# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2010 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Woollins, John' _publ_contact_author_name 'Woollins, John' _publ_contact_author_email jdw3@st-and.ac.uk _publ_section_title ; Synthesis and X-ray Structures of New Phosphorus-Selenium Heterocycles with an E-P(Se)-Ea(E, Ea = N, S, Se) Linkage ; # Attachment '- 2a.cif' data_p-1 _database_code_depnum_ccdc_archive 'CCDC 752125' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H15 N2 P Se' _chemical_formula_sum 'C18 H15 N2 P Se' _chemical_formula_weight 369.25 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' N N 0.0061 0.0033 '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 9.108(2) _cell_length_b 9.656(2) _cell_length_c 10.017(2) _cell_angle_alpha 103.676(6) _cell_angle_beta 107.108(3) _cell_angle_gamma 95.654(4) _cell_volume 804.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 2701 _cell_measurement_theta_min 2.2070 _cell_measurement_theta_max 28.1544 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 2.430 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7120 _exptl_absorpt_correction_T_max 0.7932 _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 5691 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.1064 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 28.69 _reflns_number_total 3086 _reflns_number_gt 2401 _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 PLUTON _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^)+(0.0237P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3086 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0744 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.24333(5) 0.44488(4) 0.77156(4) 0.02639(15) Uani 1 1 d . . . P1 P 0.24838(11) 0.29276(10) 0.89021(10) 0.0200(2) Uani 1 1 d . . . N2 N 0.1029(3) 0.2724(3) 0.9606(3) 0.0182(7) Uani 1 1 d . . . N5 N 0.3851(3) 0.3286(3) 1.0521(3) 0.0212(7) Uani 1 1 d . . . C6 C -0.0597(4) 0.2290(4) 0.8765(4) 0.0190(8) Uani 1 1 d . . . C3 C 0.1597(4) 0.2937(3) 1.1113(4) 0.0181(8) Uani 1 1 d . . . C17 C 0.1972(4) 0.0707(4) 0.6359(4) 0.0238(9) Uani 1 1 d . . . H17 H 0.1623 0.1386 0.5843 0.029 Uiso 1 1 calc R . . C11 C -0.1433(5) 0.3301(4) 0.8288(4) 0.0308(10) Uani 1 1 d . . . H11 H -0.0935 0.4277 0.8504 0.037 Uiso 1 1 calc R . . C12 C 0.0737(4) 0.2890(3) 1.2037(4) 0.0210(8) Uani 1 1 d . . . H12 H -0.0372 0.2675 1.1671 0.025 Uiso 1 1 calc R . . C4 C 0.3227(4) 0.3291(4) 1.1664(4) 0.0197(8) Uani 1 1 d . . . C18 C 0.1931(4) -0.0711(4) 0.5593(4) 0.0288(9) Uani 1 1 d . . . H18 H 0.1553 -0.0999 0.4560 0.035 Uiso 1 1 calc R . . C15 C 0.4031(5) 0.3558(4) 1.3121(4) 0.0278(9) Uani 1 1 d . . . H15 H 0.5140 0.3782 1.3487 0.033 Uiso 1 1 calc R . . C13 C 0.1538(5) 0.3164(4) 1.3518(4) 0.0266(9) Uani 1 1 d . . . H13 H 0.0969 0.3127 1.4170 0.032 Uiso 1 1 calc R . . C16 C 0.2518(4) 0.1137(4) 0.7870(4) 0.0199(8) Uani 1 1 d . . . C21 C 0.3032(4) 0.0131(4) 0.8625(4) 0.0240(9) Uani 1 1 d . . . H21 H 0.3394 0.0409 0.9658 0.029 Uiso 1 1 calc R . . C14 C 0.3150(5) 0.3487(4) 1.4047(4) 0.0293(10) Uani 1 1 d . . . H14 H 0.3673 0.3666 1.5060 0.035 Uiso 1 1 calc R . . C7 C -0.1334(5) 0.0869(4) 0.8441(4) 0.0299(10) Uani 1 1 d . . . H7 H -0.0760 0.0175 0.8769 0.036 Uiso 1 1 calc R . . C9 C -0.3741(5) 0.1453(5) 0.7178(4) 0.0383(11) Uani 1 1 d . . . H9 H -0.4825 0.1169 0.6644 0.046 Uiso 1 1 calc R . . C19 C 0.2445(4) -0.1700(4) 0.6347(5) 0.0326(10) Uani 1 1 d . . . H19 H 0.2409 -0.2671 0.5833 0.039 Uiso 1 1 calc R . . C8 C -0.2892(5) 0.0463(4) 0.7646(4) 0.0397(11) Uani 1 1 d . . . H8 H -0.3389 -0.0516 0.7418 0.048 Uiso 1 1 calc R . . C10 C -0.3005(5) 0.2868(4) 0.7490(5) 0.0417(12) Uani 1 1 d . . . H10 H -0.3586 0.3553 0.7153 0.050 Uiso 1 1 calc R . . C20 C 0.3011(4) -0.1265(4) 0.7857(5) 0.0308(10) Uani 1 1 d . . . H20 H 0.3390 -0.1938 0.8370 0.037 Uiso 1 1 calc R . . H5A H 0.482(4) 0.378(4) 1.074(4) 0.037 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Se1 0.0267(3) 0.0278(3) 0.0249(3) 0.01159(19) 0.0071(2) -0.00030(19) P1 0.0163(6) 0.0243(5) 0.0189(6) 0.0074(4) 0.0048(4) 0.0015(4) N2 0.0130(17) 0.0252(17) 0.0178(18) 0.0082(14) 0.0054(14) 0.0026(13) N5 0.0104(18) 0.0320(19) 0.0175(18) 0.0075(14) 0.0004(14) -0.0019(14) C6 0.018(2) 0.021(2) 0.020(2) 0.0076(17) 0.0086(17) 0.0041(17) C3 0.023(2) 0.0154(19) 0.017(2) 0.0082(16) 0.0043(17) 0.0054(16) C17 0.017(2) 0.029(2) 0.024(2) 0.0081(18) 0.0041(18) 0.0041(17) C11 0.025(3) 0.021(2) 0.036(3) 0.0009(19) 0.001(2) 0.0049(19) C12 0.024(2) 0.0188(19) 0.023(2) 0.0089(17) 0.0097(18) 0.0049(16) C4 0.023(2) 0.021(2) 0.017(2) 0.0087(17) 0.0074(17) 0.0044(17) C18 0.026(2) 0.032(2) 0.026(2) 0.001(2) 0.0082(19) 0.0079(19) C15 0.030(3) 0.031(2) 0.023(2) 0.0101(19) 0.0075(19) 0.0065(19) C13 0.033(3) 0.032(2) 0.018(2) 0.0094(18) 0.012(2) 0.0045(19) C16 0.013(2) 0.026(2) 0.018(2) 0.0064(17) 0.0033(16) 0.0007(16) C21 0.024(2) 0.025(2) 0.022(2) 0.0070(18) 0.0071(18) 0.0029(18) C14 0.035(3) 0.034(2) 0.016(2) 0.0076(18) 0.0036(19) 0.005(2) C7 0.033(3) 0.027(2) 0.031(3) 0.0136(19) 0.009(2) 0.0001(19) C9 0.017(2) 0.056(3) 0.031(3) -0.003(2) 0.007(2) -0.006(2) C19 0.021(2) 0.026(2) 0.045(3) 0.000(2) 0.009(2) 0.0050(18) C8 0.037(3) 0.037(3) 0.037(3) 0.008(2) 0.009(2) -0.012(2) C10 0.026(3) 0.042(3) 0.047(3) 0.002(2) 0.002(2) 0.018(2) C20 0.020(2) 0.033(2) 0.040(3) 0.013(2) 0.007(2) 0.0047(18) _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 2.0927(10) . ? P1 N5 1.662(3) . ? P1 N2 1.690(3) . ? P1 C16 1.801(4) . ? N2 C3 1.400(4) . ? N2 C6 1.434(4) . ? N5 C4 1.419(4) . ? N5 H5A 0.90(4) . ? C6 C11 1.384(4) . ? C6 C7 1.385(5) . ? C3 C12 1.383(4) . ? C3 C4 1.398(5) . ? C17 C16 1.389(5) . ? C17 C18 1.394(5) . ? C17 H17 0.9500 . ? C11 C10 1.383(5) . ? C11 H11 0.9500 . ? C12 C13 1.394(5) . ? C12 H12 0.9500 . ? C4 C15 1.374(5) . ? C18 C19 1.387(5) . ? C18 H18 0.9500 . ? C15 C14 1.402(5) . ? C15 H15 0.9500 . ? C13 C14 1.382(5) . ? C13 H13 0.9500 . ? C16 C21 1.401(4) . ? C21 C20 1.380(5) . ? C21 H21 0.9500 . ? C14 H14 0.9500 . ? C7 C8 1.371(5) . ? C7 H7 0.9500 . ? C9 C8 1.370(5) . ? C9 C10 1.381(5) . ? C9 H9 0.9500 . ? C19 C20 1.389(5) . ? C19 H19 0.9500 . ? C8 H8 0.9500 . ? C10 H10 0.9500 . ? C20 H20 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 N5 P1 N2 92.31(15) . . ? N5 P1 C16 107.79(16) . . ? N2 P1 C16 105.72(15) . . ? N5 P1 Se1 118.57(11) . . ? N2 P1 Se1 117.44(10) . . ? C16 P1 Se1 112.70(12) . . ? C3 N2 C6 123.1(3) . . ? C3 N2 P1 112.2(2) . . ? C6 N2 P1 124.6(2) . . ? C4 N5 P1 113.1(2) . . ? C4 N5 H5A 119(2) . . ? P1 N5 H5A 124(2) . . ? C11 C6 C7 120.0(4) . . ? C11 C6 N2 119.7(3) . . ? C7 C6 N2 120.3(3) . . ? C12 C3 C4 120.5(3) . . ? C12 C3 N2 127.5(3) . . ? C4 C3 N2 112.0(3) . . ? C16 C17 C18 120.6(3) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C10 C11 C6 118.9(4) . . ? C10 C11 H11 120.5 . . ? C6 C11 H11 120.5 . . ? C3 C12 C13 118.3(3) . . ? C3 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C15 C4 C3 121.7(3) . . ? C15 C4 N5 127.8(3) . . ? C3 C4 N5 110.4(3) . . ? C19 C18 C17 119.6(4) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C4 C15 C14 117.4(4) . . ? C4 C15 H15 121.3 . . ? C14 C15 H15 121.3 . . ? C14 C13 C12 120.7(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C17 C16 C21 119.4(3) . . ? C17 C16 P1 122.0(3) . . ? C21 C16 P1 118.5(3) . . ? C20 C21 C16 119.6(4) . . ? C20 C21 H21 120.2 . . ? C16 C21 H21 120.2 . . ? C13 C14 C15 121.4(4) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C8 C7 C6 120.0(4) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C8 C9 C10 119.3(4) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C18 C19 C20 119.8(4) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C9 C8 C7 120.7(4) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C9 C10 C11 120.9(4) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C21 C20 C19 120.9(4) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? 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 N5 P1 N2 C3 0.1(2) . . . . ? C16 P1 N2 C3 109.4(2) . . . . ? Se1 P1 N2 C3 -123.9(2) . . . . ? N5 P1 N2 C6 -176.0(3) . . . . ? C16 P1 N2 C6 -66.8(3) . . . . ? Se1 P1 N2 C6 60.0(3) . . . . ? N2 P1 N5 C4 -1.3(2) . . . . ? C16 P1 N5 C4 -108.6(2) . . . . ? Se1 P1 N5 C4 121.9(2) . . . . ? C3 N2 C6 C11 103.9(4) . . . . ? P1 N2 C6 C11 -80.4(4) . . . . ? C3 N2 C6 C7 -75.6(4) . . . . ? P1 N2 C6 C7 100.1(3) . . . . ? C6 N2 C3 C12 -5.5(5) . . . . ? P1 N2 C3 C12 178.3(3) . . . . ? C6 N2 C3 C4 177.2(3) . . . . ? P1 N2 C3 C4 1.0(3) . . . . ? C7 C6 C11 C10 0.2(6) . . . . ? N2 C6 C11 C10 -179.3(3) . . . . ? C4 C3 C12 C13 -1.7(5) . . . . ? N2 C3 C12 C13 -178.7(3) . . . . ? C12 C3 C4 C15 2.0(5) . . . . ? N2 C3 C4 C15 179.5(3) . . . . ? C12 C3 C4 N5 -179.4(3) . . . . ? N2 C3 C4 N5 -1.9(4) . . . . ? P1 N5 C4 C15 -179.4(3) . . . . ? P1 N5 C4 C3 2.0(3) . . . . ? C16 C17 C18 C19 -0.2(6) . . . . ? C3 C4 C15 C14 -1.0(5) . . . . ? N5 C4 C15 C14 -179.4(3) . . . . ? C3 C12 C13 C14 0.6(5) . . . . ? C18 C17 C16 C21 0.1(5) . . . . ? C18 C17 C16 P1 -176.3(3) . . . . ? N5 P1 C16 C17 -155.8(3) . . . . ? N2 P1 C16 C17 106.4(3) . . . . ? Se1 P1 C16 C17 -23.1(3) . . . . ? N5 P1 C16 C21 27.7(3) . . . . ? N2 P1 C16 C21 -70.0(3) . . . . ? Se1 P1 C16 C21 160.5(2) . . . . ? C17 C16 C21 C20 0.9(5) . . . . ? P1 C16 C21 C20 177.4(3) . . . . ? C12 C13 C14 C15 0.3(5) . . . . ? C4 C15 C14 C13 -0.1(5) . . . . ? C11 C6 C7 C8 0.0(6) . . . . ? N2 C6 C7 C8 179.5(3) . . . . ? C17 C18 C19 C20 -0.7(6) . . . . ? C10 C9 C8 C7 1.2(6) . . . . ? C6 C7 C8 C9 -0.7(6) . . . . ? C8 C9 C10 C11 -1.1(6) . . . . ? C6 C11 C10 C9 0.4(6) . . . . ? C16 C21 C20 C19 -1.9(6) . . . . ? C18 C19 C20 C21 1.8(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5A Se1 0.90(4) 2.68(4) 3.543(3) 160(3) 2_667 _diffrn_measured_fraction_theta_max 0.743 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.673 _refine_diff_density_min -0.858 _refine_diff_density_rms 0.102 # Attachment '- 2b.CIF' data_2b _database_code_depnum_ccdc_archive 'CCDC 752126' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H23 N2 P Se' _chemical_formula_sum 'C26 H23 N2 P Se' _chemical_formula_weight 473.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 9.761(3) _cell_length_b 10.318(3) _cell_length_c 12.940(4) _cell_angle_alpha 112.187(10) _cell_angle_beta 95.998(13) _cell_angle_gamma 109.128(14) _cell_volume 1100.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3784 _cell_measurement_theta_min 1.76 _cell_measurement_theta_max 27.86 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.080 _exptl_crystal_size_min 0.020 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 1.794 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7777 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6685 _diffrn_reflns_av_R_equivalents 0.0614 _diffrn_reflns_av_sigmaI/netI 0.1028 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3806 _reflns_number_gt 2758 _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 '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^)+(0.0617P)^2^+0.2022P] 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 3806 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1063 _refine_ls_R_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.1349 _refine_ls_wR_factor_gt 0.1219 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.006 _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 Se1 Se 0.68621(6) 0.17069(7) 0.96289(4) 0.0290(2) Uani 1 1 d . . . P1 P 0.56781(15) 0.01273(15) 0.79366(11) 0.0224(3) Uani 1 1 d . . . N2 N 0.5753(5) -0.1597(5) 0.7445(3) 0.0239(10) Uani 1 1 d . . . C3 C 0.6320(5) -0.1960(6) 0.6456(4) 0.0197(11) Uani 1 1 d . . . C4 C 0.6650(6) -0.0773(6) 0.6118(4) 0.0236(12) Uani 1 1 d . . . N5 N 0.6345(5) 0.0431(5) 0.6863(3) 0.0235(10) Uani 1 1 d . . . C6 C 0.6420(6) 0.1727(6) 0.6640(5) 0.0279(13) Uani 1 1 d . . . H6A H 0.5873 0.2255 0.7127 0.034 Uiso 1 1 calc R . . H6B H 0.5880 0.1336 0.5823 0.034 Uiso 1 1 calc R . . C7 C 0.7967(6) 0.2887(6) 0.6856(4) 0.0237(12) Uani 1 1 d . . . C8 C 0.9257(6) 0.2960(7) 0.7459(4) 0.0305(13) Uani 1 1 d . . . H8A H 0.9198 0.2216 0.7736 0.037 Uiso 1 1 calc R . . C9 C 1.0639(6) 0.4095(7) 0.7672(5) 0.0364(15) Uani 1 1 d . . . H9A H 1.1518 0.4129 0.8093 0.044 Uiso 1 1 calc R . . C10 C 1.0741(7) 0.5188(7) 0.7268(5) 0.0392(16) Uani 1 1 d . . . H10A H 1.1687 0.5970 0.7409 0.047 Uiso 1 1 calc R . . C11 C 0.9460(7) 0.5123(6) 0.6665(5) 0.0376(16) Uani 1 1 d . . . H11A H 0.9520 0.5874 0.6396 0.045 Uiso 1 1 calc R . . C12 C 0.8089(7) 0.3984(6) 0.6445(4) 0.0308(14) Uani 1 1 d . . . H12A H 0.7215 0.3942 0.6010 0.037 Uiso 1 1 calc R . . C13 C 0.5291(6) -0.2620(6) 0.7998(4) 0.0279(13) Uani 1 1 d . . . H13A H 0.4496 -0.3601 0.7417 0.033 Uiso 1 1 calc R . . H13B H 0.4846 -0.2165 0.8620 0.033 Uiso 1 1 calc R . . C14 C 0.6527(6) -0.2946(6) 0.8506(4) 0.0240(12) Uani 1 1 d . . . C15 C 0.6153(7) -0.4203(6) 0.8745(4) 0.0330(14) Uani 1 1 d . . . H15A H 0.5128 -0.4864 0.8561 0.040 Uiso 1 1 calc R . . C16 C 0.7274(8) -0.4504(7) 0.9254(5) 0.0418(17) Uani 1 1 d . . . H16A H 0.7007 -0.5347 0.9439 0.050 Uiso 1 1 calc R . . C17 C 0.8769(8) -0.3582(7) 0.9490(4) 0.0384(15) Uani 1 1 d . . . H17A H 0.9534 -0.3797 0.9820 0.046 Uiso 1 1 calc R . . C18 C 0.9133(7) -0.2352(7) 0.9242(4) 0.0342(14) Uani 1 1 d . . . H18A H 1.0161 -0.1713 0.9406 0.041 Uiso 1 1 calc R . . C19 C 0.8034(6) -0.2017(6) 0.8755(4) 0.0302(14) Uani 1 1 d . . . H19A H 0.8312 -0.1156 0.8593 0.036 Uiso 1 1 calc R . . C20 C 0.6538(6) -0.3268(6) 0.5852(4) 0.0284(13) Uani 1 1 d . . . H20A H 0.6313 -0.4067 0.6084 0.034 Uiso 1 1 calc R . . C21 C 0.7100(6) -0.3377(7) 0.4890(4) 0.0308(14) Uani 1 1 d . . . H21A H 0.7254 -0.4270 0.4458 0.037 Uiso 1 1 calc R . . C22 C 0.7438(6) -0.2214(7) 0.4553(4) 0.0319(14) Uani 1 1 d . . . H22A H 0.7816 -0.2319 0.3892 0.038 Uiso 1 1 calc R . . C23 C 0.7232(6) -0.0886(7) 0.5173(4) 0.0289(13) Uani 1 1 d . . . H23A H 0.7485 -0.0077 0.4951 0.035 Uiso 1 1 calc R . . C24 C 0.3720(6) -0.0182(6) 0.7606(4) 0.0251(12) Uani 1 1 d . . . C25 C 0.3161(6) 0.0782(7) 0.8345(4) 0.0319(14) Uani 1 1 d . . . H25A H 0.3793 0.1581 0.9071 0.038 Uiso 1 1 calc R . . C26 C 0.1668(7) 0.0564(8) 0.8009(5) 0.0429(16) Uani 1 1 d . . . H26A H 0.1283 0.1218 0.8509 0.051 Uiso 1 1 calc R . . C27 C 0.0751(6) -0.0582(7) 0.6967(5) 0.0324(14) Uani 1 1 d . . . H27A H -0.0264 -0.0717 0.6747 0.039 Uiso 1 1 calc R . . C28 C 0.1304(6) -0.1564(6) 0.6215(4) 0.0247(12) Uani 1 1 d . . . H28A H 0.0669 -0.2366 0.5492 0.030 Uiso 1 1 calc R . . C29 C 0.2777(6) -0.1341(6) 0.6548(4) 0.0232(12) Uani 1 1 d . . . H29A H 0.3160 -0.1993 0.6043 0.028 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 0.0270(4) 0.0284(3) 0.0255(3) 0.0084(2) 0.0026(2) 0.0091(3) P1 0.0195(8) 0.0225(8) 0.0238(7) 0.0098(6) 0.0048(6) 0.0072(6) N2 0.026(3) 0.023(3) 0.025(2) 0.0114(19) 0.0095(18) 0.012(2) C3 0.006(3) 0.026(3) 0.024(2) 0.008(2) 0.0013(19) 0.006(2) C4 0.016(3) 0.027(3) 0.024(3) 0.010(2) 0.001(2) 0.006(2) N5 0.024(3) 0.025(3) 0.028(2) 0.016(2) 0.0090(19) 0.012(2) C6 0.027(3) 0.028(3) 0.038(3) 0.021(3) 0.012(2) 0.014(3) C7 0.021(3) 0.027(3) 0.026(3) 0.010(2) 0.013(2) 0.012(2) C8 0.026(4) 0.037(4) 0.030(3) 0.014(3) 0.006(2) 0.015(3) C9 0.021(4) 0.040(4) 0.033(3) 0.007(3) 0.002(2) 0.006(3) C10 0.024(4) 0.037(4) 0.041(3) 0.008(3) 0.016(3) 0.003(3) C11 0.052(5) 0.021(3) 0.036(3) 0.012(3) 0.021(3) 0.009(3) C12 0.034(4) 0.029(3) 0.029(3) 0.015(3) 0.012(2) 0.008(3) C13 0.027(3) 0.024(3) 0.032(3) 0.015(2) 0.013(2) 0.006(3) C14 0.032(4) 0.021(3) 0.021(2) 0.009(2) 0.006(2) 0.012(3) C15 0.044(4) 0.026(3) 0.025(3) 0.007(2) 0.010(2) 0.014(3) C16 0.076(6) 0.033(4) 0.028(3) 0.016(3) 0.009(3) 0.034(4) C17 0.051(5) 0.049(4) 0.022(3) 0.011(3) 0.004(3) 0.036(4) C18 0.030(4) 0.039(4) 0.027(3) 0.006(3) 0.004(2) 0.016(3) C19 0.039(4) 0.024(3) 0.025(3) 0.010(2) 0.008(2) 0.012(3) C20 0.030(3) 0.033(3) 0.025(3) 0.014(3) 0.006(2) 0.014(3) C21 0.019(3) 0.033(3) 0.027(3) 0.003(3) 0.005(2) 0.008(3) C22 0.026(3) 0.042(4) 0.022(3) 0.009(3) 0.007(2) 0.012(3) C23 0.022(3) 0.039(4) 0.028(3) 0.017(3) 0.006(2) 0.011(3) C24 0.028(3) 0.028(3) 0.024(3) 0.014(2) 0.006(2) 0.013(3) C25 0.023(3) 0.035(4) 0.025(3) 0.001(2) -0.001(2) 0.013(3) C26 0.035(4) 0.060(5) 0.033(3) 0.008(3) 0.011(3) 0.032(4) C27 0.022(3) 0.043(4) 0.039(3) 0.021(3) 0.011(3) 0.017(3) C28 0.019(3) 0.023(3) 0.027(3) 0.010(2) 0.005(2) 0.002(2) C29 0.021(3) 0.023(3) 0.027(3) 0.012(2) 0.009(2) 0.008(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 2.0804(16) . ? P1 N2 1.678(5) . ? P1 N5 1.684(4) . ? P1 C24 1.806(6) . ? N2 C3 1.416(6) . ? N2 C13 1.467(6) . ? C3 C20 1.380(8) . ? C3 C4 1.404(7) . ? C4 C23 1.383(6) . ? C4 N5 1.399(7) . ? N5 C6 1.452(6) . ? C6 C7 1.505(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.375(7) . ? C7 C12 1.400(7) . ? C8 C9 1.382(8) . ? C8 H8A 0.9500 . ? C9 C10 1.392(8) . ? C9 H9A 0.9500 . ? C10 C11 1.371(9) . ? C10 H10A 0.9500 . ? C11 C12 1.375(8) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C14 1.506(8) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C19 1.389(8) . ? C14 C15 1.388(7) . ? C15 C16 1.398(9) . ? C15 H15A 0.9500 . ? C16 C17 1.380(9) . ? C16 H16A 0.9500 . ? C17 C18 1.369(8) . ? C17 H17A 0.9500 . ? C18 C19 1.391(8) . ? C18 H18A 0.9500 . ? C19 H19A 0.9500 . ? C20 C21 1.392(7) . ? C20 H20A 0.9500 . ? C21 C22 1.381(8) . ? C21 H21A 0.9500 . ? C22 C23 1.395(8) . ? C22 H22A 0.9500 . ? C23 H23A 0.9500 . ? C24 C29 1.390(7) . ? C24 C25 1.396(8) . ? C25 C26 1.394(8) . ? C25 H25A 0.9500 . ? C26 C27 1.366(8) . ? C26 H26A 0.9500 . ? C27 C28 1.410(8) . ? C27 H27A 0.9500 . ? C28 C29 1.372(7) . ? C28 H28A 0.9500 . ? C29 H29A 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 N2 P1 N5 91.2(2) . . ? N2 P1 C24 107.2(2) . . ? N5 P1 C24 106.2(2) . . ? N2 P1 Se1 118.20(16) . . ? N5 P1 Se1 117.75(16) . . ? C24 P1 Se1 113.65(18) . . ? C3 N2 C13 123.4(4) . . ? C3 N2 P1 113.5(3) . . ? C13 N2 P1 123.1(3) . . ? C20 C3 C4 121.4(4) . . ? C20 C3 N2 128.1(4) . . ? C4 C3 N2 110.5(4) . . ? C23 C4 N5 128.8(5) . . ? C23 C4 C3 120.1(5) . . ? N5 C4 C3 111.0(4) . . ? C4 N5 C6 122.6(4) . . ? C4 N5 P1 113.8(3) . . ? C6 N5 P1 123.2(3) . . ? N5 C6 C7 116.4(4) . . ? N5 C6 H6A 108.2 . . ? C7 C6 H6A 108.2 . . ? N5 C6 H6B 108.2 . . ? C7 C6 H6B 108.2 . . ? H6A C6 H6B 107.3 . . ? C8 C7 C12 118.2(5) . . ? C8 C7 C6 124.1(5) . . ? C12 C7 C6 117.7(5) . . ? C7 C8 C9 121.3(5) . . ? C7 C8 H8A 119.4 . . ? C9 C8 H8A 119.4 . . ? C8 C9 C10 119.9(6) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? C11 C10 C9 119.3(5) . . ? C11 C10 H10A 120.4 . . ? C9 C10 H10A 120.4 . . ? C10 C11 C12 120.7(6) . . ? C10 C11 H11A 119.7 . . ? C12 C11 H11A 119.7 . . ? C11 C12 C7 120.7(6) . . ? C11 C12 H12A 119.6 . . ? C7 C12 H12A 119.6 . . ? N2 C13 C14 115.2(4) . . ? N2 C13 H13A 108.5 . . ? C14 C13 H13A 108.5 . . ? N2 C13 H13B 108.5 . . ? C14 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C19 C14 C15 118.9(5) . . ? C19 C14 C13 122.0(5) . . ? C15 C14 C13 119.2(5) . . ? C14 C15 C16 120.4(6) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? C17 C16 C15 120.3(6) . . ? C17 C16 H16A 119.9 . . ? C15 C16 H16A 119.9 . . ? C18 C17 C16 119.1(6) . . ? C18 C17 H17A 120.5 . . ? C16 C17 H17A 120.5 . . ? C17 C18 C19 121.5(6) . . ? C17 C18 H18A 119.2 . . ? C19 C18 H18A 119.2 . . ? C14 C19 C18 119.8(5) . . ? C14 C19 H19A 120.1 . . ? C18 C19 H19A 120.1 . . ? C3 C20 C21 117.9(5) . . ? C3 C20 H20A 121.1 . . ? C21 C20 H20A 121.1 . . ? C22 C21 C20 121.3(5) . . ? C22 C21 H21A 119.4 . . ? C20 C21 H21A 119.4 . . ? C21 C22 C23 120.7(5) . . ? C21 C22 H22A 119.6 . . ? C23 C22 H22A 119.6 . . ? C4 C23 C22 118.6(5) . . ? C4 C23 H23A 120.7 . . ? C22 C23 H23A 120.7 . . ? C29 C24 C25 119.3(5) . . ? C29 C24 P1 118.8(4) . . ? C25 C24 P1 121.7(4) . . ? C24 C25 C26 119.4(5) . . ? C24 C25 H25A 120.3 . . ? C26 C25 H25A 120.3 . . ? C27 C26 C25 120.7(5) . . ? C27 C26 H26A 119.7 . . ? C25 C26 H26A 119.7 . . ? C26 C27 C28 120.3(5) . . ? C26 C27 H27A 119.8 . . ? C28 C27 H27A 119.8 . . ? C29 C28 C27 118.8(5) . . ? C29 C28 H28A 120.6 . . ? C27 C28 H28A 120.6 . . ? C28 C29 C24 121.5(5) . . ? C28 C29 H29A 119.3 . . ? C24 C29 H29A 119.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 P1 N2 C3 1.1(4) . . . . ? C24 P1 N2 C3 108.5(4) . . . . ? Se1 P1 N2 C3 -121.6(3) . . . . ? N5 P1 N2 C13 -179.6(4) . . . . ? C24 P1 N2 C13 -72.2(4) . . . . ? Se1 P1 N2 C13 57.8(4) . . . . ? C13 N2 C3 C20 -0.1(8) . . . . ? P1 N2 C3 C20 179.3(4) . . . . ? C13 N2 C3 C4 179.4(4) . . . . ? P1 N2 C3 C4 -1.3(5) . . . . ? C20 C3 C4 C23 -1.1(7) . . . . ? N2 C3 C4 C23 179.4(4) . . . . ? C20 C3 C4 N5 -179.7(5) . . . . ? N2 C3 C4 N5 0.8(6) . . . . ? C23 C4 N5 C6 8.8(8) . . . . ? C3 C4 N5 C6 -172.7(4) . . . . ? C23 C4 N5 P1 -178.5(4) . . . . ? C3 C4 N5 P1 0.0(5) . . . . ? N2 P1 N5 C4 -0.6(4) . . . . ? C24 P1 N5 C4 -108.9(4) . . . . ? Se1 P1 N5 C4 122.4(3) . . . . ? N2 P1 N5 C6 172.1(4) . . . . ? C24 P1 N5 C6 63.8(4) . . . . ? Se1 P1 N5 C6 -64.9(4) . . . . ? C4 N5 C6 C7 -75.2(6) . . . . ? P1 N5 C6 C7 112.8(4) . . . . ? N5 C6 C7 C8 -14.0(7) . . . . ? N5 C6 C7 C12 168.0(4) . . . . ? C12 C7 C8 C9 0.9(8) . . . . ? C6 C7 C8 C9 -177.1(5) . . . . ? C7 C8 C9 C10 -0.2(8) . . . . ? C8 C9 C10 C11 0.2(8) . . . . ? C9 C10 C11 C12 -0.8(8) . . . . ? C10 C11 C12 C7 1.5(8) . . . . ? C8 C7 C12 C11 -1.5(7) . . . . ? C6 C7 C12 C11 176.6(5) . . . . ? C3 N2 C13 C14 63.7(6) . . . . ? P1 N2 C13 C14 -115.6(5) . . . . ? N2 C13 C14 C19 18.9(7) . . . . ? N2 C13 C14 C15 -161.8(4) . . . . ? C19 C14 C15 C16 1.6(7) . . . . ? C13 C14 C15 C16 -177.8(5) . . . . ? C14 C15 C16 C17 -2.1(8) . . . . ? C15 C16 C17 C18 1.4(8) . . . . ? C16 C17 C18 C19 -0.3(8) . . . . ? C15 C14 C19 C18 -0.4(7) . . . . ? C13 C14 C19 C18 178.9(5) . . . . ? C17 C18 C19 C14 -0.2(8) . . . . ? C4 C3 C20 C21 0.0(7) . . . . ? N2 C3 C20 C21 179.4(5) . . . . ? C3 C20 C21 C22 0.4(8) . . . . ? C20 C21 C22 C23 0.3(8) . . . . ? N5 C4 C23 C22 -179.9(5) . . . . ? C3 C4 C23 C22 1.8(7) . . . . ? C21 C22 C23 C4 -1.4(8) . . . . ? N2 P1 C24 C29 -40.0(4) . . . . ? N5 P1 C24 C29 56.5(4) . . . . ? Se1 P1 C24 C29 -172.5(3) . . . . ? N2 P1 C24 C25 144.9(4) . . . . ? N5 P1 C24 C25 -118.6(4) . . . . ? Se1 P1 C24 C25 12.5(5) . . . . ? C29 C24 C25 C26 0.1(8) . . . . ? P1 C24 C25 C26 175.1(4) . . . . ? C24 C25 C26 C27 0.0(9) . . . . ? C25 C26 C27 C28 0.1(9) . . . . ? C26 C27 C28 C29 -0.4(8) . . . . ? C27 C28 C29 C24 0.5(7) . . . . ? C25 C24 C29 C28 -0.3(7) . . . . ? P1 C24 C29 C28 -175.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.945 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.957 _refine_diff_density_max 0.443 _refine_diff_density_min -0.618 _refine_diff_density_rms 0.095 # Attachment '- 4b.CIF' data_hua29 _database_code_depnum_ccdc_archive 'CCDC 752127' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 N P S Se' _chemical_formula_sum 'C12 H10 N P S Se' _chemical_formula_weight 310.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 5.3325(7) _cell_length_b 21.151(3) _cell_length_c 10.6495(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.255(5) _cell_angle_gamma 90.00 _cell_volume 1196.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4205 _cell_measurement_theta_min 2.7200 _cell_measurement_theta_max 28.4758 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1300 _exptl_crystal_size_mid 0.1300 _exptl_crystal_size_min 0.1300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.723 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 3.416 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6620 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _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 '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7419 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2150 _reflns_number_gt 2003 _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 '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. The NH hydrogen atom was located from a difference map and refined isotropically subject to a distance constraint. ; _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^)+(0.0228P)^2^+0.7113P] 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 2150 _refine_ls_number_parameters 150 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_ref 0.0506 _refine_ls_wR_factor_gt 0.0486 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.052 _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 0.61386(4) 0.153847(10) 0.64502(2) 0.01627(8) Uani 1 1 d . . . S1 S 0.60987(10) 0.24682(2) 0.36454(5) 0.01359(13) Uani 1 1 d . . . P1 P 0.80359(11) 0.18240(3) 0.49003(5) 0.01159(13) Uani 1 1 d . . . C1 C 0.8062(4) 0.31056(10) 0.41907(19) 0.0123(5) Uani 1 1 d . . . C2 C 1.0239(4) 0.29356(10) 0.49514(18) 0.0117(4) Uani 1 1 d . . . N2 N 1.0538(4) 0.22913(8) 0.51960(17) 0.0134(4) Uani 1 1 d D . . H2N H 1.192(4) 0.2143(12) 0.568(2) 0.030(7) Uiso 1 1 d D . . C3 C 1.1960(4) 0.34006(10) 0.5380(2) 0.0147(5) Uani 1 1 d . . . H3A H 1.3433 0.3292 0.5905 0.018 Uiso 1 1 calc R . . C4 C 1.1499(4) 0.40231(10) 0.5030(2) 0.0162(5) Uani 1 1 d . . . H4A H 1.2684 0.4341 0.5306 0.019 Uiso 1 1 calc R . . C5 C 0.9327(4) 0.41913(10) 0.4281(2) 0.0167(5) Uani 1 1 d . . . H5A H 0.9036 0.4621 0.4055 0.020 Uiso 1 1 calc R . . C6 C 0.7581(4) 0.37317(10) 0.38638(19) 0.0143(5) Uani 1 1 d . . . H6A H 0.6083 0.3845 0.3362 0.017 Uiso 1 1 calc R . . C7 C 0.9082(4) 0.11750(10) 0.39822(19) 0.0130(5) Uani 1 1 d . . . C8 C 0.8011(4) 0.05777(10) 0.4064(2) 0.0171(5) Uani 1 1 d . . . H8A H 0.6694 0.0512 0.4592 0.021 Uiso 1 1 calc R . . C9 C 0.8872(5) 0.00786(11) 0.3372(2) 0.0225(5) Uani 1 1 d . . . H9A H 0.8133 -0.0328 0.3419 0.027 Uiso 1 1 calc R . . C10 C 1.0810(5) 0.01768(12) 0.2613(2) 0.0246(6) Uani 1 1 d . . . H10A H 1.1431 -0.0168 0.2160 0.029 Uiso 1 1 calc R . . C11 C 1.1853(5) 0.07734(12) 0.2508(2) 0.0226(5) Uani 1 1 d . . . H11A H 1.3162 0.0838 0.1975 0.027 Uiso 1 1 calc R . . C12 C 1.0976(4) 0.12740(11) 0.3185(2) 0.0175(5) Uani 1 1 d . . . H12A H 1.1666 0.1685 0.3105 0.021 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 0.01478(14) 0.02140(14) 0.01313(13) 0.00467(9) 0.00389(9) 0.00238(9) S1 0.0124(3) 0.0135(3) 0.0142(3) 0.0023(2) -0.0023(2) -0.0007(2) P1 0.0107(3) 0.0129(3) 0.0112(3) 0.0009(2) 0.0010(2) 0.0004(2) C1 0.0113(12) 0.0158(11) 0.0104(11) -0.0018(8) 0.0035(8) -0.0013(9) C2 0.0121(12) 0.0158(11) 0.0079(10) -0.0017(8) 0.0043(8) 0.0011(9) N2 0.0108(11) 0.0123(9) 0.0165(10) 0.0016(7) -0.0020(8) 0.0024(7) C3 0.0126(13) 0.0185(12) 0.0129(11) -0.0034(9) 0.0015(9) -0.0005(9) C4 0.0160(13) 0.0155(11) 0.0178(12) -0.0063(9) 0.0047(9) -0.0043(9) C5 0.0221(14) 0.0112(11) 0.0179(12) -0.0009(9) 0.0067(10) 0.0008(9) C6 0.0155(13) 0.0174(11) 0.0107(11) 0.0003(9) 0.0043(9) 0.0039(9) C7 0.0124(12) 0.0150(11) 0.0111(10) -0.0004(9) -0.0015(9) 0.0043(9) C8 0.0180(13) 0.0181(12) 0.0149(12) 0.0019(9) -0.0001(9) -0.0004(9) C9 0.0328(15) 0.0148(12) 0.0184(12) -0.0008(9) -0.0055(11) 0.0019(10) C10 0.0281(15) 0.0249(13) 0.0191(13) -0.0097(10) -0.0056(11) 0.0093(11) C11 0.0158(13) 0.0346(14) 0.0172(12) -0.0061(10) 0.0007(10) 0.0033(10) C12 0.0154(13) 0.0205(12) 0.0160(12) -0.0019(9) -0.0016(9) -0.0012(10) _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 2.1021(6) . ? S1 C1 1.772(2) . ? S1 P1 2.1110(8) . ? P1 N2 1.6671(19) . ? P1 C7 1.803(2) . ? C1 C6 1.387(3) . ? C1 C2 1.400(3) . ? C2 C3 1.393(3) . ? C2 N2 1.394(3) . ? N2 H2N 0.912(16) . ? C3 C4 1.384(3) . ? C3 H3A 0.9500 . ? C4 C5 1.391(3) . ? C4 H4A 0.9500 . ? C5 C6 1.390(3) . ? C5 H5A 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.392(3) . ? C7 C12 1.394(3) . ? C8 C9 1.389(3) . ? C8 H8A 0.9500 . ? C9 C10 1.384(4) . ? C9 H9A 0.9500 . ? C10 C11 1.388(4) . ? C10 H10A 0.9500 . ? C11 C12 1.386(3) . ? C11 H11A 0.9500 . ? C12 H12A 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 C1 S1 P1 92.49(7) . . ? N2 P1 C7 105.77(10) . . ? N2 P1 Se1 117.15(7) . . ? C7 P1 Se1 113.71(7) . . ? N2 P1 S1 94.23(7) . . ? C7 P1 S1 107.81(7) . . ? Se1 P1 S1 116.09(3) . . ? C6 C1 C2 121.0(2) . . ? C6 C1 S1 123.65(17) . . ? C2 C1 S1 115.33(16) . . ? C3 C2 N2 124.6(2) . . ? C3 C2 C1 119.64(19) . . ? N2 C2 C1 115.71(19) . . ? C2 N2 P1 117.94(15) . . ? C2 N2 H2N 120.9(17) . . ? P1 N2 H2N 119.5(16) . . ? C4 C3 C2 119.2(2) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 121.0(2) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C6 C5 C4 120.2(2) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C1 C6 C5 119.0(2) . . ? C1 C6 H6A 120.5 . . ? C5 C6 H6A 120.5 . . ? C8 C7 C12 119.9(2) . . ? C8 C7 P1 120.53(17) . . ? C12 C7 P1 119.56(17) . . ? C9 C8 C7 119.9(2) . . ? C9 C8 H8A 120.0 . . ? C7 C8 H8A 120.0 . . ? C10 C9 C8 119.7(2) . . ? C10 C9 H9A 120.1 . . ? C8 C9 H9A 120.1 . . ? C9 C10 C11 120.6(2) . . ? C9 C10 H10A 119.7 . . ? C11 C10 H10A 119.7 . . ? C12 C11 C10 119.7(2) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? C11 C12 C7 120.0(2) . . ? C11 C12 H12A 120.0 . . ? C7 C12 H12A 120.0 . . ? 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 C1 S1 P1 N2 -16.59(9) . . . . ? C1 S1 P1 C7 -124.65(10) . . . . ? C1 S1 P1 Se1 106.48(7) . . . . ? P1 S1 C1 C6 -170.15(17) . . . . ? P1 S1 C1 C2 12.32(15) . . . . ? C6 C1 C2 C3 -0.5(3) . . . . ? S1 C1 C2 C3 177.10(15) . . . . ? C6 C1 C2 N2 -178.84(18) . . . . ? S1 C1 C2 N2 -1.2(2) . . . . ? C3 C2 N2 P1 166.22(17) . . . . ? C1 C2 N2 P1 -15.5(2) . . . . ? C7 P1 N2 C2 130.43(15) . . . . ? Se1 P1 N2 C2 -101.66(14) . . . . ? S1 P1 N2 C2 20.58(15) . . . . ? N2 C2 C3 C4 177.37(19) . . . . ? C1 C2 C3 C4 -0.8(3) . . . . ? C2 C3 C4 C5 1.3(3) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C2 C1 C6 C5 1.4(3) . . . . ? S1 C1 C6 C5 -176.03(16) . . . . ? C4 C5 C6 C1 -0.9(3) . . . . ? N2 P1 C7 C8 149.43(18) . . . . ? Se1 P1 C7 C8 19.5(2) . . . . ? S1 P1 C7 C8 -110.72(17) . . . . ? N2 P1 C7 C12 -30.6(2) . . . . ? Se1 P1 C7 C12 -160.57(15) . . . . ? S1 P1 C7 C12 69.23(18) . . . . ? C12 C7 C8 C9 1.4(3) . . . . ? P1 C7 C8 C9 -178.63(17) . . . . ? C7 C8 C9 C10 0.6(3) . . . . ? C8 C9 C10 C11 -1.9(4) . . . . ? C9 C10 C11 C12 1.1(4) . . . . ? C10 C11 C12 C7 1.0(3) . . . . ? C8 C7 C12 C11 -2.3(3) . . . . ? P1 C7 C12 C11 177.79(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N Se1 0.912(16) 2.654(18) 3.5368(19) 163(2) 1_655 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.429 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.069 # Attachment '- 6a.cif' data__hua16_in_P21/c _database_code_depnum_ccdc_archive 'CCDC 752128' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C16 H11 P S2 Se ' _chemical_formula_moiety 'C16 H11 P S2 Se ' _chemical_formula_weight 377.32 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 8.5293(6) _cell_length_b 9.9922(7) _cell_length_c 18.1201(12) _cell_angle_alpha 90.0000 _cell_angle_beta 94.3449(13) _cell_angle_gamma 90.0000 _cell_volume 1539.87(18) _cell_formula_units_Z 4 _cell_measurement_reflns_used 13696 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _cell_measurement_temperature 125.1 #------------------------------------------------------------------------------ _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.627 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752.00 _exptl_absorpt_coefficient_mu 2.799 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.535 _exptl_absorpt_correction_T_max 0.756 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku SCXmini' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 6.85 _diffrn_reflns_number 15498 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3516 _reflns_number_gt 2729 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.0888 _refine_ls_wR_factor_gt 0.0819 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 3516 _refine_ls_number_parameters 182 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0327P)^2^+1.5033P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_shift/su_max 0.0010 _refine_diff_density_max 0.94 _refine_diff_density_min -0.35 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; P P 0.102 0.094 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Se Se -0.093 2.226 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Se(1) Se 0.55670(4) 0.49431(4) 0.68525(2) 0.02572(11) Uani 1.00 1 d . . . S(1) S 0.64537(11) 0.62990(9) 0.51660(5) 0.0248(2) Uani 1.00 1 d . . . S(2) S 0.52537(10) 0.82537(9) 0.64193(5) 0.0230(2) Uani 1.00 1 d . . . P(1) P 0.65659(10) 0.65441(9) 0.63059(5) 0.0197(2) Uani 1.00 1 d . . . C(1) C 0.7245(3) 0.7863(3) 0.48833(19) 0.0227(7) Uani 1.00 1 d . . . C(2) C 0.8017(4) 0.7755(3) 0.4245(2) 0.0309(8) Uani 1.00 1 d . . . C(3) C 0.8623(4) 0.8876(4) 0.3905(2) 0.0366(9) Uani 1.00 1 d . . . C(4) C 0.8490(4) 1.0099(4) 0.4214(2) 0.0323(8) Uani 1.00 1 d . . . C(5) C 0.7704(4) 1.0273(3) 0.48715(19) 0.0236(7) Uani 1.00 1 d . . . C(6) C 0.7582(4) 1.1577(3) 0.5161(2) 0.0284(8) Uani 1.00 1 d . . . C(7) C 0.6817(4) 1.1793(3) 0.5787(2) 0.0311(8) Uani 1.00 1 d . . . C(8) C 0.6176(4) 1.0712(3) 0.6150(2) 0.0258(8) Uani 1.00 1 d . . . C(9) C 0.6271(3) 0.9428(3) 0.58865(18) 0.0210(7) Uani 1.00 1 d . . . C(10) C 0.7042(3) 0.9139(3) 0.52265(18) 0.0216(7) Uani 1.00 1 d . . . C(11) C 0.8593(3) 0.6902(3) 0.66120(18) 0.0213(7) Uani 1.00 1 d . . . C(12) C 0.9767(4) 0.6098(3) 0.6350(2) 0.0305(8) Uani 1.00 1 d . . . C(13) C 1.1318(4) 0.6252(3) 0.6646(2) 0.0349(9) Uani 1.00 1 d . . . C(14) C 1.1674(4) 0.7200(3) 0.7183(2) 0.0311(9) Uani 1.00 1 d . . . C(15) C 1.0528(4) 0.8023(4) 0.7428(2) 0.0315(9) Uani 1.00 1 d . . . C(16) C 0.8970(4) 0.7870(3) 0.71453(19) 0.0268(8) Uani 1.00 1 d . . . H(1) H 0.8140 0.6897 0.4031 0.037 Uiso 1.00 1 c R . . H(2) H 0.9127 0.8780 0.3458 0.044 Uiso 1.00 1 c R . . H(3) H 0.8930 1.0855 0.3988 0.039 Uiso 1.00 1 c R . . H(4) H 0.8035 1.2310 0.4920 0.034 Uiso 1.00 1 c R . . H(5) H 0.6722 1.2675 0.5974 0.037 Uiso 1.00 1 c R . . H(6) H 0.5662 1.0869 0.6588 0.031 Uiso 1.00 1 c R . . H(7) H 0.9515 0.5452 0.5975 0.037 Uiso 1.00 1 c R . . H(8) H 1.2126 0.5703 0.6476 0.042 Uiso 1.00 1 c R . . H(9) H 1.2727 0.7288 0.7388 0.037 Uiso 1.00 1 c R . . H(10) H 1.0796 0.8692 0.7787 0.038 Uiso 1.00 1 c R . . H(11) H 0.8171 0.8426 0.7317 0.032 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Se(1) 0.02099(18) 0.02253(19) 0.0340(2) 0.00015(16) 0.00466(14) 0.00545(16) S(1) 0.0286(4) 0.0225(4) 0.0227(4) -0.0001(3) -0.0008(3) -0.0037(3) S(2) 0.0209(4) 0.0233(4) 0.0253(4) 0.0043(3) 0.0046(3) 0.0013(3) P(1) 0.0173(4) 0.0197(4) 0.0220(4) 0.0013(3) 0.0008(3) 0.0007(3) C(1) 0.0235(18) 0.0237(18) 0.0202(18) 0.0050(14) -0.0022(13) 0.0017(14) C(2) 0.037(2) 0.029(2) 0.027(2) 0.0077(17) 0.0049(16) -0.0051(16) C(3) 0.044(2) 0.042(2) 0.026(2) 0.0032(19) 0.0105(18) 0.0014(18) C(4) 0.038(2) 0.035(2) 0.023(2) -0.0017(19) 0.0021(16) 0.0075(17) C(5) 0.0227(18) 0.026(2) 0.0213(18) 0.0043(14) -0.0058(14) 0.0030(14) C(6) 0.032(2) 0.0231(19) 0.030(2) -0.0006(16) -0.0033(16) 0.0062(15) C(7) 0.038(2) 0.0220(19) 0.032(2) 0.0029(17) -0.0043(17) -0.0015(16) C(8) 0.028(2) 0.025(2) 0.0240(19) 0.0046(15) -0.0014(15) -0.0043(15) C(9) 0.0195(17) 0.0212(17) 0.0215(18) 0.0046(14) -0.0038(14) 0.0022(14) C(10) 0.0186(17) 0.0257(19) 0.0194(18) -0.0004(14) -0.0054(13) 0.0025(14) C(11) 0.0163(16) 0.0246(18) 0.0228(18) 0.0001(14) 0.0001(13) 0.0085(14) C(12) 0.0245(19) 0.0242(19) 0.043(2) 0.0014(15) -0.0001(16) -0.0003(17) C(13) 0.0211(19) 0.029(2) 0.055(2) 0.0025(16) 0.0027(17) 0.0061(19) C(14) 0.0186(18) 0.039(2) 0.035(2) -0.0080(16) -0.0024(15) 0.0169(17) C(15) 0.026(2) 0.045(2) 0.023(2) -0.0100(18) 0.0009(15) 0.0028(17) C(16) 0.0252(19) 0.037(2) 0.0184(18) -0.0009(16) 0.0022(14) 0.0027(15) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR97 _computing_structure_refinement SHELXL _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Se(1) P(1) 2.0962(9) yes . . S(1) P(1) 2.0750(12) yes . . S(1) C(1) 1.793(3) yes . . S(2) P(1) 2.0610(12) yes . . S(2) C(9) 1.786(3) yes . . P(1) C(11) 1.811(3) yes . . C(1) C(2) 1.378(5) yes . . C(1) C(10) 1.435(4) yes . . C(2) C(3) 1.397(5) yes . . C(3) C(4) 1.352(5) yes . . C(4) C(5) 1.422(5) yes . . C(5) C(6) 1.412(4) yes . . C(5) C(10) 1.439(4) yes . . C(6) C(7) 1.367(5) yes . . C(7) C(8) 1.398(5) yes . . C(8) C(9) 1.373(4) yes . . C(9) C(10) 1.437(4) yes . . C(11) C(12) 1.395(4) yes . . C(11) C(16) 1.388(4) yes . . C(12) C(13) 1.398(5) yes . . C(13) C(14) 1.375(5) yes . . C(14) C(15) 1.376(5) yes . . C(15) C(16) 1.396(4) yes . . C(2) H(1) 0.950 no . . C(3) H(2) 0.950 no . . C(4) H(3) 0.950 no . . C(6) H(4) 0.950 no . . C(7) H(5) 0.950 no . . C(8) H(6) 0.950 no . . C(12) H(7) 0.950 no . . C(13) H(8) 0.950 no . . C(14) H(9) 0.950 no . . C(15) H(10) 0.950 no . . C(16) H(11) 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 P(1) S(1) C(1) 101.04(11) yes . . . P(1) S(2) C(9) 101.58(11) yes . . . Se(1) P(1) S(1) 112.99(4) yes . . . Se(1) P(1) S(2) 110.01(4) yes . . . Se(1) P(1) C(11) 114.75(11) yes . . . S(1) P(1) S(2) 102.28(5) yes . . . S(1) P(1) C(11) 107.41(11) yes . . . S(2) P(1) C(11) 108.60(11) yes . . . S(1) C(1) C(2) 112.7(2) yes . . . S(1) C(1) C(10) 126.2(2) yes . . . C(2) C(1) C(10) 121.0(3) yes . . . C(1) C(2) C(3) 121.6(3) yes . . . C(2) C(3) C(4) 119.8(3) yes . . . C(3) C(4) C(5) 121.1(3) yes . . . C(4) C(5) C(6) 118.5(3) yes . . . C(4) C(5) C(10) 120.3(3) yes . . . C(6) C(5) C(10) 121.2(3) yes . . . C(5) C(6) C(7) 120.5(3) yes . . . C(6) C(7) C(8) 119.8(3) yes . . . C(7) C(8) C(9) 121.6(3) yes . . . S(2) C(9) C(8) 112.5(2) yes . . . S(2) C(9) C(10) 126.1(2) yes . . . C(8) C(9) C(10) 121.3(3) yes . . . C(1) C(10) C(5) 116.2(3) yes . . . C(1) C(10) C(9) 128.1(3) yes . . . C(5) C(10) C(9) 115.7(3) yes . . . P(1) C(11) C(12) 118.4(2) yes . . . P(1) C(11) C(16) 121.1(2) yes . . . C(12) C(11) C(16) 120.3(3) yes . . . C(11) C(12) C(13) 119.3(3) yes . . . C(12) C(13) C(14) 119.9(3) yes . . . C(13) C(14) C(15) 121.0(3) yes . . . C(14) C(15) C(16) 119.8(3) yes . . . C(11) C(16) C(15) 119.7(3) yes . . . C(1) C(2) H(1) 119.2 no . . . C(3) C(2) H(1) 119.2 no . . . C(2) C(3) H(2) 120.1 no . . . C(4) C(3) H(2) 120.1 no . . . C(3) C(4) H(3) 119.4 no . . . C(5) C(4) H(3) 119.4 no . . . C(5) C(6) H(4) 119.8 no . . . C(7) C(6) H(4) 119.8 no . . . C(6) C(7) H(5) 120.1 no . . . C(8) C(7) H(5) 120.1 no . . . C(7) C(8) H(6) 119.2 no . . . C(9) C(8) H(6) 119.2 no . . . C(11) C(12) H(7) 120.4 no . . . C(13) C(12) H(7) 120.4 no . . . C(12) C(13) H(8) 120.0 no . . . C(14) C(13) H(8) 120.0 no . . . C(13) C(14) H(9) 119.5 no . . . C(15) C(14) H(9) 119.5 no . . . C(14) C(15) H(10) 120.1 no . . . C(16) C(15) H(10) 120.1 no . . . C(11) C(16) H(11) 120.2 no . . . C(15) C(16) H(11) 120.2 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 P(1) S(1) C(1) C(2) 149.7(2) ? . . . . P(1) S(1) C(1) C(10) -34.7(3) ? . . . . C(1) S(1) P(1) Se(1) 175.68(11) ? . . . . C(1) S(1) P(1) S(2) 57.46(12) ? . . . . C(1) S(1) P(1) C(11) -56.77(16) ? . . . . P(1) S(2) C(9) C(8) -149.4(2) ? . . . . P(1) S(2) C(9) C(10) 34.3(2) ? . . . . C(9) S(2) P(1) Se(1) -177.71(11) ? . . . . C(9) S(2) P(1) S(1) -57.41(11) ? . . . . C(9) S(2) P(1) C(11) 55.94(16) ? . . . . Se(1) P(1) C(11) C(12) 79.2(2) ? . . . . Se(1) P(1) C(11) C(16) -95.0(2) ? . . . . S(1) P(1) C(11) C(12) -47.4(3) ? . . . . S(1) P(1) C(11) C(16) 138.5(2) ? . . . . S(2) P(1) C(11) C(12) -157.3(2) ? . . . . S(2) P(1) C(11) C(16) 28.5(3) ? . . . . S(1) C(1) C(2) C(3) 175.5(2) ? . . . . S(1) C(1) C(10) C(5) -176.0(2) ? . . . . S(1) C(1) C(10) C(9) 4.6(5) ? . . . . C(2) C(1) C(10) C(5) -0.8(4) ? . . . . C(2) C(1) C(10) C(9) 179.9(2) ? . . . . C(10) C(1) C(2) C(3) -0.3(5) ? . . . . C(1) C(2) C(3) C(4) 1.6(5) ? . . . . C(2) C(3) C(4) C(5) -1.7(5) ? . . . . C(3) C(4) C(5) C(6) -179.0(3) ? . . . . C(3) C(4) C(5) C(10) 0.6(5) ? . . . . C(4) C(5) C(6) C(7) 179.1(3) ? . . . . C(4) C(5) C(10) C(1) 0.7(4) ? . . . . C(4) C(5) C(10) C(9) -179.9(2) ? . . . . C(6) C(5) C(10) C(1) -179.7(3) ? . . . . C(6) C(5) C(10) C(9) -0.3(4) ? . . . . C(10) C(5) C(6) C(7) -0.5(5) ? . . . . C(5) C(6) C(7) C(8) 1.2(5) ? . . . . C(6) C(7) C(8) C(9) -1.1(5) ? . . . . C(7) C(8) C(9) S(2) -176.3(2) ? . . . . C(7) C(8) C(9) C(10) 0.2(4) ? . . . . S(2) C(9) C(10) C(1) -4.2(4) ? . . . . S(2) C(9) C(10) C(5) 176.5(2) ? . . . . C(8) C(9) C(10) C(1) 179.8(3) ? . . . . C(8) C(9) C(10) C(5) 0.4(4) ? . . . . P(1) C(11) C(12) C(13) -172.4(2) ? . . . . P(1) C(11) C(16) C(15) 173.1(2) ? . . . . C(12) C(11) C(16) C(15) -1.0(5) ? . . . . C(16) C(11) C(12) C(13) 1.8(5) ? . . . . C(11) C(12) C(13) C(14) -0.7(5) ? . . . . C(12) C(13) C(14) C(15) -1.2(6) ? . . . . C(13) C(14) C(15) C(16) 2.0(5) ? . . . . C(14) C(15) C(16) C(11) -0.9(5) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 Se(1) S(1) 3.4780(9) ? . . Se(1) S(2) 3.4057(9) ? . . Se(1) C(11) 3.294(3) ? . . S(1) Se(1) 3.4780(9) ? . . S(1) S(2) 3.2206(13) ? . . S(1) C(2) 2.649(3) ? . . S(1) C(9) 3.396(3) ? . . S(1) C(10) 2.882(3) ? . . S(1) C(11) 3.136(3) ? . . S(1) C(12) 3.422(3) ? . . S(2) Se(1) 3.4057(9) ? . . S(2) S(1) 3.2206(13) ? . . S(2) C(1) 3.391(3) ? . . S(2) C(8) 2.636(3) ? . . S(2) C(10) 2.877(3) ? . . S(2) C(11) 3.148(3) ? . . S(2) C(16) 3.360(3) ? . . P(1) C(1) 2.991(3) ? . . P(1) C(9) 2.986(3) ? . . P(1) C(10) 3.291(3) ? . . P(1) C(12) 2.762(3) ? . . P(1) C(16) 2.793(3) ? . . C(1) S(2) 3.391(3) ? . . C(1) P(1) 2.991(3) ? . . C(1) C(3) 2.422(5) ? . . C(1) C(4) 2.790(5) ? . . C(1) C(5) 2.439(4) ? . . C(1) C(9) 2.582(4) ? . . C(1) C(11) 3.393(4) ? . . C(2) S(1) 2.649(3) ? . . C(2) C(4) 2.378(5) ? . . C(2) C(5) 2.781(5) ? . . C(2) C(10) 2.448(5) ? . . C(3) C(1) 2.422(5) ? . . C(3) C(5) 2.416(5) ? . . C(3) C(6) 3.566(5) ? . 3_776 C(3) C(10) 2.848(5) ? . . C(4) C(1) 2.790(5) ? . . C(4) C(2) 2.378(5) ? . . C(4) C(5) 3.551(4) ? . 3_776 C(4) C(6) 2.435(5) ? . . C(4) C(10) 2.481(5) ? . . C(5) C(1) 2.439(4) ? . . C(5) C(2) 2.781(5) ? . . C(5) C(3) 2.416(5) ? . . C(5) C(4) 3.551(4) ? . 3_776 C(5) C(7) 2.412(5) ? . . C(5) C(8) 2.777(5) ? . . C(5) C(9) 2.435(4) ? . . C(5) C(9) 3.573(4) ? . 3_676 C(6) C(3) 3.566(5) ? . 3_776 C(6) C(4) 2.435(5) ? . . C(6) C(8) 2.391(5) ? . . C(6) C(9) 2.795(5) ? . . C(6) C(10) 2.484(4) ? . . C(7) C(5) 2.412(5) ? . . C(7) C(9) 2.419(5) ? . . C(7) C(10) 2.851(5) ? . . C(8) S(2) 2.636(3) ? . . C(8) C(5) 2.777(5) ? . . C(8) C(6) 2.391(5) ? . . C(8) C(10) 2.450(4) ? . . C(8) C(10) 3.569(4) ? . 3_676 C(9) S(1) 3.396(3) ? . . C(9) P(1) 2.986(3) ? . . C(9) C(1) 2.582(4) ? . . C(9) C(5) 2.435(4) ? . . C(9) C(5) 3.573(4) ? . 3_676 C(9) C(6) 2.795(5) ? . . C(9) C(7) 2.419(5) ? . . C(9) C(11) 3.410(4) ? . . C(9) C(16) 3.482(4) ? . . C(10) S(1) 2.882(3) ? . . C(10) S(2) 2.877(3) ? . . C(10) P(1) 3.291(3) ? . . C(10) C(2) 2.448(5) ? . . C(10) C(3) 2.848(5) ? . . C(10) C(4) 2.481(5) ? . . C(10) C(6) 2.484(4) ? . . C(10) C(7) 2.851(5) ? . . C(10) C(8) 2.450(4) ? . . C(10) C(8) 3.569(4) ? . 3_676 C(10) C(11) 3.542(4) ? . . C(11) Se(1) 3.294(3) ? . . C(11) S(1) 3.136(3) ? . . C(11) S(2) 3.148(3) ? . . C(11) C(1) 3.393(4) ? . . C(11) C(9) 3.410(4) ? . . C(11) C(10) 3.542(4) ? . . C(11) C(13) 2.410(4) ? . . C(11) C(14) 2.766(4) ? . . C(11) C(15) 2.407(4) ? . . C(12) S(1) 3.422(3) ? . . C(12) P(1) 2.762(3) ? . . C(12) C(14) 2.401(5) ? . . C(12) C(15) 2.782(5) ? . . C(12) C(16) 2.413(5) ? . . C(13) C(11) 2.410(4) ? . . C(13) C(15) 2.395(5) ? . . C(13) C(16) 2.779(5) ? . . C(14) C(11) 2.766(4) ? . . C(14) C(12) 2.401(5) ? . . C(14) C(16) 2.398(5) ? . . C(15) C(11) 2.407(4) ? . . C(15) C(12) 2.782(5) ? . . C(15) C(13) 2.395(5) ? . . C(16) S(2) 3.360(3) ? . . C(16) P(1) 2.793(3) ? . . C(16) C(9) 3.482(4) ? . . C(16) C(12) 2.413(5) ? . . C(16) C(13) 2.779(5) ? . . C(16) C(14) 2.398(5) ? . . Se(1) H(5) 2.980 ? . 1_545 Se(1) H(6) 3.222 ? . 2_646 Se(1) H(8) 3.058 ? . 1_455 Se(1) H(9) 3.558 ? . 1_455 Se(1) H(9) 3.278 ? . 2_746 Se(1) H(10) 3.362 ? . 2_746 S(1) H(1) 2.665 ? . . S(1) H(5) 3.436 ? . 3_676 S(1) H(7) 3.018 ? . . S(2) H(6) 2.651 ? . . S(2) H(9) 3.038 ? . 1_455 S(2) H(11) 2.873 ? . . P(1) H(7) 2.847 ? . . P(1) H(11) 2.897 ? . . C(1) H(1) 2.020 ? . . C(1) H(2) 3.273 ? . . C(1) H(7) 3.590 ? . . C(2) H(2) 2.046 ? . . C(2) H(3) 3.236 ? . . C(2) H(4) 3.587 ? . 3_776 C(3) H(1) 2.037 ? . . C(3) H(3) 1.999 ? . . C(4) H(1) 3.228 ? . . C(4) H(2) 2.005 ? . . C(4) H(4) 2.597 ? . . C(5) H(2) 3.276 ? . . C(5) H(3) 2.062 ? . . C(5) H(3) 3.590 ? . 3_776 C(5) H(4) 2.056 ? . . C(5) H(5) 3.272 ? . . C(6) H(3) 2.595 ? . . C(6) H(5) 2.019 ? . . C(6) H(6) 3.242 ? . . C(7) H(4) 2.015 ? . . C(7) H(6) 2.038 ? . . C(7) H(9) 3.338 ? . 2_756 C(8) H(4) 3.251 ? . . C(8) H(5) 2.046 ? . . C(8) H(9) 3.163 ? . 2_756 C(8) H(11) 3.470 ? . . C(9) H(5) 3.270 ? . . C(9) H(6) 2.016 ? . . C(9) H(11) 3.116 ? . . C(10) H(1) 3.301 ? . . C(10) H(3) 3.335 ? . . C(10) H(4) 3.337 ? . . C(10) H(6) 3.302 ? . . C(11) H(2) 3.410 ? . 4_565 C(11) H(3) 3.319 ? . 3_776 C(11) H(7) 2.046 ? . . C(11) H(8) 3.269 ? . . C(11) H(10) 3.265 ? . . C(11) H(10) 3.414 ? . 2_746 C(11) H(11) 2.038 ? . . C(12) H(1) 3.578 ? . 3_766 C(12) H(3) 3.315 ? . 3_776 C(12) H(4) 3.463 ? . 3_776 C(12) H(8) 2.046 ? . . C(12) H(9) 3.257 ? . . C(12) H(10) 2.926 ? . 2_746 C(12) H(11) 3.271 ? . . C(13) H(1) 3.421 ? . 3_766 C(13) H(3) 3.111 ? . 3_776 C(13) H(4) 3.264 ? . 3_776 C(13) H(7) 2.049 ? . . C(13) H(9) 2.020 ? . . C(13) H(10) 3.249 ? . . C(13) H(10) 3.337 ? . 2_746 C(13) H(11) 3.401 ? . 2_746 C(14) H(2) 3.431 ? . 4_565 C(14) H(3) 2.894 ? . 3_776 C(14) H(5) 3.544 ? . 2_746 C(14) H(6) 3.335 ? . 2_746 C(14) H(7) 3.259 ? . . C(14) H(8) 2.025 ? . . C(14) H(10) 2.026 ? . . C(14) H(11) 3.255 ? . . C(15) H(2) 3.597 ? . 3_776 C(15) H(2) 2.915 ? . 4_565 C(15) H(3) 2.868 ? . 3_776 C(15) H(8) 3.249 ? . . C(15) H(9) 2.020 ? . . C(15) H(11) 2.045 ? . . C(16) H(1) 3.549 ? . 4_565 C(16) H(2) 2.889 ? . 4_565 C(16) H(3) 3.099 ? . 3_776 C(16) H(7) 3.271 ? . . C(16) H(9) 3.254 ? . . C(16) H(10) 2.045 ? . . H(1) S(1) 2.665 ? . . H(1) C(1) 2.020 ? . . H(1) C(3) 2.037 ? . . H(1) C(4) 3.228 ? . . H(1) C(10) 3.301 ? . . H(1) C(12) 3.578 ? . 3_766 H(1) C(13) 3.421 ? . 3_766 H(1) C(16) 3.549 ? . 4_564 H(1) H(2) 2.337 ? . . H(1) H(7) 3.084 ? . 3_766 H(1) H(8) 2.759 ? . 3_766 H(1) H(10) 3.366 ? . 4_564 H(1) H(11) 3.124 ? . 4_564 H(2) C(1) 3.273 ? . . H(2) C(2) 2.046 ? . . H(2) C(4) 2.005 ? . . H(2) C(5) 3.276 ? . . H(2) C(11) 3.410 ? . 4_564 H(2) C(14) 3.431 ? . 4_564 H(2) C(15) 3.597 ? . 3_776 H(2) C(15) 2.915 ? . 4_564 H(2) C(16) 2.889 ? . 4_564 H(2) H(1) 2.337 ? . . H(2) H(3) 2.296 ? . . H(2) H(10) 3.391 ? . 3_776 H(2) H(10) 3.141 ? . 4_564 H(2) H(11) 3.089 ? . 4_564 H(3) C(2) 3.236 ? . . H(3) C(3) 1.999 ? . . H(3) C(5) 2.062 ? . . H(3) C(5) 3.590 ? . 3_776 H(3) C(6) 2.595 ? . . H(3) C(10) 3.335 ? . . H(3) C(11) 3.319 ? . 3_776 H(3) C(12) 3.315 ? . 3_776 H(3) C(13) 3.111 ? . 3_776 H(3) C(14) 2.894 ? . 3_776 H(3) C(15) 2.868 ? . 3_776 H(3) C(16) 3.099 ? . 3_776 H(3) H(2) 2.296 ? . . H(3) H(4) 2.397 ? . . H(3) H(9) 3.335 ? . 3_776 H(3) H(10) 3.274 ? . 3_776 H(4) C(2) 3.587 ? . 3_776 H(4) C(4) 2.597 ? . . H(4) C(5) 2.056 ? . . H(4) C(7) 2.015 ? . . H(4) C(8) 3.251 ? . . H(4) C(10) 3.337 ? . . H(4) C(12) 3.463 ? . 3_776 H(4) C(13) 3.264 ? . 3_776 H(4) H(3) 2.397 ? . . H(4) H(5) 2.316 ? . . H(4) H(7) 3.537 ? . 3_776 H(4) H(8) 3.209 ? . 3_776 H(5) Se(1) 2.980 ? . 1_565 H(5) S(1) 3.436 ? . 3_676 H(5) C(5) 3.272 ? . . H(5) C(6) 2.019 ? . . H(5) C(8) 2.046 ? . . H(5) C(9) 3.270 ? . . H(5) C(14) 3.544 ? . 2_756 H(5) H(4) 2.316 ? . . H(5) H(6) 2.338 ? . . H(5) H(9) 2.995 ? . 2_756 H(5) H(10) 3.135 ? . 2_756 H(6) Se(1) 3.222 ? . 2_656 H(6) S(2) 2.651 ? . . H(6) C(6) 3.242 ? . . H(6) C(7) 2.038 ? . . H(6) C(9) 2.016 ? . . H(6) C(10) 3.302 ? . . H(6) C(14) 3.335 ? . 2_756 H(6) H(5) 2.338 ? . . H(6) H(9) 2.637 ? . 2_756 H(6) H(11) 3.443 ? . . H(7) S(1) 3.018 ? . . H(7) P(1) 2.847 ? . . H(7) C(1) 3.590 ? . . H(7) C(11) 2.046 ? . . H(7) C(13) 2.049 ? . . H(7) C(14) 3.259 ? . . H(7) C(16) 3.271 ? . . H(7) H(1) 3.084 ? . 3_766 H(7) H(4) 3.537 ? . 3_776 H(7) H(8) 2.354 ? . . H(7) H(10) 2.877 ? . 2_746 H(8) Se(1) 3.058 ? . 1_655 H(8) C(11) 3.269 ? . . H(8) C(12) 2.046 ? . . H(8) C(14) 2.025 ? . . H(8) C(15) 3.249 ? . . H(8) H(1) 2.759 ? . 3_766 H(8) H(4) 3.209 ? . 3_776 H(8) H(7) 2.354 ? . . H(8) H(9) 2.318 ? . . H(8) H(10) 3.541 ? . 2_746 H(8) H(11) 3.179 ? . 2_746 H(9) Se(1) 3.558 ? . 1_655 H(9) Se(1) 3.278 ? . 2_756 H(9) S(2) 3.038 ? . 1_655 H(9) C(7) 3.338 ? . 2_746 H(9) C(8) 3.163 ? . 2_746 H(9) C(12) 3.257 ? . . H(9) C(13) 2.020 ? . . H(9) C(15) 2.020 ? . . H(9) C(16) 3.254 ? . . H(9) H(3) 3.335 ? . 3_776 H(9) H(5) 2.995 ? . 2_746 H(9) H(6) 2.637 ? . 2_746 H(9) H(8) 2.318 ? . . H(9) H(10) 2.320 ? . . H(10) Se(1) 3.362 ? . 2_756 H(10) C(11) 3.265 ? . . H(10) C(11) 3.414 ? . 2_756 H(10) C(12) 2.926 ? . 2_756 H(10) C(13) 3.249 ? . . H(10) C(13) 3.337 ? . 2_756 H(10) C(14) 2.026 ? . . H(10) C(16) 2.045 ? . . H(10) H(1) 3.366 ? . 4_565 H(10) H(2) 3.391 ? . 3_776 H(10) H(2) 3.141 ? . 4_565 H(10) H(3) 3.274 ? . 3_776 H(10) H(5) 3.135 ? . 2_746 H(10) H(7) 2.877 ? . 2_756 H(10) H(8) 3.541 ? . 2_756 H(10) H(9) 2.320 ? . . H(10) H(11) 2.350 ? . . H(11) S(2) 2.873 ? . . H(11) P(1) 2.897 ? . . H(11) C(8) 3.470 ? . . H(11) C(9) 3.116 ? . . H(11) C(11) 2.038 ? . . H(11) C(12) 3.271 ? . . H(11) C(13) 3.401 ? . 2_756 H(11) C(14) 3.255 ? . . H(11) C(15) 2.045 ? . . H(11) H(1) 3.124 ? . 4_565 H(11) H(2) 3.089 ? . 4_565 H(11) H(6) 3.443 ? . . H(11) H(8) 3.179 ? . 2_756 H(11) H(10) 2.350 ? . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================