# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. #TrackingRef 'AIE-CF3DSB.cif' _journal_coden_Cambridge 0182 #------------------ AUTHOR DETAILS -------------------------------------------# # Name and address of author for correspondence _publ_contact_author_name 'Werner Kaminsky' _publ_contact_author_address ; Department of Chemistry University of Washington Seattle Washington, 98195, USA ; _publ_contact_author_email kaminsky@chem.washington.edu _publ_contact_author_fax 00(206)6858665 _publ_contact_author_phone 00(206)5437585 _publ_section_title ; title here ; loop_ _publ_author_name _publ_author_address 'Zhenwei Shi' ; Department of Chemistry Univ. of Washington Seattle, WA 98195 USA ; 'Werner Kaminsky' ; Department of Chemistry Univ. of Washington Seattle, WA 98195 USA ; 'Alex Jen' ; Department of Chemistry Univ. of Washington Seattle, WA 98195 USA ; _publ_section_abstract ; Abstract here ; _publ_section_comment ; Details and comments here ; _publ_section_exptl_prep ; details of preparation here ; _publ_section_exptl_refinement ; All H atoms were initially located in a difference Fourier map and were refined with a riding model. H atoms were placed in geometrically idealised positions and constrained to ride on their parent atoms with C---H distances in the range 0.95-1.00 \%A. U~iso~ values were fixed such that they were 1.2U~eq~ of their parent atom U~eq~ for CH's and 1.5U~eq~ of their parent atom U~eq~ in case of methyl groups. ; # Insert blank lines between references _publ_section_references ; Bruker (2007) APEX2 (Version 2.1-4), SAINT (version 7.34A), SADABS (version 2007/4), BrukerAXS Inc, Madison, Wisconsin, USA. Flack H. D. & Bernardinelli, G. (71999). Acta Cryst. A55, 908-915. Flack H. D. & Bernardinelli, G. (2000). J. Appl. Cryst. 33, 1143-1148. Cambridge Structural Database: Allen, F. R. (2002). Acta Cryst. B58, 380-388. CrysAlis CCD, CrysAlis RED and associated programs: Oxford Diffraction (2006). Program name(s). Oxford Diffraction Ltd, Abingdon, England. 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. 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. 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. 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. 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. WinGX: Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838. ; _publ_requested_category FO # END of CIF # Attachment 'AIE-MeO-CF3DSB.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-01-10 at 10:52:51 # 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 : aie meo-cf3dsb_0m apexiitemplate data_aie_meo-cf3dsb_0m _database_code_depnum_ccdc_archive 'CCDC 874372' #TrackingRef 'AIE-MeO-CF3DSB.cif' _audit_creation_date 2011-01-10T10:52:51-00:00 _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 ; aie meo-cf3dsb ; _chemical_name_common 'aie meo-cf3dsb' _chemical_formula_moiety 'C28 H24 F6 O4' _chemical_formula_sum 'C28 H24 F6 O4' _chemical_formula_weight 538.47 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8528(6) _cell_length_b 5.7949(4) _cell_length_c 23.4430(17) _cell_angle_alpha 90 _cell_angle_beta 94.862(3) _cell_angle_gamma 90 _cell_volume 1198.32(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 145 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 556 _exptl_special_details ; exposure 20 seconds, steps per frame 0.5 degrees ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.13 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2007)' _exptl_absorpt_correction_T_min 0.9381 _exptl_absorpt_correction_T_max 0.9834 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_unetI/netI 0.0082 _diffrn_reflns_number 54014 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.45 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 2983 _reflns_number_gt 2688 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # 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^)+(0.0365P)^2^+0.5686P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2983 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.08 _refine_ls_wR_factor_gt 0.076 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.42 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 0.44312(11) 0.32583(16) -0.03664(4) 0.01406(18) Uani 1 1 d . . . H1 H 0.4035 0.2064 -0.0613 0.017 Uiso 1 1 calc R . . C2 C 0.34552(10) 0.49025(17) -0.01721(4) 0.01388(18) Uani 1 1 d . . . C3 C 0.59922(11) 0.33309(16) -0.02043(4) 0.01359(18) Uani 1 1 d . . . C4 C 0.70846(10) 0.16424(16) -0.03909(4) 0.01406(18) Uani 1 1 d . . . H4 H 0.8 0.1488 -0.0152 0.017 Uiso 1 1 calc R . . C5 C 0.69512(11) 0.02875(16) -0.08580(4) 0.01353(18) Uani 1 1 d . . . C6 C 0.56660(11) 0.02782(16) -0.13127(4) 0.01349(18) Uani 1 1 d . . . C7 C 0.46359(11) -0.15435(17) -0.13598(4) 0.01600(19) Uani 1 1 d . . . H7 H 0.4787 -0.2833 -0.1111 0.019 Uiso 1 1 calc R . . C8 C 0.33879(11) -0.15120(17) -0.17647(4) 0.01702(19) Uani 1 1 d . . . H8 H 0.2687 -0.2757 -0.1788 0.02 Uiso 1 1 calc R . . C9 C 0.31783(11) 0.03645(18) -0.21356(4) 0.01563(19) Uani 1 1 d . . . C10 C 0.42074(11) 0.21983(17) -0.20965(4) 0.01581(19) Uani 1 1 d . . . H10 H 0.4064 0.3475 -0.2349 0.019 Uiso 1 1 calc R . . C11 C 0.54388(11) 0.21550(17) -0.16883(4) 0.01461(18) Uani 1 1 d . . . H11 H 0.6134 0.3407 -0.1663 0.018 Uiso 1 1 calc R . . C12 C 0.82453(11) -0.12962(17) -0.09622(4) 0.01535(19) Uani 1 1 d . . . C13 C 0.09938(12) -0.1330(2) -0.26335(5) 0.0246(2) Uani 1 1 d . . . H13A H 0.1564 -0.2744 -0.2697 0.037 Uiso 1 1 calc R . . H13B H 0.0272 -0.104 -0.2966 0.037 Uiso 1 1 calc R . . H13C H 0.0442 -0.151 -0.2291 0.037 Uiso 1 1 calc R . . C14 C 0.13434(11) 0.33499(19) -0.07478(5) 0.0204(2) Uani 1 1 d . . . H14A H 0.1857 0.3586 -0.1097 0.031 Uiso 1 1 calc R . . H14B H 0.0253 0.3611 -0.083 0.031 Uiso 1 1 calc R . . H14C H 0.1517 0.1766 -0.0611 0.031 Uiso 1 1 calc R . . O1 O 0.19283(8) 0.49280(13) -0.03196(3) 0.01912(16) Uani 1 1 d . . . O2 O 0.20190(8) 0.05687(14) -0.25562(3) 0.02103(17) Uani 1 1 d . . . F1 F 0.93205(7) -0.14107(11) -0.05251(3) 0.02075(14) Uani 1 1 d . . . F2 F 0.89526(7) -0.06179(12) -0.14233(3) 0.02400(15) Uani 1 1 d . . . F3 F 0.77851(7) -0.34778(10) -0.10723(3) 0.02186(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0153(4) 0.0139(4) 0.0130(4) -0.0011(3) 0.0012(3) -0.0022(3) C2 0.0129(4) 0.0158(4) 0.0128(4) 0.0003(3) 0.0008(3) -0.0014(3) C3 0.0154(4) 0.0134(4) 0.0121(4) 0.0004(3) 0.0020(3) -0.0005(3) C4 0.0140(4) 0.0134(4) 0.0147(4) 0.0012(3) 0.0009(3) 0.0000(3) C5 0.0136(4) 0.0125(4) 0.0146(4) 0.0013(3) 0.0016(3) -0.0001(3) C6 0.0147(4) 0.0138(4) 0.0121(4) -0.0018(3) 0.0020(3) 0.0007(3) C7 0.0191(4) 0.0135(4) 0.0155(4) 0.0010(3) 0.0022(3) -0.0005(3) C8 0.0168(4) 0.0158(4) 0.0186(4) -0.0026(4) 0.0018(3) -0.0034(4) C9 0.0146(4) 0.0180(5) 0.0143(4) -0.0031(3) 0.0014(3) 0.0016(4) C10 0.0182(4) 0.0148(4) 0.0147(4) 0.0013(3) 0.0025(3) 0.0018(4) C11 0.0163(4) 0.0125(4) 0.0154(4) -0.0009(3) 0.0032(3) -0.0011(3) C12 0.0168(4) 0.0144(4) 0.0149(4) -0.0009(3) 0.0012(3) 0.0002(4) C13 0.0194(5) 0.0291(6) 0.0245(5) -0.0072(4) -0.0026(4) -0.0043(4) C14 0.0160(4) 0.0227(5) 0.0216(5) -0.0063(4) -0.0037(4) -0.0016(4) O1 0.0122(3) 0.0218(4) 0.0229(4) -0.0080(3) -0.0015(3) -0.0002(3) O2 0.0176(3) 0.0243(4) 0.0202(4) -0.0005(3) -0.0048(3) -0.0012(3) F1 0.0180(3) 0.0219(3) 0.0214(3) -0.0029(2) -0.0035(2) 0.0054(2) F2 0.0250(3) 0.0267(3) 0.0218(3) 0.0030(3) 0.0109(2) 0.0051(3) F3 0.0234(3) 0.0131(3) 0.0287(3) -0.0047(2) -0.0001(2) 0.0016(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 C2 1.3888(13) . ? C1 C3 1.4024(13) . ? C1 H1 0.95 . ? C2 O1 1.3667(11) . ? C2 C3 1.4116(13) 3_665 ? C3 C2 1.4116(13) 3_665 ? C3 C4 1.4683(13) . ? C4 C5 1.3445(13) . ? C4 H4 0.95 . ? C5 C6 1.4918(13) . ? C5 C12 1.5039(13) . ? C6 C7 1.3932(13) . ? C6 C11 1.4030(13) . ? C7 C8 1.3943(13) . ? C7 H7 0.95 . ? C8 C9 1.3948(14) . ? C8 H8 0.95 . ? C9 O2 1.3668(11) . ? C9 C10 1.3976(14) . ? C10 C11 1.3886(13) . ? C10 H10 0.95 . ? C11 H11 0.95 . ? C12 F1 1.3396(11) . ? C12 F3 1.3465(11) . ? C12 F2 1.3528(11) . ? C13 O2 1.4282(13) . ? C13 H13A 0.98 . ? C13 H13B 0.98 . ? C13 H13C 0.98 . ? C14 O1 1.4226(12) . ? C14 H14A 0.98 . ? C14 H14B 0.98 . ? C14 H14C 0.98 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C3 121.11(9) . . ? C2 C1 H1 119.4 . . ? C3 C1 H1 119.4 . . ? O1 C2 C1 123.64(9) . . ? O1 C2 C3 115.68(8) . 3_665 ? C1 C2 C3 120.68(9) . 3_665 ? C1 C3 C2 118.19(9) . 3_665 ? C1 C3 C4 123.92(8) . . ? C2 C3 C4 117.86(8) 3_665 . ? C5 C4 C3 128.11(9) . . ? C5 C4 H4 115.9 . . ? C3 C4 H4 115.9 . . ? C4 C5 C6 126.38(9) . . ? C4 C5 C12 118.23(9) . . ? C6 C5 C12 115.29(8) . . ? C7 C6 C11 118.66(9) . . ? C7 C6 C5 120.92(8) . . ? C11 C6 C5 120.38(8) . . ? C6 C7 C8 121.30(9) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C7 C8 C9 119.37(9) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? O2 C9 C8 124.70(9) . . ? O2 C9 C10 115.27(9) . . ? C8 C9 C10 120.02(9) . . ? C11 C10 C9 120.05(9) . . ? C11 C10 H10 120 . . ? C9 C10 H10 120 . . ? C10 C11 C6 120.59(9) . . ? C10 C11 H11 119.7 . . ? C6 C11 H11 119.7 . . ? F1 C12 F3 106.50(8) . . ? F1 C12 F2 106.17(8) . . ? F3 C12 F2 105.82(8) . . ? F1 C12 C5 114.06(8) . . ? F3 C12 C5 112.45(8) . . ? F2 C12 C5 111.28(8) . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O1 C14 H14A 109.5 . . ? O1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C2 O1 C14 117.69(8) . . ? C9 O2 C13 117.07(8) . . ? # END of CIF #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_ref_3lt_0m _database_code_depnum_ccdc_archive 'CCDC 884441' #TrackingRef 'AIE-CF3DSB.cif' _audit_creation_date 2012-05-22T14:10:18-00:00 _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 ; ref_3lt ; _chemical_name_common ref_3lt _chemical_formula_moiety 'C24 H16 F6' _chemical_formula_sum 'C24 H16 F6' _chemical_formula_weight 418.37 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.4710(16) _cell_length_b 7.640(2) _cell_length_c 23.076(7) _cell_angle_alpha 90 _cell_angle_beta 95.405(14) _cell_angle_gamma 90 _cell_volume 960.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 99 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_special_details ; 10 seconds exposure, 0.5 degree steps, DX=40mm ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.124 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2007)' _exptl_absorpt_correction_T_min 0.9756 _exptl_absorpt_correction_T_max 0.9938 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area-detector' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_unetI/netI 0.048 _diffrn_reflns_number 7011 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 28.32 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.995 _reflns_number_total 2390 _reflns_number_gt 1647 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # 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^)+(0.0369P)^2^+0.8794P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2390 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.083 _refine_ls_R_factor_gt 0.0518 _refine_ls_wR_factor_ref 0.1209 _refine_ls_wR_factor_gt 0.109 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.272 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.058 #----------------------------------------------------------------------------# # 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' 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 0.2031(4) 1.0434(3) 0.03785(8) 0.0218(4) Uani 1 1 d . . . H1 H 0.3421 1.0749 0.0635 0.026 Uiso 1 1 calc R . . C2 C -0.0466(4) 0.8280(3) -0.01429(8) 0.0214(4) Uani 1 1 d . . . H2 H -0.0793 0.7093 -0.0245 0.026 Uiso 1 1 calc R . . C3 C 0.1587(4) 0.8674(3) 0.02423(8) 0.0190(4) Uani 1 1 d . . . C4 C 0.3088(4) 0.7205(3) 0.04787(8) 0.0205(4) Uani 1 1 d . . . H4 H 0.2947 0.616 0.0255 0.025 Uiso 1 1 calc R . . C5 C 0.4621(4) 0.7123(3) 0.09617(8) 0.0192(4) Uani 1 1 d . . . C6 C 0.5161(4) 0.8537(3) 0.14022(8) 0.0183(4) Uani 1 1 d . . . C7 C 0.3629(4) 0.8764(3) 0.18428(9) 0.0238(5) Uani 1 1 d . . . H7 H 0.2233 0.8032 0.1858 0.029 Uiso 1 1 calc R . . C8 C 0.4123(4) 1.0050(3) 0.22594(9) 0.0284(5) Uani 1 1 d . . . H8 H 0.3069 1.0196 0.256 0.034 Uiso 1 1 calc R . . C9 C 0.6143(4) 1.1120(3) 0.22383(9) 0.0274(5) Uani 1 1 d . . . H9 H 0.6477 1.2005 0.2524 0.033 Uiso 1 1 calc R . . C10 C 0.7681(4) 1.0903(3) 0.18019(9) 0.0268(5) Uani 1 1 d . . . H10 H 0.9067 1.1645 0.1787 0.032 Uiso 1 1 calc R . . C11 C 0.7205(4) 0.9606(3) 0.13861(9) 0.0237(5) Uani 1 1 d . . . H11 H 0.828 0.9448 0.109 0.028 Uiso 1 1 calc R . . C12 C 0.5873(4) 0.5423(3) 0.11222(9) 0.0242(5) Uani 1 1 d . . . F1 F 0.5335(3) 0.41338(16) 0.07390(5) 0.0348(4) Uani 1 1 d . . . F2 F 0.5284(3) 0.48366(17) 0.16364(5) 0.0366(4) Uani 1 1 d . . . F3 F 0.8320(3) 0.55833(19) 0.11725(7) 0.0426(4) 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 0.0229(11) 0.0229(10) 0.0185(9) 0.0017(8) -0.0037(8) -0.0040(9) C2 0.0267(11) 0.0175(9) 0.0192(9) -0.0004(8) -0.0017(8) -0.0034(8) C3 0.0209(11) 0.0209(10) 0.0152(9) 0.0018(7) 0.0013(7) 0.0000(9) C4 0.0255(11) 0.0183(9) 0.0176(9) -0.0015(8) 0.0026(8) 0.0004(8) C5 0.0218(11) 0.0170(9) 0.0188(9) 0.0010(8) 0.0021(8) 0.0003(8) C6 0.0191(10) 0.0187(9) 0.0163(9) 0.0017(7) -0.0032(7) 0.0033(8) C7 0.0263(11) 0.0213(10) 0.0239(10) 0.0032(8) 0.0026(8) 0.0009(9) C8 0.0342(13) 0.0282(12) 0.0233(10) -0.0022(9) 0.0050(9) 0.0039(10) C9 0.0354(13) 0.0224(11) 0.0226(10) -0.0039(8) -0.0075(9) 0.0045(10) C10 0.0240(11) 0.0215(11) 0.0330(11) -0.0003(9) -0.0064(9) -0.0018(9) C11 0.0211(11) 0.0254(11) 0.0247(10) -0.0008(9) 0.0024(8) 0.0000(9) C12 0.0305(12) 0.0199(10) 0.0211(10) -0.0004(8) -0.0029(9) 0.0032(9) F1 0.0516(9) 0.0210(7) 0.0294(7) -0.0062(5) -0.0082(6) 0.0089(6) F2 0.0613(10) 0.0241(7) 0.0244(6) 0.0080(5) 0.0031(6) 0.0088(7) F3 0.0276(8) 0.0339(8) 0.0649(10) 0.0014(7) -0.0034(7) 0.0092(6) #----------------------------------------------------------------------------# # 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 1.380(3) 3_575 ? C1 C3 1.397(3) . ? C1 H1 0.95 . ? C2 C1 1.380(3) 3_575 ? C2 C3 1.397(3) . ? C2 H2 0.95 . ? C3 C4 1.465(3) . ? C4 C5 1.332(3) . ? C4 H4 0.95 . ? C5 C6 1.494(3) . ? C5 C12 1.499(3) . ? C6 C7 1.388(3) . ? C6 C11 1.388(3) . ? C7 C8 1.383(3) . ? C7 H7 0.95 . ? C8 C9 1.379(3) . ? C8 H8 0.95 . ? C9 C10 1.382(3) . ? C9 H9 0.95 . ? C10 C11 1.387(3) . ? C10 H10 0.95 . ? C11 H11 0.95 . ? C12 F2 1.336(2) . ? C12 F3 1.339(3) . ? C12 F1 1.338(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 C2 C1 C3 120.51(19) 3_575 . ? C2 C1 H1 119.7 3_575 . ? C3 C1 H1 119.7 . . ? C1 C2 C3 121.92(19) 3_575 . ? C1 C2 H2 119 3_575 . ? C3 C2 H2 119 . . ? C1 C3 C2 117.57(18) . . ? C1 C3 C4 125.02(18) . . ? C2 C3 C4 117.41(18) . . ? C5 C4 C3 129.37(19) . . ? C5 C4 H4 115.3 . . ? C3 C4 H4 115.3 . . ? C4 C5 C6 127.17(18) . . ? C4 C5 C12 118.99(18) . . ? C6 C5 C12 113.72(16) . . ? C7 C6 C11 119.34(19) . . ? C7 C6 C5 119.60(19) . . ? C11 C6 C5 121.04(18) . . ? C8 C7 C6 120.4(2) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C9 C8 C7 120.1(2) . . ? C9 C8 H8 120 . . ? C7 C8 H8 120 . . ? C8 C9 C10 120.0(2) . . ? C8 C9 H9 120 . . ? C10 C9 H9 120 . . ? C9 C10 C11 120.2(2) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C6 120.1(2) . . ? C10 C11 H11 120 . . ? C6 C11 H11 120 . . ? F2 C12 F3 106.06(17) . . ? F2 C12 F1 106.50(17) . . ? F3 C12 F1 106.29(18) . . ? F2 C12 C5 111.55(17) . . ? F3 C12 C5 111.83(18) . . ? F1 C12 C5 114.08(16) . . ?