# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 186/2287 data_1 _audit_creation_method SHELXL _chemical_name_systematic ; - ; _chemical_name_common - _chemical_formula_moiety 'C12 H10 P2 Se4' _chemical_formula_structural 'C12 H10 P2 Se4' _chemical_formula_analytical 'C12 H10 P2 Se4' _chemical_formula_sum 'C12 H10 P2 Se4' _chemical_formula_weight 531.98 _chemical_melting_point - _chemical_compound_source - loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.5224(4) _cell_length_b 7.3091(5) _cell_length_c 11.3341(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.213(3) _cell_angle_gamma 90.00 _cell_volume 784.22(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max .13 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .05 _exptl_crystal_density_meas - _exptl_crystal_density_diffrn 2.253 _exptl_crystal_density_method - _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 9.539 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.508038 _exptl_absorpt_correction_T_max 0.693211 _exptl_special_details ; - ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device CCD _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number - _diffrn_standards_interval_count - _diffrn_standards_interval_time - _diffrn_standards_decay_% - _diffrn_reflns_number 3278 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 23.28 _reflns_number_total 1129 _reflns_number_observed 725 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 25 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0913P)^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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0005(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1104 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_obs 0.0447 _refine_ls_wR_factor_all 0.1493 _refine_ls_wR_factor_obs 0.1132 _refine_ls_goodness_of_fit_all 0.868 _refine_ls_goodness_of_fit_obs 0.930 _refine_ls_restrained_S_all 0.996 _refine_ls_restrained_S_obs 0.930 _refine_ls_shift/esd_max 0.005 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Se1 Se -0.01554(9) -0.22823(13) 0.49570(7) 0.0416(4) Uani 1 d . . Se2 Se 0.10794(10) -0.00011(13) 0.23365(8) 0.0432(4) Uani 1 d . . P1 P -0.0338(3) 0.0072(3) 0.3635(2) 0.0370(6) Uani 1 d . . C1 C -0.2192(10) 0.0323(11) 0.3066(9) 0.040(2) Uani 1 d . . C2 C -0.2547(11) 0.0413(12) 0.1854(9) 0.047(3) Uani 1 d . . H2A H -0.1873(11) 0.0222(12) 0.1331(9) 0.056 Uiso 1 calc R . C3 C -0.3960(12) 0.0803(17) 0.1435(11) 0.072(4) Uani 1 d . . H3A H -0.4227(12) 0.0898(17) 0.0624(11) 0.086 Uiso 1 calc R . C4 C -0.4950(12) 0.1042(18) 0.2219(14) 0.075(4) Uani 1 d . . H4A H -0.5887(12) 0.1271(18) 0.1936(14) 0.090 Uiso 1 calc R . C5 C -0.4567(11) 0.0946(17) 0.3397(12) 0.065(3) Uani 1 d . . H5A H -0.5237(11) 0.1155(17) 0.3922(12) 0.078 Uiso 1 calc R . C6 C -0.3174(11) 0.0537(14) 0.3840(10) 0.057(3) Uani 1 d . . H6A H -0.2924(11) 0.0413(14) 0.4652(10) 0.068 Uiso 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 0.0603(7) 0.0434(6) 0.0202(5) -0.0006(5) 0.0008(4) -0.0048(4) Se2 0.0503(7) 0.0542(7) 0.0258(6) 0.0016(5) 0.0072(4) 0.0010(4) P1 0.045(2) 0.0470(14) 0.0189(12) 0.0004(11) 0.0009(10) -0.0028(10) C1 0.054(6) 0.036(6) 0.031(5) 0.001(4) 0.005(5) -0.005(4) C2 0.059(7) 0.050(7) 0.029(6) 0.004(4) -0.004(5) -0.003(5) C3 0.071(9) 0.089(9) 0.050(8) 0.003(7) -0.024(7) -0.024(7) C4 0.039(7) 0.087(10) 0.100(11) 0.008(8) 0.008(7) 0.004(6) C5 0.046(7) 0.089(9) 0.063(9) 0.002(7) 0.016(6) -0.001(6) C6 0.051(7) 0.080(8) 0.041(7) -0.001(5) 0.012(5) -0.005(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 P1 2.276(2) . ? Se1 P1 2.284(2) 3_556 ? Se2 P1 2.102(3) . ? P1 C1 1.822(10) . ? P1 Se1 2.284(2) 3_556 ? C1 C6 1.359(14) . ? C1 C2 1.380(14) . ? C2 C3 1.407(14) . ? C3 C4 1.37(2) . ? C4 C5 1.35(2) . ? C5 C6 1.399(14) . ? 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 P1 85.45(9) . 3_556 ? C1 P1 Se2 115.2(3) . . ? C1 P1 Se1 108.1(3) . . ? Se2 P1 Se1 115.61(11) . . ? C1 P1 Se1 107.1(3) . 3_556 ? Se2 P1 Se1 114.08(11) . 3_556 ? Se1 P1 Se1 94.55(9) . 3_556 ? C6 C1 C2 121.7(9) . . ? C6 C1 P1 119.4(7) . . ? C2 C1 P1 118.7(8) . . ? C1 C2 C3 117.9(10) . . ? C4 C3 C2 120.4(11) . . ? C3 C4 C5 120.2(10) . . ? C4 C5 C6 120.7(11) . . ? C1 C6 C5 119.0(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag P1 Se1 P1 C1 -109.7(3) 3_556 . . . ? P1 Se1 P1 Se2 119.47(15) 3_556 . . . ? P1 Se1 P1 Se1 0.0 3_556 . . 3_556 ? Se2 P1 C1 C6 -174.6(7) . . . . ? Se1 P1 C1 C6 54.4(8) . . . . ? Se1 P1 C1 C6 -46.5(8) 3_556 . . . ? Se2 P1 C1 C2 1.2(8) . . . . ? Se1 P1 C1 C2 -129.9(6) . . . . ? Se1 P1 C1 C2 129.2(6) 3_556 . . . ? C6 C1 C2 C3 2.3(13) . . . . ? P1 C1 C2 C3 -173.3(8) . . . . ? C1 C2 C3 C4 -1.4(16) . . . . ? C2 C3 C4 C5 1.5(20) . . . . ? C3 C4 C5 C6 -2.4(20) . . . . ? C2 C1 C6 C5 -3.1(15) . . . . ? P1 C1 C6 C5 172.5(8) . . . . ? C4 C5 C6 C1 3.2(18) . . . . ? _refine_diff_density_max 0.899 _refine_diff_density_min -0.528 _refine_diff_density_rms 0.137 data_2 _audit_creation_method SHELXL _chemical_name_systematic ; - ; _chemical_name_common - _chemical_formula_moiety 'C13 H15 P Se3' _chemical_formula_structural 'C13 H15 P Se3' _chemical_formula_analytical 'C13 H15 P Se3' _chemical_formula_sum 'C13 H15 P Se3' _chemical_formula_weight 439.10 _chemical_melting_point - _chemical_compound_source - loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.3773(7) _cell_length_b 6.6669(2) _cell_length_c 12.9445(5) _cell_angle_alpha 90.00 _cell_angle_beta 101.2370(10) _cell_angle_gamma 90.00 _cell_volume 1470.91(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 41 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max .22 _exptl_crystal_size_mid .14 _exptl_crystal_size_min .1 _exptl_crystal_density_meas - _exptl_crystal_density_diffrn 1.983 _exptl_crystal_density_method - _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 7.587 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.404953 _exptl_absorpt_correction_T_max 0.693218 _exptl_special_details ; - ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device CCD _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number - _diffrn_standards_interval_count - _diffrn_standards_interval_time - _diffrn_standards_decay_% - _diffrn_reflns_number 5984 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 23.21 _reflns_number_total 2106 _reflns_number_observed 1495 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 49 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0515P)^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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0041(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2057 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_obs 0.0364 _refine_ls_wR_factor_all 0.0961 _refine_ls_wR_factor_obs 0.0761 _refine_ls_goodness_of_fit_all 0.888 _refine_ls_goodness_of_fit_obs 0.942 _refine_ls_restrained_S_all 0.998 _refine_ls_restrained_S_obs 0.942 _refine_ls_shift/esd_max -0.005 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P -0.23172(10) 0.0498(2) 0.35965(12) 0.0376(4) Uani 1 d . . Se1 Se -0.22852(4) -0.09008(9) 0.51713(5) 0.0482(2) Uani 1 d . . Se2 Se -0.22791(4) 0.23140(10) 0.59204(5) 0.0491(2) Uani 1 d . . Se3 Se -0.26324(5) -0.16644(11) 0.23905(5) 0.0594(3) Uani 1 d . . C1 C -0.3010(3) 0.2588(8) 0.3608(5) 0.0366(15) Uani 1 d . . H1A H -0.2891(3) 0.3614(8) 0.3120(5) 0.044 Uiso 1 calc R . C2 C -0.2982(3) 0.3612(9) 0.4693(4) 0.0382(15) Uani 1 d . . H2A H -0.2803(3) 0.4996(9) 0.4642(4) 0.046 Uiso 1 calc R . C3 C -0.3844(4) 0.3678(11) 0.4787(6) 0.062(2) Uani 1 d . . H3A H -0.3935(4) 0.3920(11) 0.5500(6) 0.075 Uiso 1 calc R . C4 C -0.4264(4) 0.5173(12) 0.3938(6) 0.066(2) Uani 1 d . . H4A H -0.3956(4) 0.6383(12) 0.3923(6) 0.080 Uiso 1 calc R . H4B H -0.4779(4) 0.5532(12) 0.4062(6) 0.080 Uiso 1 calc R . C5 C -0.4324(4) 0.3944(11) 0.2898(6) 0.061(2) Uani 1 d . . H5A H -0.4867(4) 0.3668(11) 0.2581(6) 0.074 Uiso 1 calc R . H5B H -0.4078(4) 0.4651(11) 0.2394(6) 0.074 Uiso 1 calc R . C6 C -0.3887(4) 0.2029(10) 0.3266(5) 0.053(2) Uani 1 d . . H6A H -0.3989(4) 0.0919(10) 0.2762(5) 0.064 Uiso 1 calc R . C7 C -0.4148(4) 0.1640(11) 0.4304(6) 0.060(2) Uani 1 d . . H7A H -0.3883(4) 0.0504(11) 0.4685(6) 0.072 Uiso 1 calc R . H7B H -0.4712(4) 0.1496(11) 0.4222(6) 0.072 Uiso 1 calc R . C8 C -0.1363(4) 0.1603(9) 0.3634(4) 0.041(2) Uani 1 d . . C9 C -0.1205(4) 0.3597(10) 0.3690(6) 0.068(2) Uani 1 d . . H9A H -0.1608(4) 0.4501(10) 0.3718(6) 0.081 Uiso 1 calc R . C10 C -0.0453(5) 0.4311(13) 0.3706(8) 0.095(3) Uani 1 d . . H10A H -0.0359(5) 0.5685(13) 0.3708(8) 0.114 Uiso 1 calc R . C11 C 0.0156(5) 0.2980(16) 0.3717(6) 0.073(2) Uani 1 d . . H11A H 0.0664(5) 0.3453(16) 0.3758(6) 0.088 Uiso 1 calc R . C12 C 0.0013(5) 0.0998(15) 0.3669(7) 0.080(3) Uani 1 d . . H12A H 0.0422(5) 0.0096(15) 0.3669(7) 0.096 Uiso 1 calc R . C13 C -0.0738(4) 0.0308(12) 0.3620(6) 0.074(2) Uani 1 d . . H13A H -0.0832(4) -0.1066(12) 0.3576(6) 0.089 Uiso 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 P1 0.0493(11) 0.0308(9) 0.0332(9) 0.0000(7) 0.0092(7) 0.0042(8) Se1 0.0654(5) 0.0386(4) 0.0414(4) 0.0090(3) 0.0123(3) 0.0027(3) Se2 0.0565(5) 0.0552(5) 0.0342(4) -0.0083(3) 0.0057(3) 0.0002(3) Se3 0.0866(6) 0.0436(4) 0.0467(4) -0.0157(3) 0.0098(4) 0.0038(4) C1 0.040(4) 0.031(3) 0.036(3) 0.001(3) 0.000(3) 0.002(3) C2 0.043(4) 0.034(4) 0.039(3) -0.003(3) 0.012(3) 0.002(3) C3 0.055(5) 0.083(6) 0.053(4) -0.014(4) 0.018(4) 0.015(4) C4 0.048(5) 0.062(5) 0.091(6) -0.006(5) 0.017(4) 0.024(4) C5 0.037(4) 0.071(5) 0.072(5) -0.002(4) -0.001(4) 0.009(4) C6 0.045(4) 0.052(4) 0.056(4) -0.009(4) -0.007(3) 0.001(3) C7 0.034(4) 0.064(5) 0.085(6) 0.004(4) 0.021(4) -0.005(4) C8 0.049(4) 0.038(4) 0.038(4) 0.009(3) 0.013(3) 0.015(3) C9 0.051(5) 0.041(5) 0.114(7) 0.009(4) 0.023(4) 0.009(4) C10 0.051(6) 0.065(6) 0.171(10) 0.033(6) 0.027(6) -0.002(5) C11 0.040(5) 0.103(7) 0.078(6) 0.016(5) 0.014(4) 0.010(5) C12 0.047(5) 0.099(8) 0.096(7) -0.003(6) 0.020(4) 0.017(5) C13 0.046(5) 0.054(5) 0.119(7) 0.001(5) 0.011(4) 0.008(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 P1 C8 1.806(7) . ? P1 C1 1.843(6) . ? P1 Se3 2.117(2) . ? P1 Se1 2.232(2) . ? Se1 Se2 2.3516(10) . ? Se2 C2 2.002(6) . ? C1 C6 1.547(8) . ? C1 C2 1.554(8) . ? C2 C3 1.526(9) . ? C3 C7 1.545(9) . ? C3 C4 1.555(10) . ? C4 C5 1.562(9) . ? C5 C6 1.514(9) . ? C6 C7 1.522(10) . ? C8 C9 1.357(9) . ? C8 C13 1.390(9) . ? C9 C10 1.388(10) . ? C10 C11 1.378(11) . ? C11 C12 1.344(11) . ? C12 C13 1.374(11) . ? 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 C8 P1 C1 106.8(3) . . ? C8 P1 Se3 113.7(2) . . ? C1 P1 Se3 116.4(2) . . ? C8 P1 Se1 106.7(2) . . ? C1 P1 Se1 102.0(2) . . ? Se3 P1 Se1 110.22(7) . . ? P1 Se1 Se2 89.60(5) . . ? C2 Se2 Se1 96.5(2) . . ? C6 C1 C2 102.7(5) . . ? C6 C1 P1 115.1(4) . . ? C2 C1 P1 115.7(4) . . ? C3 C2 C1 103.1(5) . . ? C3 C2 Se2 114.0(4) . . ? C1 C2 Se2 115.7(4) . . ? C7 C3 C2 101.9(5) . . ? C7 C3 C4 101.6(6) . . ? C2 C3 C4 107.2(6) . . ? C3 C4 C5 102.4(5) . . ? C6 C5 C4 103.1(5) . . ? C5 C6 C7 101.7(6) . . ? C5 C6 C1 107.0(5) . . ? C7 C6 C1 103.6(5) . . ? C6 C7 C3 94.0(5) . . ? C9 C8 C13 117.3(6) . . ? C9 C8 P1 125.2(5) . . ? C13 C8 P1 117.5(5) . . ? C8 C9 C10 121.2(7) . . ? C9 C10 C11 119.9(8) . . ? C12 C11 C10 119.9(8) . . ? C11 C12 C13 119.7(8) . . ? C12 C13 C8 122.0(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 P1 Se1 Se2 71.1(2) . . . . ? C1 P1 Se1 Se2 -40.8(2) . . . . ? Se3 P1 Se1 Se2 -165.10(7) . . . . ? P1 Se1 Se2 C2 35.7(2) . . . . ? C8 P1 C1 C6 163.4(5) . . . . ? Se3 P1 C1 C6 35.2(5) . . . . ? Se1 P1 C1 C6 -84.8(5) . . . . ? C8 P1 C1 C2 -76.9(5) . . . . ? Se3 P1 C1 C2 154.9(4) . . . . ? Se1 P1 C1 C2 34.8(5) . . . . ? C6 C1 C2 C3 -4.9(6) . . . . ? P1 C1 C2 C3 -131.1(5) . . . . ? C6 C1 C2 Se2 120.2(4) . . . . ? P1 C1 C2 Se2 -6.0(6) . . . . ? Se1 Se2 C2 C3 95.5(4) . . . . ? Se1 Se2 C2 C1 -23.8(4) . . . . ? C1 C2 C3 C7 38.4(6) . . . . ? Se2 C2 C3 C7 -87.8(5) . . . . ? C1 C2 C3 C4 -67.8(6) . . . . ? Se2 C2 C3 C4 165.9(4) . . . . ? C7 C3 C4 C5 -31.7(7) . . . . ? C2 C3 C4 C5 74.8(7) . . . . ? C3 C4 C5 C6 -4.2(7) . . . . ? C4 C5 C6 C7 39.5(7) . . . . ? C4 C5 C6 C1 -68.8(7) . . . . ? C2 C1 C6 C5 76.0(6) . . . . ? P1 C1 C6 C5 -157.3(5) . . . . ? C2 C1 C6 C7 -31.0(6) . . . . ? P1 C1 C6 C7 95.6(6) . . . . ? C5 C6 C7 C3 -58.0(6) . . . . ? C1 C6 C7 C3 53.0(6) . . . . ? C2 C3 C7 C6 -56.0(6) . . . . ? C4 C3 C7 C6 54.5(6) . . . . ? C1 P1 C8 C9 1.7(7) . . . . ? Se3 P1 C8 C9 131.5(6) . . . . ? Se1 P1 C8 C9 -106.8(6) . . . . ? C1 P1 C8 C13 -179.3(5) . . . . ? Se3 P1 C8 C13 -49.5(6) . . . . ? Se1 P1 C8 C13 72.1(5) . . . . ? C13 C8 C9 C10 1.6(11) . . . . ? P1 C8 C9 C10 -179.4(6) . . . . ? C8 C9 C10 C11 -3.2(14) . . . . ? C9 C10 C11 C12 2.7(14) . . . . ? C10 C11 C12 C13 -0.7(14) . . . . ? C11 C12 C13 C8 -1.0(13) . . . . ? C9 C8 C13 C12 0.5(11) . . . . ? P1 C8 C13 C12 -178.5(7) . . . . ? _refine_diff_density_max 0.400 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.097 data_4 _audit_creation_method SHELXL _chemical_name_systematic ; - ; _chemical_name_common - _chemical_formula_moiety 'C18 H15 N P2 Se3' _chemical_formula_structural 'C18 H15 N P2 Se3' _chemical_formula_analytical 'C18 H15 N P2 Se3' _chemical_formula_sum 'C18 H15 N P2 Se3' _chemical_formula_weight 544.13 _chemical_melting_point - _chemical_compound_source - 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.68590(10) _cell_length_b 16.2944(3) _cell_length_c 13.35060(10) _cell_angle_alpha 90.00 _cell_angle_beta 108.4560(10) _cell_angle_gamma 90.00 _cell_volume 1998.70(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 91 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max .13 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .09 _exptl_crystal_density_meas - _exptl_crystal_density_diffrn 1.808 _exptl_crystal_density_method - _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 5.681 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.722577 _exptl_absorpt_correction_T_max 1.00000 _exptl_special_details ; - ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device CCD _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number - _diffrn_standards_interval_count - _diffrn_standards_interval_time - _diffrn_standards_decay_% - _diffrn_reflns_number 8565 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_sigmaI/netI 0.0363 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 23.27 _reflns_number_total 2870 _reflns_number_observed 2186 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0369P)^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 riding _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0001(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2870 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_obs 0.0288 _refine_ls_wR_factor_all 0.0692 _refine_ls_wR_factor_obs 0.0634 _refine_ls_goodness_of_fit_all 1.011 _refine_ls_goodness_of_fit_obs 1.075 _refine_ls_restrained_S_all 1.011 _refine_ls_restrained_S_obs 1.075 _refine_ls_shift/esd_max -0.002 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Se1 Se 1.10465(5) 0.32096(4) 0.12207(4) 0.0654(2) Uani 1 d . . P1 P 0.90847(12) 0.35916(7) 0.01715(9) 0.0405(3) Uani 1 d . . N1 N 0.7570(3) 0.3103(2) 0.0258(3) 0.0372(8) Uani 1 d . . Se12 Se 0.80450(5) 0.47859(3) 0.04384(4) 0.0518(2) Uani 1 d . . P2 P 0.63542(11) 0.38108(6) 0.03833(9) 0.0376(3) Uani 1 d . . Se2 Se 0.43651(5) 0.38308(3) -0.08243(4) 0.0529(2) Uani 1 d . . C1 C 0.9027(5) 0.3580(2) -0.1190(3) 0.0435(11) Uani 1 d . . C2 C 1.0245(5) 0.3368(2) -0.1458(4) 0.0526(12) Uani 1 d . . H2A H 1.1098(5) 0.3218(2) -0.0934(4) 0.063 Uiso 1 calc R . C3 C 1.0198(7) 0.3377(3) -0.2499(5) 0.072(2) Uani 1 d . . H3A H 1.1013(7) 0.3222(3) -0.2678(5) 0.086 Uiso 1 calc R . C4 C 0.8978(8) 0.3611(4) -0.3258(5) 0.083(2) Uani 1 d . . H4A H 0.8968(8) 0.3625(4) -0.3957(5) 0.099 Uiso 1 calc R . C5 C 0.7764(7) 0.3826(4) -0.3022(5) 0.087(2) Uani 1 d . . H5A H 0.6927(7) 0.3982(4) -0.3556(5) 0.105 Uiso 1 calc R . C6 C 0.7779(6) 0.3812(3) -0.1983(4) 0.071(2) Uani 1 d . . H6A H 0.6949(6) 0.3959(3) -0.1817(4) 0.086 Uiso 1 calc R . C7 C 0.7362(4) 0.2228(2) 0.0176(3) 0.0365(10) Uani 1 d . . C8 C 0.7952(5) 0.1745(3) 0.1057(4) 0.0519(12) Uani 1 d . . H8A H 0.8471(5) 0.1982(3) 0.1699(4) 0.062 Uiso 1 calc R . C9 C 0.7762(6) 0.0909(3) 0.0972(5) 0.071(2) Uani 1 d . . H9A H 0.8163(6) 0.0577(3) 0.1559(5) 0.085 Uiso 1 calc R . C10 C 0.6978(6) 0.0562(3) 0.0020(5) 0.073(2) Uani 1 d . . H10A H 0.6831(6) -0.0003(3) -0.0030(5) 0.088 Uiso 1 calc R . C11 C 0.6417(6) 0.1045(3) -0.0851(4) 0.069(2) Uani 1 d . . H11A H 0.5900(6) 0.0808(3) -0.1494(4) 0.083 Uiso 1 calc R . C12 C 0.6614(5) 0.1876(3) -0.0778(4) 0.0523(12) Uani 1 d . . H12A H 0.6242(5) 0.2204(3) -0.1374(4) 0.063 Uiso 1 calc R . C13 C 0.6219(4) 0.3730(2) 0.1695(3) 0.0386(10) Uani 1 d . . C14 C 0.4907(5) 0.3886(3) 0.1870(4) 0.0521(12) Uani 1 d . . H14A H 0.4084(5) 0.4016(3) 0.1308(4) 0.062 Uiso 1 calc R . C15 C 0.4829(6) 0.3846(3) 0.2884(4) 0.0632(14) Uani 1 d . . H15A H 0.3954(6) 0.3959(3) 0.3006(4) 0.076 Uiso 1 calc R . C16 C 0.6036(6) 0.3641(3) 0.3712(4) 0.0655(14) Uani 1 d . . H16A H 0.5973(6) 0.3606(3) 0.4392(4) 0.079 Uiso 1 calc R . C17 C 0.7338(6) 0.3487(3) 0.3539(4) 0.0623(14) Uani 1 d . . H17A H 0.8155(6) 0.3348(3) 0.4101(4) 0.075 Uiso 1 calc R . C18 C 0.7433(5) 0.3540(3) 0.2539(4) 0.0509(12) Uani 1 d . . H18A H 0.8320(5) 0.3448(3) 0.2428(4) 0.061 Uiso 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 0.0388(3) 0.0961(4) 0.0548(4) 0.0113(3) 0.0056(2) 0.0014(3) P1 0.0370(6) 0.0435(6) 0.0414(7) 0.0017(6) 0.0129(5) -0.0046(5) N1 0.035(2) 0.031(2) 0.047(2) 0.000(2) 0.015(2) -0.0021(14) Se12 0.0575(3) 0.0356(3) 0.0667(4) -0.0034(2) 0.0259(3) -0.0090(2) P2 0.0361(6) 0.0357(6) 0.0405(7) 0.0003(5) 0.0113(5) -0.0002(5) Se2 0.0418(3) 0.0626(3) 0.0472(3) -0.0044(2) 0.0041(2) 0.0072(2) C1 0.048(3) 0.037(2) 0.045(3) 0.003(2) 0.014(2) -0.008(2) C2 0.064(3) 0.041(3) 0.054(3) -0.006(2) 0.021(3) -0.001(2) C3 0.100(5) 0.062(3) 0.070(4) -0.006(3) 0.051(4) 0.006(3) C4 0.126(6) 0.084(4) 0.047(4) 0.005(3) 0.039(4) 0.000(4) C5 0.093(5) 0.111(5) 0.054(4) 0.017(4) 0.017(3) 0.005(4) C6 0.062(3) 0.100(4) 0.052(4) 0.013(3) 0.018(3) 0.004(3) C7 0.035(2) 0.035(2) 0.040(3) 0.002(2) 0.014(2) 0.004(2) C8 0.073(3) 0.039(3) 0.043(3) -0.002(2) 0.017(3) 0.002(2) C9 0.110(4) 0.042(3) 0.059(4) 0.009(3) 0.023(3) 0.009(3) C10 0.097(4) 0.035(3) 0.087(4) -0.002(3) 0.029(4) -0.001(3) C11 0.082(4) 0.050(3) 0.059(4) -0.018(3) 0.002(3) -0.005(3) C12 0.059(3) 0.042(3) 0.050(3) -0.001(2) 0.008(2) 0.001(2) C13 0.041(2) 0.036(2) 0.040(3) -0.006(2) 0.014(2) -0.004(2) C14 0.050(3) 0.059(3) 0.050(3) 0.005(3) 0.020(2) 0.000(2) C15 0.062(3) 0.074(4) 0.063(4) -0.006(3) 0.034(3) -0.003(3) C16 0.086(4) 0.072(3) 0.042(3) -0.010(3) 0.026(3) -0.014(3) C17 0.069(4) 0.068(3) 0.044(3) -0.007(3) 0.008(3) 0.001(3) C18 0.045(3) 0.061(3) 0.043(3) -0.004(3) 0.009(2) 0.000(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 2.0676(12) . ? P1 N1 1.705(3) . ? P1 C1 1.801(4) . ? P1 Se12 2.2705(12) . ? N1 C7 1.439(5) . ? N1 P2 1.694(3) . ? Se12 P2 2.2662(11) . ? P2 C13 1.802(4) . ? P2 Se2 2.0846(11) . ? C1 C2 1.380(6) . ? C1 C6 1.384(6) . ? C2 C3 1.376(7) . ? C3 C4 1.345(8) . ? C4 C5 1.356(8) . ? C5 C6 1.383(7) . ? C7 C12 1.376(6) . ? C7 C8 1.379(6) . ? C8 C9 1.374(6) . ? C9 C10 1.379(7) . ? C10 C11 1.366(7) . ? C11 C12 1.367(6) . ? C13 C18 1.382(6) . ? C13 C14 1.386(6) . ? C14 C15 1.381(7) . ? C15 C16 1.372(7) . ? C16 C17 1.376(7) . ? C17 C18 1.369(6) . ? 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 N1 P1 C1 108.1(2) . . ? N1 P1 Se1 116.07(12) . . ? C1 P1 Se1 114.13(15) . . ? N1 P1 Se12 87.47(11) . . ? C1 P1 Se12 107.09(14) . . ? Se1 P1 Se12 120.66(6) . . ? C7 N1 P2 126.6(3) . . ? C7 N1 P1 124.1(2) . . ? P2 N1 P1 109.2(2) . . ? P2 Se12 P1 75.28(4) . . ? N1 P2 C13 108.2(2) . . ? N1 P2 Se2 115.82(13) . . ? C13 P2 Se2 114.76(14) . . ? N1 P2 Se12 87.86(11) . . ? C13 P2 Se12 107.10(13) . . ? Se2 P2 Se12 119.71(5) . . ? C2 C1 C6 118.8(4) . . ? C2 C1 P1 120.5(4) . . ? C6 C1 P1 120.6(4) . . ? C1 C2 C3 120.0(5) . . ? C4 C3 C2 120.3(5) . . ? C3 C4 C5 121.1(5) . . ? C4 C5 C6 119.6(6) . . ? C1 C6 C5 120.1(5) . . ? C12 C7 C8 120.4(4) . . ? C12 C7 N1 120.2(4) . . ? C8 C7 N1 119.4(4) . . ? C9 C8 C7 119.1(5) . . ? C8 C9 C10 120.2(5) . . ? C11 C10 C9 120.2(5) . . ? C10 C11 C12 120.1(5) . . ? C11 C12 C7 120.0(5) . . ? C18 C13 C14 119.5(4) . . ? C18 C13 P2 120.3(3) . . ? C14 C13 P2 120.2(3) . . ? C15 C14 C13 119.6(4) . . ? C16 C15 C14 120.3(5) . . ? C15 C16 C17 120.1(5) . . ? C18 C17 C16 120.0(5) . . ? C17 C18 C13 120.5(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 P1 N1 C7 73.8(4) . . . . ? Se1 P1 N1 C7 -55.9(4) . . . . ? Se12 P1 N1 C7 -179.1(3) . . . . ? C1 P1 N1 P2 -103.2(2) . . . . ? Se1 P1 N1 P2 127.14(15) . . . . ? Se12 P1 N1 P2 4.0(2) . . . . ? N1 P1 Se12 P2 -2.92(12) . . . . ? C1 P1 Se12 P2 105.26(15) . . . . ? Se1 P1 Se12 P2 -121.95(7) . . . . ? C7 N1 P2 C13 71.9(4) . . . . ? P1 N1 P2 C13 -111.3(2) . . . . ? C7 N1 P2 Se2 -58.6(4) . . . . ? P1 N1 P2 Se2 118.2(2) . . . . ? C7 N1 P2 Se12 179.2(3) . . . . ? P1 N1 P2 Se12 -4.0(2) . . . . ? P1 Se12 P2 N1 2.94(12) . . . . ? P1 Se12 P2 C13 111.37(14) . . . . ? P1 Se12 P2 Se2 -115.77(6) . . . . ? N1 P1 C1 C2 -133.8(3) . . . . ? Se1 P1 C1 C2 -3.0(4) . . . . ? Se12 P1 C1 C2 133.2(3) . . . . ? N1 P1 C1 C6 48.6(4) . . . . ? Se1 P1 C1 C6 179.3(3) . . . . ? Se12 P1 C1 C6 -44.4(4) . . . . ? C6 C1 C2 C3 -0.9(7) . . . . ? P1 C1 C2 C3 -178.6(4) . . . . ? C1 C2 C3 C4 1.5(8) . . . . ? C2 C3 C4 C5 -1.3(9) . . . . ? C3 C4 C5 C6 0.5(10) . . . . ? C2 C1 C6 C5 0.2(7) . . . . ? P1 C1 C6 C5 177.9(4) . . . . ? C4 C5 C6 C1 0.0(9) . . . . ? P2 N1 C7 C12 81.4(5) . . . . ? P1 N1 C7 C12 -95.0(4) . . . . ? P2 N1 C7 C8 -100.3(4) . . . . ? P1 N1 C7 C8 83.3(5) . . . . ? C12 C7 C8 C9 -1.1(7) . . . . ? N1 C7 C8 C9 -179.3(4) . . . . ? C7 C8 C9 C10 -0.7(8) . . . . ? C8 C9 C10 C11 1.6(9) . . . . ? C9 C10 C11 C12 -0.9(9) . . . . ? C10 C11 C12 C7 -0.8(8) . . . . ? C8 C7 C12 C11 1.8(7) . . . . ? N1 C7 C12 C11 -179.9(4) . . . . ? N1 P2 C13 C18 35.5(4) . . . . ? Se2 P2 C13 C18 166.6(3) . . . . ? Se12 P2 C13 C18 -58.0(3) . . . . ? N1 P2 C13 C14 -146.8(3) . . . . ? Se2 P2 C13 C14 -15.8(4) . . . . ? Se12 P2 C13 C14 119.7(3) . . . . ? C18 C13 C14 C15 -0.3(6) . . . . ? P2 C13 C14 C15 -178.0(3) . . . . ? C13 C14 C15 C16 -1.0(7) . . . . ? C14 C15 C16 C17 1.1(8) . . . . ? C15 C16 C17 C18 0.1(8) . . . . ? C16 C17 C18 C13 -1.4(7) . . . . ? C14 C13 C18 C17 1.5(7) . . . . ? P2 C13 C18 C17 179.2(4) . . . . ? _refine_diff_density_max 0.486 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.063