Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Kilian, Petr' 'Slawin, A.' 'Woollins, Derek' _publ_contact_author_name 'Prof Derek Woollins' _publ_contact_author_address ; Prof Derek Woollins Chemistry U of St Andrews Dept of Chemistry University of St Andrews St Andrews Fife KY16 9ST UNITED KINGDOM ; _publ_contact_author_email 'JDW3@ST-AND.AC.UK' _publ_section_title 'Novel small organo-P-S/Se heterocycles' data_1 _database_code_CSD 169264 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H12 P2 S4' _chemical_formula_sum 'C13 H12 P2 S4' _chemical_formula_weight 358.41 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' 'S' 'S' 0.1246 0.1234 '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 9.8833(6) _cell_length_b 8.8370(5) _cell_length_c 18.3750(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.9480(10) _cell_angle_gamma 90.00 _cell_volume 1598.87(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 94 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max .18 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.777 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.856196 _exptl_absorpt_correction_T_max 1.000000 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6583 _diffrn_reflns_av_R_equivalents 0.0120 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 23.27 _reflns_number_total 2248 _reflns_number_gt 2034 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART/SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0338P)^2^+0.3915P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0054(12) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2248 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0262 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0597 _refine_ls_wR_factor_gt 0.0582 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 S3 S 0.33390(6) 0.76583(6) 0.12247(3) 0.05768(18) Uani 1 1 d . . . P1 P 0.30753(5) 0.58375(5) 0.17845(3) 0.03926(15) Uani 1 1 d . . . S1 S 0.45243(5) 0.58802(6) 0.27019(3) 0.05016(16) Uani 1 1 d . . . S2 S 0.35387(5) 0.43895(6) 0.33433(3) 0.04881(16) Uani 1 1 d . . . P2 P 0.16304(5) 0.54681(5) 0.31976(3) 0.04068(15) Uani 1 1 d . . . S4 S 0.03056(6) 0.41473(7) 0.35938(3) 0.06433(19) Uani 1 1 d . . . C1 C 0.14555(18) 0.5726(2) 0.22050(10) 0.0424(4) Uani 1 1 d . . . H1A H 0.0946 0.6647 0.2092 0.051 Uiso 1 1 calc R . . H1B H 0.0931 0.4889 0.1986 0.051 Uiso 1 1 calc R . . C2 C 0.32732(17) 0.4085(2) 0.12942(9) 0.0388(4) Uani 1 1 d . . . C3 C 0.2416(2) 0.2851(2) 0.13173(12) 0.0555(5) Uani 1 1 d . . . H3A H 0.1703 0.2872 0.1616 0.067 Uiso 1 1 calc R . . C4 C 0.2620(2) 0.1589(2) 0.08975(14) 0.0679(6) Uani 1 1 d . . . H4A H 0.2032 0.0769 0.0909 0.081 Uiso 1 1 calc R . . C5 C 0.3678(2) 0.1533(3) 0.04639(12) 0.0612(6) Uani 1 1 d . . . H5A H 0.3803 0.0682 0.0180 0.073 Uiso 1 1 calc R . . C6 C 0.4551(2) 0.2732(3) 0.04501(12) 0.0610(6) Uani 1 1 d . . . H6A H 0.5285 0.2682 0.0166 0.073 Uiso 1 1 calc R . . C7 C 0.4350(2) 0.4012(2) 0.08541(12) 0.0529(5) Uani 1 1 d . . . H7A H 0.4936 0.4832 0.0833 0.064 Uiso 1 1 calc R . . C8 C 0.17250(18) 0.7352(2) 0.35849(11) 0.0458(5) Uani 1 1 d . . . C9 C 0.2089(2) 0.8605(2) 0.31915(13) 0.0562(5) Uani 1 1 d . . . H9A H 0.2320 0.8491 0.2715 0.067 Uiso 1 1 calc R . . C10 C 0.2108(2) 1.0029(3) 0.35101(16) 0.0713(7) Uani 1 1 d . . . H10A H 0.2350 1.0870 0.3246 0.086 Uiso 1 1 calc R . . C11 C 0.1770(3) 1.0200(3) 0.42140(17) 0.0826(9) Uani 1 1 d . . . H11A H 0.1780 1.1157 0.4425 0.099 Uiso 1 1 calc R . . C12 C 0.1419(3) 0.8969(3) 0.46074(14) 0.0811(8) Uani 1 1 d . . . H12A H 0.1198 0.9097 0.5085 0.097 Uiso 1 1 calc R . . C13 C 0.1387(2) 0.7531(3) 0.43020(12) 0.0617(6) Uani 1 1 d . . . H13A H 0.1144 0.6698 0.4572 0.074 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 S3 0.0716(4) 0.0417(3) 0.0603(3) 0.0030(2) 0.0086(3) -0.0082(2) P1 0.0362(3) 0.0392(3) 0.0421(3) -0.0029(2) 0.00192(19) -0.00193(19) S1 0.0353(3) 0.0628(3) 0.0513(3) -0.0056(2) -0.0022(2) -0.0047(2) S2 0.0459(3) 0.0488(3) 0.0511(3) 0.0009(2) 0.0004(2) 0.0098(2) P2 0.0374(3) 0.0380(3) 0.0469(3) -0.0064(2) 0.0052(2) 0.0009(2) S4 0.0622(4) 0.0590(4) 0.0748(4) -0.0051(3) 0.0232(3) -0.0145(3) C1 0.0348(10) 0.0450(11) 0.0468(10) -0.0072(8) 0.0002(8) 0.0053(8) C2 0.0356(9) 0.0394(10) 0.0411(9) 0.0010(8) 0.0027(8) 0.0030(7) C3 0.0482(11) 0.0442(11) 0.0767(14) -0.0067(10) 0.0217(10) -0.0031(9) C4 0.0628(14) 0.0424(12) 0.0992(18) -0.0124(12) 0.0116(13) -0.0053(10) C5 0.0721(15) 0.0507(13) 0.0607(13) -0.0089(10) 0.0040(11) 0.0171(11) C6 0.0664(14) 0.0633(14) 0.0565(12) 0.0023(11) 0.0233(11) 0.0188(12) C7 0.0474(11) 0.0511(12) 0.0622(12) 0.0024(10) 0.0157(10) 0.0005(9) C8 0.0385(10) 0.0438(11) 0.0537(11) -0.0118(9) -0.0044(8) 0.0051(8) C9 0.0504(12) 0.0451(12) 0.0723(14) -0.0106(10) -0.0001(10) 0.0020(9) C10 0.0657(15) 0.0427(12) 0.102(2) -0.0151(12) -0.0131(13) 0.0035(10) C11 0.0773(17) 0.0587(16) 0.105(2) -0.0407(16) -0.0320(16) 0.0220(13) C12 0.0880(19) 0.087(2) 0.0638(15) -0.0339(15) -0.0164(13) 0.0324(15) C13 0.0655(14) 0.0651(14) 0.0530(12) -0.0148(10) -0.0040(10) 0.0181(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S3 P1 1.9394(7) . ? P1 C2 1.8104(18) . ? P1 C1 1.8394(18) . ? P1 S1 2.1160(7) . ? S1 S2 2.0667(7) . ? S2 P2 2.1095(7) . ? P2 C8 1.8099(18) . ? P2 C1 1.8314(18) . ? P2 S4 1.9419(7) . ? C2 C3 1.384(3) . ? C2 C7 1.393(3) . ? C3 C4 1.381(3) . ? C4 C5 1.370(3) . ? C5 C6 1.368(3) . ? C6 C7 1.377(3) . ? C8 C9 1.386(3) . ? C8 C13 1.396(3) . ? C9 C10 1.387(3) . ? C10 C11 1.372(4) . ? C11 C12 1.367(4) . ? C12 C13 1.389(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 P1 C1 107.36(8) . . ? C2 P1 S3 114.86(6) . . ? C1 P1 S3 115.40(6) . . ? C2 P1 S1 108.48(6) . . ? C1 P1 S1 102.71(6) . . ? S3 P1 S1 107.16(3) . . ? S2 S1 P1 97.07(3) . . ? S1 S2 P2 95.73(3) . . ? C8 P2 C1 105.93(9) . . ? C8 P2 S4 114.78(7) . . ? C1 P2 S4 116.06(7) . . ? C8 P2 S2 110.51(6) . . ? C1 P2 S2 100.90(6) . . ? S4 P2 S2 107.77(3) . . ? P2 C1 P1 114.47(9) . . ? C3 C2 C7 118.80(17) . . ? C3 C2 P1 124.48(14) . . ? C7 C2 P1 116.70(14) . . ? C4 C3 C2 120.04(19) . . ? C5 C4 C3 120.6(2) . . ? C6 C5 C4 119.8(2) . . ? C5 C6 C7 120.4(2) . . ? C6 C7 C2 120.26(19) . . ? C9 C8 C13 119.71(19) . . ? C9 C8 P2 122.44(15) . . ? C13 C8 P2 117.83(16) . . ? C8 C9 C10 119.9(2) . . ? C11 C10 C9 120.1(3) . . ? C12 C11 C10 120.3(2) . . ? C11 C12 C13 120.8(2) . . ? C12 C13 C8 119.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 P1 S1 S2 -76.24(7) . . . . ? C1 P1 S1 S2 37.22(6) . . . . ? S3 P1 S1 S2 159.21(3) . . . . ? P1 S1 S2 P2 -49.48(3) . . . . ? S1 S2 P2 C8 -64.04(8) . . . . ? S1 S2 P2 C1 47.71(7) . . . . ? S1 S2 P2 S4 169.82(3) . . . . ? C8 P2 C1 P1 89.01(11) . . . . ? S4 P2 C1 P1 -142.33(8) . . . . ? S2 P2 C1 P1 -26.21(10) . . . . ? C2 P1 C1 P2 107.46(10) . . . . ? S3 P1 C1 P2 -123.04(8) . . . . ? S1 P1 C1 P2 -6.81(10) . . . . ? C1 P1 C2 C3 -6.72(19) . . . . ? S3 P1 C2 C3 -136.53(16) . . . . ? S1 P1 C2 C3 103.62(17) . . . . ? C1 P1 C2 C7 171.77(14) . . . . ? S3 P1 C2 C7 41.96(16) . . . . ? S1 P1 C2 C7 -77.89(15) . . . . ? C7 C2 C3 C4 -1.3(3) . . . . ? P1 C2 C3 C4 177.15(17) . . . . ? C2 C3 C4 C5 1.0(4) . . . . ? C3 C4 C5 C6 0.6(4) . . . . ? C4 C5 C6 C7 -1.8(3) . . . . ? C5 C6 C7 C2 1.5(3) . . . . ? C3 C2 C7 C6 0.1(3) . . . . ? P1 C2 C7 C6 -178.49(16) . . . . ? C1 P2 C8 C9 -20.66(18) . . . . ? S4 P2 C8 C9 -150.07(15) . . . . ? S2 P2 C8 C9 87.81(16) . . . . ? C1 P2 C8 C13 157.95(15) . . . . ? S4 P2 C8 C13 28.53(17) . . . . ? S2 P2 C8 C13 -93.58(16) . . . . ? C13 C8 C9 C10 -0.4(3) . . . . ? P2 C8 C9 C10 178.21(16) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? C9 C10 C11 C12 0.3(4) . . . . ? C10 C11 C12 C13 -0.5(4) . . . . ? C11 C12 C13 C8 0.2(4) . . . . ? C9 C8 C13 C12 0.2(3) . . . . ? P2 C8 C13 C12 -178.45(17) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.206 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.031 data_2 _database_code_CSD 169265 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H12 P2 Se4' _chemical_formula_sum 'C13 H12 P2 Se4' _chemical_formula_weight 546.01 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)/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 10.0165(14) _cell_length_b 8.9836(5) _cell_length_c 18.677(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.6870(10) _cell_angle_gamma 90.00 _cell_volume 1677.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 57 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max .21 _exptl_crystal_size_mid .15 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 8.924 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.32768 _exptl_absorpt_correction_T_max 1.00000 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8916 _diffrn_reflns_av_R_equivalents 0.1387 _diffrn_reflns_av_sigmaI/netI 0.1053 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 28.49 _reflns_number_total 3431 _reflns_number_gt 2598 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0022(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3431 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1059 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.1516 _refine_ls_wR_factor_gt 0.1347 _refine_ls_goodness_of_fit_ref 1.160 _refine_ls_restrained_S_all 1.160 _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 Se3 Se 0.17744(8) 0.19971(9) 0.38466(4) 0.0488(3) Uani 1 1 d . . . P1 P 0.19215(18) 0.3925(2) 0.32212(9) 0.0364(4) Uani 1 1 d . . . Se1 Se 0.03068(7) 0.37750(10) 0.23300(4) 0.0463(3) Uani 1 1 d . . . Se2 Se 0.13615(8) 0.54749(9) 0.16048(4) 0.0453(3) Uani 1 1 d . . . P2 P 0.33414(18) 0.4316(2) 0.17920(9) 0.0371(4) Uani 1 1 d . . . Se4 Se 0.48142(10) 0.56727(11) 0.13771(5) 0.0597(3) Uani 1 1 d . . . C1 C 0.3486(7) 0.4087(8) 0.2772(3) 0.0371(16) Uani 1 1 d . . . H1A H 0.4017 0.3204 0.2883 0.045 Uiso 1 1 calc R . . H1B H 0.3979 0.4931 0.2977 0.045 Uiso 1 1 calc R . . C2 C 0.1710(7) 0.5640(8) 0.3710(3) 0.0339(15) Uani 1 1 d . . . C3 C 0.2617(9) 0.6792(9) 0.3757(5) 0.054(2) Uani 1 1 d . . . H3A H 0.3387 0.6749 0.3505 0.064 Uiso 1 1 calc R . . C4 C 0.2379(11) 0.8008(11) 0.4178(5) 0.070(3) Uani 1 1 d . . . H4A H 0.3002 0.8777 0.4209 0.084 Uiso 1 1 calc R . . C5 C 0.1262(10) 0.8119(10) 0.4549(4) 0.059(2) Uani 1 1 d . . . H5A H 0.1118 0.8949 0.4831 0.071 Uiso 1 1 calc R . . C6 C 0.0347(10) 0.6972(11) 0.4497(4) 0.064(2) Uani 1 1 d . . . H6A H -0.0425 0.7031 0.4747 0.076 Uiso 1 1 calc R . . C7 C 0.0556(8) 0.5751(9) 0.4085(4) 0.0488(19) Uani 1 1 d . . . H7A H -0.0074 0.4990 0.4055 0.059 Uiso 1 1 calc R . . C8 C 0.3264(7) 0.2438(9) 0.1414(4) 0.0407(16) Uani 1 1 d . . . C9 C 0.3001(9) 0.1218(10) 0.1824(5) 0.057(2) Uani 1 1 d . . . H9A H 0.2818 0.1341 0.2303 0.068 Uiso 1 1 calc R . . C10 C 0.3006(8) -0.0200(11) 0.1528(5) 0.060(2) Uani 1 1 d . . . H10A H 0.2819 -0.1026 0.1804 0.072 Uiso 1 1 calc R . . C11 C 0.3283(11) -0.0368(12) 0.0838(7) 0.080(3) Uani 1 1 d . . . H11A H 0.3292 -0.1315 0.0638 0.096 Uiso 1 1 calc R . . C12 C 0.3558(11) 0.0865(12) 0.0419(5) 0.069(3) Uani 1 1 d . . . H12A H 0.3747 0.0731 -0.0057 0.083 Uiso 1 1 calc R . . C13 C 0.3553(9) 0.2282(11) 0.0704(4) 0.059(2) Uani 1 1 d . . . H13B H 0.3738 0.3108 0.0426 0.071 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 Se3 0.0558(5) 0.0386(5) 0.0522(5) 0.0027(4) 0.0055(4) -0.0010(4) P1 0.0337(9) 0.0384(11) 0.0371(9) -0.0026(8) 0.0016(7) 0.0011(8) Se1 0.0359(4) 0.0559(6) 0.0466(4) -0.0041(4) -0.0020(3) -0.0041(4) Se2 0.0457(4) 0.0422(5) 0.0477(4) 0.0009(3) 0.0008(3) 0.0073(4) P2 0.0371(9) 0.0344(10) 0.0400(9) -0.0042(8) 0.0043(7) 0.0016(8) Se4 0.0604(5) 0.0529(6) 0.0681(6) -0.0035(4) 0.0213(4) -0.0140(4) C1 0.041(4) 0.034(4) 0.036(3) -0.008(3) -0.002(3) 0.002(3) C2 0.035(3) 0.032(4) 0.035(3) 0.005(3) 0.001(3) 0.003(3) C3 0.051(5) 0.038(4) 0.073(5) -0.012(4) 0.024(4) -0.007(4) C4 0.076(6) 0.038(5) 0.098(7) -0.012(5) 0.026(6) -0.010(5) C5 0.082(6) 0.038(5) 0.057(5) -0.010(4) -0.001(5) 0.011(5) C6 0.072(6) 0.069(6) 0.051(4) -0.006(5) 0.016(4) 0.023(6) C7 0.049(4) 0.043(5) 0.054(4) -0.004(4) 0.004(4) -0.002(4) C8 0.036(4) 0.032(4) 0.054(4) -0.005(4) 0.002(3) 0.002(3) C9 0.057(5) 0.040(5) 0.073(5) -0.005(4) 0.001(4) 0.002(4) C10 0.057(5) 0.038(5) 0.083(6) -0.013(5) 0.003(5) 0.004(4) C11 0.077(7) 0.043(6) 0.116(9) -0.029(6) -0.023(7) 0.015(5) C12 0.082(7) 0.068(7) 0.055(5) -0.028(5) -0.016(5) 0.020(6) C13 0.061(5) 0.065(6) 0.049(4) -0.006(4) -0.007(4) 0.016(5) _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 Se3 P1 2.100(2) . ? P1 C2 1.809(7) . ? P1 C1 1.830(7) . ? P1 Se1 2.2491(19) . ? Se1 Se2 2.3381(11) . ? Se2 P2 2.247(2) . ? P2 C8 1.828(8) . ? P2 C1 1.839(6) . ? P2 Se4 2.100(2) . ? C2 C3 1.377(11) . ? C2 C7 1.394(11) . ? C3 C4 1.376(12) . ? C4 C5 1.356(14) . ? C5 C6 1.379(13) . ? C6 C7 1.363(12) . ? C8 C9 1.373(12) . ? C8 C13 1.382(11) . ? C9 C10 1.389(12) . ? C10 C11 1.344(14) . ? C11 C12 1.393(15) . ? C12 C13 1.380(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 P1 C1 107.2(3) . . ? C2 P1 Se3 114.0(2) . . ? C1 P1 Se3 114.4(2) . . ? C2 P1 Se1 108.8(2) . . ? C1 P1 Se1 105.2(2) . . ? Se3 P1 Se1 106.82(9) . . ? P1 Se1 Se2 93.40(6) . . ? P2 Se2 Se1 91.97(6) . . ? C8 P2 C1 106.3(3) . . ? C8 P2 Se4 114.0(2) . . ? C1 P2 Se4 114.8(2) . . ? C8 P2 Se2 110.6(2) . . ? C1 P2 Se2 102.7(2) . . ? Se4 P2 Se2 107.91(9) . . ? P1 C1 P2 116.7(4) . . ? C3 C2 C7 118.6(7) . . ? C3 C2 P1 125.0(6) . . ? C7 C2 P1 116.3(6) . . ? C4 C3 C2 119.7(8) . . ? C5 C4 C3 121.9(9) . . ? C4 C5 C6 118.4(8) . . ? C7 C6 C5 121.0(9) . . ? C6 C7 C2 120.3(8) . . ? C9 C8 C13 121.0(8) . . ? C9 C8 P2 121.7(6) . . ? C13 C8 P2 117.3(6) . . ? C8 C9 C10 120.2(8) . . ? C11 C10 C9 119.5(9) . . ? C10 C11 C12 120.6(9) . . ? C13 C12 C11 120.8(9) . . ? C12 C13 C8 118.0(9) . . ? 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 C2 P1 Se1 Se2 77.1(2) . . . . ? C1 P1 Se1 Se2 -37.4(3) . . . . ? Se3 P1 Se1 Se2 -159.39(7) . . . . ? P1 Se1 Se2 P2 47.44(7) . . . . ? Se1 Se2 P2 C8 64.7(3) . . . . ? Se1 Se2 P2 C1 -48.4(2) . . . . ? Se1 Se2 P2 Se4 -170.05(7) . . . . ? C2 P1 C1 P2 -108.5(4) . . . . ? Se3 P1 C1 P2 124.1(3) . . . . ? Se1 P1 C1 P2 7.2(5) . . . . ? C8 P2 C1 P1 -87.4(5) . . . . ? Se4 P2 C1 P1 145.6(3) . . . . ? Se2 P2 C1 P1 28.8(4) . . . . ? C1 P1 C2 C3 -3.4(7) . . . . ? Se3 P1 C2 C3 124.3(6) . . . . ? Se1 P1 C2 C3 -116.6(6) . . . . ? C1 P1 C2 C7 179.2(5) . . . . ? Se3 P1 C2 C7 -53.2(6) . . . . ? Se1 P1 C2 C7 65.9(6) . . . . ? C7 C2 C3 C4 1.0(12) . . . . ? P1 C2 C3 C4 -176.4(7) . . . . ? C2 C3 C4 C5 -0.6(14) . . . . ? C3 C4 C5 C6 0.0(15) . . . . ? C4 C5 C6 C7 0.2(13) . . . . ? C5 C6 C7 C2 0.3(12) . . . . ? C3 C2 C7 C6 -0.9(11) . . . . ? P1 C2 C7 C6 176.7(6) . . . . ? C1 P2 C8 C9 15.5(7) . . . . ? Se4 P2 C8 C9 143.0(6) . . . . ? Se2 P2 C8 C9 -95.2(6) . . . . ? C1 P2 C8 C13 -161.1(6) . . . . ? Se4 P2 C8 C13 -33.6(6) . . . . ? Se2 P2 C8 C13 88.2(6) . . . . ? C13 C8 C9 C10 -0.7(12) . . . . ? P2 C8 C9 C10 -177.2(6) . . . . ? C8 C9 C10 C11 0.6(13) . . . . ? C9 C10 C11 C12 -0.3(14) . . . . ? C10 C11 C12 C13 0.1(16) . . . . ? C11 C12 C13 C8 -0.2(14) . . . . ? C9 C8 C13 C12 0.5(12) . . . . ? P2 C8 C13 C12 177.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.810 _diffrn_reflns_theta_full 28.49 _diffrn_measured_fraction_theta_full 0.810 _refine_diff_density_max 0.636 _refine_diff_density_min -0.819 _refine_diff_density_rms 0.148 data_3 _database_code_CSD 169266 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H16 P2 Se3' _chemical_formula_sum 'C15 H16 P2 Se3' _chemical_formula_weight 495.10 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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 17.7582(3) _cell_length_b 27.4561(2) _cell_length_c 7.15120(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3486.72(8) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 145 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max .28 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.886 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1904 _exptl_absorpt_coefficient_mu 6.501 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.575233 _exptl_absorpt_correction_T_max 1.000000 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 0.9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14800 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 23.26 _reflns_number_total 4850 _reflns_number_gt 3875 _reflns_threshold_expression >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART/SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0266P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00034(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.055(11) _refine_ls_number_reflns 4850 _refine_ls_number_parameters 362 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0631 _refine_ls_wR_factor_gt 0.0592 _refine_ls_goodness_of_fit_ref 0.917 _refine_ls_restrained_S_all 0.917 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.001 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 Se3 Se 0.81599(4) 0.41251(3) 0.63740(13) 0.0508(2) Uani 1 1 d . . . P1 P 0.71084(10) 0.39735(7) 0.7571(3) 0.0319(5) Uani 1 1 d . . . Se1 Se 0.67499(4) 0.31782(3) 0.77713(10) 0.03372(18) Uani 1 1 d . . . P2 P 0.70116(10) 0.33653(7) 1.0813(3) 0.0308(5) Uani 1 1 d . . . Se2 Se 0.62194(4) 0.31839(3) 1.28807(12) 0.0424(2) Uani 1 1 d . . . C1 C 0.7076(3) 0.4043(2) 1.0235(10) 0.0261(16) Uani 1 1 d . . . C2 C 0.6327(4) 0.4290(3) 1.0778(11) 0.047(2) Uani 1 1 d . . . H2A H 0.5915 0.4112 1.0240 0.070 Uiso 1 1 calc R . . H2B H 0.6323 0.4618 1.0318 0.070 Uiso 1 1 calc R . . H2C H 0.6278 0.4293 1.2115 0.070 Uiso 1 1 calc R . . C3 C 0.7730(4) 0.4288(2) 1.0985(11) 0.047(2) Uani 1 1 d . . . H3A H 0.8177 0.4119 1.0603 0.070 Uiso 1 1 calc R . . H3B H 0.7701 0.4292 1.2325 0.070 Uiso 1 1 calc R . . H3C H 0.7746 0.4616 1.0525 0.070 Uiso 1 1 calc R . . C4 C 0.6350(4) 0.4324(3) 0.6493(10) 0.0332(18) Uani 1 1 d . . . C5 C 0.6496(4) 0.4787(3) 0.5832(10) 0.044(2) Uani 1 1 d . . . H5A H 0.6979 0.4915 0.5939 0.053 Uiso 1 1 calc R . . C6 C 0.5943(5) 0.5060(3) 0.5025(13) 0.055(2) Uani 1 1 d . . . H6A H 0.6046 0.5375 0.4627 0.066 Uiso 1 1 calc R . . C7 C 0.5234(5) 0.4868(3) 0.4800(13) 0.061(2) Uani 1 1 d . . . H7A H 0.4859 0.5053 0.4239 0.073 Uiso 1 1 calc R . . C8 C 0.5077(4) 0.4403(3) 0.5400(12) 0.057(2) Uani 1 1 d . . . H8A H 0.4598 0.4271 0.5242 0.068 Uiso 1 1 calc R . . C9 C 0.5639(4) 0.4135(3) 0.6239(11) 0.0393(18) Uani 1 1 d . . . H9A H 0.5536 0.3820 0.6642 0.047 Uiso 1 1 calc R . . C10 C 0.7950(4) 0.3137(2) 1.1324(12) 0.0325(17) Uani 1 1 d . . . C11 C 0.8496(4) 0.3099(2) 0.9959(13) 0.0463(19) Uani 1 1 d . . . H11A H 0.8376 0.3182 0.8735 0.056 Uiso 1 1 calc R . . C12 C 0.9214(4) 0.2941(3) 1.0360(15) 0.057(3) Uani 1 1 d . . . H12A H 0.9576 0.2919 0.9423 0.069 Uiso 1 1 calc R . . C13 C 0.9389(5) 0.2814(3) 1.2194(16) 0.061(3) Uani 1 1 d . . . H13A H 0.9868 0.2702 1.2492 0.073 Uiso 1 1 calc R . . C14 C 0.8861(5) 0.2854(3) 1.3531(13) 0.055(2) Uani 1 1 d . . . H14A H 0.8987 0.2776 1.4757 0.066 Uiso 1 1 calc R . . C15 C 0.8130(4) 0.3010(3) 1.3139(12) 0.041(2) Uani 1 1 d . . . H15A H 0.7770 0.3027 1.4082 0.049 Uiso 1 1 calc R . . Se23 Se 0.78352(5) 0.07343(3) 0.40704(12) 0.0490(2) Uani 1 1 d . . . P21 P 0.68375(10) 0.10602(6) 0.4980(3) 0.0330(4) Uani 1 1 d . . . Se21 Se 0.67674(4) 0.18888(2) 0.49433(11) 0.0394(2) Uani 1 1 d . . . P22 P 0.70069(10) 0.17057(6) 0.7987(3) 0.0323(5) Uani 1 1 d . . . Se22 Se 0.64343(4) 0.21019(3) 1.00556(13) 0.0468(2) Uani 1 1 d . . . C21 C 0.6695(4) 0.1059(2) 0.7590(11) 0.0333(17) Uani 1 1 d . . . C22 C 0.5874(4) 0.1014(3) 0.8140(11) 0.053(2) Uani 1 1 d . . . H22A H 0.5587 0.1263 0.7522 0.079 Uiso 1 1 calc R . . H22B H 0.5826 0.1051 0.9469 0.079 Uiso 1 1 calc R . . H22C H 0.5688 0.0700 0.7776 0.079 Uiso 1 1 calc R . . C23 C 0.7157(5) 0.0672(3) 0.8553(11) 0.050(2) Uani 1 1 d . . . H23A H 0.7677 0.0708 0.8208 0.075 Uiso 1 1 calc R . . H23B H 0.6981 0.0356 0.8182 0.075 Uiso 1 1 calc R . . H23C H 0.7108 0.0707 0.9883 0.075 Uiso 1 1 calc R . . C24 C 0.6004(4) 0.0820(3) 0.3796(10) 0.0308(18) Uani 1 1 d . . . C25 C 0.6026(4) 0.0356(3) 0.3071(11) 0.0368(19) Uani 1 1 d . . . H25A H 0.6466 0.0174 0.3158 0.044 Uiso 1 1 calc R . . C26 C 0.5394(4) 0.0157(3) 0.2207(11) 0.048(2) Uani 1 1 d . . . H26A H 0.5412 -0.0156 0.1710 0.057 Uiso 1 1 calc R . . C27 C 0.4742(4) 0.0428(3) 0.2095(11) 0.047(2) Uani 1 1 d . . . H27A H 0.4317 0.0299 0.1520 0.057 Uiso 1 1 calc R . . C28 C 0.4723(4) 0.0887(3) 0.2834(12) 0.0442(19) Uani 1 1 d . . . H28A H 0.4279 0.1066 0.2770 0.053 Uiso 1 1 calc R . . C29 C 0.5342(4) 0.1088(3) 0.3667(10) 0.039(2) Uani 1 1 d . . . H29A H 0.5320 0.1402 0.4145 0.047 Uiso 1 1 calc R . . C30 C 0.8025(4) 0.1725(2) 0.8324(10) 0.036(2) Uani 1 1 d . . . C31 C 0.8532(4) 0.1821(3) 0.6885(12) 0.048(2) Uani 1 1 d . . . H31A H 0.8363 0.1872 0.5670 0.058 Uiso 1 1 calc R . . C32 C 0.9284(5) 0.1836(3) 0.7304(13) 0.059(3) Uani 1 1 d . . . H32A H 0.9624 0.1912 0.6359 0.070 Uiso 1 1 calc R . . C33 C 0.9549(5) 0.1746(3) 0.9036(14) 0.056(2) Uani 1 1 d . . . H33A H 1.0065 0.1754 0.9268 0.067 Uiso 1 1 calc R . . C34 C 0.9053(5) 0.1642(3) 1.0456(13) 0.058(3) Uani 1 1 d . . . H34A H 0.9239 0.1574 1.1644 0.070 Uiso 1 1 calc R . . C35 C 0.8282(4) 0.1638(3) 1.0152(13) 0.052(2) Uani 1 1 d . . . H35A H 0.7946 0.1579 1.1124 0.062 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 Se3 0.0403(5) 0.0618(6) 0.0502(5) 0.0022(5) 0.0069(4) -0.0087(4) P1 0.0327(10) 0.0334(11) 0.0297(12) 0.0009(10) -0.0024(10) -0.0023(8) Se1 0.0398(4) 0.0331(4) 0.0283(4) -0.0035(4) 0.0002(4) -0.0008(4) P2 0.0308(11) 0.0343(11) 0.0273(12) -0.0012(9) 0.0012(9) 0.0039(8) Se2 0.0425(4) 0.0506(5) 0.0340(5) 0.0001(5) 0.0095(4) -0.0008(4) C1 0.024(3) 0.030(4) 0.025(4) 0.015(3) -0.001(3) 0.002(3) C2 0.058(5) 0.051(5) 0.031(5) -0.007(4) 0.000(4) 0.016(4) C3 0.069(6) 0.025(4) 0.047(6) -0.006(4) -0.006(5) 0.005(4) C4 0.039(5) 0.038(5) 0.023(4) -0.001(4) -0.003(4) 0.008(4) C5 0.051(5) 0.036(5) 0.047(6) 0.002(4) 0.001(4) 0.002(4) C6 0.067(6) 0.043(5) 0.054(6) 0.022(5) 0.004(6) 0.017(5) C7 0.074(7) 0.069(6) 0.040(6) 0.000(5) -0.002(6) 0.038(5) C8 0.044(5) 0.072(7) 0.055(6) -0.008(5) -0.019(5) 0.007(5) C9 0.039(5) 0.038(5) 0.041(5) 0.001(4) -0.005(4) -0.006(4) C10 0.035(4) 0.024(4) 0.038(5) 0.002(4) 0.000(4) -0.004(3) C11 0.043(4) 0.054(5) 0.042(5) -0.009(5) -0.004(5) 0.012(4) C12 0.039(5) 0.060(6) 0.072(8) -0.010(6) 0.017(5) 0.011(4) C13 0.040(5) 0.054(6) 0.089(8) 0.009(5) -0.007(6) 0.008(4) C14 0.061(6) 0.044(5) 0.060(7) 0.014(4) -0.015(5) 0.000(5) C15 0.039(5) 0.045(5) 0.037(6) 0.006(4) 0.000(4) -0.002(4) Se23 0.0407(5) 0.0552(5) 0.0511(6) -0.0064(5) -0.0013(5) 0.0078(4) P21 0.0357(10) 0.0326(10) 0.0307(11) 0.0008(10) -0.0032(11) 0.0008(9) Se21 0.0462(4) 0.0344(4) 0.0378(5) 0.0039(4) -0.0037(5) 0.0005(4) P22 0.0341(10) 0.0316(11) 0.0311(11) -0.0026(10) -0.0010(10) -0.0034(8) Se22 0.0505(5) 0.0469(4) 0.0430(5) -0.0094(5) 0.0083(5) -0.0004(4) C21 0.043(4) 0.026(4) 0.031(4) 0.000(4) -0.017(4) -0.006(3) C22 0.069(6) 0.047(5) 0.042(5) 0.004(4) 0.018(4) -0.022(4) C23 0.073(6) 0.036(5) 0.042(6) 0.008(4) 0.000(4) -0.003(4) C24 0.031(4) 0.034(5) 0.027(4) 0.010(4) -0.008(4) -0.003(3) C25 0.040(4) 0.034(4) 0.037(5) 0.002(4) -0.003(4) 0.001(3) C26 0.047(5) 0.042(5) 0.054(6) -0.002(4) -0.002(4) -0.009(4) C27 0.042(5) 0.046(6) 0.054(6) -0.005(4) -0.004(4) -0.010(4) C28 0.035(4) 0.050(5) 0.048(5) 0.002(5) 0.001(5) 0.006(4) C29 0.040(5) 0.042(5) 0.037(5) -0.007(4) -0.005(4) -0.002(4) C30 0.042(5) 0.030(4) 0.036(5) 0.002(4) -0.003(4) -0.001(3) C31 0.028(5) 0.064(6) 0.052(6) -0.011(5) 0.002(4) -0.002(4) C32 0.042(5) 0.080(7) 0.055(7) -0.004(5) 0.013(5) 0.013(5) C33 0.036(5) 0.063(6) 0.069(7) -0.017(5) -0.006(5) 0.001(4) C34 0.055(6) 0.072(6) 0.048(6) 0.005(5) -0.022(5) 0.018(5) C35 0.036(5) 0.075(6) 0.045(6) 0.003(5) -0.008(5) -0.009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se3 P1 2.0959(19) . ? P1 C4 1.825(7) . ? P1 C1 1.915(7) . ? P1 Se1 2.2790(19) . ? Se1 P2 2.283(2) . ? P2 C10 1.817(7) . ? P2 C1 1.910(6) . ? P2 Se2 2.101(2) . ? C1 C3 1.444(9) . ? C1 C2 1.542(9) . ? C4 C9 1.377(9) . ? C4 C5 1.381(9) . ? C5 C6 1.363(10) . ? C6 C7 1.375(10) . ? C7 C8 1.375(11) . ? C8 C9 1.377(9) . ? C10 C11 1.379(11) . ? C10 C15 1.382(10) . ? C11 C12 1.378(10) . ? C12 C13 1.391(12) . ? C13 C14 1.344(11) . ? C14 C15 1.395(10) . ? Se23 P21 2.089(2) . ? P21 C24 1.829(7) . ? P21 C21 1.883(8) . ? P21 Se21 2.2784(19) . ? Se21 P22 2.274(2) . ? P22 C30 1.826(7) . ? P22 C21 1.880(6) . ? P22 Se22 2.099(2) . ? C21 C23 1.509(9) . ? C21 C22 1.516(9) . ? C24 C25 1.375(9) . ? C24 C29 1.390(9) . ? C25 C26 1.392(10) . ? C26 C27 1.379(10) . ? C27 C28 1.367(9) . ? C28 C29 1.367(9) . ? C30 C31 1.391(10) . ? C30 C35 1.405(10) . ? C31 C32 1.370(10) . ? C32 C33 1.348(11) . ? C33 C34 1.374(11) . ? C34 C35 1.388(10) . ? 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 C4 P1 C1 110.2(3) . . ? C4 P1 Se3 112.3(2) . . ? C1 P1 Se3 114.4(2) . . ? C4 P1 Se1 109.0(2) . . ? C1 P1 Se1 91.4(2) . . ? Se3 P1 Se1 117.70(9) . . ? P1 Se1 P2 77.73(7) . . ? C10 P2 C1 108.9(3) . . ? C10 P2 Se2 113.0(3) . . ? C1 P2 Se2 115.1(2) . . ? C10 P2 Se1 107.5(3) . . ? C1 P2 Se1 91.4(2) . . ? Se2 P2 Se1 118.74(9) . . ? C3 C1 C2 113.2(6) . . ? C3 C1 P2 114.9(5) . . ? C2 C1 P2 108.8(4) . . ? C3 C1 P1 113.1(5) . . ? C2 C1 P1 108.7(5) . . ? P2 C1 P1 96.9(3) . . ? C9 C4 C5 118.2(7) . . ? C9 C4 P1 122.3(6) . . ? C5 C4 P1 119.4(6) . . ? C6 C5 C4 121.1(7) . . ? C5 C6 C7 119.9(8) . . ? C8 C7 C6 120.4(7) . . ? C7 C8 C9 118.9(8) . . ? C4 C9 C8 121.5(7) . . ? C11 C10 C15 118.9(7) . . ? C11 C10 P2 121.9(6) . . ? C15 C10 P2 119.2(6) . . ? C12 C11 C10 121.8(9) . . ? C11 C12 C13 118.7(9) . . ? C14 C13 C12 119.7(8) . . ? C13 C14 C15 122.1(8) . . ? C10 C15 C14 118.8(7) . . ? C24 P21 C21 110.5(3) . . ? C24 P21 Se23 112.8(3) . . ? C21 P21 Se23 114.9(2) . . ? C24 P21 Se21 108.1(2) . . ? C21 P21 Se21 90.3(2) . . ? Se23 P21 Se21 118.07(9) . . ? P22 Se21 P21 75.99(7) . . ? C30 P22 C21 109.8(3) . . ? C30 P22 Se22 111.8(2) . . ? C21 P22 Se22 116.9(2) . . ? C30 P22 Se21 107.8(2) . . ? C21 P22 Se21 90.5(2) . . ? Se22 P22 Se21 118.00(9) . . ? C23 C21 C22 110.3(6) . . ? C23 C21 P22 115.8(5) . . ? C22 C21 P22 108.7(5) . . ? C23 C21 P21 112.4(5) . . ? C22 C21 P21 112.7(5) . . ? P22 C21 P21 96.3(3) . . ? C25 C24 C29 119.3(6) . . ? C25 C24 P21 119.1(5) . . ? C29 C24 P21 121.6(6) . . ? C24 C25 C26 120.5(7) . . ? C27 C26 C25 119.4(8) . . ? C28 C27 C26 119.7(7) . . ? C27 C28 C29 121.4(7) . . ? C28 C29 C24 119.7(7) . . ? C31 C30 C35 120.7(7) . . ? C31 C30 P22 123.2(6) . . ? C35 C30 P22 116.0(6) . . ? C32 C31 C30 118.3(8) . . ? C33 C32 C31 122.4(8) . . ? C32 C33 C34 119.5(7) . . ? C33 C34 C35 121.3(8) . . ? C34 C35 C30 117.6(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 C4 P1 Se1 P2 -123.0(2) . . . . ? C1 P1 Se1 P2 -11.0(2) . . . . ? Se3 P1 Se1 P2 107.61(11) . . . . ? P1 Se1 P2 C10 -99.3(2) . . . . ? P1 Se1 P2 C1 11.1(2) . . . . ? P1 Se1 P2 Se2 130.88(10) . . . . ? C10 P2 C1 C3 -23.4(6) . . . . ? Se2 P2 C1 C3 104.7(5) . . . . ? Se1 P2 C1 C3 -132.4(5) . . . . ? C10 P2 C1 C2 -151.5(5) . . . . ? Se2 P2 C1 C2 -23.4(5) . . . . ? Se1 P2 C1 C2 99.5(5) . . . . ? C10 P2 C1 P1 96.1(4) . . . . ? Se2 P2 C1 P1 -135.86(19) . . . . ? Se1 P2 C1 P1 -13.0(2) . . . . ? C4 P1 C1 C3 -115.3(5) . . . . ? Se3 P1 C1 C3 12.4(5) . . . . ? Se1 P1 C1 C3 133.9(4) . . . . ? C4 P1 C1 C2 11.4(5) . . . . ? Se3 P1 C1 C2 139.1(4) . . . . ? Se1 P1 C1 C2 -99.5(4) . . . . ? C4 P1 C1 P2 123.9(3) . . . . ? Se3 P1 C1 P2 -108.4(2) . . . . ? Se1 P1 C1 P2 13.0(2) . . . . ? C1 P1 C4 C9 -86.9(7) . . . . ? Se3 P1 C4 C9 144.3(6) . . . . ? Se1 P1 C4 C9 12.0(7) . . . . ? C1 P1 C4 C5 95.9(6) . . . . ? Se3 P1 C4 C5 -32.9(7) . . . . ? Se1 P1 C4 C5 -165.2(5) . . . . ? C9 C4 C5 C6 3.0(12) . . . . ? P1 C4 C5 C6 -179.8(6) . . . . ? C4 C5 C6 C7 -2.3(13) . . . . ? C5 C6 C7 C8 0.6(14) . . . . ? C6 C7 C8 C9 0.4(13) . . . . ? C5 C4 C9 C8 -1.9(12) . . . . ? P1 C4 C9 C8 -179.1(6) . . . . ? C7 C8 C9 C4 0.3(12) . . . . ? C1 P2 C10 C11 -68.6(6) . . . . ? Se2 P2 C10 C11 162.1(5) . . . . ? Se1 P2 C10 C11 29.2(6) . . . . ? C1 P2 C10 C15 109.7(6) . . . . ? Se2 P2 C10 C15 -19.5(6) . . . . ? Se1 P2 C10 C15 -152.5(5) . . . . ? C15 C10 C11 C12 -0.5(11) . . . . ? P2 C10 C11 C12 177.9(6) . . . . ? C10 C11 C12 C13 0.3(12) . . . . ? C11 C12 C13 C14 -0.9(13) . . . . ? C12 C13 C14 C15 1.5(13) . . . . ? C11 C10 C15 C14 1.1(10) . . . . ? P2 C10 C15 C14 -177.4(5) . . . . ? C13 C14 C15 C10 -1.6(12) . . . . ? C24 P21 Se21 P22 129.8(3) . . . . ? C21 P21 Se21 P22 18.1(2) . . . . ? Se23 P21 Se21 P22 -100.68(11) . . . . ? P21 Se21 P22 C30 93.0(2) . . . . ? P21 Se21 P22 C21 -18.1(2) . . . . ? P21 Se21 P22 Se22 -139.29(10) . . . . ? C30 P22 C21 C23 31.0(7) . . . . ? Se22 P22 C21 C23 -97.8(6) . . . . ? Se21 P22 C21 C23 140.1(6) . . . . ? C30 P22 C21 C22 155.8(5) . . . . ? Se22 P22 C21 C22 27.0(6) . . . . ? Se21 P22 C21 C22 -95.0(5) . . . . ? C30 P22 C21 P21 -87.6(4) . . . . ? Se22 P22 C21 P21 143.6(2) . . . . ? Se21 P22 C21 P21 21.5(2) . . . . ? C24 P21 C21 C23 107.7(5) . . . . ? Se23 P21 C21 C23 -21.3(6) . . . . ? Se21 P21 C21 C23 -142.8(5) . . . . ? C24 P21 C21 C22 -17.7(6) . . . . ? Se23 P21 C21 C22 -146.7(4) . . . . ? Se21 P21 C21 C22 91.8(5) . . . . ? C24 P21 C21 P22 -131.0(3) . . . . ? Se23 P21 C21 P22 100.0(3) . . . . ? Se21 P21 C21 P22 -21.5(2) . . . . ? C21 P21 C24 C25 -104.6(6) . . . . ? Se23 P21 C24 C25 25.6(6) . . . . ? Se21 P21 C24 C25 158.1(5) . . . . ? C21 P21 C24 C29 73.2(7) . . . . ? Se23 P21 C24 C29 -156.6(5) . . . . ? Se21 P21 C24 C29 -24.2(7) . . . . ? C29 C24 C25 C26 0.4(11) . . . . ? P21 C24 C25 C26 178.2(6) . . . . ? C24 C25 C26 C27 -0.5(11) . . . . ? C25 C26 C27 C28 -0.1(12) . . . . ? C26 C27 C28 C29 0.8(12) . . . . ? C27 C28 C29 C24 -1.0(12) . . . . ? C25 C24 C29 C28 0.4(11) . . . . ? P21 C24 C29 C28 -177.4(6) . . . . ? C21 P22 C30 C31 95.1(7) . . . . ? Se22 P22 C30 C31 -133.4(6) . . . . ? Se21 P22 C30 C31 -2.2(7) . . . . ? C21 P22 C30 C35 -84.9(6) . . . . ? Se22 P22 C30 C35 46.6(6) . . . . ? Se21 P22 C30 C35 177.9(5) . . . . ? C35 C30 C31 C32 -1.3(12) . . . . ? P22 C30 C31 C32 178.7(6) . . . . ? C30 C31 C32 C33 2.4(13) . . . . ? C31 C32 C33 C34 -1.1(14) . . . . ? C32 C33 C34 C35 -1.3(13) . . . . ? C33 C34 C35 C30 2.3(12) . . . . ? C31 C30 C35 C34 -1.0(11) . . . . ? P22 C30 C35 C34 179.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.448 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.077