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_4132725
_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 ad
_chemical_formula_moiety         'C17 H22 F N O5'
_chemical_formula_sum            'C17 H22 F N O5'
_chemical_formula_weight         339.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.61245(5)
_cell_length_b                   10.21862(6)
_cell_length_c                   18.99958(12)
_cell_measurement_reflns_used    24505
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.2210
_cell_measurement_theta_min      4.2960
_cell_volume                     1672.103(17)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0072
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29237
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.213
_diffrn_reflns_theta_min         4.914
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1251 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       0.0061(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0237
_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^)+(0.0210P)^2^+0.4851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0573
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                2973
_reflns_number_total             2974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b05807_si_003.cif
_cod_data_source_block           at2
_cod_original_cell_volume        1672.102(17)
_cod_database_code               4132725
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.728
_shelx_estimated_absorpt_t_max   0.957
_shelx_res_checksum              29523
_shelx_hkl_checksum              85081