A Novel Crystallization-Induced Diastereomeric Transformation Based on a Reversible Carbon-Sulfur Bond Formation. Application to the Synthesis of a γ-Secretase Inhibitor
Antony J. Davies; Jeremy P. Scott; Brian C. Bishop; Karel M. J. Brands; Sarah E. Brewer; Jimmy O. DaSilva; Peter G. Dormer; Ulf-H. Dolling; Andrew D. Gibb; Deborah C. Hammond; David R. Lieberman; Michael Palucki; Joseph F. Payack; Journal of Organic Chemistry 72 (2007) 4864–4871; doi:10.1021/jo0705925

data_4023966
_publ_section_title
;
 A Novel Crystallization-Induced Diastereomeric Transformation
 Based on a Reversible Carbon-Sulfur Bond Formation. Application to
 the Synthesis of a \g-Secretase Inhibitor
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4864
_journal_page_last               4871
_journal_paper_doi               10.1021/jo0705925
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C21 H21 Cl F2 O2 S'
_chemical_formula_sum            'C21 H21 Cl F2 O2 S'
_chemical_formula_weight         410.89
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 96.238(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.617(12)
_cell_length_b                   9.770(4)
_cell_length_c                   14.938(6)
_cell_measurement_reflns_used    3650
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.11
_cell_measurement_theta_min      2.21
_cell_volume                     4007(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20554
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.326
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+2.9173P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1475
_reflns_number_gt                2747
_reflns_number_total             4069
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0705925si20070322_073922.cif
_cod_data_source_block           jrc2311n
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4023966