Enantioselective synthesis of α-perfluoroalkylated prolines, their 6,7-membered homologues and derivatives.
Voznesenskaia, Natalia G.; Shmatova, Olga I.; Khrustalev, Victor N.; Nenajdenko, Valentine G.; Organic & biomolecular chemistry 16 (2018) 7004–7011; doi:10.1039/c8ob01223g

data_7156418
_publ_section_title
;
 Enantioselective synthesis of \a-perfluoroalkylated prolines, their
 6,7-membered homologues and derivatives.
;
_journal_issue                   38
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7004
_journal_page_last               7011
_journal_paper_doi               10.1039/c8ob01223g
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C6 H10 F3 N2 O, C4 H5 O6, H2 O'
_chemical_formula_sum            'C10 H17 F3 N2 O8'
_chemical_formula_weight         350.26
_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   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-12-12 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.74(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7271(19)
_cell_length_b                   7.2173(14)
_cell_length_c                   11.150(2)
_cell_measurement_reflns_used    600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.0
_cell_measurement_theta_min      3.2
_cell_volume                     727.1(3)
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_collection       'Marccd (Doyle, 2011)'
_computing_data_reduction        iMosflm
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       '/f scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.96990
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_av_unetI/netI     0.1622
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7283
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        35.587
_diffrn_reflns_theta_max         38.403
_diffrn_reflns_theta_min         3.077
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scala (Evans, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_description       needle
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 664 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(6)
_refine_ls_extinction_coef       0.020(3)
_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   0.910
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2880
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.909
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0562
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1365
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.860
_reflns_number_gt                2071
_reflns_number_total             2880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01223g2.cif
_cod_data_source_block           417b
_cod_depositor_comments          'Adding full bibliography for 7156418.cif.'
_cod_database_code               7156418
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.892
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              78522