Radical Functionalization of Unsaturated Amino Acids: Synthesis of Side-Chain-Fluorinated, Azido-Substituted, and Hydroxylated Amino Acids.
Reeve, Philip A. P.; Grabowska, Urszula; Oden, Lourdes Salvador; Wiktelius, Daniel; Wångsell, Fredrik; Jackson, Richard F. W.; ACS omega 4 (2019) 10854–10865; doi:10.1021/acsomega.9b01509

data_4515148
_publ_section_title
;
 Radical Functionalization of Unsaturated Amino Acids: Synthesis of
 Side-Chain-Fluorinated, Azido-Substituted, and Hydroxylated Amino Acids.
;
_journal_issue                   6
_journal_name_full               'ACS omega'
_journal_page_first              10854
_journal_page_last               10865
_journal_paper_doi               10.1021/acsomega.9b01509
_journal_volume                  4
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H24 F3 N O4'
_chemical_formula_sum            'C15 H24 F3 N O4'
_chemical_formula_weight         339.35
_chemical_name_common            24
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.20190(10)
_cell_length_b                   11.2334(3)
_cell_length_c                   28.6154(6)
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.58
_cell_measurement_theta_min      3.09
_cell_volume                     1672.14(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            20183
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         66.605
_diffrn_reflns_theta_min         3.089
_exptl_absorpt_coefficient_mu    1.016
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 1154 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2951
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0260
_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^)+(0.0397P)^2^+0.2352P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0656
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2863
_reflns_number_total             2951
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao9b01509_si_002.cif
_cod_data_source_block           24
_cod_database_code               4515148
_shelx_estimated_absorpt_t_min   0.687
_shelx_estimated_absorpt_t_max   0.905
_shelxl_version_number           2014/6
_shelx_res_checksum              36309
_shelx_hkl_checksum              78008