# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002data_AARIA1 _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'H. Navratilova' ; Department of Organic Chemistry Faculty of Science Masaryk University Kotlarska 2 611 37 Brno Czech Republic ; 'R. de Gelder' ; Department of Inorganic Chemistry Nijmegen SON Research Center University of Nijmegen Toernooiveld 1 6525 ED Nijmegen The Netherlands ; 'Z. Kriz' ; National Centre for Biomolecular Research Faculty of Science Masaryk University Kotlarska 2 611 37 Brno Czech Republic ; _publ_contact_author_name 'Dr Hana Navratilova' _publ_contact_author_address ; Dept. Organic Chemistry Faculty of Science, Masaryk University Kotlaoska 2 Brno 611 37 CZECH REPUBLIC ; _publ_contact_author_phone '031 024 3652842' _publ_contact_author_fax '031 024 3553450' _publ_contact_author_email rdg@sci.kun.nl _publ_requested_journal 'Perkin Transactions 2' _publ_requested_coeditor_name ? _publ_section_title ; Enantiodiscrimination in NMR spectra and X-ray structures of diastereomeric salts of trans-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine with (S)-Mosher acid ; _publ_section_references ; CAD4 EXPRESS Enraf-Nonius diffractometer control software (1994). Release 5.1, Enraf-Nonius Delft, The Netherlands. Gelder, R. de, Graaff, R. A. G. de & Schenk, H. (1993). Acta Cryst. A49, 287--293. Grant, D. F. & Gabe, E. J. (1978). J. Appl. Cryst. 11, 114--120. International Tables for X-ray Crystallography (1974). Vol. IV, Birmingham, England: Kynoch Press. Lehman, M. S. & Larsen, F. K. (1974). Acta Cryst. A30, 580--584. North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351--359. Sheldrick, G. M. (1997). SHELXL-97, Program for the refinement of crystal structures. University of Gottingen, Germany. Smits, J. M. M., Behm, H., Bosman, W. P. & Beurskens, P. T. (1988). J. Crystallogr. Spectrosc. Res. 18, 447--450. Spek, A. L. (1990). Acta Cryst. A46, C-34. Spek, A. L. (1993). PLUTON, A program for plotting molecular and crystal structures. University of Utrecht, The Netherlands. Spek, A. L. (1995). PLATON-93, Program for display and analysis of crystal and molecular structures. University of Utrecht, The Netherlands. ; #============================================================================== data_1 _database_code_CSD 190457 _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 2000-01-03 _chemical_name_systematic ; (3S,4R)-piperidinium (S)-Mosher carboxylate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 F4 N O4' _chemical_formula_weight 457.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.30900(14) _cell_length_b 12.0081(4) _cell_length_c 13.0629(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.441(2) _cell_angle_gamma 90.00 _cell_volume 1146.46(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 40.524 _cell_measurement_theta_max 46.486 _exptl_crystal_description 'regular platelet' _exptl_crystal_colour 'transparent colourless' _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.05 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.954 _exptl_absorpt_correction_type experimental #_exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.931 _exptl_absorpt_correction_T_max 1.288 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD4' _diffrn_measurement_method \w/2\q-scan _diffrn_special_details ; \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.48 + 0.20tan\q)\%, range: 0.73\%-1.54\%, aperture (1.41 + 0.17tan\q)mm., range: 1.42-1.88mm. Maximum scan time: 30 sec/reflection. ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% 2.278 _diffrn_reflns_number 2378 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0120 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 70.01 _reflns_number_total 2279 _reflns_number_gt 2136 _reflns_number_observed 2136 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; CAD4 EXPRESS (Enraf-Nonius, 1994) ; #_computing_cell_refinement #; #CAD4 EXPRESS (Enraf-Nonius, 1994) #; _computing_data_reduction ; local programs (Smits et al., 1988), profile analysis (Lehman & Larsen, 1974, Grant & Gabe, 1978), EMPABS (North et al., 1968) ; _computing_structure_solution ; CRUNCH (de Gelder et al., 1993), ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTON (Spek, 1993), PLATON (Spek, 1990, 1995) ; _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0980P)^2^+0.1768P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0069(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_Flack -0.1(3) _refine_ls_number_reflns 2279 _refine_ls_number_parameters 300 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0468 _refine_ls_R_factor_obs 0.0468 _refine_ls_wR_factor_ref 0.1573 _refine_ls_wR_factor_all 0.1573 _refine_ls_wR_factor_gt 0.1535 _refine_ls_wR_factor_obs 0.1535 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_goodness_of_fit_all 1.153 _refine_ls_restrained_S_all 1.153 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_mean 0.000 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 F1 F -0.6208(4) -0.6656(2) -0.2935(3) 0.0908(9) Uani 1 d . . . F2 F -0.8847(5) -0.6647(3) -0.3631(3) 0.0967(10) Uani 1 d . . . F3 F -0.8548(5) -0.6902(2) -0.2012(2) 0.0971(9) Uani 1 d . . . F4 F -1.1524(6) -0.4381(5) 0.3834(3) 0.1430(18) Uani 1 d . . . O1 O -1.0047(3) -0.4866(2) -0.24236(17) 0.0561(6) Uani 1 d . . . O2 O -0.5491(3) -0.5050(3) -0.1534(2) 0.0625(7) Uani 1 d . . . O3 O -0.8017(4) -0.4400(4) -0.0848(2) 0.0780(9) Uani 1 d . . . O4 O -0.8780(4) -0.8527(3) 0.0164(2) 0.0706(8) Uani 1 d . . . H41 H -0.972(6) -0.880(4) 0.046(3) 0.064(12) Uiso 1 d . . . N1 N -0.3903(4) -0.6585(3) -0.0359(3) 0.0594(8) Uani 1 d . . . H1 H -0.458(6) -0.610(4) -0.071(3) 0.062(11) Uiso 1 d . . . C1 C -0.8164(4) -0.5068(3) -0.2590(2) 0.0503(7) Uani 1 d . . . C2 C -0.7356(4) -0.4296(4) -0.3410(2) 0.0536(8) Uani 1 d . . . C3 C -0.7649(7) -0.3160(4) -0.3295(4) 0.0782(12) Uani 1 d . . . H3 H -0.8293 -0.2900 -0.2732 0.094 Uiso 1 calc R . . C4 C -0.6997(8) -0.2416(6) -0.4003(5) 0.0996(17) Uani 1 d . . . H4 H -0.7216 -0.1658 -0.3922 0.119 Uiso 1 calc R . . C5 C -0.6023(9) -0.2788(8) -0.4833(5) 0.113(2) Uani 1 d . . . H5 H -0.5605 -0.2288 -0.5322 0.135 Uiso 1 calc R . . C6 C -0.5684(11) -0.3874(8) -0.4926(5) 0.122(3) Uani 1 d . . . H6 H -0.4989 -0.4120 -0.5475 0.146 Uiso 1 calc R . . C7 C -0.6340(8) -0.4656(5) -0.4226(4) 0.0924(16) Uani 1 d . . . H7 H -0.6091 -0.5409 -0.4311 0.111 Uiso 1 calc R . . C8 C -0.7943(6) -0.6306(4) -0.2806(3) 0.0665(10) Uani 1 d . . . C9 C -0.7144(4) -0.4809(3) -0.1547(2) 0.0495(7) Uani 1 d . . . C10 C -1.1260(5) -0.4773(5) -0.3282(3) 0.0761(12) Uani 1 d . . . H10A H -1.1326 -0.4009 -0.3497 0.114 Uiso 1 calc R . . H10B H -1.2457 -0.5025 -0.3092 0.114 Uiso 1 calc R . . H10C H -1.0813 -0.5222 -0.3835 0.114 Uiso 1 calc R . . C11 C -0.7425(5) -0.5858(4) 0.2181(3) 0.0616(9) Uani 1 d . . . C12 C -0.7734(6) -0.6163(6) 0.3192(3) 0.0840(14) Uani 1 d . . . H12 H -0.7010 -0.6708 0.3497 0.101 Uiso 1 calc R . . C13 C -0.9116(8) -0.5658(8) 0.3749(4) 0.105(2) Uani 1 d . . . H13 H -0.9328 -0.5866 0.4424 0.126 Uiso 1 calc R . . C14 C -1.0157(7) -0.4855(6) 0.3294(4) 0.0910(16) Uani 1 d . . . C15 C -0.9919(7) -0.4531(4) 0.2297(4) 0.0793(12) Uani 1 d . . . H15 H -1.0661 -0.3990 0.1999 0.095 Uiso 1 calc R . . C16 C -0.8534(6) -0.5038(4) 0.1750(3) 0.0666(9) Uani 1 d . . . H16 H -0.8340 -0.4825 0.1076 0.080 Uiso 1 calc R . . C17 C -0.5934(4) -0.6407(3) 0.1563(3) 0.0550(8) Uani 1 d . . . H17 H -0.5311 -0.6951 0.2004 0.066 Uiso 1 calc R . . C18 C -0.4516(5) -0.5552(4) 0.1212(4) 0.0711(11) Uani 1 d . . . H18A H -0.5131 -0.4969 0.0828 0.085 Uiso 1 calc R . . H18B H -0.3948 -0.5213 0.1809 0.085 Uiso 1 calc R . . C19 C -0.3045(5) -0.6065(4) 0.0552(4) 0.0742(11) Uani 1 d . . . H19A H -0.2188 -0.5494 0.0339 0.089 Uiso 1 calc R . . H19B H -0.2376 -0.6622 0.0941 0.089 Uiso 1 calc R . . C20 C -0.5229(5) -0.7486(3) -0.0052(3) 0.0566(8) Uani 1 d . . . H20A H -0.4571 -0.8071 0.0307 0.068 Uiso 1 calc R . . H20B H -0.5778 -0.7809 -0.0662 0.068 Uiso 1 calc R . . C21 C -0.6734(4) -0.7033(3) 0.0636(3) 0.0495(7) Uani 1 d . . . H21 H -0.7500 -0.6519 0.0237 0.059 Uiso 1 calc R . . C22 C -0.7917(5) -0.8002(3) 0.1001(3) 0.0572(8) Uani 1 d . . . H22A H -0.7159 -0.8537 0.1365 0.069 Uiso 1 calc R . . H22B H -0.8836 -0.7728 0.1470 0.069 Uiso 1 calc R . . C23 C -0.2506(6) -0.7020(5) -0.1075(4) 0.0848(15) Uani 1 d . . . H23A H -0.3104 -0.7340 -0.1662 0.127 Uiso 1 calc R . . H23B H -0.1785 -0.7579 -0.0736 0.127 Uiso 1 calc R . . H23C H -0.1727 -0.6422 -0.1290 0.127 Uiso 1 calc R . . 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 0.0904(17) 0.0732(16) 0.109(2) -0.0179(15) 0.0154(15) 0.0250(14) F2 0.126(2) 0.0694(16) 0.0945(19) -0.0281(15) -0.0107(18) -0.0127(17) F3 0.129(2) 0.0655(16) 0.097(2) 0.0098(15) 0.0290(18) -0.0081(16) F4 0.132(3) 0.177(4) 0.121(3) -0.044(3) 0.055(2) 0.016(3) O1 0.0430(11) 0.0750(16) 0.0504(11) -0.0029(12) 0.0021(9) -0.0026(11) O2 0.0462(12) 0.0698(16) 0.0714(15) 0.0123(13) -0.0018(10) 0.0044(12) O3 0.0591(14) 0.123(3) 0.0515(13) -0.0207(16) -0.0014(10) 0.0159(16) O4 0.0687(16) 0.0705(17) 0.0730(17) -0.0062(14) 0.0117(13) -0.0196(14) N1 0.0448(13) 0.0594(17) 0.0743(19) 0.0192(16) 0.0095(13) 0.0078(13) C1 0.0443(15) 0.0605(19) 0.0461(15) -0.0043(14) 0.0065(12) 0.0010(14) C2 0.0479(16) 0.067(2) 0.0461(16) 0.0019(15) 0.0014(12) -0.0025(15) C3 0.085(3) 0.069(3) 0.081(3) 0.007(2) 0.012(2) -0.005(2) C4 0.104(4) 0.082(3) 0.113(4) 0.030(3) 0.000(3) -0.012(3) C5 0.117(4) 0.138(6) 0.084(3) 0.039(4) 0.009(3) -0.049(5) C6 0.147(6) 0.138(7) 0.080(4) 0.007(4) 0.054(4) -0.035(5) C7 0.107(3) 0.098(4) 0.073(3) 0.000(3) 0.043(3) -0.011(3) C8 0.070(2) 0.062(2) 0.068(2) -0.0130(19) 0.0118(18) -0.0051(19) C9 0.0464(15) 0.0533(17) 0.0489(15) 0.0035(14) 0.0006(12) 0.0045(14) C10 0.057(2) 0.105(4) 0.067(2) -0.003(2) -0.0106(17) 0.005(2) C11 0.064(2) 0.067(2) 0.0536(17) -0.0015(17) -0.0031(15) -0.0096(18) C12 0.079(3) 0.116(4) 0.056(2) 0.007(3) -0.0076(19) -0.002(3) C13 0.097(3) 0.166(6) 0.053(2) -0.009(3) 0.011(2) -0.007(4) C14 0.085(3) 0.109(4) 0.079(3) -0.028(3) 0.019(2) -0.007(3) C15 0.081(3) 0.071(3) 0.087(3) -0.007(2) 0.011(2) -0.002(2) C16 0.075(2) 0.059(2) 0.065(2) 0.0007(19) 0.0030(17) -0.0009(19) C17 0.0518(17) 0.0548(18) 0.0582(18) 0.0121(15) -0.0071(14) -0.0052(15) C18 0.060(2) 0.069(2) 0.084(3) 0.003(2) -0.0068(19) -0.0155(19) C19 0.0486(17) 0.074(3) 0.100(3) 0.021(2) 0.0003(18) -0.0082(18) C20 0.0514(18) 0.0507(17) 0.0677(18) 0.0092(15) 0.0098(15) 0.0024(14) C21 0.0470(15) 0.0472(16) 0.0544(17) 0.0067(14) 0.0012(13) 0.0036(13) C22 0.0565(18) 0.0529(18) 0.0625(19) 0.0040(16) 0.0094(15) -0.0058(15) C23 0.062(2) 0.091(3) 0.102(3) 0.028(3) 0.032(2) 0.021(2) _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 C8 1.348(5) . Y F2 C8 1.325(5) . Y F3 C8 1.338(5) . Y F4 C14 1.353(6) . Y O1 C1 1.415(4) . Y O1 C10 1.429(4) . Y O2 C9 1.243(4) . Y O3 C9 1.221(4) . Y O4 C22 1.407(5) . Y N1 C19 1.479(6) . Y N1 C23 1.485(5) . Y N1 C20 1.508(5) . Y C1 C8 1.522(5) . Y C1 C2 1.538(5) . Y C1 C9 1.580(4) . Y C2 C7 1.374(6) . Y C2 C3 1.389(7) . Y C3 C4 1.374(7) . Y C4 C5 1.376(10) . Y C5 C6 1.333(13) . Y C6 C7 1.398(8) . Y C11 C12 1.390(6) . Y C11 C16 1.391(6) . Y C11 C17 1.513(5) . Y C12 C13 1.389(8) . Y C13 C14 1.362(10) . Y C14 C15 1.372(8) . Y C15 C16 1.384(6) . Y C17 C18 1.532(5) . Y C17 C21 1.538(5) . Y C18 C19 1.514(6) . Y C20 C21 1.526(5) . Y C21 C22 1.529(5) . Y 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 C1 O1 C10 119.4(3) . . Y C19 N1 C23 111.4(4) . . Y C19 N1 C20 111.0(3) . . Y C23 N1 C20 111.2(4) . . Y O1 C1 C8 107.5(3) . . Y O1 C1 C2 112.5(3) . . Y C8 C1 C2 114.7(3) . . Y O1 C1 C9 106.7(2) . . Y C8 C1 C9 107.6(3) . . Y C2 C1 C9 107.5(3) . . Y C7 C2 C3 118.5(4) . . Y C7 C2 C1 124.3(4) . . Y C3 C2 C1 117.2(3) . . Y C4 C3 C2 120.8(5) . . Y C3 C4 C5 120.2(6) . . Y C6 C5 C4 119.1(5) . . Y C5 C6 C7 122.2(6) . . Y C2 C7 C6 119.1(6) . . Y F2 C8 F3 107.5(4) . . Y F2 C8 F1 105.5(3) . . Y F3 C8 F1 104.3(4) . . Y F2 C8 C1 113.5(4) . . Y F3 C8 C1 110.0(3) . . Y F1 C8 C1 115.4(3) . . Y O3 C9 O2 126.8(3) . . Y O3 C9 C1 118.5(3) . . Y O2 C9 C1 114.7(3) . . Y C12 C11 C16 118.2(4) . . Y C12 C11 C17 121.0(4) . . Y C16 C11 C17 120.8(3) . . Y C13 C12 C11 120.5(5) . . Y C14 C13 C12 119.1(5) . . Y F4 C14 C13 118.9(5) . . Y F4 C14 C15 118.4(6) . . Y C13 C14 C15 122.7(5) . . Y C14 C15 C16 117.6(5) . . Y C15 C16 C11 121.9(4) . . Y C11 C17 C18 111.1(3) . . Y C11 C17 C21 111.2(3) . . Y C18 C17 C21 110.2(3) . . Y C19 C18 C17 112.5(4) . . Y N1 C19 C18 109.3(3) . . Y N1 C20 C21 111.6(3) . . Y C20 C21 C22 108.9(3) . . Y C20 C21 C17 111.5(3) . . Y C22 C21 C17 109.8(3) . . Y O4 C22 C21 110.4(3) . . Y _diffrn_reflns_theta_full 70.01 _refine_diff_density_max 0.181 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.039 _publ_section_experimental ; Crystal colour: transparent colourless, crystal shape: regular platelet. Profile analysis combining the methods of Lehman & Larsen (1974) and Grant & Gabe (1978). Empirical absorption correction using EMPABS (North, Phillips & Mathews, 1968). Data collection parameters: \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.48 + 0.20tan\q)\%, range: 0.73\%-1.54\%, aperture (1.41 + 0.17tan\q)mm., range: 1.42-1.88mm. Maximum scan time: 30 sec/reflection. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.0980P)^2^+0.1768P] where P=(Fo^2^+2Fc^2^)/3 ; data_NAVRRT _database_code_CSD 190458 _audit_creation_method 'SHELXL, adapted and expanded' _audit_creation_date 2000-01-03 _chemical_name_systematic ; (3R,4S)-piperidinium (S)-Mosher carboxylate ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 F4 N O4' _chemical_formula_weight 457.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.9615(2) _cell_length_b 8.97716(19) _cell_length_c 14.7286(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.862(5) _cell_angle_gamma 90.00 _cell_volume 1159.59(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 37.013 _cell_measurement_theta_max 43.534 _exptl_crystal_description 'regular lump' _exptl_crystal_colour 'colorless transparant' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.14 #_exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.943 _exptl_absorpt_correction_type experimental #_exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.896 _exptl_absorpt_correction_T_max 1.191 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD4' _diffrn_measurement_method \w/2\q-scan _diffrn_special_details ; \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.60 + 0.20tan\q)\%, range: 0.91\%-1.71\%, aperture (1.80 + 0.17tan\q)mm., range: 1.81-2.27mm. Maximum scan time: 30 sec/reflection. ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% 1.751 _diffrn_reflns_number 2411 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0110 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 69.86 _reflns_number_total 2273 _reflns_number_gt 2119 _reflns_number_observed 2119 _reflns_threshold_expression >2sigma(I) _reflns_observed_criterion >2sigma(I) _computing_data_collection ; CAD4 EXPRESS (Enraf-Nonius, 1994) ; #_computing_cell_refinement #; #CAD4 EXPRESS (Enraf-Nonius, 1994) #; _computing_data_reduction ; local programs (Smits et al., 1988), profile analysis (Lehman & Larsen, 1974, Grant & Gabe, 1978), EMPABS (North et al., 1968) ; _computing_structure_solution ; CRUNCH (de Gelder et al., 1993), ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLUTON (Spek, 1993), PLATON (Spek, 1990, 1995) ; _computing_publication_material ? _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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0628P)^2^+0.0878P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0074(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_Flack -0.18(17) _refine_ls_number_reflns 2273 _refine_ls_number_parameters 398 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0337 _refine_ls_R_factor_obs 0.0337 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_all 0.0936 _refine_ls_wR_factor_gt 0.0911 _refine_ls_wR_factor_obs 0.0911 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_goodness_of_fit_all 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_shift/esd_mean 0.000 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 F1 F 0.3261(2) 0.9489(2) 0.69351(12) 0.0857(5) Uani 1 d . . . F2 F 0.4715(2) 0.7891(3) 0.64754(12) 0.0947(6) Uani 1 d . . . F3 F 0.5247(2) 0.8669(3) 0.78732(14) 0.0969(6) Uani 1 d . . . F4 F -0.55615(19) 0.3242(4) 0.52548(13) 0.1199(10) Uani 1 d . . . O1 O 0.3890(2) 0.5594(2) 0.74107(12) 0.0651(5) Uani 1 d . . . O2 O 0.2596(3) 0.8563(2) 0.86457(13) 0.0729(5) Uani 1 d . . . O3 O 0.2681(2) 0.6138(2) 0.89262(11) 0.0654(5) Uani 1 d . . . O4 O -0.1384(4) 0.4186(3) 0.98713(18) 0.1041(10) Uani 1 d . . . H41 H -0.173(5) 0.400(6) 1.028(3) 0.108(14) Uiso 1 d . . . N1 N 0.2809(2) 0.3195(3) 0.90133(14) 0.0599(5) Uani 1 d . . . H1 H 0.282(3) 0.405(4) 0.884(2) 0.059(8) Uiso 1 d . . . C1 C 0.3130(3) 0.6964(3) 0.74561(15) 0.0555(5) Uani 1 d . . . C2 C 0.1659(3) 0.6878(3) 0.67188(15) 0.0564(5) Uani 1 d . . . C3 C 0.0350(3) 0.7624(3) 0.68138(19) 0.0677(6) Uani 1 d . . . H3 H 0.033(3) 0.807(4) 0.737(2) 0.065(7) Uiso 1 d . . . C4 C -0.0938(4) 0.7608(4) 0.6096(2) 0.0816(8) Uani 1 d . . . H4 H -0.180(4) 0.818(5) 0.620(3) 0.103(12) Uiso 1 d . . . C5 C -0.0913(4) 0.6872(5) 0.5293(2) 0.0839(9) Uani 1 d . . . H5 H -0.179(4) 0.696(5) 0.473(3) 0.103(11) Uiso 1 d . . . C6 C 0.0358(4) 0.6110(5) 0.51974(19) 0.0877(9) Uani 1 d . . . H6 H 0.038(5) 0.550(7) 0.461(3) 0.128(16) Uiso 1 d . . . C7 C 0.1650(4) 0.6111(4) 0.59033(17) 0.0729(7) Uani 1 d . . . H7 H 0.255(4) 0.555(4) 0.589(2) 0.081(9) Uiso 1 d . . . C8 C 0.4085(3) 0.8253(4) 0.71879(19) 0.0720(7) Uani 1 d . . . C9 C 0.2777(3) 0.7246(3) 0.84387(16) 0.0542(5) Uani 1 d . . . C10 C 0.5388(4) 0.5432(5) 0.7971(3) 0.0849(9) Uani 1 d . . . H10A H 0.615(4) 0.607(5) 0.770(2) 0.094(10) Uiso 1 d . . . H10B H 0.575(5) 0.440(6) 0.793(3) 0.113(13) Uiso 1 d . . . H10C H 0.539(4) 0.572(5) 0.859(2) 0.082(9) Uiso 1 d . . . C11 C -0.1589(3) 0.2487(3) 0.71803(16) 0.0592(6) Uani 1 d . . . C12 C -0.2692(4) 0.1390(5) 0.6963(2) 0.0848(9) Uani 1 d . . . H12 H -0.247(4) 0.039(5) 0.724(2) 0.085(10) Uiso 1 d . . . C13 C -0.4021(4) 0.1644(6) 0.6305(3) 0.1014(13) Uani 1 d . . . H13 H -0.482(5) 0.081(7) 0.620(3) 0.135(16) Uiso 1 d . . . C14 C -0.4238(3) 0.2975(5) 0.58827(18) 0.0846(10) Uani 1 d . . . C15 C -0.3187(4) 0.4085(5) 0.6053(2) 0.0840(9) Uani 1 d . . . H15 H -0.329(5) 0.504(6) 0.578(3) 0.111(14) Uiso 1 d . . . C16 C -0.1852(3) 0.3820(4) 0.67115(19) 0.0696(7) Uani 1 d . . . H16 H -0.110(3) 0.454(4) 0.680(2) 0.072(8) Uiso 1 d . . . C17 C -0.0142(3) 0.2223(3) 0.79035(16) 0.0576(5) Uani 1 d . . . H17 H -0.018(3) 0.124(4) 0.8132(19) 0.066(7) Uiso 1 d . . . C18 C 0.1275(3) 0.2458(3) 0.74930(17) 0.0618(6) Uani 1 d . . . H18A H 0.128(3) 0.174(4) 0.698(2) 0.068(8) Uiso 1 d . . . H18B H 0.128(3) 0.341(4) 0.7248(19) 0.060(7) Uiso 1 d . . . C19 C 0.2739(3) 0.2198(3) 0.8196(2) 0.0669(6) Uani 1 d . . . H19A H 0.277(3) 0.120(5) 0.848(2) 0.075(9) Uiso 1 d . . . H19B H 0.362(3) 0.249(4) 0.797(2) 0.069(8) Uiso 1 d . . . C20 C 0.1459(3) 0.2974(3) 0.94447(16) 0.0630(6) Uani 1 d . . . H20A H 0.153(3) 0.366(4) 0.993(2) 0.062(7) Uiso 1 d . . . H20B H 0.139(5) 0.193(6) 0.967(3) 0.104(12) Uiso 1 d . . . C21 C -0.0039(3) 0.3237(3) 0.87590(15) 0.0544(5) Uani 1 d . . . H21 H -0.007(3) 0.427(4) 0.8547(17) 0.056(7) Uiso 1 d . . . C22 C -0.1348(4) 0.2997(4) 0.92596(19) 0.0696(7) Uani 1 d . . . H22A H -0.228(4) 0.305(5) 0.883(2) 0.094(11) Uiso 1 d . . . H22B H -0.132(3) 0.197(4) 0.959(2) 0.074(8) Uiso 1 d . . . C23 C 0.4263(4) 0.2979(6) 0.9705(3) 0.0916(10) Uani 1 d . . . H23A H 0.421(5) 0.203(7) 0.994(3) 0.114(15) Uiso 1 d . . . H23B H 0.416(5) 0.358(6) 1.021(3) 0.105(13) Uiso 1 d . . . H23C H 0.505(6) 0.311(6) 0.938(3) 0.123(15) Uiso 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 0.1163(13) 0.0620(10) 0.0906(11) 0.0110(9) 0.0489(10) -0.0071(9) F2 0.1092(12) 0.1060(14) 0.0874(10) 0.0007(11) 0.0633(10) -0.0073(11) F3 0.0903(11) 0.1086(15) 0.0967(12) -0.0079(12) 0.0304(10) -0.0373(11) F4 0.0714(9) 0.203(3) 0.0767(10) 0.0018(14) -0.0034(8) -0.0297(15) O1 0.0679(9) 0.0692(11) 0.0599(9) -0.0067(8) 0.0167(7) 0.0158(8) O2 0.1164(15) 0.0514(11) 0.0608(9) -0.0058(8) 0.0413(10) -0.0040(10) O3 0.0922(12) 0.0557(10) 0.0542(9) 0.0045(8) 0.0287(8) 0.0018(8) O4 0.173(3) 0.0703(15) 0.0960(15) -0.0094(12) 0.0904(18) -0.0090(14) N1 0.0663(11) 0.0536(13) 0.0562(10) 0.0089(9) 0.0042(8) 0.0073(9) C1 0.0672(12) 0.0523(13) 0.0519(11) -0.0020(10) 0.0236(10) 0.0019(10) C2 0.0692(12) 0.0537(13) 0.0491(10) 0.0051(10) 0.0184(9) 0.0055(10) C3 0.0755(15) 0.0641(16) 0.0659(14) -0.0079(12) 0.0204(12) 0.0075(12) C4 0.0751(16) 0.082(2) 0.0864(18) 0.0062(16) 0.0142(14) 0.0170(15) C5 0.0896(18) 0.092(2) 0.0648(16) 0.0111(16) 0.0045(14) 0.0082(18) C6 0.114(3) 0.093(2) 0.0535(15) -0.0053(15) 0.0108(15) 0.013(2) C7 0.0856(17) 0.083(2) 0.0511(12) -0.0028(13) 0.0170(11) 0.0173(16) C8 0.0797(15) 0.078(2) 0.0670(14) -0.0005(14) 0.0350(13) -0.0099(15) C9 0.0599(11) 0.0555(14) 0.0510(11) -0.0011(10) 0.0204(9) -0.0026(10) C10 0.0688(17) 0.107(3) 0.0804(19) -0.0025(19) 0.0195(14) 0.0232(18) C11 0.0664(13) 0.0635(15) 0.0522(11) -0.0078(10) 0.0224(10) -0.0125(11) C12 0.095(2) 0.081(2) 0.0817(18) -0.0031(17) 0.0251(16) -0.0335(18) C13 0.086(2) 0.132(4) 0.086(2) -0.013(2) 0.0178(17) -0.052(2) C14 0.0643(14) 0.135(3) 0.0554(13) -0.0071(18) 0.0134(11) -0.0255(18) C15 0.0702(16) 0.107(3) 0.0698(16) 0.0110(17) 0.0037(13) -0.0102(16) C16 0.0647(14) 0.0735(18) 0.0676(14) 0.0058(13) 0.0062(11) -0.0147(13) C17 0.0758(14) 0.0459(13) 0.0547(11) 0.0008(10) 0.0217(10) -0.0028(10) C18 0.0712(14) 0.0632(16) 0.0543(12) -0.0081(11) 0.0206(10) 0.0018(12) C19 0.0700(14) 0.0569(16) 0.0760(16) -0.0013(13) 0.0203(12) 0.0101(12) C20 0.0838(15) 0.0581(15) 0.0471(11) 0.0077(11) 0.0133(10) 0.0048(12) C21 0.0730(12) 0.0467(13) 0.0473(10) 0.0040(9) 0.0206(9) 0.0021(10) C22 0.0878(17) 0.0685(17) 0.0613(13) 0.0025(13) 0.0354(13) 0.0008(14) C23 0.0819(19) 0.108(3) 0.0759(19) 0.023(2) -0.0044(16) 0.017(2) _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 C8 1.343(4) . Y F2 C8 1.330(3) . Y F3 C8 1.346(4) . Y F4 C14 1.367(3) . Y O1 C1 1.414(3) . Y O1 C10 1.431(4) . Y O2 C9 1.241(3) . Y O3 C9 1.240(3) . Y O4 C22 1.402(4) . Y N1 C20 1.491(3) . Y N1 C19 1.492(4) . Y N1 C23 1.492(4) . Y C1 C2 1.528(3) . Y C1 C8 1.538(4) . Y C1 C9 1.564(3) . Y C2 C3 1.383(4) . Y C2 C7 1.383(4) . Y C3 C4 1.396(4) . Y C4 C5 1.360(5) . Y C5 C6 1.360(5) . Y C6 C7 1.388(4) . Y C11 C16 1.377(4) . Y C11 C12 1.385(4) . Y C11 C17 1.518(3) . Y C12 C13 1.391(5) . Y C13 C14 1.343(6) . Y C14 C15 1.359(5) . Y C15 C16 1.397(4) . Y C17 C18 1.529(3) . Y C17 C21 1.542(3) . Y C18 C19 1.513(4) . Y C20 C21 1.523(4) . Y C21 C22 1.524(3) . Y 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 C1 O1 C10 117.7(2) . . Y C20 N1 C19 111.2(2) . . Y C20 N1 C23 111.3(2) . . Y C19 N1 C23 111.1(3) . . Y O1 C1 C2 106.04(19) . . Y O1 C1 C8 110.09(19) . . Y C2 C1 C8 107.4(2) . . Y O1 C1 C9 112.05(19) . . Y C2 C1 C9 110.89(18) . . Y C8 C1 C9 110.2(2) . . Y C3 C2 C7 118.4(2) . . Y C3 C2 C1 122.0(2) . . Y C7 C2 C1 119.5(2) . . Y C2 C3 C4 120.4(3) . . Y C5 C4 C3 120.3(3) . . Y C4 C5 C6 119.9(3) . . Y C5 C6 C7 120.6(3) . . Y C2 C7 C6 120.4(3) . . Y F2 C8 F1 106.3(2) . . Y F2 C8 F3 105.7(2) . . Y F1 C8 F3 106.0(3) . . Y F2 C8 C1 111.6(2) . . Y F1 C8 C1 112.9(2) . . Y F3 C8 C1 113.7(2) . . Y O3 C9 O2 126.5(2) . . Y O3 C9 C1 117.2(2) . . Y O2 C9 C1 116.3(2) . . Y C16 C11 C12 117.5(3) . . Y C16 C11 C17 121.4(2) . . Y C12 C11 C17 121.1(3) . . Y C11 C12 C13 120.9(4) . . Y C14 C13 C12 119.3(3) . . Y C13 C14 C15 122.6(3) . . Y C13 C14 F4 119.5(3) . . Y C15 C14 F4 117.9(4) . . Y C14 C15 C16 117.7(4) . . Y C11 C16 C15 122.0(3) . . Y C11 C17 C18 111.11(19) . . Y C11 C17 C21 112.3(2) . . Y C18 C17 C21 109.1(2) . . Y C19 C18 C17 112.5(2) . . Y N1 C19 C18 110.3(2) . . Y N1 C20 C21 112.25(18) . . Y C20 C21 C22 108.57(19) . . Y C20 C21 C17 110.3(2) . . Y C22 C21 C17 112.9(2) . . Y O4 C22 C21 109.0(2) . . Y _diffrn_reflns_theta_full 69.86 _refine_diff_density_max 0.164 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.030 _publ_section_experimental ; Crystal colour: colorless transparant, crystal shape: regular lump. Profile analysis combining the methods of Lehman & Larsen (1974) and Grant & Gabe (1978). Empirical absorption correction using EMPABS (North, Phillips & Mathews, 1968). Data collection parameters: \w/2\q-scan with variable scan width, variable scan speed and variable aperture. Scan width (0.60 + 0.20tan\q)\%, range: 0.91\%-1.71\%, aperture (1.80 + 0.17tan\q)mm., range: 1.81-2.27mm. Maximum scan time: 30 sec/reflection. Least-squares refinement using calculated weights: w=1/[\s^2^(Fo^2^)+(0.0628P)^2^+0.0878P] where P=(Fo^2^+2Fc^2^)/3 ;