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_4124304
_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 ad
_chemical_formula_moiety         'C8 H7 Cl O3'
_chemical_formula_sum            'C8 H7 Cl O3'
_chemical_formula_weight         186.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.820(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3160(18)
_cell_length_b                   11.855(3)
_cell_length_c                   8.4526(18)
_cell_measurement_temperature    293(2)
_cell_volume                     831.5(3)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_computing_data_collection
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15028
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         3.328
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 2.1 b31 (Rigaku, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 744 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         2919
_refine_ls_number_restraints     481
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0560
_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/[\s^2^(Fo^2^)+(0.0607P)^2^+0.3329P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1416
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2246
_reflns_number_total             2919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b05938_si_001.cif
_cod_data_source_block           S_3ClMA-1
_cod_depositor_comments
'Adding full bibliography for 4124298--4124305.cif.'
_cod_database_code               4124304
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.936
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(O13B) = Uanis(O13A)
Uanis(O12A) = Uanis(O12B)
Uanis(O11A) = Uanis(O11B)
4. Others
 Sof(Cl2B)=Sof(C11B)=Sof(C14B)=Sof(H14B)=Sof(C16B)=Sof(H16B)=Sof(C12B)=
 Sof(H12B)=Sof(C13B)=Sof(C15B)=Sof(H15B)=Sof(O11B)=Sof(H11B)=Sof(O12B)=
 Sof(O13B)=Sof(H13B)=Sof(C18B)=Sof(C17B)=Sof(H17B)=1-FVAR(1)
 Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C18A)=Sof(C17A)=Sof(H17A)=Sof(O11A)=
 Sof(H11A)=Sof(O12A)=Sof(O13A)=Sof(H13A)=Sof(Cl1A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7), C17A(H17A), C17B(H17B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C4(H4), C2(H2), C12A(H12A), C14A(H14A), C15A(H15A),
 C16A(H16A), C14B(H14B), C16B(H16B), C12B(H12B), C15B(H15B)
5.c Fitted hexagon refined as free rotating group:
 C1(C6,C5,C4,C3,C2), C11A(C12A,C13A,C14A,C15A,C16A)
5.d Tetrahedral OH refined with riding coordinates:
 O11A(H11A), O13A(H13A), O11B(H11B), O13B(H13B)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;