# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- Compound2.cif' #------------------ AUDIT DETAILS -------------------------------------------# _audit_creation_date 2012-04-26 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _audit_update_record ? #------------------ AUTHOR DETAILS -------------------------------------------# # Name and address of author for correspondence _publ_contact_author_name N.Barnes _publ_contact_author_address ; Department of Chemistry University of Anywhere Sometown Somewhere, UK ; _publ_contact_author_email nick_barnes28@hotmail.com _publ_contact_author_fax 00(000)0000000 _publ_contact_author_phone 00(000)0000000 # Insert blank lines between references _publ_section_references ; Blessing, R. H. (1995) Acta Cryst., A51, 33-38. Blessing, R. H. (1987) Cryst. Rev. 1, 3-58. Blessing, R. H. (1989) J. Appl. Cryst. 22, 396-397. Bruker (2007) APEX2 (Version 2.1-4), SAINT (version 7.34A), SADABS (version 2007/4), BrukerAXS Inc, Madison, Wisconsin, USA. Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358. Flack H. D. & Bernardinelli, G. (71999). Acta Cryst. A55, 908-915. Flack H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148. Lehman, M. S. and Larsen, F. K. (1974) Acta. Cryst. A30, 580 LePage, Y. (1987). J. Appl. Cryst. 20, 264-269. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968) Acta Cryst, A24, 351-359 Streltsov, V. A. & Zavodnik, V. E. (1989) Sov. Phys. Crystallogr. 34, 824-828 Streltsov, V. A. & Zavodnik, V. E. (1990) Sov. Phys. Crystallogr. 35, 281. ABSCOR: Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. APEX, APEX2, SMART, SAINT, SAINT-Plus: Bruker (2007). Program name(s). Bruker AXS Inc., Madison, Wisconsin, USA. [Older versions (pre-1997) should refer to Siemens Analytical X-ray Instruments Inc. instead of Bruker AXS.] CAD-4 Software: Enraf-Nonius (1989). CAD-4 Software (or CAD-4 EXPRESS). Enraf-Nonius, Delft, The Netherlands. Cambridge Structural Database: Allen, F. R. (2002). Acta Cryst. B58, 380-388. CAMERON: Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, Oxford, England. CrysAlis CCD, CrysAlis RED and associated programs: Oxford Diffraction (2006). Program name(s). Oxford Diffraction Ltd, Abingdon, England. CRYSTALS: Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. COLLECT: Nonius [or Hooft, R. W. W.] (1998). COLLECT. Nonius BV, Delft, The Netherlands. DENZO/SCALEPACK: Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press. DIAMOND: Brandenburg, K. [or Brandenburg, K. & Putz, H., or Brandenburg, K. & Berndt, M.] (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. DIF4 and REDU4: Stoe & Cie (1991). Program name(s). Stoe & Cie, Darmstadt, Germany. DIFABS: Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158 - 166. DIRAX: Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92-96. DIRDIF99: Beurskens, P.T., Beurskens, G., de Gelder, R., Garci\'ia-Granda, S., Gould, R.O., Israel, R. & Smits, J.M.M. (1999) The DIRDIF-99 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. enCIFer: Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338. EVALCCD: Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220-229. JANA2000: Petricek, V. & Dusek, M. (2000). JANA2000. Institute of Physics, Czech Academy of Sciences, Prague, Czech Republic. Mercury: Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457. Mogul: Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E. & Orpen, A. G. (2004). J. Chem. Inf. Comput. Sci. 44, 2133-2144. ORTEPII: Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. ORTEPIII: Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. ORTEP-3: Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. PARST: Nardelli, M. (1995). J. Appl. Cryst. 28, 659. PLATON: Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13. PROCESS: Rigaku (1996). PROCESS. Rigaku Corporation, Tokyo, Japan. PROCESS-AUTO: Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. publCIF: Westrip, S. P. (2008). publCIF. In preparation. SADABS, TWINABS: Bruker (2001). Program name. Bruker AXS Inc., Madison, Wisconsin, USA. or Sheldrick, G. M. (1996). Program name. University of G ttingen, Germany. SHELX Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. SIR92: Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. SIR97: Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. SIR2002: Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. SUPERFLIP Palatinus, L. & Chapuis, G. (2007) J. Appl. Cryst. 40, 786-790. TEXSAN: Molecular Structure Corporation & Rigaku (2000). TEXSAN. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. WinGX: Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. X-AREA, X-RED, X-RED32, X-SHAPE: Stoe & Cie (2002). Program name(s). Stoe & Cie GmbH, Darmstadt, Germany. XCAD4: Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. XSCANS: Siemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. ; _publ_requested_category FO loop_ _publ_author_name N.Barnes A.Brisdon #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_rob2 _database_code_depnum_ccdc_archive 'CCDC 881801' #TrackingRef '- Compound2.cif' _audit_creation_date 2012-04-26T23:58:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H12 As1 Br3 F3 P1 Se1' _chemical_formula_sum 'C18 H12 As Br3 F3 P Se' _chemical_formula_weight 709.83 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting cubic _symmetry_space_group_name_H-M 'I 2 3' _symmetry_space_group_name_Hall 'I 2 2 3' _symmetry_Int_Tables_number 197 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x, -y, -z' '-x, y, -z' 'y, z, x' '-y, -z, x' 'y, -z, -x' '-y, z, -x' 'z, x, y' '-z, x, -y' '-z, -x, y' 'z, -x, -y' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' 'y+1/2, z+1/2, x+1/2' '-y+1/2, -z+1/2, x+1/2' 'y+1/2, -z+1/2, -x+1/2' '-y+1/2, z+1/2, -x+1/2' 'z+1/2, x+1/2, y+1/2' '-z+1/2, x+1/2, -y+1/2' '-z+1/2, -x+1/2, y+1/2' 'z+1/2, -x+1/2, -y+1/2' _cell_length_a 16.2032(18) _cell_length_b 16.2032(18) _cell_length_c 16.2032(18) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4254.0(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 342 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 2.217 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2672 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 9.047 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.57 _exptl_absorpt_correction_T_max 0.6605 _exptl_absorpt_process_details ; Blessing, R. H. (1995) Acta Cryst., A51, 33-38. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(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 0.520324E-1 _diffrn_orient_matrix_ub_12 0.171235E-1 _diffrn_orient_matrix_ub_13 0.284313E-1 _diffrn_orient_matrix_ub_21 0.247299E-1 _diffrn_orient_matrix_ub_22 0.152581E-1 _diffrn_orient_matrix_ub_23 -0.544474E-1 _diffrn_orient_matrix_ub_31 -0.22136E-1 _diffrn_orient_matrix_ub_32 0.572963E-1 _diffrn_orient_matrix_ub_33 0.60025E-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 0.105 _diffrn_reflns_av_unetI/netI 0.0995 _diffrn_reflns_number 1670 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 26.36 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.746 _diffrn_measured_fraction_theta_max 0.746 _reflns_number_total 1011 # 401 Friedel pairs _reflns_number_gt 792 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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 following ISOR restraint was used to prevent the lighter atom adp's going npd "isor 0.01 0.02 C1 > C6" ; _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^+157.9333P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1011 _refine_ls_number_parameters 83 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0907 _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.16 _refine_ls_wR_factor_gt 0.1376 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0 _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 0.03(7) _refine_diff_density_max 0.744 _refine_diff_density_min -0.673 _refine_diff_density_rms 0.156 #----------------------------------------------------------------------------# # 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' As As 0.0499 2.0058 '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' F F 0.0171 0.0103 '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 C1 C 1.2724(9) 0.1555(10) 0.1386(9) 0.020(3) Uani 1 1 d U . . C2 C 1.3049(12) 0.0743(12) 0.1240(13) 0.040(5) Uani 1 1 d U . . H2 H 1.2704 0.0269 0.1253 0.048 Uiso 1 1 calc R . . C3 C 1.3886(10) 0.0683(11) 0.1080(10) 0.030(4) Uani 1 1 d U . . H3 H 1.4124 0.0153 0.0998 0.036 Uiso 1 1 calc R . . C4 C 1.4367(10) 0.1354(11) 0.1036(10) 0.032(4) Uani 1 1 d U . . C5 C 1.4067(12) 0.2151(12) 0.1167(12) 0.041(5) Uani 1 1 d U . . H5 H 1.4422 0.2617 0.1132 0.049 Uiso 1 1 calc R . . C6 C 1.3200(12) 0.2248(12) 0.1359(12) 0.038(4) Uani 1 1 d U . . H6 H 1.297 0.2777 0.1462 0.046 Uiso 1 1 calc R . . F1 F 1.5190(7) 0.1273(7) 0.0874(7) 0.048(3) Uani 1 1 d . . . As1 As 0.88348(11) 0.11652(11) 0.11652(11) 0.0317(8) Uani 1 3 d S . . Br1 Br 0.85637(11) 0.07907(11) 0.25585(11) 0.0342(5) Uani 1 1 d . . . P1 P 1.1643(3) 0.1643(3) 0.1643(3) 0.0282(18) Uani 1 3 d S . . Se1 Se 1.08751(10) 0.08751(10) 0.08751(10) 0.0289(7) Uani 1 3 d S . . 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 0.021(6) 0.025(7) 0.016(6) 0.007(5) 0.009(5) -0.003(5) C2 0.039(8) 0.033(8) 0.047(8) 0.000(7) 0.003(7) -0.003(6) C3 0.031(7) 0.030(7) 0.030(7) 0.003(6) -0.002(6) -0.003(6) C4 0.030(8) 0.034(7) 0.031(8) -0.001(6) 0.007(6) 0.012(6) C5 0.042(8) 0.030(7) 0.051(8) -0.003(7) -0.003(7) 0.004(7) C6 0.041(8) 0.033(8) 0.041(8) -0.007(6) -0.004(7) -0.001(6) F1 0.033(6) 0.049(7) 0.062(7) -0.005(6) 0.003(5) -0.002(5) As1 0.0317(8) 0.0317(8) 0.0317(8) -0.0007(8) 0.0007(8) 0.0007(8) Br1 0.0426(11) 0.0298(10) 0.0302(10) -0.0006(8) -0.0008(8) 0.0011(8) P1 0.0282(18) 0.0282(18) 0.0282(18) -0.0025(19) -0.0025(19) -0.0025(19) Se1 0.0289(7) 0.0289(7) 0.0289(7) -0.0012(7) -0.0012(7) -0.0012(7) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.44(2) . ? C1 P1 1.806(15) . ? C2 C3 1.38(3) . ? C2 H2 0.95 . ? C3 C4 1.34(2) . ? C3 H3 0.95 . ? C4 F1 1.366(19) . ? C4 C5 1.40(3) . ? C5 C6 1.45(3) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? As1 Br1 2.379(2) 8_656 ? As1 Br1 2.379(2) 11_665 ? As1 Br1 2.379(2) . ? P1 C1 1.806(15) 9_645 ? P1 C1 1.806(15) 5_654 ? P1 Se1 2.155(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 C6 C1 C2 122.8(16) . . ? C6 C1 P1 119.4(13) . . ? C2 C1 P1 117.8(13) . . ? C3 C2 C1 117.0(17) . . ? C3 C2 H2 121.5 . . ? C1 C2 H2 121.5 . . ? C4 C3 C2 121.5(18) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 F1 120.0(15) . . ? C3 C4 C5 122.7(17) . . ? F1 C4 C5 117.3(16) . . ? C4 C5 C6 118.0(18) . . ? C4 C5 H5 121 . . ? C6 C5 H5 121 . . ? C1 C6 C5 117.9(17) . . ? C1 C6 H6 121.1 . . ? C5 C6 H6 121.1 . . ? Br1 As1 Br1 96.54(10) 8_656 11_665 ? Br1 As1 Br1 96.54(10) 8_656 . ? Br1 As1 Br1 96.54(10) 11_665 . ? C1 P1 C1 106.4(6) 9_645 5_654 ? C1 P1 C1 106.4(6) 9_645 . ? C1 P1 C1 106.4(6) 5_654 . ? C1 P1 Se1 112.4(6) 9_645 . ? C1 P1 Se1 112.4(6) 5_654 . ? C1 P1 Se1 112.4(6) . . ? 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 1(3) . . . . ? P1 C1 C2 C3 -177.3(14) . . . . ? C1 C2 C3 C4 -2(3) . . . . ? C2 C3 C4 F1 -179.7(17) . . . . ? C2 C3 C4 C5 2(3) . . . . ? C3 C4 C5 C6 0(3) . . . . ? F1 C4 C5 C6 -178.7(16) . . . . ? C2 C1 C6 C5 0(3) . . . . ? P1 C1 C6 C5 178.8(14) . . . . ? C4 C5 C6 C1 -1(3) . . . . ? C6 C1 P1 C1 14.3(18) . . . 9_645 ? C2 C1 P1 C1 -167.3(13) . . . 9_645 ? C6 C1 P1 C1 -98.8(11) . . . 5_654 ? C2 C1 P1 C1 79.6(19) . . . 5_654 ? C6 C1 P1 Se1 137.7(13) . . . . ? C2 C1 P1 Se1 -43.8(15) . . . . ? # END of CIF # Attachment '- Compound3.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2012-05-02 at 17:17:27 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : rob dreduc sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_rob3 _database_code_depnum_ccdc_archive 'CCDC 881802' #TrackingRef '- Compound3.cif' _audit_creation_date 2012-05-02T17:17:27-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H12 Cl3 F3 P1 Sb1 Se1' _chemical_formula_sum 'C18 H12 Cl3 F3 P Sb Se' _chemical_formula_weight 623.31 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting cubic _symmetry_space_group_name_H-M 'I 2 3' _symmetry_space_group_name_Hall 'I 2 2 3' _symmetry_Int_Tables_number 197 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x, -y, -z' '-x, y, -z' 'z, x, y' 'y, z, x' '-z, -x, y' '-y, z, -x' 'z, -x, -y' '-y, -z, x' '-z, x, -y' 'y, -z, -x' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' 'z+1/2, x+1/2, y+1/2' 'y+1/2, z+1/2, x+1/2' '-z+1/2, -x+1/2, y+1/2' '-y+1/2, z+1/2, -x+1/2' 'z+1/2, -x+1/2, -y+1/2' '-y+1/2, -z+1/2, x+1/2' '-z+1/2, x+1/2, -y+1/2' 'y+1/2, -z+1/2, -x+1/2' _cell_length_a 16.1817(5) _cell_length_b 16.1817(5) _cell_length_c 16.1817(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4237.1(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1930 _cell_measurement_theta_min 2 _cell_measurement_theta_max 26 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.954 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2384 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.501 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.767 _exptl_absorpt_correction_T_max 0.767 _exptl_absorpt_process_details ; Blessing, R. H. (1995) Acta Cryst., A51, 33-38. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(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 -0.468359E-1 _diffrn_orient_matrix_ub_12 -0.169161E-1 _diffrn_orient_matrix_ub_13 -0.365937E-1 _diffrn_orient_matrix_ub_21 0.349343E-1 _diffrn_orient_matrix_ub_22 0.109669E-1 _diffrn_orient_matrix_ub_23 -0.497812E-1 _diffrn_orient_matrix_ub_31 0.201213E-1 _diffrn_orient_matrix_ub_32 -0.584158E-1 _diffrn_orient_matrix_ub_33 0.1251E-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 0.0547 _diffrn_reflns_av_unetI/netI 0.0495 _diffrn_reflns_number 1401 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.56 _diffrn_reflns_theta_max 25.98 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 777 _reflns_number_gt 648 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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^)+(0.1025P)^2^+20.3434P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 777 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1669 _refine_ls_wR_factor_gt 0.1551 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _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 0.40(6) _refine_diff_density_max 2.555 _refine_diff_density_min -1.222 _refine_diff_density_rms 0.163 #----------------------------------------------------------------------------# # 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 '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' Sb Sb -0.5866 1.5461 '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 1.8620(8) 1.7263(9) 1.8444(10) 0.042(3) Uani 1 1 d . . . C2 C 1.8771(11) 1.6931(9) 1.9230(9) 0.046(3) Uani 1 1 d . . . H2 H 1.876 1.7274 1.9707 0.055 Uiso 1 1 calc R . . C3 C 1.8937(9) 1.6099(9) 1.9296(9) 0.041(3) Uani 1 1 d . . . H3 H 1.9032 1.586 1.9824 0.049 Uiso 1 1 calc R . . C4 C 1.8964(10) 1.5609(9) 1.8595(9) 0.043(3) Uani 1 1 d . . . C5 C 1.8817(13) 1.5906(10) 1.7844(10) 0.057(4) Uani 1 1 d . . . H5 H 1.8838 1.555 1.7378 0.069 Uiso 1 1 calc R . . C6 C 1.8630(10) 1.6751(9) 1.7740(9) 0.047(3) Uani 1 1 d . . . H6 H 1.8514 1.6969 1.7208 0.056 Uiso 1 1 calc R . . F1 F 1.9130(6) 1.4789(4) 1.8709(6) 0.052(2) Uani 1 1 d . . . P1 P 1.8332(2) 1.8332(2) 1.8332(2) 0.0377(13) Uani 1 3 d S . . Cl1 Cl 2.0830(2) 1.7435(2) 1.8585(2) 0.0447(8) Uani 1 1 d . . . Se1 Se 1.90997(8) 1.90997(8) 1.90997(8) 0.0391(6) Uani 1 3 d S . . Sb1 Sb 2.11487(5) 1.88513(5) 1.88513(5) 0.0380(5) Uani 1 3 d S . . 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 0.026(6) 0.045(7) 0.054(8) -0.001(7) 0.012(6) -0.002(6) C2 0.056(9) 0.042(7) 0.038(7) 0.019(6) 0.005(7) -0.006(7) C3 0.041(7) 0.041(6) 0.041(6) 0.008(6) 0.005(6) 0.010(6) C4 0.048(8) 0.040(7) 0.041(7) 0.009(6) 0.004(6) 0.007(7) C5 0.074(11) 0.057(9) 0.041(8) 0.002(7) 0.004(8) 0.004(10) C6 0.056(9) 0.045(7) 0.040(7) -0.008(6) -0.011(7) 0.007(7) F1 0.060(5) 0.031(4) 0.064(5) -0.001(4) 0.005(5) 0.007(4) P1 0.0377(13) 0.0377(13) 0.0377(13) 0.0028(15) 0.0028(15) 0.0028(15) Cl1 0.0451(17) 0.0362(16) 0.0529(19) -0.0037(14) 0.0023(16) -0.0020(14) Se1 0.0391(6) 0.0391(6) 0.0391(6) -0.0013(6) -0.0013(6) -0.0013(6) Sb1 0.0380(5) 0.0380(5) 0.0380(5) -0.0009(4) 0.0009(4) 0.0009(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.40(2) . ? C1 C6 1.41(2) . ? C1 P1 1.800(15) . ? C2 C3 1.38(2) . ? C2 H2 0.95 . ? C3 C4 1.39(2) . ? C3 H3 0.95 . ? C4 C5 1.33(2) . ? C4 F1 1.366(16) . ? C5 C6 1.41(2) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? P1 C1 1.800(15) 6 ? P1 C1 1.800(15) 5 ? P1 Se1 2.153(7) . ? Cl1 Sb1 2.388(3) . ? Sb1 Cl1 2.388(3) 7_995 ? Sb1 Cl1 2.388(3) 8_959 ? 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 120.4(14) . . ? C2 C1 P1 120.3(12) . . ? C6 C1 P1 119.1(12) . . ? C3 C2 C1 118.6(14) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 120.2(13) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 F1 120.7(14) . . ? C5 C4 C3 122.4(14) . . ? F1 C4 C3 116.8(12) . . ? C4 C5 C6 119.9(15) . . ? C4 C5 H5 120 . . ? C6 C5 H5 120 . . ? C1 C6 C5 118.5(15) . . ? C1 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? C1 P1 C1 108.6(5) 6 . ? C1 P1 C1 108.6(5) 6 5 ? C1 P1 C1 108.6(5) . 5 ? C1 P1 Se1 110.3(5) 6 . ? C1 P1 Se1 110.3(5) . . ? C1 P1 Se1 110.3(5) 5 . ? Cl1 Sb1 Cl1 94.21(13) . 7_995 ? Cl1 Sb1 Cl1 94.21(13) . 8_959 ? Cl1 Sb1 Cl1 94.21(13) 7_995 8_959 ? # END of CIF # Attachment '- Compound5.cif' #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_rob5 _database_code_depnum_ccdc_archive 'CCDC 881803' #TrackingRef '- Compound5.cif' _audit_creation_date 2012-05-02T17:02:16-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H12 Bi1 Cl3 F3 P1 Se1' _chemical_formula_sum 'C18 H12 Bi Cl3 F3 P Se' _chemical_formula_weight 710.54 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting cubic _symmetry_space_group_name_H-M 'I 2 3' _symmetry_space_group_name_Hall 'I 2 2 3' _symmetry_Int_Tables_number 197 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x, -y, -z' '-x, y, -z' 'z, x, y' 'y, z, x' '-z, -x, y' '-y, z, -x' 'z, -x, -y' '-y, -z, x' '-z, x, -y' 'y, -z, -x' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' 'z+1/2, x+1/2, y+1/2' 'y+1/2, z+1/2, x+1/2' '-z+1/2, -x+1/2, y+1/2' '-y+1/2, z+1/2, -x+1/2' 'z+1/2, -x+1/2, -y+1/2' '-y+1/2, -z+1/2, x+1/2' '-z+1/2, x+1/2, -y+1/2' 'y+1/2, -z+1/2, -x+1/2' _cell_length_a 16.1403(9) _cell_length_b 16.1403(9) _cell_length_c 16.1403(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4204.7(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1393 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_diffrn 2.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2640 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 10.602 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.524 _exptl_absorpt_correction_T_max 0.6764 _exptl_absorpt_process_details ; Blessing, R. H. (1995) Acta Cryst., A51, 33-38. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(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 -0.82468E-2 _diffrn_orient_matrix_ub_12 -0.196942E-1 _diffrn_orient_matrix_ub_13 -0.581656E-1 _diffrn_orient_matrix_ub_21 0.386428E-1 _diffrn_orient_matrix_ub_22 -0.472751E-1 _diffrn_orient_matrix_ub_23 0.105277E-1 _diffrn_orient_matrix_ub_31 -0.477247E-1 _diffrn_orient_matrix_ub_32 -0.348757E-1 _diffrn_orient_matrix_ub_33 0.185753E-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_unetI/netI 0.0642 _diffrn_reflns_av_R_equivalents 0.0780 _diffrn_reflns_number 2214 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 1379 _reflns_number_gt 1183 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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^)+(0.0289P)^2^+88.1475P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1379 _refine_ls_number_parameters 82 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.002 _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 -0.002(19) _refine_diff_density_max 1.378 _refine_diff_density_min -1.391 _refine_diff_density_rms 0.2 #----------------------------------------------------------------------------# # 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 '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' Bi Bi -4.1077 10.2566 '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 0.8465(9) 0.7271(8) 0.8628(7) 0.032(3) Uani 1 1 d . . . C2 C 0.7768(8) 0.6776(9) 0.8655(9) 0.040(4) Uani 1 1 d . . . H2 H 0.7238 0.7013 0.8554 0.048 Uiso 1 1 calc R . . C3 C 0.7833(8) 0.5918(8) 0.8829(10) 0.038(3) Uani 1 1 d . . . H3 H 0.7366 0.5561 0.8848 0.045 Uiso 1 1 calc R . . C4 C 0.8624(8) 0.5648(8) 0.8970(8) 0.036(3) Uani 1 1 d . . . C5 C 0.9328(8) 0.6098(9) 0.8945(9) 0.038(3) Uani 1 1 d . . . H5 H 0.9854 0.5854 0.9043 0.045 Uiso 1 1 calc R . . C6 C 0.9244(8) 0.6956(8) 0.8764(9) 0.031(3) Uani 1 1 d . . . H6 H 0.9717 0.7305 0.8737 0.037 Uiso 1 1 calc R . . F1 F 0.8727(5) 0.4803(4) 0.9116(5) 0.044(2) Uani 1 1 d . . . P1 P 0.8350(2) 0.8350(2) 0.8350(2) 0.0250(12) Uani 1 3 d S . . Cl1 Cl 0.8547(2) 0.73600(19) 1.0816(2) 0.0347(7) Uani 1 1 d . . . Se1 Se 0.91305(7) 0.91305(7) 0.91305(7) 0.0263(5) Uani 1 3 d S . . Bi1 Bi 0.88379(3) 0.88379(3) 1.11621(3) 0.0272(2) Uani 1 3 d S . . 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 0.045(8) 0.031(7) 0.020(7) -0.003(5) 0.002(5) -0.006(6) C2 0.025(7) 0.048(8) 0.047(9) -0.001(7) -0.016(6) -0.004(6) C3 0.035(7) 0.036(7) 0.042(7) 0.012(7) 0.004(7) -0.005(5) C4 0.045(9) 0.028(7) 0.034(8) 0.002(6) 0.016(6) 0.001(6) C5 0.035(7) 0.031(7) 0.047(8) 0.005(7) 0.000(6) 0.010(6) C6 0.030(7) 0.032(7) 0.031(7) -0.003(6) 0.004(6) 0.009(5) F1 0.058(5) 0.021(4) 0.053(5) 0.005(3) 0.006(4) 0.006(4) P1 0.0250(12) 0.0250(12) 0.0250(12) 0.0021(13) 0.0021(13) 0.0021(13) Cl1 0.0454(19) 0.0271(16) 0.0318(16) -0.0007(13) 0.0025(14) -0.0050(14) Se1 0.0263(5) 0.0263(5) 0.0263(5) -0.0007(5) -0.0007(5) -0.0007(5) Bi1 0.0272(2) 0.0272(2) 0.0272(2) 0.0003(2) 0.0003(2) -0.0003(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.374(18) . ? C1 C2 1.380(18) . ? C1 P1 1.809(13) . ? C2 C3 1.417(19) . ? C2 H2 0.95 . ? C3 C4 1.369(18) . ? C3 H3 0.95 . ? C4 C5 1.349(18) . ? C4 F1 1.395(14) . ? C5 C6 1.421(19) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? P1 C1 1.809(13) 6 ? P1 C1 1.809(13) 5 ? P1 Se1 2.181(6) . ? Cl1 Bi1 2.494(3) . ? Bi1 Cl1 2.494(3) 11_757 ? Bi1 Cl1 2.494(3) 12_577 ? 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 121.8(12) . . ? C6 C1 P1 119.3(10) . . ? C2 C1 P1 118.8(11) . . ? C1 C2 C3 120.7(13) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 114.4(12) . . ? C4 C3 H3 122.8 . . ? C2 C3 H3 122.8 . . ? C5 C4 C3 127.5(13) . . ? C5 C4 F1 115.6(12) . . ? C3 C4 F1 116.8(11) . . ? C4 C5 C6 116.7(12) . . ? C4 C5 H5 121.6 . . ? C6 C5 H5 121.6 . . ? C1 C6 C5 118.7(12) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C1 P1 C1 108.2(5) . 6 ? C1 P1 C1 108.2(5) . 5 ? C1 P1 C1 108.2(5) 6 5 ? C1 P1 Se1 110.7(4) . . ? C1 P1 Se1 110.7(4) 6 . ? C1 P1 Se1 110.7(4) 5 . ? Cl1 Bi1 Cl1 94.35(11) 11_757 . ? Cl1 Bi1 Cl1 94.35(11) 11_757 12_577 ? Cl1 Bi1 Cl1 94.35(11) . 12_577 ? # END of CIF # Attachment '- Compound6.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2012-04-26 at 08:25:03 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.4 # Request file : c:\wingx\files\archive.reqdat # CIF files read : rob dreduc sortav struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_rob6 _database_code_depnum_ccdc_archive 'CCDC 881804' #TrackingRef '- Compound6.cif' _audit_creation_date 2012-04-26T08:25:03-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H12 Bi1 Br3 F3 P1 Se1' _chemical_formula_sum 'C18 H12 Bi Br3 F3 P Se' _chemical_formula_weight 843.89 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting cubic _symmetry_space_group_name_H-M 'I 2 3' _symmetry_space_group_name_Hall 'I 2 2 3' _symmetry_Int_Tables_number 197 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x, -y, -z' '-x, y, -z' 'z, x, y' 'y, z, x' '-z, -x, y' '-y, z, -x' 'z, -x, -y' '-y, -z, x' '-z, x, -y' 'y, -z, -x' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' 'z+1/2, x+1/2, y+1/2' 'y+1/2, z+1/2, x+1/2' '-z+1/2, -x+1/2, y+1/2' '-y+1/2, z+1/2, -x+1/2' 'z+1/2, -x+1/2, -y+1/2' '-y+1/2, -z+1/2, x+1/2' '-z+1/2, x+1/2, -y+1/2' 'y+1/2, -z+1/2, -x+1/2' _cell_length_a 16.3328(8) _cell_length_b 16.3328(8) _cell_length_c 16.3328(8) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4356.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1304 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 2.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3072 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 15.367 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.26 _exptl_absorpt_correction_T_max 0.3087 _exptl_absorpt_process_details ; Blessing, R. H. (1995) Acta Cryst., A51, 33-38. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 100(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 -0.21492E-2 _diffrn_orient_matrix_ub_12 -0.573283E-1 _diffrn_orient_matrix_ub_13 -0.213889E-1 _diffrn_orient_matrix_ub_21 0.218383E-1 _diffrn_orient_matrix_ub_22 0.19274E-1 _diffrn_orient_matrix_ub_23 -0.53854E-1 _diffrn_orient_matrix_ub_31 0.571594E-1 _diffrn_orient_matrix_ub_32 -0.95193E-2 _diffrn_orient_matrix_ub_33 0.197712E-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 0.082 _diffrn_reflns_av_unetI/netI 0.0769 _diffrn_reflns_number 2034 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 1491 _reflns_number_gt 1302 _reflns_threshold_expression >2\s(I) _diffrn_reflns_reduction_process ; Scaled and merged with Sortav R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^ > 2\s(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^)+(0.0353P)^2^+52.4074P] where P=(Fo^2^+2Fc^2^)/3' _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 0.00025(8) _refine_ls_number_reflns 1491 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.0978 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 -0.057(19) _refine_diff_density_max 1.697 _refine_diff_density_min -1.158 _refine_diff_density_rms 0.198 #----------------------------------------------------------------------------# # 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' F F 0.0171 0.0103 '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' Bi Bi -4.1077 10.2566 '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 0.2726(7) 0.1395(6) 0.8459(7) 0.026(2) Uani 1 1 d . . . C2 C 0.3223(8) 0.1324(8) 0.7789(8) 0.037(3) Uani 1 1 d . . . H2 H 0.3001 0.139 0.7255 0.044 Uiso 1 1 calc R . . C3 C 0.4047(7) 0.1158(9) 0.7886(8) 0.038(3) Uani 1 1 d . . . H3 H 0.44 0.1131 0.7424 0.045 Uiso 1 1 calc R . . C4 C 0.4344(7) 0.1033(8) 0.8648(8) 0.035(3) Uani 1 1 d . . . C5 C 0.3860(8) 0.1098(8) 0.9336(7) 0.033(3) Uani 1 1 d . . . H5 H 0.4091 0.1016 0.9863 0.04 Uiso 1 1 calc R . . C6 C 0.3036(8) 0.1283(8) 0.9255(7) 0.035(3) Uani 1 1 d . . . H6 H 0.2692 0.1331 0.9722 0.042 Uiso 1 1 calc R . . F1 F 0.5153(4) 0.0897(5) 0.8761(5) 0.047(2) Uani 1 1 d . . . P1 P 0.16510(18) 0.16510(18) 0.83490(18) 0.0255(11) Uani 1 3 d S . . Se1 Se 0.08773(7) 0.08773(7) 0.91227(7) 0.0242(4) Uani 1 3 d S . . Br1 Br 0.14584(8) 0.26932(8) 1.07836(8) 0.0320(3) Uani 1 1 d . . . Bi1 Bi 0.11493(3) 0.11493(3) 1.11493(3) 0.0265(2) Uani 1 3 d S . . 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 0.033(6) 0.016(5) 0.029(6) 0.001(4) 0.001(5) 0.000(4) C2 0.030(6) 0.050(8) 0.031(6) 0.011(6) 0.005(5) -0.004(6) C3 0.029(6) 0.048(7) 0.036(7) 0.015(6) 0.006(5) -0.002(6) C4 0.024(6) 0.034(7) 0.048(8) 0.011(6) -0.009(5) 0.006(5) C5 0.037(6) 0.035(6) 0.028(6) -0.006(5) -0.004(5) 0.010(7) C6 0.033(6) 0.043(8) 0.029(6) -0.014(6) -0.001(5) 0.016(6) F1 0.013(3) 0.063(5) 0.064(5) -0.012(5) 0.000(3) 0.006(3) P1 0.0255(11) 0.0255(11) 0.0255(11) 0.0011(12) 0.0011(12) -0.0011(12) Se1 0.0242(4) 0.0242(4) 0.0242(4) 0.0006(4) 0.0006(4) -0.0006(4) Br1 0.0382(7) 0.0273(6) 0.0304(6) -0.0006(5) -0.0020(5) -0.0030(5) Bi1 0.0265(2) 0.0265(2) 0.0265(2) -0.00115(18) -0.00115(18) -0.00115(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.368(16) . ? C1 C6 1.407(17) . ? C1 P1 1.814(12) . ? C2 C3 1.383(18) . ? C2 H2 0.95 . ? C3 C4 1.351(17) . ? C3 H3 0.95 . ? C4 F1 1.354(13) . ? C4 C5 1.376(18) . ? C5 C6 1.386(17) . ? C5 H5 0.95 . ? C6 H6 0.95 . ? P1 C1 1.814(12) 11_656 ? P1 C1 1.814(12) 12_566 ? P1 Se1 2.189(5) . ? Br1 Bi1 2.6400(13) . ? Bi1 Br1 2.6400(13) 6_546 ? Bi1 Br1 2.6400(13) 5_456 ? 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(12) . . ? C2 C1 P1 120.9(10) . . ? C6 C1 P1 118.0(9) . . ? C1 C2 C3 120.1(12) . . ? C1 C2 H2 120 . . ? C3 C2 H2 120 . . ? C4 C3 C2 119.0(12) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 F1 120.0(12) . . ? C3 C4 C5 122.3(11) . . ? F1 C4 C5 117.5(11) . . ? C4 C5 C6 119.8(11) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 117.7(11) . . ? C5 C6 H6 121.1 . . ? C1 C6 H6 121.1 . . ? C1 P1 C1 107.2(4) 11_656 12_566 ? C1 P1 C1 107.2(4) 11_656 . ? C1 P1 C1 107.2(4) 12_566 . ? C1 P1 Se1 111.6(4) 11_656 . ? C1 P1 Se1 111.6(4) 12_566 . ? C1 P1 Se1 111.6(4) . . ? Br1 Bi1 Br1 94.40(4) . 6_546 ? Br1 Bi1 Br1 94.40(4) . 5_456 ? Br1 Bi1 Br1 94.40(4) 6_546 5_456 ? 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 -1(2) . . . . ? P1 C1 C2 C3 177.7(11) . . . . ? C1 C2 C3 C4 3(2) . . . . ? C2 C3 C4 F1 -177.8(12) . . . . ? C2 C3 C4 C5 -3(2) . . . . ? C3 C4 C5 C6 1(2) . . . . ? F1 C4 C5 C6 176.4(12) . . . . ? C4 C5 C6 C1 0(2) . . . . ? C2 C1 C6 C5 0.0(19) . . . . ? P1 C1 C6 C5 -179.2(10) . . . . ? C2 C1 P1 C1 -102.2(8) . . . 11_656 ? C6 C1 P1 C1 77.0(12) . . . 11_656 ? C2 C1 P1 C1 12.7(12) . . . 12_566 ? C6 C1 P1 C1 -168.1(9) . . . 12_566 ? C2 C1 P1 Se1 135.2(9) . . . . ? C6 C1 P1 Se1 -45.5(10) . . . . ? # END of CIF