Synthesis of ω-Oxo Amino Acids and trans-5-Substituted Proline Derivatives Using Cross-Metathesis of Unsaturated Amino Acids.
Salih, Nabaz; Adams, Harry; Jackson, Richard F. W.; The Journal of organic chemistry 81 (2016) 8386–8393; doi:10.1021/acs.joc.6b01571

data_4037129
_publ_section_title
;
 Synthesis of \w-Oxo Amino Acids and trans-5-Substituted Proline
 Derivatives Using Cross-Metathesis of Unsaturated Amino Acids.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8386
_journal_page_last               8393
_journal_paper_doi               10.1021/acs.joc.6b01571
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C9 H16 N O3, C2 F3 O2'
_chemical_formula_sum            'C11 H16 F3 N O5'
_chemical_formula_weight         299.25
_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   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 93.139(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.9295(10)
_cell_length_b                   14.3156(15)
_cell_length_c                   21.898(2)
_cell_measurement_reflns_used    3004
_cell_measurement_temperature    97(2)
_cell_measurement_theta_max      19.02
_cell_measurement_theta_min      2.34
_cell_volume                     2795.0(5)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      97(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_unetI/netI     0.1121
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31198
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         0.931
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details
; 
 Flack x determined using 2207 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     729
_refine_ls_number_reflns         9761
_refine_ls_number_restraints     181
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1451
_refine_ls_R_factor_gt           0.0924
_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^)+(0.1021P)^2^+6.1453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2193
_refine_ls_wR_factor_ref         0.2483
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                6233
_reflns_number_total             9761
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01571_si_002.cif
_cod_data_source_block           23
_cod_original_cell_volume        2795.1(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037129
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2013-4
_shelx_res_checksum              20698
_shelx_hkl_checksum              36982