Betti's base for crystallization-induced deracemization of substituted aldehydes: synthesis of enantiopure amorolfine and fenpropimorph.
Carella, Andrea; Ramos Ferronatto, Gabriel; Marotta, Emanuela; Mazzanti, Andrea; Righi, Paolo; Paolucci, Claudio; Organic & biomolecular chemistry 15 (2017) 2968–2978; doi:10.1039/c6ob02765b

data_7155521
_publ_section_title
;
 Betti's base for crystallization-induced deracemization of substituted
 aldehydes: synthesis of enantiopure amorolfine and fenpropimorph.
;
_journal_issue                   14
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2968
_journal_page_last               2978
_journal_paper_doi               10.1039/c6ob02765b
_journal_volume                  15
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H19 N O2 S'
_chemical_formula_weight         349.43
_chemical_name_common            'compound (+) 14d'
_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             04/26/2016
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-13 deposited with the CCDC.
2017-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.2280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1265(7)
_cell_length_b                   28.922(3)
_cell_length_c                   11.2917(10)
_cell_measurement_reflns_used    384
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      1.41
_cell_volume                     2234.6(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22626
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.408
_exptl_absorpt_coefficient_mu    0.156
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.039
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 1925 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.879
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         8312
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.880
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.0933
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1745P)^2^+1.7294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2460
_refine_ls_wR_factor_ref         0.2878
_reflns_Friedel_coverage         0.956
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                5133
_reflns_number_total             8312
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob02765b2.cif
_cod_data_source_block           tosilato_a
_cod_depositor_comments          'Adding full bibliography for 7155521.cif.'
_cod_database_code               7155521
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.933
_shelx_estimated_absorpt_t_max   0.970
_shelx_res_checksum              11733