# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Martyn Coles' _publ_contact_author_address ; Department of Chemistry University of Sussex Falmer Brighton BN1 9QJ UNITED KINGDOM ; _publ_contact_author_email M.P.COLES@SUSSEX.AC.UK _publ_section_title ; Self-organisation in P-substituted guanidines leading to solution-state isomerisation ; _publ_requested_category FO loop_ _publ_author_name 'Martyn Coles' 'Anthony G. Avent' 'Joanna Grundy' 'Peter B. Hitchcock' 'Natalie E. Mansfield' data_(2)-sep1203 _database_code_depnum_ccdc_archive 'CCDC 244048' _audit_creation_date 2003-09-16T11:39:47-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common (Ph2P(S)(C(Ncy)(NHcy))) _chemical_formula_moiety 'C25 H33 N2 P1 S1' _chemical_formula_sum 'C25 H33 N2 P1 S1' _chemical_formula_weight 424.56 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.3934(2) _cell_length_b 9.6078(2) _cell_length_c 17.3407(3) _cell_angle_alpha 90 _cell_angle_beta 100.495(1) _cell_angle_gamma 90 _cell_volume 2357.91(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 19926 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.394403E-1 _diffrn_orient_matrix_ub_12 -0.793557E-1 _diffrn_orient_matrix_ub_13 0.248378E-1 _diffrn_orient_matrix_ub_21 -0.47304E-1 _diffrn_orient_matrix_ub_22 -0.673292E-1 _diffrn_orient_matrix_ub_23 -0.282098E-1 _diffrn_orient_matrix_ub_31 0.346323E-1 _diffrn_orient_matrix_ub_32 -0.15919E-2 _diffrn_orient_matrix_ub_33 -0.450221E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_unetI/netI 0.0356 _diffrn_reflns_number 23714 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.93 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 4118 _reflns_number_gt 3539 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; The hydrogen on N1 was refined; other hydrogens were in riding mode. 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^)+(0.0288P)^2^+1.3403P] 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_number_reflns 4118 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0865 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.292 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 S S 0.44431(3) 0.32344(5) 0.29501(3) 0.03148(13) Uani 1 1 d . . . P P 0.35926(3) 0.30587(4) 0.19395(2) 0.02108(12) Uani 1 1 d . . . N1 N 0.27960(11) 0.10797(15) 0.26877(9) 0.0296(3) Uani 1 1 d . . . H1N H 0.3235(14) 0.147(2) 0.3040(11) 0.032(5) Uiso 1 1 d . . . N2 N 0.22439(10) 0.09262(14) 0.13599(8) 0.0263(3) Uani 1 1 d . . . C1 C 0.28955(11) 0.46074(17) 0.16769(9) 0.0235(4) Uani 1 1 d . . . C2 C 0.33773(12) 0.58687(17) 0.16610(10) 0.0266(4) Uani 1 1 d . . . H2 H 0.4048 0.5885 0.1781 0.032 Uiso 1 1 calc R . . C3 C 0.28839(13) 0.70896(18) 0.14712(10) 0.0308(4) Uani 1 1 d . . . H3 H 0.3215 0.7943 0.1459 0.037 Uiso 1 1 calc R . . C4 C 0.19074(13) 0.70705(19) 0.12993(12) 0.0376(5) Uani 1 1 d . . . H4 H 0.1567 0.791 0.1166 0.045 Uiso 1 1 calc R . . C5 C 0.14264(14) 0.5833(2) 0.13218(13) 0.0442(5) Uani 1 1 d . . . H5 H 0.0755 0.5825 0.1206 0.053 Uiso 1 1 calc R . . C6 C 0.19155(12) 0.46006(19) 0.15128(11) 0.0337(4) Uani 1 1 d . . . H6 H 0.158 0.3753 0.1531 0.04 Uiso 1 1 calc R . . C7 C 0.42440(11) 0.27271(17) 0.11584(9) 0.0216(3) Uani 1 1 d . . . C8 C 0.41453(12) 0.35193(17) 0.04770(9) 0.0254(4) Uani 1 1 d . . . H8 H 0.3711 0.4273 0.0397 0.03 Uiso 1 1 calc R . . C9 C 0.46861(12) 0.32017(19) -0.00862(10) 0.0311(4) Uani 1 1 d . . . H9 H 0.4623 0.3744 -0.0551 0.037 Uiso 1 1 calc R . . C10 C 0.53122(12) 0.2107(2) 0.00245(11) 0.0341(4) Uani 1 1 d . . . H10 H 0.5676 0.1893 -0.0365 0.041 Uiso 1 1 calc R . . C11 C 0.54142(12) 0.1316(2) 0.07002(11) 0.0336(4) Uani 1 1 d . . . H11 H 0.5847 0.056 0.0774 0.04 Uiso 1 1 calc R . . C12 C 0.48843(12) 0.16280(18) 0.12696(10) 0.0292(4) Uani 1 1 d . . . H12 H 0.4958 0.1091 0.1737 0.035 Uiso 1 1 calc R . . C13 C 0.27629(11) 0.15330(16) 0.19399(10) 0.0236(4) Uani 1 1 d . . . C14 C 0.22993(12) -0.01556(18) 0.28888(10) 0.0285(4) Uani 1 1 d . . . H14 H 0.2407 -0.0928 0.2529 0.034 Uiso 1 1 calc R . . C15 C 0.12381(13) 0.0082(2) 0.28009(11) 0.0365(4) Uani 1 1 d . . . H15A H 0.0971 0.0299 0.2247 0.044 Uiso 1 1 calc R . . H15B H 0.1119 0.0889 0.3125 0.044 Uiso 1 1 calc R . . C16 C 0.07500(14) -0.1209(2) 0.30566(13) 0.0464(5) Uani 1 1 d . . . H16A H 0.0067 -0.1018 0.3016 0.056 Uiso 1 1 calc R . . H16B H 0.082 -0.1992 0.2701 0.056 Uiso 1 1 calc R . . C17 C 0.11696(16) -0.1615(2) 0.38933(13) 0.0510(6) Uani 1 1 d . . . H17A H 0.1045 -0.0869 0.4255 0.061 Uiso 1 1 calc R . . H17B H 0.0863 -0.2478 0.4034 0.061 Uiso 1 1 calc R . . C18 C 0.22268(16) -0.1848(2) 0.39860(15) 0.0539(6) Uani 1 1 d . . . H18A H 0.2347 -0.2664 0.367 0.065 Uiso 1 1 calc R . . H18B H 0.249 -0.2052 0.4543 0.065 Uiso 1 1 calc R . . C19 C 0.27246(14) -0.0576(2) 0.37243(12) 0.0414(5) Uani 1 1 d . . . H19A H 0.2672 0.0211 0.4082 0.05 Uiso 1 1 calc R . . H19B H 0.3404 -0.0787 0.3757 0.05 Uiso 1 1 calc R . . C20 C 0.20940(11) 0.14525(17) 0.05572(9) 0.0235(4) Uani 1 1 d . . . H20 H 0.2357 0.2415 0.0554 0.028 Uiso 1 1 calc R . . C21 C 0.10293(12) 0.1485(2) 0.02534(11) 0.0350(4) Uani 1 1 d . . . H21A H 0.0765 0.0545 0.0304 0.042 Uiso 1 1 calc R . . H21B H 0.073 0.2131 0.058 0.042 Uiso 1 1 calc R . . C22 C 0.07906(14) 0.1946(2) -0.05997(12) 0.0448(5) Uani 1 1 d . . . H22A H 0.0098 0.1897 -0.0781 0.054 Uiso 1 1 calc R . . H22B H 0.0989 0.2926 -0.0642 0.054 Uiso 1 1 calc R . . C23 C 0.12795(15) 0.1038(2) -0.11217(11) 0.0446(5) Uani 1 1 d . . . H23A H 0.1016 0.0084 -0.1138 0.054 Uiso 1 1 calc R . . H23B H 0.1157 0.1414 -0.1662 0.054 Uiso 1 1 calc R . . C24 C 0.23369(13) 0.0983(2) -0.08211(10) 0.0360(4) Uani 1 1 d . . . H24A H 0.2611 0.1918 -0.0867 0.043 Uiso 1 1 calc R . . H24B H 0.263 0.0334 -0.115 0.043 Uiso 1 1 calc R . . C25 C 0.25646(12) 0.05085(18) 0.00318(10) 0.0282(4) Uani 1 1 d . . . H25A H 0.3258 0.0521 0.0214 0.034 Uiso 1 1 calc R . . H25B H 0.2342 -0.0459 0.0071 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 S 0.0365(3) 0.0303(3) 0.0265(2) -0.00183(18) 0.00253(19) -0.00186(19) P 0.0236(2) 0.0176(2) 0.0227(2) 0.00001(16) 0.00594(17) 0.00040(17) N1 0.0392(9) 0.0252(8) 0.0242(8) 0.0012(6) 0.0049(7) -0.0099(7) N2 0.0300(8) 0.0235(7) 0.0257(8) 0.0004(6) 0.0064(6) -0.0025(6) C1 0.0256(8) 0.0202(8) 0.0260(9) -0.0013(7) 0.0084(7) 0.0025(7) C2 0.0257(9) 0.0244(9) 0.0306(9) -0.0016(7) 0.0078(7) 0.0003(7) C3 0.0383(10) 0.0196(9) 0.0373(10) -0.0011(7) 0.0143(8) -0.0009(8) C4 0.0366(10) 0.0251(10) 0.0515(12) 0.0034(9) 0.0092(9) 0.0107(8) C5 0.0259(10) 0.0315(11) 0.0754(15) -0.0001(10) 0.0096(10) 0.0059(8) C6 0.0262(9) 0.0231(9) 0.0535(12) -0.0019(8) 0.0116(8) 0.0000(7) C7 0.0202(8) 0.0209(8) 0.0238(8) -0.0016(7) 0.0044(7) -0.0018(7) C8 0.0274(9) 0.0217(9) 0.0269(9) 0.0000(7) 0.0047(7) 0.0017(7) C9 0.0362(10) 0.0321(10) 0.0268(9) 0.0000(8) 0.0104(8) -0.0037(8) C10 0.0299(10) 0.0426(11) 0.0329(10) -0.0079(8) 0.0143(8) -0.0013(8) C11 0.0289(9) 0.0357(10) 0.0364(10) -0.0044(8) 0.0066(8) 0.0113(8) C12 0.0294(9) 0.0296(10) 0.0285(9) 0.0014(7) 0.0048(7) 0.0068(7) C13 0.0270(9) 0.0178(8) 0.0271(9) 0.0006(7) 0.0080(7) 0.0014(7) C14 0.0343(10) 0.0224(9) 0.0304(9) 0.0001(7) 0.0104(8) -0.0046(7) C15 0.0366(10) 0.0401(11) 0.0343(10) 0.0009(9) 0.0102(8) -0.0001(9) C16 0.0383(11) 0.0514(13) 0.0539(13) -0.0048(10) 0.0201(10) -0.0101(10) C17 0.0549(14) 0.0471(13) 0.0576(14) 0.0119(11) 0.0276(11) -0.0096(11) C18 0.0527(13) 0.0458(13) 0.0650(15) 0.0282(11) 0.0157(11) -0.0047(11) C19 0.0422(11) 0.0399(12) 0.0416(11) 0.0160(9) 0.0060(9) -0.0055(9) C20 0.0230(8) 0.0208(8) 0.0264(9) 0.0006(7) 0.0041(7) -0.0016(7) C21 0.0238(9) 0.0360(11) 0.0446(11) 0.0018(9) 0.0049(8) -0.0002(8) C22 0.0291(10) 0.0482(13) 0.0513(13) 0.0110(10) -0.0080(9) 0.0039(9) C23 0.0500(12) 0.0451(12) 0.0320(11) 0.0039(9) -0.0105(9) -0.0011(10) C24 0.0416(11) 0.0397(11) 0.0259(10) -0.0020(8) 0.0037(8) 0.0016(9) C25 0.0291(9) 0.0264(9) 0.0275(9) -0.0022(7) 0.0011(7) 0.0033(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 S P 1.9536(6) . ? P C1 1.8061(16) . ? P C7 1.8103(15) . ? P C13 1.8909(16) . ? N1 C13 1.361(2) . ? N1 C14 1.460(2) . ? N2 C13 1.279(2) . ? N2 C20 1.460(2) . ? C1 C6 1.387(2) . ? C1 C2 1.399(2) . ? C2 C3 1.380(2) . ? C3 C4 1.383(3) . ? C4 C5 1.380(3) . ? C5 C6 1.386(3) . ? C7 C8 1.391(2) . ? C7 C12 1.392(2) . ? C8 C9 1.389(2) . ? C9 C10 1.376(3) . ? C10 C11 1.381(3) . ? C11 C12 1.386(2) . ? C14 C19 1.521(3) . ? C14 C15 1.524(2) . ? C15 C16 1.530(3) . ? C16 C17 1.518(3) . ? C17 C18 1.517(3) . ? C18 C19 1.527(3) . ? C20 C21 1.527(2) . ? C20 C25 1.529(2) . ? C21 C22 1.522(3) . ? C22 C23 1.519(3) . ? C23 C24 1.517(3) . ? C24 C25 1.525(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P C7 107.22(7) . . ? C1 P C13 108.47(7) . . ? C7 P C13 106.09(7) . . ? C1 P S 112.55(6) . . ? C7 P S 111.17(6) . . ? C13 P S 111.05(6) . . ? C13 N1 C14 123.65(15) . . ? C13 N2 C20 123.76(14) . . ? C6 C1 C2 119.29(15) . . ? C6 C1 P 123.04(13) . . ? C2 C1 P 117.65(12) . . ? C3 C2 C1 120.38(16) . . ? C2 C3 C4 119.93(16) . . ? C5 C4 C3 120.05(17) . . ? C4 C5 C6 120.47(17) . . ? C5 C6 C1 119.87(17) . . ? C8 C7 C12 119.70(15) . . ? C8 C7 P 123.55(12) . . ? C12 C7 P 116.74(12) . . ? C9 C8 C7 119.57(16) . . ? C10 C9 C8 120.43(16) . . ? C9 C10 C11 120.30(15) . . ? C10 C11 C12 119.88(16) . . ? C11 C12 C7 120.12(16) . . ? N2 C13 N1 121.18(15) . . ? N2 C13 P 129.16(12) . . ? N1 C13 P 109.64(12) . . ? N1 C14 C19 108.28(15) . . ? N1 C14 C15 112.30(15) . . ? C19 C14 C15 110.93(14) . . ? C14 C15 C16 110.73(16) . . ? C17 C16 C15 111.21(17) . . ? C18 C17 C16 110.85(17) . . ? C17 C18 C19 111.49(18) . . ? C14 C19 C18 111.49(17) . . ? N2 C20 C21 107.50(13) . . ? N2 C20 C25 111.00(13) . . ? C21 C20 C25 109.41(14) . . ? C22 C21 C20 112.07(15) . . ? C23 C22 C21 111.40(16) . . ? C24 C23 C22 111.07(16) . . ? C23 C24 C25 111.62(15) . . ? C24 C25 C20 111.12(14) . . ? #===END data_(4)-oct2302 _database_code_depnum_ccdc_archive 'CCDC 244049' _audit_creation_date 2002-10-29T10:28:23-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_name_common (SePPh2C(NHC6H11)(NC6H11)) _chemical_formula_moiety 'C25 H33 N2 P1 Se1' _chemical_formula_sum 'C25 H33 N2 P Se' _chemical_formula_weight 471.46 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8687(1) _cell_length_b 9.6892(1) _cell_length_c 14.9910(2) _cell_angle_alpha 82.172(1) _cell_angle_beta 82.934(1) _cell_angle_gamma 69.345(1) _cell_volume 1190.24(2) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 8908 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 27.878 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.658 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.5757 _exptl_absorpt_correction_T_max 0.6174 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_unetI/netI 0.0281 _diffrn_reflns_number 15459 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.73 _diffrn_reflns_theta_max 27.88 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 5599 _reflns_number_gt 5129 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0117P)^2^+0.5539P] 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 'H on N1 refined; others riding' _refine_ls_extinction_method none _refine_ls_number_reflns 5599 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0585 _refine_ls_wR_factor_gt 0.0564 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.339 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.041 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 Se Se 0.783792(19) 0.194685(17) 0.013983(9) 0.03287(5) Uani 1 1 d . . . P P 0.64215(4) 0.25314(4) 0.13653(2) 0.02308(8) Uani 1 1 d . . . N1 N 0.85804(16) 0.00551(14) 0.21116(8) 0.0317(3) Uani 1 1 d . . . H1 H 0.898(2) 0.0149(19) 0.1567(13) 0.036(5) Uiso 1 1 d . . . N2 N 0.63929(15) 0.09751(14) 0.31211(8) 0.0317(3) Uani 1 1 d . . . C1 C 0.71125(17) 0.10683(15) 0.23339(9) 0.0269(3) Uani 1 1 d . . . C2 C 0.95887(17) -0.09624(15) 0.27885(9) 0.0283(3) Uani 1 1 d . . . H2 H 0.8943 -0.1523 0.3167 0.034 Uiso 1 1 calc R . . C3 C 1.01413(19) -0.01294(17) 0.34032(10) 0.0337(3) Uani 1 1 d . . . H3B H 1.0719 0.0483 0.3031 0.04 Uiso 1 1 calc R . . H3A H 0.9184 0.0543 0.373 0.04 Uiso 1 1 calc R . . C4 C 1.12535(19) -0.11943(18) 0.40840(10) 0.0363(3) Uani 1 1 d . . . H4B H 1.163 -0.0624 0.4453 0.044 Uiso 1 1 calc R . . H4A H 1.0646 -0.174 0.4495 0.044 Uiso 1 1 calc R . . C5 C 1.2701(2) -0.22888(19) 0.36099(12) 0.0412(4) Uani 1 1 d . . . H5B H 1.337 -0.3006 0.4065 0.049 Uiso 1 1 calc R . . H5A H 1.3373 -0.1752 0.3249 0.049 Uiso 1 1 calc R . . C6 C 1.2162(2) -0.31170(19) 0.29941(12) 0.0466(4) Uani 1 1 d . . . H6B H 1.1593 -0.3739 0.3365 0.056 Uiso 1 1 calc R . . H6A H 1.3124 -0.3782 0.2666 0.056 Uiso 1 1 calc R . . C7 C 1.1041(2) -0.20599(18) 0.23129(11) 0.0392(4) Uani 1 1 d . . . H7B H 1.1643 -0.1513 0.1898 0.047 Uiso 1 1 calc R . . H7A H 1.0666 -0.2636 0.1948 0.047 Uiso 1 1 calc R . . C8 C 0.49075(17) 0.21006(16) 0.34404(9) 0.0288(3) Uani 1 1 d . . . H8 H 0.4667 0.3012 0.3003 0.035 Uiso 1 1 calc R . . C9 C 0.51869(19) 0.24610(19) 0.43560(10) 0.0375(3) Uani 1 1 d . . . H9B H 0.5557 0.1531 0.4761 0.045 Uiso 1 1 calc R . . H9A H 0.6053 0.2901 0.4271 0.045 Uiso 1 1 calc R . . C10 C 0.3665(2) 0.3534(2) 0.48022(11) 0.0438(4) Uani 1 1 d . . . H10B H 0.3884 0.368 0.5408 0.053 Uiso 1 1 calc R . . H10A H 0.3365 0.4507 0.4435 0.053 Uiso 1 1 calc R . . C11 C 0.2267(2) 0.2946(2) 0.48931(12) 0.0500(5) Uani 1 1 d . . . H11B H 0.1276 0.3689 0.5146 0.06 Uiso 1 1 calc R . . H11A H 0.2516 0.2029 0.5315 0.06 Uiso 1 1 calc R . . C12 C 0.1972(2) 0.2616(2) 0.39772(12) 0.0432(4) Uani 1 1 d . . . H12B H 0.163 0.3549 0.3573 0.052 Uiso 1 1 calc R . . H12A H 0.1089 0.2198 0.4054 0.052 Uiso 1 1 calc R . . C13 C 0.34959(19) 0.15204(18) 0.35467(11) 0.0371(3) Uani 1 1 d . . . H13B H 0.3788 0.0561 0.3928 0.045 Uiso 1 1 calc R . . H13A H 0.328 0.1348 0.2946 0.045 Uiso 1 1 calc R . . C14 C 0.43392(17) 0.27398(16) 0.12571(9) 0.0272(3) Uani 1 1 d . . . C15 C 0.4059(2) 0.15120(19) 0.10220(12) 0.0420(4) Uani 1 1 d . . . H15 H 0.493 0.0605 0.0961 0.05 Uiso 1 1 calc R . . C16 C 0.2505(3) 0.1619(2) 0.08780(14) 0.0546(5) Uani 1 1 d . . . H16 H 0.231 0.078 0.0726 0.065 Uiso 1 1 calc R . . C17 C 0.1243(2) 0.2939(3) 0.09540(14) 0.0591(5) Uani 1 1 d . . . H17 H 0.0182 0.3009 0.0849 0.071 Uiso 1 1 calc R . . C18 C 0.1513(2) 0.4147(2) 0.11798(15) 0.0544(5) Uani 1 1 d . . . H18 H 0.0638 0.5054 0.1229 0.065 Uiso 1 1 calc R . . C19 C 0.30584(19) 0.40556(19) 0.13377(11) 0.0372(3) Uani 1 1 d . . . H19 H 0.3236 0.4896 0.1501 0.045 Uiso 1 1 calc R . . C20 C 0.65460(16) 0.42041(15) 0.17156(9) 0.0254(3) Uani 1 1 d . . . C21 C 0.73261(19) 0.41600(18) 0.24749(10) 0.0338(3) Uani 1 1 d . . . H21 H 0.7739 0.3254 0.2845 0.041 Uiso 1 1 calc R . . C22 C 0.7500(2) 0.5444(2) 0.26916(12) 0.0438(4) Uani 1 1 d . . . H22 H 0.804 0.5411 0.3208 0.053 Uiso 1 1 calc R . . C23 C 0.6896(2) 0.6762(2) 0.21618(13) 0.0490(4) Uani 1 1 d . . . H23 H 0.7003 0.7639 0.2318 0.059 Uiso 1 1 calc R . . C24 C 0.6132(3) 0.68096(19) 0.14032(13) 0.0486(4) Uani 1 1 d . . . H24 H 0.5714 0.7721 0.1039 0.058 Uiso 1 1 calc R . . C25 C 0.5974(2) 0.55350(17) 0.11708(11) 0.0372(3) Uani 1 1 d . . . H25 H 0.5475 0.5568 0.0639 0.045 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 Se 0.03673(9) 0.04019(9) 0.02207(8) -0.00870(6) 0.00155(6) -0.01288(7) P 0.02622(17) 0.02503(17) 0.01961(16) -0.00362(12) -0.00250(13) -0.01002(14) N1 0.0337(7) 0.0334(7) 0.0211(6) -0.0025(5) -0.0020(5) -0.0031(5) N2 0.0322(6) 0.0326(6) 0.0259(6) 0.0008(5) -0.0005(5) -0.0077(5) C1 0.0300(7) 0.0263(7) 0.0246(6) -0.0023(5) -0.0047(5) -0.0092(6) C2 0.0313(7) 0.0278(7) 0.0237(6) -0.0024(5) -0.0037(5) -0.0071(6) C3 0.0351(8) 0.0320(8) 0.0322(7) -0.0095(6) -0.0042(6) -0.0063(6) C4 0.0366(8) 0.0416(9) 0.0309(8) -0.0083(6) -0.0064(6) -0.0106(7) C5 0.0354(8) 0.0414(9) 0.0425(9) -0.0090(7) -0.0106(7) -0.0036(7) C6 0.0495(10) 0.0350(8) 0.0464(10) -0.0141(7) -0.0168(8) 0.0046(7) C7 0.0432(9) 0.0355(8) 0.0309(8) -0.0118(6) -0.0070(7) 0.0008(7) C8 0.0300(7) 0.0315(7) 0.0223(6) 0.0014(5) 0.0002(5) -0.0096(6) C9 0.0347(8) 0.0495(9) 0.0246(7) -0.0032(6) -0.0024(6) -0.0099(7) C10 0.0432(9) 0.0530(10) 0.0311(8) -0.0119(7) -0.0028(7) -0.0087(8) C11 0.0403(9) 0.0615(12) 0.0401(9) -0.0100(8) 0.0110(8) -0.0104(9) C12 0.0328(8) 0.0493(10) 0.0484(10) -0.0065(8) 0.0046(7) -0.0173(7) C13 0.0379(8) 0.0381(8) 0.0367(8) -0.0031(6) 0.0047(7) -0.0175(7) C14 0.0304(7) 0.0333(7) 0.0225(6) -0.0027(5) -0.0041(5) -0.0161(6) C15 0.0489(10) 0.0388(9) 0.0477(9) -0.0077(7) -0.0044(8) -0.0252(8) C16 0.0624(12) 0.0707(13) 0.0542(11) -0.0156(10) -0.0019(9) -0.0493(11) C17 0.0388(10) 0.0948(17) 0.0598(12) -0.0192(11) -0.0034(9) -0.0388(11) C18 0.0290(8) 0.0690(13) 0.0662(13) -0.0192(10) -0.0050(8) -0.0130(9) C19 0.0303(8) 0.0420(9) 0.0427(9) -0.0130(7) -0.0037(6) -0.0129(7) C20 0.0271(7) 0.0290(7) 0.0235(6) -0.0067(5) 0.0009(5) -0.0132(5) C21 0.0359(8) 0.0399(8) 0.0301(7) -0.0064(6) -0.0063(6) -0.0161(7) C22 0.0470(10) 0.0571(11) 0.0399(9) -0.0193(8) -0.0049(7) -0.0275(8) C23 0.0581(11) 0.0440(10) 0.0582(11) -0.0200(8) 0.0026(9) -0.0308(9) C24 0.0665(12) 0.0324(9) 0.0529(11) -0.0024(7) -0.0066(9) -0.0243(8) C25 0.0509(9) 0.0331(8) 0.0324(8) -0.0012(6) -0.0080(7) -0.0197(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Se P 2.1183(4) . ? P C14 1.8108(14) . ? P C20 1.8131(14) . ? P C1 1.8811(14) . ? N1 C1 1.3602(18) . ? N1 C2 1.4595(18) . ? N2 C1 1.2785(18) . ? N2 C8 1.4585(18) . ? C2 C7 1.521(2) . ? C2 C3 1.528(2) . ? C3 C4 1.524(2) . ? C4 C5 1.516(2) . ? C5 C6 1.519(2) . ? C6 C7 1.525(2) . ? C8 C13 1.527(2) . ? C8 C9 1.531(2) . ? C9 C10 1.525(2) . ? C10 C11 1.522(3) . ? C11 C12 1.524(3) . ? C12 C13 1.526(2) . ? C14 C19 1.384(2) . ? C14 C15 1.395(2) . ? C15 C16 1.386(3) . ? C16 C17 1.378(3) . ? C17 C18 1.366(3) . ? C18 C19 1.390(2) . ? C20 C21 1.391(2) . ? C20 C25 1.393(2) . ? C21 C22 1.391(2) . ? C22 C23 1.376(3) . ? C23 C24 1.381(3) . ? C24 C25 1.385(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 P C20 110.55(6) . . ? C14 P C1 106.32(6) . . ? C20 P C1 105.19(6) . . ? C14 P Se 110.19(5) . . ? C20 P Se 111.98(4) . . ? C1 P Se 112.37(4) . . ? C1 N1 C2 122.49(12) . . ? C1 N2 C8 124.06(12) . . ? N2 C1 N1 120.95(13) . . ? N2 C1 P 127.96(11) . . ? N1 C1 P 111.07(10) . . ? N1 C2 C7 109.06(11) . . ? N1 C2 C3 111.36(12) . . ? C7 C2 C3 110.39(13) . . ? C4 C3 C2 111.41(12) . . ? C5 C4 C3 110.96(13) . . ? C4 C5 C6 110.73(14) . . ? C5 C6 C7 111.81(14) . . ? C2 C7 C6 110.95(13) . . ? N2 C8 C13 110.49(12) . . ? N2 C8 C9 107.28(12) . . ? C13 C8 C9 109.89(12) . . ? C10 C9 C8 112.41(13) . . ? C11 C10 C9 111.00(15) . . ? C10 C11 C12 110.63(14) . . ? C11 C12 C13 111.07(15) . . ? C8 C13 C12 111.26(13) . . ? C19 C14 C15 119.37(14) . . ? C19 C14 P 123.80(11) . . ? C15 C14 P 116.70(12) . . ? C16 C15 C14 119.78(17) . . ? C17 C16 C15 120.28(17) . . ? C18 C17 C16 120.15(17) . . ? C17 C18 C19 120.41(18) . . ? C14 C19 C18 120.00(16) . . ? C21 C20 C25 119.31(13) . . ? C21 C20 P 121.21(11) . . ? C25 C20 P 119.24(11) . . ? C22 C21 C20 119.92(15) . . ? C23 C22 C21 120.34(16) . . ? C22 C23 C24 120.00(15) . . ? C23 C24 C25 120.29(17) . . ? C24 C25 C20 120.11(15) . . ? #===END