Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_section_title ;The reactions of alkylamino substituted phosphines with I2 and (Ph2Se2I2)2: structural features of alkylamino phosphonium cations. ; _publ_requested_category FO _publ_contact_author_name 'Stephen Godfrey' _publ_contact_author_email STEPHEN.M.GODFREY@MANCHESTER.AC.UK loop_ _publ_author_name S.Godfrey N.A.Barnes R.T.A.Halton I.Mushtaq R.Pritchard # Attachment 'Compound1.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-07-16 at 14:54:05 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : shelxl dreduc sortav struct data_shelxl1 _database_code_depnum_ccdc_archive 'CCDC 659625' _audit_creation_date 2007-07-16T14:54:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H30 I2 N3 P1' _chemical_formula_sum 'C12 H30 I2 N3 P' _chemical_formula_weight 501.16 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.9120(2) _cell_length_b 13.7750(3) _cell_length_c 8.5280(3) _cell_angle_alpha 90 _cell_angle_beta 94.7030(10) _cell_angle_gamma 90 _cell_volume 926.32(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2078 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.797 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.473 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.5905 _exptl_absorpt_correction_T_max 0.6949 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(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_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.183148E-1 _diffrn_orient_matrix_ub_12 -0.707525E-1 _diffrn_orient_matrix_ub_13 -0.18654E-1 _diffrn_orient_matrix_ub_21 -0.703681E-1 _diffrn_orient_matrix_ub_22 0.4595E-2 _diffrn_orient_matrix_ub_23 -0.102626 _diffrn_orient_matrix_ub_31 0.103909 _diffrn_orient_matrix_ub_32 0.155824E-1 _diffrn_orient_matrix_ub_33 -0.544368E-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 0.067 _diffrn_reflns_av_unetI/netI 0.0303 _diffrn_reflns_number 7267 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 26.49 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _reflns_number_total 1965 _reflns_number_gt 1743 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # 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. All the heavy atoms and some of the light atoms obey the mirror symmetry operations of P21/m. The remaining peaks in the difference fourier map coincide with this plane and are probly 'ghost' iodine atoms resulting from stacking faults. Twinning has been ruled out and apropriate absorption corrections have been carried out. ; _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^)+(0.0222P)^2^+13.7386P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.00601(18) _refine_ls_number_reflns 1965 _refine_ls_number_parameters 164 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1175 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(9) _refine_diff_density_max 3.095 _refine_diff_density_min -1.705 _refine_diff_density_rms 0.217 #----------------------------------------------------------------------------# # 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 0.1026 0.0946 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4442 1.8168 '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 C1 C 0.0010(5) 0.8802(3) 0.2917(6) 0.0310(12) Uani 1 1 d . . . H1A H -0.0251 0.9022 0.3975 0.037 Uiso 1 1 calc R . . H1B H -0.0367 0.8119 0.2784 0.037 Uiso 1 1 calc R . . C2 C -0.0935(5) 0.9433(4) 0.1666(6) 0.0415(14) Uani 1 1 d . . . H2A H -0.2158 0.9386 0.1764 0.062 Uiso 1 1 calc R . . H2B H -0.0682 0.921 0.062 0.062 Uiso 1 1 calc R . . H2C H -0.0573 1.011 0.1811 0.062 Uiso 1 1 calc R . . C3 C 0.2675(6) 0.9826(3) 0.3235(5) 0.0307(12) Uani 1 1 d . . . H3A H 0.2107 1.0341 0.2575 0.037 Uiso 1 1 calc R . . H3B H 0.3887 0.9819 0.3027 0.037 Uiso 1 1 calc R . . C4 C 0.2528(7) 1.0066(4) 0.4964(7) 0.0481(15) Uani 1 1 d . . . H4A H 0.3065 1.0695 0.521 0.072 Uiso 1 1 calc R . . H4B H 0.3097 0.9562 0.5624 0.072 Uiso 1 1 calc R . . H4C H 0.1329 1.0096 0.5169 0.072 Uiso 1 1 calc R . . C5 C 0.1230(6) 0.6368(3) 0.1225(5) 0.0294(11) Uani 1 1 d . . . H5A H 0.1838 0.5743 0.1163 0.035 Uiso 1 1 calc R . . H5B H 0.1371 0.6731 0.0241 0.035 Uiso 1 1 calc R . . C6 C -0.0689(6) 0.6162(4) 0.1344(6) 0.0390(14) Uani 1 1 d . . . H6A H -0.1135 0.5787 0.0424 0.059 Uiso 1 1 calc R . . H6B H -0.1304 0.6778 0.138 0.059 Uiso 1 1 calc R . . H6C H -0.0836 0.579 0.2303 0.059 Uiso 1 1 calc R . . C7 C 0.1790(6) 0.6592(3) 0.4148(5) 0.0282(11) Uani 1 1 d . . . H7A H 0.0564 0.6545 0.4291 0.034 Uiso 1 1 calc R . . H7B H 0.2287 0.7079 0.4906 0.034 Uiso 1 1 calc R . . C8 C 0.2614(7) 0.5616(3) 0.4517(6) 0.0448(14) Uani 1 1 d . . . H8A H 0.2431 0.5431 0.5599 0.067 Uiso 1 1 calc R . . H8B H 0.3833 0.5661 0.4402 0.067 Uiso 1 1 calc R . . H8C H 0.2109 0.5127 0.3788 0.067 Uiso 1 1 calc R . . C9 C 0.4850(6) 0.7347(3) -0.0007(6) 0.0337(12) Uani 1 1 d . . . H9A H 0.5938 0.7698 -0.0035 0.04 Uiso 1 1 calc R . . H9B H 0.5025 0.6815 0.077 0.04 Uiso 1 1 calc R . . C10 C 0.4381(6) 0.6916(3) -0.1596(5) 0.0342(12) Uani 1 1 d . . . H10A H 0.5289 0.6483 -0.1882 0.051 Uiso 1 1 calc R . . H10B H 0.422 0.7437 -0.2377 0.051 Uiso 1 1 calc R . . H10C H 0.3325 0.6546 -0.1569 0.051 Uiso 1 1 calc R . . C11 C 0.3141(5) 0.8882(3) -0.0499(5) 0.0280(11) Uani 1 1 d . . . H11A H 0.2294 0.9293 -0.0021 0.034 Uiso 1 1 calc R . . H11B H 0.2625 0.8651 -0.1528 0.034 Uiso 1 1 calc R . . C12 C 0.4688(5) 0.9497(3) -0.0767(5) 0.0310(11) Uani 1 1 d . . . H12A H 0.4348 1.0043 -0.1459 0.047 Uiso 1 1 calc R . . H12B H 0.5525 0.9099 -0.1259 0.047 Uiso 1 1 calc R . . H12C H 0.5188 0.9745 0.0244 0.047 Uiso 1 1 calc R . . N1 N 0.1897(4) 0.8864(2) 0.2778(4) 0.0235(9) Uani 1 1 d . . . N2 N 0.2000(5) 0.6927(3) 0.2560(5) 0.0303(10) Uani 1 1 d . . . N3 N 0.3539(3) 0.8033(2) 0.0533(3) 0.0226(8) Uani 1 1 d . . . P1 P 0.30117(10) 0.79502(8) 0.23292(10) 0.0199(2) Uani 1 1 d . . . I1 I 0.55875(3) 0.790682(19) 0.41780(3) 0.02601(5) Uani 1 1 d . . . I2 I 0.89546(3) 0.77902(2) 0.73078(3) 0.03619(7) 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 0.0180(17) 0.0206(18) 0.055(3) -0.0038(19) 0.0076(17) 0.0011(15) C2 0.0192(18) 0.056(3) 0.048(3) 0.005(2) -0.0068(19) 0.006(2) C3 0.033(2) 0.0190(18) 0.040(2) -0.0026(18) -0.0003(19) -0.0071(17) C4 0.039(3) 0.040(3) 0.067(3) -0.020(2) 0.011(2) -0.003(2) C5 0.034(2) 0.0249(19) 0.028(2) 0.0006(17) -0.0020(17) 0.0028(17) C6 0.040(2) 0.038(2) 0.037(2) -0.004(2) -0.004(2) -0.010(2) C7 0.039(2) 0.0199(18) 0.0261(19) 0.0013(16) 0.0037(17) -0.0027(17) C8 0.047(3) 0.025(2) 0.059(3) 0.024(2) -0.016(2) 0.003(2) C9 0.038(2) 0.0203(19) 0.042(2) -0.0021(18) -0.0003(19) -0.0040(18) C10 0.044(2) 0.027(2) 0.033(2) -0.0027(18) 0.0145(18) -0.0102(19) C11 0.033(2) 0.0217(18) 0.028(2) 0.0084(17) -0.0053(17) -0.0029(17) C12 0.030(2) 0.0245(19) 0.037(2) 0.0014(18) -0.0021(18) -0.0087(17) N1 0.0157(13) 0.0124(13) 0.0426(18) -0.0065(14) 0.0044(13) -0.0027(12) N2 0.0301(17) 0.0182(15) 0.042(2) -0.0111(15) -0.0024(16) 0.0001(14) N3 0.0115(11) 0.0233(16) 0.0332(15) 0.0084(14) 0.0038(10) -0.0069(12) P1 0.0181(3) 0.0144(4) 0.0265(4) 0.0002(5) -0.0025(3) 0.0006(4) I1 0.02366(9) 0.02590(10) 0.02767(10) 0.00075(13) -0.00277(8) -0.00076(12) I2 0.02766(10) 0.04934(16) 0.03094(11) 0.00076(15) -0.00134(9) -0.00012(15) #----------------------------------------------------------------------------# # 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 C1 N1 1.510(5) . ? C1 C2 1.524(7) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 H2A 0.98 . ? C2 H2B 0.98 . ? C2 H2C 0.98 . ? C3 N1 1.499(5) . ? C3 C4 1.525(8) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 N2 1.465(6) . ? C5 C6 1.557(7) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 N2 1.453(6) . ? C7 C8 1.516(6) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C9 C10 1.498(7) . ? C9 N3 1.503(6) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 N3 1.482(5) . ? C11 C12 1.521(6) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? N1 P1 1.602(3) . ? N2 P1 1.641(4) . ? N3 P1 1.625(3) . ? P1 I1 2.4730(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 110.1(4) . . ? N1 C1 H1A 109.6 . . ? C2 C1 H1A 109.6 . . ? N1 C1 H1B 109.6 . . ? C2 C1 H1B 109.6 . . ? H1A C1 H1B 108.1 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C4 112.4(4) . . ? N1 C3 H3A 109.1 . . ? C4 C3 H3A 109.1 . . ? N1 C3 H3B 109.1 . . ? C4 C3 H3B 109.1 . . ? H3A C3 H3B 107.8 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N2 C5 C6 113.0(4) . . ? N2 C5 H5A 109 . . ? C6 C5 H5A 109 . . ? N2 C5 H5B 109 . . ? C6 C5 H5B 109 . . ? H5A C5 H5B 107.8 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 C8 113.2(4) . . ? N2 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? N2 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 N3 113.6(4) . . ? C10 C9 H9A 108.9 . . ? N3 C9 H9A 108.9 . . ? C10 C9 H9B 108.9 . . ? N3 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N3 C11 C12 113.2(3) . . ? N3 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? N3 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C3 N1 C1 114.7(3) . . ? C3 N1 P1 122.3(3) . . ? C1 N1 P1 122.8(3) . . ? C7 N2 C5 119.1(3) . . ? C7 N2 P1 118.6(3) . . ? C5 N2 P1 122.3(3) . . ? C11 N3 C9 115.7(3) . . ? C11 N3 P1 123.8(3) . . ? C9 N3 P1 118.8(3) . . ? N1 P1 N3 111.03(18) . . ? N1 P1 N2 111.32(18) . . ? N3 P1 N2 109.81(19) . . ? N1 P1 I1 107.92(13) . . ? N3 P1 I1 109.94(10) . . ? N2 P1 I1 106.71(14) . . ? 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 C4 C3 N1 C1 63.3(5) . . . . ? C4 C3 N1 P1 -111.4(4) . . . . ? C2 C1 N1 C3 69.5(5) . . . . ? C2 C1 N1 P1 -115.8(4) . . . . ? C8 C7 N2 C5 64.0(5) . . . . ? C8 C7 N2 P1 -119.1(4) . . . . ? C6 C5 N2 C7 52.0(5) . . . . ? C6 C5 N2 P1 -124.8(4) . . . . ? C12 C11 N3 C9 -57.0(5) . . . . ? C12 C11 N3 P1 107.8(4) . . . . ? C10 C9 N3 C11 -59.2(5) . . . . ? C10 C9 N3 P1 135.1(3) . . . . ? C3 N1 P1 N3 -79.7(3) . . . . ? C1 N1 P1 N3 106.0(3) . . . . ? C3 N1 P1 N2 157.6(3) . . . . ? C1 N1 P1 N2 -16.7(4) . . . . ? C3 N1 P1 I1 40.8(4) . . . . ? C1 N1 P1 I1 -133.5(3) . . . . ? C11 N3 P1 N1 4.2(3) . . . . ? C9 N3 P1 N1 168.6(3) . . . . ? C11 N3 P1 N2 127.8(3) . . . . ? C9 N3 P1 N2 -67.8(3) . . . . ? C11 N3 P1 I1 -115.1(3) . . . . ? C9 N3 P1 I1 49.3(3) . . . . ? C7 N2 P1 N1 -71.9(3) . . . . ? C5 N2 P1 N1 104.9(3) . . . . ? C7 N2 P1 N3 164.8(3) . . . . ? C5 N2 P1 N3 -18.5(4) . . . . ? C7 N2 P1 I1 45.6(3) . . . . ? C5 N2 P1 I1 -137.6(3) . . . . ? # Attachment 'Compound2.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-08-17 at 17:43:44 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : shelxl dreduc sortav struct data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 659626' _audit_creation_date 2007-08-17T17:43:44-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H42 I2 N3 P1' _chemical_formula_sum 'C18 H42 I2 N3 P' _chemical_formula_weight 585.32 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 c 1' _symmetry_space_group_name_Hall 'C -2yc' _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 16.5326(4) _cell_length_b 9.4427(2) _cell_length_c 16.7970(5) _cell_angle_alpha 90 _cell_angle_beta 101.2140(10) _cell_angle_gamma 90 _cell_volume 2572.16(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3089 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.513 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.6333 _exptl_absorpt_correction_T_max 0.7872 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(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_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.368954E-1 _diffrn_orient_matrix_ub_12 0.164514E-1 _diffrn_orient_matrix_ub_13 0.538587E-1 _diffrn_orient_matrix_ub_21 -0.438926E-1 _diffrn_orient_matrix_ub_22 -0.36786E-1 _diffrn_orient_matrix_ub_23 0.279428E-1 _diffrn_orient_matrix_ub_31 0.226845E-1 _diffrn_orient_matrix_ub_32 -0.979355E-1 _diffrn_orient_matrix_ub_33 -0.14484E-2 _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 0.045 _diffrn_reflns_av_unetI/netI 0.0306 _diffrn_reflns_number 12181 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 26.49 _diffrn_reflns_theta_full 26.49 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 2648 _reflns_number_gt 2230 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # 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 'SIR92 (Giacovazzo et al, 1993)' _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^)+(0.0495P)^2^+37.8653P] 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_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0015(2) _refine_ls_number_reflns 2648 _refine_ls_number_parameters 213 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.056 _refine_ls_wR_factor_ref 0.1445 _refine_ls_wR_factor_gt 0.1284 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(7) _refine_diff_density_max 1.997 _refine_diff_density_min -1.306 _refine_diff_density_rms 0.152 #----------------------------------------------------------------------------# # 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' I I -0.4742 1.8119 '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 C1 C 0.7836(10) 0.1150(18) 0.2401(9) 0.049(3) Uani 1 1 d . . . H1A H 0.841 0.0923 0.2666 0.059 Uiso 1 1 calc R . . H1B H 0.7527 0.0248 0.2312 0.059 Uiso 1 1 calc R . . C2 C 0.7845(13) 0.181(2) 0.1609(11) 0.068(5) Uani 1 1 d . . . H2A H 0.81 0.2756 0.1691 0.081 Uiso 1 1 calc R . . H2B H 0.7271 0.1924 0.1307 0.081 Uiso 1 1 calc R . . C3 C 0.8324(14) 0.090(2) 0.1113(11) 0.078(6) Uani 1 1 d . . . H3A H 0.8362 0.1396 0.0609 0.116 Uiso 1 1 calc R . . H3B H 0.8039 -0.0005 0.0984 0.116 Uiso 1 1 calc R . . H3C H 0.8879 0.0728 0.1427 0.116 Uiso 1 1 calc R . . C4 C 0.7942(9) 0.3345(15) 0.3259(10) 0.049(3) Uani 1 1 d . . . H4A H 0.7617 0.3927 0.3573 0.058 Uiso 1 1 calc R . . H4B H 0.802 0.3909 0.2783 0.058 Uiso 1 1 calc R . . C5 C 0.8785(10) 0.305(2) 0.3787(12) 0.062(4) Uani 1 1 d . . . H5A H 0.8725 0.2377 0.4225 0.074 Uiso 1 1 calc R . . H5B H 0.9151 0.2613 0.3455 0.074 Uiso 1 1 calc R . . C6 C 0.9163(14) 0.443(3) 0.4156(18) 0.097(8) Uani 1 1 d . . . H6A H 0.9692 0.4229 0.4516 0.145 Uiso 1 1 calc R . . H6B H 0.8789 0.4873 0.4469 0.145 Uiso 1 1 calc R . . H6C H 0.925 0.5069 0.3722 0.145 Uiso 1 1 calc R . . C7 C 0.5128(9) 0.2761(15) 0.3232(9) 0.046(3) Uani 1 1 d . . . H7A H 0.465 0.2542 0.2795 0.056 Uiso 1 1 calc R . . H7B H 0.5186 0.1975 0.3628 0.056 Uiso 1 1 calc R . . C8 C 0.4945(11) 0.4117(18) 0.3654(11) 0.061(4) Uani 1 1 d . . . H8A H 0.4859 0.4912 0.3263 0.073 Uiso 1 1 calc R . . H8B H 0.5414 0.4355 0.4097 0.073 Uiso 1 1 calc R . . C9 C 0.4161(11) 0.3872(18) 0.4002(12) 0.059(4) Uani 1 1 d . . . H9A H 0.4032 0.4732 0.4279 0.088 Uiso 1 1 calc R . . H9B H 0.4252 0.3084 0.4388 0.088 Uiso 1 1 calc R . . H9C H 0.37 0.3646 0.3559 0.088 Uiso 1 1 calc R . . C10 C 0.5933(12) 0.381(2) 0.2232(9) 0.062(5) Uani 1 1 d . . . H10A H 0.6514 0.4022 0.2205 0.075 Uiso 1 1 calc R . . H10B H 0.5668 0.4703 0.2354 0.075 Uiso 1 1 calc R . . C11 C 0.5481(14) 0.322(2) 0.1403(12) 0.084(6) Uani 1 1 d . . . H11A H 0.5758 0.2349 0.1273 0.1 Uiso 1 1 calc R . . H11B H 0.4906 0.2983 0.1436 0.1 Uiso 1 1 calc R . . C12 C 0.5480(15) 0.424(3) 0.0775(14) 0.102(8) Uani 1 1 d . . . H12A H 0.5155 0.3881 0.0265 0.152 Uiso 1 1 calc R . . H12B H 0.6047 0.4416 0.0708 0.152 Uiso 1 1 calc R . . H12C H 0.5237 0.513 0.092 0.152 Uiso 1 1 calc R . . C13 C 0.5619(9) -0.0338(18) 0.2472(9) 0.048(3) Uani 1 1 d . . . H13A H 0.5304 -0.1066 0.2708 0.057 Uiso 1 1 calc R . . H13B H 0.5257 0.0499 0.2342 0.057 Uiso 1 1 calc R . . C14 C 0.5809(11) -0.089(2) 0.1713(11) 0.066(5) Uani 1 1 d . . . H14A H 0.6185 -0.1715 0.1836 0.08 Uiso 1 1 calc R . . H14B H 0.6096 -0.0155 0.1455 0.08 Uiso 1 1 calc R . . C15 C 0.5029(13) -0.135(3) 0.1119(12) 0.086(7) Uani 1 1 d . . . H15A H 0.5179 -0.1694 0.0616 0.129 Uiso 1 1 calc R . . H15B H 0.4653 -0.0547 0.1 0.129 Uiso 1 1 calc R . . H15C H 0.4757 -0.2118 0.1363 0.129 Uiso 1 1 calc R . . C16 C 0.6886(9) -0.1104(16) 0.3485(9) 0.047(3) Uani 1 1 d . . . H16A H 0.7388 -0.07 0.3827 0.057 Uiso 1 1 calc R . . H16B H 0.7061 -0.1676 0.3054 0.057 Uiso 1 1 calc R . . C17 C 0.6466(12) -0.2072(19) 0.4005(14) 0.070(5) Uani 1 1 d . . . H17A H 0.6345 -0.154 0.4476 0.083 Uiso 1 1 calc R . . H17B H 0.5939 -0.2426 0.3683 0.083 Uiso 1 1 calc R . . N1 N 0.7459(7) 0.2054(12) 0.2966(7) 0.044(3) Uani 1 1 d . . . N2 N 0.5912(7) 0.2821(12) 0.2859(7) 0.037(3) Uiso 1 1 d . . . N3 N 0.6352(6) 0.0077(12) 0.3099(7) 0.041(3) Uani 1 1 d . . . P1 P 0.6630(2) 0.1701(4) 0.3281(2) 0.0391(7) Uani 1 1 d . . . I1 I 0.69378(6) 0.20657(12) 0.47566(5) 0.0526(3) Uani 1 1 d . . . I2 I 0.79063(6) 0.66417(14) 0.17561(6) 0.0594(3) Uani 1 1 d . . . C18 C 0.7032(14) -0.330(2) 0.4295(17) 0.088(7) Uani 1 1 d . . . H18A H 0.6779 -0.3904 0.4654 0.133 Uiso 1 1 calc R . . H18B H 0.7561 -0.2942 0.4593 0.133 Uiso 1 1 calc R . . H18C H 0.7123 -0.3856 0.3828 0.133 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 C1 0.054(9) 0.047(9) 0.049(8) 0.002(7) 0.016(7) 0.000(7) C2 0.072(11) 0.086(13) 0.049(10) 0.007(9) 0.022(8) 0.003(10) C3 0.104(15) 0.084(14) 0.055(10) -0.021(10) 0.044(10) -0.022(12) C4 0.053(8) 0.035(7) 0.055(8) -0.002(6) 0.003(7) 0.000(6) C5 0.040(8) 0.062(11) 0.082(12) -0.012(9) 0.008(7) -0.008(7) C6 0.070(14) 0.090(17) 0.13(2) -0.043(15) 0.018(13) -0.027(12) C7 0.049(8) 0.042(9) 0.048(7) 0.007(6) 0.009(6) -0.003(6) C8 0.064(10) 0.049(9) 0.074(11) -0.005(8) 0.022(8) 0.006(8) C9 0.065(10) 0.038(8) 0.080(12) 0.000(8) 0.029(9) 0.003(8) C10 0.082(12) 0.075(12) 0.031(7) 0.022(7) 0.014(7) 0.012(9) C11 0.077(13) 0.094(15) 0.065(12) 0.010(11) -0.023(10) -0.019(11) C12 0.101(17) 0.12(2) 0.076(14) 0.036(14) 0.008(12) 0.037(16) C13 0.040(7) 0.056(9) 0.040(7) -0.007(7) -0.009(6) -0.010(6) C14 0.061(10) 0.068(11) 0.064(11) -0.014(9) -0.004(8) -0.008(9) C15 0.084(13) 0.103(17) 0.054(11) -0.032(11) -0.025(9) 0.004(12) C16 0.047(8) 0.044(8) 0.052(8) 0.011(6) 0.014(6) 0.008(6) C17 0.071(11) 0.045(9) 0.099(14) 0.013(9) 0.031(10) -0.004(8) N1 0.044(6) 0.041(6) 0.049(7) -0.007(5) 0.013(5) -0.010(5) N3 0.037(6) 0.035(6) 0.047(6) -0.011(5) -0.001(5) 0.000(5) P1 0.0368(16) 0.0421(19) 0.0378(17) 0.0021(14) 0.0054(13) 0.0000(14) I1 0.0587(6) 0.0588(6) 0.0394(5) 0.0011(5) 0.0074(4) 0.0054(5) I2 0.0651(7) 0.0603(6) 0.0501(6) 0.0046(6) 0.0046(5) 0.0013(6) C18 0.087(15) 0.045(11) 0.13(2) 0.029(12) 0.014(14) 0.001(10) #----------------------------------------------------------------------------# # 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 C1 C2 1.47(2) . ? C1 N1 1.498(19) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.52(3) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 H3A 0.98 . ? C3 H3B 0.98 . ? C3 H3C 0.98 . ? C4 N1 1.487(18) . ? C4 C5 1.53(2) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.52(3) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 C8 1.52(2) . ? C7 N2 1.547(18) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 C9 1.54(2) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C10 N2 1.413(19) . ? C10 C11 1.55(3) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.43(3) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 H12A 0.98 . ? C12 H12B 0.98 . ? C12 H12C 0.98 . ? C13 C14 1.47(2) . ? C13 N3 1.495(16) . ? C13 H13A 0.99 . ? C13 H13B 0.99 . ? C14 C15 1.53(2) . ? C14 H14A 0.99 . ? C14 H14B 0.99 . ? C15 H15A 0.98 . ? C15 H15B 0.98 . ? C15 H15C 0.98 . ? C16 N3 1.490(17) . ? C16 C17 1.52(2) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.51(3) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? N1 P1 1.599(12) . ? N2 P1 1.643(12) . ? N3 P1 1.613(11) . ? P1 I1 2.455(4) . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? 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 114.3(14) . . ? C2 C1 H1A 108.7 . . ? N1 C1 H1A 108.7 . . ? C2 C1 H1B 108.7 . . ? N1 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? C1 C2 C3 110.9(15) . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 C5 114.4(13) . . ? N1 C4 H4A 108.7 . . ? C5 C4 H4A 108.7 . . ? N1 C4 H4B 108.7 . . ? C5 C4 H4B 108.7 . . ? H4A C4 H4B 107.6 . . ? C6 C5 C4 109.6(16) . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5B 109.7 . . ? C4 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 C7 N2 114.6(12) . . ? C8 C7 H7A 108.6 . . ? N2 C7 H7A 108.6 . . ? C8 C7 H7B 108.6 . . ? N2 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C7 C8 C9 108.0(14) . . ? C7 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? C7 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C11 110.9(16) . . ? N2 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? N2 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108 . . ? C12 C11 C10 110.8(19) . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 N3 115.1(14) . . ? C14 C13 H13A 108.5 . . ? N3 C13 H13A 108.5 . . ? C14 C13 H13B 108.5 . . ? N3 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C13 C14 C15 111.8(16) . . ? C13 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? C13 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C16 C17 113.7(12) . . ? N3 C16 H16A 108.8 . . ? C17 C16 H16A 108.8 . . ? N3 C16 H16B 108.8 . . ? C17 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C18 C17 C16 108.9(16) . . ? C18 C17 H17A 109.9 . . ? C16 C17 H17A 109.9 . . ? C18 C17 H17B 109.9 . . ? C16 C17 H17B 109.9 . . ? H17A C17 H17B 108.3 . . ? C4 N1 C1 114.4(12) . . ? C4 N1 P1 120.1(10) . . ? C1 N1 P1 125.5(10) . . ? C10 N2 C7 118.0(12) . . ? C10 N2 P1 128.8(11) . . ? C7 N2 P1 113.2(9) . . ? C16 N3 C13 116.1(12) . . ? C16 N3 P1 120.4(9) . . ? C13 N3 P1 123.0(10) . . ? N1 P1 N3 111.5(6) . . ? N1 P1 N2 108.5(6) . . ? N3 P1 N2 112.0(6) . . ? N1 P1 I1 106.4(5) . . ? N3 P1 I1 108.7(4) . . ? N2 P1 I1 109.6(5) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 173.4(15) . . . . ? N1 C4 C5 C6 -171.2(17) . . . . ? N2 C7 C8 C9 -178.9(13) . . . . ? N2 C10 C11 C12 178.2(18) . . . . ? N3 C13 C14 C15 177.5(15) . . . . ? N3 C16 C17 C18 174.5(17) . . . . ? C5 C4 N1 C1 -64.8(18) . . . . ? C5 C4 N1 P1 113.0(14) . . . . ? C2 C1 N1 C4 -67.7(19) . . . . ? C2 C1 N1 P1 114.6(16) . . . . ? C11 C10 N2 C7 -82.1(19) . . . . ? C11 C10 N2 P1 99.2(18) . . . . ? C8 C7 N2 C10 -62.7(18) . . . . ? C8 C7 N2 P1 116.1(13) . . . . ? C17 C16 N3 C13 -66.6(18) . . . . ? C17 C16 N3 P1 120.7(14) . . . . ? C14 C13 N3 C16 -69.4(19) . . . . ? C14 C13 N3 P1 103.1(16) . . . . ? C4 N1 P1 N3 -163.7(10) . . . . ? C1 N1 P1 N3 13.8(14) . . . . ? C4 N1 P1 N2 72.5(12) . . . . ? C1 N1 P1 N2 -110.0(13) . . . . ? C4 N1 P1 I1 -45.4(11) . . . . ? C1 N1 P1 I1 132.1(11) . . . . ? C16 N3 P1 N1 63.4(12) . . . . ? C13 N3 P1 N1 -108.8(12) . . . . ? C16 N3 P1 N2 -174.9(10) . . . . ? C13 N3 P1 N2 13.0(14) . . . . ? C16 N3 P1 I1 -53.6(11) . . . . ? C13 N3 P1 I1 134.2(11) . . . . ? C10 N2 P1 N1 9.0(16) . . . . ? C7 N2 P1 N1 -169.8(9) . . . . ? C10 N2 P1 N3 -114.5(14) . . . . ? C7 N2 P1 N3 66.8(11) . . . . ? C10 N2 P1 I1 124.8(14) . . . . ? C7 N2 P1 I1 -54.0(10) . . . . ? # Attachment 'Compound3.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-08-08 at 11:09:52 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : s dreduc sortav struct data_s3 _database_code_depnum_ccdc_archive 'CCDC 659627' _audit_creation_date 2006-08-08T11:09:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C12 H24 I2 N3 P1' _chemical_formula_sum 'C12 H24 I2 N3 P' _chemical_formula_weight 495.11 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 8.7268(4) _cell_length_b 21.6107(9) _cell_length_c 9.3212(4) _cell_angle_alpha 90 _cell_angle_beta 91.655(2) _cell_angle_gamma 90 _cell_volume 1757.17(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2947 _cell_measurement_theta_min 2 _cell_measurement_theta_max 26.5 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.872 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.661 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.711 _exptl_absorpt_correction_T_max 0.8381 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(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_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.848478E-1 _diffrn_orient_matrix_ub_12 0.522E-4 _diffrn_orient_matrix_ub_13 -0.698484E-1 _diffrn_orient_matrix_ub_21 0.768127E-1 _diffrn_orient_matrix_ub_22 -0.39649E-2 _diffrn_orient_matrix_ub_23 0.811816E-1 _diffrn_orient_matrix_ub_31 -0.65098E-2 _diffrn_orient_matrix_ub_32 -0.461032E-1 _diffrn_orient_matrix_ub_33 -0.70607E-2 _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 0.0520 _diffrn_reflns_av_unetI/netI 0.0502 _diffrn_reflns_number 14127 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 26.5 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.961 _diffrn_measured_fraction_theta_max 0.961 _reflns_number_total 3496 _reflns_number_gt 2606 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # 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 'SIR92 (Giacovazzo et al, 1993)' _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^)+(0.0282P)^2^+11.3854P] 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_number_reflns 3496 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_restrained_S_all 1.06 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.16 _refine_diff_density_min -0.837 _refine_diff_density_rms 0.162 #----------------------------------------------------------------------------# # 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' I I -0.4742 1.8119 '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 C1 C 0.2385(8) 0.1576(3) 0.5746(7) 0.0364(16) Uani 1 1 d . . . H1A H 0.1555 0.1518 0.6435 0.044 Uiso 1 1 calc R . . H1B H 0.224 0.1279 0.4944 0.044 Uiso 1 1 calc R . . C2 C 0.2421(9) 0.2237(3) 0.5199(9) 0.0458(19) Uani 1 1 d . . . H2A H 0.2046 0.2528 0.5929 0.055 Uiso 1 1 calc R . . H2B H 0.1787 0.2282 0.4308 0.055 Uiso 1 1 calc R . . C3 C 0.4130(9) 0.2350(4) 0.4912(8) 0.0447(19) Uani 1 1 d . . . H3A H 0.4415 0.217 0.398 0.054 Uiso 1 1 calc R . . H3B H 0.4367 0.2798 0.4911 0.054 Uiso 1 1 calc R . . C4 C 0.4950(8) 0.2029(3) 0.6135(7) 0.0346(15) Uani 1 1 d . . . H4A H 0.5971 0.1881 0.5849 0.042 Uiso 1 1 calc R . . H4B H 0.5078 0.2307 0.6973 0.042 Uiso 1 1 calc R . . C5 C 0.2916(8) 0.1786(3) 0.9567(7) 0.0398(17) Uani 1 1 d . . . H5A H 0.1899 0.1633 0.9227 0.048 Uiso 1 1 calc R . . H5B H 0.3135 0.2184 0.9087 0.048 Uiso 1 1 calc R . . C6 C 0.2985(11) 0.1854(4) 1.1171(8) 0.052(2) Uani 1 1 d . . . H6A H 0.1983 0.1989 1.1531 0.063 Uiso 1 1 calc R . . H6B H 0.3777 0.2159 1.1473 0.063 Uiso 1 1 calc R . . C7 C 0.3395(11) 0.1213(4) 1.1726(8) 0.056(2) Uani 1 1 d . . . H7A H 0.3892 0.1235 1.2693 0.067 Uiso 1 1 calc R . . H7B H 0.2473 0.0947 1.1769 0.067 Uiso 1 1 calc R . . C8 C 0.4486(10) 0.0971(4) 1.0645(8) 0.049(2) Uani 1 1 d . . . H8A H 0.5561 0.1041 1.0973 0.059 Uiso 1 1 calc R . . H8B H 0.4328 0.0522 1.0488 0.059 Uiso 1 1 calc R . . C9 C 0.7411(8) 0.1072(4) 0.8624(9) 0.050(2) Uani 1 1 d . . . H9A H 0.7543 0.0835 0.9528 0.06 Uiso 1 1 calc R . . H9B H 0.7232 0.1513 0.8857 0.06 Uiso 1 1 calc R . . C10 C 0.8771(10) 0.0999(5) 0.7698(12) 0.071(3) Uani 1 1 d . . . H10A H 0.8879 0.1361 0.7061 0.086 Uiso 1 1 calc R . . H10B H 0.9722 0.0954 0.8295 0.086 Uiso 1 1 calc R . . C11 C 0.8470(8) 0.0425(4) 0.6839(8) 0.0420(18) Uani 1 1 d . . . H11A H 0.8745 0.005 0.7399 0.05 Uiso 1 1 calc R . . H11B H 0.9054 0.0428 0.5944 0.05 Uiso 1 1 calc R . . C12 C 0.6759(8) 0.0451(4) 0.6512(8) 0.0395(17) Uani 1 1 d . . . H12A H 0.6539 0.0657 0.558 0.047 Uiso 1 1 calc R . . H12B H 0.6311 0.003 0.6485 0.047 Uiso 1 1 calc R . . N1 N 0.3925(6) 0.1499(2) 0.6465(6) 0.0284(12) Uani 1 1 d . . . N2 N 0.4128(6) 0.1325(2) 0.9300(6) 0.0323(13) Uani 1 1 d . . . N3 N 0.6142(6) 0.0818(3) 0.7718(5) 0.0299(12) Uani 1 1 d . . . P1 P 0.43680(18) 0.10234(7) 0.77362(17) 0.0261(4) Uani 1 1 d . . . I1 I 0.28129(5) 0.010227(19) 0.73480(5) 0.03143(14) Uani 1 1 d . . . I2 I 0.12951(6) -0.13953(2) 0.69027(6) 0.04684(17) 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 0.036(4) 0.041(4) 0.032(4) 0.007(3) -0.004(3) -0.007(3) C2 0.046(4) 0.037(4) 0.053(5) 0.013(4) -0.021(4) -0.002(3) C3 0.049(4) 0.044(4) 0.041(4) 0.010(3) -0.010(4) -0.017(4) C4 0.032(4) 0.033(4) 0.039(4) 0.005(3) -0.002(3) -0.004(3) C5 0.044(4) 0.040(4) 0.035(4) 0.000(3) 0.003(3) 0.018(3) C6 0.077(6) 0.043(5) 0.038(4) -0.002(4) 0.017(4) 0.024(4) C7 0.078(6) 0.054(5) 0.037(4) 0.003(4) 0.023(4) 0.019(5) C8 0.073(6) 0.040(4) 0.034(4) -0.002(3) 0.005(4) 0.018(4) C9 0.035(4) 0.059(5) 0.056(5) -0.018(4) -0.006(4) -0.008(4) C10 0.039(5) 0.077(7) 0.097(7) -0.032(6) -0.010(5) -0.006(4) C11 0.028(4) 0.049(5) 0.050(4) 0.002(4) 0.007(3) 0.002(3) C12 0.032(4) 0.048(4) 0.039(4) -0.014(3) 0.006(3) 0.005(3) N1 0.029(3) 0.027(3) 0.029(3) 0.004(2) 0.000(2) -0.004(2) N2 0.042(3) 0.024(3) 0.031(3) -0.005(2) -0.001(3) 0.007(2) N3 0.027(3) 0.035(3) 0.027(3) -0.007(2) -0.001(2) 0.002(2) P1 0.0251(8) 0.0258(8) 0.0273(8) -0.0017(7) 0.0015(7) 0.0000(7) I1 0.0276(2) 0.0286(2) 0.0380(3) 0.00016(19) -0.00010(17) -0.00216(18) I2 0.0537(3) 0.0348(3) 0.0513(3) 0.0069(2) -0.0097(2) -0.0143(2) #----------------------------------------------------------------------------# # 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 C1 N1 1.494(8) . ? C1 C2 1.516(10) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.543(11) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.499(9) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 N1 1.490(8) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 N2 1.478(8) . ? C5 C6 1.503(10) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.519(11) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.499(10) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 N2 1.494(9) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 N3 1.479(8) . ? C9 C10 1.496(12) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.495(12) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.516(9) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 N3 1.490(8) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? N1 P1 1.608(5) . ? N2 P1 1.617(5) . ? N3 P1 1.610(5) . ? P1 I1 2.4303(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 103.2(5) . . ? N1 C1 H1A 111.1 . . ? C2 C1 H1A 111.1 . . ? N1 C1 H1B 111.1 . . ? C2 C1 H1B 111.1 . . ? H1A C1 H1B 109.1 . . ? C1 C2 C3 103.8(6) . . ? C1 C2 H2A 111 . . ? C3 C2 H2A 111 . . ? C1 C2 H2B 111 . . ? C3 C2 H2B 111 . . ? H2A C2 H2B 109 . . ? C4 C3 C2 103.7(6) . . ? C4 C3 H3A 111 . . ? C2 C3 H3A 111 . . ? C4 C3 H3B 111 . . ? C2 C3 H3B 111 . . ? H3A C3 H3B 109 . . ? N1 C4 C3 103.7(5) . . ? N1 C4 H4A 111 . . ? C3 C4 H4A 111 . . ? N1 C4 H4B 111 . . ? C3 C4 H4B 111 . . ? H4A C4 H4B 109 . . ? N2 C5 C6 103.0(5) . . ? N2 C5 H5A 111.2 . . ? C6 C5 H5A 111.2 . . ? N2 C5 H5B 111.2 . . ? C6 C5 H5B 111.2 . . ? H5A C5 H5B 109.1 . . ? C5 C6 C7 104.6(6) . . ? C5 C6 H6A 110.8 . . ? C7 C6 H6A 110.8 . . ? C5 C6 H6B 110.8 . . ? C7 C6 H6B 110.8 . . ? H6A C6 H6B 108.9 . . ? C8 C7 C6 103.8(6) . . ? C8 C7 H7A 111 . . ? C6 C7 H7A 111 . . ? C8 C7 H7B 111 . . ? C6 C7 H7B 111 . . ? H7A C7 H7B 109 . . ? N2 C8 C7 105.3(6) . . ? N2 C8 H8A 110.7 . . ? C7 C8 H8A 110.7 . . ? N2 C8 H8B 110.7 . . ? C7 C8 H8B 110.7 . . ? H8A C8 H8B 108.8 . . ? N3 C9 C10 103.0(6) . . ? N3 C9 H9A 111.2 . . ? C10 C9 H9A 111.2 . . ? N3 C9 H9B 111.2 . . ? C10 C9 H9B 111.2 . . ? H9A C9 H9B 109.1 . . ? C11 C10 C9 105.5(7) . . ? C11 C10 H10A 110.6 . . ? C9 C10 H10A 110.6 . . ? C11 C10 H10B 110.6 . . ? C9 C10 H10B 110.6 . . ? H10A C10 H10B 108.8 . . ? C10 C11 C12 103.6(6) . . ? C10 C11 H11A 111 . . ? C12 C11 H11A 111 . . ? C10 C11 H11B 111 . . ? C12 C11 H11B 111 . . ? H11A C11 H11B 109 . . ? N3 C12 C11 104.1(5) . . ? N3 C12 H12A 110.9 . . ? C11 C12 H12A 110.9 . . ? N3 C12 H12B 110.9 . . ? C11 C12 H12B 110.9 . . ? H12A C12 H12B 109 . . ? C4 N1 C1 111.1(5) . . ? C4 N1 P1 120.7(4) . . ? C1 N1 P1 126.6(4) . . ? C5 N2 C8 109.7(5) . . ? C5 N2 P1 122.3(4) . . ? C8 N2 P1 121.4(4) . . ? C9 N3 C12 110.3(5) . . ? C9 N3 P1 126.6(5) . . ? C12 N3 P1 121.5(4) . . ? N1 P1 N3 112.3(3) . . ? N1 P1 N2 111.8(3) . . ? N3 P1 N2 105.7(3) . . ? N1 P1 I1 107.0(2) . . ? N3 P1 I1 107.8(2) . . ? N2 P1 I1 112.2(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 29.8(7) . . . . ? C1 C2 C3 C4 -38.9(8) . . . . ? C2 C3 C4 N1 31.7(7) . . . . ? N2 C5 C6 C7 -34.6(8) . . . . ? C5 C6 C7 C8 36.6(9) . . . . ? C6 C7 C8 N2 -23.8(9) . . . . ? N3 C9 C10 C11 -32.6(9) . . . . ? C9 C10 C11 C12 37.5(9) . . . . ? C10 C11 C12 N3 -26.8(8) . . . . ? C3 C4 N1 C1 -13.5(7) . . . . ? C3 C4 N1 P1 -179.8(5) . . . . ? C2 C1 N1 C4 -10.6(7) . . . . ? C2 C1 N1 P1 154.7(5) . . . . ? C6 C5 N2 C8 20.0(8) . . . . ? C6 C5 N2 P1 171.8(5) . . . . ? C7 C8 N2 C5 2.5(9) . . . . ? C7 C8 N2 P1 -149.6(6) . . . . ? C10 C9 N3 C12 15.6(9) . . . . ? C10 C9 N3 P1 -150.4(6) . . . . ? C11 C12 N3 C9 7.0(8) . . . . ? C11 C12 N3 P1 173.8(5) . . . . ? C4 N1 P1 N3 -44.5(6) . . . . ? C1 N1 P1 N3 151.4(5) . . . . ? C4 N1 P1 N2 74.1(6) . . . . ? C1 N1 P1 N2 -90.0(6) . . . . ? C4 N1 P1 I1 -162.6(4) . . . . ? C1 N1 P1 I1 33.3(6) . . . . ? C9 N3 P1 N1 99.2(6) . . . . ? C12 N3 P1 N1 -65.3(6) . . . . ? C9 N3 P1 N2 -23.0(7) . . . . ? C12 N3 P1 N2 172.5(5) . . . . ? C9 N3 P1 I1 -143.2(6) . . . . ? C12 N3 P1 I1 52.3(6) . . . . ? C5 N2 P1 N1 32.2(6) . . . . ? C8 N2 P1 N1 -179.2(6) . . . . ? C5 N2 P1 N3 154.6(5) . . . . ? C8 N2 P1 N3 -56.8(6) . . . . ? C5 N2 P1 I1 -88.2(5) . . . . ? C8 N2 P1 I1 60.5(6) . . . . ? # Attachment 'Compound6.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-06-25 at 18:15:46 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : nick dreduc sortav struct data_nick6 _database_code_depnum_ccdc_archive 'CCDC 659628' _audit_creation_date 2007-06-25T18:15:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H29 I1 N3 P1 Se1' _chemical_formula_sum 'C18 H29 I N3 P Se' _chemical_formula_weight 524.27 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 9.093(3) _cell_length_b 11.540(6) _cell_length_c 19.803(7) _cell_angle_alpha 90 _cell_angle_beta 95.386(13) _cell_angle_gamma 90 _cell_volume 2068.8(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2275 _cell_measurement_theta_min 2 _cell_measurement_theta_max 26 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.683 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.39 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.6483 _exptl_absorpt_correction_T_max 0.7973 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 150(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_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.524644E-1 _diffrn_orient_matrix_ub_12 -0.759224E-1 _diffrn_orient_matrix_ub_13 0.18886E-2 _diffrn_orient_matrix_ub_21 -0.317059E-1 _diffrn_orient_matrix_ub_22 0.210153E-1 _diffrn_orient_matrix_ub_23 0.454305E-1 _diffrn_orient_matrix_ub_31 -0.918892E-1 _diffrn_orient_matrix_ub_32 0.360969E-1 _diffrn_orient_matrix_ub_33 -0.224769E-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 0.067 _diffrn_reflns_av_unetI/netI 0.0885 _diffrn_reflns_number 13098 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.823 _diffrn_measured_fraction_theta_max 0.749 _reflns_number_total 3046 _reflns_number_gt 1668 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # 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 'SIR92 (Giacovazzo et al, 1993)' _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^)+(0.1462P)^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 none _refine_ls_number_reflns 3046 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1264 _refine_ls_R_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.2204 _refine_ls_wR_factor_gt 0.1825 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.955 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 2.785 _refine_diff_density_min -1.255 _refine_diff_density_rms 0.206 #----------------------------------------------------------------------------# # 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' I I -0.4742 1.8119 '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' H H 0 0 '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 C1 C 0.7008(15) 0.2391(10) 0.0447(5) 0.053(3) Uani 1 1 d . . . H1A H 0.5985 0.2149 0.051 0.064 Uiso 1 1 calc R . . H1B H 0.7442 0.1829 0.0145 0.064 Uiso 1 1 calc R . . C2 C 0.7032(15) 0.3596(11) 0.0159(6) 0.058(4) Uani 1 1 d . . . H2A H 0.6249 0.4083 0.0329 0.07 Uiso 1 1 calc R . . H2B H 0.6898 0.358 -0.0342 0.07 Uiso 1 1 calc R . . C3 C 0.8578(16) 0.4046(11) 0.0416(6) 0.054(3) Uani 1 1 d . . . H3A H 0.9349 0.3722 0.0149 0.065 Uiso 1 1 calc R . . H3B H 0.8623 0.4903 0.0403 0.065 Uiso 1 1 calc R . . C4 C 0.8731(15) 0.3590(10) 0.1145(6) 0.051(3) Uani 1 1 d . . . H4A H 0.9782 0.3467 0.1308 0.061 Uiso 1 1 calc R . . H4B H 0.8291 0.4139 0.1454 0.061 Uiso 1 1 calc R . . C5 C 0.9433(17) 0.0834(11) 0.2810(6) 0.058(4) Uani 1 1 d . . . H5A H 1.0479 0.065 0.2755 0.07 Uiso 1 1 calc R . . H5B H 0.8848 0.0109 0.2779 0.07 Uiso 1 1 calc R . . C6 C 0.9283(19) 0.1456(13) 0.3478(6) 0.070(4) Uani 1 1 d . . . H6A H 0.9029 0.0896 0.3827 0.084 Uiso 1 1 calc R . . H6B H 1.0225 0.1839 0.3639 0.084 Uiso 1 1 calc R . . C7 C 0.8117(18) 0.2314(12) 0.3356(6) 0.069(4) Uani 1 1 d . . . H7A H 0.8259 0.2957 0.3687 0.083 Uiso 1 1 calc R . . H7B H 0.7137 0.1959 0.3395 0.083 Uiso 1 1 calc R . . C8 C 0.8236(16) 0.2753(11) 0.2637(6) 0.058(4) Uani 1 1 d . . . H8A H 0.7259 0.2987 0.2417 0.07 Uiso 1 1 calc R . . H8B H 0.8926 0.3416 0.2634 0.07 Uiso 1 1 calc R . . C9 C 0.5778(16) 0.0555(11) 0.1883(7) 0.061(4) Uani 1 1 d . . . H9A H 0.5311 0.1316 0.1777 0.073 Uiso 1 1 calc R . . H9B H 0.6084 0.0516 0.2375 0.073 Uiso 1 1 calc R . . C10 C 0.4723(15) -0.0426(10) 0.1667(6) 0.053(3) Uani 1 1 d . . . H10A H 0.3684 -0.0195 0.1699 0.063 Uiso 1 1 calc R . . H10B H 0.4944 -0.1127 0.1946 0.063 Uiso 1 1 calc R . . C11 C 0.5028(16) -0.0628(12) 0.0930(6) 0.059(4) Uani 1 1 d . . . H11A H 0.4689 -0.1408 0.0775 0.07 Uiso 1 1 calc R . . H11B H 0.452 -0.0039 0.0628 0.07 Uiso 1 1 calc R . . C12 C 0.6651(16) -0.0525(11) 0.0933(6) 0.055(4) Uani 1 1 d . . . H12A H 0.6931 -0.0253 0.0489 0.066 Uiso 1 1 calc R . . H12B H 0.7144 -0.1274 0.1045 0.066 Uiso 1 1 calc R . . C13 C 1.1489(15) 0.1620(11) 0.1040(7) 0.057(4) Uani 1 1 d . . . C14 C 1.2200(15) 0.2105(12) 0.1619(6) 0.058(3) Uani 1 1 d . . . H14 H 1.2062 0.1793 0.2053 0.069 Uiso 1 1 calc R . . C15 C 1.3099(16) 0.3034(12) 0.1561(7) 0.062(4) Uani 1 1 d . . . H15 H 1.3599 0.3371 0.1956 0.074 Uiso 1 1 calc R . . C16 C 1.3292(17) 0.3495(14) 0.0920(9) 0.076(5) Uani 1 1 d . . . H16 H 1.389 0.4162 0.0879 0.092 Uiso 1 1 calc R . . C17 C 1.2603(17) 0.2971(12) 0.0350(7) 0.065(4) Uani 1 1 d . . . H17 H 1.2766 0.3255 -0.0087 0.078 Uiso 1 1 calc R . . C18 C 1.1687(16) 0.2044(11) 0.0410(7) 0.059(4) Uani 1 1 d . . . H18 H 1.1192 0.1697 0.0017 0.071 Uiso 1 1 calc R . . I1 I 0.38107(10) 0.11794(7) 0.34625(4) 0.0564(4) Uani 1 1 d . . . N1 N 0.7909(11) 0.2470(8) 0.1108(5) 0.049(3) Uani 1 1 d . . . N2 N 0.8831(11) 0.1702(8) 0.2294(4) 0.046(3) Uani 1 1 d . . . N3 N 0.7046(11) 0.0377(8) 0.1489(4) 0.045(2) Uani 1 1 d . . . P1 P 0.8365(4) 0.1311(3) 0.15279(15) 0.0443(8) Uani 1 1 d . . . Se1 Se 1.01848(16) 0.03006(11) 0.11240(7) 0.0549(5) 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 0.067(10) 0.047(8) 0.044(6) -0.001(5) -0.010(6) -0.002(6) C2 0.041(9) 0.080(10) 0.053(7) 0.009(6) 0.002(6) 0.011(7) C3 0.062(11) 0.056(8) 0.045(7) 0.005(6) 0.009(6) 0.002(6) C4 0.047(9) 0.050(8) 0.054(7) 0.008(6) 0.002(6) -0.001(6) C5 0.072(11) 0.062(8) 0.041(7) 0.011(6) 0.006(7) 0.014(7) C6 0.085(13) 0.087(11) 0.039(7) 0.003(7) 0.008(7) 0.004(9) C7 0.087(13) 0.061(9) 0.063(8) -0.017(7) 0.024(8) -0.006(8) C8 0.061(10) 0.066(9) 0.049(7) 0.009(6) 0.007(6) -0.007(7) C9 0.067(11) 0.051(8) 0.067(9) -0.002(7) 0.017(8) -0.011(7) C10 0.039(9) 0.052(8) 0.065(8) -0.007(6) -0.005(6) -0.013(6) C11 0.049(10) 0.066(9) 0.057(8) -0.004(6) -0.014(7) -0.015(7) C12 0.066(11) 0.057(9) 0.044(7) -0.007(6) 0.013(6) -0.006(7) C13 0.051(10) 0.057(8) 0.063(8) -0.006(6) 0.008(7) 0.012(7) C14 0.046(10) 0.070(10) 0.057(8) -0.002(7) 0.006(6) 0.005(7) C15 0.063(11) 0.063(9) 0.057(8) 0.001(7) -0.012(7) 0.003(7) C16 0.038(10) 0.083(11) 0.110(13) 0.020(10) 0.010(9) 0.003(8) C17 0.064(11) 0.065(10) 0.072(9) 0.010(8) 0.032(8) 0.021(8) C18 0.058(10) 0.058(9) 0.061(8) 0.022(6) 0.011(7) 0.005(7) I1 0.0561(7) 0.0612(6) 0.0522(5) 0.0014(4) 0.0069(4) -0.0037(4) N1 0.035(7) 0.059(7) 0.052(6) -0.003(5) -0.003(5) -0.003(5) N2 0.048(7) 0.049(6) 0.040(5) -0.004(4) 0.002(5) 0.010(5) N3 0.045(8) 0.047(6) 0.045(5) -0.003(4) 0.009(5) -0.003(5) P1 0.045(2) 0.0454(19) 0.0427(16) -0.0019(14) 0.0029(15) 0.0014(15) Se1 0.0555(10) 0.0484(8) 0.0624(8) -0.0033(6) 0.0143(7) 0.0034(6) #----------------------------------------------------------------------------# # 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 C1 N1 1.480(13) . ? C1 C2 1.503(16) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.540(18) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.531(16) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 N1 1.491(14) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 N2 1.498(15) . ? C5 C6 1.521(17) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 C7 1.454(19) . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.525(16) . ? C7 H7A 0.99 . ? C7 H7B 0.99 . ? C8 N2 1.515(15) . ? C8 H8A 0.99 . ? C8 H8B 0.99 . ? C9 N3 1.466(16) . ? C9 C10 1.518(17) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.529(17) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.480(17) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 N3 1.533(14) . ? C12 H12A 0.99 . ? C12 H12B 0.99 . ? C13 C18 1.366(17) . ? C13 C14 1.382(17) . ? C13 Se1 1.947(14) . ? C14 C15 1.360(18) . ? C14 H14 0.95 . ? C15 C16 1.40(2) . ? C15 H15 0.95 . ? C16 C17 1.377(19) . ? C16 H16 0.95 . ? C17 C18 1.369(19) . ? C17 H17 0.95 . ? C18 H18 0.95 . ? N1 P1 1.608(10) . ? N2 P1 1.601(9) . ? N3 P1 1.609(10) . ? P1 Se1 2.233(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 104.6(10) . . ? N1 C1 H1A 110.8 . . ? C2 C1 H1A 110.8 . . ? N1 C1 H1B 110.8 . . ? C2 C1 H1B 110.8 . . ? H1A C1 H1B 108.9 . . ? C1 C2 C3 103.4(10) . . ? C1 C2 H2A 111.1 . . ? C3 C2 H2A 111.1 . . ? C1 C2 H2B 111.1 . . ? C3 C2 H2B 111.1 . . ? H2A C2 H2B 109 . . ? C4 C3 C2 101.2(10) . . ? C4 C3 H3A 111.5 . . ? C2 C3 H3A 111.5 . . ? C4 C3 H3B 111.5 . . ? C2 C3 H3B 111.5 . . ? H3A C3 H3B 109.4 . . ? N1 C4 C3 104.5(9) . . ? N1 C4 H4A 110.8 . . ? C3 C4 H4A 110.8 . . ? N1 C4 H4B 110.8 . . ? C3 C4 H4B 110.8 . . ? H4A C4 H4B 108.9 . . ? N2 C5 C6 102.7(10) . . ? N2 C5 H5A 111.2 . . ? C6 C5 H5A 111.2 . . ? N2 C5 H5B 111.2 . . ? C6 C5 H5B 111.2 . . ? H5A C5 H5B 109.1 . . ? C7 C6 C5 107.6(11) . . ? C7 C6 H6A 110.2 . . ? C5 C6 H6A 110.2 . . ? C7 C6 H6B 110.2 . . ? C5 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? C6 C7 C8 105.4(12) . . ? C6 C7 H7A 110.7 . . ? C8 C7 H7A 110.7 . . ? C6 C7 H7B 110.7 . . ? C8 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? N2 C8 C7 102.3(10) . . ? N2 C8 H8A 111.3 . . ? C7 C8 H8A 111.3 . . ? N2 C8 H8B 111.3 . . ? C7 C8 H8B 111.3 . . ? H8A C8 H8B 109.2 . . ? N3 C9 C10 104.7(10) . . ? N3 C9 H9A 110.8 . . ? C10 C9 H9A 110.8 . . ? N3 C9 H9B 110.8 . . ? C10 C9 H9B 110.8 . . ? H9A C9 H9B 108.9 . . ? C9 C10 C11 102.5(10) . . ? C9 C10 H10A 111.3 . . ? C11 C10 H10A 111.3 . . ? C9 C10 H10B 111.3 . . ? C11 C10 H10B 111.3 . . ? H10A C10 H10B 109.2 . . ? C12 C11 C10 104.7(10) . . ? C12 C11 H11A 110.8 . . ? C10 C11 H11A 110.8 . . ? C12 C11 H11B 110.8 . . ? C10 C11 H11B 110.8 . . ? H11A C11 H11B 108.9 . . ? C11 C12 N3 103.0(10) . . ? C11 C12 H12A 111.2 . . ? N3 C12 H12A 111.2 . . ? C11 C12 H12B 111.2 . . ? N3 C12 H12B 111.2 . . ? H12A C12 H12B 109.1 . . ? C18 C13 C14 121.5(13) . . ? C18 C13 Se1 119.4(10) . . ? C14 C13 Se1 119.1(10) . . ? C15 C14 C13 119.1(12) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 120.3(13) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C17 C16 C15 119.2(14) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C18 C17 C16 120.4(13) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C13 C18 C17 119.5(14) . . ? C13 C18 H18 120.3 . . ? C17 C18 H18 120.3 . . ? C1 N1 C4 109.3(9) . . ? C1 N1 P1 120.0(8) . . ? C4 N1 P1 126.3(8) . . ? C5 N2 C8 110.6(8) . . ? C5 N2 P1 120.4(8) . . ? C8 N2 P1 125.2(8) . . ? C9 N3 C12 109.5(9) . . ? C9 N3 P1 120.1(8) . . ? C12 N3 P1 127.8(8) . . ? N2 P1 N3 111.3(5) . . ? N2 P1 N1 106.7(5) . . ? N3 P1 N1 112.2(5) . . ? N2 P1 Se1 110.3(4) . . ? N3 P1 Se1 102.0(4) . . ? N1 P1 Se1 114.4(4) . . ? C13 Se1 P1 95.8(4) . . ? 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 33.6(13) . . . . ? C1 C2 C3 C4 -41.2(12) . . . . ? C2 C3 C4 N1 33.1(12) . . . . ? N2 C5 C6 C7 24.1(16) . . . . ? C5 C6 C7 C8 -34.8(17) . . . . ? C6 C7 C8 N2 30.3(15) . . . . ? N3 C9 C10 C11 -31.4(13) . . . . ? C9 C10 C11 C12 40.4(14) . . . . ? C10 C11 C12 N3 -32.5(13) . . . . ? C18 C13 C14 C15 1(2) . . . . ? Se1 C13 C14 C15 -179.4(10) . . . . ? C13 C14 C15 C16 0(2) . . . . ? C14 C15 C16 C17 -2(2) . . . . ? C15 C16 C17 C18 3(2) . . . . ? C14 C13 C18 C17 0(2) . . . . ? Se1 C13 C18 C17 -180.0(10) . . . . ? C16 C17 C18 C13 -2(2) . . . . ? C2 C1 N1 C4 -12.7(13) . . . . ? C2 C1 N1 P1 -170.6(9) . . . . ? C3 C4 N1 C1 -13.3(13) . . . . ? C3 C4 N1 P1 142.8(10) . . . . ? C6 C5 N2 C8 -4.3(15) . . . . ? C6 C5 N2 P1 -163.6(10) . . . . ? C7 C8 N2 C5 -15.6(14) . . . . ? C7 C8 N2 P1 142.5(10) . . . . ? C10 C9 N3 C12 12.0(13) . . . . ? C10 C9 N3 P1 174.9(8) . . . . ? C11 C12 N3 C9 13.0(13) . . . . ? C11 C12 N3 P1 -148.3(9) . . . . ? C5 N2 P1 N3 62.1(11) . . . . ? C8 N2 P1 N3 -93.9(10) . . . . ? C5 N2 P1 N1 -175.2(10) . . . . ? C8 N2 P1 N1 28.8(11) . . . . ? C5 N2 P1 Se1 -50.4(10) . . . . ? C8 N2 P1 Se1 153.6(9) . . . . ? C9 N3 P1 N2 44.6(11) . . . . ? C12 N3 P1 N2 -155.9(10) . . . . ? C9 N3 P1 N1 -75.0(10) . . . . ? C12 N3 P1 N1 84.5(11) . . . . ? C9 N3 P1 Se1 162.2(9) . . . . ? C12 N3 P1 Se1 -38.3(10) . . . . ? C1 N1 P1 N2 -161.4(9) . . . . ? C4 N1 P1 N2 44.8(11) . . . . ? C1 N1 P1 N3 -39.2(11) . . . . ? C4 N1 P1 N3 167.0(9) . . . . ? C1 N1 P1 Se1 76.3(10) . . . . ? C4 N1 P1 Se1 -77.5(10) . . . . ? C18 C13 Se1 P1 -107.2(11) . . . . ? C14 C13 Se1 P1 73.1(10) . . . . ? N2 P1 Se1 C13 -72.3(6) . . . . ? N3 P1 Se1 C13 169.3(5) . . . . ? N1 P1 Se1 C13 48.0(5) . . . . ? # Attachment 'Compound7.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-08-17 at 17:09:47 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : smg28c absorb sortav struct data_smg28c _database_code_depnum_ccdc_archive 'CCDC 659629' _audit_creation_date 2007-08-17T17:09:47-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H30 I1 N2 P1 Se1' _chemical_formula_sum 'C18 H30 I N2 P Se' _chemical_formula_weight 511.27 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _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 12.8871(2) _cell_length_b 8.1610(2) _cell_length_c 19.7450(4) _cell_angle_alpha 90 _cell_angle_beta 91.0580(10) _cell_angle_gamma 90 _cell_volume 2076.26(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12947 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.374 _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 0.6019 _exptl_absorpt_correction_T_max 0.6673 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0848 _diffrn_reflns_av_unetI/netI 0.0742 _diffrn_reflns_number 22758 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 27.4 _diffrn_reflns_theta_full 27.4 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 4701 _reflns_number_gt 3311 _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^)+(0.0000P)^2^+4.2013P] 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 SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.00113(14) _refine_ls_number_reflns 4701 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0865 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.0709 _refine_ls_wR_factor_gt 0.0613 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.736 _refine_diff_density_min -0.626 _refine_diff_density_rms 0.141 #----------------------------------------------------------------------------# # 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' I I -0.4742 1.8119 '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 C2 C 0.2823(4) 0.1896(7) 0.4679(2) 0.0324(12) Uani 1 1 d . . . C3 C 0.3988(5) 0.1878(8) 0.4822(3) 0.0496(16) Uani 1 1 d . . . C4 C 0.4452(4) 0.1276(6) 0.4166(3) 0.0427(15) Uani 1 1 d . . . C5 C 0.3816(4) 0.2152(7) 0.3639(3) 0.0319(12) Uani 1 1 d . . . C7 C 0.2297(4) 0.4319(6) 0.2604(2) 0.0309(12) Uani 1 1 d . . . C8 C 0.2660(5) 0.4165(7) 0.1886(3) 0.0395(13) Uani 1 1 d . . . C9 C 0.1802(5) 0.3135(7) 0.1555(3) 0.0389(14) Uani 1 1 d . . . C10 C 0.1486(4) 0.1906(6) 0.2092(2) 0.0263(11) Uani 1 1 d . . . C11 C 0.0557(3) 0.2817(5) 0.3899(2) 0.0205(9) Uani 1 1 d . . . C12 C 0.0767(4) 0.4621(6) 0.4057(3) 0.0315(12) Uani 1 1 d . . . C13 C 0.0221(4) 0.1932(7) 0.4544(3) 0.0313(12) Uani 1 1 d . . . C14 C -0.0321(4) 0.2678(7) 0.3372(3) 0.0302(11) Uani 1 1 d . . . C15 C 0.2649(3) -0.1690(5) 0.3365(2) 0.0205(10) Uani 1 1 d . . . C16 C 0.3202(4) -0.1680(5) 0.2770(2) 0.0273(11) Uani 1 1 d . . . C17 C 0.4161(4) -0.2441(6) 0.2755(3) 0.0352(12) Uani 1 1 d . . . C18 C 0.4548(4) -0.3224(6) 0.3325(3) 0.0352(13) Uani 1 1 d . . . C19 C 0.3982(4) -0.3264(5) 0.3908(3) 0.0312(12) Uani 1 1 d . . . C20 C 0.3032(3) -0.2488(5) 0.3935(2) 0.0245(10) Uani 1 1 d . . . N1 N 0.2754(3) 0.2245(4) 0.39336(17) 0.0211(8) Uani 1 1 d . . . N6 N 0.1877(3) 0.2643(4) 0.27403(16) 0.0209(8) Uani 1 1 d . . . P1 P 0.17006(8) 0.19135(13) 0.34960(5) 0.0170(2) Uani 1 1 d . . . Se1 Se 0.12753(3) -0.07586(5) 0.34007(2) 0.02237(13) Uani 1 1 d . . . I1 I 0.29805(2) -0.09871(4) 0.079092(15) 0.03012(12) Uani 1 1 d . . . H2A H 0.255(3) 0.269(5) 0.493(2) 0.026(13) Uiso 1 1 d . . . H2B H 0.245(3) 0.078(5) 0.477(2) 0.029(12) Uiso 1 1 d . . . H3A H 0.427(4) 0.294(7) 0.490(3) 0.054(17) Uiso 1 1 d . . . H3B H 0.409(4) 0.119(7) 0.516(3) 0.055(18) Uiso 1 1 d . . . H4A H 0.517(4) 0.153(6) 0.415(2) 0.049(16) Uiso 1 1 d . . . H4B H 0.436(4) 0.003(6) 0.412(2) 0.052(15) Uiso 1 1 d . . . H5A H 0.408(3) 0.324(6) 0.360(2) 0.029(13) Uiso 1 1 d . . . H5B H 0.375(3) 0.165(5) 0.323(2) 0.028(13) Uiso 1 1 d . . . H7A H 0.283(3) 0.454(5) 0.294(2) 0.029(12) Uiso 1 1 d . . . H7B H 0.168(4) 0.513(6) 0.264(2) 0.040(14) Uiso 1 1 d . . . H8A H 0.334(4) 0.350(6) 0.190(3) 0.063(17) Uiso 1 1 d . . . H8B H 0.269(3) 0.514(6) 0.168(2) 0.037(14) Uiso 1 1 d . . . H9A H 0.128(4) 0.387(7) 0.145(3) 0.053(16) Uiso 1 1 d . . . H9B H 0.202(3) 0.254(5) 0.118(2) 0.027(12) Uiso 1 1 d . . . H10A H 0.070(4) 0.179(5) 0.209(2) 0.035(13) Uiso 1 1 d . . . H10B H 0.184(3) 0.093(5) 0.2034(19) 0.019(11) Uiso 1 1 d . . . H12A H 0.099(4) 0.522(6) 0.369(3) 0.054(17) Uiso 1 1 d . . . H12B H 0.012(4) 0.516(5) 0.422(2) 0.035(13) Uiso 1 1 d . . . H12C H 0.131(3) 0.479(5) 0.437(2) 0.016(11) Uiso 1 1 d . . . H13A H -0.043(3) 0.242(5) 0.474(2) 0.035(13) Uiso 1 1 d . . . H13B H 0.013(3) 0.071(6) 0.445(2) 0.036(13) Uiso 1 1 d . . . H13C H 0.069(4) 0.211(6) 0.490(3) 0.045(16) Uiso 1 1 d . . . H14A H -0.097(3) 0.310(5) 0.357(2) 0.027(12) Uiso 1 1 d . . . H14B H -0.015(4) 0.328(6) 0.296(3) 0.043(15) Uiso 1 1 d . . . H14C H -0.046(4) 0.153(7) 0.322(3) 0.059(17) Uiso 1 1 d . . . H16 H 0.293(3) -0.124(5) 0.236(2) 0.016(11) Uiso 1 1 d . . . H17 H 0.452(4) -0.245(6) 0.236(2) 0.041(15) Uiso 1 1 d . . . H18 H 0.517(4) -0.364(6) 0.332(2) 0.045(15) Uiso 1 1 d . . . H19 H 0.423(3) -0.369(5) 0.428(2) 0.031(14) Uiso 1 1 d . . . H20 H 0.265(3) -0.247(5) 0.438(2) 0.030(12) Uiso 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 C2 0.041(3) 0.035(3) 0.021(3) -0.003(2) -0.015(2) 0.003(3) C3 0.049(4) 0.038(4) 0.060(4) 0.004(3) -0.027(3) 0.002(3) C4 0.025(3) 0.024(3) 0.079(4) 0.002(3) -0.014(3) 0.001(2) C5 0.019(3) 0.028(3) 0.049(4) -0.010(3) -0.001(2) -0.009(2) C7 0.044(3) 0.022(3) 0.026(3) 0.002(2) -0.003(2) -0.014(2) C8 0.053(4) 0.033(3) 0.034(3) 0.018(3) 0.012(3) 0.006(3) C9 0.066(4) 0.030(3) 0.021(3) 0.003(2) 0.008(3) 0.018(3) C10 0.038(3) 0.024(3) 0.017(2) -0.001(2) -0.003(2) 0.005(2) C11 0.023(2) 0.021(2) 0.017(2) -0.0007(18) 0.0020(18) 0.0003(19) C12 0.034(3) 0.025(3) 0.036(3) -0.007(2) 0.008(3) 0.006(2) C13 0.032(3) 0.035(3) 0.027(3) 0.000(2) 0.011(2) 0.006(2) C14 0.024(3) 0.033(3) 0.034(3) -0.003(2) -0.001(2) 0.006(2) C15 0.022(2) 0.012(2) 0.028(2) -0.0025(18) 0.000(2) -0.0040(17) C16 0.037(3) 0.023(3) 0.022(3) 0.004(2) 0.001(2) 0.004(2) C17 0.032(3) 0.030(3) 0.043(3) 0.002(3) 0.010(3) -0.001(2) C18 0.017(3) 0.024(3) 0.064(4) 0.005(3) -0.008(3) 0.000(2) C19 0.038(3) 0.015(2) 0.040(3) 0.002(2) -0.017(3) -0.005(2) C20 0.030(3) 0.018(2) 0.025(3) 0.002(2) -0.004(2) -0.005(2) N1 0.022(2) 0.0185(19) 0.0222(19) 0.0005(15) -0.0044(16) -0.0007(15) N6 0.031(2) 0.021(2) 0.0107(17) -0.0013(15) 0.0029(15) -0.0073(16) P1 0.0199(6) 0.0152(6) 0.0160(6) -0.0017(4) -0.0002(5) -0.0018(5) Se1 0.0219(2) 0.0170(2) 0.0282(3) -0.0019(2) -0.00046(19) -0.00287(19) I1 0.0335(2) 0.03419(19) 0.02290(17) 0.00073(14) 0.00555(13) 0.00519(15) #----------------------------------------------------------------------------# # 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 C2 N1 1.501(6) . ? C2 C3 1.522(7) . ? C2 H2A 0.89(4) . ? C2 H2B 1.05(4) . ? C3 C4 1.518(8) . ? C3 H3A 0.95(5) . ? C3 H3B 0.89(5) . ? C4 C5 1.496(7) . ? C4 H4A 0.94(5) . ? C4 H4B 1.03(5) . ? C5 N1 1.499(6) . ? C5 H5A 0.95(4) . ? C5 H5B 0.92(4) . ? C7 N6 1.497(5) . ? C7 C8 1.507(7) . ? C7 H7A 0.96(4) . ? C7 H7B 1.04(5) . ? C8 C9 1.526(8) . ? C8 H8A 1.04(5) . ? C8 H8B 0.90(5) . ? C9 C10 1.521(7) . ? C9 H9A 0.92(5) . ? C9 H9B 0.94(4) . ? C10 N6 1.493(5) . ? C10 H10A 1.02(5) . ? C10 H10B 0.92(4) . ? C11 C14 1.528(6) . ? C11 C12 1.528(6) . ? C11 C13 1.535(6) . ? C11 P1 1.842(4) . ? C12 H12A 0.93(5) . ? C12 H12B 1.00(5) . ? C12 H12C 0.94(4) . ? C13 H13A 1.01(5) . ? C13 H13B 1.02(5) . ? C13 H13C 0.93(5) . ? C14 H14A 1.00(4) . ? C14 H14B 0.98(5) . ? C14 H14C 1.00(5) . ? C15 C20 1.383(6) . ? C15 C16 1.386(6) . ? C15 Se1 1.929(4) . ? C16 C17 1.385(6) . ? C16 H16 0.95(4) . ? C17 C18 1.380(7) . ? C17 H17 0.92(5) . ? C18 C19 1.375(7) . ? C18 H18 0.87(5) . ? C19 C20 1.381(6) . ? C19 H19 0.87(4) . ? C20 H20 1.02(4) . ? N1 P1 1.619(3) . ? N6 P1 1.626(3) . ? P1 Se1 2.2556(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 102.9(4) . . ? N1 C2 H2A 113(3) . . ? C3 C2 H2A 107(3) . . ? N1 C2 H2B 108(2) . . ? C3 C2 H2B 114(2) . . ? H2A C2 H2B 111(4) . . ? C4 C3 C2 104.4(5) . . ? C4 C3 H3A 106(3) . . ? C2 C3 H3A 113(3) . . ? C4 C3 H3B 113(3) . . ? C2 C3 H3B 106(4) . . ? H3A C3 H3B 114(5) . . ? C5 C4 C3 102.7(4) . . ? C5 C4 H4A 113(3) . . ? C3 C4 H4A 111(3) . . ? C5 C4 H4B 111(3) . . ? C3 C4 H4B 110(3) . . ? H4A C4 H4B 109(4) . . ? C4 C5 N1 104.2(4) . . ? C4 C5 H5A 108(3) . . ? N1 C5 H5A 109(3) . . ? C4 C5 H5B 116(3) . . ? N1 C5 H5B 107(3) . . ? H5A C5 H5B 112(4) . . ? N6 C7 C8 102.3(4) . . ? N6 C7 H7A 108(2) . . ? C8 C7 H7A 115(3) . . ? N6 C7 H7B 107(3) . . ? C8 C7 H7B 112(3) . . ? H7A C7 H7B 112(4) . . ? C7 C8 C9 102.3(4) . . ? C7 C8 H8A 108(3) . . ? C9 C8 H8A 109(3) . . ? C7 C8 H8B 112(3) . . ? C9 C8 H8B 110(3) . . ? H8A C8 H8B 116(4) . . ? C10 C9 C8 105.5(4) . . ? C10 C9 H9A 112(3) . . ? C8 C9 H9A 105(3) . . ? C10 C9 H9B 108(3) . . ? C8 C9 H9B 114(3) . . ? H9A C9 H9B 113(4) . . ? N6 C10 C9 104.0(4) . . ? N6 C10 H10A 111(2) . . ? C9 C10 H10A 110(2) . . ? N6 C10 H10B 107(2) . . ? C9 C10 H10B 110(2) . . ? H10A C10 H10B 114(3) . . ? C14 C11 C12 109.7(4) . . ? C14 C11 C13 108.3(4) . . ? C12 C11 C13 109.6(4) . . ? C14 C11 P1 105.3(3) . . ? C12 C11 P1 109.5(3) . . ? C13 C11 P1 114.2(3) . . ? C11 C12 H12A 114(3) . . ? C11 C12 H12B 110(3) . . ? H12A C12 H12B 107(4) . . ? C11 C12 H12C 114(2) . . ? H12A C12 H12C 101(4) . . ? H12B C12 H12C 110(4) . . ? C11 C13 H13A 112(2) . . ? C11 C13 H13B 110(3) . . ? H13A C13 H13B 111(4) . . ? C11 C13 H13C 111(3) . . ? H13A C13 H13C 101(4) . . ? H13B C13 H13C 111(4) . . ? C11 C14 H14A 109(2) . . ? C11 C14 H14B 110(3) . . ? H14A C14 H14B 111(4) . . ? C11 C14 H14C 114(3) . . ? H14A C14 H14C 107(4) . . ? H14B C14 H14C 106(4) . . ? C20 C15 C16 120.8(4) . . ? C20 C15 Se1 118.0(3) . . ? C16 C15 Se1 121.0(3) . . ? C17 C16 C15 119.3(5) . . ? C17 C16 H16 118(2) . . ? C15 C16 H16 123(2) . . ? C18 C17 C16 120.0(5) . . ? C18 C17 H17 121(3) . . ? C16 C17 H17 119(3) . . ? C19 C18 C17 120.4(5) . . ? C19 C18 H18 121(3) . . ? C17 C18 H18 119(3) . . ? C18 C19 C20 120.4(5) . . ? C18 C19 H19 122(3) . . ? C20 C19 H19 117(3) . . ? C19 C20 C15 119.2(4) . . ? C19 C20 H20 119(2) . . ? C15 C20 H20 122(2) . . ? C5 N1 C2 109.5(4) . . ? C5 N1 P1 123.2(3) . . ? C2 N1 P1 121.7(3) . . ? C10 N6 C7 109.3(3) . . ? C10 N6 P1 126.0(3) . . ? C7 N6 P1 123.8(3) . . ? N1 P1 N6 107.39(18) . . ? N1 P1 C11 111.86(18) . . ? N6 P1 C11 112.10(19) . . ? N1 P1 Se1 113.97(13) . . ? N6 P1 Se1 108.37(13) . . ? C11 P1 Se1 103.19(14) . . ? C15 Se1 P1 99.35(12) . . ?