# Electronic Supplementary Material (ESI) for Nanoscale # This journal is © The Royal Society of Chemistry 2012 data_global_4 _journal_name_full Nanoscale _journal_coden_cambridge 1542 loop_ _publ_author_name K.Kataoka T.Katagiri #==END #----------------------------------------------------------------------------# data_3e _database_code_depnum_ccdc_archive 'CCDC 246922' _audit_creation_method SHELXL-97 #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_common '(S,S)-(-)-octamethylene bis(3,3,3-trifluorolactate)' _chemical_melting_point 345 _chemical_formula_moiety 'C14 H20 F6 O6' _chemical_formula_sum 'C14 H20 F6 O6' _chemical_formula_weight 398.30 _chemical_absolute_configuration syn _chemical_optical_rotation '[\a]^25^~D~= -4.38 (c = 1.1, acetone)' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_Int_Tables_number 18 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 22.9706(5) _cell_length_b 5.14600(10) _cell_length_c 8.0376(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 950.10(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 9550 _cell_measurement_theta_min 5.4 _cell_measurement_theta_max 50.0 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_special_details ; A platelet crystal was mounted on a glass capillary. The crystal was cooled by cold nitrogen flux of a low temperature device during the data collection. ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8920 _exptl_absorpt_correction_T_max 0.9929 _exptl_absorpt_process_details ; ' (HIGASHI, T. (1995). Abscor - Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan.)' ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10 _diffrn_reflns_number 6670 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1053 _reflns_number_gt 990 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'RAPID-AUTO (Rigaku)' _computing_cell_refinement 'PAPID-AUTO (Rigaku)' _computing_data_reduction 'teXsan Ver. 1.11 (MSC)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'WinGX Ver. 1.7 (Farrugia, 1999)' _computing_molecular_graphics 'Mercury Ver. 1.3 (Bruno et al., 2002)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Non H-atoms were refined anisotropically. H-atom of OH has been located from Fourier difference maps and fixed to its position, while the remaining H-atoms were included in calculated positions and treated as riding atoms using the SHELXL default parameters. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+0.1475P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that of its precursor (S)-trifluorolactic acid at the chiral centre C2. This compound has no atom heavier than Si and analyzed by Mo radiation so that Flack parameter is not listed. Friedel pairs were merged before refinement. ; _refine_ls_number_reflns 1053 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.217 _refine_ls_restrained_S_all 1.217 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.88458(10) 0.7109(5) 0.4369(2) 0.0710(7) Uani 1 1 d . . . F2 F 0.91272(8) 0.6839(7) 0.6896(2) 0.0806(9) Uani 1 1 d . . . F3 F 0.89528(10) 0.3381(5) 0.5497(3) 0.0768(8) Uani 1 1 d . . . O1 O 0.77939(10) 0.4974(4) 0.5026(2) 0.0420(5) Uani 1 1 d . . . O2 O 0.77667(8) 0.2130(4) 0.7757(2) 0.0357(5) Uani 1 1 d . . . O3 O 0.82988(7) 0.5034(3) 0.9182(2) 0.0271(4) Uani 1 1 d . . . C1 C 0.87733(15) 0.5785(7) 0.5781(4) 0.0471(8) Uani 1 1 d . . . C2 C 0.81433(12) 0.5856(5) 0.6335(3) 0.0308(6) Uani 1 1 d . . . H2 H 0.8035 0.7642 0.6623 0.037 Uiso 1 1 calc R . . C3 C 0.80494(11) 0.4093(5) 0.7835(3) 0.0246(6) Uani 1 1 d . . . C4 C 0.82256(12) 0.3544(5) 1.0719(3) 0.0302(6) Uani 1 1 d . . . H4A H 0.7828 0.2917 1.0786 0.036 Uiso 1 1 calc R . . H4B H 0.8293 0.4674 1.1665 0.036 Uiso 1 1 calc R . . C5 C 0.86357(11) 0.1270(5) 1.0807(3) 0.0306(6) Uani 1 1 d . . . H5A H 0.8558 0.0127 0.9874 0.037 Uiso 1 1 calc R . . H5B H 0.8556 0.0304 1.1818 0.037 Uiso 1 1 calc R . . C6 C 0.92795(11) 0.2002(5) 1.0785(3) 0.0299(6) Uani 1 1 d . . . H6A H 0.9360 0.3002 0.9789 0.036 Uiso 1 1 calc R . . H6B H 0.9363 0.3098 1.1738 0.036 Uiso 1 1 calc R . . C7 C 0.96796(12) -0.0348(5) 1.0828(4) 0.0326(6) Uani 1 1 d . . . H7A H 0.9594 -0.1359 1.1817 0.039 Uiso 1 1 calc R . . H7B H 0.9598 -0.1432 0.9869 0.039 Uiso 1 1 calc R . . H10 H 0.7681 0.6183 0.4413 0.056 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0896(15) 0.0913(17) 0.0322(9) 0.0224(13) -0.0021(10) -0.0342(15) F2 0.0575(11) 0.147(2) 0.0369(10) 0.0138(14) -0.0087(9) -0.0501(16) F3 0.0639(13) 0.0862(17) 0.0802(17) 0.0140(15) 0.0255(13) 0.0257(14) O1 0.0603(12) 0.0299(9) 0.0358(10) 0.0061(10) -0.0258(10) 0.0017(11) O2 0.0430(11) 0.0337(10) 0.0305(10) -0.0008(9) -0.0064(9) -0.0125(10) O3 0.0350(9) 0.0233(8) 0.0230(8) -0.0029(9) -0.0046(8) 0.0000(8) C1 0.0567(19) 0.062(2) 0.0229(14) 0.0072(16) -0.0012(14) -0.0138(19) C2 0.0425(14) 0.0200(11) 0.0300(13) -0.0009(11) -0.0101(12) 0.0021(13) C3 0.0239(12) 0.0236(12) 0.0263(13) -0.0059(11) -0.0025(11) 0.0019(12) C4 0.0340(13) 0.0346(14) 0.0219(12) -0.0024(13) 0.0011(12) 0.0004(13) C5 0.0394(14) 0.0258(12) 0.0268(13) 0.0022(13) -0.0011(12) -0.0024(13) C6 0.0379(14) 0.0223(11) 0.0295(13) -0.0021(12) -0.0009(12) 0.0004(12) C7 0.0405(14) 0.0252(13) 0.0322(13) 0.0008(14) -0.0009(13) -0.0018(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C1 1.334(4) . no F2 C1 1.326(4) . no F3 C1 1.324(4) . no O1 C2 1.399(3) . no O1 H10 0.8300 . no O2 C3 1.203(3) . no O3 C3 1.318(3) . no O3 C4 1.464(3) . no C1 C2 1.515(5) . no C2 C3 1.524(4) . no C2 H2 0.9800 . no C4 C5 1.504(3) . no C4 H4A 0.9700 . no C4 H4B 0.9700 . no C5 C6 1.526(4) . no C5 H5A 0.9700 . no C5 H5B 0.9700 . no C6 C7 1.519(4) . no C6 H6A 0.9700 . no C6 H6B 0.9700 . no C7 C7 1.515(5) 2_755 no C7 H7A 0.9700 . no C7 H7B 0.9700 . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 H10 112.00 . . no C3 O3 C4 116.83(19) . . no F3 C1 F2 107.9(3) . . no F3 C1 F1 106.9(3) . . no F2 C1 F1 106.8(3) . . no F3 C1 C2 111.8(3) . . no F2 C1 C2 112.2(3) . . no F1 C1 C2 110.9(3) . . no O1 C2 C1 108.6(2) . . no O1 C2 C3 108.7(2) . . no C1 C2 C3 110.7(2) . . no O1 C2 H2 109.6 . . no C1 C2 H2 109.6 . . no C3 C2 H2 109.6 . . no O2 C3 O3 125.9(2) . . no O2 C3 C2 122.4(2) . . no O3 C3 C2 111.7(2) . . no O3 C4 C5 112.1(2) . . no O3 C4 H4A 109.2 . . no C5 C4 H4A 109.2 . . no O3 C4 H4B 109.2 . . no C5 C4 H4B 109.2 . . no H4A C4 H4B 107.9 . . no C4 C5 C6 114.5(2) . . no C4 C5 H5A 108.6 . . no C6 C5 H5A 108.6 . . no C4 C5 H5B 108.6 . . no C6 C5 H5B 108.6 . . no H5A C5 H5B 107.6 . . no C7 C6 C5 112.9(2) . . no C7 C6 H6A 109.0 . . no C5 C6 H6A 109.0 . . no C7 C6 H6B 109.0 . . no C5 C6 H6B 109.0 . . no H6A C6 H6B 107.8 . . no C7 C7 C6 113.6(3) 2_755 . no C7 C7 H7A 108.9 2_755 . no C6 C7 H7A 108.9 . . no C7 C7 H7B 108.9 2_755 . no C6 C7 H7B 108.9 . . no H7A C7 H7B 107.7 . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F3 C1 C2 O1 -64.9(3) . . . . no F2 C1 C2 O1 173.7(3) . . . . no F1 C1 C2 O1 54.3(3) . . . . no F3 C1 C2 C3 54.3(3) . . . . no F2 C1 C2 C3 -67.1(3) . . . . no F1 C1 C2 C3 173.6(2) . . . . no C4 O3 C3 O2 0.2(4) . . . . no C4 O3 C3 C2 178.42(19) . . . . no O1 C2 C3 O2 7.6(3) . . . . no C1 C2 C3 O2 -111.6(3) . . . . no O1 C2 C3 O3 -170.7(2) . . . . no C1 C2 C3 O3 70.1(3) . . . . no C3 O3 C4 C5 80.0(3) . . . . no O3 C4 C5 C6 61.2(3) . . . . no C4 C5 C6 C7 -178.4(2) . . . . no C5 C6 C7 C7 -179.30(17) . . . 2_755 no _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.29 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.214 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.049