# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'J. Woollins' _publ_contact_author_address ; Department of Chemistry University of St Andrews St Andrews FIFE SCOTLAND KY16 9ST UNITED KINGDOM ; _publ_contact_author_email JDW3@ST-ANDREWS.AC.UK _publ_section_title ; >From Phenylalkylcyanamides to Heterocyclic Selenazadiphospholaminediselenides and Carbamimidoyl(phenyl)phosphinodiselenoic Acids ; loop_ _publ_author_name J.Woollins 'Guoxiong Hua.' 'Yang Li.' A.Slawin 'Qingzhi Zhang.' # Attachment '1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 690501' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 N2 P2 Se3' _chemical_formula_sum 'C22 H22 N2 P2 Se3' _chemical_formula_weight 613.24 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 Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.865(7) _cell_length_b 10.616(3) _cell_length_c 23.670(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4741(3) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 8341 _cell_measurement_theta_min 2.0313 _cell_measurement_theta_max 27.9926 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1300 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.0500 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.718 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2400 _exptl_absorpt_coefficient_mu 4.802 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7313 _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 scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44226 _diffrn_reflns_av_R_equivalents 0.0869 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 25.48 _reflns_number_total 4367 _reflns_number_gt 3263 _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^)+(0.1016P)^2^+1.8097P] 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 4367 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0935 _refine_ls_R_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.1952 _refine_ls_wR_factor_gt 0.1792 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _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 0.43736(4) 0.46751(8) 0.91319(4) 0.0806(3) Uani 1 1 d . . . P1 P 0.52829(8) 0.57666(16) 0.90617(7) 0.0575(4) Uani 1 1 d . . . Se2 Se 0.53939(4) 0.74298(6) 0.96281(3) 0.0672(3) Uani 1 1 d . . . Se3 Se 0.56406(4) 1.03407(8) 0.89048(4) 0.0879(3) Uani 1 1 d . . . P3 P 0.50375(9) 0.87062(16) 0.89166(7) 0.0582(4) Uani 1 1 d . . . N4 N 0.5101(3) 0.7806(5) 0.8363(2) 0.0658(14) Uani 1 1 d . . . C5 C 0.5304(3) 0.6638(6) 0.8369(3) 0.0555(14) Uani 1 1 d . . . N6 N 0.5459(3) 0.6029(5) 0.7899(2) 0.0610(13) Uani 1 1 d . . . C7 C 0.5460(4) 0.6713(7) 0.7369(3) 0.076(2) Uani 1 1 d . . . H7A H 0.5003 0.7165 0.7330 0.091 Uiso 1 1 calc R . . H7B H 0.5493 0.6102 0.7054 0.091 Uiso 1 1 calc R . . C8 C 0.6067(6) 0.7667(9) 0.7314(4) 0.104(3) Uani 1 1 d . . . H8A H 0.6044 0.8052 0.6933 0.124 Uiso 1 1 calc R . . H8B H 0.5992 0.8347 0.7594 0.124 Uiso 1 1 calc R . . C9 C 0.6795(4) 0.7138(8) 0.7398(3) 0.083(2) Uani 1 1 d . . . C10 C 0.7234(7) 0.7634(9) 0.7798(4) 0.106(3) Uani 1 1 d . . . H10A H 0.7068 0.8302 0.8030 0.127 Uiso 1 1 calc R . . C11 C 0.7922(7) 0.7184(12) 0.7874(4) 0.111(3) Uani 1 1 d . . . H11A H 0.8224 0.7540 0.8153 0.134 Uiso 1 1 calc R . . C12 C 0.8149(6) 0.6221(12) 0.7540(5) 0.116(3) Uani 1 1 d . . . H12A H 0.8616 0.5899 0.7586 0.139 Uiso 1 1 calc R . . C13 C 0.7728(7) 0.5736(12) 0.7155(5) 0.131(4) Uani 1 1 d . . . H13A H 0.7890 0.5057 0.6927 0.157 Uiso 1 1 calc R . . C14 C 0.7068(6) 0.6197(11) 0.7081(4) 0.108(3) Uani 1 1 d . . . H14A H 0.6781 0.5842 0.6793 0.129 Uiso 1 1 calc R . . C15 C 0.5616(4) 0.4699(7) 0.7862(3) 0.076(2) Uani 1 1 d . . . H15A H 0.6130 0.4573 0.7882 0.113 Uiso 1 1 calc R . . H15B H 0.5437 0.4366 0.7503 0.113 Uiso 1 1 calc R . . H15C H 0.5388 0.4256 0.8176 0.113 Uiso 1 1 calc R . . C16 C 0.6107(3) 0.4935(7) 0.9147(3) 0.0595(15) Uani 1 1 d . . . C17 C 0.6117(4) 0.3762(7) 0.9379(3) 0.0743(18) Uani 1 1 d . . . H17A H 0.5687 0.3360 0.9483 0.089 Uiso 1 1 calc R . . C18 C 0.6758(6) 0.3162(8) 0.9460(4) 0.098(3) Uani 1 1 d . . . H18A H 0.6770 0.2356 0.9634 0.118 Uiso 1 1 calc R . . C19 C 0.7376(5) 0.3721(10) 0.9293(4) 0.098(3) Uani 1 1 d . . . H19A H 0.7815 0.3299 0.9343 0.117 Uiso 1 1 calc R . . C20 C 0.7357(4) 0.4878(10) 0.9056(4) 0.094(3) Uani 1 1 d . . . H20A H 0.7784 0.5258 0.8929 0.112 Uiso 1 1 calc R . . C21 C 0.6730(4) 0.5504(8) 0.8997(3) 0.078(2) Uani 1 1 d . . . H21A H 0.6726 0.6338 0.8852 0.094 Uiso 1 1 calc R . . C22 C 0.4108(3) 0.8988(7) 0.9034(3) 0.0671(18) Uani 1 1 d . . . C23 C 0.3918(5) 1.0014(11) 0.9333(4) 0.104(3) Uani 1 1 d . . . H23A H 0.4270 1.0591 0.9458 0.125 Uiso 1 1 calc R . . C24 C 0.3210(6) 1.0226(15) 0.9458(4) 0.145(5) Uani 1 1 d . . . H24A H 0.3074 1.0951 0.9667 0.174 Uiso 1 1 calc R . . C25 C 0.2715(5) 0.9394(16) 0.9281(6) 0.142(5) Uani 1 1 d . . . H25A H 0.2230 0.9532 0.9368 0.170 Uiso 1 1 calc R . . C26 C 0.2904(5) 0.8381(13) 0.8983(5) 0.124(4) Uani 1 1 d . . . H26A H 0.2553 0.7808 0.8853 0.149 Uiso 1 1 calc R . . C27 C 0.3615(4) 0.8161(9) 0.8862(4) 0.096(2) Uani 1 1 d . . . H27A H 0.3750 0.7428 0.8658 0.116 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 0.0559(5) 0.0898(6) 0.0962(6) 0.0062(4) 0.0023(4) -0.0178(4) P1 0.0482(9) 0.0585(9) 0.0658(10) 0.0009(8) 0.0020(7) -0.0042(7) Se2 0.0725(5) 0.0680(5) 0.0611(5) -0.0028(3) -0.0091(3) 0.0054(3) Se3 0.0728(6) 0.0727(6) 0.1182(8) 0.0089(4) -0.0161(4) -0.0120(4) P3 0.0521(9) 0.0604(9) 0.0622(10) -0.0021(7) -0.0031(7) 0.0049(8) N4 0.074(4) 0.062(3) 0.062(3) -0.004(2) -0.005(3) 0.014(3) C5 0.050(3) 0.065(4) 0.052(4) 0.006(3) -0.006(3) -0.011(3) N6 0.067(3) 0.056(3) 0.060(3) -0.004(2) -0.007(2) -0.001(3) C7 0.081(5) 0.086(5) 0.061(4) -0.008(4) -0.013(3) 0.013(4) C8 0.113(8) 0.100(6) 0.099(7) 0.019(5) 0.014(6) 0.016(6) C9 0.085(6) 0.099(6) 0.063(5) 0.027(4) 0.017(4) 0.009(5) C10 0.130(9) 0.096(7) 0.091(7) -0.003(5) 0.003(6) -0.006(6) C11 0.108(8) 0.128(9) 0.098(8) 0.010(6) -0.010(6) -0.032(7) C12 0.091(8) 0.127(9) 0.128(9) 0.025(7) -0.007(7) 0.008(6) C13 0.112(9) 0.132(10) 0.148(10) -0.015(8) 0.002(7) 0.021(8) C14 0.093(7) 0.128(8) 0.103(7) -0.019(6) -0.013(5) -0.013(6) C15 0.093(6) 0.060(4) 0.074(5) -0.014(3) 0.008(4) 0.001(4) C16 0.048(4) 0.067(4) 0.063(4) -0.002(3) 0.004(3) 0.000(3) C17 0.076(5) 0.065(4) 0.082(5) 0.004(4) 0.009(4) 0.005(4) C18 0.122(8) 0.079(5) 0.093(6) 0.008(4) -0.003(5) 0.044(6) C19 0.070(5) 0.116(7) 0.108(7) -0.039(6) -0.023(5) 0.034(5) C20 0.059(5) 0.095(6) 0.126(7) -0.011(5) -0.007(4) -0.002(5) C21 0.053(4) 0.082(5) 0.099(6) 0.003(4) -0.003(4) -0.005(4) C22 0.048(4) 0.090(5) 0.064(4) -0.007(4) -0.008(3) 0.012(4) C23 0.074(6) 0.143(8) 0.097(6) -0.040(6) -0.010(5) 0.013(5) C24 0.079(7) 0.262(16) 0.095(7) -0.051(8) 0.000(5) 0.070(9) C25 0.051(6) 0.225(16) 0.150(11) 0.051(10) 0.013(6) 0.035(8) C26 0.060(6) 0.166(11) 0.148(10) 0.030(8) -0.020(6) -0.010(7) C27 0.056(5) 0.101(6) 0.132(7) 0.000(5) -0.012(4) 0.005(4) _geom_special_details ; This structure is acceptable for connectivity and heavy atom positions but the light atoms are poorly determined. The C-C distances in the phenyl rings appear shorter than is normal as a consequence of the low quality of the determination. 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 2.0768(18) . ? P1 C16 1.799(7) . ? P1 C5 1.884(6) . ? P1 Se2 2.2267(19) . ? Se2 P3 2.2637(18) . ? Se3 P3 2.075(2) . ? P3 N4 1.626(5) . ? P3 C22 1.800(7) . ? N4 C5 1.298(8) . ? C5 N6 1.320(8) . ? N6 C15 1.445(9) . ? N6 C7 1.450(8) . ? C7 C8 1.535(12) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.496(12) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.351(12) . ? C9 C10 1.366(13) . ? C10 C11 1.393(16) . ? C10 H10A 0.9500 . ? C11 C12 1.362(15) . ? C11 H11A 0.9500 . ? C12 C13 1.314(15) . ? C12 H12A 0.9500 . ? C13 C14 1.351(14) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.360(9) . ? C16 C21 1.369(9) . ? C17 C18 1.380(11) . ? C17 H17A 0.9500 . ? C18 C19 1.367(13) . ? C18 H18A 0.9500 . ? C19 C20 1.351(13) . ? C19 H19A 0.9500 . ? C20 C21 1.365(11) . ? C20 H20A 0.9500 . ? C21 H21A 0.9500 . ? C22 C27 1.343(11) . ? C22 C23 1.347(11) . ? C23 C24 1.387(12) . ? C23 H23A 0.9500 . ? C24 C25 1.353(17) . ? C24 H24A 0.9500 . ? C25 C26 1.335(17) . ? C25 H25A 0.9500 . ? C26 C27 1.390(13) . ? C26 H26A 0.9500 . ? C27 H27A 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 C16 P1 C5 108.7(3) . . ? C16 P1 Se1 115.5(2) . . ? C5 P1 Se1 111.16(18) . . ? C16 P1 Se2 103.9(2) . . ? C5 P1 Se2 97.6(2) . . ? Se1 P1 Se2 118.17(8) . . ? P1 Se2 P3 89.93(7) . . ? N4 P3 C22 107.1(3) . . ? N4 P3 Se3 116.1(2) . . ? C22 P3 Se3 113.4(3) . . ? N4 P3 Se2 103.0(2) . . ? C22 P3 Se2 105.9(2) . . ? Se3 P3 Se2 110.35(8) . . ? C5 N4 P3 125.1(4) . . ? N4 C5 N6 121.7(5) . . ? N4 C5 P1 118.2(5) . . ? N6 C5 P1 119.9(5) . . ? C5 N6 C15 125.1(6) . . ? C5 N6 C7 118.9(6) . . ? C15 N6 C7 116.0(5) . . ? N6 C7 C8 113.9(6) . . ? N6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? N6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C9 C8 C7 115.2(7) . . ? C9 C8 H8A 108.5 . . ? C7 C8 H8A 108.5 . . ? C9 C8 H8B 108.5 . . ? C7 C8 H8B 108.5 . . ? H8A C8 H8B 107.5 . . ? C14 C9 C10 116.0(9) . . ? C14 C9 C8 123.6(9) . . ? C10 C9 C8 120.3(9) . . ? C9 C10 C11 121.5(10) . . ? C9 C10 H10A 119.3 . . ? C11 C10 H10A 119.3 . . ? C12 C11 C10 118.4(10) . . ? C12 C11 H11A 120.8 . . ? C10 C11 H11A 120.8 . . ? C13 C12 C11 120.4(11) . . ? C13 C12 H12A 119.8 . . ? C11 C12 H12A 119.8 . . ? C12 C13 C14 120.4(12) . . ? C12 C13 H13A 119.8 . . ? C14 C13 H13A 119.8 . . ? C13 C14 C9 123.2(10) . . ? C13 C14 H14A 118.4 . . ? C9 C14 H14A 118.4 . . ? N6 C15 H15A 109.5 . . ? N6 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N6 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 119.7(6) . . ? C17 C16 P1 120.5(5) . . ? C21 C16 P1 119.8(5) . . ? C16 C17 C18 119.4(7) . . ? C16 C17 H17A 120.3 . . ? C18 C17 H17A 120.3 . . ? C19 C18 C17 120.4(8) . . ? C19 C18 H18A 119.8 . . ? C17 C18 H18A 119.8 . . ? C20 C19 C18 119.6(8) . . ? C20 C19 H19A 120.2 . . ? C18 C19 H19A 120.2 . . ? C19 C20 C21 120.5(8) . . ? C19 C20 H20A 119.8 . . ? C21 C20 H20A 119.8 . . ? C20 C21 C16 120.2(8) . . ? C20 C21 H21A 119.9 . . ? C16 C21 H21A 119.9 . . ? C27 C22 C23 120.2(7) . . ? C27 C22 P3 121.3(6) . . ? C23 C22 P3 118.3(6) . . ? C22 C23 C24 120.0(10) . . ? C22 C23 H23A 120.0 . . ? C24 C23 H23A 120.0 . . ? C25 C24 C23 119.5(11) . . ? C25 C24 H24A 120.2 . . ? C23 C24 H24A 120.2 . . ? C26 C25 C24 120.4(10) . . ? C26 C25 H25A 119.8 . . ? C24 C25 H25A 119.8 . . ? C25 C26 C27 120.2(11) . . ? C25 C26 H26A 119.9 . . ? C27 C26 H26A 119.9 . . ? C22 C27 C26 119.7(10) . . ? C22 C27 H27A 120.1 . . ? C26 C27 H27A 120.1 . . ? 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 C16 P1 Se2 P3 130.8(2) . . . . ? C5 P1 Se2 P3 19.29(19) . . . . ? Se1 P1 Se2 P3 -99.71(9) . . . . ? P1 Se2 P3 N4 -14.3(2) . . . . ? P1 Se2 P3 C22 98.0(3) . . . . ? P1 Se2 P3 Se3 -138.94(8) . . . . ? C22 P3 N4 C5 -110.6(6) . . . . ? Se3 P3 N4 C5 121.6(5) . . . . ? Se2 P3 N4 C5 0.8(6) . . . . ? P3 N4 C5 N6 -168.2(5) . . . . ? P3 N4 C5 P1 18.0(8) . . . . ? C16 P1 C5 N4 -133.4(5) . . . . ? Se1 P1 C5 N4 98.4(5) . . . . ? Se2 P1 C5 N4 -25.8(5) . . . . ? C16 P1 C5 N6 52.7(5) . . . . ? Se1 P1 C5 N6 -75.5(5) . . . . ? Se2 P1 C5 N6 160.3(4) . . . . ? N4 C5 N6 C15 -173.2(6) . . . . ? P1 C5 N6 C15 0.5(8) . . . . ? N4 C5 N6 C7 5.2(9) . . . . ? P1 C5 N6 C7 178.9(4) . . . . ? C5 N6 C7 C8 69.4(8) . . . . ? C15 N6 C7 C8 -112.1(7) . . . . ? N6 C7 C8 C9 55.0(10) . . . . ? C7 C8 C9 C14 58.7(11) . . . . ? C7 C8 C9 C10 -123.8(9) . . . . ? C14 C9 C10 C11 -0.4(13) . . . . ? C8 C9 C10 C11 -178.1(8) . . . . ? C9 C10 C11 C12 -0.4(15) . . . . ? C10 C11 C12 C13 0.2(17) . . . . ? C11 C12 C13 C14 0.8(19) . . . . ? C12 C13 C14 C9 -1.7(19) . . . . ? C10 C9 C14 C13 1.5(15) . . . . ? C8 C9 C14 C13 179.1(10) . . . . ? C5 P1 C16 C17 -141.3(6) . . . . ? Se1 P1 C16 C17 -15.6(6) . . . . ? Se2 P1 C16 C17 115.5(6) . . . . ? C5 P1 C16 C21 41.1(6) . . . . ? Se1 P1 C16 C21 166.8(5) . . . . ? Se2 P1 C16 C21 -62.1(6) . . . . ? C21 C16 C17 C18 0.1(11) . . . . ? P1 C16 C17 C18 -177.5(6) . . . . ? C16 C17 C18 C19 -2.2(12) . . . . ? C17 C18 C19 C20 1.2(14) . . . . ? C18 C19 C20 C21 1.9(14) . . . . ? C19 C20 C21 C16 -4.0(13) . . . . ? C17 C16 C21 C20 3.0(11) . . . . ? P1 C16 C21 C20 -179.4(6) . . . . ? N4 P3 C22 C27 26.6(8) . . . . ? Se3 P3 C22 C27 156.0(6) . . . . ? Se2 P3 C22 C27 -82.8(7) . . . . ? N4 P3 C22 C23 -157.7(7) . . . . ? Se3 P3 C22 C23 -28.3(8) . . . . ? Se2 P3 C22 C23 92.8(7) . . . . ? C27 C22 C23 C24 -0.8(15) . . . . ? P3 C22 C23 C24 -176.5(9) . . . . ? C22 C23 C24 C25 0.4(18) . . . . ? C23 C24 C25 C26 -1(2) . . . . ? C24 C25 C26 C27 1.2(19) . . . . ? C23 C22 C27 C26 1.4(14) . . . . ? P3 C22 C27 C26 177.0(7) . . . . ? C25 C26 C27 C22 -1.6(16) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.412 _refine_diff_density_min -0.535 _refine_diff_density_rms 0.106 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 690502' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 N2 P2 Se3' _chemical_formula_sum 'C22 H22 N2 P2 Se3' _chemical_absolute_configuration ad _chemical_formula_weight 613.24 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 14.813(3) _cell_length_b 16.104(2) _cell_length_c 9.7349(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2322.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 8720 _cell_measurement_theta_min 1.8678 _cell_measurement_theta_max 28.7837 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.0300 _exptl_crystal_size_mid 0.0300 _exptl_crystal_size_min 0.0300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.754 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 4.901 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7530 _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 15131 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0617 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 25.36 _reflns_number_total 4249 _reflns_number_gt 3892 _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^)+(0.0228P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.009(11) _refine_ls_number_reflns 4249 _refine_ls_number_parameters 267 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0672 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.140 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 1.03487(3) 0.13201(3) -0.13845(6) 0.02528(15) Uani 1 1 d . . . P1 P 0.92898(8) 0.12804(7) 0.00223(14) 0.0158(3) Uani 1 1 d . . . Se2 Se 0.81858(3) 0.03579(3) -0.03132(6) 0.01822(13) Uani 1 1 d . . . P3 P 0.71110(7) 0.13743(7) -0.00517(14) 0.0157(3) Uani 1 1 d . . . Se3 Se 0.62360(3) 0.11888(3) 0.16099(6) 0.02126(14) Uani 1 1 d . . . N4 N 0.7704(2) 0.2240(2) -0.0028(4) 0.0151(9) Uani 1 1 d . . . C5 C 0.8569(3) 0.2254(3) -0.0093(5) 0.0165(11) Uani 1 1 d . . . N5 N 0.9059(2) 0.2941(2) -0.0252(4) 0.0133(9) Uani 1 1 d D . . H5N H 0.9715(5) 0.286(3) -0.022(7) 0.058(19) Uiso 1 1 d D . . C6 C 0.8613(3) 0.3757(3) -0.0452(5) 0.0164(11) Uani 1 1 d . . . H6A H 0.9064 0.4206 -0.0345 0.020 Uiso 1 1 calc R . . H6B H 0.8143 0.3834 0.0260 0.020 Uiso 1 1 calc R . . C7 C 0.8183(3) 0.3814(3) -0.1873(5) 0.0149(10) Uani 1 1 d . . . H7A H 0.7837 0.4338 -0.1937 0.018 Uiso 1 1 calc R . . H7B H 0.7753 0.3348 -0.1987 0.018 Uiso 1 1 calc R . . C8 C 0.8876(3) 0.3786(3) -0.3047(5) 0.0178(11) Uani 1 1 d . . . H8A H 0.9271 0.4282 -0.2991 0.021 Uiso 1 1 calc R . . H8B H 0.9261 0.3288 -0.2940 0.021 Uiso 1 1 calc R . . C9 C 0.8426(3) 0.3764(3) -0.4428(5) 0.0191(11) Uani 1 1 d . . . C10 C 0.8391(3) 0.3035(3) -0.5196(6) 0.0234(12) Uani 1 1 d . . . H10A H 0.8679 0.2550 -0.4856 0.028 Uiso 1 1 calc R . . C11 C 0.7945(3) 0.3003(3) -0.6441(6) 0.0280(13) Uani 1 1 d . . . H11A H 0.7938 0.2501 -0.6953 0.034 Uiso 1 1 calc R . . C12 C 0.7510(3) 0.3698(3) -0.6944(5) 0.0274(13) Uani 1 1 d . . . H12A H 0.7192 0.3675 -0.7791 0.033 Uiso 1 1 calc R . . C13 C 0.7541(3) 0.4426(3) -0.6203(6) 0.0299(14) Uani 1 1 d . . . H13A H 0.7253 0.4909 -0.6550 0.036 Uiso 1 1 calc R . . C14 C 0.7991(3) 0.4459(3) -0.4952(6) 0.0251(13) Uani 1 1 d . . . H14A H 0.8001 0.4964 -0.4448 0.030 Uiso 1 1 calc R . . C15 C 0.9629(3) 0.1212(2) 0.1795(5) 0.0170(11) Uani 1 1 d . . . C16 C 1.0508(3) 0.1427(3) 0.2182(6) 0.0252(13) Uani 1 1 d . . . H16A H 1.0926 0.1604 0.1504 0.030 Uiso 1 1 calc R . . C17 C 1.0772(4) 0.1385(3) 0.3536(6) 0.0305(14) Uani 1 1 d . . . H17A H 1.1377 0.1513 0.3782 0.037 Uiso 1 1 calc R . . C18 C 1.0167(4) 0.1159(3) 0.4525(6) 0.0285(13) Uani 1 1 d . . . H18A H 1.0350 0.1145 0.5460 0.034 Uiso 1 1 calc R . . C19 C 0.9278(4) 0.0947(3) 0.4174(6) 0.0285(14) Uani 1 1 d . . . H19A H 0.8862 0.0786 0.4867 0.034 Uiso 1 1 calc R . . C20 C 0.9013(4) 0.0973(3) 0.2825(6) 0.0230(13) Uani 1 1 d . . . H20A H 0.8411 0.0829 0.2584 0.028 Uiso 1 1 calc R . . C21 C 0.6563(3) 0.1367(3) -0.1701(5) 0.0176(11) Uani 1 1 d . . . C22 C 0.5681(3) 0.1072(3) -0.1848(6) 0.0220(13) Uani 1 1 d . . . H22A H 0.5367 0.0873 -0.1063 0.026 Uiso 1 1 calc R . . C23 C 0.5258(3) 0.1064(3) -0.3111(6) 0.0225(12) Uani 1 1 d . . . H23A H 0.4654 0.0872 -0.3192 0.027 Uiso 1 1 calc R . . C24 C 0.5718(3) 0.1336(3) -0.4250(6) 0.0244(13) Uani 1 1 d . . . H24A H 0.5430 0.1333 -0.5121 0.029 Uiso 1 1 calc R . . C25 C 0.6612(3) 0.1619(3) -0.4136(6) 0.0238(13) Uani 1 1 d . . . H25A H 0.6932 0.1795 -0.4930 0.029 Uiso 1 1 calc R . . C26 C 0.7020(3) 0.1639(3) -0.2874(6) 0.0205(12) Uani 1 1 d . . . H26A H 0.7620 0.1841 -0.2795 0.025 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 0.0177(3) 0.0299(3) 0.0282(4) 0.0040(3) 0.0079(3) 0.0035(2) P1 0.0120(6) 0.0176(6) 0.0179(8) 0.0023(6) 0.0004(6) 0.0008(5) Se2 0.0159(2) 0.0156(3) 0.0231(3) -0.0020(2) -0.0004(3) 0.00077(19) P3 0.0131(6) 0.0153(6) 0.0187(8) -0.0011(6) 0.0002(6) 0.0002(5) Se3 0.0176(3) 0.0249(3) 0.0213(3) 0.0020(2) 0.0046(2) 0.0010(2) N4 0.010(2) 0.018(2) 0.017(3) 0.0012(18) 0.002(2) -0.0017(15) C5 0.022(3) 0.014(2) 0.014(3) 0.000(2) 0.003(2) 0.0002(19) N5 0.011(2) 0.012(2) 0.017(2) 0.0038(17) -0.003(2) -0.0030(15) C6 0.014(2) 0.016(2) 0.020(3) 0.001(2) 0.002(2) 0.003(2) C7 0.012(2) 0.017(2) 0.016(3) 0.000(2) -0.003(2) 0.006(2) C8 0.014(2) 0.027(3) 0.012(3) -0.002(2) -0.003(2) 0.000(2) C9 0.011(2) 0.031(3) 0.015(3) 0.002(2) 0.002(2) -0.002(2) C10 0.023(3) 0.030(3) 0.016(3) 0.004(2) 0.002(3) -0.001(2) C11 0.032(3) 0.040(3) 0.012(3) -0.005(3) 0.008(3) -0.006(2) C12 0.020(3) 0.053(4) 0.009(3) 0.006(3) 0.001(2) -0.003(3) C13 0.021(3) 0.039(3) 0.029(4) 0.012(3) 0.007(3) 0.006(2) C14 0.023(3) 0.027(3) 0.026(4) 0.002(2) 0.007(3) -0.001(2) C15 0.020(3) 0.010(2) 0.021(3) 0.004(2) -0.006(2) 0.0010(19) C16 0.021(3) 0.018(3) 0.037(4) 0.010(3) -0.003(3) -0.001(2) C17 0.027(3) 0.027(3) 0.038(4) 0.003(3) -0.015(3) -0.001(2) C18 0.043(3) 0.021(3) 0.021(3) -0.004(3) -0.016(3) 0.010(2) C19 0.044(4) 0.028(3) 0.014(3) 0.005(2) 0.003(3) 0.005(3) C20 0.025(3) 0.017(3) 0.027(3) 0.004(2) -0.001(3) 0.003(2) C21 0.018(2) 0.014(2) 0.021(3) -0.001(2) -0.005(2) 0.0031(19) C22 0.019(3) 0.021(3) 0.026(4) 0.000(2) -0.001(3) 0.007(2) C23 0.010(2) 0.029(3) 0.028(4) -0.004(2) -0.002(3) 0.000(2) C24 0.021(3) 0.031(3) 0.021(3) -0.005(3) -0.006(3) 0.004(2) C25 0.027(3) 0.025(3) 0.019(3) 0.004(2) -0.002(3) -0.008(2) C26 0.016(3) 0.026(3) 0.019(3) 0.000(2) 0.001(2) -0.005(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 2.0833(13) . ? P1 C15 1.801(5) . ? P1 C5 1.901(4) . ? P1 Se2 2.2334(13) . ? Se2 P3 2.2976(12) . ? P3 N4 1.647(3) . ? P3 C21 1.800(5) . ? P3 Se3 2.0943(14) . ? N4 C5 1.283(5) . ? C5 N5 1.331(5) . ? N5 C6 1.484(5) . ? N5 H5N 0.980(3) . ? C6 C7 1.526(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.536(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.502(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.388(6) . ? C9 C10 1.393(7) . ? C10 C11 1.381(7) . ? C10 H10A 0.9500 . ? C11 C12 1.382(7) . ? C11 H11A 0.9500 . ? C12 C13 1.376(7) . ? C12 H12A 0.9500 . ? C13 C14 1.389(7) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? C15 C16 1.399(6) . ? C15 C20 1.409(7) . ? C16 C17 1.377(7) . ? C16 H16A 0.9500 . ? C17 C18 1.365(7) . ? C17 H17A 0.9500 . ? C18 C19 1.402(7) . ? C18 H18A 0.9500 . ? C19 C20 1.371(7) . ? C19 H19A 0.9500 . ? C20 H20A 0.9500 . ? C21 C22 1.397(6) . ? C21 C26 1.397(7) . ? C22 C23 1.381(7) . ? C22 H22A 0.9500 . ? C23 C24 1.373(7) . ? C23 H23A 0.9500 . ? C24 C25 1.404(6) . ? C24 H24A 0.9500 . ? C25 C26 1.369(7) . ? C25 H25A 0.9500 . ? C26 H26A 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 C15 P1 C5 105.3(2) . . ? C15 P1 Se1 114.96(16) . . ? C5 P1 Se1 111.02(16) . . ? C15 P1 Se2 107.68(15) . . ? C5 P1 Se2 97.41(14) . . ? Se1 P1 Se2 118.40(6) . . ? P1 Se2 P3 90.99(4) . . ? N4 P3 C21 104.9(2) . . ? N4 P3 Se3 116.10(16) . . ? C21 P3 Se3 114.16(16) . . ? N4 P3 Se2 103.59(13) . . ? C21 P3 Se2 102.08(15) . . ? Se3 P3 Se2 114.38(6) . . ? C5 N4 P3 123.2(3) . . ? N4 C5 N5 124.5(4) . . ? N4 C5 P1 122.9(3) . . ? N5 C5 P1 112.7(3) . . ? C5 N5 C6 120.5(4) . . ? C5 N5 H5N 116(3) . . ? C6 N5 H5N 124(3) . . ? N5 C6 C7 111.0(4) . . ? N5 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N5 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C6 C7 C8 113.2(3) . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C7 111.7(3) . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C14 C9 C10 117.7(5) . . ? C14 C9 C8 121.1(5) . . ? C10 C9 C8 121.1(4) . . ? C11 C10 C9 121.3(5) . . ? C11 C10 H10A 119.3 . . ? C9 C10 H10A 119.3 . . ? C10 C11 C12 120.3(5) . . ? C10 C11 H11A 119.9 . . ? C12 C11 H11A 119.9 . . ? C13 C12 C11 119.2(5) . . ? C13 C12 H12A 120.4 . . ? C11 C12 H12A 120.4 . . ? C12 C13 C14 120.5(5) . . ? C12 C13 H13A 119.7 . . ? C14 C13 H13A 119.7 . . ? C9 C14 C13 121.0(5) . . ? C9 C14 H14A 119.5 . . ? C13 C14 H14A 119.5 . . ? C16 C15 C20 118.6(5) . . ? C16 C15 P1 120.2(4) . . ? C20 C15 P1 121.2(4) . . ? C17 C16 C15 120.7(5) . . ? C17 C16 H16A 119.6 . . ? C15 C16 H16A 119.6 . . ? C18 C17 C16 120.1(5) . . ? C18 C17 H17A 120.0 . . ? C16 C17 H17A 120.0 . . ? C17 C18 C19 120.6(5) . . ? C17 C18 H18A 119.7 . . ? C19 C18 H18A 119.7 . . ? C20 C19 C18 119.7(6) . . ? C20 C19 H19A 120.2 . . ? C18 C19 H19A 120.2 . . ? C19 C20 C15 120.2(5) . . ? C19 C20 H20A 119.9 . . ? C15 C20 H20A 119.9 . . ? C22 C21 C26 118.4(5) . . ? C22 C21 P3 121.0(4) . . ? C26 C21 P3 120.6(4) . . ? C23 C22 C21 121.2(5) . . ? C23 C22 H22A 119.4 . . ? C21 C22 H22A 119.4 . . ? C24 C23 C22 119.3(5) . . ? C24 C23 H23A 120.3 . . ? C22 C23 H23A 120.3 . . ? C23 C24 C25 120.6(5) . . ? C23 C24 H24A 119.7 . . ? C25 C24 H24A 119.7 . . ? C26 C25 C24 119.6(5) . . ? C26 C25 H25A 120.2 . . ? C24 C25 H25A 120.2 . . ? C25 C26 C21 120.8(5) . . ? C25 C26 H26A 119.6 . . ? C21 C26 H26A 119.6 . . ? 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 C15 P1 Se2 P3 97.55(16) . . . . ? C5 P1 Se2 P3 -11.14(17) . . . . ? Se1 P1 Se2 P3 -129.92(7) . . . . ? P1 Se2 P3 N4 9.30(16) . . . . ? P1 Se2 P3 C21 118.15(16) . . . . ? P1 Se2 P3 Se3 -118.03(7) . . . . ? C21 P3 N4 C5 -109.2(5) . . . . ? Se3 P3 N4 C5 123.8(4) . . . . ? Se2 P3 N4 C5 -2.5(5) . . . . ? P3 N4 C5 N5 171.1(4) . . . . ? P3 N4 C5 P1 -8.7(7) . . . . ? C15 P1 C5 N4 -96.2(5) . . . . ? Se1 P1 C5 N4 138.8(4) . . . . ? Se2 P1 C5 N4 14.5(5) . . . . ? C15 P1 C5 N5 84.1(4) . . . . ? Se1 P1 C5 N5 -40.9(4) . . . . ? Se2 P1 C5 N5 -165.3(4) . . . . ? N4 C5 N5 C6 -3.7(8) . . . . ? P1 C5 N5 C6 176.1(3) . . . . ? C5 N5 C6 C7 -71.6(6) . . . . ? N5 C6 C7 C8 -64.7(5) . . . . ? C6 C7 C8 C9 174.7(4) . . . . ? C7 C8 C9 C14 71.6(5) . . . . ? C7 C8 C9 C10 -105.1(5) . . . . ? C14 C9 C10 C11 0.4(7) . . . . ? C8 C9 C10 C11 177.3(4) . . . . ? C9 C10 C11 C12 -1.0(7) . . . . ? C10 C11 C12 C13 1.3(7) . . . . ? C11 C12 C13 C14 -1.2(7) . . . . ? C10 C9 C14 C13 -0.3(7) . . . . ? C8 C9 C14 C13 -177.2(4) . . . . ? C12 C13 C14 C9 0.7(7) . . . . ? C5 P1 C15 C16 -104.0(4) . . . . ? Se1 P1 C15 C16 18.5(4) . . . . ? Se2 P1 C15 C16 152.8(3) . . . . ? C5 P1 C15 C20 73.6(4) . . . . ? Se1 P1 C15 C20 -163.9(3) . . . . ? Se2 P1 C15 C20 -29.5(4) . . . . ? C20 C15 C16 C17 1.7(7) . . . . ? P1 C15 C16 C17 179.4(4) . . . . ? C15 C16 C17 C18 -2.3(7) . . . . ? C16 C17 C18 C19 1.7(7) . . . . ? C17 C18 C19 C20 -0.5(7) . . . . ? C18 C19 C20 C15 -0.1(7) . . . . ? C16 C15 C20 C19 -0.5(7) . . . . ? P1 C15 C20 C19 -178.2(4) . . . . ? N4 P3 C21 C22 -142.2(4) . . . . ? Se3 P3 C21 C22 -14.0(4) . . . . ? Se2 P3 C21 C22 110.0(3) . . . . ? N4 P3 C21 C26 39.4(4) . . . . ? Se3 P3 C21 C26 167.6(3) . . . . ? Se2 P3 C21 C26 -68.4(4) . . . . ? C26 C21 C22 C23 -1.5(7) . . . . ? P3 C21 C22 C23 -179.9(3) . . . . ? C21 C22 C23 C24 1.3(7) . . . . ? C22 C23 C24 C25 0.1(7) . . . . ? C23 C24 C25 C26 -1.4(7) . . . . ? C24 C25 C26 C21 1.2(7) . . . . ? C22 C21 C26 C25 0.2(7) . . . . ? P3 C21 C26 C25 178.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.658 _refine_diff_density_min -0.586 _refine_diff_density_rms 0.119 # Attachment '3.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 690503' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 N2 P Se2' _chemical_formula_sum 'C16 H19 N2 P Se2' _chemical_formula_weight 428.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 21.784(3) _cell_length_b 6.8434(7) _cell_length_c 23.320(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.307(4) _cell_angle_gamma 90.00 _cell_volume 3440.1(8) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 6207 _cell_measurement_theta_min 1.2795 _cell_measurement_theta_max 28.2566 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 4.387 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4741 _exptl_absorpt_correction_T_max 0.8441 _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 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 22372 _diffrn_reflns_av_R_equivalents 0.1076 _diffrn_reflns_av_sigmaI/netI 0.1158 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.20 _diffrn_reflns_theta_max 28.51 _reflns_number_total 6871 _reflns_number_gt 5755 _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 PLATON _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^)+(0.0927P)^2^+2.7770P] 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 6871 _refine_ls_number_parameters 393 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1680 _refine_ls_wR_factor_gt 0.1388 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.007 _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 Se2 Se 0.05849(2) 0.40907(7) 0.45405(2) 0.01875(16) Uani 1 1 d . . . Se22 Se 0.48678(2) 0.32741(6) 0.60277(2) 0.01976(16) Uani 1 1 d . . . Se1 Se 0.14574(2) -0.02621(7) 0.42051(2) 0.02197(16) Uani 1 1 d . . . Se21 Se 0.41519(2) -0.15836(8) 0.58817(3) 0.02917(18) Uani 1 1 d . . . P1 P 0.12492(6) 0.18696(17) 0.48142(5) 0.0151(3) Uani 1 1 d . . . P21 P 0.49372(6) 0.01983(17) 0.61743(6) 0.0182(3) Uani 1 1 d . . . N23 N 0.61668(19) -0.0280(6) 0.58769(18) 0.0206(9) Uani 1 1 d . . . C2 C 0.0892(2) 0.0506(7) 0.5395(2) 0.0171(9) Uani 1 1 d . . . N3 N 0.07955(18) 0.1234(6) 0.58974(17) 0.0171(8) Uani 1 1 d . . . C23 C 0.6615(3) -0.1195(8) 0.5537(2) 0.0281(12) Uani 1 1 d . . . H23A H 0.6553 -0.2613 0.5525 0.042 Uiso 1 1 calc R . . H23B H 0.7039 -0.0901 0.5719 0.042 Uiso 1 1 calc R . . H23C H 0.6550 -0.0675 0.5141 0.042 Uiso 1 1 calc R . . C36 C 0.5522(2) 0.0629(8) 0.7922(2) 0.0216(10) Uani 1 1 d . . . H36 H 0.5613 0.1638 0.8202 0.026 Uiso 1 1 calc R . . C28 C 0.7819(3) 0.6419(9) 0.6797(3) 0.0357(14) Uani 1 1 d . . . H28 H 0.8250 0.6701 0.6827 0.043 Uiso 1 1 calc R . . C16 C 0.2928(2) 0.2283(8) 0.5835(2) 0.0267(11) Uani 1 1 d . . . H16 H 0.3204 0.1430 0.6067 0.032 Uiso 1 1 calc R . . C12 C 0.1968(2) 0.2846(7) 0.5208(2) 0.0190(10) Uani 1 1 d . . . C37 C 0.5355(2) 0.1105(7) 0.7340(2) 0.0197(10) Uani 1 1 d . . . H37 H 0.5343 0.2434 0.7221 0.024 Uiso 1 1 calc R . . C30 C 0.6841(3) 0.6985(8) 0.7106(3) 0.0291(12) Uani 1 1 d . . . H30 H 0.6599 0.7646 0.7353 0.035 Uiso 1 1 calc R . . C35 C 0.5557(2) -0.1308(8) 0.8096(2) 0.0246(11) Uani 1 1 d . . . H35 H 0.5683 -0.1629 0.8492 0.030 Uiso 1 1 calc R . . N2 N 0.0713(2) -0.1279(6) 0.52458(19) 0.0219(9) Uani 1 1 d D . . C5 C 0.1475(2) 0.3284(7) 0.6611(2) 0.0239(11) Uani 1 1 d . . . H5A H 0.1399 0.2267 0.6894 0.029 Uiso 1 1 calc R . . H5B H 0.1868 0.2959 0.6466 0.029 Uiso 1 1 calc R . . C25 C 0.6628(3) 0.3034(7) 0.5955(2) 0.0252(11) Uani 1 1 d . . . H25A H 0.6928 0.2609 0.5699 0.030 Uiso 1 1 calc R . . H25B H 0.6263 0.3596 0.5707 0.030 Uiso 1 1 calc R . . N22 N 0.5390(2) -0.2103(6) 0.5380(2) 0.0271(10) Uani 1 1 d D . . C11 C 0.1190(2) 0.5671(8) 0.7355(2) 0.0235(11) Uani 1 1 d . . . H11 H 0.0893 0.4754 0.7449 0.028 Uiso 1 1 calc R . . C14 C 0.2695(2) 0.5481(8) 0.5426(2) 0.0256(11) Uani 1 1 d . . . H14 H 0.2814 0.6800 0.5378 0.031 Uiso 1 1 calc R . . C26 C 0.6923(2) 0.4580(7) 0.6365(2) 0.0234(11) Uani 1 1 d . . . C24 C 0.6424(2) 0.1266(7) 0.6279(2) 0.0212(10) Uani 1 1 d . . . H24A H 0.6784 0.0745 0.6542 0.025 Uiso 1 1 calc R . . H24B H 0.6106 0.1676 0.6519 0.025 Uiso 1 1 calc R . . C6 C 0.1544(2) 0.5232(7) 0.6913(2) 0.0204(10) Uani 1 1 d . . . C32 C 0.5204(2) -0.0378(7) 0.6933(2) 0.0167(9) Uani 1 1 d . . . C17 C 0.2368(2) 0.1597(7) 0.5557(2) 0.0214(10) Uani 1 1 d . . . H17 H 0.2254 0.0272 0.5603 0.026 Uiso 1 1 calc R . . C7 C 0.1972(2) 0.6637(8) 0.6783(2) 0.0260(12) Uani 1 1 d . . . H7 H 0.2210 0.6389 0.6480 0.031 Uiso 1 1 calc R . . C9 C 0.1704(3) 0.8755(8) 0.7532(2) 0.0298(12) Uani 1 1 d . . . H9 H 0.1768 0.9931 0.7749 0.036 Uiso 1 1 calc R . . C4 C 0.0942(2) 0.3245(7) 0.6099(2) 0.0193(10) Uani 1 1 d . . . H4A H 0.0568 0.3848 0.6220 0.023 Uiso 1 1 calc R . . H4B H 0.1061 0.4028 0.5775 0.023 Uiso 1 1 calc R . . C31 C 0.6565(2) 0.5593(7) 0.6721(2) 0.0242(11) Uani 1 1 d . . . H31 H 0.6135 0.5326 0.6698 0.029 Uiso 1 1 calc R . . C34 C 0.5408(2) -0.2777(7) 0.7691(2) 0.0242(11) Uani 1 1 d . . . H34 H 0.5435 -0.4105 0.7810 0.029 Uiso 1 1 calc R . . C15 C 0.3087(2) 0.4243(8) 0.5772(2) 0.0273(12) Uani 1 1 d . . . H15 H 0.3468 0.4726 0.5969 0.033 Uiso 1 1 calc R . . C13 C 0.2125(2) 0.4809(7) 0.5146(2) 0.0209(10) Uani 1 1 d . . . H13 H 0.1848 0.5670 0.4917 0.025 Uiso 1 1 calc R . . C22 C 0.5583(3) -0.0804(7) 0.5782(2) 0.0207(10) Uani 1 1 d . . . C27 C 0.7563(3) 0.4996(8) 0.6411(2) 0.0269(12) Uani 1 1 d . . . H27 H 0.7816 0.4308 0.6180 0.032 Uiso 1 1 calc R . . C3 C 0.0487(2) 0.0009(8) 0.6292(2) 0.0247(11) Uani 1 1 d . . . H3A H 0.0061 -0.0275 0.6111 0.037 Uiso 1 1 calc R . . H3B H 0.0478 0.0707 0.6657 0.037 Uiso 1 1 calc R . . H3C H 0.0716 -0.1218 0.6368 0.037 Uiso 1 1 calc R . . C8 C 0.2054(3) 0.8372(8) 0.7086(3) 0.0296(12) Uani 1 1 d . . . H8 H 0.2346 0.9305 0.6991 0.036 Uiso 1 1 calc R . . C33 C 0.5220(2) -0.2330(7) 0.7113(2) 0.0217(10) Uani 1 1 d . . . H33 H 0.5102 -0.3342 0.6840 0.026 Uiso 1 1 calc R . . C10 C 0.1268(3) 0.7425(8) 0.7657(2) 0.0275(11) Uani 1 1 d . . . H10 H 0.1021 0.7707 0.7950 0.033 Uiso 1 1 calc R . . C29 C 0.7464(3) 0.7421(8) 0.7135(2) 0.0299(12) Uani 1 1 d . . . H29 H 0.7645 0.8415 0.7389 0.036 Uiso 1 1 calc R . . H2B H 0.041(2) -0.210(7) 0.541(3) 0.036 Uiso 1 1 d D . . H2A H 0.079(3) -0.153(8) 0.4848(9) 0.036 Uiso 1 1 d D . . H22B H 0.563(2) -0.242(9) 0.5067(18) 0.036 Uiso 1 1 d D . . H22A H 0.4949(8) -0.246(9) 0.533(3) 0.036 Uiso 1 1 d 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 Se2 0.0194(3) 0.0165(3) 0.0198(3) 0.00109(17) 0.0010(2) -0.00072(17) Se22 0.0267(3) 0.0145(3) 0.0171(3) -0.00083(16) -0.0003(2) 0.00202(17) Se1 0.0256(3) 0.0208(3) 0.0212(3) -0.00648(18) 0.0091(2) -0.00301(18) Se21 0.0244(3) 0.0206(3) 0.0383(4) -0.0023(2) -0.0099(3) -0.00187(19) P1 0.0168(6) 0.0150(6) 0.0140(6) -0.0030(4) 0.0035(5) -0.0018(4) P21 0.0212(7) 0.0150(6) 0.0175(7) -0.0011(4) -0.0007(5) 0.0008(4) N23 0.024(2) 0.019(2) 0.019(2) -0.0007(16) 0.0055(18) 0.0057(16) C2 0.017(2) 0.014(2) 0.021(2) -0.0007(18) 0.0052(19) 0.0018(17) N3 0.019(2) 0.015(2) 0.019(2) -0.0041(15) 0.0083(17) -0.0028(15) C23 0.038(3) 0.023(3) 0.026(3) -0.002(2) 0.014(2) 0.010(2) C36 0.024(3) 0.026(3) 0.015(2) 0.0011(19) 0.003(2) -0.0001(19) C28 0.016(3) 0.041(3) 0.048(4) 0.014(3) -0.002(3) 0.000(2) C16 0.016(3) 0.034(3) 0.030(3) -0.012(2) 0.003(2) 0.004(2) C12 0.016(2) 0.024(3) 0.019(2) -0.0072(19) 0.009(2) -0.0013(18) C37 0.014(2) 0.022(3) 0.023(3) 0.0030(19) 0.002(2) -0.0018(17) C30 0.034(3) 0.021(3) 0.032(3) 0.001(2) 0.004(3) 0.001(2) C35 0.025(3) 0.035(3) 0.015(3) 0.001(2) 0.006(2) 0.001(2) N2 0.023(2) 0.021(2) 0.023(2) -0.0041(17) 0.0084(19) -0.0051(17) C5 0.025(3) 0.027(3) 0.020(3) -0.0046(19) 0.004(2) 0.0032(19) C25 0.030(3) 0.025(3) 0.021(3) 0.002(2) 0.006(2) 0.001(2) N22 0.042(3) 0.019(2) 0.021(2) -0.0017(17) 0.006(2) 0.0024(19) C11 0.020(3) 0.030(3) 0.022(3) 0.001(2) 0.009(2) -0.0027(19) C14 0.024(3) 0.025(3) 0.028(3) -0.007(2) 0.006(2) -0.013(2) C26 0.026(3) 0.023(3) 0.022(3) 0.008(2) 0.005(2) 0.0000(19) C24 0.023(3) 0.022(3) 0.019(3) 0.0031(19) 0.008(2) 0.0062(19) C6 0.027(3) 0.022(3) 0.013(2) 0.0015(17) 0.003(2) 0.0046(19) C32 0.014(2) 0.020(2) 0.016(2) 0.0004(18) 0.0030(19) 0.0013(17) C17 0.018(3) 0.021(3) 0.026(3) -0.0023(19) 0.005(2) 0.0007(18) C7 0.019(3) 0.033(3) 0.026(3) 0.003(2) 0.005(2) 0.006(2) C9 0.035(3) 0.027(3) 0.024(3) -0.008(2) -0.009(2) -0.003(2) C4 0.024(3) 0.018(3) 0.017(2) -0.0008(17) 0.007(2) -0.0035(18) C31 0.018(3) 0.026(3) 0.029(3) -0.002(2) 0.004(2) -0.0015(19) C34 0.038(3) 0.016(3) 0.021(3) -0.0005(18) 0.013(2) 0.002(2) C15 0.015(3) 0.039(3) 0.028(3) -0.008(2) 0.004(2) -0.009(2) C13 0.022(3) 0.023(3) 0.020(3) -0.0027(18) 0.008(2) -0.0016(18) C22 0.036(3) 0.013(2) 0.014(2) 0.0029(17) 0.008(2) 0.0063(19) C27 0.029(3) 0.027(3) 0.025(3) 0.006(2) 0.005(2) 0.003(2) C3 0.026(3) 0.026(3) 0.023(3) 0.001(2) 0.007(2) 0.000(2) C8 0.031(3) 0.025(3) 0.032(3) 0.002(2) 0.000(2) -0.006(2) C33 0.023(3) 0.023(3) 0.022(3) 0.0001(19) 0.010(2) 0.0019(19) C10 0.033(3) 0.029(3) 0.021(3) -0.004(2) 0.005(2) 0.001(2) C29 0.032(3) 0.021(3) 0.033(3) -0.002(2) -0.004(2) -0.007(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 Se2 P1 2.1319(13) . ? Se22 P21 2.1343(13) . ? Se1 P1 2.1302(12) . ? Se21 P21 2.1313(14) . ? P1 C12 1.823(5) . ? P1 C2 1.902(5) . ? P21 C32 1.824(5) . ? P21 C22 1.913(5) . ? N23 C22 1.309(7) . ? N23 C24 1.470(6) . ? N23 C23 1.483(6) . ? C2 N2 1.314(6) . ? C2 N3 1.317(6) . ? N3 C4 1.475(6) . ? N3 C3 1.476(6) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C36 C35 1.385(7) . ? C36 C37 1.393(7) . ? C36 H36 0.9500 . ? C28 C29 1.365(9) . ? C28 C27 1.387(8) . ? C28 H28 0.9500 . ? C16 C17 1.378(7) . ? C16 C15 1.399(8) . ? C16 H16 0.9500 . ? C12 C17 1.395(7) . ? C12 C13 1.400(7) . ? C37 C32 1.397(7) . ? C37 H37 0.9500 . ? C30 C29 1.383(8) . ? C30 C31 1.385(7) . ? C30 H30 0.9500 . ? C35 C34 1.387(7) . ? C35 H35 0.9500 . ? N2 H2B 0.99(5) . ? N2 H2A 0.98(5) . ? C5 C6 1.505(7) . ? C5 C4 1.540(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C25 C26 1.507(7) . ? C25 C24 1.527(7) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N22 C22 1.316(7) . ? N22 H22B 0.98(4) . ? N22 H22A 0.98(4) . ? C11 C10 1.389(7) . ? C11 C6 1.406(7) . ? C11 H11 0.9500 . ? C14 C15 1.377(8) . ? C14 C13 1.396(7) . ? C14 H14 0.9500 . ? C26 C31 1.401(7) . ? C26 C27 1.412(7) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C6 C7 1.403(7) . ? C32 C33 1.399(7) . ? C17 H17 0.9500 . ? C7 C8 1.380(8) . ? C7 H7 0.9500 . ? C9 C10 1.376(8) . ? C9 C8 1.401(8) . ? C9 H9 0.9500 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C31 H31 0.9500 . ? C34 C33 1.385(7) . ? C34 H34 0.9500 . ? C15 H15 0.9500 . ? C13 H13 0.9500 . ? C27 H27 0.9500 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C8 H8 0.9500 . ? C33 H33 0.9500 . ? C10 H10 0.9500 . ? C29 H29 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 C12 P1 C2 103.3(2) . . ? C12 P1 Se1 109.70(15) . . ? C2 P1 Se1 106.70(15) . . ? C12 P1 Se2 112.69(16) . . ? C2 P1 Se2 103.48(15) . . ? Se1 P1 Se2 119.30(6) . . ? C32 P21 C22 103.5(2) . . ? C32 P21 Se21 108.39(16) . . ? C22 P21 Se21 104.68(17) . . ? C32 P21 Se22 111.97(16) . . ? C22 P21 Se22 108.49(15) . . ? Se21 P21 Se22 118.55(6) . . ? C22 N23 C24 125.2(4) . . ? C22 N23 C23 119.5(4) . . ? C24 N23 C23 115.2(4) . . ? N2 C2 N3 120.5(4) . . ? N2 C2 P1 113.8(4) . . ? N3 C2 P1 125.6(4) . . ? C2 N3 C4 125.6(4) . . ? C2 N3 C3 119.0(4) . . ? C4 N3 C3 115.4(4) . . ? N23 C23 H23A 109.5 . . ? N23 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N23 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C35 C36 C37 120.3(5) . . ? C35 C36 H36 119.8 . . ? C37 C36 H36 119.8 . . ? C29 C28 C27 121.2(5) . . ? C29 C28 H28 119.4 . . ? C27 C28 H28 119.4 . . ? C17 C16 C15 119.5(5) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C17 C12 C13 120.5(5) . . ? C17 C12 P1 119.2(4) . . ? C13 C12 P1 120.3(4) . . ? C36 C37 C32 119.7(5) . . ? C36 C37 H37 120.1 . . ? C32 C37 H37 120.1 . . ? C29 C30 C31 120.7(5) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C36 C35 C34 119.8(5) . . ? C36 C35 H35 120.1 . . ? C34 C35 H35 120.1 . . ? C2 N2 H2B 128(4) . . ? C2 N2 H2A 109(4) . . ? H2B N2 H2A 118(5) . . ? C6 C5 C4 113.1(4) . . ? C6 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? C6 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C26 C25 C24 111.7(4) . . ? C26 C25 H25A 109.3 . . ? C24 C25 H25A 109.3 . . ? C26 C25 H25B 109.3 . . ? C24 C25 H25B 109.3 . . ? H25A C25 H25B 107.9 . . ? C22 N22 H22B 122(4) . . ? C22 N22 H22A 117(4) . . ? H22B N22 H22A 118(5) . . ? C10 C11 C6 121.1(5) . . ? C10 C11 H11 119.5 . . ? C6 C11 H11 119.5 . . ? C15 C14 C13 120.3(5) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C31 C26 C27 118.8(5) . . ? C31 C26 C25 120.1(5) . . ? C27 C26 C25 121.1(5) . . ? N23 C24 C25 111.4(4) . . ? N23 C24 H24A 109.4 . . ? C25 C24 H24A 109.4 . . ? N23 C24 H24B 109.4 . . ? C25 C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? C7 C6 C11 117.7(5) . . ? C7 C6 C5 122.0(4) . . ? C11 C6 C5 120.3(5) . . ? C37 C32 C33 119.8(4) . . ? C37 C32 P21 120.9(4) . . ? C33 C32 P21 119.2(4) . . ? C16 C17 C12 120.1(5) . . ? C16 C17 H17 120.0 . . ? C12 C17 H17 120.0 . . ? C8 C7 C6 121.2(5) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C10 C9 C8 119.9(5) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? N3 C4 C5 111.6(4) . . ? N3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? N3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C30 C31 C26 119.9(5) . . ? C30 C31 H31 120.0 . . ? C26 C31 H31 120.0 . . ? C33 C34 C35 120.7(5) . . ? C33 C34 H34 119.6 . . ? C35 C34 H34 119.6 . . ? C14 C15 C16 120.7(5) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C14 C13 C12 118.9(5) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? N23 C22 N22 120.6(5) . . ? N23 C22 P21 125.8(4) . . ? N22 C22 P21 113.7(4) . . ? C28 C27 C26 119.5(5) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? N3 C3 H3A 109.5 . . ? N3 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N3 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C7 C8 C9 119.9(5) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C34 C33 C32 119.6(5) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C9 C10 C11 120.1(5) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C28 C29 C30 119.9(5) . . ? C28 C29 H29 120.1 . . ? C30 C29 H29 120.1 . . ? 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 C12 P1 C2 N2 -130.8(4) . . . . ? Se1 P1 C2 N2 -15.1(4) . . . . ? Se2 P1 C2 N2 111.5(3) . . . . ? C12 P1 C2 N3 52.1(5) . . . . ? Se1 P1 C2 N3 167.8(4) . . . . ? Se2 P1 C2 N3 -65.5(4) . . . . ? N2 C2 N3 C4 -176.3(5) . . . . ? P1 C2 N3 C4 0.6(7) . . . . ? N2 C2 N3 C3 0.4(7) . . . . ? P1 C2 N3 C3 177.3(4) . . . . ? C2 P1 C12 C17 50.3(4) . . . . ? Se1 P1 C12 C17 -63.2(4) . . . . ? Se2 P1 C12 C17 161.3(3) . . . . ? C2 P1 C12 C13 -131.9(4) . . . . ? Se1 P1 C12 C13 114.6(4) . . . . ? Se2 P1 C12 C13 -20.8(4) . . . . ? C35 C36 C37 C32 1.8(7) . . . . ? C37 C36 C35 C34 -1.8(8) . . . . ? C24 C25 C26 C31 -67.1(6) . . . . ? C24 C25 C26 C27 111.0(5) . . . . ? C22 N23 C24 C25 -110.6(5) . . . . ? C23 N23 C24 C25 65.7(5) . . . . ? C26 C25 C24 N23 -177.0(4) . . . . ? C10 C11 C6 C7 -0.8(8) . . . . ? C10 C11 C6 C5 177.1(5) . . . . ? C4 C5 C6 C7 -96.3(6) . . . . ? C4 C5 C6 C11 85.9(6) . . . . ? C36 C37 C32 C33 0.3(7) . . . . ? C36 C37 C32 P21 176.2(4) . . . . ? C22 P21 C32 C37 114.8(4) . . . . ? Se21 P21 C32 C37 -134.5(4) . . . . ? Se22 P21 C32 C37 -1.9(4) . . . . ? C22 P21 C32 C33 -69.3(4) . . . . ? Se21 P21 C32 C33 41.5(4) . . . . ? Se22 P21 C32 C33 174.1(3) . . . . ? C15 C16 C17 C12 1.0(8) . . . . ? C13 C12 C17 C16 -1.2(7) . . . . ? P1 C12 C17 C16 176.7(4) . . . . ? C11 C6 C7 C8 1.4(8) . . . . ? C5 C6 C7 C8 -176.5(5) . . . . ? C2 N3 C4 C5 -112.0(5) . . . . ? C3 N3 C4 C5 71.3(5) . . . . ? C6 C5 C4 N3 -167.2(4) . . . . ? C29 C30 C31 C26 1.5(8) . . . . ? C27 C26 C31 C30 0.5(8) . . . . ? C25 C26 C31 C30 178.6(5) . . . . ? C36 C35 C34 C33 -0.5(8) . . . . ? C13 C14 C15 C16 1.9(8) . . . . ? C17 C16 C15 C14 -1.4(8) . . . . ? C15 C14 C13 C12 -2.0(8) . . . . ? C17 C12 C13 C14 1.6(7) . . . . ? P1 C12 C13 C14 -176.2(4) . . . . ? C24 N23 C22 N22 174.7(4) . . . . ? C23 N23 C22 N22 -1.5(7) . . . . ? C24 N23 C22 P21 -3.9(7) . . . . ? C23 N23 C22 P21 179.9(4) . . . . ? C32 P21 C22 N23 -59.0(5) . . . . ? Se21 P21 C22 N23 -172.5(4) . . . . ? Se22 P21 C22 N23 60.1(4) . . . . ? C32 P21 C22 N22 122.3(4) . . . . ? Se21 P21 C22 N22 8.9(4) . . . . ? Se22 P21 C22 N22 -118.6(3) . . . . ? C29 C28 C27 C26 0.2(8) . . . . ? C31 C26 C27 C28 -1.3(8) . . . . ? C25 C26 C27 C28 -179.5(5) . . . . ? C6 C7 C8 C9 -0.1(8) . . . . ? C10 C9 C8 C7 -1.8(8) . . . . ? C35 C34 C33 C32 2.6(8) . . . . ? C37 C32 C33 C34 -2.5(7) . . . . ? P21 C32 C33 C34 -178.5(4) . . . . ? C8 C9 C10 C11 2.4(8) . . . . ? C6 C11 C10 C9 -1.1(8) . . . . ? C27 C28 C29 C30 1.7(9) . . . . ? C31 C30 C29 C28 -2.6(8) . . . . ? 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 H2A Se1 0.98(3) 2.40(4) 3.185(4) 137(5) . N2 H2B Se2 0.99(5) 2.58(5) 3.514(4) 160(5) 3_556 N22 H22A Se21 0.98(2) 2.38(5) 3.111(5) 131(5) . N22 H22B Se22 0.98(4) 2.69(5) 3.346(5) 125(4) 3_656 _diffrn_measured_fraction_theta_max 0.786 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.247 _refine_diff_density_min -1.202 _refine_diff_density_rms 0.221 # Attachment '4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 690504' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_absolute_configuration unk _chemical_formula_sum 'C16 H19 N2 P Se2' _chemical_formula_weight 428.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 13.1547(7) _cell_length_b 7.4543(4) _cell_length_c 35.8185(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3512.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 24754 _cell_measurement_theta_min 1.05 _cell_measurement_theta_max 27.96 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.010 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.620 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 4.297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6054 _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 scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30063 _diffrn_reflns_av_R_equivalents 0.0740 _diffrn_reflns_av_sigmaI/netI 0.0260 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3220 _reflns_number_gt 3197 _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 ; The Flack parameter suggested an inversion twin, the data was merged and no Flack parameter is given. 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^)+(0.0135P)^2^+12.0856P] 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 3220 _refine_ls_number_parameters 404 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0742 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 1.210 _refine_ls_restrained_S_all 1.209 _refine_ls_shift/su_max 0.032 _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 0.81310(5) 0.39810(10) 0.79509(2) 0.02163(17) Uani 1 1 d . . . Se2 Se 0.57477(5) 0.65467(9) 0.81288(2) 0.01792(16) Uani 1 1 d . . . P1 P 0.65889(14) 0.4610(2) 0.78101(5) 0.0165(4) Uani 1 1 d . . . C2 C 0.5855(5) 0.2456(9) 0.7864(2) 0.0155(14) Uani 1 1 d . . . N2 N 0.6390(5) 0.0932(8) 0.7890(2) 0.0265(15) Uani 1 1 d D . . H2A H 0.7120(12) 0.119(9) 0.790(2) 0.008(17) Uiso 1 1 d D . . H2B H 0.610(7) -0.017(8) 0.799(3) 0.06(3) Uiso 1 1 d D . . N3 N 0.4862(5) 0.2518(8) 0.78587(18) 0.0200(13) Uani 1 1 d D . . H3N H 0.458(6) 0.359(7) 0.798(2) 0.03(2) Uiso 1 1 d D . . C4 C 0.4187(6) 0.0949(9) 0.7820(2) 0.0215(16) Uani 1 1 d . . . H4A H 0.3485 0.1292 0.7889 0.026 Uiso 1 1 calc R . . H4B H 0.4413 -0.0011 0.7992 0.026 Uiso 1 1 calc R . . C5 C 0.4195(6) 0.0243(10) 0.7420(2) 0.0219(16) Uani 1 1 d . . . H5A H 0.3785 -0.0870 0.7409 0.026 Uiso 1 1 calc R . . H5B H 0.4902 -0.0073 0.7351 0.026 Uiso 1 1 calc R . . C6 C 0.3779(7) 0.1574(11) 0.7131(3) 0.0319(19) Uani 1 1 d . . . H6A H 0.3045 0.1775 0.7177 0.038 Uiso 1 1 calc R . . H6B H 0.4133 0.2738 0.7157 0.038 Uiso 1 1 calc R . . C7 C 0.3929(6) 0.0864(10) 0.6740(2) 0.0259(18) Uani 1 1 d . . . C8 C 0.3132(7) -0.0014(13) 0.6545(3) 0.036(2) Uani 1 1 d . . . H8A H 0.2476 -0.0075 0.6656 0.043 Uiso 1 1 calc R . . C9 C 0.3282(9) -0.0776(13) 0.6203(3) 0.041(2) Uani 1 1 d . . . H9A H 0.2732 -0.1345 0.6078 0.049 Uiso 1 1 calc R . . C10 C 0.4251(8) -0.0723(12) 0.6032(3) 0.038(2) Uani 1 1 d . . . H10A H 0.4363 -0.1281 0.5797 0.045 Uiso 1 1 calc R . . C11 C 0.5028(8) 0.0156(13) 0.6214(3) 0.036(2) Uani 1 1 d . . . H11A H 0.5680 0.0225 0.6101 0.043 Uiso 1 1 calc R . . C12 C 0.4868(7) 0.0947(11) 0.6563(3) 0.032(2) Uani 1 1 d . . . H12A H 0.5414 0.1556 0.6682 0.039 Uiso 1 1 calc R . . C13 C 0.6423(5) 0.4969(10) 0.7302(2) 0.0193(15) Uani 1 1 d . . . C14 C 0.5558(7) 0.5845(11) 0.7172(2) 0.0271(18) Uani 1 1 d . . . H14A H 0.5051 0.6214 0.7345 0.033 Uiso 1 1 calc R . . C15 C 0.5424(8) 0.6190(12) 0.6794(3) 0.037(2) Uani 1 1 d . . . H15A H 0.4827 0.6771 0.6706 0.044 Uiso 1 1 calc R . . C16 C 0.6189(8) 0.5659(12) 0.6545(3) 0.036(2) Uani 1 1 d . . . H16A H 0.6123 0.5922 0.6286 0.043 Uiso 1 1 calc R . . C17 C 0.7030(8) 0.4765(13) 0.6672(3) 0.038(2) Uani 1 1 d . . . H17A H 0.7532 0.4380 0.6499 0.045 Uiso 1 1 calc R . . C18 C 0.7163(7) 0.4407(12) 0.7052(2) 0.0278(18) Uani 1 1 d . . . H18A H 0.7750 0.3789 0.7137 0.033 Uiso 1 1 calc R . . Se21 Se 0.48650(5) 0.08975(10) 0.39021(2) 0.02171(17) Uani 1 1 d . . . Se22 Se 0.72650(5) -0.16280(9) 0.37102(2) 0.01883(16) Uani 1 1 d . . . P21 P 0.64192(13) 0.0269(2) 0.40328(5) 0.0165(4) Uani 1 1 d . . . C22 C 0.7111(5) 0.2475(9) 0.3989(2) 0.0168(15) Uani 1 1 d . . . N22 N 0.6581(5) 0.3973(8) 0.3985(2) 0.0235(15) Uani 1 1 d D . . H22A H 0.593(5) 0.374(16) 0.386(3) 0.08(4) Uiso 1 1 d D . . H22B H 0.684(6) 0.520(4) 0.400(2) 0.03(2) Uiso 1 1 d D . . N23 N 0.8115(4) 0.2424(8) 0.39923(19) 0.0195(13) Uani 1 1 d D . . H23N H 0.845(4) 0.125(4) 0.3984(18) 0.000(15) Uiso 1 1 d D . . C24 C 0.8787(6) 0.3993(10) 0.4026(2) 0.0210(16) Uani 1 1 d . . . H24A H 0.8548 0.4943 0.3854 0.025 Uiso 1 1 calc R . . H24B H 0.9483 0.3648 0.3949 0.025 Uiso 1 1 calc R . . C25 C 0.8822(7) 0.4739(9) 0.4422(2) 0.0274(18) Uani 1 1 d . . . H25A H 0.8127 0.5104 0.4496 0.033 Uiso 1 1 calc R . . H25B H 0.9253 0.5829 0.4423 0.033 Uiso 1 1 calc R . . C26 C 0.9236(7) 0.3418(11) 0.4715(2) 0.0311(19) Uani 1 1 d . . . H26A H 0.8866 0.2266 0.4694 0.037 Uiso 1 1 calc R . . H26B H 0.9964 0.3183 0.4664 0.037 Uiso 1 1 calc R . . C27 C 0.9122(7) 0.4141(11) 0.5107(2) 0.031(2) Uani 1 1 d . . . C28 C 0.9910(7) 0.4994(13) 0.5287(3) 0.034(2) Uani 1 1 d . . . H28A H 1.0562 0.5056 0.5174 0.041 Uiso 1 1 calc R . . C29 C 0.9747(8) 0.5776(13) 0.5641(3) 0.040(2) Uani 1 1 d . . . H29A H 1.0297 0.6354 0.5764 0.048 Uiso 1 1 calc R . . C30 C 0.8824(9) 0.5724(14) 0.5810(3) 0.044(2) Uani 1 1 d . . . H30A H 0.8723 0.6285 0.6045 0.053 Uiso 1 1 calc R . . C31 C 0.8025(8) 0.4835(14) 0.5633(3) 0.041(2) Uani 1 1 d . . . H31A H 0.7379 0.4762 0.5751 0.049 Uiso 1 1 calc R . . C32 C 0.8173(7) 0.4060(12) 0.5286(3) 0.035(2) Uani 1 1 d . . . H32A H 0.7624 0.3462 0.5167 0.042 Uiso 1 1 calc R . . C33 C 0.6606(6) -0.0083(10) 0.4537(2) 0.0198(16) Uani 1 1 d . . . C34 C 0.7474(7) -0.0955(10) 0.4670(3) 0.0254(17) Uani 1 1 d . . . H34A H 0.7983 -0.1337 0.4500 0.031 Uiso 1 1 calc R . . C35 C 0.7598(8) -0.1268(12) 0.5049(3) 0.037(2) Uani 1 1 d . . . H35A H 0.8184 -0.1888 0.5135 0.044 Uiso 1 1 calc R . . C36 C 0.6883(8) -0.0692(13) 0.5303(2) 0.038(2) Uani 1 1 d . . . H36A H 0.6980 -0.0894 0.5562 0.046 Uiso 1 1 calc R . . C37 C 0.6010(8) 0.0196(13) 0.5175(3) 0.038(2) Uani 1 1 d . . . H37A H 0.5508 0.0588 0.5347 0.045 Uiso 1 1 calc R . . C38 C 0.5882(7) 0.0501(12) 0.4794(2) 0.0280(18) Uani 1 1 d . . . H38A H 0.5294 0.1116 0.4708 0.034 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 0.0155(4) 0.0192(3) 0.0301(4) 0.0005(3) -0.0027(3) -0.0002(3) Se2 0.0194(3) 0.0129(3) 0.0214(4) -0.0020(3) -0.0013(3) 0.0008(3) P1 0.0170(9) 0.0121(8) 0.0205(9) -0.0002(7) 0.0000(7) -0.0011(7) C2 0.015(3) 0.013(3) 0.018(4) 0.000(3) 0.004(3) 0.001(3) N2 0.018(3) 0.021(3) 0.040(4) 0.003(3) 0.001(3) 0.000(2) N3 0.022(3) 0.018(3) 0.020(3) -0.001(3) 0.000(2) -0.001(2) C4 0.022(4) 0.016(3) 0.027(4) 0.003(3) 0.005(3) -0.004(3) C5 0.023(4) 0.022(4) 0.021(4) -0.007(3) -0.003(3) 0.002(3) C6 0.038(5) 0.021(4) 0.037(5) -0.005(4) -0.012(4) -0.003(3) C7 0.030(4) 0.019(4) 0.029(4) 0.004(3) -0.008(3) 0.001(3) C8 0.041(6) 0.038(5) 0.029(5) 0.000(4) -0.001(4) -0.007(4) C9 0.050(6) 0.039(5) 0.035(5) -0.004(4) -0.009(4) -0.003(5) C10 0.065(7) 0.026(4) 0.023(5) 0.001(4) -0.003(4) -0.002(4) C11 0.039(5) 0.033(5) 0.035(5) 0.007(4) 0.006(4) 0.005(4) C12 0.033(5) 0.028(5) 0.036(5) 0.007(4) -0.007(4) -0.004(3) C13 0.019(4) 0.018(3) 0.022(4) 0.000(3) -0.003(3) -0.002(3) C14 0.028(4) 0.032(4) 0.021(4) 0.002(3) 0.000(3) 0.003(4) C15 0.045(6) 0.035(5) 0.030(5) 0.004(4) -0.008(4) 0.006(4) C16 0.056(6) 0.030(4) 0.021(4) 0.003(4) -0.004(4) -0.005(4) C17 0.041(5) 0.042(5) 0.031(5) -0.003(4) 0.011(4) 0.001(4) C18 0.032(5) 0.027(4) 0.025(4) -0.004(4) 0.006(4) -0.002(3) Se21 0.0142(4) 0.0208(4) 0.0301(4) 0.0045(3) -0.0019(3) 0.0008(3) Se22 0.0210(4) 0.0139(3) 0.0216(4) -0.0015(3) 0.0002(3) 0.0016(3) P21 0.0143(8) 0.0138(9) 0.0214(9) 0.0015(7) 0.0009(7) 0.0000(7) C22 0.016(3) 0.017(3) 0.016(4) 0.002(3) 0.002(3) 0.000(3) N22 0.025(3) 0.008(3) 0.037(4) 0.002(3) 0.000(3) 0.001(2) N23 0.018(3) 0.013(3) 0.028(4) -0.001(3) 0.005(2) -0.004(2) C24 0.022(4) 0.019(4) 0.022(4) 0.003(3) -0.001(3) -0.006(3) C25 0.035(5) 0.011(3) 0.037(5) 0.003(3) 0.002(4) -0.006(3) C26 0.043(5) 0.024(4) 0.027(4) 0.000(3) 0.000(4) 0.008(4) C27 0.043(5) 0.024(4) 0.025(4) 0.005(3) -0.008(4) -0.002(4) C28 0.025(5) 0.037(5) 0.040(5) 0.000(4) -0.012(4) -0.007(4) C29 0.045(6) 0.031(5) 0.043(6) 0.002(4) -0.014(5) -0.006(4) C30 0.065(7) 0.042(5) 0.025(5) 0.005(4) 0.000(5) 0.003(5) C31 0.046(6) 0.045(6) 0.031(5) 0.014(4) 0.008(4) -0.006(5) C32 0.034(5) 0.027(5) 0.043(6) 0.005(4) -0.003(4) -0.005(4) C33 0.027(4) 0.013(3) 0.020(4) 0.004(3) 0.003(3) 0.001(3) C34 0.027(4) 0.017(4) 0.032(5) 0.001(3) -0.002(3) 0.001(3) C35 0.047(6) 0.033(4) 0.030(5) 0.012(4) -0.009(4) 0.006(4) C36 0.058(6) 0.037(5) 0.019(4) 0.004(4) -0.003(4) 0.001(5) C37 0.052(6) 0.038(5) 0.024(5) -0.005(4) 0.010(4) 0.000(5) C38 0.027(4) 0.032(4) 0.025(4) 0.002(4) 0.004(4) 0.007(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 P1 2.142(2) . ? Se2 P1 2.147(2) . ? P1 C13 1.851(8) . ? P1 C2 1.884(7) . ? C2 N3 1.307(9) . ? C2 N2 1.339(9) . ? N2 H2A 0.98(2) . ? N2 H2B 0.98(2) . ? N3 C4 1.475(9) . ? N3 H3N 0.98(6) . ? C4 C5 1.526(10) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.535(11) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.511(12) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C12 1.391(12) . ? C7 C8 1.419(12) . ? C8 C9 1.367(14) . ? C8 H8A 0.9500 . ? C9 C10 1.414(15) . ? C9 H9A 0.9500 . ? C10 C11 1.378(14) . ? C10 H10A 0.9500 . ? C11 C12 1.398(14) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 C18 1.389(11) . ? C13 C14 1.392(11) . ? C14 C15 1.390(13) . ? C14 H14A 0.9500 . ? C15 C16 1.402(14) . ? C15 H15A 0.9500 . ? C16 C17 1.370(14) . ? C16 H16A 0.9500 . ? C17 C18 1.397(13) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? Se21 P21 2.1492(19) . ? Se22 P21 2.138(2) . ? P21 C33 1.842(8) . ? P21 C22 1.886(7) . ? C22 N22 1.316(9) . ? C22 N23 1.321(9) . ? N22 H22A 0.98(5) . ? N22 H22B 0.98(5) . ? N23 C24 1.471(9) . ? N23 H23N 0.98(5) . ? C24 C25 1.523(11) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.539(11) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C27 1.513(12) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.377(12) . ? C27 C32 1.404(13) . ? C28 C29 1.410(15) . ? C28 H28A 0.9500 . ? C29 C30 1.358(15) . ? C29 H29A 0.9500 . ? C30 C31 1.395(15) . ? C30 H30A 0.9500 . ? C31 C32 1.383(15) . ? C31 H31A 0.9500 . ? C32 H32A 0.9500 . ? C33 C38 1.394(11) . ? C33 C34 1.398(11) . ? C34 C35 1.387(13) . ? C34 H34A 0.9500 . ? C35 C36 1.376(14) . ? C35 H35A 0.9500 . ? C36 C37 1.402(14) . ? C36 H36A 0.9500 . ? C37 C38 1.394(13) . ? C37 H37A 0.9500 . ? C38 H38A 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 C13 P1 C2 99.4(3) . . ? C13 P1 Se1 112.0(2) . . ? C2 P1 Se1 105.9(2) . . ? C13 P1 Se2 111.4(2) . . ? C2 P1 Se2 104.7(2) . . ? Se1 P1 Se2 120.66(9) . . ? N3 C2 N2 123.8(6) . . ? N3 C2 P1 118.7(5) . . ? N2 C2 P1 117.4(5) . . ? C2 N2 H2A 110(4) . . ? C2 N2 H2B 122(6) . . ? H2A N2 H2B 122(7) . . ? C2 N3 C4 125.1(6) . . ? C2 N3 H3N 114(5) . . ? C4 N3 H3N 117(5) . . ? N3 C4 C5 111.0(6) . . ? N3 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? N3 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 114.0(6) . . ? C4 C5 H5A 108.7 . . ? C6 C5 H5A 108.7 . . ? C4 C5 H5B 108.7 . . ? C6 C5 H5B 108.7 . . ? H5A C5 H5B 107.6 . . ? C7 C6 C5 110.6(7) . . ? C7 C6 H6A 109.5 . . ? C5 C6 H6A 109.5 . . ? C7 C6 H6B 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C12 C7 C8 117.0(8) . . ? C12 C7 C6 121.6(8) . . ? C8 C7 C6 121.3(8) . . ? C9 C8 C7 121.6(9) . . ? C9 C8 H8A 119.2 . . ? C7 C8 H8A 119.2 . . ? C8 C9 C10 120.5(10) . . ? C8 C9 H9A 119.7 . . ? C10 C9 H9A 119.7 . . ? C11 C10 C9 118.5(9) . . ? C11 C10 H10A 120.8 . . ? C9 C10 H10A 120.8 . . ? C10 C11 C12 120.8(10) . . ? C10 C11 H11A 119.6 . . ? C12 C11 H11A 119.6 . . ? C7 C12 C11 121.5(9) . . ? C7 C12 H12A 119.3 . . ? C11 C12 H12A 119.3 . . ? C18 C13 C14 119.8(7) . . ? C18 C13 P1 120.6(6) . . ? C14 C13 P1 119.6(6) . . ? C15 C14 C13 121.1(8) . . ? C15 C14 H14A 119.4 . . ? C13 C14 H14A 119.4 . . ? C14 C15 C16 118.5(9) . . ? C14 C15 H15A 120.8 . . ? C16 C15 H15A 120.8 . . ? C17 C16 C15 120.4(9) . . ? C17 C16 H16A 119.8 . . ? C15 C16 H16A 119.8 . . ? C16 C17 C18 121.2(9) . . ? C16 C17 H17A 119.4 . . ? C18 C17 H17A 119.4 . . ? C13 C18 C17 119.0(8) . . ? C13 C18 H18A 120.5 . . ? C17 C18 H18A 120.5 . . ? C33 P21 C22 98.1(3) . . ? C33 P21 Se22 111.5(2) . . ? C22 P21 Se22 106.3(2) . . ? C33 P21 Se21 111.8(3) . . ? C22 P21 Se21 104.5(2) . . ? Se22 P21 Se21 121.44(9) . . ? N22 C22 N23 123.6(7) . . ? N22 C22 P21 119.1(5) . . ? N23 C22 P21 117.1(5) . . ? C22 N22 H22A 109(7) . . ? C22 N22 H22B 128(5) . . ? H22A N22 H22B 120(9) . . ? C22 N23 C24 125.3(6) . . ? C22 N23 H23N 119(4) . . ? C24 N23 H23N 116(4) . . ? N23 C24 C25 112.7(6) . . ? N23 C24 H24A 109.1 . . ? C25 C24 H24A 109.1 . . ? N23 C24 H24B 109.1 . . ? C25 C24 H24B 109.1 . . ? H24A C24 H24B 107.8 . . ? C24 C25 C26 114.3(6) . . ? C24 C25 H25A 108.7 . . ? C26 C25 H25A 108.7 . . ? C24 C25 H25B 108.7 . . ? C26 C25 H25B 108.7 . . ? H25A C25 H25B 107.6 . . ? C27 C26 C25 111.8(7) . . ? C27 C26 H26A 109.3 . . ? C25 C26 H26A 109.3 . . ? C27 C26 H26B 109.3 . . ? C25 C26 H26B 109.3 . . ? H26A C26 H26B 107.9 . . ? C28 C27 C32 118.4(9) . . ? C28 C27 C26 121.6(9) . . ? C32 C27 C26 119.8(8) . . ? C27 C28 C29 119.8(9) . . ? C27 C28 H28A 120.1 . . ? C29 C28 H28A 120.1 . . ? C30 C29 C28 121.6(9) . . ? C30 C29 H29A 119.2 . . ? C28 C29 H29A 119.2 . . ? C29 C30 C31 119.0(10) . . ? C29 C30 H30A 120.5 . . ? C31 C30 H30A 120.5 . . ? C32 C31 C30 120.0(10) . . ? C32 C31 H31A 120.0 . . ? C30 C31 H31A 120.0 . . ? C31 C32 C27 121.1(9) . . ? C31 C32 H32A 119.4 . . ? C27 C32 H32A 119.4 . . ? C38 C33 C34 118.5(7) . . ? C38 C33 P21 120.8(6) . . ? C34 C33 P21 120.6(6) . . ? C35 C34 C33 120.6(8) . . ? C35 C34 H34A 119.7 . . ? C33 C34 H34A 119.7 . . ? C36 C35 C34 120.9(9) . . ? C36 C35 H35A 119.6 . . ? C34 C35 H35A 119.6 . . ? C35 C36 C37 119.4(8) . . ? C35 C36 H36A 120.3 . . ? C37 C36 H36A 120.3 . . ? C38 C37 C36 119.7(9) . . ? C38 C37 H37A 120.1 . . ? C36 C37 H37A 120.1 . . ? C37 C38 C33 120.9(8) . . ? C37 C38 H38A 119.6 . . ? C33 C38 H38A 119.6 . . ? 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 C13 P1 C2 N3 -75.6(6) . . . . ? Se1 P1 C2 N3 168.2(5) . . . . ? Se2 P1 C2 N3 39.6(6) . . . . ? C13 P1 C2 N2 101.7(6) . . . . ? Se1 P1 C2 N2 -14.6(6) . . . . ? Se2 P1 C2 N2 -143.2(6) . . . . ? N2 C2 N3 C4 -10.3(12) . . . . ? P1 C2 N3 C4 166.8(6) . . . . ? C2 N3 C4 C5 -73.9(9) . . . . ? N3 C4 C5 C6 -63.6(9) . . . . ? C4 C5 C6 C7 173.2(7) . . . . ? C5 C6 C7 C12 -78.1(10) . . . . ? C5 C6 C7 C8 98.1(9) . . . . ? C12 C7 C8 C9 1.2(13) . . . . ? C6 C7 C8 C9 -175.1(8) . . . . ? C7 C8 C9 C10 0.6(15) . . . . ? C8 C9 C10 C11 -1.8(14) . . . . ? C9 C10 C11 C12 1.2(14) . . . . ? C8 C7 C12 C11 -1.8(13) . . . . ? C6 C7 C12 C11 174.5(8) . . . . ? C10 C11 C12 C7 0.6(14) . . . . ? C2 P1 C13 C18 -95.7(7) . . . . ? Se1 P1 C13 C18 15.8(7) . . . . ? Se2 P1 C13 C18 154.3(6) . . . . ? C2 P1 C13 C14 85.6(7) . . . . ? Se1 P1 C13 C14 -162.8(6) . . . . ? Se2 P1 C13 C14 -24.4(7) . . . . ? C18 C13 C14 C15 -0.7(13) . . . . ? P1 C13 C14 C15 177.9(7) . . . . ? C13 C14 C15 C16 -1.0(14) . . . . ? C14 C15 C16 C17 2.3(14) . . . . ? C15 C16 C17 C18 -2.0(14) . . . . ? C14 C13 C18 C17 1.1(13) . . . . ? P1 C13 C18 C17 -177.5(7) . . . . ? C16 C17 C18 C13 0.2(14) . . . . ? C33 P21 C22 N22 -99.0(7) . . . . ? Se22 P21 C22 N22 145.7(6) . . . . ? Se21 P21 C22 N22 16.1(7) . . . . ? C33 P21 C22 N23 76.3(6) . . . . ? Se22 P21 C22 N23 -39.0(6) . . . . ? Se21 P21 C22 N23 -168.6(5) . . . . ? N22 C22 N23 C24 6.0(12) . . . . ? P21 C22 N23 C24 -169.0(6) . . . . ? C22 N23 C24 C25 74.9(10) . . . . ? N23 C24 C25 C26 61.7(9) . . . . ? C24 C25 C26 C27 -172.3(7) . . . . ? C25 C26 C27 C28 -96.9(10) . . . . ? C25 C26 C27 C32 78.5(10) . . . . ? C32 C27 C28 C29 -0.7(13) . . . . ? C26 C27 C28 C29 174.8(8) . . . . ? C27 C28 C29 C30 -0.5(15) . . . . ? C28 C29 C30 C31 1.6(15) . . . . ? C29 C30 C31 C32 -1.5(15) . . . . ? C30 C31 C32 C27 0.3(14) . . . . ? C28 C27 C32 C31 0.8(13) . . . . ? C26 C27 C32 C31 -174.8(8) . . . . ? C22 P21 C33 C38 92.6(7) . . . . ? Se22 P21 C33 C38 -156.2(6) . . . . ? Se21 P21 C33 C38 -16.6(7) . . . . ? C22 P21 C33 C34 -87.9(6) . . . . ? Se22 P21 C33 C34 23.3(7) . . . . ? Se21 P21 C33 C34 162.9(6) . . . . ? C38 C33 C34 C35 1.5(12) . . . . ? P21 C33 C34 C35 -178.0(7) . . . . ? C33 C34 C35 C36 -1.5(14) . . . . ? C34 C35 C36 C37 1.1(15) . . . . ? C35 C36 C37 C38 -0.7(15) . . . . ? C36 C37 C38 C33 0.7(15) . . . . ? C34 C33 C38 C37 -1.2(13) . . . . ? P21 C33 C38 C37 178.4(7) . . . . ? 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 H2A Se1 0.98(6) 2.48(5) 3.234(6) 134(5) . N2 H2B Se2 0.98(5) 2.54(3) 3.483(6) 162(8) 1_545 N3 H3N Se2 0.98(5) 2.74(8) 3.363(6) 122(6) . N3 H3N Se1 0.98(5) 2.63(5) 3.479(6) 145(7) 3_465 N22 H22A Se21 0.98(5) 2.54(10) 3.231(6) 127(9) . N22 H22B Se22 0.98(5) 2.65(4) 3.540(6) 152(7) 1_565 N23 H23N Se22 0.98(5) 2.83(6) 3.375(6) 116(4) . N23 H23N Se21 0.98(5) 2.47(3) 3.396(6) 157(5) 3 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.461 _refine_diff_density_min -0.606 _refine_diff_density_rms 0.095