Enantiodiscrimination in NMR spectra and X-ray structures of diastereomeric salts of trans-4-(4-fluorophenyl)-3-hydroxymethyl-1-methylpiperidine with (S)-Mosher acid
Hana Navrátilová; René de Gelder; Zdeněk Kříž; J. Chem. Soc., Perkin Trans. 2  (2002) 2093–2099; doi:10.1039/b207176b

data_7204500
_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
;
_journal_issue                   12
_journal_name_full               'J. Chem. Soc., Perkin Trans. 2'
_journal_page_first              2093
_journal_page_last               2099
_journal_paper_doi               10.1039/b207176b
_journal_year                    2002
_chemical_formula_sum            'C23 H27 F4 N O4'
_chemical_formula_weight         457.46
_chemical_name_systematic
; 
(3S,4R)-piperidinium (S)-Mosher carboxylate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2000-01-03
_audit_creation_method           'SHELXL, adapted and expanded'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.441(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.30900(14)
_cell_length_b                   12.0081(4)
_cell_length_c                   13.0629(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.486
_cell_measurement_theta_min      40.524
_cell_volume                     1146.46(5)
_computing_data_collection
;
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_molecular_graphics
;
PLUTON (Spek, 1993),
PLATON (Spek, 1990, 1995)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
CRUNCH (de Gelder et al., 1993),
;
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Nonius CAD4'
_diffrn_measurement_method       \w/2\q-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0120
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2378
_diffrn_reflns_theta_full        70.01
_diffrn_reflns_theta_max         70.01
_diffrn_reflns_theta_min         3.38
_diffrn_standards_decay_%        2.278
_diffrn_standards_interval_time  7200
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_T_max  1.288
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   experimental
_exptl_crystal_colour            'transparent colourless'
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'regular platelet'
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_Flack   -0.1(3)
_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_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.153
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         2279
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0468
_refine_ls_R_factor_obs          0.0468
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0980P)^2^+0.1768P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1573
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_obs         0.1535
_refine_ls_wR_factor_ref         0.1573
_reflns_number_gt                2136
_reflns_number_observed          2136
_reflns_number_total             2279
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b207176b.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (47
times).

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (33 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7204500