Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author ; Toshimasa Katagiri Department of Applied Chemistry, Faculty of Engineering, Okayama University 3-1-1 Tsushimanaka, Okayama Japan ; _publ_contact_author_email tkata@cc.okayama-u.ac.jp _publ_section_title ; Nanoporous organic layered crystals of double-headed bis(trifluorolactate)s: Hydrogen-bonded systematic crystal structures controlled by the symmetries of molecular components. ; _publ_section_references ; teXsan Single Crystal Structure Analysis Software. Version 1.11 - Molecular Structure Corporation, Rigaku Corporation. (2000). . MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. SIR97 - A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna, J. Appl. Cryst. 1999, 32, 115-119. SHELX97 [Includes SHELXS97, SHELXL97, CIFTAB] - Programs for Crystal Structure Analysis (Release 97-2). G. M. Sheldrick, Instit\"ut f\"ur Anorganische Chemie der Universit\"at, Tammanstrasse 4, D-3400 G\"ottingen, Germany, 1998. SAPI91, Structure Analysis Programs with Intelligent Control, H.-F. Fan, Rigaku Corporation, 1991. WinGX - L.J. Farrugia, J. Appl. Cryst., 1999, 32, 837-838. PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands, A. L. Spek, 1998. SQUEEZE - P. v.d. Sluis and A. L. Spek, Acta Crystallogr., 1990, A46, 194-201. ORTEP3 for Windows - L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565. MERCURY - I. J. Bruno, J. C. Cole, P. R. Edgington, M. K. Kessler, C. F. Macrae, P. McCabe, J. Pearson and R. Taylor, Acta Crystallogr., B58, 2002, 389-397. ; _publ_contact_author_name 'Toshimasa Katagiri' loop_ _publ_author_name 'Satoshi Takahashi' 'Toshimasa Katagiri' 'Kenji Uneyama' #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_3a _database_code_depnum_ccdc_archive 'CCDC 246918' _audit_creation_method SHELXL-97 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C10 H12 F6 O6 ' _chemical_formula_moiety 'C10 H12 F6 O6 ' _chemical_formula_weight 342.19 _chemical_melting_point 357 _chemical_name_common '(S,S)-(-)-tetramethylene bis(3,3,3-trifluorolactate)' _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= -6.28 (c = 1.0, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.2325(14) _cell_length_b 5.0006(5) _cell_length_c 17.966(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.189(3) _cell_angle_gamma 90.00 _cell_volume 645.97(19) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5056 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 150(1) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_special_details ;A needle crystal was mounted on a glass capillary. The crystal was cooled by cold nitrogen flux of a low temperature device during the data collection. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 2474 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1466 _reflns_number_gt 1390 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku)' _computing_cell_refinement 'PAPID-AUTO (Rigaku)' _computing_data_reduction 'teXsan Ver. 1.11 (MSC)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX Ver. 1.7 (Farrugia, 1999)' _computing_molecular_graphics 'Mercury Ver. 1.3 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # 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. Non H-atoms were refined anisotropically. H-atoms of OH have been located from Fourier difference maps and fixed to its position. The remaining H-atoms were included in calculated positions and treated as riding atoms using the SHELXL default parameters. ; _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^)+(0.0652P)^2^+0.4541P] 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_extinction_coef ? _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that of its precursor (S)-trifluorolactic acid at the chiral centre C2. This compound has no atom heavier than Si and analyzed by Mo radiation so that Flack parameter is not listed. Freidel pairs were merged before refinement. ; _refine_ls_number_reflns 1466 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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 F1 F -0.1129(3) 0.2103(7) 0.88337(12) 0.0396(6) Uani 1 1 d . . . F2 F -0.0080(3) 0.5551(6) 0.83186(12) 0.0371(6) Uani 1 1 d . . . F3 F 0.1239(3) 0.1735(6) 0.82146(11) 0.0364(6) Uani 1 1 d . . . F4 F 0.9602(3) 0.8746(5) 0.68609(11) 0.0328(5) Uani 1 1 d . . . F5 F 0.8052(3) 1.2418(6) 0.68558(11) 0.0348(6) Uani 1 1 d . . . F6 F 1.0693(3) 1.2335(6) 0.64209(12) 0.0359(6) Uani 1 1 d . . . O1 O 0.1759(3) 0.1557(6) 0.98535(13) 0.0279(6) Uani 1 1 d . . . O2 O 0.4990(3) 0.3357(6) 0.94652(12) 0.0251(5) Uani 1 1 d . . . O3 O 0.3598(3) 0.6747(6) 0.87884(12) 0.0238(5) Uani 1 1 d . . . O4 O 0.5615(3) 0.8744(6) 0.62154(11) 0.0239(6) Uani 1 1 d . . . O5 O 0.6624(3) 0.6181(6) 0.53106(12) 0.0263(5) Uani 1 1 d . . . O6 O 0.9569(4) 0.9337(5) 0.52473(13) 0.0281(6) Uani 1 1 d . . . C1 C 0.0412(4) 0.3304(9) 0.86872(17) 0.0255(7) Uani 1 1 d . . . C2 C 0.1699(4) 0.3850(8) 0.94067(16) 0.0215(7) Uani 1 1 d . . . H2 H 0.1185 0.5329 0.9677 0.026 Uiso 1 1 calc R . . C3 C 0.3633(4) 0.4625(7) 0.92210(16) 0.0205(7) Uani 1 1 d . . . C4 C 0.5333(4) 0.7578(9) 0.85108(16) 0.0241(7) Uani 1 1 d . . . H4A H 0.6380 0.6938 0.8846 0.029 Uiso 1 1 calc R . . H4B H 0.5393 0.9515 0.8497 0.029 Uiso 1 1 calc R . . C5 C 0.5445(5) 0.6468(9) 0.77364(18) 0.0293(8) Uani 1 1 d . . . H5A H 0.5491 0.4532 0.7765 0.035 Uiso 1 1 calc R . . H5B H 0.6593 0.7074 0.7558 0.035 Uiso 1 1 calc R . . C6 C 0.3833(5) 0.7277(11) 0.71762(17) 0.0320(9) Uani 1 1 d . . . H6A H 0.3567 0.9156 0.7247 0.038 Uiso 1 1 calc R . . H6B H 0.2742 0.6267 0.7277 0.038 Uiso 1 1 calc R . . C7 C 0.4168(4) 0.6840(9) 0.63691(17) 0.0277(8) Uani 1 1 d . . . H7A H 0.4576 0.5020 0.6295 0.033 Uiso 1 1 calc R . . H7B H 0.3037 0.7161 0.6039 0.033 Uiso 1 1 calc R . . C8 C 0.6743(4) 0.8114(7) 0.57063(15) 0.0183(6) Uani 1 1 d . . . C9 C 0.8215(4) 1.0275(7) 0.56802(16) 0.0201(6) Uani 1 1 d . . . H9 H 0.7640 1.1890 0.5449 0.024 Uiso 1 1 calc R . . C10 C 0.9137(4) 1.0949(8) 0.64670(18) 0.0240(7) Uani 1 1 d . . . H1 H 0.2836 0.0493 0.9855 0.047 Uiso 1 1 d . . . H12 H 1.0229 1.0680 0.5091 0.047 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 F1 0.0146(9) 0.0601(18) 0.0427(11) 0.0092(12) -0.0026(7) -0.0103(11) F2 0.0224(10) 0.0478(16) 0.0391(11) 0.0150(11) -0.0057(8) 0.0058(10) F3 0.0297(11) 0.0514(17) 0.0271(9) -0.0092(10) -0.0017(7) 0.0021(11) F4 0.0255(10) 0.0413(15) 0.0302(10) 0.0131(10) -0.0031(7) 0.0022(10) F5 0.0312(11) 0.0458(15) 0.0281(9) -0.0170(10) 0.0058(7) 0.0030(11) F6 0.0300(11) 0.0429(15) 0.0353(10) -0.0019(10) 0.0064(8) -0.0154(11) O1 0.0150(10) 0.0414(18) 0.0277(11) 0.0121(11) 0.0045(7) 0.0006(11) O2 0.0150(10) 0.0289(15) 0.0309(11) 0.0021(11) -0.0004(8) 0.0030(10) O3 0.0149(10) 0.0330(15) 0.0240(10) 0.0056(10) 0.0047(7) 0.0040(10) O4 0.0176(11) 0.0335(16) 0.0213(9) -0.0046(10) 0.0050(7) -0.0005(10) O5 0.0331(13) 0.0208(14) 0.0260(11) -0.0021(10) 0.0074(9) -0.0001(10) O6 0.0358(14) 0.0198(13) 0.0329(12) -0.0044(10) 0.0230(10) -0.0033(10) C1 0.0144(14) 0.036(2) 0.0257(14) 0.0049(15) -0.0004(10) 0.0015(14) C2 0.0120(13) 0.033(2) 0.0201(13) 0.0022(13) 0.0024(9) -0.0004(13) C3 0.0194(14) 0.0272(19) 0.0152(12) -0.0044(12) 0.0022(10) -0.0009(12) C4 0.0169(14) 0.032(2) 0.0235(13) 0.0025(13) 0.0044(10) -0.0047(13) C5 0.0256(16) 0.037(2) 0.0254(15) 0.0007(14) 0.0044(11) 0.0023(15) C6 0.0213(16) 0.048(3) 0.0264(15) 0.0038(16) 0.0019(11) -0.0026(17) C7 0.0173(14) 0.042(2) 0.0240(14) -0.0028(15) 0.0008(10) -0.0054(15) C8 0.0181(14) 0.0213(18) 0.0153(11) 0.0026(12) 0.0012(9) 0.0053(12) C9 0.0246(15) 0.0176(17) 0.0188(13) 0.0007(11) 0.0057(11) 0.0071(12) C10 0.0201(15) 0.027(2) 0.0251(14) -0.0009(13) 0.0052(11) 0.0000(13) #----------------------------------------------------------------------------# # 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 F1 C1 1.318(4) . no F2 C1 1.333(5) . no F3 C1 1.343(4) . no F4 C10 1.333(4) . no F5 C10 1.327(4) . no F6 C10 1.332(4) . no O1 C2 1.398(4) . no O1 H1 0.9400 . no O2 C3 1.210(4) . no O3 C3 1.314(4) . no O3 C4 1.460(4) . no O4 C8 1.327(4) . no O4 C7 1.464(4) . no O5 C8 1.197(4) . no O6 C9 1.396(4) . no O6 H12 0.8800 . no C1 C2 1.534(4) . no C2 C3 1.523(4) . no C2 H2 0.9800 . no C4 C5 1.508(4) . no C4 H4A 0.9700 . no C4 H4B 0.9700 . no C5 C6 1.511(4) . no C5 H5A 0.9700 . no C5 H5B 0.9700 . no C6 C7 1.512(4) . no C6 H6A 0.9700 . no C6 H6B 0.9700 . no C7 H7A 0.9700 . no C7 H7B 0.9700 . no C8 C9 1.521(5) . no C9 C10 1.534(4) . no C9 H9 0.9800 . no 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 O1 H1 116.00 . . no C3 O3 C4 118.0(3) . . no C8 O4 C7 118.7(3) . . no C9 O6 H12 110.00 . . no F1 C1 F2 107.3(3) . . no F1 C1 F3 107.7(3) . . no F2 C1 F3 107.0(3) . . no F1 C1 C2 111.3(3) . . no F2 C1 C2 112.0(3) . . no F3 C1 C2 111.5(3) . . no O1 C2 C3 111.2(3) . . no O1 C2 C1 108.4(3) . . no C3 C2 C1 110.4(2) . . no O1 C2 H2 108.9 . . no C3 C2 H2 108.9 . . no C1 C2 H2 108.9 . . no O2 C3 O3 127.0(3) . . no O2 C3 C2 121.0(3) . . no O3 C3 C2 112.0(3) . . no O3 C4 C5 110.1(3) . . no O3 C4 H4A 109.6 . . no C5 C4 H4A 109.6 . . no O3 C4 H4B 109.6 . . no C5 C4 H4B 109.6 . . no H4A C4 H4B 108.1 . . no C4 C5 C6 113.7(3) . . no C4 C5 H5A 108.8 . . no C6 C5 H5A 108.8 . . no C4 C5 H5B 108.8 . . no C6 C5 H5B 108.8 . . no H5A C5 H5B 107.7 . . no C5 C6 C7 114.1(3) . . no C5 C6 H6A 108.7 . . no C7 C6 H6A 108.7 . . no C5 C6 H6B 108.7 . . no C7 C6 H6B 108.7 . . no H6A C6 H6B 107.6 . . no O4 C7 C6 106.2(3) . . no O4 C7 H7A 110.5 . . no C6 C7 H7A 110.5 . . no O4 C7 H7B 110.5 . . no C6 C7 H7B 110.5 . . no H7A C7 H7B 108.7 . . no O5 C8 O4 126.2(3) . . no O5 C8 C9 124.1(3) . . no O4 C8 C9 109.7(3) . . no O6 C9 C8 108.3(3) . . no O6 C9 C10 109.0(3) . . no C8 C9 C10 111.3(3) . . no O6 C9 H9 109.4 . . no C8 C9 H9 109.4 . . no C10 C9 H9 109.4 . . no F5 C10 F6 107.2(3) . . no F5 C10 F4 107.9(3) . . no F6 C10 F4 107.2(3) . . no F5 C10 C9 112.6(3) . . no F6 C10 C9 110.1(3) . . no F4 C10 C9 111.6(3) . . no 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 F1 C1 C2 O1 44.6(4) . . . . no F2 C1 C2 O1 164.7(3) . . . . no F3 C1 C2 O1 -75.6(4) . . . . no F1 C1 C2 C3 166.8(3) . . . . no F2 C1 C2 C3 -73.2(4) . . . . no F3 C1 C2 C3 46.6(4) . . . . no C4 O3 C3 O2 5.7(5) . . . . no C4 O3 C3 C2 -174.7(3) . . . . no O1 C2 C3 O2 -1.7(4) . . . . no C1 C2 C3 O2 -122.1(4) . . . . no O1 C2 C3 O3 178.7(3) . . . . no C1 C2 C3 O3 58.3(4) . . . . no C3 O3 C4 C5 96.0(3) . . . . no O3 C4 C5 C6 57.3(5) . . . . no C4 C5 C6 C7 164.2(4) . . . . no C8 O4 C7 C6 150.8(3) . . . . no C5 C6 C7 O4 -67.9(5) . . . . no C7 O4 C8 O5 5.6(5) . . . . no C7 O4 C8 C9 -175.9(2) . . . . no O5 C8 C9 O6 -12.2(4) . . . . no O4 C8 C9 O6 169.2(2) . . . . no O5 C8 C9 C10 -132.1(3) . . . . no O4 C8 C9 C10 49.4(3) . . . . no O6 C9 C10 F5 165.3(3) . . . . no C8 C9 C10 F5 -75.3(4) . . . . no O6 C9 C10 F6 45.7(4) . . . . no C8 C9 C10 F6 165.1(3) . . . . no O6 C9 C10 F4 -73.2(3) . . . . no C8 C9 C10 F4 46.2(3) . . . . no _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.886 _refine_diff_density_max 0.572 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.062 #==END #----------------------------------------------------------------------------# data_3b _database_code_depnum_ccdc_archive 'CCDC 246919' _audit_creation_method SHELXL-97 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C11 H14 F6 O6 ' _chemical_formula_moiety 'C11 H14 F6 O6 ' _chemical_formula_weight 356.22 _chemical_melting_point 374 _chemical_name_common '(S,S)-(-)-pentamethylene bis(3,3,3-trifluorolactate)' _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= -6.61 (c = 1.0, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 18.816(3) _cell_length_b 5.1374(6) _cell_length_c 7.7556(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.202(2) _cell_angle_gamma 90.00 _cell_volume 745.31(17) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2375 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 25.3 _cell_measurement_temperature 296(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_special_details ; A needle crystal was mounted on a glass capillary. The data was collected at room temperature. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_radiation_monochromator graphite _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 1816 _diffrn_reflns_av_R_equivalents 0.056 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 27.48 _reflns_number_total 839 _reflns_number_gt 553 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku)' _computing_cell_refinement 'PAPID-AUTO (Rigaku)' _computing_data_reduction 'teXsan Ver. 1.11 (MSC)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX Ver. 1.7 (Farrugia, 1999)' _computing_molecular_graphics 'Mercury Ver. 1.3 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # 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. Non H-atoms were refined anisotropically. H-atoms of OH have been located from Fourier difference maps and fixed to its position. The remaining H-atoms were included in calculated positions and treated as riding atoms using the SHELXL default parameters. ; _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^)+(0.1087P)^2^+0.0523P] 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_coef 0.031(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that of its precursor (S)-trifluorolactic acid at the chiral centre C2. This compound has no atom heavier than Si and analyzed by Mo radiation so that Flack parameter is not listed. Friedel pairs were merged before refinement. ; _refine_ls_number_reflns 839 _refine_ls_number_parameters 106 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1833 _refine_ls_wR_factor_gt 0.1641 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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 F1 F -0.8904(2) -0.4573(12) -0.5876(5) 0.1154(16) Uani 1 1 d . . . F2 F -0.9196(2) -0.0831(9) -0.5012(5) 0.1076(15) Uani 1 1 d . . . F3 F -0.93860(17) -0.4184(11) -0.3524(4) 0.1013(15) Uani 1 1 d . . . O1 O -0.7732(2) -0.1989(9) -0.4692(7) 0.0996(16) Uani 1 1 d . . . O2 O -0.7885(2) 0.1209(9) -0.2069(5) 0.0840(13) Uani 1 1 d . . . O3 O -0.8572(2) -0.1678(10) -0.0870(4) 0.0821(13) Uani 1 1 d . . . C1 C -0.8924(3) -0.3105(14) -0.4475(7) 0.0750(15) Uani 1 1 d . . . C2 C -0.8195(2) -0.2822(12) -0.3516(7) 0.0684(13) Uani 1 1 d . . . H2 H -0.8034 -0.4505 -0.3023 0.082 Uiso 1 1 calc R . . C3 C -0.8200(3) -0.0840(12) -0.2090(7) 0.0685(14) Uani 1 1 d . . . C4 C -0.8654(4) 0.015(2) 0.0597(7) 0.102(3) Uani 1 1 d . . . H4A H -0.8656 -0.0820 0.1667 0.122 Uiso 1 1 calc R . . H4B H -0.8253 0.1351 0.0729 0.122 Uiso 1 1 calc R . . C5 C -0.9315(4) 0.1606(16) 0.0264(8) 0.101(3) Uani 1 1 d . . . H5A H -0.9287 0.2664 -0.0762 0.121 Uiso 1 1 calc R . . H5B H -0.9351 0.2782 0.1230 0.121 Uiso 1 1 calc R . . C6 C -1.0000 0.001(2) 0.0000 0.081(2) Uani 1 2 d S . . H6A H -1.0021 -0.1110 0.1002 0.097 Uiso 0.50 1 calc PR . . H6B H -0.9979 -0.1110 -0.1002 0.097 Uiso 0.50 1 calc PR . . H1 H -0.7284 -0.2522 -0.4726 0.130 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 F1 0.123(3) 0.139(4) 0.088(2) -0.029(3) 0.0271(19) -0.017(3) F2 0.100(3) 0.115(3) 0.104(2) 0.019(3) -0.005(2) 0.024(3) F3 0.0690(18) 0.157(4) 0.0790(18) 0.011(2) 0.0119(14) -0.039(2) O1 0.087(3) 0.071(3) 0.153(4) -0.010(3) 0.073(2) -0.010(2) O2 0.089(3) 0.079(3) 0.089(2) 0.001(2) 0.0324(19) -0.020(2) O3 0.075(2) 0.105(3) 0.0677(19) 0.019(2) 0.0124(16) -0.024(2) C1 0.077(3) 0.082(4) 0.067(3) 0.006(3) 0.013(2) -0.002(3) C2 0.056(3) 0.057(3) 0.096(3) 0.013(3) 0.026(2) -0.002(2) C3 0.047(2) 0.081(4) 0.077(3) 0.015(3) 0.005(2) 0.000(2) C4 0.089(4) 0.158(8) 0.059(3) -0.007(4) 0.008(3) -0.041(5) C5 0.142(6) 0.101(6) 0.066(3) -0.015(3) 0.035(3) -0.044(5) C6 0.092(5) 0.090(7) 0.063(4) 0.000 0.019(4) 0.000 _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 F1 C1 1.326(8) . no F2 C1 1.324(8) . no F3 C1 1.321(7) . no O1 C2 1.395(5) . no O1 H1 0.8900 . no O2 C3 1.207(7) . no O3 C3 1.309(6) . no O3 C4 1.497(9) . no C1 C2 1.495(8) . no C2 C3 1.504(9) . no C2 H2 0.9800 . no C4 C5 1.449(11) . no C4 H4A 0.9700 . no C4 H4B 0.9700 . no C5 C6 1.523(9) . no C5 H5A 0.9700 . no C5 H5B 0.9700 . no C6 C5 1.523(9) 2_355 no C6 H6A 0.9700 . no C6 H6B 0.9700 . no 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 O1 H1 126.00 . . no C3 O3 C4 116.7(5) . . no F2 C1 F3 106.9(6) . . no F2 C1 F1 106.7(4) . . no F3 C1 F1 107.3(6) . . no F2 C1 C2 111.9(5) . . no F3 C1 C2 112.8(4) . . no F1 C1 C2 111.0(5) . . no O1 C2 C1 108.0(5) . . no O1 C2 C3 109.1(4) . . no C1 C2 C3 110.7(5) . . no O1 C2 H2 109.7 . . no C1 C2 H2 109.7 . . no C3 C2 H2 109.7 . . no O2 C3 O3 125.3(6) . . no O2 C3 C2 123.9(5) . . no O3 C3 C2 110.8(5) . . no C5 C4 O3 110.2(4) . . no C5 C4 H4A 109.6 . . no O3 C4 H4A 109.6 . . no C5 C4 H4B 109.6 . . no O3 C4 H4B 109.6 . . no H4A C4 H4B 108.1 . . no C4 C5 C6 116.3(7) . . no C4 C5 H5A 108.2 . . no C6 C5 H5A 108.2 . . no C4 C5 H5B 108.2 . . no C6 C5 H5B 108.2 . . no H5A C5 H5B 107.4 . . no C5 C6 C5 114.7(10) . 2_355 no C5 C6 H6A 108.6 . . no C5 C6 H6A 108.6 2_355 . no C5 C6 H6B 108.6 . . no C5 C6 H6B 108.6 2_355 . no H6A C6 H6B 107.6 . . no 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 F2 C1 C2 O1 -67.0(6) . . . . no F3 C1 C2 O1 172.4(6) . . . . no F1 C1 C2 O1 52.1(7) . . . . no F2 C1 C2 C3 52.3(6) . . . . no F3 C1 C2 C3 -68.3(7) . . . . no F1 C1 C2 C3 171.4(5) . . . . no C4 O3 C3 O2 4.7(8) . . . . no C4 O3 C3 C2 -177.0(5) . . . . no O1 C2 C3 O2 4.6(7) . . . . no C1 C2 C3 O2 -114.0(6) . . . . no O1 C2 C3 O3 -173.6(5) . . . . no C1 C2 C3 O3 67.7(6) . . . . no C3 O3 C4 C5 94.3(6) . . . . no O3 C4 C5 C6 58.5(6) . . . . no C4 C5 C6 C5 177.4(5) . . . 2_355 no _diffrn_measured_fraction_theta_max 0.882 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.882 _refine_diff_density_max 0.211 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.052 #==END #----------------------------------------------------------------------------# data_3c _database_code_depnum_ccdc_archive 'CCDC 246920' _audit_creation_method SHELXL-97 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C12 H16 F6 O6 ' _chemical_formula_moiety 'C12 H16 F6 O6 ' _chemical_formula_weight 370.25 _chemical_melting_point 387 _chemical_name_common '(S,S)-(-)-hexamethylene bis(3,3,3-trifluorolactate)' _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= -5.80 (c = 1.1, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2 ' _symmetry_Int_Tables_number 18 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 19.7519(12) _cell_length_b 5.0738(2) _cell_length_c 7.8915(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 790.86(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5322 _cell_measurement_theta_min 4.0 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 120(1) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 380 _exptl_special_details ; A needle crystal was mounted on a glass capillary. The crystal was cooled by cold nitrogen flux of a low temperature device during the data collection. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_absorpt_correction_T_min 0.749 _exptl_absorpt_correction_T_max 0.984 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 5550 _diffrn_reflns_av_R_equivalents 0.029 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1040 _reflns_number_gt 1015 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku)' _computing_cell_refinement 'PAPID-AUTO (Rigaku)' _computing_data_reduction 'teXsan Ver. 1.11 (MSC)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX Ver. 1.7 (Farrugia, 1999)' _computing_molecular_graphics 'Mercury Ver. 1.3 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # 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. H-atom of OH has been located from Fourier difference maps and fixed to its position, while the remaining H-atoms were included in calculated positions and treated as riding atoms using the SHELXL default parameters. ; _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^)+(0.0532P)^2^+0.2184P] 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_extinction_coef ? _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that of its precursor (S)-trifluorolactic acid at the chiral centre C2. This compound has no atom heavier than Si and analyzed by Mo radiation so that Flack parameter is not listed. Friedel pairs were merged before refinement. ; _refine_ls_number_reflns 1040 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0931 _refine_ls_wR_factor_gt 0.0923 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.075 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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 F1 F 0.89718(8) 1.0820(4) -0.04990(18) 0.0495(4) Uani 1 1 d . . . F2 F 0.93015(6) 1.0760(3) 0.20839(17) 0.0423(4) Uani 1 1 d . . . F3 F 0.92198(7) 0.7143(3) 0.0671(2) 0.0510(4) Uani 1 1 d . . . O1 O 0.78102(8) 0.8224(3) 0.01507(19) 0.0311(4) Uani 1 1 d . . . O2 O 0.78433(7) 0.5194(3) 0.28767(18) 0.0269(3) Uani 1 1 d . . . O3 O 0.84313(6) 0.8239(3) 0.43544(16) 0.0225(3) Uani 1 1 d . . . C1 C 0.89290(11) 0.9475(4) 0.0940(3) 0.0300(4) Uani 1 1 d . . . C2 C 0.81947(9) 0.9199(4) 0.1504(2) 0.0220(4) Uani 1 1 d . . . H2 H 0.8019 1.0925 0.1848 0.026 Uiso 1 1 calc R . . C3 C 0.81355(8) 0.7267(4) 0.2983(2) 0.0201(4) Uani 1 1 d . . . C4 C 0.84296(9) 0.6566(5) 0.5871(2) 0.0268(4) Uani 1 1 d . . . H4A H 0.8008 0.5588 0.5923 0.032 Uiso 1 1 calc R . . H4B H 0.8459 0.7665 0.6874 0.032 Uiso 1 1 calc R . . C5 C 0.90176(9) 0.4659(4) 0.5847(3) 0.0256(4) Uani 1 1 d . . . H5A H 0.8981 0.3556 0.4847 0.031 Uiso 1 1 calc R . . H5B H 0.8986 0.3521 0.6831 0.031 Uiso 1 1 calc R . . C6 C 0.97098(9) 0.5985(4) 0.5845(3) 0.0246(4) Uani 1 1 d . . . H6A H 0.9747 0.7100 0.4851 0.030 Uiso 1 1 calc R . . H6B H 0.9748 0.7102 0.6838 0.030 Uiso 1 1 calc R . . H1 H 0.7670 0.9321 -0.0500 0.047 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 F1 0.0573(8) 0.0622(10) 0.0290(7) 0.0155(7) -0.0019(6) -0.0178(9) F2 0.0306(6) 0.0651(10) 0.0311(6) 0.0023(7) -0.0035(5) -0.0190(7) F3 0.0439(7) 0.0502(9) 0.0589(10) 0.0012(9) 0.0204(7) 0.0141(7) O1 0.0412(7) 0.0204(6) 0.0316(8) 0.0020(6) -0.0203(6) -0.0017(6) O2 0.0292(6) 0.0216(6) 0.0298(7) -0.0008(6) -0.0027(6) -0.0043(6) O3 0.0250(6) 0.0233(6) 0.0193(6) -0.0015(6) -0.0020(5) 0.0005(5) C1 0.0321(9) 0.0345(11) 0.0234(9) 0.0043(9) -0.0007(7) -0.0025(9) C2 0.0248(8) 0.0177(8) 0.0235(9) -0.0008(8) -0.0073(7) 0.0006(7) C3 0.0166(7) 0.0212(8) 0.0224(8) -0.0029(7) -0.0004(6) 0.0023(6) C4 0.0261(8) 0.0354(11) 0.0189(8) 0.0031(9) 0.0022(7) -0.0011(8) C5 0.0273(9) 0.0273(9) 0.0223(8) 0.0045(8) 0.0010(7) -0.0020(8) C6 0.0261(8) 0.0247(9) 0.0231(9) -0.0002(8) 0.0011(7) -0.0001(8) #----------------------------------------------------------------------------# # 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 F1 C1 1.327(2) . no F2 C1 1.335(3) . no F3 C1 1.332(3) . no O1 C2 1.401(2) . no O1 H1 0.8100 . no O2 C3 1.203(2) . no O3 C3 1.325(2) . no O3 C4 1.467(2) . no C1 C2 1.524(3) . no C2 C3 1.528(3) . no C2 H2 0.9800 . no C4 C5 1.512(3) . no C4 H4A 0.9700 . no C4 H4B 0.9700 . no C5 C6 1.524(3) . no C5 H5A 0.9700 . no C5 H5B 0.9700 . no C6 C6 1.521(4) 2_765 no C6 H6A 0.9700 . no C6 H6B 0.9700 . no 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 O1 H1 115.00 . . no C3 O3 C4 116.74(15) . . no F1 C1 F3 107.03(18) . . no F1 C1 F2 107.00(17) . . no F3 C1 F2 107.67(19) . . no F1 C1 C2 110.99(17) . . no F3 C1 C2 112.04(18) . . no F2 C1 C2 111.84(17) . . no O1 C2 C1 109.00(16) . . no O1 C2 C3 108.32(15) . . no C1 C2 C3 110.80(15) . . no O1 C2 H2 109.6 . . no C1 C2 H2 109.6 . . no C3 C2 H2 109.6 . . no O2 C3 O3 126.42(18) . . no O2 C3 C2 122.99(17) . . no O3 C3 C2 110.57(15) . . no O3 C4 C5 110.99(14) . . no O3 C4 H4A 109.4 . . no C5 C4 H4A 109.4 . . no O3 C4 H4B 109.4 . . no C5 C4 H4B 109.4 . . no H4A C4 H4B 108.0 . . no C4 C5 C6 114.01(17) . . no C4 C5 H5A 108.7 . . no C6 C5 H5A 108.7 . . no C4 C5 H5B 108.7 . . no C6 C5 H5B 108.7 . . no H5A C5 H5B 107.6 . . no C6 C6 C5 112.7(2) 2_765 . no C6 C6 H6A 109.0 2_765 . no C5 C6 H6A 109.0 . . no C6 C6 H6B 109.0 2_765 . no C5 C6 H6B 109.0 . . no H6A C6 H6B 107.8 . . no 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 F1 C1 C2 O1 51.2(2) . . . . no F3 C1 C2 O1 -68.4(2) . . . . no F2 C1 C2 O1 170.63(16) . . . . no F1 C1 C2 C3 170.32(16) . . . . no F3 C1 C2 C3 50.7(2) . . . . no F2 C1 C2 C3 -70.3(2) . . . . no C4 O3 C3 O2 3.1(3) . . . . no C4 O3 C3 C2 -178.52(13) . . . . no O1 C2 C3 O2 5.1(2) . . . . no C1 C2 C3 O2 -114.37(19) . . . . no O1 C2 C3 O3 -173.34(14) . . . . no C1 C2 C3 O3 67.1(2) . . . . no C3 O3 C4 C5 85.1(2) . . . . no O3 C4 C5 C6 61.7(2) . . . . no C4 C5 C6 C6 179.22(12) . . . 2_765 no _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.225 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.043 #==END #----------------------------------------------------------------------------# data_3d _database_code_depnum_ccdc_archive 'CCDC 246921' _audit_creation_method SHELXL-97 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C13 H18 F6 O6 ' _chemical_formula_moiety 'C13 H18 F6 O6 ' _chemical_formula_weight 384.27 _chemical_melting_point 367 _chemical_name_common '(S,S)-(-)-heptamethylene bis(3,3,3-trifluorolactate)' _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= -4.33 (c = 1.1, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 20.8120(11) _cell_length_b 5.12790(10) _cell_length_c 7.9655(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.2790(10) _cell_angle_gamma 90.00 _cell_volume 844.99(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4678 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 296(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_special_details ; A needle crystal was mounted on a glass capillary. The data was collected under room temperature. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode ' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 3952 _diffrn_reflns_av_R_equivalents 0.0148 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1032 _reflns_number_gt 1001 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku)' _computing_cell_refinement 'PAPID-AUTO (Rigaku)' _computing_data_reduction 'teXsan Ver. 1.11 (MSC)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX Ver. 1.7 (Farrugia, 1999)' _computing_molecular_graphics 'Mercury Ver. 1.3 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # 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. Non H-atoms were refined anisotropically. The disordered alkyl chain pairs (C6C8, C5C7) was observed and refined using PART instruction of SHELXL with occupancy refinement flag. (Without the PART instruction, we could not refine the crystal structure anisotropically.) H-atoms bearing the disordered alkyl chains were included in caluculated positions and treated as riding atoms using the SHELXL default parameters. H-atom of OH has included in calculated position. The remaining H-atoms were located from Fourier difference map and fixed to its position. ; _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^)+(0.0343P)^2^+0.3997P] 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_coef 0.029(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that of its precursor (S)-trifluorolactic acid at the chiral centre C2. This compound has no atom heavier than Si and analyzed by Mo radiation so that Flack parameter is not listed. Friedel pairs were merged before refinement. ; _refine_ls_number_reflns 1032 _refine_ls_number_parameters 126 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0697 _refine_ls_wR_factor_gt 0.0691 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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 F1 F 0.10415(7) 0.1916(4) 0.40434(15) 0.0559(5) Uani 1 1 d . . . F2 F 0.06982(6) 0.2397(4) 0.64738(14) 0.0587(5) Uani 1 1 d . . . F3 F 0.09096(7) 0.5747(3) 0.50271(17) 0.0522(4) Uani 1 1 d . . . O1 O 0.22015(7) 0.4147(3) 0.50564(19) 0.0366(4) Uani 1 1 d . . . H1 H 0.2378 0.2883 0.4676 0.055 Uiso 1 1 calc R . . O2 O 0.21572(6) 0.7257(3) 0.76903(15) 0.0309(3) Uani 1 1 d . . . O3 O 0.16382(5) 0.4227(3) 0.90850(14) 0.0226(3) Uani 1 1 d . A . C1 C 0.11062(10) 0.3348(5) 0.5453(2) 0.0364(5) Uani 1 1 d . . . C2 C 0.18021(8) 0.3306(4) 0.6264(2) 0.0264(4) Uani 1 1 d . . . C3 C 0.18880(7) 0.5184(4) 0.7756(2) 0.0206(3) Uani 1 1 d . . . C4 C 0.16720(8) 0.5852(4) 1.0610(2) 0.0274(4) Uani 1 1 d D . . C5 C 0.12221(15) 0.7959(8) 1.0493(4) 0.0224(6) Uani 0.506(5) 1 d P A 1 H5A H 0.1279 0.8984 0.9496 0.027 Uiso 0.506(5) 1 calc PR A 1 H5B H 0.1314 0.9080 1.1471 0.027 Uiso 0.506(5) 1 calc PR A 1 C6 C 0.09388(16) 0.6661(8) 1.0846(4) 0.0224(6) Uani 0.502(5) 1 d P A 2 H6A H 0.0677 0.5097 1.0855 0.027 Uiso 0.502(5) 1 calc PR A 2 H6B H 0.0931 0.7524 1.1927 0.027 Uiso 0.502(5) 1 calc PR A 2 C7 C 0.05209(15) 0.7036(8) 1.0395(4) 0.0212(6) Uani 0.506(5) 1 d P A 1 H7A H 0.0451 0.6226 1.1461 0.025 Uiso 0.506(5) 1 calc PR A 1 H7B H 0.0451 0.5715 0.9523 0.025 Uiso 0.506(5) 1 calc PR A 1 C8 C 0.06478(14) 0.8459(7) 0.9454(4) 0.0212(6) Uani 0.490(5) 1 d P A 2 H8A H 0.0587 0.7547 0.8381 0.025 Uiso 0.490(5) 1 calc PR A 2 H8B H 0.0925 0.9956 0.9342 0.025 Uiso 0.490(5) 1 calc PR A 2 C9 C 0.0000 0.9305(7) 1.0000 0.0578(11) Uani 1 2 d S . . H2 H 0.1894 0.1582 0.6648 0.027 Uiso 1 1 d . . . H3 H 0.1721 0.4739 1.1566 0.043 Uiso 1 1 d . . . H4 H 0.2039 0.6916 1.0635 0.066 Uiso 1 1 d D . . H9 H 0.0042 1.0509 1.0867 0.072 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 F1 0.0787(10) 0.0592(11) 0.0320(6) -0.0185(7) 0.0158(6) -0.0252(9) F2 0.0399(6) 0.1034(15) 0.0350(6) -0.0123(8) 0.0136(5) -0.0354(9) F3 0.0497(8) 0.0584(11) 0.0458(7) -0.0068(7) -0.0072(6) 0.0155(7) O1 0.0459(8) 0.0216(8) 0.0494(8) -0.0010(6) 0.0370(6) 0.0018(6) O2 0.0337(6) 0.0301(8) 0.0297(6) 0.0034(6) 0.0076(5) -0.0138(6) O3 0.0230(5) 0.0206(7) 0.0261(5) 0.0040(5) 0.0108(4) 0.0002(5) C1 0.0421(10) 0.0434(14) 0.0255(8) -0.0103(9) 0.0120(7) -0.0118(10) C2 0.0326(8) 0.0172(9) 0.0329(8) 0.0025(7) 0.0200(7) 0.0004(7) C3 0.0143(6) 0.0202(9) 0.0282(7) 0.0065(7) 0.0060(5) 0.0012(7) C4 0.0255(8) 0.0343(12) 0.0214(7) 0.0014(7) -0.0020(6) -0.0047(8) C5 0.0212(13) 0.0258(15) 0.0214(10) -0.0017(9) 0.0079(8) -0.0015(9) C6 0.0212(13) 0.0258(15) 0.0214(10) -0.0017(9) 0.0079(8) -0.0015(9) C7 0.0207(11) 0.0189(12) 0.0250(10) 0.0026(9) 0.0068(8) -0.0002(9) C8 0.0207(11) 0.0189(12) 0.0250(10) 0.0026(9) 0.0068(8) -0.0002(9) C9 0.0337(15) 0.0131(15) 0.134(3) 0.000 0.0434(18) 0.000 #----------------------------------------------------------------------------# # 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 F1 C1 1.336(2) . no F2 C1 1.331(2) . no F3 C1 1.329(3) . no O1 C2 1.4063(19) . no O1 H1 0.8200 . no O2 C3 1.205(2) . no O3 C3 1.3237(18) . no O3 C4 1.468(2) . no C1 C2 1.520(3) . no C2 C3 1.524(2) . no C2 H2 0.9500 . no C4 C5 1.426(4) . no C4 C6 1.612(4) . no C4 H3 0.9500 . no C4 H4 0.9400 . no C5 C7 1.528(4) . no C5 H5A 0.9700 . no C5 H5B 0.9700 . no C6 C8 1.516(5) . no C6 H6A 0.9700 . no C6 H6B 0.9700 . no C7 C9 1.598(4) . no C7 H7A 0.9700 . no C7 H7B 0.9700 . no C8 C9 1.524(3) . no C8 H8A 0.9700 . no C8 H8B 0.9700 . no C9 C8 1.524(3) 2_557 no C9 C7 1.598(4) 2_557 no C9 H9 0.9200 . no 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 O1 H1 109.5 . . no C3 O3 C4 117.62(15) . . no F3 C1 F2 107.2(2) . . no F3 C1 F1 107.14(17) . . no F2 C1 F1 107.44(18) . . no F3 C1 C2 111.97(17) . . no F2 C1 C2 112.12(16) . . no F1 C1 C2 110.70(17) . . no O1 C2 C1 108.14(15) . . no O1 C2 C3 108.17(15) . . no C1 C2 C3 110.35(14) . . no O1 C2 H2 112.00 . . no C1 C2 H2 107.00 . . no C3 C2 H2 110.00 . . no O2 C3 O3 125.93(17) . . no O2 C3 C2 122.59(15) . . no O3 C3 C2 111.49(15) . . no C5 C4 O3 113.84(17) . . no O3 C4 C6 106.39(16) . . no C5 C4 H3 121.41(19) . . no O3 C4 H3 108.00 . . no C6 C4 H3 94.72(18) . . no C5 C4 H4 95.0(2) . . no O3 C4 H4 108.00 . . no C6 C4 H4 128.8(2) . . no H3 C4 H4 108.00 . . no C4 C5 C7 112.6(3) . . no C4 C5 H5A 109.1 . . no C7 C5 H5A 109.1 . . no C4 C5 H5B 109.1 . . no C7 C5 H5B 109.1 . . no H5A C5 H5B 107.8 . . no C8 C6 C4 112.3(2) . . no C8 C6 H6A 109.2 . . no C4 C6 H6A 109.2 . . no C8 C6 H6B 109.2 . . no C4 C6 H6B 109.2 . . no H6A C6 H6B 107.9 . . no C5 C7 C9 114.1(3) . . no C5 C7 H7A 108.7 . . no C9 C7 H7A 108.7 . . no C5 C7 H7B 108.7 . . no C9 C7 H7B 108.7 . . no H7A C7 H7B 107.6 . . no C6 C8 C9 105.0(2) . . no C6 C8 H8A 110.7 . . no C9 C8 H8A 110.7 . . no C6 C8 H8B 110.7 . . no C9 C8 H8B 110.7 . . no H8A C8 H8B 108.8 . . no C8 C9 C8 146.9(4) . 2_557 no C8 C9 C7 109.8(3) 2_557 . no C7 C9 C7 86.5(3) 2_557 . no C8 C9 H9 112.96(16) . . no C8 C9 H9 89.47(13) 2_557 . no C7 C9 H9 129.84(12) 2_557 . no C7 C9 H9 109.48(14) . . no 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 F3 C1 C2 O1 -64.0(2) . . . . no F2 C1 C2 O1 175.45(19) . . . . no F1 C1 C2 O1 55.5(2) . . . . no F3 C1 C2 C3 54.14(19) . . . . no F2 C1 C2 C3 -66.4(2) . . . . no F1 C1 C2 C3 173.62(17) . . . . no C4 O3 C3 O2 1.9(2) . . . . no C4 O3 C3 C2 -178.64(13) . . . . no O1 C2 C3 O2 12.9(2) . . . . no C1 C2 C3 O2 -105.23(18) . . . . no O1 C2 C3 O3 -166.56(14) . . . . no C1 C2 C3 O3 75.32(18) . . . . no C3 O3 C4 C5 75.1(2) . . . . no C3 O3 C4 C6 112.59(19) . . . . no O3 C4 C5 C7 66.8(3) . . . . no C6 C4 C5 C7 -18.3(2) . . . . no C5 C4 C6 C8 41.1(3) . . . . no O3 C4 C6 C8 -67.1(3) . . . . no C4 C5 C7 C9 -171.75(19) . . . . no C4 C6 C8 C9 -172.6(3) . . . . no C6 C8 C9 C8 -54.8(2) . . . 2_557 no C6 C8 C9 C7 -78.7(3) . . . 2_557 no C6 C8 C9 C7 -19.3(2) . . . . no C5 C7 C9 C8 40.1(3) . . . . no C5 C7 C9 C8 -159.6(2) . . . 2_557 no C5 C7 C9 C7 165.9(3) . . . 2_557 no _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.214 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.031 #==END #----------------------------------------------------------------------------# data_3e _database_code_depnum_ccdc_archive 'CCDC 246922' _audit_creation_method SHELXL-97 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common '(S,S)-(-)-octamethylene bis(3,3,3-trifluorolactate)' _chemical_melting_point 345 _chemical_formula_moiety 'C14 H20 F6 O6' _chemical_formula_sum 'C14 H20 F6 O6' _chemical_formula_weight 398.30 _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= -4.38 (c = 1.1, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_Int_Tables_number 18 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 22.9706(5) _cell_length_b 5.14600(10) _cell_length_c 8.0376(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 950.10(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 9550 _cell_measurement_theta_min 5.4 _cell_measurement_theta_max 50.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_special_details ; A platelet crystal was mounted on a glass capillary. The crystal was cooled by cold nitrogen flux of a low temperature device during the data collection. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8920 _exptl_absorpt_correction_T_max 0.9929 _exptl_absorpt_process_details ; ' (HIGASHI, T. (1995). Abscor - Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan.)' ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6670 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1053 _reflns_number_gt 990 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku)' _computing_cell_refinement 'PAPID-AUTO (Rigaku)' _computing_data_reduction 'teXsan Ver. 1.11 (MSC)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX Ver. 1.7 (Farrugia, 1999)' _computing_molecular_graphics 'Mercury Ver. 1.3 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # 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. Non H-atoms were refined anisotropically. H-atom of OH has been located from Fourier difference maps and fixed to its position, while the remaining H-atoms were included in calculated positions and treated as riding atoms using the SHELXL default parameters. ; _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^)+(0.0477P)^2^+0.1475P] 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_extinction_coef ? _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that of its precursor (S)-trifluorolactic acid at the chiral centre C2. This compound has no atom heavier than Si and analyzed by Mo radiation so that Flack parameter is not listed. Friedel pairs were merged before refinement. ; _refine_ls_number_reflns 1053 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.217 _refine_ls_restrained_S_all 1.217 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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 F1 F 0.88458(10) 0.7109(5) 0.4369(2) 0.0710(7) Uani 1 1 d . . . F2 F 0.91272(8) 0.6839(7) 0.6896(2) 0.0806(9) Uani 1 1 d . . . F3 F 0.89528(10) 0.3381(5) 0.5497(3) 0.0768(8) Uani 1 1 d . . . O1 O 0.77939(10) 0.4974(4) 0.5026(2) 0.0420(5) Uani 1 1 d . . . O2 O 0.77667(8) 0.2130(4) 0.7757(2) 0.0357(5) Uani 1 1 d . . . O3 O 0.82988(7) 0.5034(3) 0.9182(2) 0.0271(4) Uani 1 1 d . . . C1 C 0.87733(15) 0.5785(7) 0.5781(4) 0.0471(8) Uani 1 1 d . . . C2 C 0.81433(12) 0.5856(5) 0.6335(3) 0.0308(6) Uani 1 1 d . . . H2 H 0.8035 0.7642 0.6623 0.037 Uiso 1 1 calc R . . C3 C 0.80494(11) 0.4093(5) 0.7835(3) 0.0246(6) Uani 1 1 d . . . C4 C 0.82256(12) 0.3544(5) 1.0719(3) 0.0302(6) Uani 1 1 d . . . H4A H 0.7828 0.2917 1.0786 0.036 Uiso 1 1 calc R . . H4B H 0.8293 0.4674 1.1665 0.036 Uiso 1 1 calc R . . C5 C 0.86357(11) 0.1270(5) 1.0807(3) 0.0306(6) Uani 1 1 d . . . H5A H 0.8558 0.0127 0.9874 0.037 Uiso 1 1 calc R . . H5B H 0.8556 0.0304 1.1818 0.037 Uiso 1 1 calc R . . C6 C 0.92795(11) 0.2002(5) 1.0785(3) 0.0299(6) Uani 1 1 d . . . H6A H 0.9360 0.3002 0.9789 0.036 Uiso 1 1 calc R . . H6B H 0.9363 0.3098 1.1738 0.036 Uiso 1 1 calc R . . C7 C 0.96796(12) -0.0348(5) 1.0828(4) 0.0326(6) Uani 1 1 d . . . H7A H 0.9594 -0.1359 1.1817 0.039 Uiso 1 1 calc R . . H7B H 0.9598 -0.1432 0.9869 0.039 Uiso 1 1 calc R . . H10 H 0.7681 0.6183 0.4413 0.056 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 F1 0.0896(15) 0.0913(17) 0.0322(9) 0.0224(13) -0.0021(10) -0.0342(15) F2 0.0575(11) 0.147(2) 0.0369(10) 0.0138(14) -0.0087(9) -0.0501(16) F3 0.0639(13) 0.0862(17) 0.0802(17) 0.0140(15) 0.0255(13) 0.0257(14) O1 0.0603(12) 0.0299(9) 0.0358(10) 0.0061(10) -0.0258(10) 0.0017(11) O2 0.0430(11) 0.0337(10) 0.0305(10) -0.0008(9) -0.0064(9) -0.0125(10) O3 0.0350(9) 0.0233(8) 0.0230(8) -0.0029(9) -0.0046(8) 0.0000(8) C1 0.0567(19) 0.062(2) 0.0229(14) 0.0072(16) -0.0012(14) -0.0138(19) C2 0.0425(14) 0.0200(11) 0.0300(13) -0.0009(11) -0.0101(12) 0.0021(13) C3 0.0239(12) 0.0236(12) 0.0263(13) -0.0059(11) -0.0025(11) 0.0019(12) C4 0.0340(13) 0.0346(14) 0.0219(12) -0.0024(13) 0.0011(12) 0.0004(13) C5 0.0394(14) 0.0258(12) 0.0268(13) 0.0022(13) -0.0011(12) -0.0024(13) C6 0.0379(14) 0.0223(11) 0.0295(13) -0.0021(12) -0.0009(12) 0.0004(12) C7 0.0405(14) 0.0252(13) 0.0322(13) 0.0008(14) -0.0009(13) -0.0018(12) #----------------------------------------------------------------------------# # 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 F1 C1 1.334(4) . no F2 C1 1.326(4) . no F3 C1 1.324(4) . no O1 C2 1.399(3) . no O1 H10 0.8300 . no O2 C3 1.203(3) . no O3 C3 1.318(3) . no O3 C4 1.464(3) . no C1 C2 1.515(5) . no C2 C3 1.524(4) . no C2 H2 0.9800 . no C4 C5 1.504(3) . no C4 H4A 0.9700 . no C4 H4B 0.9700 . no C5 C6 1.526(4) . no C5 H5A 0.9700 . no C5 H5B 0.9700 . no C6 C7 1.519(4) . no C6 H6A 0.9700 . no C6 H6B 0.9700 . no C7 C7 1.515(5) 2_755 no C7 H7A 0.9700 . no C7 H7B 0.9700 . no 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 O1 H10 112.00 . . no C3 O3 C4 116.83(19) . . no F3 C1 F2 107.9(3) . . no F3 C1 F1 106.9(3) . . no F2 C1 F1 106.8(3) . . no F3 C1 C2 111.8(3) . . no F2 C1 C2 112.2(3) . . no F1 C1 C2 110.9(3) . . no O1 C2 C1 108.6(2) . . no O1 C2 C3 108.7(2) . . no C1 C2 C3 110.7(2) . . no O1 C2 H2 109.6 . . no C1 C2 H2 109.6 . . no C3 C2 H2 109.6 . . no O2 C3 O3 125.9(2) . . no O2 C3 C2 122.4(2) . . no O3 C3 C2 111.7(2) . . no O3 C4 C5 112.1(2) . . no O3 C4 H4A 109.2 . . no C5 C4 H4A 109.2 . . no O3 C4 H4B 109.2 . . no C5 C4 H4B 109.2 . . no H4A C4 H4B 107.9 . . no C4 C5 C6 114.5(2) . . no C4 C5 H5A 108.6 . . no C6 C5 H5A 108.6 . . no C4 C5 H5B 108.6 . . no C6 C5 H5B 108.6 . . no H5A C5 H5B 107.6 . . no C7 C6 C5 112.9(2) . . no C7 C6 H6A 109.0 . . no C5 C6 H6A 109.0 . . no C7 C6 H6B 109.0 . . no C5 C6 H6B 109.0 . . no H6A C6 H6B 107.8 . . no C7 C7 C6 113.6(3) 2_755 . no C7 C7 H7A 108.9 2_755 . no C6 C7 H7A 108.9 . . no C7 C7 H7B 108.9 2_755 . no C6 C7 H7B 108.9 . . no H7A C7 H7B 107.7 . . no 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 F3 C1 C2 O1 -64.9(3) . . . . no F2 C1 C2 O1 173.7(3) . . . . no F1 C1 C2 O1 54.3(3) . . . . no F3 C1 C2 C3 54.3(3) . . . . no F2 C1 C2 C3 -67.1(3) . . . . no F1 C1 C2 C3 173.6(2) . . . . no C4 O3 C3 O2 0.2(4) . . . . no C4 O3 C3 C2 178.42(19) . . . . no O1 C2 C3 O2 7.6(3) . . . . no C1 C2 C3 O2 -111.6(3) . . . . no O1 C2 C3 O3 -170.7(2) . . . . no C1 C2 C3 O3 70.1(3) . . . . no C3 O3 C4 C5 80.0(3) . . . . no O3 C4 C5 C6 61.2(3) . . . . no C4 C5 C6 C7 -178.4(2) . . . . no C5 C6 C7 C7 -179.30(17) . . . 2_755 no _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.29 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.214 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.049 #==END #----------------------------------------------------------------------------# data_3f_octane_solvate _database_code_depnum_ccdc_archive 'CCDC 246923' _audit_creation_method SHELXL-97 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_melting_point 322 _chemical_formula_moiety 'C15 H22 F6 O6, (C8 H18)0.28' _chemical_formula_sum 'C17.24 H27.04 F6 O6' _chemical_formula_weight 444.51 _chemical_name_common ;(S,S)-(-)-nonamethylene bis(3,3,3-trifluorolactate) octane solvate ; _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= -3.93 (c = 1.1, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 27.753(11) _cell_length_b 4.9906(10) _cell_length_c 7.992(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.942(5) _cell_angle_gamma 90.00 _cell_volume 1101.0(6) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4015 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 27.3 _cell_measurement_temperature 150(1) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 465 _exptl_special_details ; The single crystal was prepared by slow evaporation of a octane-THF solution. A needle crystal was mounted on a glass capillary. ^1^H NMR analysis of 3f crystal dissolved in CDCl~3~ showed inclusion of octane molecule. (3f[mol] : octane[mol] = 1 : 0.27) TG analysis of the crystal also showed inclusion and guest escape. (3f[mol] : octane[mol] = 1 : 0.33) In this X-ray diffraction analysis, there were four residual peaks within the void from Fourier difference map. However, the highly disordered solvents within the void were not crystallographically well defined. The SQUEEZE routine of the program PLATON estimated a void electron population to be 37 (43.2 + 2 - 8.2) per unit cell. Octane has 66 electrons per one molecule. Z value of the crystal is 2. Amount of octane in 3f crystal was calculated as follows, (3f[mol] : octane[mol] = 1 : 0.28) The calculated value from SQUEEZE result was nearly consistent with the NMR and TG results. Therefore, the octane solvate formula based on the SQUEEZE result, C15H22F6O6 + (C8H18)0.28 was adopted for calculation of the related crystallographic parameters, ; #_chemical_formula_sum 'C17.24H27.24F6O6' #_chemical_formula_moiety 'C15H22F6O6, (C8H18)0.28' #_chemical_formula_weight 444.51 #_exptl_crystal_density_diffrn 1.341 #_exptl_crystal_F_000 465 _exptl_absorpt_coefficient_mu 0.131 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# #_exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (HIGASHI, T. (1995). Abscor - Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan.) ; _exptl_absorpt_correction_T_min 0.570 _exptl_absorpt_correction_T_max 0.987 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 2928 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 25.33 _reflns_number_total 1068 _reflns_number_gt 992 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku)' _computing_cell_refinement 'PAPID-AUTO (Rigaku)' _computing_data_reduction 'teXsan Ver. 1.11 (MSC)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX Ver. 1.7 (Farrugia, 1999)' _computing_molecular_graphics 'Mercury Ver. 1.3 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # 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. Non H-atoms were refined anisotropically. H-atoms of OH have been located in calculated positions. The remaining H-atoms were included in calculated positions and treated as riding atoms using the SHELXL default parameters. ; _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^)+(0.1104P)^2^+0.2214P] 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_coef 0.014(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that of its precursor (S)-trifluorolactic acid at the chiral centre C2. This compound has no atom heavier than Si and analyzed by Mo radiation so that Flack parameter is not listed. Friedel pairs were merged before refinement. ; _refine_ls_number_reflns 1068 _refine_ls_number_parameters 125 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0496 _refine_ls_wR_factor_ref 0.1481 _refine_ls_wR_factor_gt 0.1437 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # DISORDER FIELD INFORMATION # #----------------------------------------------------------------------------# # SQUEEZE RESULTS _platon_squeeze_details ; Although there were four peaks within the void from Fourier difference map, the highly disordered solvents within the void were not crystallographically well defined. The SQUEEZE routine of the program PLATON was used in order to eliminate the contribution of disordered solvents molecules, thereby a final model based only on the ordered part of the crystal structure was obtained. The SQUEEZE routine suggested that a total potential solvent area volume of 184.2 Ang^3^[16.7% of cell volume], and a void electron population 37 per cell. Refinement after the SQUEEZE routine gave significantly improved R values. [R values before SQUEEZE] R1 = 0.103 for >2sigma(I) data R1 = 0.117 , wR2 = 0.322 , GooF = S = 1.62 for all data ( 1072 data and 0 restraint / 125 parameters) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 -0.027 0.000 92.6 21.6 2 0.500 -0.050 0.000 92.6 21.6 _platon_squeeze_details ; #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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 F1 F -0.14454(11) -0.6643(6) 0.0867(3) 0.0761(9) Uani 1 1 d . . . F2 F -0.13019(10) -0.2785(6) -0.0166(3) 0.0770(9) Uani 1 1 d . . . F3 F -0.11835(8) -0.6353(7) -0.1543(2) 0.0742(9) Uani 1 1 d . . . O1 O -0.22817(11) -0.4173(5) -0.0130(3) 0.0581(8) Uani 1 1 d . . . H1 H -0.2433 -0.5433 0.0218 0.068 Uiso 1 1 calc R . . O2 O -0.22522(8) -0.1036(5) -0.2809(3) 0.0438(6) Uani 1 1 d . . . O3 O -0.18321(7) -0.4155(5) -0.4101(2) 0.0383(6) Uani 1 1 d . . . C1 C -0.14756(15) -0.5230(8) -0.0547(4) 0.0522(9) Uani 1 1 d . . . C2 C -0.19971(12) -0.5086(7) -0.1351(4) 0.0398(7) Uani 1 1 d . . . H2 H -0.2106 -0.6874 -0.1731 0.048 Uiso 1 1 calc R . . C3 C -0.20449(9) -0.3156(7) -0.2836(4) 0.0339(6) Uani 1 1 d . . . C4 C -0.18260(11) -0.2416(8) -0.5602(3) 0.0427(8) Uani 1 1 d . . . H4A H -0.2111 -0.1282 -0.5711 0.051 Uiso 1 1 calc R . . H4B H -0.1832 -0.3516 -0.6605 0.051 Uiso 1 1 calc R . . C5 C -0.13774(10) -0.0703(8) -0.5437(3) 0.0423(8) Uani 1 1 d . . . H5A H -0.1379 0.0414 -0.4444 0.051 Uiso 1 1 calc R . . H5B H -0.1384 0.0471 -0.6407 0.051 Uiso 1 1 calc R . . C6 C -0.09108(11) -0.2336(8) -0.5305(4) 0.0437(8) Uani 1 1 d . . . H6A H -0.0909 -0.3453 -0.6297 0.052 Uiso 1 1 calc R . . H6B H -0.0903 -0.3507 -0.4333 0.052 Uiso 1 1 calc R . . C7 C -0.04583(11) -0.0577(9) -0.5141(5) 0.0526(9) Uani 1 1 d . . . H7A H -0.0463 0.0584 -0.6116 0.063 Uiso 1 1 calc R . . H7B H -0.0459 0.0547 -0.4151 0.063 Uiso 1 1 calc R . . C8 C 0.0000 -0.2264(12) -0.5000 0.0532(12) Uani 1 2 d S . . H8A H 0.0004 -0.3409 -0.4018 0.064 Uiso 0.50 1 calc PR . . H8B H -0.0004 -0.3409 -0.5982 0.064 Uiso 0.50 1 calc PR . . 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 F1 0.109(2) 0.0807(19) 0.0412(10) 0.0180(12) 0.0191(11) 0.0213(17) F2 0.0828(16) 0.0705(19) 0.0726(15) 0.0021(13) -0.0166(13) -0.0206(14) F3 0.0585(12) 0.121(2) 0.0452(10) 0.0144(13) 0.0157(9) 0.0359(15) O1 0.0798(17) 0.0364(13) 0.0677(16) 0.0008(11) 0.0540(14) 0.0017(12) O2 0.0470(11) 0.0394(13) 0.0475(11) -0.0041(10) 0.0165(9) 0.0048(9) O3 0.0360(9) 0.0464(14) 0.0343(10) -0.0044(9) 0.0129(8) 0.0040(9) C1 0.070(2) 0.052(2) 0.0355(16) 0.0061(14) 0.0103(14) 0.0061(18) C2 0.0494(15) 0.0308(16) 0.0435(15) -0.0045(12) 0.0255(13) -0.0002(13) C3 0.0274(11) 0.0389(16) 0.0370(14) -0.0072(12) 0.0113(9) -0.0031(12) C4 0.0383(14) 0.059(2) 0.0315(13) 0.0020(13) 0.0053(10) 0.0079(14) C5 0.0412(15) 0.048(2) 0.0390(14) 0.0097(14) 0.0124(11) 0.0098(14) C6 0.0393(16) 0.0459(19) 0.0476(16) 0.0010(13) 0.0134(12) 0.0061(13) C7 0.0398(16) 0.050(2) 0.071(2) 0.0057(17) 0.0195(15) 0.0021(15) C8 0.039(2) 0.056(3) 0.067(3) 0.000 0.018(2) 0.000 #----------------------------------------------------------------------------# # 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 F1 C1 1.327(4) . no F2 C1 1.336(5) . no F3 C1 1.319(4) . no O1 C2 1.394(3) . no O1 H1 0.8200 . no O2 C3 1.206(4) . no O3 C3 1.320(3) . no O3 C4 1.482(4) . no C1 C2 1.523(5) . no C2 C3 1.523(5) . no C2 H2 0.9800 . no C4 C5 1.505(5) . no C4 H4A 0.9700 . no C4 H4B 0.9700 . no C5 C6 1.524(4) . no C5 H5A 0.9700 . no C5 H5B 0.9700 . no C6 C7 1.527(5) . no C6 H6A 0.9700 . no C6 H6B 0.9700 . no C7 C8 1.520(4) . no C7 H7A 0.9700 . no C7 H7B 0.9700 . no C8 C7 1.520(4) 2_554 no C8 H8A 0.9700 . no C8 H8B 0.9700 . no 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 O1 H1 109.5 . . no C3 O3 C4 116.2(2) . . no F3 C1 F1 107.4(3) . . no F3 C1 F2 107.2(4) . . no F1 C1 F2 107.6(3) . . no F3 C1 C2 112.4(3) . . no F1 C1 C2 111.0(3) . . no F2 C1 C2 111.0(3) . . no O1 C2 C3 109.2(3) . . no O1 C2 C1 107.6(3) . . no C3 C2 C1 111.2(3) . . no O1 C2 H2 109.6 . . no C3 C2 H2 109.6 . . no C1 C2 H2 109.6 . . no O2 C3 O3 126.7(3) . . no O2 C3 C2 123.0(2) . . no O3 C3 C2 110.3(3) . . no O3 C4 C5 109.9(2) . . no O3 C4 H4A 109.7 . . no C5 C4 H4A 109.7 . . no O3 C4 H4B 109.7 . . no C5 C4 H4B 109.7 . . no H4A C4 H4B 108.2 . . no C4 C5 C6 113.0(3) . . no C4 C5 H5A 109.0 . . no C6 C5 H5A 109.0 . . no C4 C5 H5B 109.0 . . no C6 C5 H5B 109.0 . . no H5A C5 H5B 107.8 . . no C5 C6 C7 112.6(3) . . no C5 C6 H6A 109.1 . . no C7 C6 H6A 109.1 . . no C5 C6 H6B 109.1 . . no C7 C6 H6B 109.1 . . no H6A C6 H6B 107.8 . . no C8 C7 C6 111.2(3) . . no C8 C7 H7A 109.4 . . no C6 C7 H7A 109.4 . . no C8 C7 H7B 109.4 . . no C6 C7 H7B 109.4 . . no H7A C7 H7B 108.0 . . no C7 C8 C7 112.7(4) 2_554 . no C7 C8 H8A 109.1 2_554 . no C7 C8 H8A 109.1 . . no C7 C8 H8B 109.1 2_554 . no C7 C8 H8B 109.1 . . no H8A C8 H8B 107.8 . . no 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 F3 C1 C2 O1 173.0(3) . . . . no F1 C1 C2 O1 52.6(4) . . . . no F2 C1 C2 O1 -66.9(4) . . . . no F3 C1 C2 C3 -67.5(4) . . . . no F1 C1 C2 C3 172.2(3) . . . . no F2 C1 C2 C3 52.6(4) . . . . no C4 O3 C3 O2 3.6(4) . . . . no C4 O3 C3 C2 -176.6(2) . . . . no O1 C2 C3 O2 8.2(4) . . . . no C1 C2 C3 O2 -110.3(3) . . . . no O1 C2 C3 O3 -171.6(2) . . . . no C1 C2 C3 O3 69.9(3) . . . . no C3 O3 C4 C5 90.0(3) . . . . no O3 C4 C5 C6 60.8(3) . . . . no C4 C5 C6 C7 179.9(3) . . . . no C5 C6 C7 C8 179.6(2) . . . . no C6 C7 C8 C7 179.2(3) . . . 2_554 no _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.166 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.054 #==END #----------------------------------------------------------------------------# data_3g_hexane_ether_mixed_solvate _database_code_depnum_ccdc_archive 'CCDC 246924' _audit_creation_method SHELXL-97 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_melting_point 339 _chemical_formula_moiety 'C16 H24 F6 O6, (C6H14)0.30, (C4H10O)0.08' _chemical_formula_sum 'C18.12 H29 F6 O6.08' _chemical_formula_weight 458.13 _chemical_name_common ;(S,S)-(-)-decamethylene bis(3,3,3-trifluorolactate) hexane ether mixed solvate ; _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= -3.78 (c = 1.1, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2 ' _symmetry_Int_Tables_number 18 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 28.6832(8) _cell_length_b 5.0572(1) _cell_length_c 7.9245(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1149.50(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 13317 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 27.5 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 481 _exptl_special_details ; The single crystal was prepared by slow evaporation of a hexane-ether solution. A needle crystal was mounted on a glass capillary. ^1^H NMR analysis of the crystal 3g (dissolved in CDCl~3~) showed inclusion of hexane and ether. (3g[mol] : hexane[mol] : ether[mol] = 1 : 0.30 : 0.08) TG analysis of the crystal also showed inclusion and guest escape. (3g[mol] : hexane+ether[mol] = 1 : 0.35-0.40) In this X-ray diffraction analysis, there were four residual peaks within the void from Fourier difference map. However, the highly disordered solvents within the void could not be crystallographically defined. The SQUEEZE routine of the program PLATON estimated a void electron count to be 73 per unit cell. Hexane and ether have 50 and 40 electrons per one molecule, respectively. Z value of the crystal is 2. Amount of guests in 3g crystal was calculated as follows, (3g[mol] : hexane+ether[mol] = 1 : 0.71-0.89) This is larger than the results of NMR and TG analysis. The estimate by SQUEEZE may be unreliable because missing reflections can bias the estimate of the electron count by SQUEEZE. Therefore, the solvate formula based on the result of NMR analysis, C16H24F6O6, (C6H14)~0.30~(C4H10O)~0.08~ was adopted for calculation of the related crystallographic parameters, ; #_chemical_formula_sum 'C18.12H29F6O6.08' #_chemical_formula_moiety 'C16H24F6O6, (C6H14)0.3, (C4H10O)0.08' #_chemical_formula_weight 458.13 #_exptl_crystal_density_diffrn 1.324 #_exptl_crystal_F_000 481 #_exptl_absorpt_coefficient_mu 0.128 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.790 _exptl_absorpt_correction_T_max 0.987 _exptl_absorpt_process_details ; (HIGASHI, T. (1995). Abscor - Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan.) ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 2511 _diffrn_reflns_av_R_equivalents 0.0086 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1274 _reflns_number_gt 1200 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku)' _computing_cell_refinement 'PAPID-AUTO (Rigaku)' _computing_data_reduction 'teXsan Ver. 1.11 (MSC)' _computing_structure_solution 'SAPI91 (Rigaku, 1991)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX Ver. 1.7 (Farrugia, 1999)' _computing_molecular_graphics 'Mercury Ver. 1.3 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # 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. Non H-atoms were refined anisotropically. H-atoms of OH have been located from Fourier difference maps and fixed to its position. The remaining H-atoms were included in calculated positions and treated as riding atoms using the SHELXL default parameters. ; _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^)+(0.0616P)^2^+0.1844P] 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_coef 0.046(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that of its precursor (S)-trifluorolactic acid at the chiral centre C2. This compound has no atom heavier than Si and analyzed by Mo radiation so that Flack parameter is not listed. Friedel pairs were merged before refinement. ; _refine_ls_number_reflns 1274 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0949 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_restrained_S_all 1.121 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # DISORDER FIELD INFORMATION # #----------------------------------------------------------------------------# # SQUEEZE RESULTS _platon_squeeze_details ; Although there were four peaks within the void from Fourier difference map, the highly disordered solvents within the void were not crystallographically well defined. The SQUEEZE routine of the program PLATON was used in order to eliminate the contribution of disordered solvents molecules, thereby a final model based only on the ordered part of the crystal structure was obtained. The SQUEEZE routine suggested that a total potential solvent area volume of 206.9 Ang^3^[18.0% of cell volume], and a void electron population of 73 per cell. Refinement after the SQUEEZE routine gave significantly improved R values. [R values before SQUEEZE] R1 = 0.121 for >2sigma(I) data R1 = 0.142 , wR2 = 0.360, GooF = S = 1.83 for all data ( 1496 data and 0 restraint / 128 parameters) loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 -0.051 0.078 102.8 36.7 2 0.500 -0.048 -0.078 102.8 36.7 _platon_squeeze_details ; #----------------------------------------------------------------------------# # 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' O O 0.0106 0.006 '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 F1 F 0.14329(5) 0.2442(3) -0.05708(17) 0.0447(4) Uani 1 1 d . . . F2 F 0.13264(5) 0.6214(3) 0.0598(2) 0.0485(4) Uani 1 1 d . . . F3 F 0.12136(5) 0.2628(4) 0.20115(17) 0.0505(5) Uani 1 1 d . . . O1 O 0.22652(6) 0.4749(3) 0.00716(17) 0.0293(4) Uani 1 1 d . . . O2 O 0.22802(5) 0.7685(3) 0.28282(18) 0.0252(3) Uani 1 1 d . . . O3 O 0.18564(4) 0.4694(3) 0.42813(17) 0.0206(3) Uani 1 1 d . . . C1 C 0.14860(8) 0.3781(5) 0.0871(3) 0.0312(5) Uani 1 1 d . . . C2 C 0.19943(7) 0.3809(4) 0.1413(3) 0.0221(4) Uani 1 1 d . . . H2 H 0.2093 0.2016 0.1714 0.027 Uiso 1 1 calc R . . C3 C 0.20618(6) 0.5650(4) 0.2914(2) 0.0198(4) Uani 1 1 d . . . C4 C 0.18910(7) 0.6285(4) 0.5823(3) 0.0229(4) Uani 1 1 d . . . H4A H 0.2200 0.7054 0.5895 0.027 Uiso 1 1 calc R . . H4B H 0.1847 0.5152 0.6798 0.027 Uiso 1 1 calc R . . C5 C 0.15310(6) 0.8467(4) 0.5851(3) 0.0232(4) Uani 1 1 d . . . H5A H 0.1581 0.9603 0.4881 0.028 Uiso 1 1 calc R . . H5B H 0.1578 0.9528 0.6856 0.028 Uiso 1 1 calc R . . C6 C 0.10295(7) 0.7499(4) 0.5827(3) 0.0245(4) Uani 1 1 d . . . H6A H 0.0977 0.6357 0.6792 0.029 Uiso 1 1 calc R . . H6B H 0.0978 0.6461 0.4814 0.029 Uiso 1 1 calc R . . C7 C 0.06792(7) 0.9771(4) 0.5873(3) 0.0263(4) Uani 1 1 d . . . H7A H 0.0733 1.0811 0.6884 0.032 Uiso 1 1 calc R . . H7B H 0.0732 1.0910 0.4907 0.032 Uiso 1 1 calc R . . C8 C 0.01740(6) 0.8849(4) 0.5855(3) 0.0272(5) Uani 1 1 d . . . H8A H 0.0118 0.7751 0.6838 0.033 Uiso 1 1 calc R . . H8B H 0.0122 0.7772 0.4860 0.033 Uiso 1 1 calc R . . H1 H 0.2397 0.3546 -0.0484 0.050 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 F1 0.0575(8) 0.0559(9) 0.0207(6) -0.0135(7) 0.0006(6) -0.0173(8) F2 0.0409(7) 0.0493(8) 0.0552(10) -0.0090(8) -0.0158(7) 0.0134(6) F3 0.0428(7) 0.0853(12) 0.0233(7) -0.0060(8) 0.0065(6) -0.0325(8) O1 0.0412(8) 0.0228(7) 0.0237(7) -0.0014(7) 0.0182(6) 0.0001(6) O2 0.0289(7) 0.0242(7) 0.0226(7) 0.0020(6) 0.0032(6) -0.0072(6) O3 0.0265(6) 0.0193(6) 0.0159(6) 0.0003(6) 0.0033(6) -0.0011(5) C1 0.0357(11) 0.0395(12) 0.0183(9) -0.0063(10) 0.0030(9) -0.0075(10) C2 0.0299(10) 0.0176(9) 0.0188(9) 0.0011(8) 0.0082(8) 0.0004(8) C3 0.0204(8) 0.0214(9) 0.0176(9) 0.0031(8) 0.0010(8) 0.0022(7) C4 0.0260(9) 0.0277(10) 0.0149(8) -0.0033(8) -0.0007(8) -0.0014(8) C5 0.0276(9) 0.0223(9) 0.0198(9) -0.0043(9) 0.0023(8) -0.0023(8) C6 0.0265(9) 0.0211(10) 0.0259(9) -0.0005(9) 0.0018(8) -0.0003(8) C7 0.0285(10) 0.0223(9) 0.0279(10) -0.0028(10) 0.0023(8) 0.0010(8) C8 0.0273(9) 0.0209(9) 0.0336(11) -0.0004(9) -0.0001(9) -0.0007(8) #----------------------------------------------------------------------------# # 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 F1 C1 1.337(3) . no F2 C1 1.330(3) . no F3 C1 1.330(3) . no O1 C2 1.399(2) . no O1 H1 0.8400 . no O2 C3 1.206(2) . no O3 C3 1.325(2) . no O3 C4 1.466(2) . no C1 C2 1.520(3) . no C2 C3 1.523(3) . no C2 H2 0.9800 . no C4 C5 1.511(3) . no C4 H4A 0.9700 . no C4 H4B 0.9700 . no C5 C6 1.520(3) . no C5 H5A 0.9700 . no C5 H5B 0.9700 . no C6 C7 1.527(3) . no C6 H6A 0.9700 . no C6 H6B 0.9700 . no C7 C8 1.522(3) . no C7 H7A 0.9700 . no C7 H7B 0.9700 . no C8 C8 1.533(4) 2_575 no C8 H8A 0.9700 . no C8 H8B 0.9700 . no 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 O1 H1 114.00 . . no C3 O3 C4 116.82(14) . . no F3 C1 F2 108.3(2) . . no F3 C1 F1 106.97(17) . . no F2 C1 F1 106.88(19) . . no F3 C1 C2 112.08(19) . . no F2 C1 C2 111.55(18) . . no F1 C1 C2 110.84(18) . . no O1 C2 C1 108.73(17) . . no O1 C2 C3 108.37(15) . . no C1 C2 C3 110.39(16) . . no O1 C2 H2 109.8 . . no C1 C2 H2 109.8 . . no C3 C2 H2 109.8 . . no O2 C3 O3 126.03(18) . . no O2 C3 C2 122.90(17) . . no O3 C3 C2 111.06(15) . . no O3 C4 C5 111.50(15) . . no O3 C4 H4A 109.3 . . no C5 C4 H4A 109.3 . . no O3 C4 H4B 109.3 . . no C5 C4 H4B 109.3 . . no H4A C4 H4B 108.0 . . no C4 C5 C6 114.27(16) . . no C4 C5 H5A 108.7 . . no C6 C5 H5A 108.7 . . no C4 C5 H5B 108.7 . . no C6 C5 H5B 108.7 . . no H5A C5 H5B 107.6 . . no C5 C6 C7 112.33(16) . . no C5 C6 H6A 109.1 . . no C7 C6 H6A 109.1 . . no C5 C6 H6B 109.1 . . no C7 C6 H6B 109.1 . . no H6A C6 H6B 107.9 . . no C8 C7 C6 113.30(17) . . no C8 C7 H7A 108.9 . . no C6 C7 H7A 108.9 . . no C8 C7 H7B 108.9 . . no C6 C7 H7B 108.9 . . no H7A C7 H7B 107.7 . . no C7 C8 C8 112.8(2) . 2_575 no C7 C8 H8A 109.0 . . no C8 C8 H8A 109.0 2_575 . no C7 C8 H8B 109.0 . . no C8 C8 H8B 109.0 2_575 . no H8A C8 H8B 107.8 . . no 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 F3 C1 C2 O1 172.82(17) . . . . no F2 C1 C2 O1 -65.6(2) . . . . no F1 C1 C2 O1 53.4(2) . . . . no F3 C1 C2 C3 -68.4(2) . . . . no F2 C1 C2 C3 53.2(2) . . . . no F1 C1 C2 C3 172.14(16) . . . . no C4 O3 C3 O2 1.2(3) . . . . no C4 O3 C3 C2 -179.54(14) . . . . no O1 C2 C3 O2 6.5(3) . . . . no C1 C2 C3 O2 -112.5(2) . . . . no O1 C2 C3 O3 -172.78(15) . . . . no C1 C2 C3 O3 68.2(2) . . . . no C3 O3 C4 C5 82.0(2) . . . . no O3 C4 C5 C6 61.7(2) . . . . no C4 C5 C6 C7 179.44(17) . . . . no C5 C6 C7 C8 -179.86(19) . . . . no C6 C7 C8 C8 -178.48(12) . . . 2_575 no _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.191 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.054 #==END