#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/17/2101708.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2101708
loop_
_publ_author_name
'Larsen, S.'
'Marthi, K.'
_publ_section_title
;
 Structures of the Optically Active Monofluoro-Substituted Mandelic
 Acids: Relation to Their Racemic Counterparts and Thermochemical
 Properties
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              280
_journal_page_last               292
_journal_paper_doi               10.1107/S0108768196013419
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety
;
FC~6~H~5~CH(OH)COOH
;
_chemical_formula_sum            'C8 H7 F O3'
_chemical_formula_weight         170.14
_chemical_melting_point          425.8
_chemical_name_systematic
;
(R)-(-)-para-fluoromandelic acid
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 107.56(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.464(2)
_cell_length_b                   5.8518(13)
_cell_length_c                   15.868(2)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    122.0(5)
_cell_measurement_theta_max      21.32
_cell_measurement_theta_min      19.44
_cell_volume                     749.3(3)
_computing_cell_refinement       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'DREADD (Blessing, 1987)'
_computing_molecular_graphics    'OrtepII (Johnson, 1976) '
_computing_publication_material
;
SHELXL-93 (Sheldrick, 1995) and local programs
;
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1995)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      122.0(5)
_diffrn_measurement_device       'Enraf Nonius CAD4'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            3552
_diffrn_reflns_theta_max         45.29
_diffrn_reflns_theta_min         1.35
_diffrn_standards_decay_%        0.2
_diffrn_standards_interval_time  166.7
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    none
_exptl_crystal_description       cubic
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.309
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.121
_refine_ls_goodness_of_fit_obs   1.099
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.245
_refine_ls_restrained_S_obs      1.099
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_obs          0.0356
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0497P)²+0.1016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1134
_refine_ls_wR_factor_obs         0.0948
_reflns_number_observed          2977
_reflns_number_total             3307
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ab0363.cif
_cod_data_source_block           OP
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.1016P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.1016P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2101708
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'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
F 0.0436(3) 0.0267(3) 0.0112(2) -0.0011(3) 0.0026(2) -0.0015(2)
O1 0.0194(2) 0.0099(2) 0.0226(3) 0.0003(2) -0.0027(2) 0.0005(2)
O2 0.0153(2) 0.0139(2) 0.0183(2) -0.0021(2) -0.0027(2) -0.0017(2)
O3 0.0238(3) 0.0100(2) 0.0198(2) -0.0013(2) -0.0074(2) 0.0026(2)
C1 0.0142(2) 0.0100(2) 0.0111(2) -0.0018(2) 0.0018(2) -0.0002(2)
C2 0.0147(2) 0.0101(2) 0.0122(2) -0.0023(2) 0.0006(2) 0.0008(2)
C3 0.0131(2) 0.0106(2) 0.0122(2) -0.0010(2) 0.0008(2) -0.0003(2)
C4 0.0135(2) 0.0264(4) 0.0139(2) -0.0012(3) -0.0003(2) 0.0003(3)
C5 0.0189(3) 0.0309(4) 0.0143(2) -0.0019(3) -0.0022(2) -0.0006(3)
C6 0.0280(3) 0.0165(3) 0.0116(2) 0.0000(3) 0.0021(2) -0.0005(2)
C7 0.0243(3) 0.0285(4) 0.0169(3) 0.0005(4) 0.0078(2) -0.0019(3)
C8 0.0160(2) 0.0258(4) 0.0161(2) -0.0001(3) 0.0038(2) -0.0012(3)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
F 0.25325(12) 0.22906(14) -0.00442(4) 0.02841(14) Uani d 1 F
O1 0.43378(8) 0.67669(11) 0.36506(5) 0.01932(12) Uani d 1 O
H1 0.479(2) 0.802(4) 0.3854(12) 0.029 Uiso d 1 H
O2 0.66203(7) 0.50842(11) 0.45392(4) 0.01756(10) Uani d 1 O
O3 0.54978(9) 0.09045(11) 0.40495(5) 0.02094(13) Uani d 1 O
H3 0.629(2) 0.128(5) 0.4438(13) 0.031 Uiso d 1 H
C1 0.52524(8) 0.49977(12) 0.39993(4) 0.01222(9) Uani d 1 C
C2 0.44132(9) 0.27279(12) 0.36670(4) 0.01308(10) Uani d 1 C
H2 0.3357(18) 0.262(4) 0.3867(10) 0.016 Uiso d 1 H
C3 0.39024(8) 0.25790(12) 0.26699(4) 0.01264(9) Uani d 1 C
C4 0.22379(9) 0.2540(2) 0.21803(5) 0.01890(13) Uani d 1 C
H4 0.143(2) 0.255(4) 0.2468(12) 0.023 Uiso d 1 H
C5 0.17592(11) 0.2436(2) 0.12596(5) 0.0230(2) Uani d 1 C
H5 0.060(2) 0.242(4) 0.0873(13) 0.028 Uiso d 1 H
C6 0.29861(12) 0.2381(2) 0.08526(5) 0.01957(13) Uani d 1 C
C7 0.46518(12) 0.2404(2) 0.13146(6) 0.0229(2) Uani d 1 C
H7 0.549(2) 0.226(4) 0.1030(13) 0.027 Uiso d 1 H
C8 0.51075(10) 0.2496(2) 0.22336(5) 0.01953(13) Uani d 1 C
H8 0.630(2) 0.250(4) 0.2606(13) 0.023 Uiso d 1 H
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 0.0000 0.0000 '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 0.0060 '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_publ_flag
C1 O1 H1 112.4(14) no
C2 O3 H3 114.3(19) no
O2 C1 O1 125.45(7) yes
O2 C1 C2 121.71(7) yes
O1 C1 C2 112.84(6) yes
O3 C2 C3 110.37(6) yes
O3 C2 C1 109.49(6) yes
C3 C2 C1 111.64(6) yes
O3 C2 H2 109.2(11) no
C3 C2 H2 108.4(9) no
C1 C2 H2 107.7(11) no
C4 C3 C8 119.45(7) yes
C4 C3 C2 120.54(7) yes
C8 C3 C2 120.01(6) yes
C3 C4 C5 120.79(8) yes
C3 C4 H4 119.9(11) no
C5 C4 H4 119.3(11) no
C6 C5 C4 118.02(7) yes
C6 C5 H5 117.2(11) no
C4 C5 H5 124.8(11) no
F C6 C5 118.47(8) yes
F C6 C7 118.54(9) yes
C5 C6 C7 122.99(7) yes
C6 C7 C8 118.22(8) yes
C6 C7 H7 122.3(13) no
C8 C7 H7 119.3(13) no
C7 C8 C3 120.52(7) yes
C7 C8 H8 121.8(10) no
C3 C8 H8 117.6(11) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F C6 1.3585(10) yes
O1 C1 1.3111(10) yes
O1 H1 0.85(2) no
O2 C1 1.2159(9) yes
O3 C2 1.4190(10) yes
O3 H3 0.79(2) no
C1 C2 1.5234(10) yes
C2 C3 1.5116(10) yes
C2 H2 1.037(15) no
C3 C4 1.3887(10) yes
C3 C8 1.3958(11) yes
C4 C5 1.3946(11) yes
C4 H4 0.93(2) no
C5 C6 1.3789(14) yes
C5 H5 0.99(2) no
C6 C7 1.3789(13) yes
C7 C8 1.3924(12) yes
C7 H7 0.95(2) no
C8 H8 1.01(2) 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_publ_flag
O2 C1 C2 O3 -2.77(9) yes
C1 C2 C3 C4 -112.69(9) yes
C1 C2 C3 C8 66.82(9) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5362474
