# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name _publ_author_address P.O'Brien ; Department of Chemistry University of Manchester Manchester M13 9PL England UK ; 'Adekunle Adeogun' '' 'Mohammad Afzaal' '' 'Chinh Q. Nguyen' '' _publ_contact_author_name "P. O'Brien" _publ_contact_author_address ; School of Chemistry The University of Manchester Oxford Road Manchester M13 9PL UNITED KINGDOM ; _publ_contact_author_email PAUL.OBRIEN@MANCHESTER.AC.UK _publ_section_title ; A facile and reproducible synthesis of bis(dialkylselenophosphenyl)-selenides and -diselinides: X-ray structures of [iPr2PSe2]Se, [iPr2PSe2]Se2 and [(Ph)2PSe2]Se ; _publ_contact_author_fax 44(161)275-4734 _publ_contact_author_phone 44(161)275-4700 _publ_contact_letter # Include date of submission ; Date of submission ? Please consider this CIF submission for publication as a Regular Structural Paper in Acta Crystallographica C. ; _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_author ; Madeleine Helliwell ; # Attachment 's2215abs_cif.txt' data_s2215abs _database_code_depnum_ccdc_archive 'CCDC 282911' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _publ_section_exptl_refinement ; The structure was solved by direct methods. All non-H atoms were refined anisotropically. H atoms were included in calculated positions. ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H28 P2 Se3' _chemical_formula_weight 471.16 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.324(3) _cell_length_b 10.189(5) _cell_length_c 12.669(6) _cell_angle_alpha 101.544(8) _cell_angle_beta 95.067(9) _cell_angle_gamma 101.157(8) _cell_volume 900.7(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2298 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 26.28 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 6.285 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2170 _exptl_absorpt_correction_T_max 0.5722 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5048 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3549 _reflns_number_gt 2952 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0703P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3549 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1092 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 0.12798(6) 0.52321(5) 0.65877(4) 0.01427(14) Uani 1 1 d . . . Se2 Se 0.35544(6) 0.86984(5) 0.70744(4) 0.01813(15) Uani 1 1 d . . . Se3 Se -0.20509(7) 0.44804(5) 0.86038(4) 0.01905(15) Uani 1 1 d . . . P1 P 0.16241(16) 0.73351(12) 0.77037(11) 0.0141(3) Uani 1 1 d . . . P2 P -0.08783(16) 0.37198(13) 0.72157(10) 0.0139(3) Uani 1 1 d . . . C1 C 0.2486(6) 0.7164(5) 0.9061(4) 0.0161(10) Uani 1 1 d . . . H1 H 0.1568 0.6421 0.9262 0.019 Uiso 1 1 calc R . . C2 C 0.2699(8) 0.8469(6) 0.9929(5) 0.0288(13) Uani 1 1 d . . . H2A H 0.3419 0.8389 1.0594 0.043 Uiso 1 1 calc R . . H2B H 0.1454 0.8610 1.0083 0.043 Uiso 1 1 calc R . . H2C H 0.3360 0.9252 0.9670 0.043 Uiso 1 1 calc R . . C3 C 0.4385(7) 0.6736(6) 0.9041(5) 0.0247(12) Uani 1 1 d . . . H3A H 0.5366 0.7524 0.9004 0.037 Uiso 1 1 calc R . . H3B H 0.4314 0.5994 0.8403 0.037 Uiso 1 1 calc R . . H3C H 0.4687 0.6417 0.9702 0.037 Uiso 1 1 calc R . . C4 C -0.0760(6) 0.7679(5) 0.7592(4) 0.0165(10) Uani 1 1 d . . . H4 H -0.1647 0.6863 0.7717 0.020 Uiso 1 1 calc R . . C5 C -0.0948(7) 0.8937(5) 0.8431(5) 0.0236(12) Uani 1 1 d . . . H5A H 0.0087 0.9709 0.8434 0.035 Uiso 1 1 calc R . . H5B H -0.0905 0.8727 0.9154 0.035 Uiso 1 1 calc R . . H5C H -0.2146 0.9182 0.8244 0.035 Uiso 1 1 calc R . . C6 C -0.1334(7) 0.7843(5) 0.6449(4) 0.0209(11) Uani 1 1 d . . . H6A H -0.2651 0.7916 0.6370 0.031 Uiso 1 1 calc R . . H6B H -0.1177 0.7044 0.5917 0.031 Uiso 1 1 calc R . . H6C H -0.0542 0.8675 0.6324 0.031 Uiso 1 1 calc R . . C7 C -0.2631(6) 0.2994(5) 0.6002(4) 0.0148(10) Uani 1 1 d . . . H7 H -0.1947 0.2792 0.5360 0.018 Uiso 1 1 calc R . . C8 C -0.3828(7) 0.4007(5) 0.5802(5) 0.0223(11) Uani 1 1 d . . . H8A H -0.4677 0.3624 0.5121 0.034 Uiso 1 1 calc R . . H8B H -0.3012 0.4871 0.5752 0.034 Uiso 1 1 calc R . . H8C H -0.4565 0.4180 0.6404 0.034 Uiso 1 1 calc R . . C9 C -0.3860(7) 0.1641(5) 0.6119(5) 0.0214(11) Uani 1 1 d . . . H9A H -0.4500 0.1811 0.6764 0.032 Uiso 1 1 calc R . . H9B H -0.3069 0.0983 0.6195 0.032 Uiso 1 1 calc R . . H9C H -0.4794 0.1266 0.5472 0.032 Uiso 1 1 calc R . . C10 C 0.0379(7) 0.2366(5) 0.7388(4) 0.0204(11) Uani 1 1 d . . . H10 H -0.0556 0.1614 0.7565 0.024 Uiso 1 1 calc R . . C11 C 0.1942(8) 0.2853(6) 0.8359(5) 0.0285(13) Uani 1 1 d . . . H11A H 0.2487 0.2078 0.8473 0.043 Uiso 1 1 calc R . . H11B H 0.1416 0.3218 0.9012 0.043 Uiso 1 1 calc R . . H11C H 0.2919 0.3573 0.8212 0.043 Uiso 1 1 calc R . . C12 C 0.1083(7) 0.1741(5) 0.6350(5) 0.0237(12) Uani 1 1 d . . . H12A H 0.1979 0.2451 0.6130 0.036 Uiso 1 1 calc R . . H12B H 0.0019 0.1363 0.5773 0.036 Uiso 1 1 calc R . . H12C H 0.1703 0.1007 0.6479 0.036 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 0.0126(2) 0.0141(3) 0.0169(3) 0.00476(19) 0.00668(19) 0.00131(18) Se2 0.0132(3) 0.0175(3) 0.0251(3) 0.0095(2) 0.0070(2) -0.00002(19) Se3 0.0181(3) 0.0211(3) 0.0182(3) 0.0056(2) 0.0086(2) 0.0010(2) P1 0.0109(6) 0.0139(6) 0.0179(7) 0.0045(5) 0.0046(5) 0.0015(5) P2 0.0119(6) 0.0146(6) 0.0160(7) 0.0056(5) 0.0044(5) 0.0014(5) C1 0.010(2) 0.016(2) 0.021(3) 0.006(2) 0.0033(19) -0.0010(18) C2 0.035(3) 0.029(3) 0.022(3) 0.003(2) 0.001(2) 0.009(3) C3 0.015(2) 0.027(3) 0.032(3) 0.008(2) -0.001(2) 0.004(2) C4 0.010(2) 0.019(2) 0.024(3) 0.010(2) 0.0041(19) 0.0042(19) C5 0.018(3) 0.024(3) 0.030(3) 0.002(2) 0.007(2) 0.009(2) C6 0.018(3) 0.018(3) 0.029(3) 0.009(2) 0.003(2) 0.005(2) C7 0.009(2) 0.016(2) 0.019(3) 0.005(2) 0.0012(19) -0.0005(18) C8 0.016(2) 0.024(3) 0.028(3) 0.009(2) 0.000(2) 0.004(2) C9 0.016(2) 0.016(3) 0.028(3) 0.004(2) 0.000(2) -0.004(2) C10 0.017(2) 0.015(2) 0.031(3) 0.011(2) 0.005(2) 0.002(2) C11 0.022(3) 0.030(3) 0.037(4) 0.015(3) -0.003(2) 0.007(2) C12 0.022(3) 0.020(3) 0.033(3) 0.011(2) 0.009(2) 0.006(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 2.2736(16) . ? Se1 P2 2.2969(14) . ? Se2 P1 2.1085(14) . ? Se3 P2 2.0999(15) . ? P1 C1 1.832(5) . ? P1 C4 1.845(5) . ? P2 C10 1.837(5) . ? P2 C7 1.840(5) . ? C1 C2 1.519(7) . ? C1 C3 1.536(7) . ? C1 H1 1.0000 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C6 1.522(7) . ? C4 C5 1.530(7) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.521(7) . ? C7 C9 1.535(6) . ? C7 H7 1.0000 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C12 1.520(7) . ? C10 C11 1.535(8) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 P1 Se1 P2 107.50(6) . . ? C1 P1 C4 113.8(2) . . ? C1 P1 Se2 113.14(15) . . ? C4 P1 Se2 112.77(16) . . ? C1 P1 Se1 106.14(16) . . ? C4 P1 Se1 103.78(17) . . ? Se2 P1 Se1 106.25(6) . . ? C10 P2 C7 106.3(2) . . ? C10 P2 Se3 113.19(18) . . ? C7 P2 Se3 113.22(16) . . ? C10 P2 Se1 102.98(16) . . ? C7 P2 Se1 101.67(16) . . ? Se3 P2 Se1 118.05(6) . . ? C2 C1 C3 109.2(4) . . ? C2 C1 P1 113.2(4) . . ? C3 C1 P1 109.7(3) . . ? C2 C1 H1 108.2 . . ? C3 C1 H1 108.2 . . ? P1 C1 H1 108.2 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C6 C4 C5 110.1(4) . . ? C6 C4 P1 110.0(3) . . ? C5 C4 P1 113.0(4) . . ? C6 C4 H4 107.8 . . ? C5 C4 H4 107.8 . . ? P1 C4 H4 107.8 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 C9 110.9(4) . . ? C8 C7 P2 111.2(3) . . ? C9 C7 P2 110.0(3) . . ? C8 C7 H7 108.2 . . ? C9 C7 H7 108.2 . . ? P2 C7 H7 108.2 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C12 C10 C11 112.4(4) . . ? C12 C10 P2 112.7(4) . . ? C11 C10 P2 111.9(4) . . ? C12 C10 H10 106.4 . . ? C11 C10 H10 106.4 . . ? P2 C10 H10 106.4 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 P2 Se1 P1 C1 60.83(16) . . . . ? P2 Se1 P1 C4 -59.36(17) . . . . ? P2 Se1 P1 Se2 -178.47(5) . . . . ? P1 Se1 P2 C10 -125.80(19) . . . . ? P1 Se1 P2 C7 124.20(16) . . . . ? P1 Se1 P2 Se3 -0.30(8) . . . . ? C4 P1 C1 C2 -63.5(4) . . . . ? Se2 P1 C1 C2 66.9(4) . . . . ? Se1 P1 C1 C2 -176.9(3) . . . . ? C4 P1 C1 C3 174.3(3) . . . . ? Se2 P1 C1 C3 -55.3(4) . . . . ? Se1 P1 C1 C3 60.8(3) . . . . ? C1 P1 C4 C6 178.5(3) . . . . ? Se2 P1 C4 C6 47.9(4) . . . . ? Se1 P1 C4 C6 -66.6(3) . . . . ? C1 P1 C4 C5 54.9(4) . . . . ? Se2 P1 C4 C5 -75.6(4) . . . . ? Se1 P1 C4 C5 169.8(3) . . . . ? C10 P2 C7 C8 177.6(3) . . . . ? Se3 P2 C7 C8 52.7(4) . . . . ? Se1 P2 C7 C8 -75.0(3) . . . . ? C10 P2 C7 C9 54.2(4) . . . . ? Se3 P2 C7 C9 -70.7(3) . . . . ? Se1 P2 C7 C9 161.6(3) . . . . ? C7 P2 C10 C12 50.3(4) . . . . ? Se3 P2 C10 C12 175.2(3) . . . . ? Se1 P2 C10 C12 -56.2(4) . . . . ? C7 P2 C10 C11 178.1(4) . . . . ? Se3 P2 C10 C11 -56.9(4) . . . . ? Se1 P2 C10 C11 71.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.263 _refine_diff_density_min -1.228 _refine_diff_density_rms 0.162 # Attachment 's2226na_cif.txt' data_s2226na _database_code_depnum_ccdc_archive 'CCDC 291034' _publ_section_title_footnote ; ? ; #------------------ TEXT ----------------------------------------------------# _publ_section_synopsis ; # Insert blank lines between paragraphs ? ; _publ_section_abstract ; # Insert blank lines between paragraphs ? ; _publ_section_comment ; # Insert blank lines between paragraphs ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; The structure was solved by direct methods. The non-hydrogen atoms were refined anisotropically, except where the ADP becomes NPD or unrealistic. H atoms were included in calculated positions, except where they were largely indeterminate. ; # Insert blank lines between references _publ_section_references ; # # Put all your general crystallographic references here # Delete as required from the document CIF # Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure refinement. University of G\"ottingen, Germany. Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure refinement. University of G\"ottingen, Germany. Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3, edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189. Oxford University Press. Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution. University of G\"ottingen, Germany. Wilson, A.J.C. (1992) Ed. International Tables for Crystallography, Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands. ; _publ_section_figure_captions ; Figure 1. View of (I) (50% probability displacement ellipsoids) ; _publ_section_acknowledgements ; ? ; _publ_section_table_legends ; Table 1. Fractional atomic coordinates and equivalent isotropic displacement parameters (\%A^2^) Table 2. Selected geometric parameters (\%A ,\% ) ; #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H28 P2 Se4' _chemical_formula_weight 550.12 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 C2/c 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' '-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 20.905(8) _cell_length_b 8.393(3) _cell_length_c 11.592(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.120(9) _cell_angle_gamma 90.00 _cell_volume 1980.8(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used input _cell_measurement_theta_min 2.6295 _cell_measurement_theta_max 28.2495 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.845 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 7.556 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3134 _exptl_absorpt_correction_T_max 0.5832 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8158 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 28.26 _reflns_number_total 2319 _reflns_number_gt 2047 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0316P)^2^+2.9155P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2319 _refine_ls_number_parameters 86 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0691 _refine_ls_wR_factor_gt 0.0669 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _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 C1 C 0.32648(15) 0.1898(4) 0.1616(3) 0.0168(6) Uani 1 1 d . . . H1 H 0.2827 0.2340 0.1210 0.020 Uiso 1 1 calc R . . C2 C 0.32357(17) 0.0107(4) 0.1369(3) 0.0234(7) Uani 1 1 d . . . H2A H 0.3640 -0.0397 0.1812 0.035 Uiso 1 1 calc R . . H2B H 0.3191 -0.0077 0.0520 0.035 Uiso 1 1 calc R . . H2C H 0.2858 -0.0354 0.1618 0.035 Uiso 1 1 calc R . . C3 C 0.33464(17) 0.2241(4) 0.2939(3) 0.0224(7) Uani 1 1 d . . . H3A H 0.2970 0.1806 0.3207 0.034 Uiso 1 1 calc R . . H3B H 0.3370 0.3395 0.3071 0.034 Uiso 1 1 calc R . . H3C H 0.3751 0.1742 0.3384 0.034 Uiso 1 1 calc R . . C4 C 0.39527(14) 0.4928(4) 0.1466(3) 0.0157(6) Uani 1 1 d . . . H4 H 0.4087 0.4912 0.2351 0.019 Uiso 1 1 calc R . . C5 C 0.44663(16) 0.5857(4) 0.0997(3) 0.0222(7) Uani 1 1 d . . . H5A H 0.4330 0.5932 0.0132 0.033 Uiso 1 1 calc R . . H5B H 0.4890 0.5306 0.1218 0.033 Uiso 1 1 calc R . . H5C H 0.4509 0.6930 0.1339 0.033 Uiso 1 1 calc R . . C6 C 0.32780(16) 0.5727(4) 0.1102(3) 0.0217(7) Uani 1 1 d . . . H6A H 0.3307 0.6823 0.1401 0.033 Uiso 1 1 calc R . . H6B H 0.2959 0.5131 0.1435 0.033 Uiso 1 1 calc R . . H6C H 0.3136 0.5739 0.0236 0.033 Uiso 1 1 calc R . . P1 P 0.38758(4) 0.28701(10) 0.09356(7) 0.01360(17) Uani 1 1 d . . . Se1 Se 0.483534(15) 0.15665(4) 0.14459(3) 0.01835(10) Uani 1 1 d . . . Se2 Se 0.366286(16) 0.26208(4) -0.09290(3) 0.02045(10) 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 C1 0.0132(14) 0.0232(16) 0.0146(14) 0.0029(12) 0.0046(12) -0.0036(13) C2 0.0267(17) 0.0207(17) 0.0215(16) 0.0012(13) 0.0027(14) -0.0082(14) C3 0.0207(16) 0.0301(19) 0.0186(16) 0.0022(13) 0.0093(13) -0.0039(14) C4 0.0150(15) 0.0161(15) 0.0154(14) -0.0013(11) 0.0027(12) 0.0008(12) C5 0.0244(17) 0.0222(17) 0.0202(16) 0.0015(13) 0.0052(13) -0.0063(14) C6 0.0226(16) 0.0195(17) 0.0230(17) -0.0018(13) 0.0050(13) 0.0015(13) P1 0.0131(4) 0.0166(4) 0.0113(4) -0.0003(3) 0.0033(3) -0.0002(3) Se1 0.01398(15) 0.02251(18) 0.01844(17) -0.00479(12) 0.00343(12) 0.00239(12) Se2 0.02232(18) 0.02779(19) 0.01147(16) -0.00230(12) 0.00428(12) -0.00214(13) _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 C1 C2 1.529(5) . ? C1 C3 1.531(4) . ? C1 P1 1.837(3) . ? C1 H1 1.0000 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.524(4) . ? C4 C6 1.532(4) . ? C4 P1 1.828(3) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? P1 Se2 2.1158(11) . ? P1 Se1 2.2433(11) . ? Se1 Se1 2.3839(10) 2_655 ? 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 C1 C3 111.3(3) . . ? C2 C1 P1 111.0(2) . . ? C3 C1 P1 114.6(2) . . ? C2 C1 H1 106.5 . . ? C3 C1 H1 106.5 . . ? P1 C1 H1 106.5 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C6 110.9(3) . . ? C5 C4 P1 112.2(2) . . ? C6 C4 P1 108.4(2) . . ? C5 C4 H4 108.4 . . ? C6 C4 H4 108.4 . . ? P1 C4 H4 108.4 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 P1 C1 106.95(14) . . ? C4 P1 Se2 114.79(10) . . ? C1 P1 Se2 112.90(10) . . ? C4 P1 Se1 111.52(10) . . ? C1 P1 Se1 109.72(11) . . ? Se2 P1 Se1 100.91(3) . . ? P1 Se1 Se1 107.65(3) . 2_655 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C4 P1 C1 178.0(2) . . . . ? C6 C4 P1 C1 -59.2(2) . . . . ? C5 C4 P1 Se2 -55.9(2) . . . . ? C6 C4 P1 Se2 66.9(2) . . . . ? C5 C4 P1 Se1 58.1(2) . . . . ? C6 C4 P1 Se1 -179.12(17) . . . . ? C2 C1 P1 C4 -171.9(2) . . . . ? C3 C1 P1 C4 -44.8(3) . . . . ? C2 C1 P1 Se2 60.9(2) . . . . ? C3 C1 P1 Se2 -172.0(2) . . . . ? C2 C1 P1 Se1 -50.8(2) . . . . ? C3 C1 P1 Se1 76.3(2) . . . . ? C4 P1 Se1 Se1 60.30(11) . . . 2_655 ? C1 P1 Se1 Se1 -58.01(11) . . . 2_655 ? Se2 P1 Se1 Se1 -177.35(2) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.697 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.117 # Attachment 's2236abs_cif.txt' data_s2236abs _database_code_depnum_ccdc_archive 'CCDC 291035' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _publ_section_exptl_refinement ; The structure was solved by the direct methods. The non H atoms were refined anisotropically. H atoms were included in calculated positions. ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H20 P2 Se3' _chemical_formula_weight 607.22 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.279(3) _cell_length_b 11.260(3) _cell_length_c 13.075(4) _cell_angle_alpha 106.562(5) _cell_angle_beta 100.360(5) _cell_angle_gamma 110.862(4) _cell_volume 1161.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1298 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 25.61 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.736 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 4.896 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4409 _exptl_absorpt_correction_T_max 0.6954 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5822 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0809 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4004 _reflns_number_gt 3103 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0719P)^2^+3.5960P] 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 4004 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1472 _refine_ls_wR_factor_gt 0.1369 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 1.09562(10) 0.30251(9) 0.55119(7) 0.0202(2) Uani 1 1 d . . . Se2 Se 0.84020(9) -0.01136(8) 0.34812(7) 0.0159(2) Uani 1 1 d . . . Se3 Se 0.67645(10) -0.06791(9) 0.04643(7) 0.0196(2) Uani 1 1 d . . . P1 P 0.9115(2) 0.2161(2) 0.39582(18) 0.0157(4) Uani 1 1 d . . . P2 P 0.6350(2) -0.1303(2) 0.17982(17) 0.0157(5) Uani 1 1 d . . . C1 C 0.7314(9) 0.2438(8) 0.3957(7) 0.0172(17) Uani 1 1 d . . . C2 C 0.6097(10) 0.2010(8) 0.2959(7) 0.0197(18) Uani 1 1 d . . . H2 H 0.6227 0.1603 0.2258 0.024 Uiso 1 1 calc R . . C3 C 0.4679(10) 0.2181(8) 0.2991(7) 0.0196(18) Uani 1 1 d . . . H3 H 0.3820 0.1847 0.2314 0.024 Uiso 1 1 calc R . . C4 C 0.4533(10) 0.2838(9) 0.4012(8) 0.024(2) Uani 1 1 d . . . H4 H 0.3577 0.2965 0.4030 0.029 Uiso 1 1 calc R . . C5 C 0.5731(10) 0.3299(9) 0.4980(7) 0.023(2) Uani 1 1 d . . . H5 H 0.5618 0.3765 0.5670 0.028 Uiso 1 1 calc R . . C6 C 0.7142(10) 0.3104(9) 0.4987(7) 0.023(2) Uani 1 1 d . . . H6 H 0.7969 0.3415 0.5676 0.028 Uiso 1 1 calc R . . C7 C 0.9797(9) 0.2705(8) 0.2892(7) 0.0173(17) Uani 1 1 d . . . C8 C 0.9700(9) 0.3893(9) 0.2807(7) 0.0191(18) Uani 1 1 d . . . H8 H 0.9157 0.4306 0.3234 0.023 Uiso 1 1 calc R . . C9 C 1.0394(10) 0.4471(9) 0.2102(7) 0.0220(19) Uani 1 1 d . . . H9 H 1.0334 0.5276 0.2049 0.026 Uiso 1 1 calc R . . C10 C 1.1184(10) 0.3842(9) 0.1474(7) 0.025(2) Uani 1 1 d . . . H10 H 1.1669 0.4228 0.0995 0.030 Uiso 1 1 calc R . . C11 C 1.1262(10) 0.2672(10) 0.1547(7) 0.024(2) Uani 1 1 d . . . H11 H 1.1788 0.2250 0.1110 0.029 Uiso 1 1 calc R . . C12 C 1.0582(9) 0.2102(9) 0.2253(7) 0.0192(18) Uani 1 1 d . . . H12 H 1.0651 0.1297 0.2300 0.023 Uiso 1 1 calc R . . C13 C 0.4491(9) -0.1318(8) 0.2085(7) 0.0166(17) Uani 1 1 d . . . C14 C 0.3226(10) -0.1535(9) 0.1201(7) 0.025(2) Uani 1 1 d . . . H14 H 0.3341 -0.1668 0.0474 0.030 Uiso 1 1 calc R . . C15 C 0.1773(10) -0.1557(9) 0.1386(8) 0.025(2) Uani 1 1 d . . . H15 H 0.0902 -0.1701 0.0784 0.031 Uiso 1 1 calc R . . C16 C 0.1611(10) -0.1369(9) 0.2439(8) 0.027(2) Uani 1 1 d . . . H16 H 0.0619 -0.1401 0.2557 0.033 Uiso 1 1 calc R . . C17 C 0.2874(10) -0.1134(9) 0.3327(8) 0.026(2) Uani 1 1 d . . . H17 H 0.2759 -0.0986 0.4055 0.031 Uiso 1 1 calc R . . C18 C 0.4312(10) -0.1114(9) 0.3153(7) 0.0208(18) Uani 1 1 d . . . H18 H 0.5179 -0.0962 0.3761 0.025 Uiso 1 1 calc R . . C19 C 0.6292(9) -0.2979(8) 0.1646(7) 0.0173(17) Uani 1 1 d . . . C20 C 0.7104(10) -0.3491(9) 0.0975(7) 0.0196(18) Uani 1 1 d . . . H20 H 0.7657 -0.2983 0.0585 0.024 Uiso 1 1 calc R . . C21 C 0.7100(10) -0.4762(9) 0.0880(8) 0.026(2) Uani 1 1 d . . . H21 H 0.7620 -0.5132 0.0401 0.031 Uiso 1 1 calc R . . C22 C 0.6345(10) -0.5485(8) 0.1478(7) 0.0187(18) Uani 1 1 d . . . H22 H 0.6370 -0.6337 0.1418 0.022 Uiso 1 1 calc R . . C23 C 0.5554(10) -0.4974(8) 0.2160(7) 0.0181(18) Uani 1 1 d . . . H23 H 0.5046 -0.5466 0.2576 0.022 Uiso 1 1 calc R . . C24 C 0.5511(9) -0.3714(8) 0.2233(7) 0.0192(18) Uani 1 1 d . . . H24 H 0.4946 -0.3366 0.2685 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 0.0214(4) 0.0227(5) 0.0162(5) 0.0072(4) 0.0025(3) 0.0111(4) Se2 0.0185(4) 0.0175(4) 0.0156(4) 0.0091(3) 0.0047(3) 0.0102(3) Se3 0.0267(5) 0.0216(5) 0.0175(5) 0.0124(4) 0.0099(4) 0.0127(4) P1 0.0169(10) 0.0157(11) 0.0161(11) 0.0069(9) 0.0054(9) 0.0079(9) P2 0.0173(10) 0.0176(11) 0.0167(11) 0.0099(9) 0.0063(9) 0.0092(9) C1 0.021(4) 0.018(4) 0.017(4) 0.012(4) 0.007(3) 0.009(4) C2 0.025(4) 0.013(4) 0.024(5) 0.010(4) 0.013(4) 0.005(4) C3 0.021(4) 0.023(5) 0.027(5) 0.018(4) 0.008(4) 0.015(4) C4 0.028(5) 0.030(5) 0.032(5) 0.021(4) 0.017(4) 0.019(4) C5 0.031(5) 0.029(5) 0.025(5) 0.016(4) 0.023(4) 0.019(4) C6 0.032(5) 0.035(5) 0.019(5) 0.018(4) 0.011(4) 0.024(4) C7 0.016(4) 0.019(4) 0.011(4) 0.005(3) 0.003(3) 0.002(3) C8 0.014(4) 0.023(5) 0.016(4) 0.008(4) 0.000(3) 0.006(4) C9 0.026(4) 0.031(5) 0.022(5) 0.018(4) 0.013(4) 0.017(4) C10 0.022(4) 0.033(5) 0.024(5) 0.019(4) 0.007(4) 0.011(4) C11 0.018(4) 0.038(6) 0.018(5) 0.010(4) 0.009(4) 0.014(4) C12 0.020(4) 0.018(4) 0.017(5) 0.006(4) 0.004(4) 0.007(4) C13 0.022(4) 0.011(4) 0.017(4) 0.006(3) 0.004(3) 0.006(3) C14 0.029(5) 0.018(5) 0.018(5) 0.003(4) 0.003(4) 0.005(4) C15 0.019(4) 0.026(5) 0.030(5) 0.008(4) 0.007(4) 0.011(4) C16 0.022(4) 0.020(5) 0.042(6) 0.012(4) 0.015(4) 0.010(4) C17 0.032(5) 0.024(5) 0.026(5) 0.012(4) 0.013(4) 0.013(4) C18 0.022(4) 0.020(5) 0.028(5) 0.016(4) 0.009(4) 0.011(4) C19 0.018(4) 0.014(4) 0.019(5) 0.009(4) 0.002(3) 0.006(3) C20 0.025(4) 0.026(5) 0.015(4) 0.013(4) 0.009(4) 0.014(4) C21 0.027(5) 0.030(5) 0.028(5) 0.011(4) 0.014(4) 0.020(4) C22 0.027(4) 0.017(4) 0.022(5) 0.015(4) 0.007(4) 0.014(4) C23 0.025(4) 0.012(4) 0.021(5) 0.013(4) 0.008(4) 0.006(4) C24 0.021(4) 0.021(5) 0.018(5) 0.008(4) 0.004(4) 0.012(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 Se1 P1 2.106(2) . ? Se2 P1 2.263(2) . ? Se2 P2 2.293(2) . ? Se3 P2 2.105(2) . ? P1 C7 1.802(8) . ? P1 C1 1.806(8) . ? P2 C19 1.821(8) . ? P2 C13 1.825(8) . ? C1 C2 1.391(11) . ? C1 C6 1.410(11) . ? C2 C3 1.403(11) . ? C2 H2 0.9500 . ? C3 C4 1.387(12) . ? C3 H3 0.9500 . ? C4 C5 1.347(12) . ? C4 H4 0.9500 . ? C5 C6 1.401(11) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.392(11) . ? C7 C8 1.406(11) . ? C8 C9 1.394(11) . ? C8 H8 0.9500 . ? C9 C10 1.403(12) . ? C9 H9 0.9500 . ? C10 C11 1.373(12) . ? C10 H10 0.9500 . ? C11 C12 1.385(11) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.385(11) . ? C13 C18 1.399(11) . ? C14 C15 1.405(12) . ? C14 H14 0.9500 . ? C15 C16 1.377(12) . ? C15 H15 0.9500 . ? C16 C17 1.381(12) . ? C16 H16 0.9500 . ? C17 C18 1.387(11) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.388(11) . ? C19 C24 1.391(11) . ? C20 C21 1.399(12) . ? C20 H20 0.9500 . ? C21 C22 1.385(11) . ? C21 H21 0.9500 . ? C22 C23 1.381(11) . ? C22 H22 0.9500 . ? C23 C24 1.410(11) . ? 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 P1 Se2 P2 109.01(8) . . ? C7 P1 C1 105.4(4) . . ? C7 P1 Se1 113.6(3) . . ? C1 P1 Se1 117.1(3) . . ? C7 P1 Se2 110.1(3) . . ? C1 P1 Se2 108.2(3) . . ? Se1 P1 Se2 102.28(9) . . ? C19 P2 C13 106.9(3) . . ? C19 P2 Se3 115.2(3) . . ? C13 P2 Se3 113.7(3) . . ? C19 P2 Se2 95.7(3) . . ? C13 P2 Se2 107.0(3) . . ? Se3 P2 Se2 116.51(10) . . ? C2 C1 C6 119.5(7) . . ? C2 C1 P1 121.2(6) . . ? C6 C1 P1 119.4(6) . . ? C1 C2 C3 119.7(8) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C4 C3 C2 119.8(8) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 120.7(8) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 121.2(8) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 119.0(8) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? C12 C7 C8 119.1(7) . . ? C12 C7 P1 122.8(6) . . ? C8 C7 P1 117.7(6) . . ? C9 C8 C7 120.6(8) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 118.8(8) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 120.5(7) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.7(8) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C7 120.2(8) . . ? C11 C12 H12 119.9 . . ? C7 C12 H12 119.9 . . ? C14 C13 C18 119.7(7) . . ? C14 C13 P2 117.8(6) . . ? C18 C13 P2 122.5(6) . . ? C13 C14 C15 119.6(8) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 120.0(8) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 120.8(8) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C17 C18 119.7(8) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C13 120.3(8) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? C20 C19 C24 120.1(7) . . ? C20 C19 P2 119.1(6) . . ? C24 C19 P2 120.7(6) . . ? C19 C20 C21 119.3(7) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C22 C21 C20 120.6(8) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C23 C22 C21 120.4(7) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C24 119.3(7) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? C19 C24 C23 120.2(8) . . ? C19 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? 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 P2 Se2 P1 C7 -59.8(3) . . . . ? P2 Se2 P1 C1 54.9(3) . . . . ? P2 Se2 P1 Se1 179.20(8) . . . . ? P1 Se2 P2 C19 174.3(3) . . . . ? P1 Se2 P2 C13 -76.1(3) . . . . ? P1 Se2 P2 Se3 52.47(12) . . . . ? C7 P1 C1 C2 46.9(7) . . . . ? Se1 P1 C1 C2 174.3(5) . . . . ? Se2 P1 C1 C2 -70.8(7) . . . . ? C7 P1 C1 C6 -132.9(6) . . . . ? Se1 P1 C1 C6 -5.5(7) . . . . ? Se2 P1 C1 C6 109.4(6) . . . . ? C6 C1 C2 C3 -3.3(11) . . . . ? P1 C1 C2 C3 176.9(6) . . . . ? C1 C2 C3 C4 3.3(11) . . . . ? C2 C3 C4 C5 -0.9(12) . . . . ? C3 C4 C5 C6 -1.4(13) . . . . ? C4 C5 C6 C1 1.4(12) . . . . ? C2 C1 C6 C5 1.0(12) . . . . ? P1 C1 C6 C5 -179.2(6) . . . . ? C1 P1 C7 C12 -148.0(7) . . . . ? Se1 P1 C7 C12 82.5(7) . . . . ? Se2 P1 C7 C12 -31.5(7) . . . . ? C1 P1 C7 C8 39.9(7) . . . . ? Se1 P1 C7 C8 -89.7(6) . . . . ? Se2 P1 C7 C8 156.3(5) . . . . ? C12 C7 C8 C9 -0.7(12) . . . . ? P1 C7 C8 C9 171.8(6) . . . . ? C7 C8 C9 C10 0.3(12) . . . . ? C8 C9 C10 C11 0.4(12) . . . . ? C9 C10 C11 C12 -0.9(13) . . . . ? C10 C11 C12 C7 0.5(13) . . . . ? C8 C7 C12 C11 0.3(12) . . . . ? P1 C7 C12 C11 -171.8(6) . . . . ? C19 P2 C13 C14 -100.4(7) . . . . ? Se3 P2 C13 C14 27.8(7) . . . . ? Se2 P2 C13 C14 158.0(6) . . . . ? C19 P2 C13 C18 79.9(7) . . . . ? Se3 P2 C13 C18 -151.9(6) . . . . ? Se2 P2 C13 C18 -21.8(7) . . . . ? C18 C13 C14 C15 -0.4(12) . . . . ? P2 C13 C14 C15 179.9(6) . . . . ? C13 C14 C15 C16 -0.2(13) . . . . ? C14 C15 C16 C17 1.1(13) . . . . ? C15 C16 C17 C18 -1.3(13) . . . . ? C16 C17 C18 C13 0.6(13) . . . . ? C14 C13 C18 C17 0.2(12) . . . . ? P2 C13 C18 C17 179.9(6) . . . . ? C13 P2 C19 C20 152.3(6) . . . . ? Se3 P2 C19 C20 24.9(7) . . . . ? Se2 P2 C19 C20 -98.0(6) . . . . ? C13 P2 C19 C24 -30.7(7) . . . . ? Se3 P2 C19 C24 -158.1(6) . . . . ? Se2 P2 C19 C24 79.0(6) . . . . ? C24 C19 C20 C21 1.3(12) . . . . ? P2 C19 C20 C21 178.3(6) . . . . ? C19 C20 C21 C22 -2.3(13) . . . . ? C20 C21 C22 C23 1.3(13) . . . . ? C21 C22 C23 C24 0.6(12) . . . . ? C20 C19 C24 C23 0.7(12) . . . . ? P2 C19 C24 C23 -176.3(6) . . . . ? C22 C23 C24 C19 -1.6(12) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.152 _refine_diff_density_min -0.999 _refine_diff_density_rms 0.178