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 ; Chemistry (north Campus) University of Manchester Faraday Building Sackville Street PO Box 88 Manchester Lancashire M60 1QD UNITED KINGDOM ; _publ_contact_author_email STEPHEN.GODFREY@MANCHESTER.AC.UK _publ_section_title ; Reactions of Ph4Se4Br4 with tertiary phosphines. Structural isomerism within a series of R3PSe(Ph)Br compounds. ; _publ_requested_category FO loop_ _publ_author_name 'Stephen Godfrey' 'Nicholas A. Barnes' 'Ruth T. A. Halton' 'Imrana Mushtaq' 'Robin G. Pritchard' ; S.Sarwar ; # Attachment 'me3psephbr.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2005-07-04 at 22:52:40 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : s dreduc sortav struct data_s _database_code_depnum_ccdc_archive 'CCDC 279360' _audit_creation_date 2005-07-04T22:52:40-00:00 _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 'C9 H14 Br1 P1 Se1' _chemical_formula_sum 'C9 H14 Br P Se' _chemical_formula_weight 312.04 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.8100(11) _cell_length_b 9.5140(18) _cell_length_c 18.657(4) _cell_angle_alpha 90 _cell_angle_beta 92.469(7) _cell_angle_gamma 90 _cell_volume 1207.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1464 _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 0.2 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.716 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 6.502 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.1976 _exptl_absorpt_correction_T_max 0.8827 #----------------------------------------------------------------------------# # 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 -0.128968 _diffrn_orient_matrix_ub_12 -0.414103E-1 _diffrn_orient_matrix_ub_13 -0.165868E-1 _diffrn_orient_matrix_ub_21 0.361687E-1 _diffrn_orient_matrix_ub_22 0.119475E-1 _diffrn_orient_matrix_ub_23 -0.51111E-1 _diffrn_orient_matrix_ub_31 0.602815E-1 _diffrn_orient_matrix_ub_32 -0.957626E-1 _diffrn_orient_matrix_ub_33 0.7959E-3 _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 0.037 _diffrn_reflns_av_unetI/netI 0.0623 _diffrn_reflns_number 3058 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 25.25 _diffrn_reflns_theta_full 25.25 _diffrn_measured_fraction_theta_full 0.911 _diffrn_measured_fraction_theta_max 0.911 _reflns_number_total 1990 _reflns_number_gt 1581 _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. The current compound crystallised as stacks of extremely thin crystals. Several attempts were needed to mount an indexable "singel-crystal". Data processing revealed that even this crystal was not single, being a non-merahedral twin (twin axis 0 0 1, twin components ratio 6:4). Despite allowing for the major twin component the diffraction pattern was extremely heavily streaked, suggesting several further misaligned minor components. Despite omitting the 40 reflections with the worse agreements the final R factors still converged to relatively high values. ; _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^)+(0.1854P)^2^+18.4020P] 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 0.006(3) _refine_ls_number_reflns 1990 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.135 _refine_ls_R_factor_gt 0.1132 _refine_ls_wR_factor_ref 0.3133 _refine_ls_wR_factor_gt 0.2876 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 _refine_diff_density_max 2.51 _refine_diff_density_min -2.131 _refine_diff_density_rms 0.34 #----------------------------------------------------------------------------# # 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' Br Br -0.291 2.4679 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1026 0.0946 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0922 2.2336 '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 0.251(3) 1.5304(17) 0.2787(9) 0.039(4) Uani 1 1 d . . . H1A H 0.1365 1.4964 0.3038 0.059 Uiso 1 1 calc R . . H1B H 0.2496 1.6334 0.2778 0.059 Uiso 1 1 calc R . . H1C H 0.3715 1.4975 0.3037 0.059 Uiso 1 1 calc R . . C2 C 0.453(3) 1.5310(18) 0.1471(10) 0.043(4) Uani 1 1 d . . . H2A H 0.4525 1.4979 0.0973 0.064 Uiso 1 1 calc R . . H2B H 0.572 1.4972 0.1731 0.064 Uiso 1 1 calc R . . H2C H 0.4512 1.634 0.1477 0.064 Uiso 1 1 calc R . . C3 C 0.018(3) 1.526(2) 0.1411(11) 0.050(5) Uani 1 1 d . . . H3A H -0.0973 1.4896 0.1647 0.075 Uiso 1 1 calc R . . H3B H 0.017 1.4916 0.0915 0.075 Uiso 1 1 calc R . . H3C H 0.0152 1.6288 0.1412 0.075 Uiso 1 1 calc R . . C4 C 0.279(3) 1.209(2) 0.0939(9) 0.048(5) Uani 1 1 d . . . C5 C 0.472(3) 1.2097(18) 0.0665(12) 0.051(5) Uani 1 1 d . . . H5 H 0.5849 1.2236 0.0976 0.062 Uiso 1 1 calc R . . C6 C 0.120(3) 1.1832(19) 0.0475(11) 0.049(5) Uani 1 1 d . . . H6 H -0.0094 1.1786 0.0641 0.059 Uiso 1 1 calc R . . C7 C 0.492(4) 1.190(2) -0.0064(13) 0.072(9) Uani 1 1 d . . . H7 H 0.6182 1.1926 -0.0259 0.087 Uiso 1 1 calc R . . C8 C 0.330(4) 1.167(2) -0.0503(11) 0.063(6) Uani 1 1 d . . . H8 H 0.3431 1.1516 -0.1002 0.076 Uiso 1 1 calc R . . C9 C 0.156(4) 1.1648(17) -0.0232(12) 0.062(6) Uani 1 1 d . . . H9 H 0.0462 1.1495 -0.0553 0.074 Uiso 1 1 calc R . . Br1 Br 0.2413(3) 0.8809(2) 0.19066(11) 0.0491(7) Uani 1 1 d . . . Se1 Se 0.2436(2) 1.23056(17) 0.19440(9) 0.0343(7) Uani 1 1 d . . . P1 P 0.2405(6) 1.4651(4) 0.1893(2) 0.0335(10) 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 0.035(9) 0.035(9) 0.048(10) 0.000(7) 0.015(8) 0.005(8) C2 0.050(11) 0.026(9) 0.053(11) 0.002(7) 0.019(9) 0.001(8) C3 0.032(10) 0.050(12) 0.069(13) 0.010(10) 0.004(9) 0.001(9) C4 0.072(14) 0.045(9) 0.026(8) 0.007(7) 0.003(9) 0.001(10) C5 0.046(10) 0.022(8) 0.086(15) 0.013(9) -0.001(10) 0.000(8) C6 0.046(10) 0.042(10) 0.058(12) 0.006(9) -0.022(9) 0.010(9) C7 0.10(2) 0.040(11) 0.080(17) 0.024(12) 0.064(17) 0.014(13) C8 0.10(2) 0.051(12) 0.037(11) -0.009(9) 0.018(12) 0.007(14) C9 0.107(19) 0.017(8) 0.060(13) -0.003(8) 0.005(13) -0.020(11) Br1 0.0407(11) 0.0391(11) 0.0677(14) -0.0022(8) 0.0059(9) 0.0001(8) Se1 0.0324(10) 0.0266(9) 0.0441(11) 0.0025(7) 0.0055(7) -0.0019(6) P1 0.031(2) 0.0232(19) 0.046(3) 0.0013(17) 0.0033(18) 0.0011(17) #----------------------------------------------------------------------------# # 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 P1 1.779(18) . ? C1 H1A 0.98 . ? C1 H1B 0.98 . ? C1 H1C 0.98 . ? C2 P1 1.792(17) . ? C2 H2A 0.98 . ? C2 H2B 0.98 . ? C2 H2C 0.98 . ? C3 P1 1.821(19) . ? C3 H3A 0.98 . ? C3 H3B 0.98 . ? C3 H3C 0.98 . ? C4 C5 1.43(3) . ? C4 Se1 1.913(17) . ? C5 C7 1.39(3) . ? C5 H5 0.95 . ? C6 C9 1.36(3) . ? C6 C4 1.38(3) . ? C6 H6 0.95 . ? C7 H7 0.95 . ? C8 C9 1.31(3) . ? C8 C7 1.36(4) . ? C8 H8 0.95 . ? C9 H9 0.95 . ? Se1 P1 2.233(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 C1 H1A 109.5 . . ? P1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? P1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? P1 C2 H2A 109.5 . . ? P1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? P1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? P1 C3 H3A 109.5 . . ? P1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? P1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C6 C4 C5 119.1(18) . . ? C6 C4 Se1 120.3(16) . . ? C5 C4 Se1 120.5(15) . . ? C7 C5 C4 118(2) . . ? C7 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C9 C6 C4 117(2) . . ? C9 C6 H6 121.3 . . ? C4 C6 H6 121.3 . . ? C8 C7 C5 120(2) . . ? C8 C7 H7 119.9 . . ? C5 C7 H7 119.9 . . ? C9 C8 C7 119(2) . . ? C9 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? C8 C9 C6 125(2) . . ? C8 C9 H9 117.4 . . ? C6 C9 H9 117.4 . . ? C4 Se1 P1 93.9(6) . . ? C1 P1 C2 106.9(9) . . ? C1 P1 C3 110.5(9) . . ? C2 P1 C3 110.0(9) . . ? C1 P1 Se1 108.0(6) . . ? C2 P1 Se1 111.3(6) . . ? C3 P1 Se1 110.1(7) . . ? 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 C9 C6 C4 C5 -2(3) . . . . ? C9 C6 C4 Se1 -178.3(13) . . . . ? C6 C4 C5 C7 2(3) . . . . ? Se1 C4 C5 C7 178.4(13) . . . . ? C7 C8 C9 C6 -1(3) . . . . ? C4 C6 C9 C8 1(3) . . . . ? C9 C8 C7 C5 1(3) . . . . ? C4 C5 C7 C8 -2(3) . . . . ? C6 C4 Se1 P1 -97.2(15) . . . . ? C5 C4 Se1 P1 86.7(15) . . . . ? C4 Se1 P1 C1 -170.2(9) . . . . ? C4 Se1 P1 C2 -53.2(10) . . . . ? C4 Se1 P1 C3 69.1(10) . . . . ? # Attachment 'ph4se4br4.cif' # CIF produced by WinGX routine CIF_UPDATE # Created on 2000-07-06 at 09:28:10 # 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 : p dreduc psi_scan struct data_p _database_code_depnum_ccdc_archive 'CCDC 290834' _audit_creation_date 2000-07-06T09:28:10-00:00 _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 'C6 H5 Br1 Se1' _chemical_formula_structural 'C6 H5 Br1 Se1' _chemical_formula_sum 'C6 H5 Br Se' _chemical_formula_weight 235.97 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.172(2) _cell_length_b 13.183(2) _cell_length_c 15.724(3) _cell_angle_alpha 90 _cell_angle_beta 101.47(2) _cell_angle_gamma 90 _cell_volume 2675.9(8) _cell_formula_units_Z 16 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.3 _cell_measurement_theta_max 18.4 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 2.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 11.47 _exptl_absorpt_factor_muR 0 _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 3 Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied. ; _exptl_absorpt_correction_T_min 0.0516 _exptl_absorpt_correction_T_max 0.5007 _exptl_absorpt_correction_T_ave 0.7325 #----------------------------------------------------------------------------# # 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 -0.11911E-1 _diffrn_orient_matrix_ub_12 -0.27263E-1 _diffrn_orient_matrix_ub_13 -0.60529E-1 _diffrn_orient_matrix_ub_21 0.25684E-1 _diffrn_orient_matrix_ub_22 -0.68031E-1 _diffrn_orient_matrix_ub_23 0.22992E-1 _diffrn_orient_matrix_ub_31 -0.72111E-1 _diffrn_orient_matrix_ub_32 -0.19552E-1 _diffrn_orient_matrix_ub_33 0.4318E-2 _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_% 0 _diffrn_standards_decay_corr_max 1.02 _diffrn_standards_decay_corr_min 0.963 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -4 0 8 5 -5 -8 6 -6 -5 _diffrn_reflns_number 4663 _diffrn_reflns_av_R_equivalents 0.0832 _diffrn_reflns_av_unetI/netI 0.0744 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 4663 _reflns_number_gt 3597 _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, 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^)+(0.0537P)^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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4663 _refine_ls_number_parameters 289 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1132 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(4) _refine_diff_density_max 0.832 _refine_diff_density_min -0.727 _refine_diff_density_rms 0.159 #----------------------------------------------------------------------------# # 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 Br1 Br 0.65562(13) 0.62353(11) 0.26975(11) 0.0375(4) Uani 1 1 d . . . Br2 Br 1.04315(12) 0.38916(12) 0.26617(10) 0.0372(4) Uani 1 1 d . . . Br3 Br 0.80544(13) -0.00391(11) 0.27198(11) 0.0366(4) Uani 1 1 d . . . Br4 Br 0.41581(12) 0.23880(12) 0.26977(11) 0.0376(4) Uani 1 1 d . . . Se1 Se 0.63708(12) 0.44317(11) 0.26489(10) 0.0255(3) Uani 1 1 d . . . Se2 Se 0.86419(11) 0.40275(11) 0.27379(9) 0.0263(3) Uani 1 1 d . . . Se3 Se 0.82060(12) 0.17557(11) 0.26301(10) 0.0263(4) Uani 1 1 d . . . Se4 Se 0.59688(11) 0.21977(11) 0.27611(9) 0.0257(4) Uani 1 1 d . . . C1 C 0.5948(11) 0.4364(9) 0.1403(10) 0.030(3) Uani 1 1 d . . . C2 C 0.6639(11) 0.4292(11) 0.0884(11) 0.038(4) Uani 1 1 d . . . H2 H 0.735 0.4263 0.1129 0.046 Uiso 1 1 calc R . . C3 C 0.6319(12) 0.4260(12) -0.0005(10) 0.040(4) Uani 1 1 d . . . H3 H 0.6809 0.4186 -0.0361 0.047 Uiso 1 1 calc R . . C4 C 0.5293(11) 0.4335(10) -0.0368(10) 0.033(4) Uani 1 1 d . . . H4 H 0.5073 0.4334 -0.0975 0.039 Uiso 1 1 calc R . . C5 C 0.4574(12) 0.4413(13) 0.0169(13) 0.051(5) Uani 1 1 d . . . H5 H 0.3864 0.4453 -0.0079 0.061 Uiso 1 1 calc R . . C6 C 0.4884(11) 0.4433(12) 0.1052(10) 0.038(4) Uani 1 1 d . . . H6 H 0.4398 0.449 0.1414 0.046 Uiso 1 1 calc R . . C7 C 0.8872(10) 0.4159(10) 0.3965(9) 0.029(3) Uani 1 1 d . . . C8 C 0.8992(12) 0.5096(10) 0.4344(12) 0.042(4) Uani 1 1 d . . . H8 H 0.8932 0.5678 0.3992 0.051 Uiso 1 1 calc R . . C9 C 0.9202(13) 0.5201(12) 0.5237(11) 0.043(4) Uani 1 1 d . . . H9 H 0.9292 0.585 0.5489 0.052 Uiso 1 1 calc R . . C10 C 0.9278(12) 0.4343(12) 0.5759(10) 0.042(4) Uani 1 1 d . . . H10 H 0.9434 0.4405 0.6367 0.051 Uiso 1 1 calc R . . C11 C 0.9125(12) 0.3413(11) 0.5381(10) 0.037(4) Uani 1 1 d . . . H11 H 0.9137 0.2833 0.5729 0.044 Uiso 1 1 calc R . . C12 C 0.8949(13) 0.3314(10) 0.4479(10) 0.038(4) Uani 1 1 d . . . H12 H 0.8883 0.2665 0.4225 0.045 Uiso 1 1 calc R . . C13 C 0.8009(11) 0.1819(9) 0.1392(9) 0.024(3) Uani 1 1 d . . . C14 C 0.8821(12) 0.2034(10) 0.1015(10) 0.035(4) Uani 1 1 d . . . H14 H 0.9482 0.2163 0.1352 0.042 Uiso 1 1 calc R . . C15 C 0.8653(14) 0.2059(12) 0.0123(12) 0.047(4) Uani 1 1 d . . . H15 H 0.9212 0.2211 -0.0146 0.056 Uiso 1 1 calc R . . C16 C 0.7708(14) 0.1870(11) -0.0385(11) 0.041(4) Uani 1 1 d . . . H16 H 0.7622 0.1872 -0.0993 0.049 Uiso 1 1 calc R . . C17 C 0.6892(12) 0.1679(13) -0.0003(11) 0.043(4) Uani 1 1 d . . . H17 H 0.6233 0.1569 -0.035 0.052 Uiso 1 1 calc R . . C18 C 0.7012(11) 0.1644(13) 0.0880(11) 0.042(4) Uani 1 1 d . . . H18 H 0.6444 0.1506 0.1142 0.05 Uiso 1 1 calc R . . C19 C 0.6347(10) 0.2119(11) 0.3987(9) 0.028(3) Uani 1 1 d . . . C20 C 0.6284(13) 0.2950(11) 0.4499(10) 0.040(4) Uani 1 1 d . . . H20 H 0.6068 0.3577 0.424 0.047 Uiso 1 1 calc R . . C21 C 0.6535(13) 0.2872(12) 0.5394(13) 0.047(5) Uani 1 1 d . . . H21 H 0.6507 0.3448 0.5741 0.057 Uiso 1 1 calc R . . C22 C 0.6824(12) 0.1958(13) 0.5770(12) 0.041(4) Uani 1 1 d . . . H22 H 0.6991 0.1905 0.6378 0.049 Uiso 1 1 calc R . . C23 C 0.6873(12) 0.1124(12) 0.5277(11) 0.043(4) Uani 1 1 d . . . H23 H 0.7082 0.0501 0.5546 0.052 Uiso 1 1 calc R . . C24 C 0.6625(11) 0.1177(11) 0.4401(10) 0.036(4) Uani 1 1 d . . . H24 H 0.6637 0.0587 0.4066 0.043 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0556(11) 0.0316(8) 0.0251(10) -0.0001(7) 0.0072(8) -0.0074(8) Br2 0.0287(9) 0.0545(10) 0.0291(11) 0.0008(8) 0.0073(7) 0.0049(8) Br3 0.0497(10) 0.0273(8) 0.0345(10) -0.0001(7) 0.0124(8) -0.0037(7) Br4 0.0318(9) 0.0504(10) 0.0307(10) 0.0017(8) 0.0068(8) 0.0063(7) Se1 0.0300(8) 0.0311(8) 0.0162(8) 0.0017(7) 0.0067(7) 0.0013(7) Se2 0.0319(8) 0.0286(8) 0.0174(8) 0.0029(6) 0.0026(6) 0.0007(7) Se3 0.0297(9) 0.0312(8) 0.0179(9) -0.0012(6) 0.0049(7) -0.0007(7) Se4 0.0313(8) 0.0302(8) 0.0160(9) -0.0007(6) 0.0058(7) 0.0000(7) C1 0.050(9) 0.020(6) 0.018(8) 0.004(6) 0.006(7) -0.003(6) C2 0.025(8) 0.058(10) 0.030(10) -0.001(8) 0.002(7) 0.013(7) C3 0.042(10) 0.058(10) 0.022(9) 0.002(8) 0.015(8) 0.007(8) C4 0.039(9) 0.026(7) 0.027(9) -0.008(6) -0.008(7) -0.012(7) C5 0.033(10) 0.059(11) 0.058(14) 0.021(9) 0.003(9) 0.005(8) C6 0.032(8) 0.068(11) 0.015(8) 0.006(8) 0.003(7) 0.010(8) C7 0.030(7) 0.044(8) 0.014(8) -0.005(6) 0.006(6) -0.004(6) C8 0.055(10) 0.018(7) 0.056(13) -0.003(7) 0.017(9) -0.004(7) C9 0.057(11) 0.036(9) 0.033(11) -0.011(8) 0.001(8) 0.015(8) C10 0.055(10) 0.056(10) 0.009(8) 0.005(7) -0.008(7) 0.000(9) C11 0.057(10) 0.038(8) 0.013(9) -0.004(7) -0.001(8) -0.009(8) C12 0.069(11) 0.025(7) 0.016(9) -0.006(6) -0.002(8) -0.010(7) C13 0.043(8) 0.018(6) 0.008(8) -0.007(5) 0.002(6) -0.008(6) C14 0.037(9) 0.037(8) 0.030(10) -0.005(7) 0.004(7) -0.007(7) C15 0.058(11) 0.053(10) 0.037(11) 0.003(8) 0.029(10) -0.004(9) C16 0.070(12) 0.034(9) 0.020(10) 0.007(7) 0.017(9) 0.006(8) C17 0.035(9) 0.064(11) 0.034(11) -0.021(9) 0.013(8) 0.009(8) C18 0.025(8) 0.073(11) 0.030(10) -0.010(9) 0.014(7) -0.006(8) C19 0.027(8) 0.044(9) 0.010(8) -0.001(6) -0.006(6) 0.001(6) C20 0.072(11) 0.030(8) 0.020(9) -0.014(7) 0.020(8) 0.006(8) C21 0.056(11) 0.037(9) 0.051(13) -0.018(9) 0.018(10) -0.009(8) C22 0.035(9) 0.064(12) 0.024(10) -0.002(9) 0.006(8) -0.011(8) C23 0.048(10) 0.045(9) 0.034(11) 0.011(8) 0.001(8) 0.012(8) C24 0.036(9) 0.049(9) 0.024(9) -0.004(7) 0.007(7) 0.012(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 Se1 2.390(2) . ? Br2 Se2 2.391(2) . ? Br3 Se3 2.381(2) . ? Br4 Se4 2.380(2) . ? Se1 C1 1.930(15) . ? Se2 C7 1.901(14) . ? Se3 C13 1.913(14) . ? Se4 C19 1.895(15) . ? C1 C2 1.34(2) . ? C1 C6 1.40(2) . ? C2 C3 1.38(2) . ? C3 C4 1.36(2) . ? C4 C5 1.39(2) . ? C5 C6 1.37(2) . ? C7 C8 1.368(19) . ? C7 C12 1.37(2) . ? C8 C9 1.38(2) . ? C9 C10 1.39(2) . ? C10 C11 1.36(2) . ? C11 C12 1.40(2) . ? C13 C14 1.35(2) . ? C13 C18 1.42(2) . ? C14 C15 1.38(2) . ? C15 C16 1.36(2) . ? C16 C17 1.36(2) . ? C17 C18 1.37(2) . ? C19 C20 1.372(19) . ? C19 C24 1.42(2) . ? C20 C21 1.38(2) . ? C21 C22 1.36(2) . ? C22 C23 1.35(2) . ? C23 C24 1.35(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Se1 Br1 94.9(4) . . ? C7 Se2 Br2 95.6(4) . . ? C13 Se3 Br3 96.2(4) . . ? C19 Se4 Br4 96.1(4) . . ? C2 C1 C6 120.7(14) . . ? C2 C1 Se1 121.8(11) . . ? C6 C1 Se1 117.4(11) . . ? C1 C2 C3 120.7(14) . . ? C4 C3 C2 120.1(15) . . ? C3 C4 C5 119.2(15) . . ? C6 C5 C4 121.1(15) . . ? C5 C6 C1 118.1(15) . . ? C8 C7 C12 119.4(14) . . ? C8 C7 Se2 120.4(12) . . ? C12 C7 Se2 120.2(10) . . ? C7 C8 C9 121.0(15) . . ? C8 C9 C10 119.7(14) . . ? C11 C10 C9 119.2(15) . . ? C10 C11 C12 120.6(14) . . ? C7 C12 C11 120.0(13) . . ? C14 C13 C18 120.6(14) . . ? C14 C13 Se3 119.7(11) . . ? C18 C13 Se3 119.6(11) . . ? C13 C14 C15 118.1(15) . . ? C16 C15 C14 122.4(15) . . ? C17 C16 C15 119.2(16) . . ? C16 C17 C18 121.0(16) . . ? C17 C18 C13 118.6(14) . . ? C20 C19 C24 118.1(14) . . ? C20 C19 Se4 121.3(11) . . ? C24 C19 Se4 120.5(11) . . ? C19 C20 C21 120.5(15) . . ? C22 C21 C20 119.8(15) . . ? C23 C22 C21 120.7(17) . . ? C24 C23 C22 120.8(15) . . ? C23 C24 C19 120.1(14) . . ? data_smg35c _database_code_depnum_ccdc_archive 'CCDC 290835' _audit_creation_date 2002-08-14T00:10:12-00:00 _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 'C24 H38 Br1 P1 Se1' _chemical_formula_sum 'C24 H38 Br P Se' _chemical_formula_weight 516.38 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 c 1' _symmetry_space_group_name_Hall 'C -2yc' _symmetry_Int_Tables_number 9 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 10.1891(4) _cell_length_b 16.3115(6) _cell_length_c 14.8944(6) _cell_angle_alpha 90 _cell_angle_beta 105.165(2) _cell_angle_gamma 90 _cell_volume 2389.24(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8036 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.318 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 1.045 #----------------------------------------------------------------------------# # 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 -0.839001E-1 _diffrn_orient_matrix_ub_12 -0.49431E-2 _diffrn_orient_matrix_ub_13 -0.525596E-1 _diffrn_orient_matrix_ub_21 0.573805E-1 _diffrn_orient_matrix_ub_22 -0.41981E-2 _diffrn_orient_matrix_ub_23 -0.449687E-1 _diffrn_orient_matrix_ub_31 0.28516E-2 _diffrn_orient_matrix_ub_32 -0.609625E-1 _diffrn_orient_matrix_ub_33 0.73584E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_unetI/netI 0.0832 _diffrn_reflns_number 9984 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 4934 _reflns_number_gt 3658 _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^)+(0.0685P)^2^+1.6543P] 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 4934 _refine_ls_number_parameters 244 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0872 _refine_ls_R_factor_gt 0.0536 _refine_ls_wR_factor_ref 0.1329 _refine_ls_wR_factor_gt 0.1175 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.013(14) _refine_diff_density_max 0.798 _refine_diff_density_min -0.642 _refine_diff_density_rms 0.098 #----------------------------------------------------------------------------# # 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' Br Br -0.2901 2.4595 '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 0.0914(5) 0.1475(3) 0.6053(4) 0.0250(12) Uani 1 1 d . . . H1 H 0.0579 0.1384 0.5382 0.03 Uiso 1 1 calc R . . C2 C 0.0267(6) 0.2279(4) 0.6265(5) 0.0358(15) Uani 1 1 d . . . H2A H 0.0579 0.2398 0.6925 0.043 Uiso 1 1 calc R . . H2B H 0.0549 0.2726 0.5928 0.043 Uiso 1 1 calc R . . C3 C -0.1280(7) 0.2213(4) 0.5982(5) 0.0423(17) Uani 1 1 d . . . H3A H -0.1668 0.2713 0.6156 0.051 Uiso 1 1 calc R . . H3B H -0.1596 0.2154 0.5312 0.051 Uiso 1 1 calc R . . C4 C -0.1749(8) 0.1504(6) 0.6436(7) 0.060(2) Uani 1 1 d . . . H4A H -0.273 0.1459 0.6214 0.072 Uiso 1 1 calc R . . H4B H -0.1524 0.1595 0.7103 0.072 Uiso 1 1 calc R . . C5 C -0.1102(7) 0.0705(4) 0.6240(6) 0.0471(18) Uani 1 1 d . . . H5A H -0.1398 0.0262 0.6575 0.057 Uiso 1 1 calc R . . H5B H -0.1409 0.0583 0.558 0.057 Uiso 1 1 calc R . . C6 C 0.0440(6) 0.0749(4) 0.6525(5) 0.0376(15) Uani 1 1 d . . . H6A H 0.0816 0.0247 0.6349 0.045 Uiso 1 1 calc R . . H6B H 0.0759 0.0808 0.7195 0.045 Uiso 1 1 calc R . . C7 C 0.3372(6) 0.0536(4) 0.6019(5) 0.0299(14) Uani 1 1 d . . . H7 H 0.3081 0.0137 0.6419 0.036 Uiso 1 1 calc R . . C8 C 0.2659(7) 0.0300(4) 0.5026(5) 0.0391(16) Uani 1 1 d . . . H8A H 0.2905 0.0683 0.4599 0.047 Uiso 1 1 calc R . . H8B H 0.1682 0.0328 0.4936 0.047 Uiso 1 1 calc R . . C9 C 0.3064(8) -0.0577(5) 0.4817(6) 0.0488(19) Uani 1 1 d . . . H9A H 0.2749 -0.0965 0.5209 0.059 Uiso 1 1 calc R . . H9B H 0.2633 -0.0713 0.4173 0.059 Uiso 1 1 calc R . . C10 C 0.4588(7) -0.0645(4) 0.4993(5) 0.0427(17) Uani 1 1 d . . . H10A H 0.49 -0.0277 0.4581 0.051 Uiso 1 1 calc R . . H10B H 0.483 -0.12 0.4868 0.051 Uiso 1 1 calc R . . C11 C 0.5273(7) -0.0423(5) 0.6008(6) 0.0460(18) Uani 1 1 d . . . H11A H 0.4981 -0.0801 0.642 0.055 Uiso 1 1 calc R . . H11B H 0.6252 -0.0469 0.6122 0.055 Uiso 1 1 calc R . . C12 C 0.4903(7) 0.0440(5) 0.6207(7) 0.053(2) Uani 1 1 d . . . H12A H 0.5242 0.082 0.582 0.063 Uiso 1 1 calc R . . H12B H 0.533 0.0573 0.6852 0.063 Uiso 1 1 calc R . . C13 C 0.3204(6) 0.2437(4) 0.5716(4) 0.0279(13) Uani 1 1 d . . . H13 H 0.2938 0.2912 0.6031 0.034 Uiso 1 1 calc R . . C14 C 0.2402(7) 0.2512(4) 0.4693(4) 0.0346(15) Uani 1 1 d . . . H14A H 0.2633 0.2058 0.4341 0.042 Uiso 1 1 calc R . . H14B H 0.1435 0.2483 0.4646 0.042 Uiso 1 1 calc R . . C15 C 0.2725(7) 0.3322(4) 0.4279(5) 0.0409(16) Uani 1 1 d . . . H15A H 0.2397 0.3774 0.4584 0.049 Uiso 1 1 calc R . . H15B H 0.2255 0.3341 0.3623 0.049 Uiso 1 1 calc R . . C16 C 0.4263(7) 0.3423(5) 0.4396(7) 0.056(2) Uani 1 1 d . . . H16A H 0.4442 0.3954 0.416 0.068 Uiso 1 1 calc R . . H16B H 0.4581 0.3003 0.4043 0.068 Uiso 1 1 calc R . . C17 C 0.5035(7) 0.3351(5) 0.5442(7) 0.062(2) Uani 1 1 d . . . H17A H 0.6005 0.3404 0.5514 0.075 Uiso 1 1 calc R . . H17B H 0.4753 0.379 0.579 0.075 Uiso 1 1 calc R . . C18 C 0.4736(6) 0.2537(5) 0.5817(5) 0.0442(18) Uani 1 1 d . . . H18A H 0.5225 0.2495 0.6468 0.053 Uiso 1 1 calc R . . H18B H 0.5048 0.21 0.5482 0.053 Uiso 1 1 calc R . . C19 C 0.3447(7) 0.2812(4) 0.8056(4) 0.0424(18) Uani 1 1 d . . . C20 C 0.2275(7) 0.3043(5) 0.8303(5) 0.0517(19) Uani 1 1 d . . . H20 H 0.1637 0.2648 0.8347 0.062 Uiso 1 1 calc R . . C21 C 0.2054(9) 0.3843(6) 0.8481(6) 0.065(3) Uani 1 1 d . . . H21 H 0.1272 0.3998 0.8649 0.078 Uiso 1 1 calc R . . C22 C 0.3017(11) 0.4424(6) 0.8407(7) 0.075(3) Uani 1 1 d . . . H22 H 0.285 0.4977 0.8484 0.09 Uiso 1 1 calc R . . C23 C 0.4194(10) 0.4194(5) 0.8225(5) 0.064(2) Uani 1 1 d . . . H23 H 0.4862 0.4586 0.824 0.077 Uiso 1 1 calc R . . C24 C 0.4440(8) 0.3367(4) 0.8009(5) 0.0465(18) Uani 1 1 d . . . H24 H 0.5226 0.3213 0.7846 0.056 Uiso 1 1 calc R . . P1 P 0.27736(14) 0.15426(9) 0.63074(10) 0.0241(3) Uani 1 1 d . . . Se1 Se 0.37372(5) 0.16558(4) 0.78265(4) 0.0401(2) Uani 1 1 d . . . Br1 Br 0.30298(9) -0.11083(5) 0.77171(6) 0.0592(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.020(3) 0.023(3) 0.033(3) 0.004(2) 0.007(2) 0.002(2) C2 0.035(3) 0.029(3) 0.044(4) -0.008(3) 0.012(3) 0.006(3) C3 0.032(3) 0.037(4) 0.054(4) -0.004(3) 0.005(3) 0.003(3) C4 0.029(4) 0.076(6) 0.076(6) 0.016(5) 0.017(4) 0.014(4) C5 0.029(3) 0.046(4) 0.068(5) 0.018(4) 0.016(3) -0.003(3) C6 0.031(3) 0.030(3) 0.054(4) 0.016(3) 0.015(3) 0.003(3) C7 0.025(3) 0.019(3) 0.046(4) 0.006(3) 0.011(3) 0.003(2) C8 0.040(4) 0.036(4) 0.040(4) -0.003(3) 0.008(3) 0.013(3) C9 0.052(4) 0.041(4) 0.051(4) -0.010(3) 0.009(4) 0.016(4) C10 0.049(4) 0.030(4) 0.057(4) 0.006(3) 0.028(4) 0.013(3) C11 0.031(3) 0.037(4) 0.069(5) -0.004(4) 0.011(3) 0.013(3) C12 0.027(3) 0.040(4) 0.089(6) -0.007(4) 0.010(4) 0.004(3) C13 0.028(3) 0.026(3) 0.029(3) 0.011(2) 0.006(3) 0.003(2) C14 0.035(3) 0.033(4) 0.035(3) 0.006(3) 0.008(3) -0.009(3) C15 0.033(3) 0.043(4) 0.043(4) 0.017(3) 0.003(3) 0.004(3) C16 0.035(4) 0.063(5) 0.079(6) 0.041(4) 0.028(4) 0.006(4) C17 0.023(3) 0.060(5) 0.099(7) 0.037(5) 0.008(4) -0.004(3) C18 0.026(3) 0.052(4) 0.054(4) 0.021(3) 0.009(3) 0.007(3) C19 0.056(5) 0.047(4) 0.019(3) -0.001(3) 0.000(3) -0.006(3) C20 0.043(4) 0.075(6) 0.037(4) -0.017(4) 0.009(3) -0.006(4) C21 0.059(5) 0.086(7) 0.045(4) -0.028(4) 0.005(4) 0.015(5) C22 0.088(7) 0.050(5) 0.073(6) -0.026(5) -0.003(5) 0.007(5) C23 0.081(6) 0.051(5) 0.043(4) -0.006(4) -0.015(4) -0.006(5) C24 0.043(4) 0.053(5) 0.033(4) 0.006(3) -0.008(3) -0.009(4) P1 0.0217(7) 0.0209(8) 0.0293(8) 0.0020(6) 0.0062(6) 0.0008(6) Se1 0.0490(4) 0.0342(3) 0.0309(3) 0.0068(3) -0.0004(3) -0.0030(3) Br1 0.0710(5) 0.0616(5) 0.0511(4) 0.0082(4) 0.0269(4) 0.0020(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 1.519(8) . ? C1 C2 1.537(8) . ? C1 P1 1.835(6) . ? C2 C3 1.525(9) . ? C3 C4 1.481(11) . ? C4 C5 1.523(11) . ? C5 C6 1.518(9) . ? C7 C8 1.516(9) . ? C7 C12 1.518(9) . ? C7 P1 1.841(6) . ? C8 C9 1.543(9) . ? C9 C10 1.509(10) . ? C10 C11 1.533(10) . ? C11 C12 1.507(10) . ? C13 C14 1.534(8) . ? C13 C18 1.537(9) . ? C13 P1 1.817(6) . ? C14 C15 1.530(9) . ? C15 C16 1.539(10) . ? C16 C17 1.555(13) . ? C17 C18 1.502(10) . ? C19 C24 1.374(10) . ? C19 C20 1.389(10) . ? C19 Se1 1.953(7) . ? C20 C21 1.363(12) . ? C21 C22 1.389(14) . ? C22 C23 1.350(14) . ? C23 C24 1.423(11) . ? P1 Se1 2.2260(15) . ? 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 111.4(5) . . ? C6 C1 P1 112.8(4) . . ? C2 C1 P1 112.4(4) . . ? C3 C2 C1 110.6(5) . . ? C4 C3 C2 111.3(6) . . ? C3 C4 C5 111.9(6) . . ? C6 C5 C4 111.9(6) . . ? C5 C6 C1 109.8(5) . . ? C8 C7 C12 111.2(6) . . ? C8 C7 P1 110.5(4) . . ? C12 C7 P1 115.8(5) . . ? C7 C8 C9 110.3(5) . . ? C10 C9 C8 110.5(6) . . ? C9 C10 C11 109.7(6) . . ? C12 C11 C10 110.0(6) . . ? C11 C12 C7 110.9(6) . . ? C14 C13 C18 110.6(5) . . ? C14 C13 P1 114.3(4) . . ? C18 C13 P1 113.9(4) . . ? C15 C14 C13 110.7(5) . . ? C14 C15 C16 111.5(5) . . ? C15 C16 C17 109.8(6) . . ? C18 C17 C16 109.9(7) . . ? C17 C18 C13 110.9(5) . . ? C24 C19 C20 122.0(7) . . ? C24 C19 Se1 118.7(6) . . ? C20 C19 Se1 119.2(6) . . ? C21 C20 C19 120.6(8) . . ? C20 C21 C22 118.8(8) . . ? C23 C22 C21 120.7(8) . . ? C22 C23 C24 121.8(9) . . ? C19 C24 C23 115.9(8) . . ? C13 P1 C1 108.4(3) . . ? C13 P1 C7 117.8(3) . . ? C1 P1 C7 106.6(3) . . ? C13 P1 Se1 109.2(2) . . ? C1 P1 Se1 111.8(2) . . ? C7 P1 Se1 103.1(2) . . ? C19 Se1 P1 102.21(17) . . ? # Attachment 'ph3psephbr.cif' # CIF produced by WinGX routine CIF_UPDATE # Created on 2002-08-30 at 13:33:55 # 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 : new dreduc sortav struct data_new _database_code_depnum_ccdc_archive 'CCDC 290836' _audit_creation_date 2002-08-30T13:33:55-00:00 _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 'C24 H20 Br1 P1 Se1' _chemical_formula_sum 'C24 H20 Br P Se' _chemical_formula_weight 498.24 _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 14.0231(7) _cell_length_b 16.7384(8) _cell_length_c 18.1228(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4253.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 89312 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 26.373 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.556 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1984 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.725 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.718 _exptl_absorpt_correction_T_max 1.168 #----------------------------------------------------------------------------# # 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 -0.509437E-1 _diffrn_orient_matrix_ub_12 0.372509E-1 _diffrn_orient_matrix_ub_13 0.502E-4 _diffrn_orient_matrix_ub_21 -0.278365E-1 _diffrn_orient_matrix_ub_22 -0.543135E-1 _diffrn_orient_matrix_ub_23 0.248397E-1 _diffrn_orient_matrix_ub_31 0.141094E-1 _diffrn_orient_matrix_ub_32 0.273434E-1 _diffrn_orient_matrix_ub_33 0.492719E-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 0.0961 _diffrn_reflns_av_unetI/netI 0.0634 _diffrn_reflns_number 20089 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 26.34 _diffrn_reflns_theta_full 26.34 _diffrn_measured_fraction_theta_full 0.978 _diffrn_measured_fraction_theta_max 0.978 _reflns_number_total 4248 _reflns_number_gt 3168 _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^)+(0.0322P)^2^+11.3902P] 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 0.00013(19) _refine_ls_number_reflns 4248 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0805 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1174 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.781 _refine_diff_density_min -0.746 _refine_diff_density_rms 0.106 #----------------------------------------------------------------------------# # 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' Br Br -0.2901 2.4595 '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 0.5676(3) 0.4738(3) -0.2167(2) 0.0284(10) Uani 1 1 d . . . C2 C 0.5353(4) 0.5381(3) -0.1757(3) 0.0364(12) Uani 1 1 d . . . C3 C 0.5569(4) 0.5429(4) -0.1012(3) 0.0421(14) Uani 1 1 d . . . C4 C 0.6101(4) 0.4837(4) -0.0677(3) 0.0399(13) Uani 1 1 d . . . C5 C 0.6436(4) 0.4204(4) -0.1081(3) 0.0408(13) Uani 1 1 d . . . C6 C 0.6226(4) 0.4148(3) -0.1830(3) 0.0377(12) Uani 1 1 d . . . C7 C 0.4614(4) 0.3769(3) -0.3211(3) 0.0335(11) Uani 1 1 d . . . C8 C 0.4094(4) 0.3504(3) -0.2603(3) 0.0377(12) Uani 1 1 d . . . C9 C 0.3502(4) 0.2850(4) -0.2676(3) 0.0464(14) Uani 1 1 d . . . C10 C 0.3426(5) 0.2451(4) -0.3331(4) 0.0520(16) Uani 1 1 d . . . C11 C 0.3933(5) 0.2707(4) -0.3947(3) 0.0510(16) Uani 1 1 d . . . C12 C 0.4529(4) 0.3368(4) -0.3888(3) 0.0437(14) Uani 1 1 d . . . C13 C 0.4813(3) 0.5477(3) -0.3495(3) 0.0321(11) Uani 1 1 d . . . C14 C 0.3929(4) 0.5403(4) -0.3856(3) 0.0344(12) Uani 1 1 d . . . C15 C 0.3503(4) 0.6048(4) -0.4178(3) 0.0436(14) Uani 1 1 d . . . C16 C 0.3956(4) 0.6787(4) -0.4158(3) 0.0448(14) Uani 1 1 d . . . C17 C 0.4815(4) 0.6884(4) -0.3795(3) 0.0427(13) Uani 1 1 d . . . C18 C 0.5246(4) 0.6222(3) -0.3460(3) 0.0388(12) Uani 1 1 d . . . C19 C 0.7310(4) 0.5247(3) -0.3667(3) 0.0380(12) Uani 1 1 d . . . C20 C 0.7744(4) 0.5481(4) -0.3013(3) 0.0402(13) Uani 1 1 d . . . C21 C 0.8128(4) 0.6239(4) -0.2972(4) 0.0477(15) Uani 1 1 d . . . C22 C 0.8092(4) 0.6752(4) -0.3567(4) 0.0551(17) Uani 1 1 d . . . H22 H 0.8352 0.7262 -0.3536 0.066 Uiso 1 1 calc R . . C23 C 0.7662(5) 0.6493(4) -0.4210(3) 0.0508(16) Uani 1 1 d . . . C24 C 0.7253(4) 0.5763(4) -0.4265(3) 0.0443(14) Uani 1 1 d . . . P1 P 0.53934(9) 0.46078(8) -0.31264(7) 0.0301(3) Uani 1 1 d . . . Se1 Se 0.67132(4) 0.42120(3) -0.37418(3) 0.03421(17) Uani 1 1 d . . . Br1 Br 0.85241(4) 0.35478(3) -0.43775(3) 0.03704(18) Uani 1 1 d . . . H2 H 0.496(4) 0.572(3) -0.195(3) 0.022(12) Uiso 1 1 d . . . H3 H 0.538(4) 0.587(4) -0.074(3) 0.053(18) Uiso 1 1 d . . . H4 H 0.627(4) 0.493(3) -0.016(3) 0.034(13) Uiso 1 1 d . . . H5 H 0.680(4) 0.379(3) -0.086(3) 0.047(16) Uiso 1 1 d . . . H6 H 0.652(3) 0.368(3) -0.210(3) 0.028(13) Uiso 1 1 d . . . H8 H 0.414(4) 0.377(4) -0.213(3) 0.059(19) Uiso 1 1 d . . . H9 H 0.315(4) 0.261(4) -0.217(3) 0.061(18) Uiso 1 1 d . . . H10 H 0.303(5) 0.204(4) -0.339(3) 0.053(18) Uiso 1 1 d . . . H11 H 0.387(5) 0.247(4) -0.443(4) 0.07(2) Uiso 1 1 d . . . H12 H 0.492(3) 0.355(3) -0.427(2) 0.021(12) Uiso 1 1 d . . . H14 H 0.369(3) 0.494(3) -0.387(2) 0.021(13) Uiso 1 1 d . . . H15 H 0.291(5) 0.597(4) -0.441(3) 0.056(18) Uiso 1 1 d . . . H16 H 0.366(4) 0.724(3) -0.435(3) 0.036(14) Uiso 1 1 d . . . H17 H 0.514(5) 0.734(4) -0.378(4) 0.07(2) Uiso 1 1 d . . . H18 H 0.580(4) 0.629(3) -0.319(3) 0.031(13) Uiso 1 1 d . . . H20 H 0.779(4) 0.508(3) -0.257(3) 0.054(17) Uiso 1 1 d . . . H21 H 0.843(4) 0.642(3) -0.256(3) 0.045(16) Uiso 1 1 d . . . H23 H 0.764(4) 0.685(4) -0.455(3) 0.048(17) Uiso 1 1 d . . . H24 H 0.692(4) 0.555(3) -0.474(3) 0.037(14) 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 0.025(2) 0.035(3) 0.025(2) -0.001(2) -0.0002(19) -0.004(2) C2 0.033(3) 0.040(3) 0.036(3) -0.001(2) -0.003(2) 0.007(3) C3 0.049(3) 0.050(4) 0.027(3) -0.012(3) -0.002(2) 0.004(3) C4 0.041(3) 0.056(4) 0.024(2) -0.002(2) -0.007(2) -0.005(3) C5 0.048(3) 0.043(3) 0.031(3) 0.002(2) -0.009(2) 0.002(3) C6 0.039(3) 0.042(3) 0.032(3) -0.005(2) -0.002(2) 0.005(3) C7 0.034(3) 0.040(3) 0.027(2) -0.001(2) -0.002(2) -0.001(2) C8 0.032(3) 0.044(3) 0.038(3) 0.000(3) -0.005(2) -0.001(2) C9 0.045(3) 0.047(3) 0.047(3) 0.005(3) -0.003(3) -0.001(3) C10 0.047(4) 0.041(3) 0.069(4) -0.003(3) -0.009(3) -0.012(3) C11 0.054(4) 0.051(4) 0.048(3) -0.018(3) -0.015(3) -0.003(3) C12 0.042(3) 0.057(4) 0.033(3) -0.007(3) -0.002(2) 0.002(3) C13 0.028(3) 0.044(3) 0.024(2) 0.000(2) 0.001(2) 0.003(2) C14 0.038(3) 0.038(3) 0.028(2) -0.006(2) -0.001(2) -0.002(3) C15 0.042(3) 0.060(4) 0.028(3) -0.004(3) -0.005(2) 0.008(3) C16 0.048(3) 0.051(4) 0.036(3) 0.009(3) 0.001(3) 0.012(3) C17 0.045(3) 0.040(3) 0.043(3) 0.007(3) 0.011(3) -0.002(3) C18 0.030(3) 0.047(3) 0.040(3) 0.000(3) 0.006(2) -0.005(3) C19 0.027(3) 0.048(3) 0.039(3) -0.001(2) 0.009(2) 0.006(2) C20 0.029(3) 0.049(3) 0.042(3) 0.000(3) 0.000(2) 0.007(3) C21 0.036(3) 0.050(4) 0.057(4) -0.009(3) 0.000(3) 0.003(3) C22 0.044(3) 0.036(3) 0.085(5) -0.005(3) 0.023(3) 0.002(3) C23 0.056(4) 0.055(4) 0.041(3) 0.006(3) 0.022(3) -0.003(3) C24 0.053(4) 0.044(3) 0.036(3) 0.004(3) 0.015(3) 0.005(3) P1 0.0289(7) 0.0391(8) 0.0223(6) -0.0029(5) -0.0003(5) -0.0009(6) Se1 0.0348(3) 0.0420(3) 0.0258(3) -0.0023(2) 0.0041(2) 0.0009(2) Br1 0.0400(3) 0.0449(3) 0.0262(3) 0.0013(2) 0.0038(2) 0.0075(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 C2 1.384(7) . ? C1 C6 1.395(7) . ? C1 P1 1.796(5) . ? C2 C3 1.386(7) . ? C3 C4 1.381(8) . ? C4 C5 1.371(8) . ? C5 C6 1.392(7) . ? C7 C8 1.394(7) . ? C7 C12 1.404(7) . ? C7 P1 1.786(5) . ? C8 C9 1.380(8) . ? C9 C10 1.367(8) . ? C10 C11 1.391(9) . ? C11 C12 1.391(9) . ? C13 C18 1.388(8) . ? C13 C14 1.408(7) . ? C13 P1 1.796(5) . ? C14 C15 1.364(8) . ? C15 C16 1.391(9) . ? C16 C17 1.382(8) . ? C17 C18 1.402(8) . ? C19 C20 1.388(7) . ? C19 C24 1.389(7) . ? C19 Se1 1.929(6) . ? C20 C21 1.380(8) . ? C21 C22 1.380(9) . ? C22 C23 1.381(9) . ? C23 C24 1.353(9) . ? P1 Se1 2.2601(14) . ? 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 119.8(5) . . ? C2 C1 P1 122.8(4) . . ? C6 C1 P1 117.4(4) . . ? C1 C2 C3 119.8(5) . . ? C4 C3 C2 120.3(5) . . ? C5 C4 C3 120.3(5) . . ? C4 C5 C6 120.1(5) . . ? C5 C6 C1 119.7(5) . . ? C8 C7 C12 119.6(5) . . ? C8 C7 P1 120.2(4) . . ? C12 C7 P1 120.2(4) . . ? C9 C8 C7 119.4(5) . . ? C10 C9 C8 121.2(6) . . ? C9 C10 C11 120.5(6) . . ? C12 C11 C10 119.3(5) . . ? C11 C12 C7 119.9(6) . . ? C18 C13 C14 119.1(5) . . ? C18 C13 P1 120.8(4) . . ? C14 C13 P1 120.0(4) . . ? C15 C14 C13 121.0(6) . . ? C14 C15 C16 119.5(6) . . ? C17 C16 C15 121.0(6) . . ? C16 C17 C18 119.3(6) . . ? C13 C18 C17 120.1(5) . . ? C20 C19 C24 121.1(5) . . ? C20 C19 Se1 120.3(4) . . ? C24 C19 Se1 118.6(4) . . ? C21 C20 C19 118.5(6) . . ? C20 C21 C22 121.0(6) . . ? C21 C22 C23 118.7(6) . . ? C24 C23 C22 122.1(6) . . ? C23 C24 C19 118.6(6) . . ? C7 P1 C13 109.2(2) . . ? C7 P1 C1 108.3(2) . . ? C13 P1 C1 111.2(2) . . ? C7 P1 Se1 103.19(17) . . ? C13 P1 Se1 115.17(16) . . ? C1 P1 Se1 109.42(16) . . ? C19 Se1 P1 93.27(15) . . ?