#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/45/7204501.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204501
loop_
_publ_author_name
'Hana Navrátilová'
'René de Gelder'
'Zdeněk Kříž'
_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
;
(3R,4S)-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                 101.862(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.9615(2)
_cell_length_b                   8.97716(19)
_cell_length_c                   14.7286(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      43.534
_cell_measurement_theta_min      37.013
_cell_volume                     1159.60(7)
_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       ω/2θ-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  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0110
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2411
_diffrn_reflns_theta_full        69.86
_diffrn_reflns_theta_max         69.86
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        1.751
_diffrn_standards_interval_time  3600
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.943
_exptl_absorpt_correction_T_max  1.191
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   experimental
_exptl_crystal_colour            'colorless transparant'
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'regular lump'
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_Flack   -0.18(17)
_refine_ls_extinction_coef       0.0074(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.036
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0337
_refine_ls_R_factor_obs          0.0337
_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/[σ²(Fo²)+(0.0628P)²+0.0878P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0936
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_obs         0.0911
_refine_ls_wR_factor_ref         0.0936
_reflns_number_gt                2119
_reflns_number_observed          2119
_reflns_number_total             2273
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b207176b.txt
_cod_data_source_block           NAVRRT
_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_cell_volume        1159.59(7)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7204501
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_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'
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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21189751
