##### Supporting Information for X-ray Structure 6a ##### data_dec3704 _audit_creation_date 2004-12-21T13:52:09-00:00 _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 _publ_requested_category FO #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H37 N2 P Se' _chemical_formula_sum 'C19 H37 N2 P Se' _chemical_formula_weight 403.44 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9350(3) _cell_length_b 10.0808(3) _cell_length_c 12.5565(4) _cell_angle_alpha 77.397(2) _cell_angle_beta 78.020(2) _cell_angle_gamma 77.321(2) _cell_volume 1061.57(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9341 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.022 _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 0.2 _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.846 _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 0.5589 _exptl_absorpt_correction_T_max 0.6265 #----------------------------------------------------------------------------# # 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 -0.832135E-1 _diffrn_orient_matrix_ub_12 0.125017E-1 _diffrn_orient_matrix_ub_13 0.657649E-1 _diffrn_orient_matrix_ub_21 -0.616968E-1 _diffrn_orient_matrix_ub_22 -0.554662E-1 _diffrn_orient_matrix_ub_23 -0.250858E-1 _diffrn_orient_matrix_ub_31 0.530074E-1 _diffrn_orient_matrix_ub_32 -0.863443E-1 _diffrn_orient_matrix_ub_33 0.435663E-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 0.0392 _diffrn_reflns_av_unetI/netI 0.0326 _diffrn_reflns_number 14137 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 26.01 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 4158 _reflns_number_gt 3695 _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 H atom on N1 was refined; other H atoms 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^)+(0.0287P)^2^+0.4807P] 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 4158 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.067 _refine_ls_wR_factor_gt 0.0646 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.401 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.053 #----------------------------------------------------------------------------# # 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 0.41596(2) 0.38623(2) 0.850152(16) 0.02894(8) Uani 1 1 d . . . P P 0.66203(6) 0.35236(5) 0.83460(4) 0.02127(11) Uani 1 1 d . . . N1 N 0.6630(3) 0.3171(3) 0.62575(17) 0.0543(7) Uani 1 1 d . . . H1N H 0.573(3) 0.336(3) 0.652(2) 0.054(8) Uiso 1 1 d . . . N2 N 0.90653(19) 0.27602(17) 0.69085(13) 0.0270(4) Uani 1 1 d . . . C1 C 0.7328(2) 0.50696(18) 0.84380(15) 0.0236(4) Uani 1 1 d . . . H1 H 0.6717 0.5399 0.9124 0.028 Uiso 1 1 calc R . . C2 C 0.9055(2) 0.4833(2) 0.85375(18) 0.0310(5) Uani 1 1 d . . . H2A H 0.9251 0.4136 0.9207 0.037 Uiso 1 1 calc R . . H2B H 0.9701 0.447 0.7885 0.037 Uiso 1 1 calc R . . C3 C 0.9519(3) 0.6180(2) 0.86116(18) 0.0360(5) Uani 1 1 d . . . H3A H 0.8955 0.6486 0.9308 0.043 Uiso 1 1 calc R . . H3B H 1.0648 0.6011 0.8631 0.043 Uiso 1 1 calc R . . C4 C 0.9150(3) 0.7315(2) 0.7634(2) 0.0423(6) Uani 1 1 d . . . H4A H 0.941 0.8183 0.773 0.051 Uiso 1 1 calc R . . H4B H 0.9796 0.7053 0.6944 0.051 Uiso 1 1 calc R . . C5 C 0.7446(3) 0.7552(2) 0.7540(2) 0.0406(5) Uani 1 1 d . . . H5A H 0.7251 0.8258 0.6875 0.049 Uiso 1 1 calc R . . H5B H 0.6807 0.7912 0.8196 0.049 Uiso 1 1 calc R . . C6 C 0.6954(3) 0.6224(2) 0.74575(17) 0.0325(5) Uani 1 1 d . . . H6A H 0.7504 0.5921 0.6757 0.039 Uiso 1 1 calc R . . H6B H 0.5822 0.6407 0.7445 0.039 Uiso 1 1 calc R . . C7 C 0.7422(2) 0.20909(18) 0.93638(15) 0.0226(4) Uani 1 1 d . . . H7 H 0.858 0.2005 0.9215 0.027 Uiso 1 1 calc R . . C8 C 0.6826(3) 0.2392(2) 1.05395(15) 0.0290(4) Uani 1 1 d . . . H8A H 0.7142 0.3251 1.0601 0.035 Uiso 1 1 calc R . . H8B H 0.5675 0.2537 1.0688 0.035 Uiso 1 1 calc R . . C9 C 0.7477(3) 0.1199(2) 1.13972(17) 0.0344(5) Uani 1 1 d . . . H9A H 0.8618 0.1126 1.13 0.041 Uiso 1 1 calc R . . H9B H 0.7025 0.1394 1.2149 0.041 Uiso 1 1 calc R . . C10 C 0.7112(3) -0.0167(2) 1.12917(17) 0.0373(5) Uani 1 1 d . . . H10A H 0.5974 -0.0135 1.1482 0.045 Uiso 1 1 calc R . . H10B H 0.7616 -0.0924 1.1822 0.045 Uiso 1 1 calc R . . C11 C 0.7683(3) -0.0464(2) 1.01225(17) 0.0333(5) Uani 1 1 d . . . H11A H 0.736 -0.1322 1.0067 0.04 Uiso 1 1 calc R . . H11B H 0.8834 -0.0615 0.9968 0.04 Uiso 1 1 calc R . . C12 C 0.7037(2) 0.07222(19) 0.92597(16) 0.0275(4) Uani 1 1 d . . . H12A H 0.5894 0.0804 0.9359 0.033 Uiso 1 1 calc R . . H12B H 0.7485 0.0521 0.8509 0.033 Uiso 1 1 calc R . . C13 C 0.7595(2) 0.30500(19) 0.69824(15) 0.0237(4) Uani 1 1 d . . . C14 C 0.6798(3) 0.2366(2) 0.53831(17) 0.0340(5) Uani 1 1 d . . . H14 H 0.79 0.1872 0.5245 0.041 Uiso 1 1 calc R . . C15 C 0.6443(4) 0.3345(3) 0.4342(2) 0.0649(8) Uani 1 1 d . . . H15A H 0.715 0.4012 0.4136 0.097 Uiso 1 1 calc R . . H15B H 0.5366 0.3839 0.4467 0.097 Uiso 1 1 calc R . . H15C H 0.6583 0.2824 0.3744 0.097 Uiso 1 1 calc R . . C16 C 0.5751(4) 0.1312(3) 0.5740(3) 0.0827(11) Uani 1 1 d . . . H16A H 0.6023 0.0692 0.6418 0.124 Uiso 1 1 calc R . . H16B H 0.5883 0.0775 0.5154 0.124 Uiso 1 1 calc R . . H16C H 0.4666 0.1783 0.5883 0.124 Uiso 1 1 calc R . . C17 C 1.0142(2) 0.2540(2) 0.58858(16) 0.0301(5) Uani 1 1 d . . . H17 H 0.9587 0.2906 0.5238 0.036 Uiso 1 1 calc R . . C18 C 1.1431(3) 0.3348(3) 0.5798(2) 0.0490(6) Uani 1 1 d . . . H18A H 1.0982 0.4331 0.577 0.073 Uiso 1 1 calc R . . H18B H 1.2187 0.3228 0.5123 0.073 Uiso 1 1 calc R . . H18C H 1.1954 0.3005 0.6445 0.073 Uiso 1 1 calc R . . C19 C 1.0785(3) 0.1009(3) 0.5933(2) 0.0490(6) Uani 1 1 d . . . H19A H 0.9933 0.0518 0.5984 0.073 Uiso 1 1 calc R . . H19B H 1.1296 0.0647 0.6583 0.073 Uiso 1 1 calc R . . H19C H 1.1543 0.0872 0.5261 0.073 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 0.02251(12) 0.03307(12) 0.03124(12) -0.01043(8) -0.00250(8) -0.00240(8) P 0.0229(3) 0.0227(2) 0.0183(2) -0.00630(18) -0.0024(2) -0.0027(2) N1 0.0318(12) 0.0949(18) 0.0382(11) -0.0418(12) -0.0158(10) 0.0234(12) N2 0.0282(9) 0.0333(9) 0.0208(8) -0.0108(7) 0.0007(7) -0.0072(7) C1 0.0290(10) 0.0227(9) 0.0202(9) -0.0064(7) -0.0028(8) -0.0054(8) C2 0.0327(12) 0.0294(11) 0.0345(11) -0.0077(9) -0.0103(9) -0.0066(9) C3 0.0360(12) 0.0370(12) 0.0413(13) -0.0131(10) -0.0076(10) -0.0128(10) C4 0.0502(15) 0.0372(12) 0.0421(13) -0.0072(10) -0.0013(11) -0.0193(11) C5 0.0509(15) 0.0280(11) 0.0421(13) 0.0028(9) -0.0121(11) -0.0103(10) C6 0.0407(13) 0.0280(11) 0.0292(11) -0.0013(8) -0.0101(10) -0.0070(9) C7 0.0232(10) 0.0237(9) 0.0208(9) -0.0056(7) -0.0028(8) -0.0030(8) C8 0.0364(12) 0.0293(10) 0.0214(9) -0.0071(8) -0.0032(9) -0.0056(9) C9 0.0457(13) 0.0371(12) 0.0232(10) -0.0056(9) -0.0103(10) -0.0089(10) C10 0.0511(14) 0.0329(11) 0.0292(11) 0.0024(9) -0.0118(10) -0.0133(10) C11 0.0416(13) 0.0250(10) 0.0344(11) -0.0038(9) -0.0097(10) -0.0070(9) C12 0.0348(11) 0.0258(10) 0.0242(10) -0.0075(8) -0.0049(9) -0.0075(9) C13 0.0263(11) 0.0235(9) 0.0204(9) -0.0062(7) -0.0040(8) -0.0001(8) C14 0.0281(11) 0.0447(13) 0.0317(11) -0.0192(10) -0.0086(9) 0.0036(10) C15 0.091(2) 0.0706(19) 0.0359(14) -0.0143(13) -0.0210(15) -0.0053(17) C16 0.059(2) 0.0468(17) 0.131(3) -0.0263(19) 0.017(2) -0.0054(15) C17 0.0264(11) 0.0421(12) 0.0182(9) -0.0054(8) -0.0029(8) 0.0003(9) C18 0.0316(13) 0.0758(18) 0.0351(13) 0.0000(12) 0.0009(10) -0.0165(12) C19 0.0500(16) 0.0522(15) 0.0415(13) -0.0219(11) -0.0139(12) 0.0167(12) #----------------------------------------------------------------------------# # 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 2.1237(5) . ? P C7 1.8311(18) . ? P C1 1.8393(19) . ? P C13 1.8635(19) . ? N1 C13 1.348(3) . ? N1 C14 1.467(3) . ? N2 C13 1.270(3) . ? N2 C17 1.463(2) . ? C1 C6 1.535(3) . ? C1 C2 1.536(3) . ? C2 C3 1.530(3) . ? C3 C4 1.521(3) . ? C4 C5 1.514(3) . ? C5 C6 1.527(3) . ? C7 C12 1.532(3) . ? C7 C8 1.534(3) . ? C8 C9 1.527(3) . ? C9 C10 1.522(3) . ? C10 C11 1.523(3) . ? C11 C12 1.526(3) . ? C14 C15 1.501(3) . ? C14 C16 1.502(4) . ? C17 C19 1.518(3) . ? C17 C18 1.524(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 C7 P C1 107.68(8) . . ? C7 P C13 104.31(8) . . ? C1 P C13 106.23(9) . . ? C7 P Se 114.11(6) . . ? C1 P Se 112.45(7) . . ? C13 P Se 111.45(6) . . ? C13 N1 C14 128.42(19) . . ? C13 N2 C17 124.03(16) . . ? C6 C1 C2 110.93(16) . . ? C6 C1 P 109.65(13) . . ? C2 C1 P 115.19(13) . . ? C3 C2 C1 110.90(17) . . ? C4 C3 C2 111.60(17) . . ? C5 C4 C3 110.95(18) . . ? C4 C5 C6 111.81(18) . . ? C5 C6 C1 111.13(17) . . ? C12 C7 C8 110.81(16) . . ? C12 C7 P 111.25(13) . . ? C8 C7 P 110.44(13) . . ? C9 C8 C7 110.95(16) . . ? C10 C9 C8 111.65(17) . . ? C9 C10 C11 111.33(17) . . ? C10 C11 C12 111.66(17) . . ? C11 C12 C7 111.07(16) . . ? N2 C13 N1 133.07(19) . . ? N2 C13 P 111.93(13) . . ? N1 C13 P 114.82(15) . . ? N1 C14 C15 108.6(2) . . ? N1 C14 C16 110.2(2) . . ? C15 C14 C16 112.0(2) . . ? N2 C17 C19 109.84(17) . . ? N2 C17 C18 106.50(17) . . ? C19 C17 C18 111.3(2) . . ? #===END