#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:08:31 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180289 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/03/7150345.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_7150345
loop_
_publ_author_name
'Charrier, Jean-Damien'
'Hadfield, David S.'
'Hitchcock, Peter B.'
'Young, Douglas W.'
_publ_section_title
;
 Synthesis of (2S,4S)- and (2S,4R)-5-fluoroleucine and
 (2S,4S)-[5,5-2H2]-5-fluoroleucine.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              474
_journal_page_last               482
_journal_paper_doi               10.1039/b314933a
_journal_volume                  2
_journal_year                    2004
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C6 H12 F1 N1 O2'
_chemical_formula_structural     'C6 H12 F N O2'
_chemical_formula_sum            'C6 H12 F N O2'
_chemical_formula_weight         149.17
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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_conform_dict_location
ftp://ftp.iucr.org/cifdics/cif_core_2.1beta5.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1beta5
_audit_creation_date             2000-04-18T09:07:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 93.10(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.637(4)
_cell_length_b                   5.314(3)
_cell_length_c                   14.574(7)
_cell_measurement_reflns_used    5334
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      22.722
_cell_measurement_theta_min      3.705
_cell_measurement_wavelength     0.71073
_cell_volume                     745.3(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1751
_diffrn_reflns_av_sigmaI/netI    0.23
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3162
_diffrn_reflns_theta_full        22.77
_diffrn_reflns_theta_max         22.77
_diffrn_reflns_theta_min         4.08
_exptl_absorpt_coefficient_mu    0.11
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.33
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.3
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1844
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.2149
_refine_ls_R_factor_gt           0.1075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0852P)²+0.4395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2256
_refine_ls_wR_factor_ref         0.2851
_reflns_number_gt                853
_reflns_number_total             1844
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b314933a.txt
_cod_data_source_block           (2)-apr1600
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7150345
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.3422(13) 0.292(3) 0.5228(8) 0.158(6) Uani 1 1 d . . .
O1 O -0.2288(9) 0.2059(16) 0.8802(6) 0.058(3) Uani 1 1 d . . .
O2 O -0.1511(8) 0.5904(16) 0.9136(6) 0.049(2) Uani 1 1 d . . .
N1 N -0.4119(9) 0.7889(19) 0.9012(7) 0.049(3) Uani 1 1 d . . .
C1 C -0.2471(14) 0.441(3) 0.8843(8) 0.047(4) Uani 1 1 d . . .
C2 C -0.3816(11) 0.549(2) 0.8494(8) 0.036(3) Uani 1 1 d . . .
H2 H -0.4572 0.4245 0.859 0.043 Uiso 1 1 calc R . .
C3 C -0.3847(13) 0.622(3) 0.7467(8) 0.053(4) Uani 1 1 d . . .
H3B H -0.4705 0.7194 0.7314 0.064 Uiso 1 1 calc R . .
H3A H -0.3046 0.7336 0.7365 0.064 Uiso 1 1 calc R . .
C4 C -0.3797(14) 0.399(4) 0.6818(9) 0.070(5) Uani 1 1 d . . .
H4 H -0.3038 0.2809 0.7029 0.084 Uiso 1 1 calc R . .
C5 C -0.3501(19) 0.509(4) 0.5890(9) 0.103(7) Uani 1 1 d . . .
H5B H -0.4252 0.6263 0.5682 0.123 Uiso 1 1 calc R . .
H5A H -0.2611 0.6026 0.5929 0.123 Uiso 1 1 calc R . .
C6 C -0.5184(17) 0.264(3) 0.6761(11) 0.087(5) Uani 1 1 d . . .
H6C H -0.5361 0.1914 0.7361 0.131 Uiso 1 1 calc R . .
H6B H -0.5164 0.1297 0.6301 0.131 Uiso 1 1 calc R . .
H6A H -0.5923 0.3839 0.6583 0.131 Uiso 1 1 calc R . .
O1A O 0.2776(8) -0.1883(18) 0.8646(6) 0.055(3) Uani 1 1 d . . .
O2A O 0.3676(8) 0.1785(16) 0.9152(5) 0.051(3) Uani 1 1 d . . .
N1A N 0.1159(10) 0.395(2) 0.9302(6) 0.044(3) Uani 1 1 d . . .
C1A C 0.2639(13) 0.035(3) 0.8830(9) 0.048(4) Uani 1 1 d . . .
C2A C 0.1270(12) 0.171(2) 0.8667(8) 0.043(4) Uani 1 1 d . . .
H2A H 0.0501 0.0514 0.8788 0.052 Uiso 1 1 calc R . .
C3A C 0.1081(13) 0.261(2) 0.7663(8) 0.048(4) Uani 1 1 d . B .
H3A1 H 0.0214 0.3609 0.76 0.057 Uiso 1 1 calc R . .
H3A2 H 0.1859 0.3756 0.7541 0.057 Uiso 1 1 calc R . .
C4A C 0.1015(14) 0.060(3) 0.6931(11) 0.061(4) Uani 1 1 d . . .
H4A H 0.1844 -0.0505 0.7057 0.074 Uiso 1 1 calc R A 1
C6A C -0.0241(16) -0.106(3) 0.6977(11) 0.080(5) Uani 1 1 d . B .
H6A1 H -0.0208 -0.2384 0.651 0.12 Uiso 1 1 calc R . .
H6A2 H -0.1084 -0.0055 0.6865 0.12 Uiso 1 1 calc R . .
H6A3 H -0.0249 -0.1837 0.7588 0.12 Uiso 1 1 calc R . .
C5A C 0.115(4) 0.167(11) 0.598(3) 0.14(3) Uani 0.76(3) 1 d P B 1
H5A1 H 0.1989 0.2731 0.5956 0.173 Uiso 0.76(3) 1 calc PR B 1
H5A2 H 0.1201 0.0302 0.552 0.173 Uiso 0.76(3) 1 calc PR B 1
F1A F -0.0059(19) 0.311(3) 0.5812(9) 0.111(7) Uani 0.76(3) 1 d P B 1
C5AA C 0.087(9) 0.190(14) 0.599(5) 0.011(18) Uiso 0.24(3) 1 d P B 2
F1AA F 0.189(5) 0.422(11) 0.576(3) 0.102(19) Uiso 0.24(3) 1 d P B 2
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'
N N 0.0061 0.0033 '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_
_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
O1 C1 O2 122.0(13) . . ?
O1 C1 C2 119.2(12) . . ?
O2 C1 C2 118.7(12) . . ?
C1 C2 N1 110.0(10) . . ?
C1 C2 C3 113.6(10) . . ?
N1 C2 C3 106.1(10) . . ?
C4 C3 C2 114.1(11) . . ?
C5 C4 C6 109.9(12) . . ?
C5 C4 C3 105.6(14) . . ?
C6 C4 C3 110.2(12) . . ?
F1 C5 C4 107.2(16) . . ?
O1A C1A O2A 123.3(11) . . ?
O1A C1A C2A 122.2(14) . . ?
O2A C1A C2A 114.4(12) . . ?
C1A C2A N1A 111.7(10) . . ?
C1A C2A C3A 110.9(10) . . ?
N1A C2A C3A 109.1(10) . . ?
C4A C3A C2A 116.8(11) . . ?
C6A C4A C3A 112.8(12) . . ?
C6A C4A C5A 112(2) . . ?
C3A C4A C5A 112(3) . . ?
C6A C4A C5AA 106(3) . . ?
C3A C4A C5AA 108(3) . . ?
C5A C4A C5AA 11(4) . . ?
F1A C5A C4A 105(3) . . ?
C4A C5AA F1AA 120(5) . . ?
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 C5 1.51(2) . ?
O1 C1 1.266(15) . ?
O2 C1 1.274(14) . ?
N1 C2 1.516(15) . ?
C1 C2 1.482(16) . ?
C2 C3 1.545(16) . ?
C3 C4 1.52(2) . ?
C4 C5 1.51(2) . ?
C4 C6 1.52(2) . ?
O1A C1A 1.223(15) . ?
O2A C1A 1.325(16) . ?
N1A C2A 1.515(15) . ?
C1A C2A 1.514(16) . ?
C2A C3A 1.539(15) . ?
C3A C4A 1.509(18) . ?
C4A C6A 1.503(18) . ?
C4A C5A 1.51(5) . ?
C4A C5AA 1.53(8) . ?
C5A F1A 1.40(4) . ?
C5AA F1AA 1.62(10) . ?
