# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Frederic Leroux' _publ_contact_author_email FREDERIC.LEROUX@UNISTRA.FR _publ_section_title ; The [1,2,3]Triazolo[1,5-a]pyridine Ring: A Sensitive Sensor for the Electronic Profile of Phosphor(III) Substituents ; loop_ _publ_author_name 'Frederic Leroux' 'Belen Abarca' 'Rafael Ballesteros-Garrido' 'Laurence Bonnafoux' F.Colobert # Attachment 'compound_2d.cif' data_colo29 _database_code_depnum_ccdc_archive 'CCDC 705762' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H17 N4 P' _chemical_formula_sum 'C23 H17 N4 P' _chemical_formula_weight 380.38 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 13.3540(8) _cell_length_b 14.4253(4) _cell_length_c 19.6452(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3784.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8814 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16637 _diffrn_reflns_av_R_equivalents 0.0724 _diffrn_reflns_av_sigmaI/netI 0.0794 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4321 _reflns_number_gt 2533 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0964P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0064(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4321 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1176 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1781 _refine_ls_wR_factor_gt 0.1334 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 C1 C 0.2917(2) 0.3962(2) 0.63462(15) 0.0445(7) Uani 1 1 d . . . H1 H 0.2829 0.4109 0.6814 0.053 Uiso 1 1 calc R . . C2 C 0.2707(2) 0.31117(19) 0.61084(15) 0.0459(8) Uani 1 1 d . . . H2 H 0.2462 0.2652 0.6412 0.055 Uiso 1 1 calc R . . C3 C 0.2843(2) 0.28902(18) 0.54184(15) 0.0422(7) Uani 1 1 d . . . H3 H 0.2695 0.2282 0.5262 0.051 Uiso 1 1 calc R . . C4 C 0.3184(2) 0.35348(16) 0.49725(14) 0.0350(7) Uani 1 1 d . . . H4 H 0.3280 0.3383 0.4507 0.042 Uiso 1 1 calc R . . C5 C 0.33937(19) 0.44364(16) 0.52139(13) 0.0300(6) Uani 1 1 d . . . C6 C 0.3724(2) 0.52895(16) 0.49557(13) 0.0306(6) Uani 1 1 d . . . C7 C 0.3990(2) 0.55390(16) 0.42598(13) 0.0288(6) Uani 1 1 d . . . C8 C 0.4414(2) 0.63897(16) 0.40926(14) 0.0354(7) Uani 1 1 d . . . H8 H 0.4536 0.6842 0.4434 0.042 Uiso 1 1 calc R . . C9 C 0.4653(2) 0.65633(17) 0.34235(15) 0.0402(7) Uani 1 1 d . . . H9 H 0.4940 0.7141 0.3298 0.048 Uiso 1 1 calc R . . C10 C 0.4473(2) 0.58907(16) 0.29312(15) 0.0375(7) Uani 1 1 d . . . H10 H 0.4648 0.5995 0.2469 0.045 Uiso 1 1 calc R . . C11 C 0.4029(2) 0.50588(16) 0.31341(13) 0.0312(6) Uani 1 1 d . . . C12 C 0.3848(2) 0.31085(16) 0.30077(13) 0.0306(6) Uani 1 1 d . . . C13 C 0.3125(2) 0.24143(17) 0.30123(13) 0.0380(7) Uani 1 1 d . . . H13 H 0.2513 0.2502 0.2773 0.046 Uiso 1 1 calc R . . C14 C 0.3294(3) 0.15884(18) 0.33672(14) 0.0446(8) Uani 1 1 d . . . H14 H 0.2805 0.1110 0.3359 0.054 Uiso 1 1 calc R . . C15 C 0.4170(3) 0.14667(17) 0.37289(14) 0.0419(8) Uani 1 1 d . . . H15 H 0.4282 0.0906 0.3970 0.050 Uiso 1 1 calc R . . C16 C 0.4882(2) 0.21564(17) 0.37407(14) 0.0400(7) Uani 1 1 d . . . H16 H 0.5479 0.2075 0.3997 0.048 Uiso 1 1 calc R . . C17 C 0.4731(2) 0.29699(16) 0.33797(14) 0.0347(7) Uani 1 1 d . . . H17 H 0.5232 0.3438 0.3384 0.042 Uiso 1 1 calc R . . C18 C 0.4487(2) 0.41595(15) 0.18499(13) 0.0307(6) Uani 1 1 d . . . C19 C 0.4092(2) 0.40861(17) 0.11937(13) 0.0356(7) Uani 1 1 d . . . H19 H 0.3387 0.4095 0.1131 0.043 Uiso 1 1 calc R . . C20 C 0.4709(2) 0.40008(19) 0.06368(15) 0.0428(7) Uani 1 1 d . . . H20 H 0.4428 0.3948 0.0194 0.051 Uiso 1 1 calc R . . C21 C 0.5739(2) 0.39922(17) 0.07201(15) 0.0408(7) Uani 1 1 d . . . H21 H 0.6164 0.3932 0.0335 0.049 Uiso 1 1 calc R . . C22 C 0.6144(2) 0.40708(16) 0.13581(15) 0.0373(7) Uani 1 1 d . . . H22 H 0.6851 0.4067 0.1414 0.045 Uiso 1 1 calc R . . C23 C 0.5524(2) 0.41566(16) 0.19283(14) 0.0345(7) Uani 1 1 d . . . H23 H 0.5810 0.4213 0.2369 0.041 Uiso 1 1 calc R . . N1 N 0.32636(18) 0.46137(14) 0.58918(11) 0.0346(5) Uani 1 1 d . . . N2 N 0.35066(19) 0.55064(16) 0.60527(12) 0.0412(6) Uani 1 1 d . . . N3 N 0.37766(17) 0.59021(14) 0.54793(12) 0.0367(6) Uani 1 1 d . . . N4 N 0.37844(17) 0.48871(13) 0.37881(10) 0.0293(5) Uani 1 1 d . . . P1 P 0.35641(6) 0.41764(4) 0.25394(3) 0.0322(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0382(18) 0.0616(19) 0.0336(16) 0.0098(14) 0.0079(15) 0.0025(15) C2 0.044(2) 0.0508(18) 0.0430(18) 0.0161(14) 0.0055(16) -0.0017(15) C3 0.0424(19) 0.0372(14) 0.0472(18) 0.0092(13) -0.0046(16) -0.0016(13) C4 0.0356(16) 0.0348(14) 0.0346(15) 0.0013(11) -0.0046(13) 0.0000(12) C5 0.0254(15) 0.0362(14) 0.0283(14) 0.0023(11) -0.0018(12) 0.0048(11) C6 0.0284(15) 0.0313(13) 0.0321(15) -0.0040(11) -0.0023(12) 0.0032(11) C7 0.0251(14) 0.0273(13) 0.0341(15) -0.0001(11) -0.0038(12) 0.0037(11) C8 0.0364(17) 0.0287(14) 0.0410(16) -0.0010(11) 0.0006(14) 0.0013(12) C9 0.0376(18) 0.0249(13) 0.058(2) 0.0068(13) 0.0038(16) -0.0013(12) C10 0.0421(18) 0.0312(14) 0.0391(16) 0.0076(11) 0.0085(14) 0.0041(12) C11 0.0315(16) 0.0270(13) 0.0351(15) 0.0031(11) 0.0038(13) 0.0066(11) C12 0.0366(16) 0.0284(13) 0.0269(14) -0.0036(10) 0.0054(13) -0.0018(11) C13 0.0401(18) 0.0430(15) 0.0310(15) -0.0045(12) 0.0023(14) -0.0077(13) C14 0.058(2) 0.0343(15) 0.0416(17) 0.0002(12) 0.0087(17) -0.0156(14) C15 0.064(2) 0.0272(13) 0.0347(16) 0.0004(11) 0.0032(16) -0.0018(14) C16 0.0484(19) 0.0366(15) 0.0350(16) -0.0028(12) -0.0024(15) 0.0033(13) C17 0.0400(18) 0.0285(13) 0.0356(16) 0.0015(11) -0.0016(14) -0.0042(12) C18 0.0334(16) 0.0262(12) 0.0324(15) 0.0016(10) 0.0012(13) 0.0000(11) C19 0.0328(16) 0.0441(15) 0.0299(15) -0.0006(11) -0.0009(13) 0.0004(12) C20 0.046(2) 0.0522(17) 0.0303(15) -0.0036(12) -0.0001(15) 0.0006(14) C21 0.049(2) 0.0363(15) 0.0369(17) -0.0032(12) 0.0128(16) 0.0032(13) C22 0.0320(16) 0.0314(14) 0.0485(18) 0.0023(12) 0.0031(14) 0.0013(12) C23 0.0383(17) 0.0322(13) 0.0328(15) 0.0038(11) -0.0021(14) 0.0012(12) N1 0.0326(14) 0.0419(12) 0.0292(13) -0.0003(10) 0.0021(11) 0.0010(10) N2 0.0408(15) 0.0473(14) 0.0356(14) -0.0082(11) 0.0047(12) 0.0001(12) N3 0.0345(14) 0.0396(12) 0.0360(14) -0.0054(10) 0.0005(11) 0.0015(10) N4 0.0329(14) 0.0256(10) 0.0295(12) 0.0009(9) 0.0012(11) 0.0023(9) P1 0.0329(4) 0.0351(4) 0.0287(4) 0.0015(3) 0.0018(3) 0.0011(3) _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 C1 C2 1.342(4) . ? C1 N1 1.377(3) . ? C1 H1 0.9500 . ? C2 C3 1.405(4) . ? C2 H2 0.9500 . ? C3 C4 1.356(4) . ? C3 H3 0.9500 . ? C4 C5 1.412(3) . ? C4 H4 0.9500 . ? C5 N1 1.367(3) . ? C5 C6 1.402(3) . ? C6 N3 1.358(3) . ? C6 C7 1.458(4) . ? C7 N4 1.348(3) . ? C7 C8 1.391(3) . ? C8 C9 1.376(4) . ? C8 H8 0.9500 . ? C9 C10 1.391(4) . ? C9 H9 0.9500 . ? C10 C11 1.396(3) . ? C10 H10 0.9500 . ? C11 N4 1.349(3) . ? C11 P1 1.836(3) . ? C12 C13 1.392(4) . ? C12 C17 1.401(4) . ? C12 P1 1.834(3) . ? C13 C14 1.399(4) . ? C13 H13 0.9500 . ? C14 C15 1.380(4) . ? C14 H14 0.9500 . ? C15 C16 1.377(4) . ? C15 H15 0.9500 . ? C16 C17 1.386(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C23 1.394(4) . ? C18 C19 1.397(4) . ? C18 P1 1.831(3) . ? C19 C20 1.374(4) . ? C19 H19 0.9500 . ? C20 C21 1.385(4) . ? C20 H20 0.9500 . ? C21 C22 1.370(4) . ? C21 H21 0.9500 . ? C22 C23 1.398(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? N1 N2 1.365(3) . ? N2 N3 1.313(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 C2 C1 N1 117.9(3) . . ? C2 C1 H1 121.0 . . ? N1 C1 H1 121.0 . . ? C1 C2 C3 121.1(3) . . ? C1 C2 H2 119.4 . . ? C3 C2 H2 119.4 . . ? C4 C3 C2 120.7(3) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 118.8(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 C6 103.2(2) . . ? N1 C5 C4 118.3(2) . . ? C6 C5 C4 138.5(2) . . ? N3 C6 C5 108.3(2) . . ? N3 C6 C7 122.5(2) . . ? C5 C6 C7 129.2(2) . . ? N4 C7 C8 122.4(2) . . ? N4 C7 C6 115.0(2) . . ? C8 C7 C6 122.6(2) . . ? C9 C8 C7 118.7(2) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 119.8(2) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C9 C10 C11 118.3(3) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? N4 C11 C10 122.2(2) . . ? N4 C11 P1 113.37(18) . . ? C10 C11 P1 123.9(2) . . ? C13 C12 C17 118.6(2) . . ? C13 C12 P1 117.6(2) . . ? C17 C12 P1 123.75(19) . . ? C12 C13 C14 120.2(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 120.2(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 120.2(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C12 120.6(2) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? C23 C18 C19 118.5(3) . . ? C23 C18 P1 125.9(2) . . ? C19 C18 P1 115.5(2) . . ? C20 C19 C18 121.1(3) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C21 120.1(3) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C22 C21 C20 120.0(3) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 120.4(3) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C18 C23 C22 120.0(3) . . ? C18 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? N2 N1 C5 111.8(2) . . ? N2 N1 C1 125.0(2) . . ? C5 N1 C1 123.1(2) . . ? N3 N2 N1 106.1(2) . . ? N2 N3 C6 110.6(2) . . ? C7 N4 C11 118.5(2) . . ? C18 P1 C12 102.74(11) . . ? C18 P1 C11 104.60(12) . . ? C12 P1 C11 101.13(11) . . ? 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 N1 C1 C2 C3 0.4(5) . . . . ? C1 C2 C3 C4 -0.5(5) . . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? C3 C4 C5 N1 1.4(4) . . . . ? C3 C4 C5 C6 -178.6(3) . . . . ? N1 C5 C6 N3 0.5(3) . . . . ? C4 C5 C6 N3 -179.6(3) . . . . ? N1 C5 C6 C7 179.9(3) . . . . ? C4 C5 C6 C7 -0.1(5) . . . . ? N3 C6 C7 N4 -172.5(2) . . . . ? C5 C6 C7 N4 8.1(4) . . . . ? N3 C6 C7 C8 6.8(4) . . . . ? C5 C6 C7 C8 -172.6(3) . . . . ? N4 C7 C8 C9 -1.5(4) . . . . ? C6 C7 C8 C9 179.2(3) . . . . ? C7 C8 C9 C10 -0.3(4) . . . . ? C8 C9 C10 C11 1.4(4) . . . . ? C9 C10 C11 N4 -0.8(4) . . . . ? C9 C10 C11 P1 170.2(2) . . . . ? C17 C12 C13 C14 -1.7(4) . . . . ? P1 C12 C13 C14 -179.3(2) . . . . ? C12 C13 C14 C15 1.6(4) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? C14 C15 C16 C17 -1.2(4) . . . . ? C15 C16 C17 C12 1.0(4) . . . . ? C13 C12 C17 C16 0.4(4) . . . . ? P1 C12 C17 C16 177.8(2) . . . . ? C23 C18 C19 C20 0.8(4) . . . . ? P1 C18 C19 C20 -175.4(2) . . . . ? C18 C19 C20 C21 -0.4(4) . . . . ? C19 C20 C21 C22 -0.1(4) . . . . ? C20 C21 C22 C23 0.2(4) . . . . ? C19 C18 C23 C22 -0.7(3) . . . . ? P1 C18 C23 C22 175.05(18) . . . . ? C21 C22 C23 C18 0.2(4) . . . . ? C6 C5 N1 N2 -0.8(3) . . . . ? C4 C5 N1 N2 179.2(2) . . . . ? C6 C5 N1 C1 178.4(2) . . . . ? C4 C5 N1 C1 -1.5(4) . . . . ? C2 C1 N1 N2 179.8(3) . . . . ? C2 C1 N1 C5 0.6(4) . . . . ? C5 N1 N2 N3 0.9(3) . . . . ? C1 N1 N2 N3 -178.4(3) . . . . ? N1 N2 N3 C6 -0.6(3) . . . . ? C5 C6 N3 N2 0.1(3) . . . . ? C7 C6 N3 N2 -179.4(2) . . . . ? C8 C7 N4 C11 2.1(4) . . . . ? C6 C7 N4 C11 -178.6(2) . . . . ? C10 C11 N4 C7 -0.9(4) . . . . ? P1 C11 N4 C7 -172.77(18) . . . . ? C23 C18 P1 C12 -60.1(2) . . . . ? C19 C18 P1 C12 115.75(19) . . . . ? C23 C18 P1 C11 45.1(2) . . . . ? C19 C18 P1 C11 -138.98(18) . . . . ? C13 C12 P1 C18 -114.6(2) . . . . ? C17 C12 P1 C18 67.9(2) . . . . ? C13 C12 P1 C11 137.4(2) . . . . ? C17 C12 P1 C11 -40.0(3) . . . . ? N4 C11 P1 C18 -149.50(19) . . . . ? C10 C11 P1 C18 38.8(3) . . . . ? N4 C11 P1 C12 -43.0(2) . . . . ? C10 C11 P1 C12 145.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.473 _refine_diff_density_min -0.527 _refine_diff_density_rms 0.141 # Attachment 'compound_3e.cif' data_colo31 _database_code_depnum_ccdc_archive 'CCDC 705763' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H21 N4 P Se' _chemical_formula_sum 'C25 H21 N4 P Se' _chemical_formula_weight 487.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6696(8) _cell_length_b 11.0202(11) _cell_length_c 12.2054(15) _cell_angle_alpha 88.075(6) _cell_angle_beta 87.392(6) _cell_angle_gamma 72.639(6) _cell_volume 1111.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13838 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.456 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 1.781 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72416 _exptl_absorpt_correction_T_max 0.84602 _exptl_absorpt_process_details 'MULscanABS in PLATON (Spek, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10682 _diffrn_reflns_av_R_equivalents 0.0792 _diffrn_reflns_av_sigmaI/netI 0.1465 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.64 _reflns_number_total 5065 _reflns_number_gt 2903 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1130P)^2^+2.7079P] 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 5065 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1729 _refine_ls_R_factor_gt 0.0924 _refine_ls_wR_factor_ref 0.2628 _refine_ls_wR_factor_gt 0.2108 _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 C1 C 0.6687(10) -0.2313(7) -0.0289(8) 0.041(2) Uani 1 1 d . . . H1 H 0.6735 -0.2967 -0.0788 0.049 Uiso 1 1 calc R . . C2 C 0.6005(10) -0.2332(7) 0.0724(8) 0.043(2) Uani 1 1 d . . . H2 H 0.5573 -0.3003 0.0945 0.052 Uiso 1 1 calc R . . C3 C 0.5939(10) -0.1366(7) 0.1442(7) 0.0383(19) Uani 1 1 d . . . H3 H 0.5455 -0.1388 0.2154 0.046 Uiso 1 1 calc R . . C4 C 0.6540(9) -0.0399(7) 0.1162(6) 0.0303(17) Uani 1 1 d . . . H4 H 0.6494 0.0247 0.1669 0.036 Uiso 1 1 calc R . . C5 C 0.7245(8) -0.0369(6) 0.0090(6) 0.0278(17) Uani 1 1 d . . . C6 C 0.7978(8) 0.0405(6) -0.0533(6) 0.0253(16) Uani 1 1 d . . . C7 C 0.8244(8) 0.1601(7) -0.0289(6) 0.0279(17) Uani 1 1 d . . . C8 C 0.9074(9) 0.2210(7) -0.1025(6) 0.0308(17) Uani 1 1 d . . . H8 H 0.9495 0.1847 -0.1711 0.037 Uiso 1 1 calc R . . C9 C 0.9263(9) 0.3351(7) -0.0724(6) 0.0320(17) Uani 1 1 d . . . H9 H 0.9797 0.3796 -0.1214 0.038 Uiso 1 1 calc R . . C10 C 0.8677(9) 0.3845(7) 0.0288(6) 0.0311(17) Uani 1 1 d . . . H10 H 0.8835 0.4613 0.0518 0.037 Uiso 1 1 calc R . . C11 C 0.7848(8) 0.3186(6) 0.0963(6) 0.0249(16) Uani 1 1 d . . . C12 C 0.8150(8) 0.4679(6) 0.2812(6) 0.0247(15) Uani 1 1 d . . . C13 C 0.9782(9) 0.4065(7) 0.2901(6) 0.0300(17) Uani 1 1 d . . . H13 H 1.0227 0.3221 0.2649 0.036 Uiso 1 1 calc R . . C14 C 1.0746(10) 0.4666(7) 0.3347(6) 0.0338(18) Uani 1 1 d . . . H14 H 1.1862 0.4224 0.3414 0.041 Uiso 1 1 calc R . . C15 C 1.0160(10) 0.5918(7) 0.3716(6) 0.0329(18) Uani 1 1 d . . . C18 C 1.1258(11) 0.6564(8) 0.4200(7) 0.046(2) Uani 1 1 d . . . H18A H 1.0610 0.7310 0.4604 0.069 Uiso 1 1 calc R . . H18B H 1.1898 0.6834 0.3611 0.069 Uiso 1 1 calc R . . H18C H 1.1985 0.5972 0.4702 0.069 Uiso 1 1 calc R . . C16 C 0.8540(10) 0.6507(7) 0.3611(7) 0.038(2) Uani 1 1 d . . . H16 H 0.8097 0.7354 0.3857 0.046 Uiso 1 1 calc R . . C17 C 0.7535(10) 0.5920(7) 0.3166(6) 0.0331(18) Uani 1 1 d . . . H17 H 0.6419 0.6362 0.3100 0.040 Uiso 1 1 calc R . . C19 C 0.6952(8) 0.2530(6) 0.3213(6) 0.0250(15) Uani 1 1 d . . . C20 C 0.8219(9) 0.1411(7) 0.3190(6) 0.0292(17) Uani 1 1 d . . . H20 H 0.9026 0.1278 0.2617 0.035 Uiso 1 1 calc R . . C21 C 0.8311(9) 0.0487(7) 0.3998(6) 0.0298(17) Uani 1 1 d . . . H21 H 0.9183 -0.0278 0.3967 0.036 Uiso 1 1 calc R . . C22 C 0.7153(9) 0.0649(7) 0.4863(6) 0.0322(18) Uani 1 1 d . . . C25 C 0.7301(11) -0.0331(8) 0.5759(7) 0.049(2) Uani 1 1 d . . . H25A H 0.7921 -0.1167 0.5482 0.073 Uiso 1 1 calc R . . H25B H 0.6221 -0.0353 0.6013 0.073 Uiso 1 1 calc R . . H25C H 0.7859 -0.0117 0.6371 0.073 Uiso 1 1 calc R . . C23 C 0.5894(9) 0.1778(8) 0.4867(7) 0.038(2) Uani 1 1 d . . . H23 H 0.5091 0.1908 0.5443 0.046 Uiso 1 1 calc R . . C24 C 0.5757(9) 0.2723(7) 0.4067(6) 0.0317(18) Uani 1 1 d . . . H24 H 0.4878 0.3483 0.4092 0.038 Uiso 1 1 calc R . . N1 N 0.7305(7) -0.1347(5) -0.0588(5) 0.0318(15) Uani 1 1 d . . . N2 N 0.8016(8) -0.1189(6) -0.1577(5) 0.0406(17) Uani 1 1 d . . . N3 N 0.8405(8) -0.0134(6) -0.1534(5) 0.0365(16) Uani 1 1 d . . . N4 N 0.7625(7) 0.2083(5) 0.0696(5) 0.0248(13) Uani 1 1 d . . . P1 P 0.6831(2) 0.38533(17) 0.22541(15) 0.0248(4) Uani 1 1 d . . . Se1 Se 0.44749(10) 0.50076(8) 0.19694(8) 0.0445(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.040(5) 0.024(4) 0.060(6) -0.008(4) -0.027(4) -0.006(4) C2 0.044(5) 0.029(4) 0.058(6) 0.007(4) -0.008(4) -0.012(4) C3 0.041(5) 0.037(4) 0.039(5) 0.005(4) -0.007(4) -0.014(4) C4 0.031(4) 0.027(4) 0.030(4) -0.002(3) -0.006(3) -0.005(3) C5 0.022(4) 0.023(4) 0.033(4) -0.005(3) -0.011(3) 0.002(3) C6 0.021(4) 0.025(4) 0.027(4) -0.003(3) -0.003(3) -0.003(3) C7 0.024(4) 0.027(4) 0.030(4) -0.005(3) -0.004(3) -0.003(3) C8 0.024(4) 0.041(4) 0.026(4) 0.000(3) -0.003(3) -0.007(3) C9 0.032(4) 0.038(4) 0.033(5) 0.009(3) -0.003(3) -0.023(3) C10 0.034(4) 0.030(4) 0.034(5) 0.002(3) -0.006(3) -0.016(3) C11 0.021(4) 0.025(4) 0.027(4) -0.001(3) -0.004(3) -0.004(3) C12 0.028(4) 0.025(4) 0.025(4) -0.001(3) -0.003(3) -0.013(3) C13 0.035(4) 0.023(4) 0.033(4) -0.001(3) -0.001(3) -0.010(3) C14 0.034(4) 0.033(4) 0.037(5) -0.001(3) -0.005(3) -0.014(3) C15 0.042(5) 0.036(4) 0.028(4) -0.002(3) -0.007(3) -0.022(4) C18 0.054(5) 0.050(5) 0.045(5) -0.010(4) -0.011(4) -0.031(4) C16 0.043(5) 0.031(4) 0.040(5) -0.017(4) -0.004(4) -0.008(4) C17 0.037(4) 0.026(4) 0.037(5) -0.009(3) 0.001(3) -0.009(3) C19 0.026(4) 0.029(4) 0.025(4) -0.006(3) -0.003(3) -0.016(3) C20 0.026(4) 0.034(4) 0.030(4) -0.009(3) 0.002(3) -0.011(3) C21 0.035(4) 0.023(4) 0.033(4) -0.001(3) -0.005(3) -0.012(3) C22 0.041(5) 0.042(4) 0.025(4) 0.001(3) -0.012(3) -0.028(4) C25 0.057(6) 0.052(5) 0.046(5) 0.008(4) -0.009(4) -0.030(5) C23 0.032(4) 0.057(5) 0.032(5) -0.010(4) 0.005(3) -0.024(4) C24 0.028(4) 0.034(4) 0.032(4) -0.002(3) 0.000(3) -0.008(3) N1 0.032(4) 0.025(3) 0.037(4) -0.008(3) -0.010(3) -0.006(3) N2 0.049(4) 0.036(4) 0.034(4) -0.013(3) -0.008(3) -0.006(3) N3 0.042(4) 0.033(4) 0.032(4) -0.014(3) 0.002(3) -0.006(3) N4 0.024(3) 0.024(3) 0.028(3) -0.002(2) -0.002(2) -0.010(3) P1 0.0230(9) 0.0232(9) 0.0300(11) -0.0045(7) -0.0029(8) -0.0087(8) Se1 0.0340(5) 0.0406(5) 0.0593(7) -0.0036(4) -0.0020(4) -0.0112(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 C1 C2 1.348(12) . ? C1 N1 1.361(10) . ? C1 H1 0.9500 . ? C2 C3 1.387(12) . ? C2 H2 0.9500 . ? C3 C4 1.347(11) . ? C3 H3 0.9500 . ? C4 C5 1.422(11) . ? C4 H4 0.9500 . ? C5 N1 1.368(9) . ? C5 C6 1.394(10) . ? C6 N3 1.363(9) . ? C6 C7 1.447(10) . ? C7 N4 1.353(9) . ? C7 C8 1.401(11) . ? C8 C9 1.379(11) . ? C8 H8 0.9500 . ? C9 C10 1.380(10) . ? C9 H9 0.9500 . ? C10 C11 1.393(10) . ? C10 H10 0.9500 . ? C11 N4 1.340(9) . ? C11 P1 1.834(7) . ? C12 C13 1.382(10) . ? C12 C17 1.388(10) . ? C12 P1 1.826(7) . ? C13 C14 1.353(11) . ? C13 H13 0.9500 . ? C14 C15 1.402(10) . ? C14 H14 0.9500 . ? C15 C16 1.371(11) . ? C15 C18 1.499(11) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C16 C17 1.369(11) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C19 C20 1.385(10) . ? C19 C24 1.410(10) . ? C19 P1 1.821(7) . ? C20 C21 1.381(10) . ? C20 H20 0.9500 . ? C21 C22 1.401(11) . ? C21 H21 0.9500 . ? C22 C23 1.389(11) . ? C22 C25 1.493(11) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C23 C24 1.386(11) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? N1 N2 1.359(9) . ? N2 N3 1.307(9) . ? P1 Se1 2.0965(19) . ? 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 C2 C1 N1 119.3(7) . . ? C2 C1 H1 120.4 . . ? N1 C1 H1 120.4 . . ? C1 C2 C3 119.6(8) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 122.1(8) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 118.5(7) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? N1 C5 C6 104.2(6) . . ? N1 C5 C4 117.6(7) . . ? C6 C5 C4 138.1(7) . . ? N3 C6 C5 107.5(6) . . ? N3 C6 C7 121.2(7) . . ? C5 C6 C7 131.2(6) . . ? N4 C7 C8 122.9(7) . . ? N4 C7 C6 114.9(6) . . ? C8 C7 C6 122.2(7) . . ? C9 C8 C7 118.1(7) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C8 C9 C10 120.0(7) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C11 118.1(7) . . ? C9 C10 H10 120.9 . . ? C11 C10 H10 120.9 . . ? N4 C11 C10 123.6(6) . . ? N4 C11 P1 114.9(5) . . ? C10 C11 P1 121.3(5) . . ? C13 C12 C17 118.9(7) . . ? C13 C12 P1 120.1(5) . . ? C17 C12 P1 120.9(6) . . ? C14 C13 C12 119.9(7) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 122.5(7) . . ? C13 C14 H14 118.8 . . ? C15 C14 H14 118.8 . . ? C16 C15 C14 116.4(7) . . ? C16 C15 C18 122.3(7) . . ? C14 C15 C18 121.3(7) . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C16 C15 122.4(7) . . ? C17 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? C16 C17 C12 119.9(7) . . ? C16 C17 H17 120.1 . . ? C12 C17 H17 120.1 . . ? C20 C19 C24 119.7(7) . . ? C20 C19 P1 123.1(6) . . ? C24 C19 P1 117.0(5) . . ? C21 C20 C19 120.2(7) . . ? C21 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? C20 C21 C22 121.7(7) . . ? C20 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C23 C22 C21 117.0(7) . . ? C23 C22 C25 121.6(7) . . ? C21 C22 C25 121.3(7) . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C23 C22 122.9(7) . . ? C24 C23 H23 118.6 . . ? C22 C23 H23 118.6 . . ? C23 C24 C19 118.5(7) . . ? C23 C24 H24 120.7 . . ? C19 C24 H24 120.7 . . ? N2 N1 C1 126.3(7) . . ? N2 N1 C5 110.8(6) . . ? C1 N1 C5 122.9(7) . . ? N3 N2 N1 106.8(6) . . ? N2 N3 C6 110.6(6) . . ? C11 N4 C7 117.2(6) . . ? C19 P1 C12 104.2(3) . . ? C19 P1 C11 107.4(3) . . ? C12 P1 C11 105.0(3) . . ? C19 P1 Se1 114.6(2) . . ? C12 P1 Se1 114.7(2) . . ? C11 P1 Se1 110.3(2) . . ? 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 N1 C1 C2 C3 0.2(12) . . . . ? C1 C2 C3 C4 -0.1(12) . . . . ? C2 C3 C4 C5 0.8(11) . . . . ? C3 C4 C5 N1 -1.5(10) . . . . ? C3 C4 C5 C6 179.8(8) . . . . ? N1 C5 C6 N3 0.9(7) . . . . ? C4 C5 C6 N3 179.6(8) . . . . ? N1 C5 C6 C7 178.0(7) . . . . ? C4 C5 C6 C7 -3.2(14) . . . . ? N3 C6 C7 N4 174.0(6) . . . . ? C5 C6 C7 N4 -2.8(11) . . . . ? N3 C6 C7 C8 -5.7(10) . . . . ? C5 C6 C7 C8 177.5(7) . . . . ? N4 C7 C8 C9 0.0(10) . . . . ? C6 C7 C8 C9 179.7(7) . . . . ? C7 C8 C9 C10 1.6(11) . . . . ? C8 C9 C10 C11 -2.4(11) . . . . ? C9 C10 C11 N4 1.8(11) . . . . ? C9 C10 C11 P1 -173.1(5) . . . . ? C17 C12 C13 C14 1.2(11) . . . . ? P1 C12 C13 C14 -177.9(6) . . . . ? C12 C13 C14 C15 -1.1(12) . . . . ? C13 C14 C15 C16 0.6(12) . . . . ? C13 C14 C15 C18 -179.5(8) . . . . ? C14 C15 C16 C17 -0.4(12) . . . . ? C18 C15 C16 C17 179.8(8) . . . . ? C15 C16 C17 C12 0.6(13) . . . . ? C13 C12 C17 C16 -1.0(11) . . . . ? P1 C12 C17 C16 178.1(6) . . . . ? C24 C19 C20 C21 0.1(11) . . . . ? P1 C19 C20 C21 174.4(6) . . . . ? C19 C20 C21 C22 -0.5(11) . . . . ? C20 C21 C22 C23 0.6(11) . . . . ? C20 C21 C22 C25 -177.3(7) . . . . ? C21 C22 C23 C24 -0.2(11) . . . . ? C25 C22 C23 C24 177.7(8) . . . . ? C22 C23 C24 C19 -0.2(12) . . . . ? C20 C19 C24 C23 0.3(11) . . . . ? P1 C19 C24 C23 -174.4(6) . . . . ? C2 C1 N1 N2 -179.5(7) . . . . ? C2 C1 N1 C5 -1.1(11) . . . . ? C6 C5 N1 N2 -0.6(7) . . . . ? C4 C5 N1 N2 -179.6(6) . . . . ? C6 C5 N1 C1 -179.2(6) . . . . ? C4 C5 N1 C1 1.7(10) . . . . ? C1 N1 N2 N3 178.6(6) . . . . ? C5 N1 N2 N3 0.0(8) . . . . ? N1 N2 N3 C6 0.5(8) . . . . ? C5 C6 N3 N2 -0.9(8) . . . . ? C7 C6 N3 N2 -178.4(6) . . . . ? C10 C11 N4 C7 -0.2(10) . . . . ? P1 C11 N4 C7 175.0(5) . . . . ? C8 C7 N4 C11 -0.7(10) . . . . ? C6 C7 N4 C11 179.6(6) . . . . ? C20 C19 P1 C12 -80.7(6) . . . . ? C24 C19 P1 C12 93.8(6) . . . . ? C20 C19 P1 C11 30.3(7) . . . . ? C24 C19 P1 C11 -155.2(6) . . . . ? C20 C19 P1 Se1 153.2(5) . . . . ? C24 C19 P1 Se1 -32.4(6) . . . . ? C13 C12 P1 C19 62.3(6) . . . . ? C17 C12 P1 C19 -116.7(6) . . . . ? C13 C12 P1 C11 -50.4(7) . . . . ? C17 C12 P1 C11 130.5(6) . . . . ? C13 C12 P1 Se1 -171.6(5) . . . . ? C17 C12 P1 Se1 9.4(7) . . . . ? N4 C11 P1 C19 37.3(6) . . . . ? C10 C11 P1 C19 -147.4(6) . . . . ? N4 C11 P1 C12 147.7(5) . . . . ? C10 C11 P1 C12 -36.9(6) . . . . ? N4 C11 P1 Se1 -88.3(5) . . . . ? C10 C11 P1 Se1 87.1(6) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.628 _refine_diff_density_min -0.882 _refine_diff_density_rms 0.180