Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2001 data_3Se _database_code_CSD 154470 _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Clarke, Matthew L.' 'Cole-Hamilton, D.' 'Foster, Douglas F.' 'Rodriguez i Zubiri, Mireia' 'Slawin, A.' 'Woollins, J.' _publ_contact_author_name 'Prof J Woollins' _publ_contact_author_address ; Prof J Woollins Department of Chemistry University of St Andrews St Andrews Fife KY16 9ST UNITED KINGDOM ; _publ_contact_author_email 'jdw3@st-andrews.ac.uk' _audit_creation_method SHELXL _chemical_name_systematic ; C17 H38 N2 P2 Se2 ; _chemical_name_common - _chemical_formula_moiety 'C17 H38 N2 P2 Se2' _chemical_formula_structural 'C17 H38 N2 P2 Se2' _chemical_formula_analytical 'C17 H38 N2 P2 Se2' _chemical_formula_sum 'C17 H38 N2 P2 Se2' _chemical_formula_weight 490.35 _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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.959(3) _cell_length_b 11.700(5) _cell_length_c 14.974(7) _cell_angle_alpha 108.223(8) _cell_angle_beta 98.723(8) _cell_angle_gamma 93.164(8) _cell_volume 1137.8(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 29 _cell_measurement_theta_min 12 _cell_measurement_theta_max 168 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max .14 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .01 _exptl_crystal_density_meas - _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method - _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 3.392 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min 0.31658 _exptl_absorpt_correction_T_max 0.42224 _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 SMART _diffrn_measurement_method CCD _diffrn_standards_number - _diffrn_standards_interval_count - _diffrn_standards_interval_time - _diffrn_standards_decay_% - _diffrn_reflns_number 6629 _diffrn_reflns_av_R_equivalents 0.2600 _diffrn_reflns_av_sigmaI/netI 0.2393 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 23.39 _reflns_number_total 3281 _reflns_number_observed 1295 _reflns_observed_criterion >2sigma(I) _computing_data_collection SMART _computing_cell_refinement SMART/SAINT _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement on F^2^ for ALL reflections except for 50 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^)+(0.2276P)^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 0.0000(27) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3231 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2312 _refine_ls_R_factor_obs 0.1130 _refine_ls_wR_factor_all 0.4165 _refine_ls_wR_factor_obs 0.2636 _refine_ls_goodness_of_fit_all 0.841 _refine_ls_goodness_of_fit_obs 0.987 _refine_ls_restrained_S_all 1.013 _refine_ls_restrained_S_obs 0.987 _refine_ls_shift/esd_max -0.456 _refine_ls_shift/esd_mean 0.012 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 -0.8453(3) 0.7460(2) 0.98314(15) 0.0801(9) Uani 1 d . . P1 P -1.1451(6) 0.7314(4) 0.9239(3) 0.0436(11) Uani 1 d . . N1 N -1.2350(18) 0.5970(11) 0.8466(8) 0.045(3) Uani 1 d . . C2 C -1.1041(24) 0.5011(16) 0.8131(11) 0.060(5) Uani 1 d . . H2A H -1.1312(24) 0.4363(16) 0.8385(11) 0.072 Uiso 1 calc R . H2B H -0.9695(24) 0.5353(16) 0.8394(11) 0.072 Uiso 1 calc R . C3 C -1.1248(22) 0.4476(16) 0.7055(11) 0.056(5) Uani 1 d . . H3A H -1.0784(22) 0.5101(16) 0.6816(11) 0.067 Uiso 1 calc R . H3B H -1.0393(22) 0.3840(16) 0.6914(11) 0.067 Uiso 1 calc R . N4 N -1.3169(21) 0.3985(12) 0.6538(9) 0.053(4) Uani 1 d . . P4 P -1.3585(6) 0.2572(4) 0.5740(3) 0.0424(11) Uani 1 d . . Se4 Se -1.6452(3) 0.2213(2) 0.49287(14) 0.0735(9) Uani 1 d . . C5 C -1.4473(25) 0.4868(16) 0.6524(11) 0.063(5) Uani 1 d . . H5A H -1.5358(25) 0.4600(16) 0.5914(11) 0.075 Uiso 1 calc R . H5B H -1.3726(25) 0.5615(16) 0.6570(11) 0.075 Uiso 1 calc R . C6 C -1.5684(28) 0.5129(17) 0.7323(12) 0.082(6) Uani 1 d . . H6A H -1.6603(28) 0.4426(17) 0.7220(12) 0.098 Uiso 1 calc R . H6B H -1.6426(28) 0.5803(17) 0.7309(12) 0.098 Uiso 1 calc R . C7 C -1.4337(28) 0.5439(21) 0.8321(13) 0.085(6) Uani 1 d . . H7A H -1.4982(28) 0.5986(21) 0.8784(13) 0.102 Uiso 1 calc R . H7B H -1.4291(28) 0.4697(21) 0.8479(13) 0.102 Uiso 1 calc R . C8 C -1.2867(23) 0.7639(14) 1.0184(11) 0.049(4) Uani 1 d . . H8A H -1.4234(23) 0.7597(14) 0.9884(11) 0.058 Uiso 1 calc R . C9 C -1.2303(33) 0.8922(17) 1.0879(13) 0.087(7) Uani 1 d . . H9A H -1.2362(33) 0.9486(17) 1.0531(13) 0.131 Uiso 1 calc R . H9B H -1.0997(33) 0.8986(17) 1.1222(13) 0.131 Uiso 1 calc R . H9C H -1.3194(33) 0.9102(17) 1.1323(13) 0.131 Uiso 1 calc R . C10 C -1.2791(31) 0.6702(18) 1.0727(12) 0.079(6) Uani 1 d . . H10A H -1.3142(31) 0.5901(18) 1.0276(12) 0.119 Uiso 1 calc R . H10B H -1.3693(31) 0.6867(18) 1.1165(12) 0.119 Uiso 1 calc R . H10C H -1.1491(31) 0.6758(18) 1.1073(12) 0.119 Uiso 1 calc R . C11 C -1.1885(27) 0.8439(18) 0.8648(12) 0.066(5) Uani 1 d . . H11A H -1.1323(27) 0.9221(18) 0.9118(12) 0.079 Uiso 1 calc R . C12 C -1.0769(39) 0.8242(19) 0.7818(13) 0.100(9) Uani 1 d . . H12A H -0.9426(39) 0.8164(19) 0.8033(13) 0.150 Uiso 1 calc R . H12B H -1.0837(39) 0.8921(19) 0.7588(13) 0.150 Uiso 1 calc R . H12C H -1.1342(39) 0.7518(19) 0.7311(13) 0.150 Uiso 1 calc R . C13 C -1.4071(35) 0.8568(21) 0.8330(17) 0.100(8) Uani 1 d . . H13A H -1.4738(35) 0.8689(21) 0.8863(17) 0.150 Uiso 1 calc R . H13B H -1.4663(35) 0.7846(21) 0.7826(17) 0.150 Uiso 1 calc R . H13C H -1.4162(35) 0.9250(21) 0.8104(17) 0.150 Uiso 1 calc R . C14 C -1.3160(28) 0.1451(17) 0.6357(13) 0.067(5) Uani 1 d . . H14A H -1.3571(28) 0.0646(17) 0.5886(13) 0.080 Uiso 1 calc R . C15 C -1.4547(35) 0.1660(20) 0.7126(13) 0.090(7) Uani 1 d . . H15A H -1.5870(35) 0.1647(20) 0.6822(13) 0.135 Uiso 1 calc R . H15B H -1.4141(35) 0.2431(20) 0.7612(13) 0.135 Uiso 1 calc R . H15C H -1.4472(35) 0.1031(20) 0.7411(13) 0.135 Uiso 1 calc R . C16 C -1.1008(32) 0.1462(21) 0.6842(15) 0.088(7) Uani 1 d . . H16A H -1.0172(32) 0.1345(21) 0.6373(15) 0.133 Uiso 1 calc R . H16B H -1.0931(32) 0.0823(21) 0.7116(15) 0.133 Uiso 1 calc R . H16C H -1.0594(32) 0.2227(21) 0.7335(15) 0.133 Uiso 1 calc R . C17 C -1.1753(23) 0.2422(14) 0.4998(12) 0.050(4) Uani 1 d . . H17A H -1.0477(23) 0.2549(14) 0.5415(12) 0.061 Uiso 1 calc R . C18 C -1.1749(30) 0.3345(19) 0.4487(14) 0.085(7) Uani 1 d . . H18A H -1.1627(30) 0.4143(19) 0.4944(14) 0.128 Uiso 1 calc R . H18B H -1.2950(30) 0.3211(19) 0.4040(14) 0.128 Uiso 1 calc R . H18C H -1.0666(30) 0.3269(19) 0.4152(14) 0.128 Uiso 1 calc R . C19 C -1.1963(31) 0.1127(17) 0.4270(13) 0.083(6) Uani 1 d . . H19A H -1.1951(31) 0.0547(17) 0.4604(13) 0.124 Uiso 1 calc R . H19B H -1.0893(31) 0.1044(17) 0.3927(13) 0.124 Uiso 1 calc R . H19C H -1.3174(31) 0.0988(17) 0.3830(13) 0.124 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 0.0265(12) 0.096(2) 0.093(2) -0.0012(12) 0.0024(10) 0.0073(10) P1 0.035(3) 0.054(3) 0.043(2) 0.015(2) 0.012(2) 0.004(2) N1 0.035(9) 0.059(9) 0.028(6) 0.001(6) 0.000(6) -0.005(6) C2 0.035(11) 0.074(12) 0.059(11) 0.010(10) -0.011(8) 0.027(9) C3 0.020(9) 0.073(12) 0.064(11) 0.002(9) 0.012(8) 0.027(8) N4 0.054(10) 0.051(9) 0.051(8) 0.013(7) 0.008(7) 0.009(7) P4 0.037(3) 0.047(3) 0.045(2) 0.015(2) 0.009(2) 0.006(2) Se4 0.0310(12) 0.091(2) 0.0782(14) 0.0062(11) -0.0060(9) 0.0076(10) C5 0.052(12) 0.070(12) 0.054(10) 0.007(9) -0.006(9) 0.022(10) C6 0.047(13) 0.083(14) 0.075(13) -0.019(11) -0.018(10) 0.017(10) C7 0.043(13) 0.122(18) 0.077(13) 0.016(13) 0.013(10) -0.003(12) C8 0.031(10) 0.059(11) 0.051(9) 0.005(9) 0.015(8) 0.010(8) C9 0.102(19) 0.066(14) 0.076(14) -0.003(11) 0.027(12) -0.012(12) C10 0.091(17) 0.091(15) 0.052(11) 0.022(11) 0.015(11) -0.016(12) C11 0.054(13) 0.091(14) 0.054(10) 0.018(10) 0.033(9) -0.025(10) C12 0.166(26) 0.085(15) 0.062(12) 0.032(12) 0.052(14) -0.023(15) C13 0.102(20) 0.101(18) 0.118(18) 0.064(16) 0.016(15) 0.035(15) C14 0.064(14) 0.060(11) 0.072(12) 0.010(10) 0.023(10) 0.005(10) C15 0.105(19) 0.113(18) 0.064(12) 0.043(13) 0.026(12) -0.016(14) C16 0.085(17) 0.109(17) 0.092(14) 0.062(14) 0.004(12) 0.039(14) C17 0.037(10) 0.053(10) 0.073(11) 0.026(10) 0.030(9) 0.014(8) C18 0.064(15) 0.107(17) 0.089(14) 0.025(13) 0.046(12) 0.002(12) C19 0.089(17) 0.076(14) 0.063(12) -0.006(11) 0.016(11) 0.015(12) _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 2.115(5) . ? P1 N1 1.655(13) . ? P1 C8 1.803(14) . ? P1 C11 1.82(2) . ? N1 C7 1.44(2) . ? N1 C2 1.50(2) . ? C2 C3 1.52(2) . ? C3 N4 1.43(2) . ? N4 C5 1.41(2) . ? N4 P4 1.688(14) . ? P4 C17 1.795(14) . ? P4 C14 1.84(2) . ? P4 Se4 2.118(5) . ? C5 C6 1.53(2) . ? C6 C7 1.56(2) . ? C8 C9 1.52(2) . ? C8 C10 1.55(2) . ? C11 C12 1.53(2) . ? C11 C13 1.55(3) . ? C14 C15 1.58(2) . ? C14 C16 1.56(3) . ? C17 C18 1.51(2) . ? C17 C19 1.55(2) . ? 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 C8 107.5(7) . . ? N1 P1 C11 108.1(7) . . ? C8 P1 C11 106.3(7) . . ? N1 P1 Se1 114.8(5) . . ? C8 P1 Se1 109.4(6) . . ? C11 P1 Se1 110.3(6) . . ? C7 N1 C2 110.6(14) . . ? C7 N1 P1 124.7(12) . . ? C2 N1 P1 121.0(11) . . ? N1 C2 C3 114.8(12) . . ? N4 C3 C2 116.4(13) . . ? C3 N4 C5 113.9(13) . . ? C3 N4 P4 120.9(10) . . ? C5 N4 P4 122.3(12) . . ? N4 P4 C17 107.4(7) . . ? N4 P4 C14 110.1(7) . . ? C17 P4 C14 105.1(7) . . ? N4 P4 Se4 111.9(5) . . ? C17 P4 Se4 112.0(6) . . ? C14 P4 Se4 110.1(7) . . ? N4 C5 C6 114.4(14) . . ? C5 C6 C7 110.9(15) . . ? N1 C7 C6 120.1(15) . . ? C9 C8 C10 110.8(13) . . ? C9 C8 P1 111.6(11) . . ? C10 C8 P1 113.5(11) . . ? C12 C11 C13 111.2(17) . . ? C12 C11 P1 111.0(15) . . ? C13 C11 P1 115.3(12) . . ? C15 C14 C16 109.9(16) . . ? C15 C14 P4 107.4(13) . . ? C16 C14 P4 116.0(13) . . ? C18 C17 C19 110.2(14) . . ? C18 C17 P4 113.3(11) . . ? C19 C17 P4 111.0(12) . . ? 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 N1 C7 26.3(15) . . . . ? C11 P1 N1 C7 -88.1(14) . . . . ? Se1 P1 N1 C7 148.3(13) . . . . ? C8 P1 N1 C2 -129.8(12) . . . . ? C11 P1 N1 C2 115.8(12) . . . . ? Se1 P1 N1 C2 -7.8(13) . . . . ? C7 N1 C2 C3 74.1(19) . . . . ? P1 N1 C2 C3 -126.7(14) . . . . ? N1 C2 C3 N4 -55.1(22) . . . . ? C2 C3 N4 C5 70.1(20) . . . . ? C2 C3 N4 P4 -128.7(13) . . . . ? C3 N4 P4 C17 -47.2(14) . . . . ? C5 N4 P4 C17 112.4(14) . . . . ? C3 N4 P4 C14 66.7(14) . . . . ? C5 N4 P4 C14 -133.7(14) . . . . ? C3 N4 P4 Se4 -170.5(11) . . . . ? C5 N4 P4 Se4 -10.9(14) . . . . ? C3 N4 C5 C6 -92.7(18) . . . . ? P4 N4 C5 C6 106.3(15) . . . . ? N4 C5 C6 C7 52.7(23) . . . . ? C2 N1 C7 C6 -83.0(21) . . . . ? P1 N1 C7 C6 118.7(16) . . . . ? C5 C6 C7 N1 27.5(26) . . . . ? N1 P1 C8 C9 -173.6(12) . . . . ? C11 P1 C8 C9 -58.0(15) . . . . ? Se1 P1 C8 C9 61.1(13) . . . . ? N1 P1 C8 C10 60.3(13) . . . . ? C11 P1 C8 C10 175.8(12) . . . . ? Se1 P1 C8 C10 -65.0(12) . . . . ? N1 P1 C11 C12 -64.1(15) . . . . ? C8 P1 C11 C12 -179.3(13) . . . . ? Se1 P1 C11 C12 62.1(14) . . . . ? N1 P1 C11 C13 63.4(15) . . . . ? C8 P1 C11 C13 -51.7(16) . . . . ? Se1 P1 C11 C13 -170.3(13) . . . . ? N4 P4 C14 C15 57.2(15) . . . . ? C17 P4 C14 C15 172.5(13) . . . . ? Se4 P4 C14 C15 -66.7(13) . . . . ? N4 P4 C14 C16 -66.1(15) . . . . ? C17 P4 C14 C16 49.2(15) . . . . ? Se4 P4 C14 C16 170.0(12) . . . . ? N4 P4 C17 C18 -58.0(15) . . . . ? C14 P4 C17 C18 -175.2(13) . . . . ? Se4 P4 C17 C18 65.2(14) . . . . ? N4 P4 C17 C19 177.4(12) . . . . ? C14 P4 C17 C19 60.2(14) . . . . ? Se4 P4 C17 C19 -59.4(13) . . . . ? _refine_diff_density_max 1.363 _refine_diff_density_min -1.137 _refine_diff_density_rms 0.210