Are the Crystal Structures of Enantiopure and Racemic Mandelic Acids Determined by Kinetics or Thermodynamics?
Hylton, Rebecca K.; Tizzard, Graham J.; Threlfall, Terence L.; Ellis, Amy L.; Coles, Simon J.; Seaton, Colin C.; Schulze, Eric; Lorenz, Heike; Seidel-Morgenstern, Andreas; Stein, Matthias; Price, Sarah L.; Journal of the American Chemical Society 137 (2015) 11095–11104; doi:10.1021/jacs.5b05938

data_4124301
_publ_section_title
;
 Are the Crystal Structures of Enantiopure and Racemic Mandelic Acids
 Determined by Kinetics or Thermodynamics?
;
_journal_issue                   34
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11095
_journal_page_last               11104
_journal_paper_doi               10.1021/jacs.5b05938
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C8 H6 Cl F O3'
_chemical_formula_sum            'C8 H6 Cl F O3'
_chemical_formula_weight         204.58
_chemical_name_systematic
; 
 (S)-2-chloro 4-fluoromandelic acid 
;
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.477(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8577(8)
_cell_length_b                   7.8314(6)
_cell_length_c                   14.1039(12)
_cell_measurement_reflns_used    2587
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3827
_cell_measurement_theta_min      2.9905
_cell_volume                     836.44(13)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3367
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_details
;
  1 omega  -35.00    1.00   1.0000    5.7900
omega____ theta____ kappa____ phi______ frames
    -      -21.2308  -89.0000  -25.0000 36

  2 omega   34.00  116.00   1.0000    5.7900
omega____ theta____ kappa____ phi______ frames
    -       22.6371  179.0000 -180.0000 82

  3 omega   -3.00  113.00   1.0000    5.7900
omega____ theta____ kappa____ phi______ frames
    -       22.6371   37.0000  -30.0000 116

  4 omega  -10.00   17.00   1.0000    5.7900
omega____ theta____ kappa____ phi______ frames
    -       22.6371   89.0000  -90.0000 27

  5 omega    3.00  121.00   1.0000    5.7900
omega____ theta____ kappa____ phi______ frames
    -       22.6371   77.0000 -180.0000 118
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0788
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5570
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81692
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                2620
_reflns_number_total             3496
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b05938_si_001.cif
_cod_data_source_block           S_2Cl4FMA
_cod_depositor_comments
'Adding full bibliography for 4124298--4124305.cif.'
_cod_database_code               4124301