Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Dr Raymundo Cea-Olivares' _publ_contact_author_address ; Instituto de Quimica Universidad Nacional Autonoma de Mexico Circuito Exterior MEXICO CITY 04510 DF MEXICO ; _publ_contact_author_email CEA@SERVIDOR.UNAM.MX _publ_section_title ; True Square planar [M{N(SePiPr2)2-Se,Se'}2] [ M= Sn, Se] complexes. An extraordinary geometrical arrangement for well known centers [Sn(II), Se(II)]. ; loop_ _publ_author_name 'Raymundo Cea-Olivares' 'Rafael Castro-Blanco' 'Veronica Garcia-Montalvo' ; S.Hernandez-Ortega ; 'Monica Moya-Cabrera' 'Ruben A. Toscano' data_Compound_2 _database_code_depnum_ccdc_archive 'CCDC 243738' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H56 N2 P4 Se4 Sn' _chemical_formula_weight 931.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Sn Sn -0.6537 1.4246 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.377(1) _cell_length_b 14.731(4) _cell_length_c 12.008(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.59(1) _cell_angle_gamma 90.00 _cell_volume 1804(1) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 9275 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 31.72 _exptl_crystal_description Prism _exptl_crystal_colour Orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas No _exptl_crystal_density_diffrn 1.714 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 4.937 _exptl_absorpt_correction_type 'Analytical Based on face indexed numerical' _exptl_absorpt_correction_T_min 0.3323 _exptl_absorpt_correction_T_max 0.4627 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex AXS CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14485 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3166 _reflns_number_gt 2645 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625' _computing_cell_refinement 'SMART V 5.625' _computing_data_reduction 'SAINT V 6.23C' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V 6.10' _computing_publication_material 'SHELXTL V 6.10' #_solved_by 'SimonHO' _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^)+(0.1809P)^2^+1.9734P] 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 3166 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.2374 _refine_ls_wR_factor_gt 0.2295 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sn1 Sn 1.0000 0.0000 1.0000 0.0550(4) Uani 1 2 d S . . Se1 Se 1.00285(8) 0.15504(6) 0.88686(7) 0.0353(3) Uani 1 1 d . . . Se2 Se 0.74913(8) 0.02738(6) 1.00254(7) 0.0357(3) Uani 1 1 d . . . P1 P 0.87375(19) 0.11464(13) 0.72923(16) 0.0259(5) Uani 1 1 d . . . P2 P 0.68936(19) -0.00726(13) 0.82351(17) 0.0252(5) Uani 1 1 d . . . N1 N 0.7540(6) 0.0503(5) 0.7362(5) 0.0295(14) Uani 1 1 d . . . C1 C 0.9737(9) 0.0613(6) 0.6352(7) 0.0346(18) Uani 1 1 d . . . H1 H 0.9162 0.0410 0.5656 0.041 Uiso 1 1 calc R . . C2 C 1.0477(11) -0.0226(7) 0.6964(9) 0.054(3) Uani 1 1 d . . . H2A H 1.0498 -0.0705 0.6425 0.064 Uiso 1 1 calc R . . H2B H 1.0029 -0.0434 0.7548 0.064 Uiso 1 1 calc R . . H2C H 1.1357 -0.0055 0.7294 0.064 Uiso 1 1 calc R . . C3 C 1.0760(11) 0.1255(7) 0.6049(10) 0.054(3) Uani 1 1 d . . . H3A H 1.1353 0.1430 0.6726 0.064 Uiso 1 1 calc R . . H3B H 1.0336 0.1785 0.5688 0.064 Uiso 1 1 calc R . . H3C H 1.1239 0.0956 0.5543 0.064 Uiso 1 1 calc R . . C4 C 0.8097(8) 0.2196(5) 0.6564(7) 0.0324(17) Uani 1 1 d . . . H4 H 0.8841 0.2544 0.6391 0.039 Uiso 1 1 calc R . . C5 C 0.7387(11) 0.2788(6) 0.7320(9) 0.050(2) Uani 1 1 d . . . H5A H 0.6941 0.3276 0.6879 0.060 Uiso 1 1 calc R . . H5B H 0.8016 0.3032 0.7933 0.060 Uiso 1 1 calc R . . H5C H 0.6763 0.2424 0.7618 0.060 Uiso 1 1 calc R . . C6 C 0.7194(13) 0.1971(8) 0.5453(9) 0.064(3) Uani 1 1 d . . . H6A H 0.6453 0.1633 0.5603 0.076 Uiso 1 1 calc R . . H6B H 0.7661 0.1615 0.4988 0.076 Uiso 1 1 calc R . . H6C H 0.6895 0.2523 0.5064 0.076 Uiso 1 1 calc R . . C7 C 0.7259(8) -0.1277(5) 0.8098(8) 0.0356(19) Uani 1 1 d . . . H7 H 0.8196 -0.1337 0.8408 0.043 Uiso 1 1 calc R . . C8 C 0.6589(11) -0.1876(6) 0.8823(10) 0.053(3) Uani 1 1 d . . . H8A H 0.5699 -0.1979 0.8454 0.064 Uiso 1 1 calc R . . H8B H 0.6596 -0.1587 0.9541 0.064 Uiso 1 1 calc R . . H8C H 0.7042 -0.2446 0.8941 0.064 Uiso 1 1 calc R . . C9 C 0.7099(14) -0.1608(7) 0.6855(10) 0.063(3) Uani 1 1 d . . . H9A H 0.7782 -0.2034 0.6791 0.076 Uiso 1 1 calc R . . H9B H 0.7155 -0.1099 0.6368 0.076 Uiso 1 1 calc R . . H9C H 0.6261 -0.1897 0.6637 0.076 Uiso 1 1 calc R . . C10 C 0.5125(8) 0.0090(6) 0.7929(9) 0.041(2) Uani 1 1 d . . . H10 H 0.4746 -0.0347 0.8392 0.050 Uiso 1 1 calc R . . C11 C 0.4713(11) 0.1008(8) 0.8236(11) 0.061(3) Uani 1 1 d . . . H11A H 0.5033 0.1455 0.7771 0.074 Uiso 1 1 calc R . . H11B H 0.5067 0.1127 0.9019 0.074 Uiso 1 1 calc R . . H11C H 0.3774 0.1037 0.8117 0.074 Uiso 1 1 calc R . . C12 C 0.4587(13) -0.0144(12) 0.6681(12) 0.087(5) Uani 1 1 d . . . H12A H 0.3922 0.0287 0.6373 0.104 Uiso 1 1 calc R . . H12B H 0.4217 -0.0743 0.6634 0.104 Uiso 1 1 calc R . . H12C H 0.5287 -0.0121 0.6258 0.104 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 Sn1 0.0557(7) 0.0651(7) 0.0429(7) -0.0028(5) 0.0062(5) -0.0050(5) Se1 0.0419(6) 0.0342(5) 0.0269(5) 0.0010(3) -0.0012(4) -0.0114(3) Se2 0.0351(5) 0.0473(6) 0.0258(5) -0.0034(3) 0.0086(4) -0.0043(4) P1 0.0291(10) 0.0268(10) 0.0217(10) 0.0025(7) 0.0043(8) -0.0030(8) P2 0.0237(10) 0.0254(10) 0.0265(11) 0.0003(7) 0.0046(8) -0.0027(7) N1 0.029(3) 0.034(3) 0.024(3) 0.006(3) 0.003(3) -0.008(3) C1 0.041(5) 0.038(4) 0.026(4) 0.004(3) 0.010(3) 0.008(4) C2 0.070(7) 0.051(6) 0.047(6) 0.018(5) 0.030(5) 0.032(5) C3 0.058(6) 0.051(6) 0.059(6) 0.003(5) 0.030(5) 0.001(5) C4 0.043(4) 0.026(4) 0.029(4) 0.004(3) 0.010(3) 0.000(3) C5 0.060(6) 0.034(5) 0.058(6) -0.002(4) 0.014(5) 0.006(4) C6 0.089(9) 0.057(7) 0.038(6) 0.012(5) -0.008(5) 0.017(6) C7 0.032(4) 0.028(4) 0.046(5) -0.009(4) 0.004(4) 0.001(3) C8 0.054(6) 0.029(4) 0.077(7) 0.000(5) 0.012(5) -0.007(4) C9 0.086(9) 0.040(5) 0.067(8) -0.014(5) 0.023(6) 0.007(5) C10 0.021(4) 0.042(5) 0.060(6) 0.003(4) 0.003(4) -0.006(4) C11 0.041(5) 0.059(7) 0.085(8) 0.003(6) 0.014(5) 0.014(5) C12 0.041(6) 0.138(14) 0.071(9) -0.019(8) -0.019(6) 0.017(7) _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 Sn1 Se2 2.6401(8) 3_757 ? Sn1 Se2 2.6401(8) . ? Sn1 Se1 2.6604(8) 3_757 ? Sn1 Se1 2.6604(8) . ? Se1 P1 2.191(2) . ? Se2 P2 2.186(2) . ? P1 N1 1.577(7) . ? P1 C4 1.840(8) . ? P1 C1 1.844(8) . ? P2 N1 1.589(6) . ? P2 C10 1.820(9) . ? P2 C7 1.828(8) . ? C1 C3 1.514(13) . ? C1 C2 1.565(12) . ? C4 C6 1.520(13) . ? C4 C5 1.539(12) . ? C7 C8 1.498(13) . ? C7 C9 1.550(14) . ? C10 C11 1.485(14) . ? C10 C12 1.539(16) . ? 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 Se2 Sn1 Se2 180.0 3_757 . ? Se2 Sn1 Se1 88.75(3) 3_757 3_757 ? Se2 Sn1 Se1 91.25(3) . 3_757 ? Se2 Sn1 Se1 91.25(3) 3_757 . ? Se2 Sn1 Se1 88.75(3) . . ? Se1 Sn1 Se1 180.000(1) 3_757 . ? P1 Se1 Sn1 98.37(6) . . ? P2 Se2 Sn1 93.16(6) . . ? N1 P1 C4 108.1(4) . . ? N1 P1 C1 108.3(4) . . ? C4 P1 C1 105.2(4) . . ? N1 P1 Se1 118.7(3) . . ? C4 P1 Se1 107.0(3) . . ? C1 P1 Se1 108.7(3) . . ? N1 P2 C10 109.2(4) . . ? N1 P2 C7 109.8(4) . . ? C10 P2 C7 109.1(4) . . ? N1 P2 Se2 116.5(3) . . ? C10 P2 Se2 105.1(3) . . ? C7 P2 Se2 106.8(3) . . ? P1 N1 P2 142.0(4) . . ? C3 C1 C2 107.5(8) . . ? C3 C1 P1 112.3(6) . . ? C2 C1 P1 109.4(6) . . ? C6 C4 C5 110.9(8) . . ? C6 C4 P1 110.1(6) . . ? C5 C4 P1 111.5(6) . . ? C8 C7 C9 113.3(8) . . ? C8 C7 P2 113.2(6) . . ? C9 C7 P2 113.9(7) . . ? C11 C10 C12 112.1(10) . . ? C11 C10 P2 113.3(7) . . ? C12 C10 P2 109.8(8) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.334 _refine_diff_density_min -3.720 _refine_diff_density_rms 0.286 data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 257445' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,2,4,4,8,8,10,10-Octaisopropyl-3,9-diaza-2,4,8,10-tetraphospha- 1,5,6,7,11-pentaselenaspiro(5.5)undeca-2,8-diene ; _chemical_name_common ; bis(N-(Diisopropylphosphanylselenoyl)-P,P-diisophenylphosphanyl selenoic amidato-Se,Se')selenium(ii) ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H56 N2 P4 Se5' _chemical_formula_weight 891.39 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.375(1) _cell_length_b 14.725(1) _cell_length_c 11.997(1) _cell_angle_alpha 90.00 _cell_angle_beta 100.57(1) _cell_angle_gamma 90.00 _cell_volume 1802(1) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6145 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 30.92 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_min 0.158 _exptl_crystal_size_mid 0.186 _exptl_crystal_size_max 0.198 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.643 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 5.277 _exptl_absorpt_correction_type 'analytical: face-indexed' _exptl_absorpt_correction_T_min 0.3979 _exptl_absorpt_correction_T_max 0.5038 _exptl_absorpt_process_details ? _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_type 'Bruker Smart Apex CCD diffractometer' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 0.661 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 24659 _diffrn_reflns_av_R_equivalents 0.0569 _diffrn_reflns_av_sigmaI/netI 0.0914 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 32.52 _reflns_number_total 6513 _reflns_number_gt 3233 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V 5.625 (Bruker, 1999)' _computing_cell_refinement 'SMART V 5.625 (Bruker, 1999)' _computing_data_reduction 'SAINT V 6.23C (Bruker, 1999)' _computing_structure_solution 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_structure_refinement 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_molecular_graphics 'SHELXTL V 6.12 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V 6.12 (Sheldrick, 2000)' _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^)+(0.0017P)^2^] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6513 _refine_ls_number_parameters 168 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0915 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0483 _refine_ls_wR_factor_gt 0.0439 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _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 0.5000 0.0000 0.5000 0.03983(10) Uani 1 2 d S . . Se2 Se 0.49715(3) 0.155012(18) 0.61319(2) 0.04488(8) Uani 1 1 d . . . Se3 Se 0.75095(3) 0.02732(2) 0.49757(2) 0.04562(8) Uani 1 1 d . . . P1 P 0.62590(7) 0.11464(5) 0.77083(5) 0.03451(17) Uani 1 1 d . . . P2 P 0.81018(6) -0.00738(4) 0.67636(5) 0.03423(17) Uani 1 1 d . . . N1 N 0.74522(19) 0.04926(13) 0.76374(16) 0.0378(5) Uani 1 1 d . . . C1 C 0.5250(2) 0.06097(17) 0.8624(2) 0.0399(7) Uani 1 1 d . . . H1 H 0.5840 0.0429 0.9323 0.048 Uiso 1 1 calc R . . C2 C 0.4245(3) 0.12574(19) 0.8958(2) 0.0611(9) Uani 1 1 d . . . H2A H 0.3724 0.1513 0.8288 0.073 Uiso 1 1 calc R . . H2B H 0.4689 0.1735 0.9421 0.073 Uiso 1 1 calc R . . H2C H 0.3689 0.0933 0.9377 0.073 Uiso 1 1 calc R . . C3 C 0.4600(3) -0.02465(17) 0.8093(2) 0.0559(8) Uani 1 1 d . . . H3A H 0.4139 -0.0538 0.8619 0.067 Uiso 1 1 calc R . . H3B H 0.5255 -0.0651 0.7909 0.067 Uiso 1 1 calc R . . H3C H 0.3992 -0.0093 0.7415 0.067 Uiso 1 1 calc R . . C4 C 0.6891(3) 0.21893(16) 0.8432(2) 0.0425(7) Uani 1 1 d . . . H4 H 0.6143 0.2541 0.8590 0.051 Uiso 1 1 calc R . . C5 C 0.7773(3) 0.19713(19) 0.9558(2) 0.0695(10) Uani 1 1 d . . . H5A H 0.8506 0.1617 0.9425 0.083 Uiso 1 1 calc R . . H5B H 0.7286 0.1633 1.0025 0.083 Uiso 1 1 calc R . . H5C H 0.8082 0.2526 0.9934 0.083 Uiso 1 1 calc R . . C6 C 0.7608(3) 0.27649(17) 0.7698(2) 0.0568(8) Uani 1 1 d . . . H6A H 0.7948 0.3299 0.8109 0.068 Uiso 1 1 calc R . . H6B H 0.7013 0.2940 0.7022 0.068 Uiso 1 1 calc R . . H6C H 0.8319 0.2422 0.7497 0.068 Uiso 1 1 calc R . . C7 C 0.7724(2) -0.12787(16) 0.6906(2) 0.0433(7) Uani 1 1 d . . . H7 H 0.6786 -0.1342 0.6600 0.052 Uiso 1 1 calc R . . C8 C 0.7909(3) -0.16090(18) 0.8132(2) 0.0694(10) Uani 1 1 d . . . H8A H 0.7388 -0.2144 0.8169 0.083 Uiso 1 1 calc R . . H8B H 0.7637 -0.1142 0.8597 0.083 Uiso 1 1 calc R . . H8C H 0.8816 -0.1749 0.8401 0.083 Uiso 1 1 calc R . . C9 C 0.8422(3) -0.18872(17) 0.6170(2) 0.0624(9) Uani 1 1 d . . . H9A H 0.9351 -0.1863 0.6443 0.075 Uiso 1 1 calc R . . H9B H 0.8231 -0.1679 0.5399 0.075 Uiso 1 1 calc R . . H9C H 0.8123 -0.2501 0.6207 0.075 Uiso 1 1 calc R . . C10 C 0.9874(2) 0.00822(18) 0.7087(2) 0.0460(7) Uani 1 1 d . . . H10 H 1.0259 -0.0349 0.6619 0.055 Uiso 1 1 calc R . . C11 C 1.0464(3) -0.0115(2) 0.8312(3) 0.0944(12) Uani 1 1 d . . . H11A H 1.1388 0.0006 0.8439 0.113 Uiso 1 1 calc R . . H11B H 1.0320 -0.0741 0.8476 0.113 Uiso 1 1 calc R . . H11C H 1.0056 0.0265 0.8797 0.113 Uiso 1 1 calc R . . C12 C 1.0264(3) 0.10244(19) 0.6775(2) 0.0669(9) Uani 1 1 d . . . H12A H 0.9935 0.1464 0.7244 0.080 Uiso 1 1 calc R . . H12B H 0.9902 0.1142 0.5993 0.080 Uiso 1 1 calc R . . H12C H 1.1202 0.1066 0.6890 0.080 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 0.0402(2) 0.0485(3) 0.0295(2) 0.00262(18) 0.00312(17) 0.0050(2) Se2 0.05147(18) 0.04443(18) 0.03560(16) -0.00144(13) -0.00031(13) 0.01265(15) Se3 0.04439(17) 0.0585(2) 0.03530(16) 0.00353(14) 0.01092(13) 0.00427(15) P1 0.0373(4) 0.0362(4) 0.0300(4) -0.0027(3) 0.0060(3) 0.0017(3) P2 0.0328(4) 0.0344(4) 0.0350(4) 0.0002(3) 0.0051(3) 0.0034(3) N1 0.0395(13) 0.0437(14) 0.0297(12) -0.0016(10) 0.0046(10) 0.0084(11) C1 0.0434(17) 0.0480(18) 0.0290(15) 0.0031(13) 0.0089(13) 0.0000(14) C2 0.057(2) 0.071(2) 0.062(2) -0.0028(17) 0.0306(17) 0.0036(17) C3 0.061(2) 0.064(2) 0.0468(19) -0.0019(16) 0.0192(15) -0.0172(17) C4 0.0493(18) 0.0375(17) 0.0415(18) -0.0088(13) 0.0102(14) 0.0003(14) C5 0.093(3) 0.059(2) 0.048(2) -0.0068(16) -0.0086(18) -0.0167(19) C6 0.070(2) 0.0418(19) 0.059(2) -0.0085(15) 0.0136(17) -0.0077(16) C7 0.0385(17) 0.0354(17) 0.0573(19) 0.0011(14) 0.0118(14) 0.0010(13) C8 0.090(3) 0.047(2) 0.071(2) 0.0246(17) 0.0168(19) 0.0027(18) C9 0.066(2) 0.0379(18) 0.084(2) -0.0071(16) 0.0158(18) -0.0007(16) C10 0.0355(16) 0.0468(19) 0.0554(19) -0.0039(15) 0.0074(14) 0.0029(14) C11 0.048(2) 0.140(4) 0.085(3) 0.022(2) -0.0148(19) -0.006(2) C12 0.048(2) 0.058(2) 0.096(3) -0.0131(19) 0.0142(18) -0.0084(16) _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 Se3 2.6399(4) 3_656 ? Se1 Se3 2.6399(4) . ? Se1 Se2 2.6589(3) 3_656 ? Se1 Se2 2.6589(3) . ? Se2 P1 2.1881(7) . ? Se3 P2 2.1809(7) . ? P1 N1 1.5827(19) . ? P1 C1 1.830(2) . ? P1 C4 1.826(2) . ? P2 N1 1.5836(19) . ? P2 C10 1.823(2) . ? P2 C7 1.832(2) . ? C1 C2 1.520(3) . ? C1 C3 1.514(3) . ? C4 C6 1.513(3) . ? C4 C5 1.520(3) . ? C7 C8 1.528(3) . ? C7 C9 1.530(3) . ? C10 C12 1.511(3) . ? C10 C11 1.512(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Se3 Se1 Se3 180.0 3_656 . ? Se3 Se1 Se2 88.751(9) 3_656 3_656 ? Se3 Se1 Se2 91.249(9) . 3_656 ? Se3 Se1 Se2 91.249(9) 3_656 . ? Se3 Se1 Se2 88.751(9) . . ? Se2 Se1 Se2 180.0 3_656 . ? P1 Se2 Se1 98.39(2) . . ? P2 Se3 Se1 93.090(19) . . ? N1 P1 C1 107.98(11) . . ? N1 P1 C4 108.73(12) . . ? C1 P1 C4 105.84(11) . . ? N1 P1 Se2 118.57(7) . . ? C1 P1 Se2 108.08(9) . . ? C4 P1 Se2 106.95(9) . . ? N1 P2 C10 109.14(12) . . ? N1 P2 C7 108.91(11) . . ? C10 P2 C7 109.07(12) . . ? N1 P2 Se3 116.76(8) . . ? C10 P2 Se3 105.74(9) . . ? C7 P2 Se3 107.00(9) . . ? P1 N1 P2 142.00(13) . . ? C2 C1 C3 111.0(2) . . ? C2 C1 P1 112.51(18) . . ? C3 C1 P1 111.54(17) . . ? C6 C4 C5 110.8(2) . . ? C6 C4 P1 111.49(17) . . ? C5 C4 P1 110.49(18) . . ? C8 C7 C9 112.3(2) . . ? C8 C7 P2 114.03(18) . . ? C9 C7 P2 112.43(18) . . ? C12 C10 C11 109.8(2) . . ? C12 C10 P2 111.61(18) . . ? C11 C10 P2 113.28(19) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 32.52 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.029 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.076