Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Stephen Godfrey' _publ_contact_author_address ; Department of Chemistry (North Campus) University of Manchester Faraday Building Sackville Street PO Box 88 Manchester M60 1QD UK ; _publ_contact_author_email STEPHEN.GODFREY@MANCHESTER.AC.UK _publ_section_title ; The reaction of tertiary phosphines with (Ph2Se2I2)2 - the influence of steric and electronic effects. ; _publ_requested_category FO loop_ _publ_author_name 'Stephen Godfrey' 'Nicholas A. Barnes' 'Ruth T. A. Halton' 'Imrana Mustaq' 'Robin Gavin Pritchard' # Attachment 'Me3PSePhI.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2005-07-03 at 12:24:18 # 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 : new dreduc sortav struct data_new _database_code_depnum_ccdc_archive 'CCDC 279361' _audit_creation_date 2005-07-03T12:24:18-00:00 _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 'C19 H30 Cl2 I2 P2 Se2' _chemical_formula_sum 'C19 H30 Cl2 I2 P2 Se2' _chemical_formula_weight 802.99 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'A b a 2' _symmetry_space_group_name_Hall 'A 2 -2ac' _symmetry_Int_Tables_number 41 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y, z+1/2' 'x+1/2, -y, z+1/2' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1' 'x+1/2, -y+1/2, z+1' _cell_length_a 12.0129(3) _cell_length_b 20.2339(4) _cell_length_c 11.7239(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2849.70(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8440 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 1.872 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1528 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 5.066 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.4306 _exptl_absorpt_correction_T_max 0.7181 #----------------------------------------------------------------------------# # 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 0.546048E-1 _diffrn_orient_matrix_ub_12 -0.85857E-2 _diffrn_orient_matrix_ub_13 0.622934E-1 _diffrn_orient_matrix_ub_21 -0.654786E-1 _diffrn_orient_matrix_ub_22 -0.89862E-2 _diffrn_orient_matrix_ub_23 0.511547E-1 _diffrn_orient_matrix_ub_31 0.0025 _diffrn_orient_matrix_ub_32 -0.478338E-1 _diffrn_orient_matrix_ub_33 -0.207911E-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 0.030 _diffrn_reflns_av_unetI/netI 0.0304 _diffrn_reflns_number 12242 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 29.11 _diffrn_reflns_theta_full 29.11 _diffrn_measured_fraction_theta_full 0.957 _diffrn_measured_fraction_theta_max 0.957 _reflns_number_total 3343 _reflns_number_gt 3185 _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. Structure refined as a racemic twin so that the value reported as the Flack parameter is actually the fraction of one of the enantiomeric structures i.e. ratio 0.6 : 0.4 Also the high value for unique reflections is because Friedel pairs have not been merged in this non-centrosymmetric structure. ; _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^)+(0.0174P)^2^+3.5825P] 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 0.00105(6) _refine_ls_number_reflns 3345 _refine_ls_number_parameters 194 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0481 _refine_ls_wR_factor_gt 0.0473 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.006 _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 0.599(9) _refine_diff_density_max 0.506 _refine_diff_density_min -0.636 _refine_diff_density_rms 0.091 #----------------------------------------------------------------------------# # 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' 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' Cl Cl 0.1484 0.1585 '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 0.2996(3) 0.59273(16) 0.3490(3) 0.0234(7) Uani 1 1 d . . . C2 C 0.2137(4) 0.55435(19) 0.3931(4) 0.0365(9) Uani 1 1 d . . . C3 C 0.1942(4) 0.4927(2) 0.3444(5) 0.0533(13) Uani 1 1 d . . . C4 C 0.2593(5) 0.4713(2) 0.2551(5) 0.0505(13) Uani 1 1 d . . . C5 C 0.3426(4) 0.5094(2) 0.2117(4) 0.0398(11) Uani 1 1 d . . . C6 C 0.3644(3) 0.57143(18) 0.2589(3) 0.0289(8) Uani 1 1 d . . . C7 C 0.1306(3) 0.68786(19) 0.2292(3) 0.0275(7) Uani 1 1 d . . . C8 C 0.3189(3) 0.7768(2) 0.1968(4) 0.0290(8) Uani 1 1 d . . . C9 C 0.1574(3) 0.80161(19) 0.3759(3) 0.0269(8) Uani 1 1 d . . . P1 P 0.23050(7) 0.73857(4) 0.29942(7) 0.01946(18) Uani 1 1 d . . . Se1 Se 0.33177(3) 0.677664(16) 0.41818(3) 0.02595(9) Uani 1 1 d . . . I1 I 0.447773(16) 0.839730(9) 0.52157(2) 0.02359(7) Uani 1 1 d . . . C10 C 0.5379(9) 0.5051(6) 0.5111(16) 0.075(5) Uani 0.5 1 d P A 1 H10A H 0.619 0.4979 0.5193 0.09 Uiso 0.5 1 calc PR A 1 H10B H 0.523 0.5142 0.4295 0.09 Uiso 0.5 1 calc PR A 1 Cl1A Cl 0.5031(5) 0.5728(3) 0.5867(4) 0.0529(13) Uani 0.5 1 d P . 1 Cl1B Cl 0.4692(6) 0.4319(3) 0.5484(5) 0.0756(19) Uani 0.5 1 d P . 1 H2 H 0.168(4) 0.573(2) 0.453(4) 0.035(12) Uiso 1 1 d . . . H3 H 0.144(4) 0.467(2) 0.386(4) 0.045(13) Uiso 1 1 d . . . H4 H 0.242(5) 0.428(3) 0.235(5) 0.068(17) Uiso 1 1 d . . . H5 H 0.388(4) 0.494(2) 0.152(4) 0.049(13) Uiso 1 1 d . . . H6 H 0.421(5) 0.600(3) 0.229(4) 0.058(15) Uiso 1 1 d . . . H7A H 0.085(4) 0.671(2) 0.290(5) 0.048(14) Uiso 1 1 d . . . H7B H 0.091(4) 0.715(2) 0.179(4) 0.030(11) Uiso 1 1 d . . . H7C H 0.168(3) 0.6532(18) 0.179(4) 0.023(10) Uiso 1 1 d . . . H8A H 0.359(3) 0.744(2) 0.160(4) 0.032(11) Uiso 1 1 d . . . H8B H 0.364(4) 0.806(3) 0.240(4) 0.045(13) Uiso 1 1 d . . . H9A H 0.102(4) 0.779(2) 0.426(4) 0.041(11) Uiso 1 1 d . . . H9B H 0.218(4) 0.8295(18) 0.418(4) 0.033(11) Uiso 1 1 d . . . H9C H 0.113(4) 0.823(2) 0.322(4) 0.032(11) Uiso 1 1 d . . . H8C H 0.267(5) 0.802(3) 0.146(5) 0.072(17) 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 C1 0.0257(18) 0.0205(15) 0.0238(18) 0.0006(13) -0.0013(14) 0.0021(13) C2 0.036(2) 0.0317(19) 0.042(3) 0.0118(16) 0.0063(18) -0.0012(17) C3 0.051(3) 0.033(2) 0.076(4) 0.015(2) -0.005(3) -0.019(2) C4 0.060(3) 0.0230(18) 0.068(4) -0.007(2) -0.021(3) 0.003(2) C5 0.052(3) 0.031(2) 0.036(3) -0.0111(17) -0.0069(19) 0.009(2) C6 0.033(2) 0.0269(19) 0.027(2) -0.0006(14) -0.0018(15) 0.0046(15) C7 0.028(2) 0.0324(19) 0.0224(19) 0.0031(15) -0.0045(15) -0.0001(16) C8 0.026(2) 0.038(2) 0.0233(18) 0.0048(16) 0.0032(16) 0.0024(17) C9 0.0254(19) 0.0299(18) 0.0253(19) -0.0024(15) 0.0006(16) 0.0034(16) P1 0.0180(4) 0.0229(4) 0.0175(4) 0.0006(3) 0.0002(3) 0.0006(3) Se1 0.03182(19) 0.02361(15) 0.02242(17) -0.00123(15) -0.00816(15) 0.00506(14) I1 0.02394(11) 0.02324(10) 0.02357(11) -0.00012(11) 0.00043(10) -0.00165(8) C10 0.097(10) 0.045(5) 0.083(9) -0.016(8) 0.043(8) 0.020(8) Cl1A 0.066(3) 0.0430(16) 0.049(2) -0.0130(17) -0.0142(17) 0.0298(18) Cl1B 0.084(4) 0.055(3) 0.088(5) -0.021(3) 0.032(3) -0.009(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 C6 1.382(5) . ? C1 C2 1.391(5) . ? C1 Se1 1.939(3) . ? C2 C3 1.392(6) . ? C2 H2 0.97(5) . ? C3 C4 1.377(8) . ? C3 H3 0.93(5) . ? C4 C5 1.363(8) . ? C4 H4 0.92(5) . ? C5 C6 1.396(5) . ? C5 H5 0.95(5) . ? C6 H6 0.97(6) . ? C7 P1 1.781(4) . ? C7 H7A 0.96(6) . ? C7 H7B 0.94(4) . ? C7 H7C 1.02(4) . ? C8 P1 1.781(4) . ? C8 H8A 0.92(4) . ? C8 H8B 0.95(5) . ? C8 H8C 1.01(6) . ? C9 P1 1.789(4) . ? C9 H9A 1.00(5) . ? C9 H9B 1.05(5) . ? C9 H9C 0.93(5) . ? P1 Se1 2.2220(9) . ? C10 Cl1A 1.683(13) . ? C10 Cl1B 1.751(15) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? Cl1A Cl1B 0.567(7) 2_665 ? Cl1A C10 1.874(16) 2_665 ? Cl1B Cl1A 0.567(7) 2_665 ? Cl1B C10 1.349(14) 2_665 ? 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 C6 C1 C2 121.9(3) . . ? C6 C1 Se1 118.9(3) . . ? C2 C1 Se1 119.1(3) . . ? C1 C2 C3 118.2(4) . . ? C1 C2 H2 119(2) . . ? C3 C2 H2 123(3) . . ? C4 C3 C2 119.9(5) . . ? C4 C3 H3 126(3) . . ? C2 C3 H3 113(3) . . ? C5 C4 C3 121.5(4) . . ? C5 C4 H4 127(4) . . ? C3 C4 H4 111(4) . . ? C4 C5 C6 120.0(4) . . ? C4 C5 H5 121(3) . . ? C6 C5 H5 119(3) . . ? C1 C6 C5 118.5(4) . . ? C1 C6 H6 119(3) . . ? C5 C6 H6 122(3) . . ? P1 C7 H7A 104(3) . . ? P1 C7 H7B 107(3) . . ? H7A C7 H7B 113(4) . . ? P1 C7 H7C 111(2) . . ? H7A C7 H7C 116(4) . . ? H7B C7 H7C 105(4) . . ? P1 C8 H8A 109(3) . . ? P1 C8 H8B 104(3) . . ? H8A C8 H8B 113(4) . . ? P1 C8 H8C 105(3) . . ? H8A C8 H8C 115(4) . . ? H8B C8 H8C 111(4) . . ? P1 C9 H9A 107(2) . . ? P1 C9 H9B 106(2) . . ? H9A C9 H9B 116(4) . . ? P1 C9 H9C 106(3) . . ? H9A C9 H9C 103(4) . . ? H9B C9 H9C 118(3) . . ? C7 P1 C8 109.9(2) . . ? C7 P1 C9 108.16(19) . . ? C8 P1 C9 108.75(19) . . ? C7 P1 Se1 109.82(13) . . ? C8 P1 Se1 109.72(14) . . ? C9 P1 Se1 110.50(14) . . ? C1 Se1 P1 96.90(10) . . ? Cl1A C10 Cl1B 116.0(9) . . ? Cl1A C10 H10A 108.3 . . ? Cl1B C10 H10A 108.3 . . ? Cl1A C10 H10B 108.3 . . ? Cl1B C10 H10B 108.3 . . ? H10A C10 H10B 107.4 . . ? Cl1B Cl1A C10 45.6(13) 2_665 . ? Cl1B Cl1A C10 68.8(14) 2_665 2_665 ? C10 Cl1A C10 29.8(8) . 2_665 ? Cl1A Cl1B C10 116.9(16) 2_665 2_665 ? Cl1A Cl1B C10 93.7(16) 2_665 . ? C10 Cl1B C10 31.8(9) 2_665 . ? 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 C6 C1 C2 C3 0.3(6) . . . . ? Se1 C1 C2 C3 -178.1(3) . . . . ? C1 C2 C3 C4 0.1(7) . . . . ? C2 C3 C4 C5 -0.7(8) . . . . ? C3 C4 C5 C6 0.9(8) . . . . ? C2 C1 C6 C5 -0.1(6) . . . . ? Se1 C1 C6 C5 178.3(3) . . . . ? C4 C5 C6 C1 -0.5(6) . . . . ? C6 C1 Se1 P1 86.4(3) . . . . ? C2 C1 Se1 P1 -95.2(3) . . . . ? C7 P1 Se1 C1 19.73(18) . . . . ? C8 P1 Se1 C1 -101.13(19) . . . . ? C9 P1 Se1 C1 138.96(18) . . . . ? Cl1B C10 Cl1A Cl1B -175(2) . . . 2_665 ? Cl1B C10 Cl1A C10 -41.3(10) . . . 2_665 ? Cl1A C10 Cl1B Cl1A -79.5(17) . . . 2_665 ? Cl1A C10 Cl1B C10 59.8(17) . . . 2_665 ? data_rgp29b _database_code_depnum_ccdc_archive 'CCDC 611257' _audit_creation_date 2001-05-01T23:47:06-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H26 I1 P1 Se1' _chemical_formula_structural 'C27 H26 I1 P1 SE1' _chemical_formula_sum 'C27 H26 I P Se' _chemical_formula_weight 587.31 _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 9.523(2) _cell_length_b 11.1159(10) _cell_length_c 13.429(2) _cell_angle_alpha 96.78(2) _cell_angle_beta 103.11(2) _cell_angle_gamma 112.67(2) _cell_volume 1243.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.6 _cell_measurement_theta_max 15.2 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.827 _exptl_absorpt_factor_muR 0.564 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 4 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.5384 _exptl_absorpt_correction_T_max 0.6017 _exptl_absorpt_correction_T_ave 0.5204 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_ub_11 -0.112197 _diffrn_orient_matrix_ub_12 -0.52107E-1 _diffrn_orient_matrix_ub_13 -0.46293E-1 _diffrn_orient_matrix_ub_21 0.03576 _diffrn_orient_matrix_ub_22 -0.54992E-1 _diffrn_orient_matrix_ub_23 -0.43675E-1 _diffrn_orient_matrix_ub_31 -0.18445E-1 _diffrn_orient_matrix_ub_32 -0.65501E-1 _diffrn_orient_matrix_ub_33 0.46029E-1 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_standards_decay_corr_max 1.031 _diffrn_standards_decay_corr_min 0.991 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 -4 0 5 -1 -5 5 -1 -5 _diffrn_reflns_number 5165 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_unetI/netI 0.0316 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 2 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 4373 _reflns_number_gt 3517 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _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^)+(0.0377P)^2^+0.5162P] 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 4373 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.031 _refine_ls_wR_factor_ref 0.0721 _refine_ls_wR_factor_gt 0.0664 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 0.853 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.079 #----------------------------------------------------------------------------# # 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' I I -0.4742 1.8119 '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 I1 I 0.11855(2) 0.244781(18) 0.259395(15) 0.03886(5) Uani 1 1 d . . . P1 P 0.58134(7) 0.71554(6) 0.22471(5) 0.02231(15) Uani 1 1 d . . . Se1 Se 0.40892(3) 0.51859(2) 0.24405(2) 0.02664(6) Uani 1 1 d . . . C1 C 0.5679(3) 0.4669(2) 0.31797(19) 0.0259(6) Uani 1 1 d . . . C2 C 0.6414(3) 0.5172(2) 0.4245(2) 0.0305(7) Uani 1 1 d . . . C3 C 0.7549(3) 0.4781(3) 0.4748(2) 0.0380(8) Uani 1 1 d . . . C4 C 0.7945(3) 0.3906(3) 0.4180(2) 0.0415(8) Uani 1 1 d . . . C5 C 0.7214(3) 0.3409(3) 0.3119(2) 0.0366(7) Uani 1 1 d . . . C6 C 0.6078(3) 0.3795(2) 0.2608(2) 0.0314(7) Uani 1 1 d . . . C7 C 0.4541(3) 0.7562(2) 0.12670(18) 0.0236(6) Uani 1 1 d . . . C8 C 0.3591(3) 0.6619(2) 0.0334(2) 0.0285(6) Uani 1 1 d . . . C9 C 0.2617(3) 0.6929(3) -0.0418(2) 0.0307(7) Uani 1 1 d . . . C10 C 0.2580(3) 0.8156(3) -0.0246(2) 0.0316(7) Uani 1 1 d . . . C11 C 0.3490(3) 0.9108(2) 0.0677(2) 0.0286(6) Uani 1 1 d . . . C12 C 0.4491(3) 0.8806(2) 0.14392(19) 0.0255(6) Uani 1 1 d . . . C13 C 0.3407(4) 1.0437(3) 0.0863(3) 0.0489(9) Uani 1 1 d . . . C14 C 0.6701(3) 0.8450(2) 0.34320(19) 0.0242(6) Uani 1 1 d . . . C15 C 0.6033(3) 0.8332(2) 0.4255(2) 0.0280(6) Uani 1 1 d . . . C16 C 0.6706(3) 0.9337(2) 0.5164(2) 0.0327(7) Uani 1 1 d . . . C17 C 0.8050(3) 1.0455(3) 0.5221(2) 0.0409(8) Uani 1 1 d . . . C18 C 0.8711(3) 1.0604(3) 0.4401(2) 0.0411(8) Uani 1 1 d . . . C19 C 0.8048(3) 0.9596(2) 0.3504(2) 0.0314(7) Uani 1 1 d . . . C20 C 0.6010(4) 0.9202(3) 0.6066(2) 0.0497(9) Uani 1 1 d . . . C21 C 0.7396(3) 0.7040(2) 0.17832(19) 0.0229(6) Uani 1 1 d . . . C22 C 0.7488(3) 0.7186(2) 0.0783(2) 0.0308(7) Uani 1 1 d . . . C23 C 0.8726(3) 0.7078(3) 0.0464(2) 0.0386(8) Uani 1 1 d . . . C24 C 0.9838(3) 0.6806(3) 0.1132(2) 0.0370(7) Uani 1 1 d . . . C25 C 0.9777(3) 0.6655(2) 0.2134(2) 0.0302(7) Uani 1 1 d . . . C26 C 0.8560(3) 0.6797(2) 0.24570(19) 0.0249(6) Uani 1 1 d . . . C27 C 1.0972(3) 0.6330(3) 0.2834(3) 0.0448(8) Uani 1 1 d . . . H2 H 0.614(3) 0.575(2) 0.4642(18) 0.019(6) Uiso 1 1 d . . . H3 H 0.805(3) 0.520(3) 0.546(2) 0.039(8) Uiso 1 1 d . . . H4 H 0.872(3) 0.367(3) 0.452(2) 0.046(9) Uiso 1 1 d . . . H5 H 0.748(3) 0.274(3) 0.274(2) 0.036(8) Uiso 1 1 d . . . H6 H 0.556(3) 0.346(2) 0.181(2) 0.037(8) Uiso 1 1 d . . . H8 H 0.362(3) 0.585(3) 0.020(2) 0.038(8) Uiso 1 1 d . . . H9 H 0.200(3) 0.631(3) -0.098(2) 0.040(8) Uiso 1 1 d . . . H10 H 0.205(3) 0.837(2) -0.0698(18) 0.020(6) Uiso 1 1 d . . . H12 H 0.513(3) 0.940(2) 0.2091(18) 0.020(6) Uiso 1 1 d . . . H13A H 0.419(6) 1.113(5) 0.072(4) 0.14(2) Uiso 1 1 d . . . H13B H 0.328(5) 1.066(4) 0.142(3) 0.097(15) Uiso 1 1 d . . . H13C H 0.246(6) 1.036(5) 0.044(4) 0.135(19) Uiso 1 1 d . . . H15 H 0.511(2) 0.755(2) 0.4176(16) 0.009(5) Uiso 1 1 d . . . H17 H 0.850(3) 1.107(3) 0.582(2) 0.048(9) Uiso 1 1 d . . . H18 H 0.959(4) 1.130(3) 0.445(2) 0.057(10) Uiso 1 1 d . . . H19 H 0.851(2) 0.960(2) 0.2981(17) 0.014(6) Uiso 1 1 d . . . H20A H 0.488(5) 0.885(5) 0.585(4) 0.127(18) Uiso 1 1 d . . . H20B H 0.593(4) 0.850(4) 0.632(3) 0.088(13) Uiso 1 1 d . . . H20C H 0.650(5) 1.001(4) 0.649(3) 0.115(16) Uiso 1 1 d . . . H22 H 0.670(3) 0.737(2) 0.0343(19) 0.024(7) Uiso 1 1 d . . . H23 H 0.877(3) 0.718(2) -0.026(2) 0.029(7) Uiso 1 1 d . . . H24 H 1.058(3) 0.673(3) 0.088(2) 0.038(8) Uiso 1 1 d . . . H26 H 0.850(2) 0.670(2) 0.3110(17) 0.011(6) Uiso 1 1 d . . . H27A H 1.195(4) 0.693(3) 0.288(3) 0.064(10) Uiso 1 1 d . . . H27B H 1.085(4) 0.550(3) 0.253(3) 0.065(11) Uiso 1 1 d . . . H27C H 1.089(4) 0.634(4) 0.348(3) 0.078(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 I1 0.03286(9) 0.03887(9) 0.03963(9) 0.01647(7) 0.00793(7) 0.00938(7) P1 0.0219(2) 0.0234(3) 0.0249(3) 0.0082(2) 0.0062(2) 0.0127(2) Se1 0.02305(10) 0.02751(11) 0.03218(13) 0.01148(10) 0.00745(10) 0.01278(9) C1 0.0242(10) 0.0259(10) 0.0313(12) 0.0129(9) 0.0090(9) 0.0122(9) C2 0.0361(11) 0.0329(12) 0.0289(13) 0.0088(10) 0.0154(10) 0.0175(10) C3 0.0402(13) 0.0461(14) 0.0282(14) 0.0117(11) 0.0024(12) 0.0222(11) C4 0.0376(13) 0.0473(14) 0.0465(16) 0.0196(12) 0.0071(12) 0.0256(11) C5 0.0447(12) 0.0378(12) 0.0400(15) 0.0125(11) 0.0161(12) 0.0277(10) C6 0.0360(12) 0.0285(11) 0.0309(13) 0.0080(10) 0.0089(11) 0.0150(10) C7 0.0227(10) 0.0264(10) 0.0267(12) 0.0121(9) 0.0091(9) 0.0128(8) C8 0.0290(11) 0.0283(11) 0.0302(13) 0.0063(10) 0.0081(10) 0.0145(9) C9 0.0272(11) 0.0363(13) 0.0228(12) 0.0066(10) 0.0042(10) 0.0094(10) C10 0.0292(11) 0.0439(12) 0.0311(13) 0.0219(10) 0.0098(10) 0.0211(10) C11 0.0315(11) 0.0302(11) 0.0338(13) 0.0179(10) 0.0139(10) 0.0178(9) C12 0.0252(10) 0.0273(11) 0.0254(12) 0.0080(10) 0.0082(9) 0.0118(9) C13 0.0632(16) 0.0415(13) 0.0534(18) 0.0180(13) 0.0143(15) 0.0338(12) C14 0.0210(10) 0.0299(11) 0.0261(12) 0.0094(9) 0.0060(9) 0.0151(8) C15 0.0259(10) 0.0295(11) 0.0341(13) 0.0131(10) 0.0084(10) 0.0162(9) C16 0.0406(11) 0.0410(12) 0.0283(13) 0.0094(10) 0.0091(10) 0.0298(10) C17 0.0429(13) 0.0434(14) 0.0293(15) -0.0073(12) -0.0017(12) 0.0225(11) C18 0.0362(14) 0.0312(13) 0.0472(17) 0.0038(13) 0.0089(13) 0.0087(11) C19 0.0309(12) 0.0311(12) 0.0303(13) 0.0074(11) 0.0084(11) 0.0116(10) C20 0.0678(17) 0.0598(17) 0.0357(15) 0.0134(13) 0.0227(13) 0.0368(14) C21 0.0232(10) 0.0187(10) 0.0271(12) 0.0052(9) 0.0082(9) 0.0090(8) C22 0.0320(11) 0.0333(12) 0.0315(13) 0.0129(10) 0.0108(10) 0.0161(10) C23 0.0454(13) 0.0417(14) 0.0324(14) 0.0116(11) 0.0195(11) 0.0170(11) C24 0.0326(11) 0.0405(13) 0.0474(15) 0.0118(12) 0.0249(11) 0.0174(10) C25 0.0247(11) 0.0252(11) 0.0421(15) 0.0074(11) 0.0107(10) 0.0116(9) C26 0.0238(10) 0.0260(11) 0.0262(12) 0.0094(9) 0.0083(9) 0.0104(9) C27 0.0303(12) 0.0533(15) 0.0573(19) 0.0155(14) 0.0114(13) 0.0245(11) #----------------------------------------------------------------------------# # 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 P1 C14 1.797(2) . ? P1 C21 1.797(3) . ? P1 C7 1.801(2) . ? P1 Se1 2.2612(8) . ? Se1 C1 1.931(3) . ? C1 C2 1.380(3) . ? C1 C6 1.385(4) . ? C2 C3 1.383(4) . ? C3 C4 1.383(5) . ? C4 C5 1.374(4) . ? C5 C6 1.384(4) . ? C7 C8 1.390(3) . ? C7 C12 1.396(4) . ? C8 C9 1.379(4) . ? C9 C10 1.371(4) . ? C10 C11 1.379(3) . ? C11 C12 1.398(4) . ? C11 C13 1.505(4) . ? C14 C15 1.390(4) . ? C14 C19 1.390(3) . ? C15 C16 1.386(3) . ? C16 C17 1.377(4) . ? C16 C20 1.502(4) . ? C17 C18 1.382(5) . ? C18 C19 1.377(4) . ? C21 C22 1.391(4) . ? C21 C26 1.398(3) . ? C22 C23 1.384(4) . ? C23 C24 1.378(4) . ? C24 C25 1.386(4) . ? C25 C26 1.382(4) . ? C25 C27 1.490(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 C14 P1 C21 107.86(11) . . ? C14 P1 C7 110.16(12) . . ? C21 P1 C7 109.76(12) . . ? C14 P1 Se1 113.05(9) . . ? C21 P1 Se1 113.83(8) . . ? C7 P1 Se1 102.06(8) . . ? C1 Se1 P1 96.57(7) . . ? C2 C1 C6 120.9(2) . . ? C2 C1 Se1 120.9(2) . . ? C6 C1 Se1 118.18(18) . . ? C1 C2 C3 119.4(3) . . ? C4 C3 C2 119.8(2) . . ? C5 C4 C3 120.7(3) . . ? C4 C5 C6 119.9(3) . . ? C5 C6 C1 119.4(2) . . ? C8 C7 C12 119.9(2) . . ? C8 C7 P1 119.42(19) . . ? C12 C7 P1 120.72(17) . . ? C9 C8 C7 119.4(2) . . ? C10 C9 C8 120.4(2) . . ? C9 C10 C11 121.6(2) . . ? C10 C11 C12 118.4(2) . . ? C10 C11 C13 121.0(2) . . ? C12 C11 C13 120.7(2) . . ? C7 C12 C11 120.3(2) . . ? C15 C14 C19 120.2(2) . . ? C15 C14 P1 120.90(16) . . ? C19 C14 P1 118.9(2) . . ? C16 C15 C14 120.9(2) . . ? C17 C16 C15 117.7(3) . . ? C17 C16 C20 121.1(2) . . ? C15 C16 C20 121.2(2) . . ? C16 C17 C18 122.2(2) . . ? C19 C18 C17 119.8(2) . . ? C18 C19 C14 119.2(3) . . ? C22 C21 C26 119.7(2) . . ? C22 C21 P1 121.9(2) . . ? C26 C21 P1 118.38(19) . . ? C23 C22 C21 119.4(3) . . ? C24 C23 C22 119.8(3) . . ? C23 C24 C25 122.0(3) . . ? C26 C25 C24 117.9(3) . . ? C26 C25 C27 121.1(3) . . ? C24 C25 C27 121.0(3) . . ? C25 C26 C21 121.1(2) . . ? # Attachment '(oanisyl)3PSePhI.cif' # CIF produced by WinGX routine CIF_UPDATE # Created on 2002-08-13 at 23:38:10 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.2 # Request file : c:\wingx\files\archive.dat # CIF files read : smg33c absorb dreduc sortav struct data_smg33c _database_code_depnum_ccdc_archive 'CCDC 611258' _audit_creation_date 2002-08-13T23:38:10-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C28 H28 Cl2 I1 O3 P1 Se1' _chemical_formula_sum 'C28 H28 Cl2 I O3 P Se' _chemical_formula_weight 720.23 _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 9.424(4) _cell_length_b 11.877(5) _cell_length_c 13.986(7) _cell_angle_alpha 87.32(2) _cell_angle_beta 80.04(2) _cell_angle_gamma 68.418(16) _cell_volume 1433.6(11) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 247119 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.657 _exptl_absorpt_correction_type sphere _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.877 _exptl_absorpt_correction_T_max 1.137 #----------------------------------------------------------------------------# # 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_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.889256E-1 _diffrn_orient_matrix_ub_12 0.3198E-3 _diffrn_orient_matrix_ub_13 -0.50592E-1 _diffrn_orient_matrix_ub_21 0.734508E-1 _diffrn_orient_matrix_ub_22 -0.613944E-1 _diffrn_orient_matrix_ub_23 0.372383E-1 _diffrn_orient_matrix_ub_31 -0.97375E-2 _diffrn_orient_matrix_ub_32 -0.06657 _diffrn_orient_matrix_ub_33 -0.364039E-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 0.0618 _diffrn_reflns_av_unetI/netI 0.0856 _diffrn_reflns_number 5071 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.634 _diffrn_measured_fraction_theta_max 0.634 _reflns_number_total 3201 _reflns_number_gt 2328 _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. ; _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^+24.2513P] 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 0.0020(11) _refine_ls_number_reflns 3201 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1203 _refine_ls_R_factor_gt 0.0815 _refine_ls_wR_factor_ref 0.2001 _refine_ls_wR_factor_gt 0.1673 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.75 _refine_diff_density_min -0.931 _refine_diff_density_rms 0.128 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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' Cl Cl 0.1484 0.1585 '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 0.2364(18) 0.7712(14) 0.3567(11) 0.046(4) Uani 1 1 d . . . C2 C 0.1383(19) 0.7963(14) 0.4453(12) 0.048(4) Uani 1 1 d . . . C3 C 0.0032(18) 0.7724(14) 0.4559(12) 0.047(4) Uani 1 1 d . . . H3 H -0.0658 0.7902 0.5143 0.057 Uiso 1 1 calc R . . C4 C -0.0279(19) 0.7222(15) 0.3793(14) 0.060(5) Uani 1 1 d . . . H4 H -0.1181 0.7054 0.3871 0.072 Uiso 1 1 calc R . . C5 C 0.0727(19) 0.6951(14) 0.2892(13) 0.053(4) Uani 1 1 d . . . H5 H 0.0521 0.6601 0.2377 0.064 Uiso 1 1 calc R . . C6 C 0.2015(18) 0.7233(14) 0.2820(12) 0.050(4) Uani 1 1 d . . . H6 H 0.2689 0.709 0.223 0.059 Uiso 1 1 calc R . . C7 C 0.0871(19) 0.8720(16) 0.6105(11) 0.059(5) Uani 1 1 d . . . H7A H -0.01 0.9348 0.6041 0.088 Uiso 1 1 calc R . . H7B H 0.1371 0.8992 0.6537 0.088 Uiso 1 1 calc R . . H7C H 0.0692 0.8011 0.6362 0.088 Uiso 1 1 calc R . . C8 C 0.5037(18) 0.7855(14) 0.2263(10) 0.045(4) Uani 1 1 d . . . C9 C 0.4219(18) 0.8592(14) 0.1539(12) 0.049(4) Uani 1 1 d . . . C10 C 0.5009(18) 0.8455(15) 0.0584(11) 0.052(5) Uani 1 1 d . . . H10 H 0.4542 0.8979 0.0119 0.063 Uiso 1 1 calc R . . C11 C 0.6397(19) 0.7609(15) 0.0312(12) 0.056(5) Uani 1 1 d . . . H11 H 0.6842 0.7496 -0.034 0.068 Uiso 1 1 calc R . . C12 C 0.718(2) 0.6888(16) 0.1016(14) 0.066(5) Uani 1 1 d . . . H12 H 0.8182 0.6327 0.0837 0.079 Uiso 1 1 calc R . . C13 C 0.6478(19) 0.7010(15) 0.1972(11) 0.052(4) Uani 1 1 d . . . H13 H 0.6994 0.6506 0.243 0.062 Uiso 1 1 calc R . . C14 C 0.199(2) 1.0192(15) 0.1237(13) 0.065(5) Uani 1 1 d . . . H14A H 0.2631 1.0577 0.0861 0.098 Uiso 1 1 calc R . . H14B H 0.1092 1.0797 0.1594 0.098 Uiso 1 1 calc R . . H14C H 0.1674 0.9752 0.0812 0.098 Uiso 1 1 calc R . . C15 C 0.5376(15) 0.6957(14) 0.4202(11) 0.043(4) Uani 1 1 d . . . C16 C 0.5917(17) 0.5723(14) 0.4003(11) 0.045(4) Uani 1 1 d . . . C17 C 0.6917(19) 0.4896(15) 0.4525(11) 0.057(5) Uani 1 1 d . . . H17 H 0.7255 0.407 0.4392 0.069 Uiso 1 1 calc R . . C18 C 0.7400(18) 0.5323(17) 0.5244(11) 0.053(5) Uani 1 1 d . . . H18 H 0.8123 0.4775 0.558 0.064 Uiso 1 1 calc R . . C19 C 0.6865(18) 0.6525(16) 0.5494(12) 0.056(5) Uani 1 1 d . . . H19 H 0.7177 0.6791 0.6008 0.067 Uiso 1 1 calc R . . C20 C 0.5870(16) 0.7313(14) 0.4970(11) 0.045(4) Uani 1 1 d . . . H20 H 0.55 0.8133 0.5134 0.054 Uiso 1 1 calc R . . C21 C 0.590(2) 0.4209(15) 0.2889(13) 0.065(5) Uani 1 1 d . . . H21A H 0.699 0.3995 0.2652 0.097 Uiso 1 1 calc R . . H21B H 0.539 0.4163 0.2364 0.097 Uiso 1 1 calc R . . H21C H 0.5755 0.3659 0.3386 0.097 Uiso 1 1 calc R . . C22 C 0.5012(17) 1.0295(13) 0.3094(12) 0.047(4) Uani 1 1 d . . . C23 C 0.438(2) 1.1286(15) 0.2534(12) 0.056(5) Uani 1 1 d . . . H23 H 0.3318 1.1701 0.2604 0.067 Uiso 1 1 calc R . . C24 C 0.544(3) 1.1642(18) 0.1845(13) 0.072(6) Uani 1 1 d . . . H24 H 0.5071 1.2321 0.1468 0.086 Uiso 1 1 calc R . . C25 C 0.694(3) 1.0999(18) 0.1745(13) 0.072(6) Uani 1 1 d . . . H25 H 0.7615 1.1242 0.1295 0.086 Uiso 1 1 calc R . . C26 C 0.753(2) 0.9999(16) 0.2275(14) 0.064(5) Uani 1 1 d . . . H26 H 0.859 0.9551 0.2173 0.077 Uiso 1 1 calc R . . C27 C 0.6528(19) 0.9657(15) 0.2973(12) 0.056(5) Uani 1 1 d . . . H27 H 0.6913 0.8985 0.3353 0.068 Uiso 1 1 calc R . . C28 C -0.1397(19) 0.3581(17) -0.0082(15) 0.074(6) Uani 1 1 d . . . H28A H -0.1213 0.3794 0.0534 0.088 Uiso 1 1 calc R . . H28B H -0.1069 0.4073 -0.0579 0.088 Uiso 1 1 calc R . . O1 O 0.1846(12) 0.8432(9) 0.5165(8) 0.050(3) Uani 1 1 d . . . O2 O 0.2835(12) 0.9384(9) 0.1894(7) 0.053(3) Uani 1 1 d . . . O3 O 0.5264(12) 0.5431(9) 0.3285(8) 0.054(3) Uani 1 1 d . . . P1 P 0.4121(5) 0.7984(4) 0.3477(3) 0.0459(11) Uani 1 1 d . . . Se1 Se 0.35906(19) 0.98615(15) 0.40276(13) 0.0528(6) Uani 1 1 d . . . I1 I 0.04692(14) 0.38899(11) 0.21510(9) 0.0643(5) Uani 1 1 d . . . Cl1 Cl -0.3325(6) 0.3888(5) -0.0019(4) 0.0937(19) Uani 1 1 d . . . Cl2 Cl -0.0287(6) 0.2034(4) -0.0355(4) 0.0761(15) 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 0.055(10) 0.046(9) 0.029(8) -0.007(8) -0.009(8) -0.008(8) C2 0.048(10) 0.046(9) 0.042(10) -0.006(9) -0.010(9) -0.007(8) C3 0.043(10) 0.051(9) 0.034(9) -0.002(8) -0.010(8) 0.001(8) C4 0.046(10) 0.054(10) 0.067(12) 0.013(10) -0.017(9) 0.000(8) C5 0.058(11) 0.050(10) 0.051(10) -0.004(9) -0.013(9) -0.018(9) C6 0.046(10) 0.055(10) 0.040(10) 0.003(9) 0.002(8) -0.014(8) C7 0.058(11) 0.075(12) 0.033(9) -0.010(9) 0.006(8) -0.018(9) C8 0.056(10) 0.051(9) 0.029(8) 0.002(8) -0.003(7) -0.023(8) C9 0.050(10) 0.056(10) 0.052(10) 0.022(9) -0.027(9) -0.025(9) C10 0.055(10) 0.065(11) 0.036(9) 0.018(9) 0.004(8) -0.027(9) C11 0.049(10) 0.069(11) 0.042(10) -0.010(9) 0.004(8) -0.016(9) C12 0.058(11) 0.063(11) 0.078(14) 0.009(11) 0.006(10) -0.032(10) C13 0.056(10) 0.058(10) 0.039(9) 0.010(9) -0.004(8) -0.022(9) C14 0.067(12) 0.052(10) 0.065(12) 0.013(10) -0.022(10) -0.005(9) C15 0.023(7) 0.063(10) 0.038(9) 0.013(9) -0.002(7) -0.015(7) C16 0.037(9) 0.051(10) 0.037(9) -0.001(9) 0.003(8) -0.008(8) C17 0.070(12) 0.051(10) 0.032(9) 0.011(9) -0.002(9) -0.006(9) C18 0.047(10) 0.074(12) 0.026(8) 0.000(9) -0.002(8) -0.010(9) C19 0.044(10) 0.068(12) 0.041(10) -0.001(10) -0.002(8) -0.006(9) C20 0.034(8) 0.047(9) 0.045(9) -0.002(8) 0.000(8) -0.007(7) C21 0.074(12) 0.056(11) 0.050(11) -0.012(9) -0.002(10) -0.010(10) C22 0.041(9) 0.044(9) 0.053(10) -0.004(8) 0.006(8) -0.017(8) C23 0.075(12) 0.055(10) 0.042(10) -0.013(9) -0.020(10) -0.021(9) C24 0.102(17) 0.067(12) 0.048(12) -0.002(10) -0.025(12) -0.027(12) C25 0.098(16) 0.073(13) 0.049(11) 0.016(11) -0.020(11) -0.036(12) C26 0.052(11) 0.072(12) 0.072(13) -0.002(11) -0.005(10) -0.029(10) C27 0.053(11) 0.061(10) 0.046(10) 0.002(9) -0.009(9) -0.010(9) C28 0.058(12) 0.082(13) 0.081(14) 0.010(12) -0.018(10) -0.024(10) O1 0.060(7) 0.042(6) 0.037(6) -0.001(5) 0.006(5) -0.010(5) O2 0.053(7) 0.051(6) 0.040(6) 0.007(6) -0.009(5) -0.003(5) O3 0.052(7) 0.047(6) 0.048(7) -0.001(6) -0.005(6) -0.001(5) P1 0.042(2) 0.048(2) 0.039(2) 0.004(2) -0.0058(19) -0.0068(19) Se1 0.0483(11) 0.0505(10) 0.0519(11) 0.0005(9) -0.0048(8) -0.0106(8) I1 0.0612(8) 0.0635(8) 0.0580(8) 0.0025(6) -0.0097(6) -0.0113(6) Cl1 0.072(3) 0.110(4) 0.086(4) 0.004(4) -0.013(3) -0.019(3) Cl2 0.075(3) 0.076(3) 0.070(3) 0.011(3) -0.014(3) -0.019(3) #----------------------------------------------------------------------------# # 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 C6 1.36(2) . ? C1 C2 1.38(2) . ? C1 P1 1.783(18) . ? C2 O1 1.368(19) . ? C2 C3 1.39(2) . ? C3 C4 1.37(2) . ? C4 C5 1.41(2) . ? C5 C6 1.36(2) . ? C7 O1 1.443(17) . ? C8 C13 1.36(2) . ? C8 C9 1.442(19) . ? C8 P1 1.753(14) . ? C9 O2 1.322(18) . ? C9 C10 1.40(2) . ? C10 C11 1.33(2) . ? C11 C12 1.40(2) . ? C12 C13 1.38(2) . ? C14 O2 1.417(16) . ? C15 C20 1.38(2) . ? C15 C16 1.39(2) . ? C15 P1 1.775(14) . ? C16 C17 1.37(2) . ? C16 O3 1.382(19) . ? C17 C18 1.36(2) . ? C18 C19 1.37(2) . ? C19 C20 1.35(2) . ? C21 O3 1.447(19) . ? C22 C27 1.33(2) . ? C22 C23 1.38(2) . ? C22 Se1 1.899(14) . ? C23 C24 1.43(2) . ? C24 C25 1.32(3) . ? C25 C26 1.36(2) . ? C26 C27 1.39(2) . ? C28 Cl1 1.704(18) . ? C28 Cl2 1.769(19) . ? P1 Se1 2.241(5) . ? 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 C6 C1 C2 120.6(17) . . ? C6 C1 P1 122.2(12) . . ? C2 C1 P1 117.2(14) . . ? O1 C2 C1 116.1(16) . . ? O1 C2 C3 125.1(15) . . ? C1 C2 C3 118.7(18) . . ? C4 C3 C2 119.3(16) . . ? C3 C4 C5 122.1(18) . . ? C6 C5 C4 116.1(18) . . ? C1 C6 C5 123.1(16) . . ? C13 C8 C9 118.6(14) . . ? C13 C8 P1 121.4(11) . . ? C9 C8 P1 119.8(12) . . ? O2 C9 C10 128.5(13) . . ? O2 C9 C8 114.1(14) . . ? C10 C9 C8 117.3(14) . . ? C11 C10 C9 122.9(15) . . ? C10 C11 C12 119.4(16) . . ? C13 C12 C11 119.9(16) . . ? C8 C13 C12 121.5(15) . . ? C20 C15 C16 116.6(14) . . ? C20 C15 P1 123.6(12) . . ? C16 C15 P1 119.8(14) . . ? C17 C16 O3 124.7(15) . . ? C17 C16 C15 122.0(17) . . ? O3 C16 C15 113.2(13) . . ? C18 C17 C16 117.8(16) . . ? C17 C18 C19 122.7(16) . . ? C20 C19 C18 117.8(18) . . ? C19 C20 C15 122.9(16) . . ? C27 C22 C23 122.2(15) . . ? C27 C22 Se1 121.5(12) . . ? C23 C22 Se1 116.3(12) . . ? C22 C23 C24 117.0(16) . . ? C25 C24 C23 119.5(17) . . ? C24 C25 C26 122.6(19) . . ? C25 C26 C27 118.8(17) . . ? C22 C27 C26 119.7(15) . . ? Cl1 C28 Cl2 111.7(11) . . ? C2 O1 C7 118.9(13) . . ? C9 O2 C14 117.7(12) . . ? C16 O3 C21 119.1(12) . . ? C8 P1 C15 110.2(7) . . ? C8 P1 C1 110.1(8) . . ? C15 P1 C1 110.8(7) . . ? C8 P1 Se1 108.8(5) . . ? C15 P1 Se1 107.7(6) . . ? C1 P1 Se1 109.4(5) . . ? C22 Se1 P1 98.8(5) . . ? # Attachment '(otolyl)3PI2.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-04-25 at 17:13:53 # 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 struct data_s _database_code_depnum_ccdc_archive 'CCDC 611259' _audit_creation_date 2006-04-25T17:13:53-00:00 _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 'C21 H21 I2 P' _chemical_formula_sum 'C21 H21 I2 P' _chemical_formula_weight 558.15 _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 9.1482(2) _cell_length_b 11.1968(2) _cell_length_c 11.4776(2) _cell_angle_alpha 61.4140(10) _cell_angle_beta 89.3290(10) _cell_angle_gamma 88.8470(10) _cell_volume 1032.13(3) _cell_formula_units_Z 2 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used 4608 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plates _exptl_crystal_colour orange _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.796 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.125 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5738 _exptl_absorpt_correction_T_max 0.8594 _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 133(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 -0.173442E-1 _diffrn_orient_matrix_ub_12 -0.909347E-1 _diffrn_orient_matrix_ub_13 0.786137E-1 _diffrn_orient_matrix_ub_21 0.833857E-1 _diffrn_orient_matrix_ub_22 0.144338E-1 _diffrn_orient_matrix_ub_23 0.472048E-1 _diffrn_orient_matrix_ub_31 -0.685554E-1 _diffrn_orient_matrix_ub_32 0.432461E-1 _diffrn_orient_matrix_ub_33 0.379013E-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 0.043 _diffrn_reflns_av_unetI/netI 0.0251 _diffrn_reflns_number 4275 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 26.5 _diffrn_reflns_theta_full 26.5 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 4275 _reflns_number_gt 3739 _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 '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^)+(0.0180P)^2^+6.1701P] 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 4275 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0828 _refine_ls_wR_factor_gt 0.0773 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.86 _refine_diff_density_min -0.953 _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' I I -0.4742 1.8119 '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' 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 1.1946(5) 0.2013(5) 0.4875(4) 0.0221(9) Uani 1 1 d . . . C2 C 1.2166(5) 0.2414(5) 0.5855(5) 0.0265(10) Uani 1 1 d . . . C3 C 1.3081(5) 0.1592(5) 0.6917(5) 0.0316(11) Uani 1 1 d . . . H3 H 1.3247 0.184 0.7588 0.038 Uiso 1 1 calc R . . C4 C 1.3746(5) 0.0437(5) 0.7019(5) 0.0327(11) Uani 1 1 d . . . H4 H 1.4383 -0.0084 0.7742 0.039 Uiso 1 1 calc R . . C5 C 1.3500(5) 0.0021(5) 0.6076(5) 0.0300(10) Uani 1 1 d . . . H5 H 1.3948 -0.0788 0.6157 0.036 Uiso 1 1 calc R . . C6 C 1.2575(5) 0.0818(5) 0.5002(5) 0.0281(10) Uani 1 1 d . . . H6 H 1.238 0.0537 0.4359 0.034 Uiso 1 1 calc R . . C7 C 1.1473(6) 0.3657(6) 0.5824(6) 0.0352(12) Uani 1 1 d . . . C8 C 0.9021(5) 0.3137(5) 0.3775(4) 0.0228(9) Uani 1 1 d . . . C9 C 0.8580(5) 0.2313(5) 0.5099(5) 0.0287(10) Uani 1 1 d . . . H9 H 0.9268 0.1716 0.5735 0.034 Uiso 1 1 calc R . . C10 C 0.7146(6) 0.2369(6) 0.5483(5) 0.0351(12) Uani 1 1 d . . . H10 H 0.6855 0.1821 0.6379 0.042 Uiso 1 1 calc R . . C11 C 0.6145(6) 0.3227(6) 0.4551(6) 0.0382(12) Uani 1 1 d . . . H11 H 0.5162 0.3267 0.4808 0.046 Uiso 1 1 calc R . . C12 C 0.6569(5) 0.4029(5) 0.3241(5) 0.0314(11) Uani 1 1 d . . . H12 H 0.5865 0.4615 0.2615 0.038 Uiso 1 1 calc R . . C13 C 0.8007(5) 0.4001(5) 0.2815(5) 0.0271(10) Uani 1 1 d . . . C14 C 0.8364(7) 0.4860(7) 0.1379(6) 0.0381(12) Uani 1 1 d . . . C15 C 1.2382(5) 0.2168(5) 0.1715(4) 0.0233(9) Uani 1 1 d . . . C16 C 1.1051(5) 0.2268(5) 0.2316(4) 0.0231(9) Uani 1 1 d . . . C17 C 0.9783(5) 0.1689(5) 0.2150(5) 0.0268(10) Uani 1 1 d . . . H17 H 0.8899 0.1751 0.2561 0.032 Uiso 1 1 calc R . . C18 C 0.9796(5) 0.1027(6) 0.1397(5) 0.0342(11) Uani 1 1 d . . . H18 H 0.8924 0.0652 0.1278 0.041 Uiso 1 1 calc R . . C19 C 1.1086(6) 0.0916(6) 0.0817(5) 0.0354(12) Uani 1 1 d . . . H19 H 1.1104 0.0457 0.0303 0.043 Uiso 1 1 calc R . . C20 C 1.2352(5) 0.1472(5) 0.0983(5) 0.0296(10) Uani 1 1 d . . . H20 H 1.3231 0.1376 0.0585 0.035 Uiso 1 1 calc R . . C21 C 1.3794(5) 0.2767(5) 0.1819(5) 0.0269(10) Uani 1 1 d . . . I1 I 1.20917(3) 0.54092(3) 0.22486(3) 0.02452(9) Uani 1 1 d . . . I2 I 1.37819(3) 0.80827(3) 0.09115(3) 0.02912(10) Uani 1 1 d . . . P1 P 1.09267(12) 0.30683(12) 0.33656(11) 0.0216(2) Uani 1 1 d . . . H21B H 1.455(6) 0.245(5) 0.154(5) 0.024(13) Uiso 1 1 d . . . H21A H 1.401(6) 0.257(6) 0.269(6) 0.034(15) Uiso 1 1 d . . . H21C H 1.379(6) 0.376(6) 0.121(6) 0.031(14) Uiso 1 1 d . . . H7A H 1.219(9) 0.443(8) 0.546(8) 0.08(2) Uiso 1 1 d . . . H7B H 1.067(8) 0.404(7) 0.519(7) 0.06(2) Uiso 1 1 d . . . H7C H 1.121(9) 0.356(8) 0.666(9) 0.08(3) Uiso 1 1 d . . . H14A H 0.906(10) 0.462(9) 0.107(8) 0.08(3) Uiso 1 1 d . . . H14B H 0.875(10) 0.577(10) 0.116(9) 0.10(3) Uiso 1 1 d . . . H14C H 0.756(10) 0.524(9) 0.083(9) 0.09(3) 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 C1 0.020(2) 0.025(2) 0.021(2) -0.0112(18) -0.0010(17) -0.0008(17) C2 0.023(2) 0.031(2) 0.026(2) -0.014(2) 0.0027(18) -0.0044(19) C3 0.026(2) 0.042(3) 0.026(2) -0.016(2) 0.0017(19) -0.004(2) C4 0.028(2) 0.039(3) 0.026(2) -0.012(2) -0.001(2) 0.002(2) C5 0.027(2) 0.028(2) 0.027(2) -0.007(2) 0.0011(19) 0.0059(19) C6 0.035(3) 0.024(2) 0.029(2) -0.016(2) 0.019(2) -0.0125(19) C7 0.037(3) 0.041(3) 0.036(3) -0.025(3) -0.004(2) 0.002(2) C8 0.020(2) 0.026(2) 0.026(2) -0.0150(19) 0.0005(17) -0.0015(17) C9 0.027(2) 0.035(3) 0.026(2) -0.017(2) 0.0019(19) -0.001(2) C10 0.031(3) 0.049(3) 0.032(3) -0.024(2) 0.008(2) -0.010(2) C11 0.021(2) 0.056(4) 0.050(3) -0.035(3) 0.004(2) -0.003(2) C12 0.023(2) 0.036(3) 0.041(3) -0.023(2) -0.004(2) 0.002(2) C13 0.026(2) 0.029(2) 0.030(2) -0.017(2) -0.0042(19) 0.0026(19) C14 0.032(3) 0.043(3) 0.029(3) -0.008(2) -0.004(2) 0.004(2) C15 0.020(2) 0.028(2) 0.020(2) -0.0102(18) -0.0014(17) 0.0015(17) C16 0.022(2) 0.027(2) 0.022(2) -0.0136(19) -0.0005(17) 0.0032(18) C17 0.022(2) 0.033(3) 0.031(2) -0.019(2) 0.0034(18) -0.0008(19) C18 0.025(2) 0.045(3) 0.043(3) -0.029(3) -0.001(2) -0.003(2) C19 0.032(3) 0.047(3) 0.041(3) -0.033(3) -0.002(2) -0.001(2) C20 0.022(2) 0.042(3) 0.032(2) -0.024(2) 0.0019(19) 0.003(2) C21 0.018(2) 0.034(3) 0.029(2) -0.016(2) 0.0054(19) -0.0009(19) I1 0.02329(16) 0.02705(16) 0.02476(16) -0.01372(13) 0.00069(11) 0.00093(11) I2 0.02893(17) 0.03137(18) 0.02626(16) -0.01302(14) 0.00473(12) -0.00682(13) P1 0.0222(5) 0.0253(6) 0.0194(5) -0.0125(5) -0.0034(4) 0.0046(4) #----------------------------------------------------------------------------# # 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 C6 1.389(6) . ? C1 C2 1.414(6) . ? C1 P1 1.817(4) . ? C2 C3 1.397(7) . ? C2 C7 1.503(7) . ? C3 C4 1.371(7) . ? C3 H3 0.95 . ? C4 C5 1.390(7) . ? C4 H4 0.95 . ? C5 C6 1.404(7) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? C7 H7A 1.01(8) . ? C7 H7B 0.97(7) . ? C7 H7C 0.94(9) . ? C8 C13 1.407(6) . ? C8 C9 1.408(6) . ? C8 P1 1.810(4) . ? C9 C10 1.388(7) . ? C9 H9 0.95 . ? C10 C11 1.382(8) . ? C10 H10 0.95 . ? C11 C12 1.388(8) . ? C11 H11 0.95 . ? C12 C13 1.403(7) . ? C12 H12 0.95 . ? C13 C14 1.494(7) . ? C14 H14A 0.82(9) . ? C14 H14B 1.00(10) . ? C14 H14C 0.93(9) . ? C15 C20 1.393(6) . ? C15 C16 1.421(6) . ? C15 C21 1.500(6) . ? C16 C17 1.399(6) . ? C16 P1 1.815(4) . ? C17 C18 1.382(7) . ? C17 H17 0.95 . ? C18 C19 1.380(7) . ? C18 H18 0.95 . ? C19 C20 1.383(7) . ? C19 H19 0.95 . ? C20 H20 0.95 . ? C21 H21B 0.90(5) . ? C21 H21A 0.94(6) . ? C21 H21C 0.99(6) . ? I1 P1 2.5523(12) . ? I1 I2 3.0727(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 C6 C1 C2 120.7(4) . . ? C6 C1 P1 117.2(3) . . ? C2 C1 P1 122.0(4) . . ? C3 C2 C1 117.4(4) . . ? C3 C2 C7 118.5(4) . . ? C1 C2 C7 124.0(4) . . ? C4 C3 C2 121.9(5) . . ? C4 C3 H3 119 . . ? C2 C3 H3 119 . . ? C3 C4 C5 120.7(5) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 118.8(5) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C1 C6 C5 120.3(4) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C2 C7 H7A 110(5) . . ? C2 C7 H7B 113(4) . . ? H7A C7 H7B 102(6) . . ? C2 C7 H7C 115(5) . . ? H7A C7 H7C 104(6) . . ? H7B C7 H7C 112(6) . . ? C13 C8 C9 120.5(4) . . ? C13 C8 P1 121.6(3) . . ? C9 C8 P1 117.9(3) . . ? C10 C9 C8 120.4(5) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 119.6(5) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.3(5) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C11 C12 C13 121.8(5) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C12 C13 C8 117.4(4) . . ? C12 C13 C14 118.6(5) . . ? C8 C13 C14 124.0(4) . . ? C13 C14 H14A 118(6) . . ? C13 C14 H14B 114(5) . . ? H14A C14 H14B 96(7) . . ? C13 C14 H14C 115(5) . . ? H14A C14 H14C 116(8) . . ? H14B C14 H14C 93(7) . . ? C20 C15 C16 117.2(4) . . ? C20 C15 C21 118.8(4) . . ? C16 C15 C21 124.0(4) . . ? C17 C16 C15 119.9(4) . . ? C17 C16 P1 117.4(3) . . ? C15 C16 P1 122.6(3) . . ? C18 C17 C16 121.0(4) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C19 C18 C17 119.5(5) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C18 C19 C20 120.1(5) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C15 122.2(4) . . ? C19 C20 H20 118.9 . . ? C15 C20 H20 118.9 . . ? C15 C21 H21B 111(3) . . ? C15 C21 H21A 113(3) . . ? H21B C21 H21A 107(5) . . ? C15 C21 H21C 110(3) . . ? H21B C21 H21C 104(4) . . ? H21A C21 H21C 111(5) . . ? P1 I1 I2 174.32(3) . . ? C8 P1 C16 108.1(2) . . ? C8 P1 C1 109.4(2) . . ? C16 P1 C1 107.9(2) . . ? C8 P1 I1 112.60(15) . . ? C16 P1 I1 111.19(15) . . ? C1 P1 I1 107.50(15) . . ? 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 C6 C1 C2 C3 2.5(7) . . . . ? P1 C1 C2 C3 -174.1(3) . . . . ? C6 C1 C2 C7 -177.2(5) . . . . ? P1 C1 C2 C7 6.3(7) . . . . ? C1 C2 C3 C4 -0.1(7) . . . . ? C7 C2 C3 C4 179.6(5) . . . . ? C2 C3 C4 C5 -1.7(8) . . . . ? C3 C4 C5 C6 1.1(7) . . . . ? C2 C1 C6 C5 -3.1(7) . . . . ? P1 C1 C6 C5 173.6(3) . . . . ? C4 C5 C6 C1 1.3(7) . . . . ? C13 C8 C9 C10 -1.7(7) . . . . ? P1 C8 C9 C10 177.2(4) . . . . ? C8 C9 C10 C11 0.9(8) . . . . ? C9 C10 C11 C12 -0.1(8) . . . . ? C10 C11 C12 C13 0.2(8) . . . . ? C11 C12 C13 C8 -1.0(7) . . . . ? C11 C12 C13 C14 177.9(5) . . . . ? C9 C8 C13 C12 1.7(7) . . . . ? P1 C8 C13 C12 -177.1(3) . . . . ? C9 C8 C13 C14 -177.1(5) . . . . ? P1 C8 C13 C14 4.1(7) . . . . ? C20 C15 C16 C17 -0.5(7) . . . . ? C21 C15 C16 C17 179.2(5) . . . . ? C20 C15 C16 P1 176.9(4) . . . . ? C21 C15 C16 P1 -3.3(7) . . . . ? C15 C16 C17 C18 -0.6(7) . . . . ? P1 C16 C17 C18 -178.2(4) . . . . ? C16 C17 C18 C19 1.1(8) . . . . ? C17 C18 C19 C20 -0.4(9) . . . . ? C18 C19 C20 C15 -0.7(9) . . . . ? C16 C15 C20 C19 1.1(7) . . . . ? C21 C15 C20 C19 -178.6(5) . . . . ? C13 C8 P1 C16 -69.7(4) . . . . ? C9 C8 P1 C16 111.5(4) . . . . ? C13 C8 P1 C1 173.0(4) . . . . ? C9 C8 P1 C1 -5.8(4) . . . . ? C13 C8 P1 I1 53.6(4) . . . . ? C9 C8 P1 I1 -125.3(3) . . . . ? C17 C16 P1 C8 -8.5(4) . . . . ? C15 C16 P1 C8 174.1(4) . . . . ? C17 C16 P1 C1 109.8(4) . . . . ? C15 C16 P1 C1 -67.7(4) . . . . ? C17 C16 P1 I1 -132.6(3) . . . . ? C15 C16 P1 I1 50.0(4) . . . . ? C6 C1 P1 C8 115.4(4) . . . . ? C2 C1 P1 C8 -68.0(4) . . . . ? C6 C1 P1 C16 -2.0(4) . . . . ? C2 C1 P1 C16 174.6(4) . . . . ? C6 C1 P1 I1 -122.1(3) . . . . ? C2 C1 P1 I1 54.6(4) . . . . ? I2 I1 P1 C8 175.7(3) . . . . ? I2 I1 P1 C16 -62.7(3) . . . . ? I2 I1 P1 C1 55.2(3) . . . . ? # Attachment '(thioanisyl)3PSePhI3.cif' # CIF produced by WinGX routine CIF_UPDATE # Created on 2002-08-29 at 09:41:45 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.2 # Request file : c:\wingx\files\archive.dat # CIF files read : smg40c dreduc sortav struct data_smg40c _database_code_depnum_ccdc_archive 'CCDC 611260' _audit_creation_date 2002-08-29T09:41:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H26 I3 P1 S3 Se1' _chemical_formula_sum 'C27 H26 I3 P S3 Se' _chemical_formula_weight 937.29 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _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 9.20130(10) _cell_length_b 28.5610(4) _cell_length_c 11.8494(2) _cell_angle_alpha 90 _cell_angle_beta 102.7550(10) _cell_angle_gamma 90 _cell_volume 3037.16(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 32434 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description cube _exptl_crystal_colour red _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 2.05 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1776 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 4.561 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.921 _exptl_absorpt_correction_T_max 1.027 #----------------------------------------------------------------------------# # 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_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.45996E-2 _diffrn_orient_matrix_ub_12 -0.104087E-1 _diffrn_orient_matrix_ub_13 0.797132E-1 _diffrn_orient_matrix_ub_21 -0.111128 _diffrn_orient_matrix_ub_22 0.2464E-2 _diffrn_orient_matrix_ub_23 -0.208425E-1 _diffrn_orient_matrix_ub_31 -0.67771E-2 _diffrn_orient_matrix_ub_32 -0.333389E-1 _diffrn_orient_matrix_ub_33 -0.264276E-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 0.0922 _diffrn_reflns_av_unetI/netI 0.0959 _diffrn_reflns_number 32790 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 6889 _reflns_number_gt 4149 _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. ; _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^+15.4411P] 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 6889 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1426 _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.046 _refine_diff_density_min -1.234 _refine_diff_density_rms 0.225 #----------------------------------------------------------------------------# # 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C1 C 0.6619(7) 0.2450(2) 0.4533(6) 0.0221(17) Uani 1 1 d . . . C2 C 0.7589(8) 0.2401(3) 0.5594(7) 0.0282(19) Uani 1 1 d . . . H2 H 0.7459 0.2161 0.6093 0.034 Uiso 1 1 calc R . . C3 C 0.8745(9) 0.2709(3) 0.5903(7) 0.035(2) Uani 1 1 d . . . H3 H 0.9429 0.2671 0.6602 0.042 Uiso 1 1 calc R . . C4 C 0.8904(9) 0.3077(3) 0.5182(8) 0.041(2) Uani 1 1 d . . . H4 H 0.9705 0.3281 0.5394 0.049 Uiso 1 1 calc R . . C5 C 0.7886(8) 0.3144(3) 0.4150(7) 0.034(2) Uani 1 1 d . . . H5 H 0.7966 0.3402 0.369 0.041 Uiso 1 1 calc R . . C6 C 0.6749(8) 0.2825(2) 0.3805(7) 0.0258(18) Uani 1 1 d . . . H6 H 0.6078 0.2859 0.3098 0.031 Uiso 1 1 calc R . . C7 C 0.5980(7) 0.0973(2) 0.5172(6) 0.0170(16) Uani 1 1 d . . . C8 C 0.6498(7) 0.0505(2) 0.5307(6) 0.0213(17) Uani 1 1 d . . . C9 C 0.6210(8) 0.0245(2) 0.6230(6) 0.0252(18) Uani 1 1 d . . . H9 H 0.6552 -0.0062 0.633 0.03 Uiso 1 1 calc R . . C10 C 0.5437(8) 0.0428(3) 0.6999(7) 0.0284(19) Uani 1 1 d . . . H10 H 0.5241 0.0242 0.7594 0.034 Uiso 1 1 calc R . . C11 C 0.4949(8) 0.0888(3) 0.6888(6) 0.0258(18) Uani 1 1 d . . . H11 H 0.4447 0.1017 0.7416 0.031 Uiso 1 1 calc R . . C12 C 0.5222(7) 0.1155(3) 0.5978(6) 0.0246(18) Uani 1 1 d . . . H12 H 0.4892 0.1464 0.5901 0.029 Uiso 1 1 calc R . . C13 C 0.8203(8) -0.0278(2) 0.5000(7) 0.0271(18) Uani 1 1 d . . . H13A H 0.8757 -0.0228 0.5777 0.041 Uiso 1 1 calc R . . H13B H 0.8835 -0.0423 0.4554 0.041 Uiso 1 1 calc R . . H13C H 0.7369 -0.0479 0.501 0.041 Uiso 1 1 calc R . . C14 C 0.5738(7) 0.1050(2) 0.2642(6) 0.0189(16) Uani 1 1 d . . . C15 C 0.4223(7) 0.0952(2) 0.2158(6) 0.0153(15) Uani 1 1 d . . . C16 C 0.3832(8) 0.0738(2) 0.1082(6) 0.0235(18) Uani 1 1 d . . . H16 H 0.2838 0.0668 0.0766 0.028 Uiso 1 1 calc R . . C17 C 0.4916(8) 0.0628(2) 0.0472(7) 0.0281(19) Uani 1 1 d . . . H17 H 0.464 0.0496 -0.0262 0.034 Uiso 1 1 calc R . . C18 C 0.6393(8) 0.0714(2) 0.0949(7) 0.0276(19) Uani 1 1 d . . . H18 H 0.7115 0.0635 0.0544 0.033 Uiso 1 1 calc R . . C19 C 0.6811(8) 0.0918(2) 0.2029(6) 0.0208(17) Uani 1 1 d . . . H19 H 0.7815 0.0968 0.2353 0.025 Uiso 1 1 calc R . . C20 C 0.1206(8) 0.1148(3) 0.1829(7) 0.053(3) Uani 1 1 d . . . H20A H 0.1402 0.1327 0.1193 0.079 Uiso 1 1 calc R . . H20B H 0.0439 0.1298 0.2129 0.079 Uiso 1 1 calc R . . H20C H 0.0885 0.0839 0.1567 0.079 Uiso 1 1 calc R . . C21 C 0.8285(7) 0.1488(2) 0.4308(6) 0.0147(15) Uani 1 1 d . . . C22 C 0.8942(7) 0.1775(2) 0.3601(6) 0.0192(17) Uani 1 1 d . . . C23 C 1.0433(8) 0.1895(2) 0.3999(6) 0.0239(18) Uani 1 1 d . . . H23 H 1.0891 0.209 0.3553 0.029 Uiso 1 1 calc R . . C24 C 1.1247(8) 0.1729(3) 0.5043(7) 0.0275(19) Uani 1 1 d . . . H24 H 1.2249 0.1808 0.5275 0.033 Uiso 1 1 calc R . . C25 C 1.0615(8) 0.1453(2) 0.5745(7) 0.0243(18) Uani 1 1 d . . . H25 H 1.1172 0.1347 0.6452 0.029 Uiso 1 1 calc R . . C26 C 0.9130(8) 0.1333(2) 0.5383(6) 0.0238(18) Uani 1 1 d . . . H26 H 0.8682 0.1147 0.5855 0.029 Uiso 1 1 calc R . . C27 C 0.9064(8) 0.2411(3) 0.1843(7) 0.035(2) Uani 1 1 d . . . H27A H 0.9212 0.2653 0.242 0.053 Uiso 1 1 calc R . . H27B H 0.858 0.254 0.1108 0.053 Uiso 1 1 calc R . . H27C H 1.001 0.2282 0.1791 0.053 Uiso 1 1 calc R . . P1 P 0.63201(19) 0.13450(6) 0.40157(16) 0.0163(4) Uani 1 1 d . . . S1 S 0.7541(2) 0.02755(6) 0.43560(18) 0.0264(5) Uani 1 1 d . . . S2 S 0.28777(19) 0.11086(7) 0.29480(16) 0.0237(4) Uani 1 1 d . . . S3 S 0.7921(2) 0.19573(7) 0.22386(17) 0.0257(5) Uani 1 1 d . . . Se1 Se 0.49940(8) 0.20156(2) 0.39981(7) 0.02106(18) Uani 1 1 d . . . I1 I 0.74882(6) 0.190575(19) 0.88125(5) 0.03788(16) Uani 1 1 d . . . I2 I 0.91692(5) 0.105679(17) 0.85612(4) 0.02735(14) Uani 1 1 d . . . I3 I 1.08859(7) 0.02447(2) 0.81978(6) 0.0546(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.019(4) 0.024(4) 0.023(5) -0.008(4) 0.003(3) 0.001(3) C2 0.035(5) 0.024(4) 0.025(5) 0.001(4) 0.007(4) 0.012(4) C3 0.041(5) 0.035(5) 0.024(5) -0.021(4) -0.005(4) -0.003(4) C4 0.030(5) 0.029(5) 0.062(7) -0.025(5) 0.007(5) -0.003(4) C5 0.033(5) 0.028(4) 0.040(6) -0.002(4) 0.004(4) -0.007(4) C6 0.026(4) 0.028(4) 0.022(5) 0.003(4) 0.001(4) -0.005(4) C7 0.014(3) 0.023(4) 0.014(4) 0.001(3) 0.004(3) -0.007(3) C8 0.020(4) 0.022(4) 0.024(5) 0.002(3) 0.010(3) -0.006(3) C9 0.031(4) 0.018(4) 0.026(5) -0.009(4) 0.005(4) -0.003(3) C10 0.036(5) 0.022(4) 0.026(5) 0.006(4) 0.004(4) -0.004(4) C11 0.032(4) 0.034(5) 0.016(5) 0.000(4) 0.015(4) -0.003(4) C12 0.021(4) 0.026(4) 0.028(5) -0.002(4) 0.008(4) 0.001(3) C13 0.032(4) 0.019(4) 0.032(5) 0.000(4) 0.010(4) 0.001(3) C14 0.025(4) 0.017(4) 0.015(4) 0.004(3) 0.004(3) -0.001(3) C15 0.018(4) 0.013(4) 0.017(4) 0.004(3) 0.009(3) 0.003(3) C16 0.028(4) 0.019(4) 0.020(5) -0.005(3) -0.001(4) 0.001(3) C17 0.037(5) 0.024(4) 0.024(5) 0.001(4) 0.009(4) 0.011(4) C18 0.035(5) 0.022(4) 0.027(5) 0.003(4) 0.008(4) 0.013(4) C19 0.022(4) 0.018(4) 0.025(5) 0.003(3) 0.011(4) 0.001(3) C20 0.023(4) 0.087(8) 0.042(6) -0.016(5) -0.005(4) 0.006(5) C21 0.016(4) 0.013(3) 0.016(4) -0.006(3) 0.006(3) 0.000(3) C22 0.021(4) 0.014(4) 0.023(4) 0.002(3) 0.006(3) 0.002(3) C23 0.026(4) 0.027(4) 0.022(5) -0.001(4) 0.015(4) -0.007(4) C24 0.019(4) 0.032(5) 0.031(5) -0.001(4) 0.003(4) 0.000(3) C25 0.022(4) 0.021(4) 0.026(5) 0.002(3) 0.000(4) -0.001(3) C26 0.028(4) 0.017(4) 0.028(5) 0.004(3) 0.008(4) -0.002(3) C27 0.041(5) 0.031(5) 0.036(5) 0.014(4) 0.013(4) -0.014(4) P1 0.0150(9) 0.0147(9) 0.0197(11) 0.0003(8) 0.0050(8) -0.0004(8) S1 0.0326(11) 0.0163(9) 0.0344(13) 0.0038(9) 0.0159(10) 0.0041(8) S2 0.0192(9) 0.0294(10) 0.0231(12) -0.0019(9) 0.0059(8) -0.0037(8) S3 0.0252(10) 0.0290(11) 0.0230(12) 0.0087(9) 0.0058(9) -0.0015(9) Se1 0.0195(4) 0.0185(4) 0.0266(5) 0.0015(3) 0.0081(3) 0.0015(3) I1 0.0416(3) 0.0330(3) 0.0389(4) -0.0017(3) 0.0086(3) 0.0084(3) I2 0.0287(3) 0.0311(3) 0.0213(3) -0.0012(2) 0.0033(2) 0.0009(2) I3 0.0559(4) 0.0534(4) 0.0487(4) -0.0165(3) -0.0009(3) 0.0245(3) #----------------------------------------------------------------------------# # 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 1.379(10) . ? C1 C6 1.396(10) . ? C1 Se1 1.939(7) . ? C2 C3 1.367(10) . ? C3 C4 1.381(11) . ? C4 C5 1.380(11) . ? C5 C6 1.379(10) . ? C7 C12 1.403(9) . ? C7 C8 1.417(9) . ? C7 P1 1.815(7) . ? C8 C9 1.394(9) . ? C8 S1 1.760(7) . ? C9 C10 1.377(10) . ? C10 C11 1.387(10) . ? C11 C12 1.387(9) . ? C13 S1 1.802(7) . ? C14 C19 1.400(9) . ? C14 C15 1.414(9) . ? C14 P1 1.806(7) . ? C15 C16 1.387(9) . ? C15 S2 1.767(6) . ? C16 C17 1.391(9) . ? C17 C18 1.374(10) . ? C18 C19 1.381(10) . ? C20 S2 1.799(8) . ? C21 C22 1.401(9) . ? C21 C26 1.410(9) . ? C21 P1 1.811(6) . ? C22 C23 1.392(9) . ? C22 S3 1.758(7) . ? C23 C24 1.381(10) . ? C24 C25 1.367(10) . ? C25 C26 1.382(9) . ? C27 S3 1.794(7) . ? P1 Se1 2.2685(18) . ? I1 I2 2.9264(7) . ? I2 I3 2.8914(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 C2 C1 C6 121.0(7) . . ? C2 C1 Se1 122.0(6) . . ? C6 C1 Se1 117.0(5) . . ? C3 C2 C1 119.1(7) . . ? C2 C3 C4 120.4(8) . . ? C5 C4 C3 120.6(8) . . ? C6 C5 C4 119.6(8) . . ? C5 C6 C1 119.1(7) . . ? C12 C7 C8 118.6(6) . . ? C12 C7 P1 119.5(5) . . ? C8 C7 P1 121.9(5) . . ? C9 C8 C7 118.3(6) . . ? C9 C8 S1 122.0(6) . . ? C7 C8 S1 119.7(5) . . ? C10 C9 C8 122.2(7) . . ? C9 C10 C11 120.0(7) . . ? C10 C11 C12 119.0(7) . . ? C11 C12 C7 121.9(7) . . ? C19 C14 C15 118.7(6) . . ? C19 C14 P1 119.4(5) . . ? C15 C14 P1 121.9(5) . . ? C16 C15 C14 119.5(6) . . ? C16 C15 S2 121.9(5) . . ? C14 C15 S2 118.6(5) . . ? C15 C16 C17 120.4(7) . . ? C18 C17 C16 120.2(7) . . ? C17 C18 C19 120.3(7) . . ? C18 C19 C14 120.7(7) . . ? C22 C21 C26 120.0(6) . . ? C22 C21 P1 124.2(5) . . ? C26 C21 P1 115.4(5) . . ? C23 C22 C21 117.7(7) . . ? C23 C22 S3 121.7(5) . . ? C21 C22 S3 120.6(5) . . ? C24 C23 C22 121.2(7) . . ? C25 C24 C23 121.6(7) . . ? C24 C25 C26 118.6(7) . . ? C25 C26 C21 120.8(7) . . ? C14 P1 C21 111.3(3) . . ? C14 P1 C7 110.0(3) . . ? C21 P1 C7 108.6(3) . . ? C14 P1 Se1 109.5(2) . . ? C21 P1 Se1 108.9(2) . . ? C7 P1 Se1 108.6(2) . . ? C8 S1 C13 103.7(3) . . ? C15 S2 C20 102.1(4) . . ? C22 S3 C27 103.2(3) . . ? C1 Se1 P1 99.4(2) . . ? I3 I2 I1 176.56(3) . . ? # Attachment 'Ph2MePSePhI.cif' # CIF produced by WinGX routine CIF_UPDATE # Created on 2000-07-17 at 11:05:42 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.1 # Request file : c:\wingx\files\archive.dat # CIF files read : sg99d psi_scan struct data_sg99d _database_code_depnum_ccdc_archive 'CCDC 611261' _audit_creation_date 2000-07-17T11:05:42-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.1 _audit_conform_dict_location ftp://ftp.iucr.org/cifdics/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H18 I1 P1 Se1' _chemical_formula_structural 'C19 H18 I P SE1' _chemical_formula_sum 'C19 H18 I P Se' _chemical_formula_weight 483.16 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 13.292(4) _cell_length_b 16.145(4) _cell_length_c 17.331(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3719.1(15) _cell_formula_units_Z 8 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.5 _cell_measurement_theta_max 16.7 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1872 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.76 _exptl_absorpt_factor_muR 0.532 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 5 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.5201 _exptl_absorpt_correction_T_max 0.7049 _exptl_absorpt_correction_T_ave 0.5177 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_number 3259 _diffrn_reflns_av_R_equivalents 0.083 _diffrn_reflns_av_unetI/netI 0.0769 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 3259 _reflns_number_gt 2098 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0297P)^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 3259 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0973 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.0822 _refine_ls_wR_factor_gt 0.069 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.004 _refine_diff_density_max 0.498 _refine_diff_density_min -0.598 _refine_diff_density_rms 0.129 #----------------------------------------------------------------------------# # 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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.98711(3) 0.07827(3) 0.85935(3) 0.03265(14) Uani 1 d . . . Se1 Se 0.90042(5) 0.19276(5) 0.69897(4) 0.03221(19) Uani 1 d . . . P1 P 0.85620(14) 0.26837(12) 0.59686(10) 0.0284(5) Uani 1 d . . . C1 C 0.9604(5) 0.3281(5) 0.5648(4) 0.040(2) Uani 1 d . . . H1A H 1.0109 0.2916 0.5429 0.06 Uiso 1 calc R . . H1B H 0.989 0.3579 0.6081 0.06 Uiso 1 calc R . . H1C H 0.9382 0.3672 0.5259 0.06 Uiso 1 calc R . . C2 C 0.7596(5) 0.3350(4) 0.6325(4) 0.0304(17) Uani 1 d . . . C3 C 0.7839(7) 0.4117(5) 0.6620(4) 0.048(2) Uani 1 d . . . H3 H 0.8509 0.4301 0.6608 0.058 Uiso 1 calc R . . C4 C 0.7110(8) 0.4611(6) 0.6929(5) 0.063(3) Uani 1 d . . . H4 H 0.7289 0.5128 0.7136 0.076 Uiso 1 calc R . . C5 C 0.6124(8) 0.4368(6) 0.6944(4) 0.060(3) Uani 1 d . . . H5 H 0.5625 0.4714 0.7154 0.072 Uiso 1 calc R . . C6 C 0.5883(7) 0.3611(6) 0.6647(5) 0.061(3) Uani 1 d . . . H6 H 0.5209 0.3436 0.6656 0.074 Uiso 1 calc R . . C7 C 0.6600(6) 0.3098(5) 0.6336(5) 0.051(2) Uani 1 d . . . H7 H 0.6417 0.258 0.6132 0.061 Uiso 1 calc R . . C8 C 0.8086(5) 0.2042(4) 0.5206(4) 0.0275(17) Uani 1 d . . . C9 C 0.8393(5) 0.2169(5) 0.4452(4) 0.0349(19) Uani 1 d . . . H9 H 0.8864 0.2584 0.4333 0.042 Uiso 1 calc R . . C10 C 0.7998(6) 0.1679(5) 0.3880(4) 0.042(2) Uani 1 d . . . H10 H 0.8212 0.1754 0.3368 0.05 Uiso 1 calc R . . C11 C 0.7297(6) 0.1082(5) 0.4045(4) 0.039(2) Uani 1 d . . . H11 H 0.7024 0.076 0.3644 0.047 Uiso 1 calc R . . C12 C 0.6989(5) 0.0951(4) 0.4797(4) 0.0350(18) Uani 1 d . . . H12 H 0.6507 0.0544 0.4911 0.042 Uiso 1 calc R . . C13 C 0.7400(5) 0.1428(5) 0.5376(4) 0.0316(18) Uani 1 d . . . H13 H 0.721 0.1335 0.5892 0.038 Uiso 1 calc R . . C14 C 1.0205(5) 0.1501(4) 0.6502(4) 0.0321(17) Uani 1 d . . . C15 C 1.1108(5) 0.1702(5) 0.6804(4) 0.039(2) Uani 1 d . . . H15 H 1.1148 0.2037 0.7247 0.047 Uiso 1 calc R . . C16 C 1.1973(5) 0.1409(5) 0.6456(5) 0.043(2) Uani 1 d . . . H16 H 1.2605 0.1548 0.6661 0.052 Uiso 1 calc R . . C17 C 1.1915(6) 0.0915(5) 0.5813(5) 0.049(2) Uani 1 d . . . H17 H 1.2507 0.072 0.5577 0.059 Uiso 1 calc R . . C18 C 1.0994(6) 0.0707(5) 0.5514(5) 0.053(2) Uani 1 d . . . H18 H 1.0951 0.0377 0.5069 0.063 Uiso 1 calc R . . C19 C 1.0129(6) 0.0987(4) 0.5871(5) 0.045(2) Uani 1 d . . . H19 H 0.9494 0.0828 0.5684 0.053 Uiso 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 I1 0.0309(2) 0.0374(3) 0.0296(2) -0.0021(2) -0.0032(2) 0.0034(3) Se1 0.0297(4) 0.0372(4) 0.0297(4) 0.0023(4) 0.0021(3) 0.0014(4) P1 0.0282(10) 0.0285(12) 0.0287(10) 0.0034(9) 0.0013(8) -0.0033(9) C1 0.031(4) 0.049(5) 0.040(4) 0.004(4) -0.001(3) -0.014(4) C2 0.038(4) 0.022(4) 0.031(4) -0.006(3) -0.005(4) 0.006(3) C3 0.062(5) 0.026(5) 0.057(5) -0.004(4) 0.001(4) -0.004(5) C4 0.099(8) 0.030(5) 0.061(6) -0.011(5) -0.002(6) 0.017(6) C5 0.089(7) 0.059(7) 0.032(4) -0.005(5) 0.008(5) 0.037(6) C6 0.046(5) 0.077(7) 0.061(6) -0.023(5) 0.004(4) 0.016(6) C7 0.046(5) 0.046(5) 0.060(5) -0.027(5) -0.008(4) 0.002(5) C8 0.024(4) 0.031(4) 0.027(4) 0.001(3) 0.006(3) 0.009(4) C9 0.036(4) 0.034(5) 0.035(4) 0.001(4) 0.002(4) -0.007(4) C10 0.057(5) 0.043(6) 0.025(4) 0.008(4) 0.000(4) 0.006(5) C11 0.045(5) 0.037(5) 0.036(4) -0.010(4) -0.005(4) 0.003(4) C12 0.026(4) 0.030(5) 0.050(5) -0.006(4) 0.001(4) 0.001(4) C13 0.029(4) 0.039(5) 0.027(4) -0.002(3) 0.003(3) 0.004(4) C14 0.025(4) 0.034(4) 0.037(4) 0.007(4) -0.002(4) -0.002(4) C15 0.036(5) 0.048(5) 0.032(4) 0.004(4) -0.003(4) 0.002(4) C16 0.022(4) 0.050(5) 0.057(5) 0.003(5) 0.001(4) -0.003(4) C17 0.038(5) 0.044(6) 0.064(6) -0.009(5) 0.004(4) 0.004(5) C18 0.059(6) 0.036(5) 0.063(5) -0.023(4) -0.005(5) 0.011(5) C19 0.030(4) 0.039(5) 0.065(5) -0.018(4) -0.009(4) 0.008(4) #----------------------------------------------------------------------------# # 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 Se1 C14 1.932(7) . ? Se1 P1 2.2288(19) . ? P1 C1 1.776(7) . ? P1 C8 1.794(7) . ? P1 C2 1.785(7) . ? C2 C3 1.379(10) . ? C2 C7 1.384(10) . ? C3 C4 1.364(11) . ? C4 C5 1.369(12) . ? C5 C6 1.364(12) . ? C6 C7 1.373(10) . ? C8 C13 1.379(9) . ? C8 C9 1.384(9) . ? C9 C10 1.372(9) . ? C10 C11 1.371(10) . ? C11 C12 1.382(9) . ? C12 C13 1.379(9) . ? C14 C15 1.349(9) . ? C14 C19 1.377(9) . ? C15 C16 1.383(9) . ? C16 C17 1.372(10) . ? C17 C18 1.372(10) . ? C18 C19 1.381(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 Se1 P1 93.8(2) . . ? C1 P1 C8 111.0(3) . . ? C1 P1 C2 110.0(4) . . ? C8 P1 C2 110.4(3) . . ? C1 P1 Se1 109.9(2) . . ? C8 P1 Se1 111.2(2) . . ? C2 P1 Se1 104.2(2) . . ? C3 C2 C7 118.8(7) . . ? C3 C2 P1 120.1(6) . . ? C7 C2 P1 121.0(6) . . ? C4 C3 C2 120.3(8) . . ? C5 C4 C3 121.3(9) . . ? C4 C5 C6 118.3(8) . . ? C5 C6 C7 121.7(9) . . ? C6 C7 C2 119.5(8) . . ? C13 C8 C9 120.2(7) . . ? C13 C8 P1 119.3(5) . . ? C9 C8 P1 120.4(5) . . ? C10 C9 C8 118.9(7) . . ? C9 C10 C11 121.0(7) . . ? C10 C11 C12 120.3(7) . . ? C13 C12 C11 119.0(7) . . ? C12 C13 C8 120.5(6) . . ? C15 C14 C19 121.2(7) . . ? C15 C14 Se1 118.7(6) . . ? C19 C14 Se1 120.1(5) . . ? C14 C15 C16 119.3(7) . . ? C17 C16 C15 120.5(7) . . ? C16 C17 C18 119.9(7) . . ? C19 C18 C17 119.6(7) . . ? C18 C19 C14 119.5(7) . . ? # Attachment 'Ph2MePSePhICH2Cl2.cif' data_t _database_code_depnum_ccdc_archive 'CCDC 611262' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19.75 H19.50 Cl1.50 I P Se' _chemical_formula_sum 'C19.75 H19.50 Cl1.50 I P Se' _chemical_formula_weight 546.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 21.908(3) _cell_length_b 10.4978(10) _cell_length_c 20.798(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.58(2) _cell_angle_gamma 90.00 _cell_volume 4277.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 10.4 _cell_measurement_theta_max 17.9 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2124 _exptl_absorpt_coefficient_mu 3.461 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.4233 _exptl_absorpt_correction_T_max 0.5444 _exptl_absorpt_process_details ; North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351 Number of psi-scan sets used was 4 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7751 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0515 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7517 _reflns_number_gt 5263 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^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_extinction_coef ? _refine_ls_number_reflns 7517 _refine_ls_number_parameters 440 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1539 _refine_ls_wR_factor_gt 0.1321 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.046 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.074437(17) 0.75450(3) 0.34613(2) 0.03481(10) Uani 1 1 d . . . Se1 Se 0.09392(3) 0.42690(5) 0.37664(3) 0.03358(14) Uani 1 1 d . . . P1 P 0.09843(7) 0.21974(13) 0.40083(7) 0.0289(3) Uani 1 1 d . . . C1 C 0.0286(2) 0.1927(5) 0.4217(3) 0.0323(14) Uani 1 1 d . . . C2 C -0.0378(3) 0.1963(7) 0.3670(4) 0.054(2) Uani 1 1 d . . . H2 H -0.0458 0.2104 0.3192 0.065 Uiso 1 1 calc R . . C3 C -0.0913(3) 0.1794(8) 0.3827(4) 0.070(3) Uani 1 1 d . . . H3 H -0.1361 0.1779 0.3454 0.084 Uiso 1 1 calc R . . C4 C -0.0802(3) 0.1644(6) 0.4533(4) 0.0557(18) Uani 1 1 d . . . H4 H -0.1173 0.1566 0.4643 0.067 Uiso 1 1 calc R . . C5 C -0.0147(3) 0.1611(7) 0.5068(4) 0.058(2) Uani 1 1 d . . . H5 H -0.0066 0.1498 0.5547 0.070 Uiso 1 1 calc R . . C6 C 0.0388(3) 0.1738(6) 0.4912(3) 0.0458(17) Uani 1 1 d . . . H6 H 0.0836 0.1696 0.5284 0.055 Uiso 1 1 calc R . . C7 C 0.1756(2) 0.1771(5) 0.4777(3) 0.0333(14) Uani 1 1 d . . . C8 C 0.2116(3) 0.2685(6) 0.5302(3) 0.0428(17) Uani 1 1 d . . . H8 H 0.1967 0.3536 0.5244 0.051 Uiso 1 1 calc R . . C9 C 0.2703(3) 0.2308(6) 0.5916(4) 0.052(2) Uani 1 1 d . . . H9 H 0.2948 0.2908 0.6275 0.062 Uiso 1 1 calc R . . C10 C 0.2917(3) 0.1082(7) 0.5991(4) 0.058(2) Uani 1 1 d . . . H10 H 0.3319 0.0851 0.6398 0.070 Uiso 1 1 calc R . . C11 C 0.2557(3) 0.0152(7) 0.5482(4) 0.060(2) Uani 1 1 d . . . H11 H 0.2709 -0.0697 0.5547 0.072 Uiso 1 1 calc R . . C12 C 0.1966(3) 0.0510(6) 0.4875(3) 0.0395(16) Uani 1 1 d . . . H12 H 0.1710 -0.0105 0.4531 0.047 Uiso 1 1 calc R . . C13 C 0.0897(3) 0.1272(5) 0.3253(3) 0.0329(14) Uani 1 1 d . . . H13A H 0.1268 0.1471 0.3135 0.049 Uiso 1 1 calc R . . H13B H 0.0465 0.1467 0.2844 0.049 Uiso 1 1 calc R . . H13C H 0.0912 0.0373 0.3368 0.049 Uiso 1 1 calc R . . C14 C 0.1515(2) 0.4161(5) 0.3285(3) 0.0316(14) Uani 1 1 d . . . C15 C 0.1203(3) 0.4150(7) 0.2546(3) 0.054(2) Uani 1 1 d . . . H15 H 0.0724 0.4174 0.2287 0.065 Uiso 1 1 calc R . . C16 C 0.1607(4) 0.4103(8) 0.2191(4) 0.071(2) Uani 1 1 d . . . H16 H 0.1401 0.4116 0.1686 0.085 Uiso 1 1 calc R . . C17 C 0.2296(3) 0.4038(7) 0.2565(4) 0.063(2) Uani 1 1 d . . . H17 H 0.2564 0.3980 0.2318 0.075 Uiso 1 1 calc R . . C18 C 0.2605(3) 0.4056(6) 0.3304(4) 0.058(2) Uani 1 1 d . . . H18 H 0.3084 0.4032 0.3560 0.070 Uiso 1 1 calc R . . C19 C 0.2213(3) 0.4111(6) 0.3673(3) 0.0441(17) Uani 1 1 d . . . H19 H 0.2420 0.4113 0.4178 0.053 Uiso 1 1 calc R . . I2 I 0.577412(17) 0.71936(3) 0.70223(2) 0.03558(10) Uani 1 1 d . . . Se2 Se 0.58818(3) 0.39051(5) 0.73966(3) 0.03464(15) Uani 1 1 d . . . P2 P 0.61905(6) 0.18747(13) 0.75996(7) 0.0271(3) Uani 1 1 d . . . C21 C 0.6666(2) 0.1757(5) 0.8562(3) 0.0317(14) Uani 1 1 d . . . C22 C 0.6322(3) 0.1971(7) 0.8976(3) 0.0494(19) Uani 1 1 d . . . H22 H 0.5850 0.2126 0.8754 0.059 Uiso 1 1 calc R . . C23 C 0.6683(3) 0.1952(8) 0.9714(3) 0.065(2) Uani 1 1 d . . . H23 H 0.6459 0.2122 0.9999 0.078 Uiso 1 1 calc R . . C24 C 0.7377(3) 0.1685(7) 1.0040(3) 0.0517(19) Uani 1 1 d . . . H24 H 0.7620 0.1655 1.0544 0.062 Uiso 1 1 calc R . . C25 C 0.7704(3) 0.1465(6) 0.9627(3) 0.0481(19) Uani 1 1 d . . . H25 H 0.8175 0.1294 0.9850 0.058 Uiso 1 1 calc R . . C26 C 0.7353(3) 0.1492(6) 0.8882(3) 0.0418(17) Uani 1 1 d . . . H26 H 0.7581 0.1331 0.8601 0.050 Uiso 1 1 calc R . . C27 C 0.6739(2) 0.1518(5) 0.7186(3) 0.0292(13) Uani 1 1 d . . . C28 C 0.7194(3) 0.2425(6) 0.7195(3) 0.0421(17) Uani 1 1 d . . . H28 H 0.7219 0.3218 0.7415 0.051 Uiso 1 1 calc R . . C29 C 0.7614(3) 0.2161(7) 0.6879(3) 0.0475(18) Uani 1 1 d . . . H29 H 0.7929 0.2777 0.6887 0.057 Uiso 1 1 calc R . . C30 C 0.7579(3) 0.1032(7) 0.6557(4) 0.064(2) Uani 1 1 d . . . H30 H 0.7861 0.0865 0.6334 0.077 Uiso 1 1 calc R . . C31 C 0.7126(3) 0.0121(8) 0.6559(4) 0.072(2) Uani 1 1 d . . . H31 H 0.7108 -0.0675 0.6344 0.086 Uiso 1 1 calc R . . C32 C 0.6705(3) 0.0359(6) 0.6869(4) 0.0528(17) Uani 1 1 d . . . H32 H 0.6396 -0.0264 0.6865 0.063 Uiso 1 1 calc R . . C33 C 0.5479(3) 0.0813(5) 0.7276(3) 0.0375(15) Uani 1 1 d . . . H33A H 0.5203 0.0950 0.6765 0.056 Uiso 1 1 calc R . . H33B H 0.5207 0.0972 0.7528 0.056 Uiso 1 1 calc R . . H33C H 0.5642 -0.0060 0.7358 0.056 Uiso 1 1 calc R . . C34 C 0.5268(3) 0.3644(5) 0.6397(3) 0.0316(14) Uani 1 1 d . . . C35 C 0.4599(3) 0.3419(7) 0.6196(3) 0.053(2) Uani 1 1 d . . . H35 H 0.4435 0.3390 0.6544 0.063 Uiso 1 1 calc R . . C36 C 0.4160(3) 0.3233(8) 0.5483(4) 0.064(2) Uani 1 1 d . . . H36 H 0.3694 0.3094 0.5345 0.076 Uiso 1 1 calc R . . C37 C 0.4391(4) 0.3248(8) 0.4967(4) 0.064(2) Uani 1 1 d . . . H37 H 0.4090 0.3102 0.4481 0.076 Uiso 1 1 calc R . . C38 C 0.5065(3) 0.3479(7) 0.5178(3) 0.058(2) Uani 1 1 d . . . H38 H 0.5229 0.3504 0.4831 0.070 Uiso 1 1 calc R . . C39 C 0.5511(3) 0.3678(6) 0.5888(3) 0.0440(17) Uani 1 1 d . . . H39 H 0.5975 0.3834 0.6026 0.053 Uiso 1 1 calc R . . C40 C -0.0703(4) 0.5414(11) 0.3803(5) 0.191(4) Uani 1 1 d D . . H40A H -0.0513 0.4688 0.3657 0.230 Uiso 1 1 calc R . . H40B H -0.0398 0.6148 0.3900 0.230 Uiso 1 1 calc R . . Cl1 Cl -0.0835(2) 0.5050(4) 0.4529(3) 0.209(2) Uani 1 1 d D . . Cl2 Cl -0.1545(3) 0.5779(6) 0.3141(2) 0.255(3) Uani 1 1 d D . . C41 C 0.5203(5) 0.9983(18) 0.5341(6) 0.079(5) Uiso 0.50 1 d PD . . H41A H 0.5440 0.9237 0.5627 0.095 Uiso 0.50 1 calc PR . . H41B H 0.5370 1.0707 0.5672 0.095 Uiso 0.50 1 calc PR . . Cl3 Cl 0.4424(3) 0.9803(4) 0.5219(3) 0.267(4) Uani 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.03374(16) 0.03273(19) 0.03730(18) -0.00134(15) 0.01531(13) -0.00172(14) Se1 0.0362(2) 0.0269(3) 0.0396(3) 0.0061(2) 0.0186(2) 0.0033(2) P1 0.0325(6) 0.0261(7) 0.0291(6) 0.0027(6) 0.0147(5) 0.0013(5) C1 0.032(2) 0.025(3) 0.043(3) 0.000(2) 0.019(2) -0.003(2) C2 0.038(3) 0.079(5) 0.041(3) 0.002(3) 0.014(3) -0.008(3) C3 0.037(3) 0.093(6) 0.074(5) -0.012(4) 0.021(3) -0.009(4) C4 0.060(3) 0.044(4) 0.090(4) 0.000(3) 0.058(3) -0.004(3) C5 0.066(3) 0.069(5) 0.062(3) 0.015(3) 0.048(3) 0.008(3) C6 0.048(3) 0.050(4) 0.047(3) 0.010(3) 0.028(2) -0.001(3) C7 0.031(2) 0.035(3) 0.035(3) 0.005(2) 0.015(2) 0.002(2) C8 0.040(3) 0.035(3) 0.042(3) 0.006(3) 0.009(3) 0.005(3) C9 0.050(3) 0.049(4) 0.051(4) 0.000(3) 0.017(3) -0.010(3) C10 0.043(3) 0.063(5) 0.056(4) 0.017(4) 0.012(3) 0.008(3) C11 0.070(4) 0.040(4) 0.054(4) 0.005(3) 0.013(3) 0.013(3) C12 0.043(3) 0.035(3) 0.037(3) -0.001(3) 0.015(2) 0.004(3) C13 0.046(3) 0.030(3) 0.020(2) 0.000(2) 0.011(2) 0.007(2) C14 0.032(2) 0.026(3) 0.037(3) 0.007(2) 0.015(2) 0.002(2) C15 0.050(3) 0.074(5) 0.044(3) 0.011(3) 0.025(3) -0.002(3) C16 0.078(4) 0.089(6) 0.052(4) 0.016(4) 0.035(3) -0.005(4) C17 0.062(3) 0.069(5) 0.082(4) 0.005(4) 0.054(3) -0.004(3) C18 0.036(3) 0.050(4) 0.094(5) 0.016(4) 0.035(3) 0.010(3) C19 0.032(3) 0.047(4) 0.052(3) 0.005(3) 0.018(2) 0.005(3) I2 0.03721(16) 0.03156(19) 0.04083(18) 0.00260(15) 0.02000(14) 0.00161(15) Se2 0.0402(3) 0.0291(3) 0.0310(3) -0.0025(2) 0.0127(2) 0.0053(2) P2 0.0287(6) 0.0262(7) 0.0282(6) 0.0001(5) 0.0144(5) 0.0011(5) C21 0.034(2) 0.032(3) 0.027(2) 0.006(2) 0.013(2) 0.005(2) C22 0.026(2) 0.090(5) 0.032(3) -0.004(3) 0.013(2) -0.003(3) C23 0.054(3) 0.106(6) 0.042(3) 0.000(4) 0.029(3) -0.020(4) C24 0.052(3) 0.061(4) 0.038(3) 0.005(3) 0.016(3) -0.007(3) C25 0.042(3) 0.049(4) 0.039(3) 0.015(3) 0.004(3) 0.009(3) C26 0.038(3) 0.041(3) 0.046(3) 0.009(3) 0.019(2) 0.007(3) C27 0.027(2) 0.032(3) 0.030(2) 0.007(2) 0.0145(19) 0.003(2) C28 0.041(3) 0.040(3) 0.045(3) 0.000(3) 0.019(2) 0.001(3) C29 0.036(3) 0.061(4) 0.055(3) 0.008(3) 0.029(2) 0.002(3) C30 0.070(3) 0.063(5) 0.091(4) -0.002(4) 0.064(3) 0.006(3) C31 0.092(4) 0.061(4) 0.096(4) -0.034(4) 0.071(3) -0.015(4) C32 0.063(3) 0.040(3) 0.076(4) -0.012(3) 0.050(3) -0.012(3) C33 0.033(2) 0.035(3) 0.046(3) -0.008(3) 0.019(2) -0.005(2) C34 0.036(2) 0.032(3) 0.024(2) 0.001(2) 0.011(2) 0.008(2) C35 0.040(3) 0.087(5) 0.035(3) 0.008(3) 0.020(2) 0.007(3) C36 0.037(3) 0.094(6) 0.045(4) -0.010(4) 0.005(3) 0.004(4) C37 0.062(4) 0.080(5) 0.032(3) 0.004(4) 0.006(3) 0.009(4) C38 0.068(4) 0.076(5) 0.032(3) 0.012(3) 0.023(3) 0.008(4) C39 0.043(3) 0.047(4) 0.042(3) 0.008(3) 0.019(2) 0.004(3) C40 0.146(5) 0.143(9) 0.385(11) -0.144(8) 0.209(6) -0.077(6) Cl1 0.204(4) 0.141(3) 0.200(4) 0.025(3) 0.018(3) -0.031(3) Cl2 0.249(4) 0.348(7) 0.138(3) 0.055(4) 0.060(3) -0.110(5) Cl3 0.410(8) 0.102(3) 0.191(4) 0.027(3) 0.046(5) -0.016(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 C14 1.933(6) . ? Se1 P1 2.2243(15) . ? P1 C13 1.784(5) . ? P1 C7 1.787(5) . ? P1 C1 1.790(6) . ? C1 C6 1.373(8) . ? C1 C2 1.390(7) . ? C2 C3 1.362(10) . ? C3 C4 1.386(11) . ? C4 C5 1.368(8) . ? C5 C6 1.356(9) . ? C7 C12 1.386(8) . ? C7 C8 1.402(8) . ? C8 C9 1.404(8) . ? C9 C10 1.355(10) . ? C10 C11 1.396(9) . ? C11 C12 1.397(8) . ? C14 C19 1.374(7) . ? C14 C15 1.374(8) . ? C15 C16 1.384(10) . ? C16 C17 1.356(9) . ? C17 C18 1.375(10) . ? C18 C19 1.384(10) . ? Se2 C34 1.924(5) . ? Se2 P2 2.2189(15) . ? P2 C33 1.785(5) . ? P2 C21 1.800(5) . ? P2 C27 1.802(6) . ? C21 C26 1.375(7) . ? C21 C22 1.391(9) . ? C22 C23 1.378(8) . ? C23 C24 1.388(9) . ? C24 C25 1.363(10) . ? C25 C26 1.388(8) . ? C27 C32 1.369(8) . ? C27 C28 1.373(8) . ? C28 C29 1.379(9) . ? C29 C30 1.346(10) . ? C30 C31 1.379(10) . ? C31 C32 1.364(10) . ? C34 C35 1.355(8) . ? C34 C39 1.381(9) . ? C35 C36 1.373(8) . ? C36 C37 1.376(11) . ? C37 C38 1.362(10) . ? C38 C39 1.374(8) . ? C40 Cl1 1.702(11) . ? C40 Cl2 1.781(9) . ? C41 Cl3 1.620(11) . ? C41 Cl3 1.710(13) 3_676 ? Cl3 C41 1.710(13) 3_676 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 Se1 P1 94.98(16) . . ? C13 P1 C7 109.7(3) . . ? C13 P1 C1 111.2(3) . . ? C7 P1 C1 108.2(3) . . ? C13 P1 Se1 110.91(19) . . ? C7 P1 Se1 112.08(19) . . ? C1 P1 Se1 104.68(18) . . ? C6 C1 C2 118.9(6) . . ? C6 C1 P1 121.5(4) . . ? C2 C1 P1 119.5(5) . . ? C3 C2 C1 119.9(6) . . ? C2 C3 C4 120.5(6) . . ? C5 C4 C3 119.1(6) . . ? C6 C5 C4 120.6(6) . . ? C5 C6 C1 120.9(5) . . ? C12 C7 C8 120.3(5) . . ? C12 C7 P1 119.3(4) . . ? C8 C7 P1 120.2(4) . . ? C7 C8 C9 118.9(6) . . ? C10 C9 C8 120.1(6) . . ? C9 C10 C11 121.9(6) . . ? C10 C11 C12 118.6(6) . . ? C7 C12 C11 120.2(5) . . ? C19 C14 C15 121.5(6) . . ? C19 C14 Se1 120.7(5) . . ? C15 C14 Se1 117.8(4) . . ? C14 C15 C16 118.6(6) . . ? C17 C16 C15 120.6(7) . . ? C16 C17 C18 120.4(7) . . ? C17 C18 C19 120.1(6) . . ? C14 C19 C18 118.7(6) . . ? C34 Se2 P2 94.30(17) . . ? C33 P2 C21 110.5(3) . . ? C33 P2 C27 110.2(3) . . ? C21 P2 C27 109.8(2) . . ? C33 P2 Se2 112.81(19) . . ? C21 P2 Se2 104.66(19) . . ? C27 P2 Se2 108.68(19) . . ? C26 C21 C22 120.7(5) . . ? C26 C21 P2 121.0(5) . . ? C22 C21 P2 118.2(4) . . ? C23 C22 C21 119.2(5) . . ? C22 C23 C24 120.3(7) . . ? C25 C24 C23 119.7(6) . . ? C24 C25 C26 121.0(6) . . ? C21 C26 C25 119.0(6) . . ? C32 C27 C28 120.3(6) . . ? C32 C27 P2 120.7(4) . . ? C28 C27 P2 119.0(5) . . ? C27 C28 C29 119.3(6) . . ? C30 C29 C28 120.8(6) . . ? C29 C30 C31 119.4(7) . . ? C32 C31 C30 120.9(7) . . ? C31 C32 C27 119.2(6) . . ? C35 C34 C39 120.2(5) . . ? C35 C34 Se2 119.7(5) . . ? C39 C34 Se2 120.1(4) . . ? C34 C35 C36 119.7(7) . . ? C35 C36 C37 121.1(6) . . ? C38 C37 C36 118.4(6) . . ? C37 C38 C39 121.3(7) . . ? C38 C39 C34 119.2(6) . . ? Cl1 C40 Cl2 101.9(5) . . ? Cl3 C41 Cl3 134.3(8) . 3_676 ? C41 Cl3 C41 45.7(8) . 3_676 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.730 _refine_diff_density_min -1.695 _refine_diff_density_rms 0.139