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_4124299
_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_formula_moiety         'C8 H6 Cl F O3'
_chemical_formula_sum            'C8 H6 Cl F O3'
_chemical_formula_weight         204.58
_chemical_name_systematic
; 
 (rac) 4-chloro2-fluoromandelic acid 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.955(8)
_cell_angle_beta                 99.289(8)
_cell_angle_gamma                90.680(6)
_cell_formula_units_Z            8
_cell_length_a                   7.7848(5)
_cell_length_b                   13.5323(10)
_cell_length_c                   16.7476(18)
_cell_measurement_reflns_used    3447
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.5608
_cell_measurement_theta_min      2.9992
_cell_volume                     1727.5(3)
_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 0.998
_diffrn_measurement_details
;
  1 omega  -58.00   34.00   1.0000   24.1400
omega____ theta____ kappa____ phi______ frames
    -      -21.0746   77.0000   90.0000 92

  2 omega  -12.00  103.00   1.0000   24.1400
omega____ theta____ kappa____ phi______ frames
    -       22.4808   77.0000  -60.0000 115

  3 omega    1.00   40.00   1.0000   24.1400
omega____ theta____ kappa____ phi______ frames
    -       22.4808   77.0000   30.0000 39

  4 omega   78.00  115.00   1.0000   24.1400
omega____ theta____ kappa____ phi______ frames
    -       22.4808   77.0000   30.0000 37

  5 omega   -2.00  120.00   1.0000   24.1400
omega____ theta____ kappa____ phi______ frames
    -       22.4808   77.0000 -180.0000 122
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\w scans'
_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  0.0511
_diffrn_reflns_av_sigmaI/netI    0.1298
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11569
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.87
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.199
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         7057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1567
_refine_ls_R_factor_gt           0.0865
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1321P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2187
_refine_ls_wR_factor_ref         0.2436
_reflns_number_gt                3446
_reflns_number_total             7057
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b05938_si_001.cif
_cod_data_source_block           RS_4Cl2FMA
_cod_depositor_comments
'Adding full bibliography for 4124298--4124305.cif.'
_cod_database_code               4124299