3-Fluoro-4-hydroxyprolines: Synthesis, Conformational Analysis, and Stereoselective Recognition by the VHL E3 Ubiquitin Ligase for Targeted Protein Degradation.
Testa, Andrea; Lucas, Xavier; Castro, Guilherme V.; Chan, Kwok-Ho; Wright, Jane E.; Runcie, Andrew C.; Gadd, Morgan S.; Harrison, William T. A.; Ko, Eun-Jung; Fletcher, Daniel; Ciulli, Alessio; Journal of the American Chemical Society 140 (2018) 9299–9313; doi:10.1021/jacs.8b05807

data_4132723
_publ_section_title
;
 3-Fluoro-4-hydroxyprolines: Synthesis, Conformational Analysis, and
 Stereoselective Recognition by the VHL E3 Ubiquitin Ligase for Targeted
 Protein Degradation.
;
_journal_issue                   29
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9299
_journal_page_last               9313
_journal_paper_doi               10.1021/jacs.8b05807
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C25 H22 F N O3'
_chemical_formula_sum            'C25 H22 F N O3'
_chemical_formula_weight         403.43
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.883(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9574(7)
_cell_length_b                   8.8817(7)
_cell_length_c                   10.7882(9)
_cell_measurement_reflns_used    10443
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.7530
_cell_measurement_theta_min      2.0580
_cell_volume                     953.98(13)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12291
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         2.763
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4067
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0496P)^2^+0.1878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.903
_reflns_Friedel_fraction_max     0.855
_reflns_number_gt                3901
_reflns_number_total             4067
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05807_si_005.cif
_cod_data_source_block           dat27
_cod_original_cell_volume        953.99(13)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4132723
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_checksum              76316
_shelx_hkl_checksum              52