# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_section_title ; A binary hydrogen bonding system based on homochiral recognition: Crystal structures and hydrogen bonding networks of meso-(R,S)-bis(trifluorolactate)s ; _publ_contact_author_name 'Dr Toshimasa Katagiri' _publ_contact_author_address ; Applied Chemistry Okayama University Tsushimanaka 3-1-1 Okayama 700-8530 JAPAN ; _publ_contact_author_email TKATA@CC.OKAYAMA-U.AC.JP _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. WinGX - Farrugia, L. J. (1999) J. Appl. Cryst. 32, 837. PLATON/PLUTON - Spek, A. L. (1990) Acta Cryst. A46, C34. SQUEEZE - Sluis, P. v.d. & Spek, A. L. (1990) Acta Cryst. A46, 194. MERCURY - Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M. K.; Macrae, C. F.; McCabe, P.; Pearson J.; Taylor, R. (2002) Acta Cryst. B58, 389. ; loop_ _publ_author_name 'Satoshi Takahashi' 'Toshimasa Katagiri' 'Kenji Uneyama' data_RS-1a #------------------------------------------------------------------------------ _database_code_depnum_ccdc_archive 'CCDC 246911' _audit_creation_date 'Sat Jun 12 10:38:46 2004' _audit_creation_method 'by the program teXsan' _audit_update_record ; 2005-2-25 Checkcif 2005-5-8 Checkcif ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C10 H12 F6 O6 ' _chemical_formula_moiety 'C10 H12 F6 O6 ' _chemical_formula_weight 342.19 _chemical_melting_point 366 _chemical_name_common Tetramethylene-(R,S)-(+-)-bis(3,3,3-trifluorolactate) _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= 0 (c = 1.0, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 7.1113(8) _cell_length_b 5.0864(3) _cell_length_c 18.142(2) _cell_angle_alpha 90 _cell_angle_beta 98.398(2) _cell_angle_gamma 90 _cell_volume 649.17(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4418 _cell_measurement_theta_min 4.2 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 120(1) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_F_000 348 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.750 _exptl_crystal_density_method 'not measured' #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.193 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (HIGASHI, T., Rigaku (1995)' _exptl_absorpt_correction_T_min 0.699 _exptl_absorpt_correction_T_max 0.981 _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. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_ambient_temperature 120(1) _diffrn_measurement_method \w _diffrn_reflns_number 2819 _reflns_number_total 1487 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_theta_max 27.5 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.85 _diffrn_measured_fraction_theta_full 0.991 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 #----------------------------------------------------------------------------# # 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 'SIR97 (Altomare et al., 1999)' _computing_publication_material 'teXsan Ver. 1.11 (MSC)' _computing_molecular_graphics 'Mercury Ver. 1.3 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). All H-atoms has been located from Fourier difference maps and refined isotropically. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _reflns_number_gt 1043 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_R_factor_gt 0.0448 _refine_ls_R_factor_all 0.0536 _refine_ls_wR_factor_ref 0.1160 _refine_ls_goodness_of_fit_ref 1.397 _refine_ls_number_reflns 1247 _refine_ls_number_parameters 124 _refine_ls_weighting_scheme calc _refine_ls_hydrogen_treatment refall _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.06000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0005 _refine_diff_density_max 0.24 _refine_diff_density_min -0.36 _refine_ls_extinction_method none #----------------------------------------------------------------------------# # 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F(1) F 1.0887(2) -0.0349(3) 0.38816(7) 0.0388(4) Uani 1.00 d . . . F(2) F 0.8255(2) -0.0445(3) 0.43242(7) 0.0385(4) Uani 1.00 d . . . F(3) F 0.9837(2) 0.3172(3) 0.43392(7) 0.0344(3) Uani 1.00 d . . . O(1) O 0.9589(2) 0.2678(3) 0.27327(8) 0.0323(4) Uani 1.00 d . . . O(2) O 0.6642(2) 0.5826(3) 0.28369(7) 0.0283(4) Uani 1.00 d . . . O(3) O 0.5753(2) 0.3286(3) 0.37443(7) 0.0259(4) Uani 1.00 d . . . C(1) C 0.9302(3) 0.1023(4) 0.3936(1) 0.0254(5) Uani 1.00 d . . . C(2) C 0.8263(3) 0.1736(3) 0.3169(1) 0.0227(5) Uani 1.00 d . . . C(3) C 0.6790(3) 0.3879(4) 0.32228(10) 0.0215(4) Uani 1.00 d . . . C(4) C 0.4355(3) 0.5208(5) 0.3925(1) 0.0302(5) Uani 1.00 d . . . C(5) C 0.4108(3) 0.4700(5) 0.4726(1) 0.0318(6) Uani 1.00 d . . . H(1) H 1.018(5) 0.134(7) 0.254(2) 0.056(8) Uiso 1.00 d . . . H(2) H 0.766(4) 0.020(5) 0.297(1) 0.035(6) Uiso 1.00 d . . . H(3) H 0.489(4) 0.696(5) 0.385(1) 0.038(7) Uiso 1.00 d . . . H(4) H 0.313(5) 0.480(5) 0.361(2) 0.050(8) Uiso 1.00 d . . . H(5) H 0.305(4) 0.602(5) 0.483(1) 0.035(6) Uiso 1.00 d . . . H(6) H 0.370(4) 0.292(5) 0.478(2) 0.048(8) Uiso 1.00 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F(1) 0.0436(8) 0.0445(7) 0.0292(7) 0.0162(6) 0.0089(6) 0.0011(5) F(2) 0.0457(8) 0.0459(7) 0.0247(6) -0.0044(6) 0.0077(6) 0.0179(5) F(3) 0.0289(7) 0.0439(7) 0.0296(6) -0.0026(6) 0.0019(5) -0.0153(5) O(1) 0.052(1) 0.0225(6) 0.0289(8) 0.0065(7) 0.0280(7) 0.0049(6) O(2) 0.0430(9) 0.0208(6) 0.0236(7) 0.0004(6) 0.0135(6) 0.0029(5) O(3) 0.0282(8) 0.0322(7) 0.0189(7) -0.0026(6) 0.0092(6) 0.0039(5) C(1) 0.030(1) 0.0277(9) 0.0197(9) -0.0001(9) 0.0080(8) -0.0015(8) C(2) 0.038(1) 0.0168(8) 0.0155(8) -0.0036(8) 0.0094(8) 0.0001(7) C(3) 0.031(1) 0.0210(8) 0.0133(8) -0.0073(8) 0.0055(7) -0.0022(7) C(4) 0.023(1) 0.049(1) 0.0200(9) 0.0015(10) 0.0050(8) -0.0001(9) C(5) 0.020(1) 0.057(1) 0.0194(10) -0.006(1) 0.0054(8) -0.0010(9) #----------------------------------------------------------------------------# # 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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F(1) C(1) 1.342(2) . . no F(2) C(1) 1.327(2) . . no F(3) C(1) 1.339(2) . . no O(1) C(2) 1.401(2) . . no O(1) H(1) 0.90(4) . . no O(2) C(3) 1.208(2) . . no O(3) C(3) 1.317(2) . . no O(3) C(4) 1.465(3) . . no C(1) C(2) 1.521(3) . . no C(2) C(3) 1.525(3) . . no C(2) H(2) 0.94(3) . . no C(4) C(5) 1.511(3) . . no C(4) H(3) 0.99(3) . . no C(4) H(4) 0.99(3) . . no C(5) C(5) 1.525(4) . 3_666 no C(5) H(5) 1.05(3) . . no C(5) H(6) 0.96(3) . . 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(2) O(1) H(1) 110(2) . . . no C(3) O(3) C(4) 118.5(2) . . . no F(1) C(1) F(2) 106.8(2) . . . no F(1) C(1) F(3) 106.8(2) . . . no F(1) C(1) C(2) 111.0(2) . . . no F(2) C(1) F(3) 107.8(1) . . . no F(2) C(1) C(2) 112.6(2) . . . no F(3) C(1) C(2) 111.5(2) . . . no O(1) C(2) C(1) 108.7(2) . . . no O(1) C(2) C(3) 108.5(1) . . . no O(1) C(2) H(2) 112(1) . . . no C(1) C(2) C(3) 111.0(1) . . . no C(1) C(2) H(2) 106(1) . . . no C(3) C(2) H(2) 109(1) . . . no O(2) C(3) O(3) 126.4(2) . . . no O(2) C(3) C(2) 123.4(2) . . . no O(3) C(3) C(2) 110.2(2) . . . no O(3) C(4) C(5) 106.2(2) . . . no O(3) C(4) H(3) 106(1) . . . no O(3) C(4) H(4) 107(1) . . . no C(5) C(4) H(3) 113(1) . . . no C(5) C(4) H(4) 107(1) . . . no H(3) C(4) H(4) 115(2) . . . no C(4) C(5) C(5) 113.0(2) . . 3_666 no C(4) C(5) H(5) 104(1) . . . no C(4) C(5) H(6) 109(1) . . . no C(5) C(5) H(5) 107(1) 3_666 . . no C(5) C(5) H(6) 110(1) 3_666 . . no H(5) C(5) H(6) 110(2) . . . 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 F(1) C(1) C(2) O(1) -45.4(2) . . . . no F(1) C(1) C(2) C(3) -164.7(2) . . . . no F(2) C(1) C(2) O(1) -165.1(1) . . . . no F(2) C(1) C(2) C(3) 75.7(2) . . . . no F(3) C(1) C(2) O(1) 73.5(2) . . . . no F(3) C(1) C(2) C(3) -45.7(2) . . . . no O(1) C(2) C(3) O(2) 12.2(3) . . . . no O(1) C(2) C(3) O(3) -167.3(2) . . . . no O(2) C(3) O(3) C(4) -4.5(3) . . . . no O(2) C(3) C(2) C(1) 131.6(2) . . . . no O(3) C(3) C(2) C(1) -47.9(2) . . . . no O(3) C(4) C(5) C(5) 66.2(3) . . . 3_666 no C(2) C(3) O(3) C(4) 175.1(2) . . . . no C(3) O(3) C(4) C(5) -153.2(2) . . . . no C(4) C(5) C(5) C(4) 180.0 . . 3_666 3_666 no C(4) C(5) C(5) C(4) 180.0 . . 3_666 3_666 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag F(1) H(5) 2.82(3) . 1_645 no F(1) H(6) 2.91(3) . 1_655 no F(2) H(6) 2.61(3) . 3_656 no F(2) H(3) 2.76(3) . 1_545 no F(3) H(5) 2.74(3) . 1_655 no F(3) H(6) 2.75(3) . 1_655 no F(3) H(4) 2.97(3) . 1_655 no O(1) O(1) 2.769(1) . 2_755 no O(1) O(1) 2.769(1) . 2_745 no O(1) O(2) 3.154(2) . 2_745 no O(1) C(2) 3.162(2) . 2_755 no O(2) C(2) 3.244(2) . 1_565 no #==END #------------------------------------------------------------------------------ data_RS-1b _database_code_depnum_ccdc_archive 'CCDC 246912' _audit_creation_date 2005-05-08T18:00:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common Pentamethylene-(R,S)-(+-)-bis(3,3,3-trifluorolactate) _chemical_formula_sum 'C11 H14 F6 O6 ' _chemical_formula_moiety 'C11 H14 F6 O6 ' _chemical_formula_weight 356.22 _chemical_melting_point 340 _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= 0 (c = 1.0, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 15.40(1) _cell_length_b 18.79(2) _cell_length_c 5.045(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1460(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8186 _cell_measurement_theta_min 1.1 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 120(1) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 1.000 _exptl_crystal_size_mid 0.060 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.62 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _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 0.175 _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 0.512 _exptl_absorpt_correction_T_max 0.997 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(1) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_reflns_number 6719 _diffrn_reflns_av_R_equivalents 0.073 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 25.5 _diffrn_measured_fraction_theta_full 0.863 _diffrn_measured_fraction_theta_max 0.887 _reflns_number_total 2218 _reflns_number_gt 1002 _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 their 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^)+(0.0340P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.0078(15) _refine_ls_number_reflns 2218 _refine_ls_number_parameters 209 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1391 _refine_ls_R_factor_gt 0.0567 _refine_ls_wR_factor_ref 0.132 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 0.869 _refine_ls_restrained_S_all 0.868 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.317 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.078 #----------------------------------------------------------------------------# # 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 0.2811(3) 0.3574(3) 0.5961(10) 0.0508(14) Uani 1 1 d . . . F2 F 0.2148(3) 0.3202(2) 0.2438(10) 0.0444(12) Uani 1 1 d . . . F3 F 0.1427(2) 0.3433(2) 0.5998(9) 0.0433(13) Uani 1 1 d . . . F4 F 0.1211(3) 0.1875(2) 0.5235(9) 0.0467(13) Uani 1 1 d . . . F5 F 0.2007(3) 0.1712(2) 0.1766(11) 0.0538(15) Uani 1 1 d . . . F6 F 0.2405(3) 0.1296(3) 0.5529(10) 0.0504(14) Uani 1 1 d . . . O1 O 0.2792(3) 0.4673(3) 0.2542(10) 0.0348(14) Uani 1 1 d . . . O2 O 0.1401(3) 0.4868(3) -0.0477(10) 0.0377(14) Uani 1 1 d . . . O3 O 0.0590(3) 0.4126(3) 0.2018(11) 0.0332(13) Uani 1 1 d . . . O4 O 0.0060(3) 0.1350(3) 0.1682(9) 0.0314(13) Uani 1 1 d . . . O5 O 0.0551(3) 0.0423(3) -0.0682(10) 0.0388(15) Uani 1 1 d . . . O6 O 0.1854(3) 0.0210(3) 0.2473(10) 0.0386(15) Uani 1 1 d . . . C1 C 0.2092(5) 0.3657(4) 0.4443(18) 0.0355(19) Uani 1 1 d . . . C2 C 0.1995(4) 0.4410(4) 0.3682(15) 0.033(2) Uani 1 1 d . . . H2 H 0.1838 0.4696 0.5236 0.039 Uiso 1 1 calc R . . C3 C 0.1291(5) 0.4493(4) 0.1487(17) 0.0313(19) Uani 1 1 d . . . C4 C -0.0125(4) 0.4166(4) 0.0150(14) 0.0274(18) Uani 1 1 d . . . H4 H 0.0093 0.4146 -0.1652 0.033 Uiso 1 1 calc R . . H3 H -0.0436 0.4611 0.0377 0.033 Uiso 1 1 calc R . . C5 C -0.0720(4) 0.3553(4) 0.0653(18) 0.036(2) Uani 1 1 d . . . H5 H -0.124 0.3613 -0.0407 0.043 Uiso 1 1 calc R . . H6 H -0.0891 0.3558 0.2503 0.043 Uiso 1 1 calc R . . C6 C -0.0312(4) 0.2824(4) 0.0006(19) 0.037(2) Uani 1 1 d . . . H7 H -0.0119 0.282 -0.1824 0.044 Uiso 1 1 calc R . . H8 H 0.019 0.2747 0.1129 0.044 Uiso 1 1 calc R . . C7 C -0.0956(5) 0.2233(4) 0.0434(17) 0.035(2) Uani 1 1 d . . . H10 H -0.1133 0.2235 0.228 0.042 Uiso 1 1 calc R . . H9 H -0.1468 0.2328 -0.0631 0.042 Uiso 1 1 calc R . . C8 C -0.0621(5) 0.1513(4) -0.0244(16) 0.041(2) Uani 1 1 d . . . H11 H -0.1083 0.1164 -0.014 0.049 Uiso 1 1 calc R . . H12 H -0.0387 0.151 -0.2028 0.049 Uiso 1 1 calc R . . C9 C 0.0572(5) 0.0827(4) 0.1245(16) 0.0321(19) Uani 1 1 d . . . C10 C 0.1241(5) 0.0718(4) 0.3303(17) 0.031(2) Uani 1 1 d . . . H13 H 0.0959 0.0547 0.4925 0.037 Uiso 1 1 calc R . . C11 C 0.1713(5) 0.1399(5) 0.3905(17) 0.040(2) Uani 1 1 d . . . H1 H 0.3105 0.4815 0.4205 0.065 Uiso 1 1 d . . . H14 H 0.2139 0.0073 0.4226 0.065 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 0.030(2) 0.059(3) 0.063(4) 0.017(3) -0.030(2) -0.005(2) F2 0.025(2) 0.032(2) 0.077(3) -0.007(3) 0.000(3) 0.003(2) F3 0.032(2) 0.042(3) 0.056(3) 0.014(2) 0.005(2) -0.008(2) F4 0.038(2) 0.041(3) 0.060(3) -0.019(2) -0.011(3) 0.008(2) F5 0.036(3) 0.047(3) 0.079(4) 0.005(3) 0.010(2) -0.011(2) F6 0.038(2) 0.058(3) 0.055(4) -0.015(3) -0.020(3) 0.005(3) O1 0.023(3) 0.052(3) 0.029(3) -0.001(3) 0.001(2) -0.010(3) O2 0.027(3) 0.053(4) 0.033(3) 0.009(3) -0.002(2) -0.013(3) O3 0.021(2) 0.035(3) 0.044(4) 0.010(3) -0.002(3) -0.014(3) O4 0.029(3) 0.037(3) 0.029(3) -0.004(2) -0.005(2) 0.005(3) O5 0.026(3) 0.053(4) 0.038(4) 0.004(3) -0.001(3) -0.004(3) O6 0.040(3) 0.044(3) 0.032(3) -0.006(3) -0.005(3) 0.017(3) C1 0.023(4) 0.037(5) 0.046(5) 0.003(4) 0.000(4) 0.012(4) C2 0.022(4) 0.043(5) 0.033(5) 0.009(4) -0.005(4) -0.005(4) C3 0.030(4) 0.031(4) 0.033(5) -0.006(4) 0.001(4) 0.003(4) C4 0.014(3) 0.046(5) 0.022(5) -0.010(4) 0.000(3) 0.007(4) C5 0.013(3) 0.053(5) 0.041(5) -0.008(4) -0.008(4) -0.013(4) C6 0.013(3) 0.040(5) 0.057(6) -0.003(4) 0.002(4) 0.004(4) C7 0.023(4) 0.039(5) 0.043(5) 0.006(4) 0.006(4) -0.002(4) C8 0.028(4) 0.052(6) 0.043(6) 0.008(4) -0.006(4) -0.008(4) C9 0.034(4) 0.025(4) 0.037(6) 0.007(4) 0.001(4) -0.003(4) C10 0.024(4) 0.031(4) 0.036(5) 0.004(4) 0.007(4) 0.002(4) C11 0.024(4) 0.050(5) 0.047(7) -0.005(5) 0.000(4) 0.003(5) #----------------------------------------------------------------------------# # 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 1.355(9) . no F2 C1 1.328(9) . no F3 C1 1.357(9) . no F4 C11 1.360(9) . no F5 C11 1.310(10) . no F6 C11 1.358(9) . no O1 C2 1.443(8) . no O1 H1 1.003(5) . no O2 C3 1.227(9) . no O3 C3 1.308(8) . no O3 C4 1.452(8) . no O4 C9 1.281(8) . no O4 C8 1.462(8) . no O5 C9 1.234(9) . no O6 C10 1.406(8) . no O6 H14 1.021(5) . no C1 C2 1.474(10) . no C2 C3 1.558(10) . no C2 H2 0.98 . no C4 C5 1.493(10) . no C4 H4 0.97 . no C4 H3 0.97 . no C5 C6 1.543(10) . no C5 H5 0.97 . no C5 H6 0.97 . no C6 C7 1.504(10) . no C6 H7 0.97 . no C6 H8 0.97 . no C7 C8 1.488(10) . no C7 H10 0.97 . no C7 H9 0.97 . no C8 H11 0.97 . no C8 H12 0.97 . no C9 C10 1.477(11) . no C10 C11 1.504(11) . no C10 H13 0.98 . 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 99.6(5) . . no C3 O3 C4 117.8(6) . . no C9 O4 C8 119.2(6) . . no C10 O6 H14 101.7(5) . . no F2 C1 F1 107.7(6) . . no F2 C1 F3 106.8(6) . . no F1 C1 F3 104.7(7) . . no F2 C1 C2 115.3(7) . . no F1 C1 C2 109.9(7) . . no F3 C1 C2 111.8(6) . . no O1 C2 C1 110.2(6) . . no O1 C2 C3 106.0(6) . . no C1 C2 C3 110.6(7) . . no O1 C2 H2 110 . . no C1 C2 H2 110 . . no C3 C2 H2 110 . . no O2 C3 O3 125.6(7) . . no O2 C3 C2 122.3(7) . . no O3 C3 C2 112.1(7) . . no O3 C4 C5 108.4(6) . . no O3 C4 H4 110 . . no C5 C4 H4 110 . . no O3 C4 H3 110 . . no C5 C4 H3 110 . . no H4 C4 H3 108.4 . . no C4 C5 C6 113.6(6) . . no C4 C5 H5 108.8 . . no C6 C5 H5 108.8 . . no C4 C5 H6 108.8 . . no C6 C5 H6 108.8 . . no H5 C5 H6 107.7 . . no C7 C6 C5 110.9(6) . . no C7 C6 H7 109.5 . . no C5 C6 H7 109.5 . . no C7 C6 H8 109.5 . . no C5 C6 H8 109.5 . . no H7 C6 H8 108 . . no C8 C7 C6 114.1(6) . . no C8 C7 H10 108.7 . . no C6 C7 H10 108.7 . . no C8 C7 H9 108.7 . . no C6 C7 H9 108.7 . . no H10 C7 H9 107.6 . . no O4 C8 C7 106.7(6) . . no O4 C8 H11 110.4 . . no C7 C8 H11 110.4 . . no O4 C8 H12 110.4 . . no C7 C8 H12 110.4 . . no H11 C8 H12 108.6 . . no O5 C9 O4 126.3(7) . . no O5 C9 C10 119.2(7) . . no O4 C9 C10 114.5(7) . . no O6 C10 C9 110.7(7) . . no O6 C10 C11 108.2(6) . . no C9 C10 C11 111.2(7) . . no O6 C10 H13 108.9 . . no C9 C10 H13 108.9 . . no C11 C10 H13 108.9 . . no F5 C11 F6 106.9(7) . . no F5 C11 F4 107.9(7) . . no F6 C11 F4 104.1(7) . . no F5 C11 C10 112.5(7) . . no F6 C11 C10 112.3(7) . . no F4 C11 C10 112.6(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 F2 C1 C2 O1 -70.3(8) . . . . no F1 C1 C2 O1 51.6(9) . . . . no F3 C1 C2 O1 167.5(6) . . . . no F2 C1 C2 C3 46.5(9) . . . . no F1 C1 C2 C3 168.4(6) . . . . no F3 C1 C2 C3 -75.7(9) . . . . no C4 O3 C3 O2 -0.6(11) . . . . no C4 O3 C3 C2 178.9(6) . . . . no O1 C2 C3 O2 -15.5(10) . . . . no C1 C2 C3 O2 -134.9(7) . . . . no O1 C2 C3 O3 165.0(6) . . . . no C1 C2 C3 O3 45.5(9) . . . . no C3 O3 C4 C5 162.4(6) . . . . no O3 C4 C5 C6 -66.7(8) . . . . no C4 C5 C6 C7 -177.4(7) . . . . no C5 C6 C7 C8 177.9(7) . . . . no C9 O4 C8 C7 -166.3(6) . . . . no C6 C7 C8 O4 67.1(8) . . . . no C8 O4 C9 O5 -0.9(11) . . . . no C8 O4 C9 C10 179.2(6) . . . . no O5 C9 C10 O6 9.3(10) . . . . no O4 C9 C10 O6 -170.7(6) . . . . no O5 C9 C10 C11 129.7(7) . . . . no O4 C9 C10 C11 -50.4(9) . . . . no O6 C10 C11 F5 70.5(8) . . . . no C9 C10 C11 F5 -51.3(9) . . . . no O6 C10 C11 F6 -50.1(9) . . . . no C9 C10 C11 F6 -171.9(6) . . . . no O6 C10 C11 F4 -167.2(6) . . . . no C9 C10 C11 F4 71.0(9) . . . . no #==END #------------------------------------------------------------------------------ data_RS-1c _database_code_depnum_ccdc_archive 'CCDC 246913' _audit_creation_date 'Sat Feb 26 18:40:57 2005' _audit_creation_method 'by the program teXsan' _audit_update_record ;2005-2-26 Checkcif ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C12 H16 F6 O6 ' _chemical_formula_moiety 'C12 H16 F6 O6 ' _chemical_formula_weight 370.24 _chemical_melting_point 386 _chemical_name_common Hexamethylene-(R,S)-(+-)-bis(3,3,3-trifluorolactate) _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= 0 (c = 1.0, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y,1/2-z -x,-y,-z x,-y,1/2+z 1/2+x,1/2+y,z 1/2-x,1/2+y,1/2-z 1/2-x,1/2-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 19.891(2) _cell_length_b 5.1138(2) _cell_length_c 15.605(1) _cell_angle_alpha 90 _cell_angle_beta 100.918(1) _cell_angle_gamma 90 _cell_volume 1558.6(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4443 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 120(1) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_F_000 760 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.167 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (HIGASHI, T., Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.782 _exptl_absorpt_correction_T_max 0.992 _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. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _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_ambient_temperature 120(1) _diffrn_reflns_number 5843 _reflns_number_total 1679 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_theta_max 27.5 _diffrn_measured_fraction_theta_max 0.9375 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.9528 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 #----------------------------------------------------------------------------# # 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 'SIR97 (Altomare et al., 1999)' _computing_publication_material 'teXsan Ver. 1.11 (MSC)' _computing_molecular_graphics 'Mercury Ver. 1.3 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). All H-atoms has been located from Fourier difference maps. H-atoms of the alcohol function were fixed to its position. The remaining H-atoms were refined isotropically. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _reflns_number_gt 1283 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_R_factor_gt 0.0356 _refine_ls_R_factor_all 0.0375 _refine_ls_wR_factor_ref 0.1273 _refine_ls_number_reflns 1371 _refine_ls_number_parameters 137 _refine_ls_goodness_of_fit_ref 1.251 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.09600(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0004 _refine_diff_density_max 0.25 _refine_diff_density_min -0.26 _refine_ls_extinction_method none #----------------------------------------------------------------------------# # 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F(1) F 0.39778(5) -0.0237(2) 0.80213(6) 0.0375(3) Uani 1.00 d . . . F(2) F 0.42101(5) 0.3617(2) 0.76132(7) 0.0399(3) Uani 1.00 d . . . F(3) F 0.43146(5) 0.0293(2) 0.68055(6) 0.0386(3) Uani 1.00 d . . . O(1) O 0.28074(5) 0.2574(2) 0.74843(7) 0.0270(3) Uani 1.00 d . . . O(2) O 0.28624(5) 0.5726(2) 0.61619(6) 0.0243(3) Uani 1.00 d . . . O(3) O 0.33572(4) 0.2641(2) 0.54612(6) 0.0203(3) Uani 1.00 d . . . C(1) C 0.39280(7) 0.1328(3) 0.73261(9) 0.0248(4) Uani 1.00 d . . . C(2) C 0.31820(6) 0.1645(2) 0.68749(8) 0.0195(3) Uani 1.00 d . . . C(3) C 0.31174(6) 0.3616(2) 0.61300(8) 0.0174(3) Uani 1.00 d . . . C(4) C 0.33742(7) 0.4432(3) 0.47293(9) 0.0231(4) Uani 1.00 d . . . C(5) C 0.40403(7) 0.5943(3) 0.48853(8) 0.0222(4) Uani 1.00 d . . . C(6) C 0.46691(6) 0.4224(3) 0.49196(9) 0.0229(4) Uani 1.00 d . . . H(1) H 0.2624 0.1235 0.7720 0.0409 Uiso 1.00 d . . . H(2) H 0.3070(9) -0.012(4) 0.667(1) 0.028(4) Uiso 1.00 d . . . H(3) H 0.2977(9) 0.560(3) 0.467(1) 0.026(4) Uiso 1.00 d . . . H(4) H 0.3339(8) 0.324(3) 0.426(1) 0.021(4) Uiso 1.00 d . . . H(5) H 0.4023(9) 0.718(4) 0.443(1) 0.026(4) Uiso 1.00 d . . . H(6) H 0.4067(9) 0.683(3) 0.538(1) 0.025(4) Uiso 1.00 d . . . H(7) H 0.4650(9) 0.337(4) 0.438(1) 0.034(5) Uiso 1.00 d . . . H(8) H 0.4693(9) 0.295(4) 0.532(1) 0.034(4) Uiso 1.00 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F(1) 0.0446(6) 0.0420(6) 0.0260(5) 0.0104(4) 0.0071(4) 0.0096(4) F(2) 0.0323(6) 0.0415(6) 0.0417(6) -0.0112(4) -0.0037(4) -0.0057(4) F(3) 0.0275(5) 0.0626(7) 0.0272(6) 0.0194(4) 0.0094(4) 0.0004(4) O(1) 0.0332(6) 0.0198(5) 0.0353(6) 0.0009(4) 0.0252(5) 0.0030(4) O(2) 0.0305(6) 0.0203(6) 0.0243(5) 0.0039(4) 0.0107(4) -0.0015(4) O(3) 0.0188(5) 0.0221(6) 0.0225(5) -0.0015(3) 0.0102(4) -0.0027(3) C(1) 0.0260(8) 0.0291(7) 0.0201(7) 0.0022(5) 0.0069(5) -0.0012(5) C(2) 0.0203(7) 0.0165(7) 0.0239(7) -0.0012(4) 0.0097(5) -0.0021(5) C(3) 0.0136(6) 0.0179(7) 0.0219(7) -0.0038(4) 0.0064(5) -0.0035(5) C(4) 0.0193(7) 0.0343(8) 0.0166(7) -0.0007(5) 0.0053(5) -0.0001(5) C(5) 0.0213(7) 0.0278(7) 0.0191(7) -0.0020(5) 0.0082(5) 0.0014(5) C(6) 0.0189(8) 0.0279(7) 0.0241(7) -0.0039(5) 0.0093(5) -0.0024(5) #----------------------------------------------------------------------------# # 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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F(1) C(1) 1.337(2) . . no F(2) C(1) 1.338(2) . . no F(3) C(1) 1.329(2) . . no O(1) C(2) 1.398(2) . . no O(1) H(1) 0.887 . . no O(2) C(3) 1.197(2) . . no O(3) C(3) 1.324(2) . . no O(3) C(4) 1.469(2) . . no C(1) C(2) 1.526(2) . . no C(2) C(3) 1.526(2) . . no C(2) H(2) 0.97(2) . . no C(4) C(5) 1.513(2) . . no C(4) H(3) 0.98(2) . . no C(4) H(4) 0.95(2) . . no C(5) C(6) 1.521(2) . . no C(5) H(5) 0.95(2) . . no C(5) H(6) 0.89(2) . . no C(6) C(6) 1.517(2) . 3_666 no C(6) H(7) 0.95(2) . . no C(6) H(8) 0.90(2) . . 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(2) O(1) H(1) 109.5 . . . no C(3) O(3) C(4) 116.28(10) . . . no F(1) C(1) F(2) 106.9(1) . . . no F(1) C(1) F(3) 107.2(1) . . . no F(1) C(1) C(2) 110.7(1) . . . no F(2) C(1) F(3) 107.4(1) . . . no F(2) C(1) C(2) 111.8(1) . . . no F(3) C(1) C(2) 112.6(1) . . . no O(1) C(2) C(1) 108.6(1) . . . no O(1) C(2) C(3) 108.35(10) . . . no O(1) C(2) H(2) 115(1) . . . no C(1) C(2) C(3) 110.85(10) . . . no C(1) C(2) H(2) 101(1) . . . no C(3) C(2) H(2) 112(1) . . . no O(2) C(3) O(3) 126.2(1) . . . no O(2) C(3) C(2) 122.6(1) . . . no O(3) C(3) C(2) 111.1(1) . . . no O(3) C(4) C(5) 110.0(1) . . . no O(3) C(4) H(3) 108(1) . . . no O(3) C(4) H(4) 101.1(10) . . . no C(5) C(4) H(3) 111.6(10) . . . no C(5) C(4) H(4) 112.8(10) . . . no H(3) C(4) H(4) 112(1) . . . no C(4) C(5) C(6) 113.6(1) . . . no C(4) C(5) H(5) 108(1) . . . no C(4) C(5) H(6) 107(1) . . . no C(6) C(5) H(5) 108(1) . . . no C(6) C(5) H(6) 110(1) . . . no H(5) C(5) H(6) 107(1) . . . no C(5) C(6) C(6) 112.7(1) . . 3_666 no C(5) C(6) H(7) 110(1) . . . no C(5) C(6) H(8) 112(1) . . . no C(6) C(6) H(7) 106(1) 3_666 . . no C(6) C(6) H(8) 109(1) 3_666 . . no H(7) C(6) H(8) 105(1) . . . 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 F(1) C(1) C(2) O(1) 56.1(1) . . . . no F(1) C(1) C(2) C(3) 175.0(1) . . . . no F(2) C(1) C(2) O(1) -63.0(1) . . . . no F(2) C(1) C(2) C(3) 56.0(1) . . . . no F(3) C(1) C(2) O(1) 176.1(1) . . . . no F(3) C(1) C(2) C(3) -65.0(1) . . . . no O(1) C(2) C(3) O(2) 9.2(2) . . . . no O(1) C(2) C(3) O(3) -168.84(10) . . . . no O(2) C(3) O(3) C(4) 6.7(2) . . . . no O(2) C(3) C(2) C(1) -109.9(1) . . . . no O(3) C(3) C(2) C(1) 72.1(1) . . . . no O(3) C(4) C(5) C(6) 63.5(1) . . . . no C(2) C(3) O(3) C(4) -175.25(9) . . . . no C(3) O(3) C(4) C(5) 87.6(1) . . . . no C(4) C(5) C(6) C(6) -179.7(1) . . . 3_666 no C(5) C(6) C(6) C(5) -180.0 . . 3_666 3_666 no C(5) C(6) C(6) C(5) -180.0 . . 3_666 3_666 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) H(2) 2.66(2) . 6_556 no O(1) O(1) 2.8386(8) . 6_556 no O(1) O(1) 2.8386(8) . 6_546 no O(1) O(2) 2.863(1) . 6_546 no O(1) C(2) 3.155(2) . 6_556 no O(1) H(4) 3.23(2) . 7_556 no O(2) H(3) 2.68(2) . 7_566 no O(2) H(4) 3.11(2) . 7_556 no O(2) C(2) 3.246(2) . 1_565 no C(4) H(2) 3.28(2) . 7_556 no #==END #------------------------------------------------------------------------------ data_RS-1d _database_code_depnum_ccdc_archive 'CCDC 246914' _audit_creation_date 'Sat Feb 26 19:40:27 2005' _audit_creation_method 'by the program teXsan' _audit_update_record ;2005-2-26 Checkcif ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_sum 'C13 H18 F6 O6 ' _chemical_formula_moiety 'C13 H18 F6 O6 ' _chemical_formula_weight 384.27 _chemical_melting_point 368 _chemical_name_common Heptamethylene-(R,S)-(+-)-bis(3,3,3-trifluorolactate) _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= 0 (c = 1.0, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M ' P n m a ' _symmetry_Int_Tables_number 62 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,1/2-y,1/2-z -x,1/2+y,-z 1/2-x,-y,1/2+z -x,-y,-z 1/2-x,1/2+y,1/2+z x,1/2-y,z 1/2+x,y,1/2-z _cell_length_a 15.613(3) _cell_length_b 21.793(4) _cell_length_c 5.0901(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1731(1) _cell_formula_units_Z 4 _cell_measurement_reflns_used 12495 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 120(1) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_F_000 792 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.030 _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (HIGASHI, T., Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.871 _exptl_absorpt_correction_T_max 0.995 _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. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_ambient_temperature 120(1) _diffrn_reflns_number 10363 _reflns_number_total 1888 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_theta_max 27.5 _diffrn_measured_fraction_theta_max 0.9214 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.9477 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 #----------------------------------------------------------------------------# # 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 'SIR97 (Altomare et al., 1999)' _computing_publication_material 'teXsan Ver. 1.11 (MSC)' _computing_molecular_graphics 'Mercury Ver. 1.3 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). All H-atoms has been located from Fourier difference maps. H-atoms of the alcohol function were fixed to its position. The remaining H-atoms were refined isotropically. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _reflns_number_gt 836 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_R_factor_gt 0.0506 _refine_ls_R_factor_all 0.0976 _refine_ls_wR_factor_ref 0.1395 _refine_ls_hydrogen_treatment mixed _refine_ls_number_reflns 1541 _refine_ls_number_parameters 149 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0001 _refine_diff_density_max 0.54 _refine_diff_density_min -0.54 _refine_ls_extinction_method none #----------------------------------------------------------------------------# # 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F(1) F 0.7654(2) 0.1360(1) 0.7664(5) 0.0448(8) Uani 1.00 d . . . F(2) F 0.7198(2) 0.1541(1) 0.3755(5) 0.0470(8) Uani 1.00 d . . . F(3) F 0.6359(2) 0.1651(1) 0.7067(5) 0.0467(8) Uani 1.00 d . . . O(1) O 0.7420(2) 0.0294(2) 0.4932(5) 0.0345(9) Uani 1.00 d . . . O(2) O 0.6085(2) 0.0317(1) 0.1733(5) 0.0261(8) Uani 1.00 d . . . O(3) O 0.5257(1) 0.0770(1) 0.4815(4) 0.0229(7) Uani 1.00 d . . . C(1) C 0.6979(3) 0.1296(2) 0.6061(9) 0.033(1) Uani 1.00 d . . . C(2) C 0.6715(3) 0.0638(2) 0.5827(8) 0.027(1) Uani 1.00 d . . . C(3) C 0.5989(2) 0.0557(2) 0.3861(7) 0.024(1) Uani 1.00 d . . . C(4) C 0.4521(3) 0.0764(2) 0.3013(8) 0.024(1) Uani 1.00 d . . . C(5) C 0.4520(3) 0.1333(2) 0.1343(8) 0.024(1) Uani 1.00 d . . . C(6) C 0.4418(3) 0.1920(2) 0.2918(8) 0.027(1) Uani 1.00 d . . . C(7) C 0.4472(4) 0.2500 0.123(1) 0.026(2) Uani 1.00 d S . . H(1) H 0.7687 0.0156 0.6176 0.0649 Uiso 1.00 d . . . H(2) H 0.653(3) 0.052(2) 0.757(8) 0.04(1) Uiso 1.00 d . . . H(3) H 0.456(3) 0.042(2) 0.200(7) 0.02(1) Uiso 1.00 d . . . H(4) H 0.403(3) 0.078(2) 0.408(9) 0.05(1) Uiso 1.00 d . . . H(5) H 0.406(3) 0.131(2) 0.010(7) 0.03(1) Uiso 1.00 d . . . H(6) H 0.506(3) 0.140(2) 0.038(6) 0.022(9) Uiso 1.00 d . . . H(7) H 0.383(2) 0.191(2) 0.388(7) 0.022(9) Uiso 1.00 d . . . H(8) H 0.486(2) 0.195(2) 0.424(7) 0.016(9) Uiso 1.00 d . . . H(9) H 0.398(5) 0.2500 -0.01(1) 0.06(1) Uiso 1.00 d S . . H(10) H 0.501(3) 0.2500 0.033(8) 0.01(1) Uiso 1.00 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F(1) 0.025(1) 0.061(2) 0.048(1) -0.004(1) -0.006(1) -0.016(1) F(2) 0.051(2) 0.044(2) 0.046(1) -0.014(1) 0.002(1) 0.013(1) F(3) 0.027(1) 0.039(2) 0.074(2) 0.000(1) 0.004(1) -0.023(2) O(1) 0.029(1) 0.046(2) 0.028(2) 0.021(2) -0.003(1) -0.001(1) O(2) 0.025(1) 0.034(2) 0.019(1) 0.004(1) 0.004(1) -0.004(1) O(3) 0.018(1) 0.026(2) 0.025(1) 0.003(1) 0.002(1) -0.003(1) C(1) 0.019(2) 0.043(3) 0.037(2) 0.000(2) 0.004(2) -0.002(2) C(2) 0.023(2) 0.030(3) 0.027(2) 0.006(2) 0.004(2) 0.002(2) C(3) 0.020(2) 0.021(3) 0.032(2) 0.001(2) 0.008(2) 0.007(2) C(4) 0.018(2) 0.026(3) 0.029(2) 0.000(2) 0.002(2) -0.004(2) C(5) 0.020(2) 0.023(3) 0.029(2) -0.001(2) -0.003(2) -0.002(2) C(6) 0.026(2) 0.021(3) 0.034(2) 0.000(2) 0.001(2) -0.004(2) C(7) 0.028(3) 0.022(4) 0.029(3) 0.0000 0.004(3) 0.0000 #----------------------------------------------------------------------------# # 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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F(1) C(1) 1.339(5) . . no F(2) C(1) 1.334(5) . . no F(3) C(1) 1.340(5) . . no O(1) C(2) 1.406(5) . . no O(1) H(1) 0.816 . . no O(2) C(3) 1.213(4) . . no O(3) C(3) 1.326(4) . . no O(3) C(4) 1.470(5) . . no C(1) C(2) 1.498(7) . . no C(2) C(3) 1.523(6) . . no C(2) H(2) 0.97(4) . . no C(4) C(5) 1.504(6) . . no C(4) H(3) 0.91(4) . . no C(4) H(4) 0.94(5) . . no C(5) C(6) 1.516(6) . . no C(5) H(5) 0.96(4) . . no C(5) H(6) 0.98(4) . . no C(6) C(7) 1.531(5) . . no C(6) H(7) 1.04(4) . . no C(6) H(8) 0.97(4) . . no C(7) H(9) 1.02(7) . . no C(7) H(10) 0.96(5) . . 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(2) O(1) H(1) 110.2 . . . no C(3) O(3) C(4) 116.2(3) . . . no F(1) C(1) F(2) 107.0(3) . . . no F(1) C(1) F(3) 106.0(4) . . . no F(1) C(1) C(2) 111.4(4) . . . no F(2) C(1) F(3) 106.9(4) . . . no F(2) C(1) C(2) 112.5(4) . . . no F(3) C(1) C(2) 112.6(3) . . . no O(1) C(2) C(1) 108.7(3) . . . no O(1) C(2) C(3) 108.0(3) . . . no O(1) C(2) H(2) 113(2) . . . no C(1) C(2) C(3) 111.6(4) . . . no C(1) C(2) H(2) 105(2) . . . no C(3) C(2) H(2) 110(2) . . . no O(2) C(3) O(3) 125.8(4) . . . no O(2) C(3) C(2) 123.0(3) . . . no O(3) C(3) C(2) 111.2(3) . . . no O(3) C(4) C(5) 110.2(4) . . . no O(3) C(4) H(3) 107(2) . . . no O(3) C(4) H(4) 106(2) . . . no C(5) C(4) H(3) 111(2) . . . no C(5) C(4) H(4) 107(3) . . . no H(3) C(4) H(4) 114(3) . . . no C(4) C(5) C(6) 113.3(3) . . . no C(4) C(5) H(5) 109(2) . . . no C(4) C(5) H(6) 113(2) . . . no C(6) C(5) H(5) 107(2) . . . no C(6) C(5) H(6) 103(2) . . . no H(5) C(5) H(6) 108(2) . . . no C(5) C(6) C(7) 113.2(3) . . . no C(5) C(6) H(7) 108(2) . . . no C(5) C(6) H(8) 110(2) . . . no C(7) C(6) H(7) 109(2) . . . no C(7) C(6) H(8) 106(2) . . . no H(7) C(6) H(8) 107(2) . . . no C(6) C(7) C(6) 111.4(5) . . 7_555 no C(6) C(7) H(9) 108(1) . . . no C(6) C(7) H(10) 108(1) . . . no C(6) C(7) H(9) 108(1) 7_555 . . no C(6) C(7) H(10) 108(1) 7_555 . . no H(9) C(7) H(10) 110(4) . . . 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 F(1) C(1) C(2) O(1) -57.1(4) . . . . no F(1) C(1) C(2) C(3) -176.0(3) . . . . no F(2) C(1) C(2) O(1) 63.1(4) . . . . no F(2) C(1) C(2) C(3) -55.9(4) . . . . no F(3) C(1) C(2) O(1) -176.0(3) . . . . no F(3) C(1) C(2) C(3) 65.1(5) . . . . no O(1) C(2) C(3) O(2) -10.6(6) . . . . no O(1) C(2) C(3) O(3) 168.1(3) . . . . no O(2) C(3) O(3) C(4) -6.2(6) . . . . no O(2) C(3) C(2) C(1) 108.8(4) . . . . no O(3) C(3) C(2) C(1) -72.5(4) . . . . no O(3) C(4) C(5) C(6) -63.0(4) . . . . no C(2) C(3) O(3) C(4) 175.2(3) . . . . no C(3) O(3) C(4) C(5) -85.2(4) . . . . no C(4) C(5) C(6) C(7) 176.5(4) . . . . no C(5) C(6) C(7) C(6) -176.7(3) . . . 7_555 no C(5) C(6) C(7) C(6) -176.7(3) . . . 7_555 no #==END #------------------------------------------------------------------------------ data_RS-1e _database_code_depnum_ccdc_archive 'CCDC 246915' _audit_creation_date 2005-05-08T17:07:39-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common Octamethylene-(R,S)-(+-)-bis(3,3,3-trifluorolactate) _chemical_formula_sum 'C14 H20 F6 O6 ' _chemical_formula_moiety 'C14 H20 F6 O6 ' _chemical_formula_weight 398.30 _chemical_melting_point 358 _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= 0 (c = 1.0, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1196(11) _cell_length_b 10.895(3) _cell_length_c 17.165(4) _cell_angle_alpha 72.489(7) _cell_angle_beta 89.576(15) _cell_angle_gamma 85.41(2) _cell_volume 910.0(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3836 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 120(1) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.100 _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _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 0.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (HIGASHI, T., Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.640 _exptl_absorpt_correction_T_max 0.985 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(1) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_reflns_number 4258 _diffrn_reflns_av_R_equivalents 0.030 _diffrn_reflns_av_unetI/netI 0.0212 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.5 _diffrn_measured_fraction_theta_full 0.752 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_max 0.769 _reflns_number_total 2601 _reflns_number_gt 2135 _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. 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^)+(0.1585P)^2^+1.8590P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.008(8) _refine_ls_number_reflns 2601 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0963 _refine_ls_R_factor_gt 0.0851 _refine_ls_wR_factor_ref 0.2687 _refine_ls_wR_factor_gt 0.2618 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.546 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.124 #----------------------------------------------------------------------------# # 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 0.7267(8) -1.0763(4) 1.32323(19) 0.0595(11) Uani 1 1 d . . . F2 F 0.3573(8) -0.9657(4) 1.2822(2) 0.0576(10) Uani 1 1 d . . . F3 F 0.7051(7) -0.9193(3) 1.21214(18) 0.0467(9) Uani 1 1 d . . . F4 F 0.2051(10) -0.5137(4) 1.1912(2) 0.0707(13) Uani 1 1 d . . . F5 F -0.1610(9) -0.5811(4) 1.2395(2) 0.0663(12) Uani 1 1 d . . . F6 F 0.1981(9) -0.6705(3) 1.3019(2) 0.0572(11) Uani 1 1 d . . . O1 O 0.4272(7) -1.2225(3) 1.2659(2) 0.0327(9) Uani 1 1 d . . . O2 O 0.1176(7) -1.1036(3) 1.13930(18) 0.0308(8) Uani 1 1 d . . . O3 O 0.3902(7) -0.9485(3) 1.09171(18) 0.0292(8) Uani 1 1 d . . . O4 O -0.0400(7) -0.3395(3) 1.2575(2) 0.0394(9) Uani 1 1 d . . . O5 O -0.3415(7) -0.4445(3) 1.38232(18) 0.0296(8) Uani 1 1 d . . . O6 O -0.0259(6) -0.6041(3) 1.43611(17) 0.0236(7) Uani 1 1 d . . . C1 C 0.5770(12) -1.0172(5) 1.2568(3) 0.0374(13) Uani 1 1 d . . . C2 C 0.5216(10) -1.1124(4) 1.2114(3) 0.0271(10) Uani 1 1 d . . . H2 H 0.6842 -1.1373 1.1875 0.032 Uiso 1 1 calc R . . C3 C 0.3155(9) -1.0546(4) 1.1435(2) 0.0239(9) Uani 1 1 d . . . C4 C 0.2074(11) -0.8833(4) 1.0235(3) 0.0313(11) Uani 1 1 d . . . H4 H 0.0371 -0.8635 1.0439 0.038 Uiso 1 1 calc R . . H3 H 0.1865 -0.9379 0.989 0.038 Uiso 1 1 calc R . . C5 C 0.3243(11) -0.7615(5) 0.9764(3) 0.0331(12) Uani 1 1 d . . . H5 H 0.2178 -0.7203 0.9276 0.04 Uiso 1 1 calc R . . H6 H 0.4978 -0.7838 0.9591 0.04 Uiso 1 1 calc R . . C6 C 0.3463(12) -0.6651(5) 1.0241(3) 0.0349(12) Uani 1 1 d . . . H8 H 0.1719 -0.6365 1.0374 0.042 Uiso 1 1 calc R . . H7 H 0.4412 -0.7077 1.075 0.042 Uiso 1 1 calc R . . C7 C 0.4855(11) -0.5485(4) 0.9767(3) 0.0338(12) Uani 1 1 d . . . H9 H 0.3888 -0.5057 0.9261 0.041 Uiso 1 1 calc R . . H10 H 0.6583 -0.5777 0.9625 0.041 Uiso 1 1 calc R . . C8 C 0.0743(13) -0.5578(6) 1.2604(3) 0.0439(14) Uani 1 1 d . . . C9 C 0.0570(10) -0.4596(4) 1.3082(3) 0.0288(10) Uani 1 1 d . . . H12 H 0.2318 -0.4531 1.3288 0.035 Uiso 1 1 calc R . . C10 C -0.1282(9) -0.5013(4) 1.3801(2) 0.0221(9) Uani 1 1 d . . . C11 C -0.1891(9) -0.6579(4) 1.5075(2) 0.0236(10) Uani 1 1 d . . . H13 H -0.2836 -0.5878 1.5225 0.028 Uiso 1 1 calc R . . H14 H -0.0771 -0.7071 1.5535 0.028 Uiso 1 1 calc R . . C12 C -0.3815(9) -0.7437(4) 1.4897(3) 0.0263(10) Uani 1 1 d . . . H15 H -0.5092 -0.6907 1.4497 0.032 Uiso 1 1 calc R . . H16 H -0.4747 -0.7822 1.5394 0.032 Uiso 1 1 calc R . . C13 C -0.2592(9) -0.8520(4) 1.4578(3) 0.0265(10) Uani 1 1 d . . . H17 H -0.3975 -0.9024 1.4489 0.032 Uiso 1 1 calc R . . H18 H -0.1813 -0.8133 1.4053 0.032 Uiso 1 1 calc R . . C14 C -0.0506(9) -0.9428(4) 1.5142(2) 0.0255(10) Uani 1 1 d . . . H19 H 0.0959 -0.8941 1.5188 0.031 Uiso 1 1 calc R . . H20 H -0.1232 -0.9752 1.5682 0.031 Uiso 1 1 calc R . . H1 H 0.5805 -1.2891 1.2778 0.03 Uiso 1 1 d . . . H11 H -0.0043 -0.2502 1.2387 0.037 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 0.072(3) 0.067(2) 0.0330(16) 0.0014(15) -0.0283(17) -0.0258(18) F2 0.066(3) 0.071(2) 0.0454(18) -0.0328(17) 0.0066(17) -0.0038(18) F3 0.063(2) 0.0418(18) 0.0349(15) -0.0056(12) -0.0113(15) -0.0259(15) F4 0.089(4) 0.086(3) 0.0304(17) -0.0079(16) 0.0313(18) -0.008(2) F5 0.072(3) 0.093(3) 0.047(2) -0.0366(19) -0.0068(18) -0.025(2) F6 0.081(3) 0.046(2) 0.0413(17) -0.0133(14) 0.0221(17) 0.0086(17) O1 0.023(2) 0.0312(18) 0.0342(17) 0.0055(13) -0.0046(14) -0.0054(13) O2 0.030(2) 0.0358(18) 0.0239(15) -0.0026(12) -0.0026(13) -0.0116(13) O3 0.032(2) 0.0309(17) 0.0208(14) 0.0003(12) -0.0078(13) -0.0108(13) O4 0.028(2) 0.0340(19) 0.0412(19) 0.0112(14) -0.0028(15) -0.0055(13) O5 0.026(2) 0.0318(18) 0.0263(15) -0.0031(12) -0.0028(13) 0.0005(13) O6 0.0229(19) 0.0242(16) 0.0217(14) -0.0035(11) 0.0005(12) -0.0033(11) C1 0.052(4) 0.034(3) 0.024(2) -0.0043(18) -0.011(2) -0.010(2) C2 0.028(3) 0.026(2) 0.024(2) -0.0006(16) -0.0024(18) -0.0062(17) C3 0.027(3) 0.024(2) 0.0194(19) -0.0049(15) 0.0017(17) -0.0051(17) C4 0.037(3) 0.032(2) 0.022(2) -0.0003(17) -0.0133(19) -0.0086(19) C5 0.045(3) 0.034(3) 0.019(2) -0.0034(17) -0.0053(19) -0.012(2) C6 0.051(4) 0.029(3) 0.023(2) -0.0040(18) 0.000(2) -0.012(2) C7 0.048(3) 0.029(2) 0.023(2) -0.0051(18) 0.001(2) -0.011(2) C8 0.053(4) 0.054(3) 0.021(2) -0.005(2) 0.012(2) -0.008(2) C9 0.028(3) 0.028(2) 0.026(2) 0.0009(17) -0.0009(18) -0.0058(17) C10 0.019(3) 0.026(2) 0.021(2) -0.0049(16) -0.0017(16) -0.0050(16) C11 0.025(3) 0.027(2) 0.0176(18) -0.0043(15) 0.0012(16) -0.0017(16) C12 0.019(3) 0.033(2) 0.024(2) -0.0034(16) 0.0017(17) -0.0037(17) C13 0.028(3) 0.028(2) 0.023(2) -0.0064(16) -0.0045(17) -0.0067(17) C14 0.030(3) 0.024(2) 0.0223(19) -0.0054(16) -0.0032(17) -0.0054(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.340(6) . no F2 C1 1.345(7) . no F3 C1 1.330(6) . no F4 C8 1.336(6) . no F5 C8 1.324(8) . no F6 C8 1.331(7) . no O1 C2 1.400(5) . no O1 H1 1.003(3) . no O2 C3 1.194(6) . no O3 C3 1.312(5) . no O3 C4 1.469(5) . no O4 C9 1.391(5) . no O4 H11 0.961(3) . no O5 C10 1.218(6) . no O6 C10 1.311(5) . no O6 C11 1.475(5) . no C1 C2 1.517(7) . no C2 C3 1.529(6) . no C2 H2 0.98 . no C4 C5 1.498(6) . no C4 H4 0.97 . no C4 H3 0.97 . no C5 C6 1.525(7) . no C5 H5 0.97 . no C5 H6 0.97 . no C6 C7 1.516(6) . no C6 H8 0.97 . no C6 H7 0.97 . no C7 C7 1.523(9) 2_647 no C7 H9 0.97 . no C7 H10 0.97 . no C8 C9 1.530(7) . no C9 C10 1.531(6) . no C9 H12 0.98 . no C11 C12 1.504(6) . no C11 H13 0.97 . no C11 H14 0.97 . no C12 C13 1.533(6) . no C12 H15 0.97 . no C12 H16 0.97 . no C13 C14 1.526(6) . no C13 H17 0.97 . no C13 H18 0.97 . no C14 C14 1.522(9) 2_538 no C14 H19 0.97 . no C14 H20 0.97 . 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 104.9(3) . . no C3 O3 C4 116.0(4) . . no C9 O4 H11 142.6(4) . . no C10 O6 C11 116.5(3) . . no F3 C1 F1 106.6(4) . . no F3 C1 F2 106.9(4) . . no F1 C1 F2 107.1(4) . . no F3 C1 C2 113.0(4) . . no F1 C1 C2 110.2(4) . . no F2 C1 C2 112.6(4) . . no O1 C2 C1 109.5(4) . . no O1 C2 C3 108.1(4) . . no C1 C2 C3 111.5(4) . . no O1 C2 H2 109.2 . . no C1 C2 H2 109.2 . . no C3 C2 H2 109.2 . . no O2 C3 O3 126.2(4) . . no O2 C3 C2 123.0(4) . . no O3 C3 C2 110.8(4) . . no O3 C4 C5 106.5(4) . . no O3 C4 H4 110.4 . . no C5 C4 H4 110.4 . . no O3 C4 H3 110.4 . . no C5 C4 H3 110.4 . . no H4 C4 H3 108.6 . . no C4 C5 C6 114.1(4) . . no C4 C5 H5 108.7 . . no C6 C5 H5 108.7 . . no C4 C5 H6 108.7 . . no C6 C5 H6 108.7 . . no H5 C5 H6 107.6 . . no C7 C6 C5 112.3(4) . . no C7 C6 H8 109.1 . . no C5 C6 H8 109.1 . . no C7 C6 H7 109.1 . . no C5 C6 H7 109.1 . . no H8 C6 H7 107.9 . . no C6 C7 C7 113.5(5) . 2_647 no C6 C7 H9 108.9 . . no C7 C7 H9 108.9 2_647 . no C6 C7 H10 108.9 . . no C7 C7 H10 108.9 2_647 . no H9 C7 H10 107.7 . . no F5 C8 F6 107.6(5) . . no F5 C8 F4 106.9(5) . . no F6 C8 F4 106.8(5) . . no F5 C8 C9 111.6(5) . . no F6 C8 C9 112.9(4) . . no F4 C8 C9 110.7(5) . . no O4 C9 C8 109.7(4) . . no O4 C9 C10 108.4(4) . . no C8 C9 C10 110.3(4) . . no O4 C9 H12 109.5 . . no C8 C9 H12 109.5 . . no C10 C9 H12 109.5 . . no O5 C10 O6 126.4(4) . . no O5 C10 C9 122.7(4) . . no O6 C10 C9 110.9(4) . . no O6 C11 C12 111.3(3) . . no O6 C11 H13 109.4 . . no C12 C11 H13 109.4 . . no O6 C11 H14 109.4 . . no C12 C11 H14 109.4 . . no H13 C11 H14 108 . . no C11 C12 C13 114.7(4) . . no C11 C12 H15 108.6 . . no C13 C12 H15 108.6 . . no C11 C12 H16 108.6 . . no C13 C12 H16 108.6 . . no H15 C12 H16 107.6 . . no C14 C13 C12 114.6(3) . . no C14 C13 H17 108.6 . . no C12 C13 H17 108.6 . . no C14 C13 H18 108.6 . . no C12 C13 H18 108.6 . . no H17 C13 H18 107.6 . . no C14 C14 C13 114.1(4) 2_538 . no C14 C14 H19 108.7 2_538 . no C13 C14 H19 108.7 . . no C14 C14 H20 108.7 2_538 . no C13 C14 H20 108.7 . . no H19 C14 H20 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 F3 C1 C2 O1 170.1(4) . . . . no F1 C1 C2 O1 51.0(6) . . . . no F2 C1 C2 O1 -68.6(5) . . . . no F3 C1 C2 C3 -70.3(6) . . . . no F1 C1 C2 C3 170.6(4) . . . . no F2 C1 C2 C3 51.0(5) . . . . no C4 O3 C3 O2 1.6(7) . . . . no C4 O3 C3 C2 -179.8(4) . . . . no O1 C2 C3 O2 -3.3(7) . . . . no C1 C2 C3 O2 -123.7(5) . . . . no O1 C2 C3 O3 178.1(4) . . . . no C1 C2 C3 O3 57.7(5) . . . . no C3 O3 C4 C5 176.3(4) . . . . no O3 C4 C5 C6 -64.3(6) . . . . no C4 C5 C6 C7 175.3(5) . . . . no C5 C6 C7 C7 -179.1(5) . . . 2_647 no F5 C8 C9 O4 -67.1(5) . . . . no F6 C8 C9 O4 171.5(5) . . . . no F4 C8 C9 O4 51.9(6) . . . . no F5 C8 C9 C10 52.2(5) . . . . no F6 C8 C9 C10 -69.1(6) . . . . no F4 C8 C9 C10 171.2(4) . . . . no C11 O6 C10 O5 1.8(6) . . . . no C11 O6 C10 C9 -177.6(3) . . . . no O4 C9 C10 O5 10.2(6) . . . . no C8 C9 C10 O5 -109.9(5) . . . . no O4 C9 C10 O6 -170.4(4) . . . . no C8 C9 C10 O6 69.5(5) . . . . no C10 O6 C11 C12 82.7(4) . . . . no O6 C11 C12 C13 53.8(4) . . . . no C11 C12 C13 C14 57.6(5) . . . . no C12 C13 C14 C14 174.5(5) . . . 2_538 no #==END #------------------------------------------------------------------------------ data_RS-1f_mixed_solvate _database_code_depnum_ccdc_archive 'CCDC 246916' _audit_creation_date 2005-05-08T16:50:28-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common ; Nonamethylene-(R,S)-(+-)-bis(3,3,3-trifluorolactate) hexane ether H2O mixed solvate ; _chemical_formula_sum 'C21 H36 F6 O6' _chemical_formula_moiety 'C15 H22 F6 O6, C6H14' _chemical_formula_weight 498.50 _chemical_melting_point 341 _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= 0 (c = 1.0, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_Int_Tables_number 62 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z+1/2' '-x, y+1/2, -z' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z-1/2' 'x, -y-1/2, z' 'x-1/2, y, -z-1/2' _cell_length_a 15.7479(5) _cell_length_b 27.1355(10) _cell_length_c 5.03090(10) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2149.84(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 12054 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 100(1) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _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. The crystal was cooled by cold nitrogen flux of a low temperature device during the data collection. The solvate contains mainly hexane and H2O, with trace amount of ether. However, there is no information regarding the number of solvent molecules, because of relatively low electron density in voids and easy escape of volatile solvents from voids. The number of solvent molecules were assumed one molecule, then the related crystallographic parameters were calculated based on solvate formula. #loop_ #_chemical_formula_sum #_chemical_formula_moiety #_chemical_formula_weight #_exptl_crystal_density_diffrn #_exptl_crystal_F_000 #_exptl_absorpt_coefficient_mu hexane ether H2O mixed solvate (1) 'C25 H48 F6 O8' 'C15 H22 F6 O6, C6H14, C4H10O, H2O' 590.63 1.825 1264 0.165 hexane H2O mixed solvate (2) 'C21 H38 F6 O7' 'C15 H22 F6 O6, C6H14, H2O' 516.51 1.596 1096 0.149 hexane solvate (3) 'C21 H36 F6 O6' 'C15 H22 F6 O6, C6H14' 498.50 1.540 1056 0.143 H2O solvate (4) 'C15 H24 F6 O7' 'C15 H22 F6 O6, H2O' 430.34 1.330 896 0.135 solvent free (5) 'C15 H22 F6 O6' 'C15 H22 F6 O6' 412.32 1.274 856 0.128 Hexane ether H2O mixed solvate (1), hexane H2O mixed solvate (2), and hexane solvate (3) showed larger density than density of 1f' (1.495). It is considered that inclusion of two solvent molecules per one molecule of 1f is imfeasible because of small size of one-dimensional channels of the crystal. So that the hexane solvate (3) formula C21 H36 F6 O6 was adopted for calculation of the related crystallographic parameters, ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; 'ABSCOR (HIGASHI, T., Rigaku, 1995)' Guest free formula C15 H22 F6 O6 is used for Absorption coorection, because there is no information regarding the type and the number of solvent molecules. ; _exptl_absorpt_correction_T_min 0.639 _exptl_absorpt_correction_T_max 0.975 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(1) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_reflns_number 4499 _diffrn_reflns_av_R_equivalents 0.0132 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.5 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.942 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 1900 _reflns_number_gt 1707 _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-atom of OH has been located from Fourier difference maps and constrained 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^)+(0.0690P)^2^+0.7327P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.025(2) _refine_ls_number_reflns 1900 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1167 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.326 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.081 #----------------------------------------------------------------------------# # DISORDER FIELD INFORMATION # #----------------------------------------------------------------------------# _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 347.7 A^3^[16% of cell volume], and a void electron population of 104 per cell. Refinement after the SQUEEZE routine gave significantly improved R values. [R values before SQUEEZE] R1 = 0.1035 for 1742 >2sigma(I) data R1 = 0.1146, wR2 = 0.2937, GooF = S = 2.679 for all data (1902 data and 0 restraint / 127 parameters) ; # SQUEEZE RESULTS #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 0.299 0.250 -0.036 88.2 26.1 #2 0.799 0.250 -0.045 88.2 26.1 #3 0.701 0.750 -0.044 88.2 26.1 #4 0.201 0.750 -0.052 88.2 26.1 #----------------------------------------------------------------------------# # 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 0.36282(7) 0.13079(4) 0.2736(2) 0.0420(3) Uani 1 1 d . . . F2 F 0.28141(7) 0.12387(4) 0.6157(2) 0.0414(3) Uani 1 1 d . . . F3 F 0.23366(6) 0.10675(4) 0.2266(2) 0.0389(3) Uani 1 1 d . . . O1 O 0.25911(7) 0.02294(4) 0.5121(2) 0.0281(3) Uani 1 1 d . . . H1 H 0.2346 0.0096 0.3878 0.048 Uiso 1 1 calc R . . O2 O 0.39333(7) 0.02496(4) 0.8262(2) 0.0227(3) Uani 1 1 d . . . O3 O 0.47292(6) 0.06328(4) 0.5168(2) 0.0206(3) Uani 1 1 d . . . C1 C 0.30183(10) 0.10330(6) 0.3843(3) 0.0272(4) Uani 1 1 d . . . C2 C 0.32841(9) 0.04992(6) 0.4155(3) 0.0207(4) Uani 1 1 d . . . H2 H 0.3458 0.0367 0.2426 0.025 Uiso 1 1 calc R . . C3 C 0.40147(9) 0.04469(5) 0.6133(3) 0.0180(3) Uani 1 1 d . . . C4 C 0.54693(9) 0.06330(5) 0.6944(3) 0.0223(4) Uani 1 1 d . . . H4 H 0.5986 0.0619 0.5896 0.027 Uiso 1 1 calc R . . H3 H 0.5452 0.0344 0.8077 0.027 Uiso 1 1 calc R . . C5 C 0.54762(10) 0.10922(6) 0.8644(3) 0.0222(4) Uani 1 1 d . . . H6 H 0.5952 0.1074 0.9865 0.027 Uiso 1 1 calc R . . H5 H 0.496 0.1101 0.9694 0.027 Uiso 1 1 calc R . . C6 C 0.55423(11) 0.15678(5) 0.7046(3) 0.0262(4) Uani 1 1 d . . . H8 H 0.6061 0.156 0.6007 0.031 Uiso 1 1 calc R . . H7 H 0.5069 0.1585 0.5817 0.031 Uiso 1 1 calc R . . C7 C 0.55427(14) 0.20281(6) 0.8766(4) 0.0351(5) Uani 1 1 d . . . H10 H 0.6035 0.2022 0.9924 0.042 Uiso 1 1 calc R . . H9 H 0.504 0.2028 0.9878 0.042 Uiso 1 1 calc R . . C8 C 0.5559(2) 0.25 0.7122(5) 0.0355(6) Uani 1 2 d S . . H12 H 0.5074 0.25 0.5936 0.043 Uiso 1 2 calc SR . . H11 H 0.6067 0.25 0.6033 0.043 Uiso 1 2 calc SR . . 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 0.0243(6) 0.0336(6) 0.0683(8) 0.0243(5) 0.0037(5) -0.0006(4) F2 0.0440(7) 0.0376(6) 0.0426(7) -0.0110(5) 0.0012(5) 0.0120(5) F3 0.0234(5) 0.0532(7) 0.0402(7) 0.0125(5) -0.0045(4) 0.0031(4) O1 0.0266(6) 0.0383(7) 0.0193(6) -0.0003(5) -0.0016(4) -0.0172(5) O2 0.0228(6) 0.0265(6) 0.0188(6) 0.0026(4) 0.0025(4) -0.0029(4) O3 0.0194(6) 0.0209(5) 0.0217(6) 0.0013(4) 0.0026(4) -0.0036(4) C1 0.0176(7) 0.0340(9) 0.0300(9) 0.0039(7) 0.0021(7) 0.0000(7) C2 0.0210(8) 0.0249(8) 0.0162(8) -0.0011(6) 0.0024(6) -0.0053(6) C3 0.0200(7) 0.0152(7) 0.0189(8) -0.0038(6) 0.0046(6) -0.0017(6) C4 0.0150(7) 0.0196(7) 0.0323(9) 0.0024(6) 0.0002(6) 0.0007(5) C5 0.0191(8) 0.0216(8) 0.0260(8) 0.0018(6) -0.0030(6) -0.0010(6) C6 0.0308(9) 0.0184(8) 0.0294(9) 0.0012(6) 0.0012(7) -0.0013(6) C7 0.0542(12) 0.0202(9) 0.0310(10) 0.0002(7) -0.0017(8) -0.0014(7) C8 0.0540(16) 0.0191(11) 0.0334(14) 0 -0.0013(12) 0 #----------------------------------------------------------------------------# # 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 1.338(2) . no F2 C1 1.330(2) . no F3 C1 1.338(2) . no O1 C2 1.4013(18) . no O1 H1 0.82 . no O2 C3 1.2040(19) . no O3 C3 1.3253(18) . no O3 C4 1.4685(18) . no C1 C2 1.516(2) . no C2 C3 1.528(2) . no C2 H2 0.98 . no C4 C5 1.511(2) . no C4 H4 0.97 . no C4 H3 0.97 . no C5 C6 1.524(2) . no C5 H6 0.97 . no C5 H5 0.97 . no C6 C7 1.519(2) . no C6 H8 0.97 . no C6 H7 0.97 . no C7 C8 1.525(2) . no C7 H10 0.97 . no C7 H9 0.97 . no C8 C7 1.525(2) 7_565 no C8 H12 0.97 . no C8 H11 0.97 . 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 116.81(11) . . no F2 C1 F1 107.69(14) . . no F2 C1 F3 107.19(13) . . no F1 C1 F3 106.86(13) . . no F2 C1 C2 112.15(14) . . no F1 C1 C2 112.19(13) . . no F3 C1 C2 110.48(14) . . no O1 C2 C1 108.67(13) . . no O1 C2 C3 108.18(12) . . no C1 C2 C3 111.37(12) . . no O1 C2 H2 109.5 . . no C1 C2 H2 109.5 . . no C3 C2 H2 109.5 . . no O2 C3 O3 125.84(14) . . no O2 C3 C2 122.71(13) . . no O3 C3 C2 111.42(12) . . no O3 C4 C5 110.51(12) . . no O3 C4 H4 109.5 . . no C5 C4 H4 109.5 . . no O3 C4 H3 109.5 . . no C5 C4 H3 109.5 . . no H4 C4 H3 108.1 . . no C4 C5 C6 113.60(13) . . no C4 C5 H6 108.8 . . no C6 C5 H6 108.8 . . no C4 C5 H5 108.8 . . no C6 C5 H5 108.8 . . no H6 C5 H5 107.7 . . no C7 C6 C5 113.32(14) . . no C7 C6 H8 108.9 . . no C5 C6 H8 108.9 . . no C7 C6 H7 108.9 . . no C5 C6 H7 108.9 . . no H8 C6 H7 107.7 . . no C6 C7 C8 112.43(15) . . no C6 C7 H10 109.1 . . no C8 C7 H10 109.1 . . no C6 C7 H9 109.1 . . no C8 C7 H9 109.1 . . no H10 C7 H9 107.8 . . no C7 C8 C7 114.3(2) . 7_565 no C7 C8 H12 108.7 . . no C7 C8 H12 108.7 7_565 . no C7 C8 H11 108.7 . . no C7 C8 H11 108.7 7_565 . no H12 C8 H11 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 63.38(17) . . . . no F1 C1 C2 O1 -175.26(13) . . . . no F3 C1 C2 O1 -56.14(16) . . . . no F2 C1 C2 C3 -55.69(17) . . . . no F1 C1 C2 C3 65.67(17) . . . . no F3 C1 C2 C3 -175.21(12) . . . . no C4 O3 C3 O2 -5.2(2) . . . . no C4 O3 C3 C2 176.34(11) . . . . no O1 C2 C3 O2 -7.6(2) . . . . no C1 C2 C3 O2 111.78(16) . . . . no O1 C2 C3 O3 170.90(12) . . . . no C1 C2 C3 O3 -69.74(15) . . . . no C3 O3 C4 C5 -86.88(15) . . . . no O3 C4 C5 C6 -61.74(16) . . . . no C4 C5 C6 C7 179.60(14) . . . . no C5 C6 C7 C8 -176.78(18) . . . . no C6 C7 C8 C7 178.87(15) . . . 7_565 no #==END #------------------------------------------------------------------------------ data_RS-1f(')_(polymorph_of_RS-1f) _database_code_depnum_ccdc_archive 'CCDC 264877' _audit_creation_date 'Sat Feb 26 21:28:51 2005' _audit_creation_method 'by the program teXsan' _audit_update_record ;2005-2-26 Checkcif ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common Nonamethylene-(R,S)-(+-)-bis(3,3,3-trifluorolactate) _chemical_formula_sum 'C15 H22 F6 O6 ' _chemical_formula_moiety 'C15 H22 F6 O6 ' _chemical_formula_weight 412.32 _chemical_melting_point 342 _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= 0 (c = 1.0, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 5.3266(7) _cell_length_b 20.331(5) _cell_length_c 16.967(4) _cell_angle_alpha 90 _cell_angle_beta 94.52(1) _cell_angle_gamma 90 _cell_volume 1831.8(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 12100 _cell_measurement_theta_min 1.2 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 115(1) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_F_000 856 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 1.000 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.495 _exptl_crystal_density_method 'not measured' #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (HIGASHI, T., Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.569 _exptl_absorpt_correction_T_max 0.970 _exptl_special_details ;The compound was crystallized from isooctane/THF solution. 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. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _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_ambient_temperature 115(1) _diffrn_reflns_number 6940 _reflns_number_total 4035 _diffrn_reflns_av_R_equivalents 0.020 _diffrn_reflns_theta_max 27.5 _diffrn_measured_fraction_theta_max 0.9417 _diffrn_reflns_theta_full 25.75 _diffrn_measured_fraction_theta_full 0.9464 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 #----------------------------------------------------------------------------# # 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 'SIR97 (Altomare et al., 1999)' _computing_publication_material 'teXsan Ver. 1.11 (MSC)' _computing_molecular_graphics 'Mercury Ver. 1.3 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ;Refinement using reflections with F^2^ > -10.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). Non H-atoms were refined anisotropically. H-atoms has been located from Fourier difference maps and refined isotropically. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _reflns_number_gt 3034 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_R_factor_gt 0.0451 _refine_ls_R_factor_all 0.0494 _refine_ls_wR_factor_ref 0.1559 _refine_ls_number_reflns 3330 _refine_ls_number_parameters 332 _refine_ls_goodness_of_fit_ref 1.678 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.08000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0003 _refine_diff_density_max 0.17 _refine_diff_density_min -0.26 _refine_ls_extinction_method none #----------------------------------------------------------------------------# # 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F(1) F 0.2984(3) -0.26515(7) -0.80577(9) 0.0488(4) Uani 1.00 d . . . F(2) F -0.0581(3) -0.25155(7) -0.7576(1) 0.0572(5) Uani 1.00 d . . . F(3) F 0.2757(3) -0.26792(8) -0.68103(9) 0.0544(5) Uani 1.00 d . . . F(4) F 1.3393(2) -0.28186(6) 0.00578(9) 0.0418(4) Uani 1.00 d . . . F(5) F 1.6338(3) -0.30683(6) -0.06757(8) 0.0398(4) Uani 1.00 d . . . F(6) F 1.7238(3) -0.27722(6) 0.05268(9) 0.0465(4) Uani 1.00 d . . . O(1) O 0.0188(2) -0.37586(7) -0.83131(8) 0.0218(3) Uani 1.00 d . . . O(2) O -0.2954(2) -0.39625(7) -0.72239(8) 0.0237(3) Uani 1.00 d . . . O(3) O 0.0001(2) -0.37246(7) -0.62525(7) 0.0213(3) Uani 1.00 d . . . O(4) O 1.3971(2) -0.43628(6) -0.08336(7) 0.0187(3) Uani 1.00 d . . . O(5) O 1.1346(2) -0.42678(7) 0.01345(8) 0.0231(3) Uani 1.00 d . . . O(6) O 1.5036(2) -0.38456(7) 0.11223(8) 0.0218(3) Uani 1.00 d . . . C(1) C 0.1572(4) -0.2850(1) -0.7496(1) 0.0304(5) Uani 1.00 d . . . C(2) C 0.1103(3) -0.35888(9) -0.7551(1) 0.0172(4) Uani 1.00 d . . . C(3) C -0.0873(3) -0.37841(8) -0.6998(1) 0.0161(4) Uani 1.00 d . . . C(4) C -0.1822(3) -0.38040(9) -0.5662(1) 0.0201(5) Uani 1.00 d . . . C(5) C -0.0461(3) -0.36320(9) -0.4883(1) 0.0191(4) Uani 1.00 d . . . C(6) C 0.1533(3) -0.41294(9) -0.4580(1) 0.0191(4) Uani 1.00 d . . . C(7) C 0.3065(3) -0.38729(9) -0.3852(1) 0.0179(4) Uani 1.00 d . . . C(8) C 0.4952(3) -0.43637(9) -0.3471(1) 0.0189(4) Uani 1.00 d . . . C(9) C 0.6606(3) -0.40542(9) -0.2797(1) 0.0188(4) Uani 1.00 d . . . C(10) C 0.8475(3) -0.45323(9) -0.2381(1) 0.0195(4) Uani 1.00 d . . . C(11) C 1.0229(3) -0.41965(9) -0.1755(1) 0.0186(4) Uani 1.00 d . . . C(12) C 1.2006(3) -0.46877(9) -0.1344(1) 0.0187(4) Uani 1.00 d . . . C(13) C 1.3345(3) -0.41776(8) -0.01320(10) 0.0161(4) Uani 1.00 d . . . C(14) C 1.5513(3) -0.38240(8) 0.0330(1) 0.0171(4) Uani 1.00 d . . . C(15) C 1.5624(3) -0.31160(10) 0.0053(1) 0.0258(5) Uani 1.00 d . . . H(1) H 0.153(5) -0.380(1) -0.858(2) 0.033(6) Uiso 1.00 d . . . H(2) H 0.273(4) -0.382(1) -0.739(1) 0.016(5) Uiso 1.00 d . . . H(3) H -0.321(4) -0.349(1) -0.580(1) 0.021(5) Uiso 1.00 d . . . H(4) H -0.241(5) -0.427(1) -0.567(2) 0.035(6) Uiso 1.00 d . . . H(5) H 0.031(4) -0.322(1) -0.495(1) 0.027(6) Uiso 1.00 d . . . H(6) H -0.165(4) -0.358(1) -0.452(1) 0.025(5) Uiso 1.00 d . . . H(7) H 0.271(4) -0.420(1) -0.504(1) 0.017(5) Uiso 1.00 d . . . H(8) H 0.065(5) -0.454(1) -0.445(2) 0.042(7) Uiso 1.00 d . . . H(9) H 0.390(3) -0.349(1) -0.403(1) 0.013(4) Uiso 1.00 d . . . H(10) H 0.199(4) -0.374(1) -0.347(1) 0.019(5) Uiso 1.00 d . . . H(11) H 0.604(4) -0.454(1) -0.386(1) 0.026(5) Uiso 1.00 d . . . H(12) H 0.403(4) -0.473(1) -0.326(1) 0.025(5) Uiso 1.00 d . . . H(13) H 0.752(3) -0.368(1) -0.302(1) 0.011(4) Uiso 1.00 d . . . H(14) H 0.560(4) -0.389(1) -0.242(1) 0.022(5) Uiso 1.00 d . . . H(15) H 0.943(5) -0.474(1) -0.277(2) 0.037(7) Uiso 1.00 d . . . H(16) H 0.744(4) -0.487(1) -0.210(1) 0.024(5) Uiso 1.00 d . . . H(17) H 1.117(4) -0.387(1) -0.202(1) 0.013(5) Uiso 1.00 d . . . H(18) H 0.921(4) -0.400(1) -0.142(1) 0.024(5) Uiso 1.00 d . . . H(19) H 1.289(4) -0.490(1) -0.171(1) 0.025(6) Uiso 1.00 d . . . H(20) H 1.104(3) -0.4985(10) -0.101(1) 0.009(4) Uiso 1.00 d . . . H(21) H 1.711(4) -0.405(1) 0.024(1) 0.016(5) Uiso 1.00 d . . . H(22) H 1.636(5) -0.380(1) 0.140(2) 0.035(7) Uiso 1.00 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F(1) 0.0782(10) 0.0279(7) 0.0438(9) -0.0200(7) 0.0264(7) 0.0004(6) F(2) 0.072(1) 0.0219(7) 0.079(1) 0.0163(7) 0.0156(9) 0.0008(7) F(3) 0.081(1) 0.0467(9) 0.0356(9) -0.0376(8) 0.0047(7) -0.0170(6) F(4) 0.0442(7) 0.0261(7) 0.0545(9) 0.0164(5) -0.0004(6) 0.0042(6) F(5) 0.0541(8) 0.0328(7) 0.0338(7) -0.0059(6) 0.0117(6) 0.0133(6) F(6) 0.0573(8) 0.0275(7) 0.0517(9) -0.0220(6) -0.0144(7) 0.0040(6) O(1) 0.0186(6) 0.0325(8) 0.0142(7) -0.0020(5) 0.0011(5) -0.0048(5) O(2) 0.0160(6) 0.0351(8) 0.0193(7) -0.0025(5) -0.0030(5) -0.0027(5) O(3) 0.0157(6) 0.0343(7) 0.0133(7) -0.0019(5) -0.0027(5) 0.0005(5) O(4) 0.0138(6) 0.0268(7) 0.0154(7) -0.0003(5) -0.0004(5) -0.0011(5) O(5) 0.0171(6) 0.0344(8) 0.0178(7) -0.0048(5) 0.0016(5) -0.0016(5) O(6) 0.0188(6) 0.0316(7) 0.0141(7) -0.0020(5) -0.0048(5) 0.0001(5) C(1) 0.044(1) 0.0227(10) 0.026(1) -0.0061(8) 0.0082(8) -0.0035(8) C(2) 0.0163(8) 0.0195(9) 0.0154(9) -0.0005(6) -0.0024(6) -0.0005(6) C(3) 0.0154(8) 0.0190(8) 0.0134(9) 0.0033(6) -0.0023(6) -0.0003(6) C(4) 0.0154(8) 0.0276(10) 0.0173(9) 0.0005(7) 0.0015(6) 0.0026(7) C(5) 0.0201(9) 0.0194(9) 0.0176(9) 0.0020(7) 0.0005(7) 0.0008(7) C(6) 0.0204(9) 0.0198(9) 0.0166(9) 0.0013(7) -0.0019(7) -0.0003(7) C(7) 0.0178(8) 0.0200(9) 0.0157(9) -0.0006(6) -0.0008(7) -0.0006(7) C(8) 0.0193(8) 0.0201(9) 0.0167(9) -0.0013(7) -0.0018(7) 0.0015(7) C(9) 0.0181(8) 0.0216(9) 0.0165(9) 0.0000(7) -0.0003(7) 0.0004(7) C(10) 0.0185(8) 0.0236(9) 0.0162(9) 0.0001(7) -0.0013(7) -0.0007(7) C(11) 0.0176(8) 0.0215(9) 0.0165(9) 0.0002(7) -0.0005(7) -0.0005(7) C(12) 0.0192(8) 0.0223(9) 0.0140(9) -0.0006(7) -0.0030(7) -0.0010(7) C(13) 0.0165(8) 0.0180(8) 0.0135(9) 0.0023(6) -0.0007(6) 0.0026(6) C(14) 0.0147(8) 0.0196(9) 0.0166(9) 0.0012(6) -0.0008(6) 0.0011(7) C(15) 0.0271(9) 0.0228(9) 0.027(1) -0.0007(7) -0.0017(7) 0.0014(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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F(1) C(1) 1.323(3) . . no F(2) C(1) 1.331(3) . . no F(3) C(1) 1.325(3) . . no F(4) C(15) 1.334(2) . . no F(5) C(15) 1.325(3) . . no F(6) C(15) 1.329(2) . . no O(1) C(2) 1.388(2) . . no O(1) H(1) 0.88(3) . . no O(2) C(3) 1.200(2) . . no O(3) C(3) 1.319(2) . . no O(3) C(4) 1.458(2) . . no O(4) C(12) 1.462(2) . . no O(4) C(13) 1.316(2) . . no O(5) C(13) 1.203(2) . . no O(6) C(14) 1.389(2) . . no O(6) H(22) 0.83(3) . . no C(1) C(2) 1.524(3) . . no C(2) C(3) 1.517(2) . . no C(2) H(2) 1.00(2) . . no C(4) C(5) 1.498(3) . . no C(4) H(3) 0.99(2) . . no C(4) H(4) 1.01(3) . . no C(5) C(6) 1.526(2) . . no C(5) H(5) 0.94(2) . . no C(5) H(6) 0.92(2) . . no C(6) C(7) 1.518(2) . . no C(6) H(7) 1.04(2) . . no C(6) H(8) 0.99(3) . . no C(7) C(8) 1.524(2) . . no C(7) H(9) 0.96(2) . . no C(7) H(10) 0.94(2) . . no C(8) C(9) 1.523(2) . . no C(8) H(11) 0.98(2) . . no C(8) H(12) 0.98(2) . . no C(9) C(10) 1.524(2) . . no C(9) H(13) 0.99(2) . . no C(9) H(14) 0.93(2) . . no C(10) C(11) 1.520(2) . . no C(10) H(15) 0.96(3) . . no C(10) H(16) 1.01(2) . . no C(11) C(12) 1.509(2) . . no C(11) H(17) 0.96(2) . . no C(11) H(18) 0.91(2) . . no C(12) H(19) 0.92(2) . . no C(12) H(20) 1.00(2) . . no C(13) C(14) 1.524(2) . . no C(14) C(15) 1.517(3) . . no C(14) H(21) 0.99(2) . . 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C(2) O(1) H(1) 105(1) . . . no C(3) O(3) C(4) 116.4(1) . . . no C(12) O(4) C(13) 116.4(1) . . . no C(14) O(6) H(22) 109(1) . . . no F(1) C(1) F(2) 107.7(2) . . . no F(1) C(1) F(3) 107.1(2) . . . no F(1) C(1) C(2) 110.8(2) . . . no F(2) C(1) F(3) 107.6(2) . . . no F(2) C(1) C(2) 111.2(2) . . . no F(3) C(1) C(2) 112.2(2) . . . no O(1) C(2) C(1) 110.3(2) . . . no O(1) C(2) C(3) 107.5(1) . . . no O(1) C(2) H(2) 111(1) . . . no C(1) C(2) C(3) 109.7(1) . . . no C(1) C(2) H(2) 107(1) . . . no C(3) C(2) H(2) 109(1) . . . no O(2) C(3) O(3) 125.6(2) . . . no O(2) C(3) C(2) 123.3(2) . . . no O(3) C(3) C(2) 111.1(1) . . . no O(3) C(4) C(5) 106.2(1) . . . no O(3) C(4) H(3) 106(1) . . . no O(3) C(4) H(4) 108(1) . . . no C(5) C(4) H(3) 111(1) . . . no C(5) C(4) H(4) 110(1) . . . no H(3) C(4) H(4) 112(1) . . . no C(4) C(5) C(6) 114.7(2) . . . no C(4) C(5) H(5) 106(1) . . . no C(4) C(5) H(6) 107(1) . . . no C(6) C(5) H(5) 109(1) . . . no C(6) C(5) H(6) 109(1) . . . no H(5) C(5) H(6) 108(2) . . . no C(5) C(6) C(7) 111.2(1) . . . no C(5) C(6) H(7) 106(1) . . . no C(5) C(6) H(8) 107(1) . . . no C(7) C(6) H(7) 109(1) . . . no C(7) C(6) H(8) 110(1) . . . no H(7) C(6) H(8) 111(1) . . . no C(6) C(7) C(8) 114.5(1) . . . no C(6) C(7) H(9) 104(1) . . . no C(6) C(7) H(10) 110(1) . . . no C(8) C(7) H(9) 111(1) . . . no C(8) C(7) H(10) 107(1) . . . no H(9) C(7) H(10) 108(1) . . . no C(7) C(8) C(9) 111.8(1) . . . no C(7) C(8) H(11) 110(1) . . . no C(7) C(8) H(12) 108(1) . . . no C(9) C(8) H(11) 108(1) . . . no C(9) C(8) H(12) 108(1) . . . no H(11) C(8) H(12) 108(1) . . . no C(8) C(9) C(10) 113.7(2) . . . no C(8) C(9) H(13) 107(1) . . . no C(8) C(9) H(14) 109(1) . . . no C(10) C(9) H(13) 109(1) . . . no C(10) C(9) H(14) 107(1) . . . no H(13) C(9) H(14) 108(1) . . . no C(9) C(10) C(11) 112.3(1) . . . no C(9) C(10) H(15) 109(1) . . . no C(9) C(10) H(16) 106(1) . . . no C(11) C(10) H(15) 110(1) . . . no C(11) C(10) H(16) 107(1) . . . no H(15) C(10) H(16) 111(2) . . . no C(10) C(11) C(12) 110.8(1) . . . no C(10) C(11) H(17) 107(1) . . . no C(10) C(11) H(18) 105(1) . . . no C(12) C(11) H(17) 110(1) . . . no C(12) C(11) H(18) 112(1) . . . no H(17) C(11) H(18) 110(1) . . . no O(4) C(12) C(11) 111.6(1) . . . no O(4) C(12) H(19) 103(1) . . . no O(4) C(12) H(20) 108(1) . . . no C(11) C(12) H(19) 110(1) . . . no C(11) C(12) H(20) 109(1) . . . no H(19) C(12) H(20) 113(1) . . . no O(4) C(13) O(5) 126.2(2) . . . no O(4) C(13) C(14) 111.4(1) . . . no O(5) C(13) C(14) 122.4(2) . . . no O(6) C(14) C(13) 107.1(1) . . . no O(6) C(14) C(15) 110.2(2) . . . no O(6) C(14) H(21) 111(1) . . . no C(13) C(14) C(15) 109.6(1) . . . no C(13) C(14) H(21) 108(1) . . . no C(15) C(14) H(21) 109(1) . . . no F(4) C(15) F(5) 107.1(2) . . . no F(4) C(15) F(6) 107.0(2) . . . no F(4) C(15) C(14) 111.8(2) . . . no F(5) C(15) F(6) 107.9(2) . . . no F(5) C(15) C(14) 112.3(2) . . . no F(6) C(15) C(14) 110.5(2) . . . 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 F(1) C(1) C(2) O(1) -51.9(2) . . . . no F(1) C(1) C(2) C(3) -170.2(2) . . . . no F(2) C(1) C(2) O(1) 67.9(2) . . . . no F(2) C(1) C(2) C(3) -50.4(2) . . . . no F(3) C(1) C(2) O(1) -171.6(2) . . . . no F(3) C(1) C(2) C(3) 70.1(2) . . . . no F(4) C(15) C(14) O(6) -66.2(2) . . . . no F(4) C(15) C(14) C(13) 51.3(2) . . . . no F(5) C(15) C(14) O(6) 173.3(1) . . . . no F(5) C(15) C(14) C(13) -69.1(2) . . . . no F(6) C(15) C(14) O(6) 52.8(2) . . . . no F(6) C(15) C(14) C(13) 170.4(1) . . . . no O(1) C(2) C(3) O(2) -9.5(2) . . . . no O(1) C(2) C(3) O(3) 171.1(1) . . . . no O(2) C(3) O(3) C(4) -8.1(3) . . . . no O(2) C(3) C(2) C(1) 110.4(2) . . . . no O(3) C(3) C(2) C(1) -69.0(2) . . . . no O(3) C(4) C(5) C(6) -70.2(2) . . . . no O(4) C(12) C(11) C(10) 170.7(1) . . . . no O(4) C(13) C(14) O(6) -160.3(1) . . . . no O(4) C(13) C(14) C(15) 80.2(2) . . . . no O(5) C(13) O(4) C(12) 2.4(3) . . . . no O(5) C(13) C(14) O(6) 19.4(2) . . . . no O(5) C(13) C(14) C(15) -100.1(2) . . . . no C(2) C(3) O(3) C(4) 171.3(1) . . . . no C(3) O(3) C(4) C(5) -173.0(1) . . . . no C(4) C(5) C(6) C(7) 172.0(1) . . . . no C(5) C(6) C(7) C(8) 175.1(1) . . . . no C(6) C(7) C(8) C(9) 174.2(1) . . . . no C(7) C(8) C(9) C(10) 178.3(1) . . . . no C(8) C(9) C(10) C(11) 175.6(1) . . . . no C(9) C(10) C(11) C(12) 178.6(1) . . . . no C(11) C(12) O(4) C(13) 81.1(2) . . . . no C(12) O(4) C(13) C(14) -177.9(1) . . . . no C(12) O(4) C(13) C(14) -177.9(1) . . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O(1) O(6) 2.830(2) . 1_454 no O(1) O(6) 2.840(2) . 1_354 no O(1) O(5) 2.941(2) . 1_454 no O(2) O(6) 2.933(2) . 1_354 no O(2) C(2) 3.260(2) . 1_455 no O(5) C(14) 3.277(2) . 1_455 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O(1) H(1) O(5) . . 1_454 0.88(2) 2.37(2) 2.941(1) 122(2) yes O(1) H(1) O(6) . . 1_454 0.88(2) 1.97(2) 2.830(1) 163(2) yes #END