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_4515149
_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 unk
_chemical_formula_moiety         'C14 H24 N2 O3'
_chemical_formula_sum            'C14 H24 N2 O3'
_chemical_formula_weight         268.35
_chemical_name_common            40
_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_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.355(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8929(4)
_cell_length_b                   9.6349(6)
_cell_length_c                   13.2171(9)
_cell_measurement_reflns_used    4391
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.09
_cell_measurement_theta_min      5.69
_cell_volume                     747.16(9)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0559
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9664
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.384
_diffrn_reflns_theta_max         66.384
_diffrn_reflns_theta_min         5.691
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SadAbs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
; 
 Flack x determined using 880 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(16)
_refine_ls_extinction_coef       0.012(2)
_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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2594
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0361P)^2^+0.0511P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0828
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2233
_reflns_number_total             2594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao9b01509_si_002.cif
_cod_data_source_block           40
_cod_database_code               4515149
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              18646
_shelx_hkl_checksum              90072