020(2) 0.0016(19) -0.0005(19) 0.0120(19) C17 0.030(2) 0.016(2) 0.031(3) -0.002(2) 0.0114(19) 0.0061(17) C18 0.032(2) 0.025(3) 0.030(3) -0.005(2) 0.003(2) -0.0035(19) _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 P1 2.0941(11) . ? Se2 C7 1.964(4) . ? Se2 P1 2.2828(10) . ? P1 C1 1.816(4) . ? P1 C8 1.818(4) . ? C1 C6 1.389(6) . ? C1 C2 1.394(6) . ? C2 C3 1.384(6) . ? C2 H2 0.9500 . ? C3 C4 1.387(6) . ? C3 H3 0.9500 . ? C4 C5 1.382(6) . ? C4 H4 0.9500 . ? C5 C6 1.394(6) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.361(5) . ? C7 C13 1.421(5) . ? C8 C9 1.515(5) . ? C9 C10 1.528(7) . ? C9 C11 1.530(6) . ? C9 C12 1.536(6) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.202(6) . ? C14 C15 1.477(6) . ? C15 C18 1.532(6) . ? C15 C17 1.534(6) . ? C15 C16 1.541(6) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 Se2 P1 70.62(11) . . ? C1 P1 C8 108.33(17) . . ? C1 P1 Se1 114.77(14) . . ? C8 P1 Se1 118.58(13) . . ? C1 P1 Se2 109.80(13) . . ? C8 P1 Se2 81.37(12) . . ? Se1 P1 Se2 119.35(5) . . ? C6 C1 C2 120.3(4) . . ? C6 C1 P1 120.6(3) . . ? C2 C1 P1 118.9(3) . . ? C3 C2 C1 119.8(4) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 119.8(4) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.7(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.8(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 119.6(4) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 C7 C13 131.4(4) . . ? C8 C7 Se2 107.0(3) . . ? C13 C7 Se2 121.6(3) . . ? C7 C8 C9 130.8(4) . . ? C7 C8 P1 100.9(3) . . ? C9 C8 P1 128.3(3) . . ? C8 C9 C10 109.0(3) . . ? C8 C9 C11 111.0(3) . . ? C10 C9 C11 111.0(5) . . ? C8 C9 C12 109.7(3) . . ? C10 C9 C12 109.2(4) . . ? C11 C9 C12 106.9(4) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C7 178.1(4) . . ? C13 C14 C15 176.3(4) . . ? C14 C15 C18 109.4(3) . . ? C14 C15 C17 109.2(3) . . ? C18 C15 C17 109.6(4) . . ? C14 C15 C16 108.6(3) . . ? C18 C15 C16 109.6(4) . . ? C17 C15 C16 110.4(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 C7 Se2 P1 C1 108.06(18) . . . . ? C7 Se2 P1 C8 1.59(17) . . . . ? C7 Se2 P1 Se1 -116.44(13) . . . . ? P1 Se2 C7 C8 -2.2(2) . . . . ? P1 Se2 C7 C13 177.5(3) . . . . ? C8 P1 C1 C6 -130.6(3) . . . . ? Se1 P1 C1 C6 4.5(3) . . . . ? Se2 P1 C1 C6 142.2(3) . . . . ? C8 P1 C1 C2 44.6(4) . . . . ? Se1 P1 C1 C2 179.7(3) . . . . ? Se2 P1 C1 C2 -42.6(3) . . . . ? C6 C1 C2 C3 0.2(6) . . . . ? P1 C1 C2 C3 -175.0(3) . . . . ? C13 C7 C8 C9 1.6(7) . . . . ? Se2 C7 C8 C9 -178.8(3) . . . . ? C13 C7 C8 P1 -177.0(4) . . . . ? Se2 C7 C8 P1 2.6(3) . . . . ? C1 P1 C8 C7 -110.3(3) . . . . ? Se1 P1 C8 C7 116.6(2) . . . . ? Se2 P1 C8 C7 -2.2(2) . . . . ? C1 P1 C8 C9 71.1(4) . . . . ? Se1 P1 C8 C9 -62.0(4) . . . . ? Se2 P1 C8 C9 179.2(4) . . . . ? C7 C8 C9 C10 -85.1(6) . . . . ? P1 C8 C9 C10 93.1(5) . . . . ? C7 C8 C9 C11 37.5(6) . . . . ? P1 C8 C9 C11 -144.3(4) . . . . ? C7 C8 C9 C12 155.4(4) . . . . ? P1 C8 C9 C12 -26.3(5) . . . . ? C6 C5 C4 C3 -0.5(6) . . . . ? C2 C1 C6 C5 -0.5(6) . . . . ? P1 C1 C6 C5 174.7(3) . . . . ? C4 C5 C6 C1 0.6(6) . . . . ? C1 C2 C3 C4 -0.1(7) . . . . ? C5 C4 C3 C2 0.3(7) . . . . ? _diffrn_measured_fraction_theta_max 0.797 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.948 _refine_diff_density_max 0.723 _refine_diff_density_min -0.716 _refine_diff_density_rms 0.200 # Attachment '6a.cif' data_p21n _database_code_depnum_ccdc_archive 'CCDC 629193' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H28 P2 Se4' _chemical_formula_sum 'C24 H28 P2 Se4' _chemical_formula_weight 694.24 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' P P 0.1023 0.0942 '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 11.7069(14) _cell_length_b 13.5616(17) _cell_length_c 16.717(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.424(3) _cell_angle_gamma 90.00 _cell_volume 2545.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 8858 _cell_measurement_theta_min 1.88 _cell_measurement_theta_max 27.90 _exptl_crystal_description Prism _exptl_crystal_colour Orange _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 1.811 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 5.901 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2705 _exptl_absorpt_correction_T_max 0.3849 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13526 _diffrn_reflns_av_R_equivalents 0.0728 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4253 _reflns_number_gt 3472 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+8.1521P] 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 4253 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1103 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.82870(6) 0.40682(4) 0.37813(4) 0.02718(18) Uani 1 1 d . . . Se2 Se 0.91898(5) 0.23804(4) 0.24315(3) 0.02029(16) Uani 1 1 d . . . Se11 Se 0.81802(6) 0.37553(4) -0.10807(4) 0.03205(19) Uani 1 1 d . . . Se12 Se 0.61162(5) 0.31237(5) 0.00930(3) 0.02310(17) Uani 1 1 d . . . P1 P 0.77036(12) 0.29278(10) 0.29091(8) 0.0153(3) Uani 1 1 d . . . P11 P 0.76447(13) 0.26572(10) -0.03762(9) 0.0164(3) Uani 1 1 d . . . C1 C 0.7157(5) 0.1840(4) 0.3334(3) 0.0179(12) Uani 1 1 d . . . C2 C 0.7345(5) 0.1749(4) 0.4181(4) 0.0222(13) Uani 1 1 d . . . H2 H 0.7739 0.2258 0.4546 0.027 Uiso 1 1 calc R . . C3 C 0.6953(6) 0.0905(4) 0.4501(4) 0.0270(14) Uani 1 1 d . . . H3 H 0.7082 0.0837 0.5086 0.032 Uiso 1 1 calc R . . C4 C 0.6379(5) 0.0169(4) 0.3969(4) 0.0236(13) Uani 1 1 d . . . H4 H 0.6104 -0.0402 0.4187 0.028 Uiso 1 1 calc R . . C5 C 0.6202(5) 0.0260(4) 0.3121(4) 0.0215(13) Uani 1 1 d . . . H5 H 0.5801 -0.0248 0.2757 0.026 Uiso 1 1 calc R . . C6 C 0.6606(5) 0.1086(4) 0.2796(4) 0.0185(12) Uani 1 1 d . . . H6 H 0.6508 0.1138 0.2213 0.022 Uiso 1 1 calc R . . C7 C 0.6645(5) 0.3171(4) 0.1898(3) 0.0144(11) Uani 1 1 d . . . C8 C 0.5413(5) 0.3616(4) 0.1858(3) 0.0183(12) Uani 1 1 d . . . C9 C 0.5162(6) 0.3624(6) 0.2710(4) 0.0414(18) Uani 1 1 d . . . H09A H 0.4405 0.3960 0.2662 0.062 Uiso 1 1 calc R . . H09B H 0.5806 0.3971 0.3116 0.062 Uiso 1 1 calc R . . H09C H 0.5115 0.2944 0.2898 0.062 Uiso 1 1 calc R . . C10 C 0.5373(6) 0.4686(5) 0.1549(5) 0.044(2) Uani 1 1 d . . . H10A H 0.5531 0.4698 0.1004 0.066 Uiso 1 1 calc R . . H10B H 0.5979 0.5076 0.1948 0.066 Uiso 1 1 calc R . . H10C H 0.4584 0.4966 0.1498 0.066 Uiso 1 1 calc R . . C11 C 0.4406(5) 0.3008(6) 0.1301(5) 0.0413(18) Uani 1 1 d . . . H11A H 0.3642 0.3243 0.1361 0.062 Uiso 1 1 calc R . . H11B H 0.4514 0.2313 0.1465 0.062 Uiso 1 1 calc R . . H11C H 0.4412 0.3078 0.0719 0.062 Uiso 1 1 calc R . . C12 C 0.7047(5) 0.2945(4) 0.1232(3) 0.0143(11) Uani 1 1 d . . . C13 C 0.8247(4) 0.2530(4) 0.1294(3) 0.0154(11) Uani 1 1 d . . . C14 C 0.8653(5) 0.2325(4) 0.0634(3) 0.0148(11) Uani 1 1 d . . . C15 C 0.9897(5) 0.1887(4) 0.0677(3) 0.0194(12) Uani 1 1 d . . . C16 C 1.0862(5) 0.2649(5) 0.1092(4) 0.0300(15) Uani 1 1 d . . . H16A H 1.0779 0.2827 0.1641 0.045 Uiso 1 1 calc R . . H16B H 1.0766 0.3240 0.0741 0.045 Uiso 1 1 calc R . . H16C H 1.1652 0.2364 0.1156 0.045 Uiso 1 1 calc R . . C17 C 1.0079(6) 0.0919(5) 0.1172(5) 0.0367(16) Uani 1 1 d . . . H17A H 0.9388 0.0489 0.0952 0.055 Uiso 1 1 calc R . . H17B H 1.0165 0.1061 0.1761 0.055 Uiso 1 1 calc R . . H17C H 1.0799 0.0590 0.1119 0.055 Uiso 1 1 calc R . . C18 C 1.0059(5) 0.1645(5) -0.0179(4) 0.0307(15) Uani 1 1 d . . . H18A H 1.0869 0.1399 -0.0109 0.046 Uiso 1 1 calc R . . H18B H 0.9930 0.2241 -0.0524 0.046 Uiso 1 1 calc R . . H18C H 0.9483 0.1139 -0.0451 0.046 Uiso 1 1 calc R . . C19 C 0.7192(4) 0.1507(4) -0.0945(3) 0.0174(12) Uani 1 1 d . . . C20 C 0.6841(5) 0.0700(4) -0.0540(4) 0.0222(13) Uani 1 1 d . . . H20 H 0.6797 0.0767 0.0016 0.027 Uiso 1 1 calc R . . C21 C 0.6563(5) -0.0187(5) -0.0950(4) 0.0260(13) Uani 1 1 d . . . H21 H 0.6341 -0.0736 -0.0675 0.031 Uiso 1 1 calc R . . C22 C 0.6610(5) -0.0271(4) -0.1770(3) 0.0232(13) Uani 1 1 d . . . H22 H 0.6420 -0.0882 -0.2054 0.028 Uiso 1 1 calc R . . C23 C 0.6929(5) 0.0518(4) -0.2170(3) 0.0214(13) Uani 1 1 d . . . H23 H 0.6942 0.0453 -0.2733 0.026 Uiso 1 1 calc R . . C24 C 0.7234(5) 0.1416(4) -0.1758(3) 0.0196(12) Uani 1 1 d . . . H24 H 0.7468 0.1959 -0.2034 0.023 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 0.0410(4) 0.0193(3) 0.0197(3) -0.0051(2) 0.0062(3) -0.0087(3) Se2 0.0149(3) 0.0301(3) 0.0157(3) 0.0038(2) 0.0040(2) 0.0034(2) Se11 0.0567(5) 0.0191(3) 0.0286(4) 0.0026(3) 0.0253(3) -0.0012(3) Se12 0.0212(3) 0.0337(4) 0.0139(3) 0.0002(2) 0.0041(2) 0.0121(3) P1 0.0176(7) 0.0151(7) 0.0138(7) -0.0007(5) 0.0055(6) -0.0004(6) P11 0.0213(7) 0.0158(7) 0.0141(7) 0.0005(6) 0.0084(6) 0.0035(6) C1 0.018(3) 0.012(3) 0.025(3) 0.000(2) 0.007(2) 0.005(2) C2 0.029(3) 0.018(3) 0.023(3) 0.000(2) 0.011(3) 0.001(3) C3 0.044(4) 0.023(3) 0.020(3) 0.006(3) 0.018(3) 0.004(3) C4 0.025(3) 0.011(3) 0.040(4) 0.008(3) 0.018(3) 0.003(2) C5 0.016(3) 0.010(3) 0.039(4) -0.002(2) 0.007(2) 0.004(2) C6 0.020(3) 0.013(3) 0.026(3) -0.003(2) 0.011(2) 0.005(2) C7 0.017(3) 0.011(3) 0.014(3) 0.000(2) 0.003(2) -0.002(2) C8 0.015(3) 0.017(3) 0.024(3) -0.002(2) 0.008(2) -0.001(2) C9 0.032(4) 0.067(5) 0.031(4) -0.002(3) 0.017(3) 0.022(4) C10 0.033(4) 0.019(4) 0.094(6) 0.016(4) 0.042(4) 0.013(3) C11 0.017(3) 0.061(5) 0.048(5) -0.020(4) 0.013(3) -0.012(3) C12 0.018(3) 0.011(3) 0.011(3) 0.002(2) 0.001(2) -0.001(2) C13 0.017(3) 0.012(3) 0.015(3) 0.003(2) 0.001(2) -0.001(2) C14 0.020(3) 0.010(3) 0.014(3) -0.002(2) 0.004(2) -0.002(2) C15 0.013(3) 0.022(3) 0.025(3) -0.009(2) 0.008(2) 0.000(2) C16 0.025(3) 0.041(4) 0.025(3) -0.018(3) 0.010(3) -0.007(3) C17 0.029(4) 0.029(4) 0.053(5) 0.004(3) 0.013(3) 0.014(3) C18 0.023(3) 0.039(4) 0.032(4) -0.014(3) 0.010(3) 0.005(3) C19 0.013(3) 0.024(3) 0.013(3) -0.003(2) 0.000(2) 0.005(2) C20 0.024(3) 0.024(3) 0.021(3) -0.002(2) 0.011(2) -0.005(3) C21 0.027(3) 0.028(3) 0.024(3) 0.000(3) 0.009(3) -0.003(3) C22 0.023(3) 0.023(3) 0.020(3) -0.008(2) 0.002(2) -0.001(3) C23 0.026(3) 0.026(3) 0.011(3) -0.001(2) 0.003(2) 0.007(3) C24 0.019(3) 0.021(3) 0.018(3) 0.003(2) 0.004(2) 0.004(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 P1 2.1027(15) . ? Se2 C13 1.920(5) . ? Se2 P1 2.2364(15) . ? Se11 P11 2.1012(15) . ? Se12 C12 1.923(5) . ? Se12 P11 2.2386(15) . ? P1 C7 1.821(5) . ? P1 C1 1.829(6) . ? P11 C14 1.823(5) . ? P11 C19 1.826(6) . ? C1 C2 1.376(8) . ? C1 C6 1.395(7) . ? C2 C3 1.395(8) . ? C2 H2 0.9500 . ? C3 C4 1.380(8) . ? C3 H3 0.9500 . ? C4 C5 1.379(8) . ? C4 H4 0.9500 . ? C5 C6 1.385(8) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.360(7) . ? C7 C8 1.548(7) . ? C8 C11 1.522(8) . ? C8 C9 1.534(8) . ? C8 C10 1.537(8) . ? C9 H09A 0.9800 . ? C9 H09B 0.9800 . ? C9 H09C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.489(7) . ? C13 C14 1.348(8) . ? C14 C15 1.556(7) . ? C15 C18 1.531(8) . ? C15 C17 1.534(8) . ? C15 C16 1.543(8) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C24 1.380(7) . ? C19 C20 1.407(8) . ? C20 C21 1.376(8) . ? C20 H20 0.9500 . ? C21 C22 1.392(8) . ? C21 H21 0.9500 . ? C22 C23 1.368(8) . ? C22 H22 0.9500 . ? C23 C24 1.396(8) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 Se2 P1 91.76(16) . . ? C12 Se12 P11 91.50(16) . . ? C7 P1 C1 106.6(2) . . ? C7 P1 Se1 120.87(17) . . ? C1 P1 Se1 113.85(18) . . ? C7 P1 Se2 97.04(18) . . ? C1 P1 Se2 105.30(17) . . ? Se1 P1 Se2 111.02(6) . . ? C14 P11 C19 106.7(2) . . ? C14 P11 Se11 118.51(18) . . ? C19 P11 Se11 113.75(18) . . ? C14 P11 Se12 96.74(17) . . ? C19 P11 Se12 106.29(17) . . ? Se11 P11 Se12 113.01(7) . . ? C2 C1 C6 120.6(5) . . ? C2 C1 P1 120.0(4) . . ? C6 C1 P1 119.3(4) . . ? C1 C2 C3 119.6(5) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 120.0(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.2(5) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.5(5) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 119.1(5) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? C12 C7 C8 125.9(5) . . ? C12 C7 P1 114.6(4) . . ? C8 C7 P1 119.5(4) . . ? C11 C8 C9 104.7(5) . . ? C11 C8 C10 111.2(5) . . ? C9 C8 C10 108.1(5) . . ? C11 C8 C7 111.5(5) . . ? C9 C8 C7 112.5(5) . . ? C10 C8 C7 108.8(4) . . ? C8 C9 H09A 109.5 . . ? C8 C9 H09B 109.5 . . ? H09A C9 H09B 109.5 . . ? C8 C9 H09C 109.5 . . ? H09A C9 H09C 109.5 . . ? H09B C9 H09C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C12 C13 124.4(5) . . ? C7 C12 Se12 123.5(4) . . ? C13 C12 Se12 112.1(4) . . ? C14 C13 C12 124.4(5) . . ? C14 C13 Se2 123.5(4) . . ? C12 C13 Se2 112.1(4) . . ? C13 C14 C15 125.7(5) . . ? C13 C14 P11 115.0(4) . . ? C15 C14 P11 119.3(4) . . ? C18 C15 C17 106.6(5) . . ? C18 C15 C16 107.2(5) . . ? C17 C15 C16 111.0(5) . . ? C18 C15 C14 113.7(5) . . ? C17 C15 C14 109.6(5) . . ? C16 C15 C14 108.8(4) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 120.0(5) . . ? C24 C19 P11 120.2(4) . . ? C20 C19 P11 119.7(4) . . ? C21 C20 C19 120.0(5) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 119.5(6) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C23 C22 C21 120.6(5) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 120.5(5) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C19 C24 C23 119.3(5) . . ? C19 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C13 Se2 P1 C7 -1.5(2) . . . . ? C13 Se2 P1 C1 107.8(2) . . . . ? C13 Se2 P1 Se1 -128.49(16) . . . . ? C12 Se12 P11 C14 5.0(2) . . . . ? C12 Se12 P11 C19 114.7(2) . . . . ? C12 Se12 P11 Se11 -119.89(16) . . . . ? C7 P1 C1 C2 -147.2(4) . . . . ? Se1 P1 C1 C2 -11.4(5) . . . . ? Se2 P1 C1 C2 110.4(4) . . . . ? C7 P1 C1 C6 36.1(5) . . . . ? Se1 P1 C1 C6 171.9(4) . . . . ? Se2 P1 C1 C6 -66.3(4) . . . . ? C6 C1 C2 C3 -1.6(8) . . . . ? P1 C1 C2 C3 -178.3(4) . . . . ? C1 C2 C3 C4 -0.2(9) . . . . ? C2 C3 C4 C5 0.7(9) . . . . ? C3 C4 C5 C6 0.4(8) . . . . ? C4 C5 C6 C1 -2.2(8) . . . . ? C2 C1 C6 C5 2.7(8) . . . . ? P1 C1 C6 C5 179.4(4) . . . . ? C1 P1 C7 C12 -107.2(4) . . . . ? Se1 P1 C7 C12 120.8(4) . . . . ? Se2 P1 C7 C12 1.1(4) . . . . ? C1 P1 C7 C8 73.8(4) . . . . ? Se1 P1 C7 C8 -58.2(4) . . . . ? Se2 P1 C7 C8 -177.9(4) . . . . ? C12 C7 C8 C11 53.4(7) . . . . ? P1 C7 C8 C11 -127.8(5) . . . . ? C12 C7 C8 C9 170.6(6) . . . . ? P1 C7 C8 C9 -10.5(7) . . . . ? C12 C7 C8 C10 -69.6(7) . . . . ? P1 C7 C8 C10 109.3(5) . . . . ? C8 C7 C12 C13 179.1(5) . . . . ? P1 C7 C12 C13 0.2(7) . . . . ? C8 C7 C12 Se12 -1.2(8) . . . . ? P1 C7 C12 Se12 179.8(3) . . . . ? P11 Se12 C12 C7 175.9(4) . . . . ? P11 Se12 C12 C13 -4.3(4) . . . . ? C7 C12 C13 C14 -178.7(5) . . . . ? Se12 C12 C13 C14 1.6(7) . . . . ? C7 C12 C13 Se2 -1.6(7) . . . . ? Se12 C12 C13 Se2 178.7(2) . . . . ? P1 Se2 C13 C14 178.9(5) . . . . ? P1 Se2 C13 C12 1.8(4) . . . . ? C12 C13 C14 C15 -179.7(5) . . . . ? Se2 C13 C14 C15 3.5(8) . . . . ? C12 C13 C14 P11 3.3(7) . . . . ? Se2 C13 C14 P11 -173.5(3) . . . . ? C19 P11 C14 C13 -114.8(4) . . . . ? Se11 P11 C14 C13 115.3(4) . . . . ? Se12 P11 C14 C13 -5.5(4) . . . . ? C19 P11 C14 C15 68.0(4) . . . . ? Se11 P11 C14 C15 -61.9(4) . . . . ? Se12 P11 C14 C15 177.3(4) . . . . ? C13 C14 C15 C18 174.6(5) . . . . ? P11 C14 C15 C18 -8.5(6) . . . . ? C13 C14 C15 C17 55.5(7) . . . . ? P11 C14 C15 C17 -127.7(5) . . . . ? C13 C14 C15 C16 -66.0(7) . . . . ? P11 C14 C15 C16 110.8(5) . . . . ? C14 P11 C19 C24 -131.9(4) . . . . ? Se11 P11 C19 C24 0.7(5) . . . . ? Se12 P11 C19 C24 125.7(4) . . . . ? C14 P11 C19 C20 45.8(5) . . . . ? Se11 P11 C19 C20 178.4(4) . . . . ? Se12 P11 C19 C20 -56.7(4) . . . . ? C24 C19 C20 C21 1.3(8) . . . . ? P11 C19 C20 C21 -176.4(4) . . . . ? C19 C20 C21 C22 -1.2(9) . . . . ? C20 C21 C22 C23 -0.1(9) . . . . ? C21 C22 C23 C24 1.3(9) . . . . ? C20 C19 C24 C23 -0.1(8) . . . . ? P11 C19 C24 C23 177.5(4) . . . . ? C22 C23 C24 C19 -1.1(8) . . . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 1.019 _refine_diff_density_min -0.789 _refine_diff_density_rms 0.139