Stable d-xylose ditriflate in divergent syntheses of dihydroxy prolines, pyrrolidines, tetrahydrofuran-2-carboxylic acids, and cyclic β-amino acids
Balo, Rosalino; Fernández, Alberto G.; Chopdat, Adam; Ayadi, Soufian El; Kato, Atsushi; Estévez, Ramón J.; Fleet, George W. J.; Estévez, Juan C.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01255C

data_7159013
_publ_section_title
;
 Stable d-xylose ditriflate in divergent syntheses of dihydroxy prolines,
 pyrrolidines, tetrahydrofuran-2-carboxylic acids, and cyclic \b-amino
 acids
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01255C
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H21 N O5'
_chemical_formula_sum            'C18 H21 N O5'
_chemical_formula_weight         331.36
_chemical_name_common            45.10F2
_chemical_name_systematic        45.10F2
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-02-23T13:08:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2022-06-21 deposited with the CCDC.	2022-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.811(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8300(5)
_cell_length_b                   16.7011(12)
_cell_length_c                   8.4430(6)
_cell_measurement_reflns_used    2823
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.38
_cell_measurement_theta_min      2.44
_cell_measurement_wavelength     0.71073
_cell_volume                     821.99(11)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      0.071634
_diffrn_orient_matrix_UB_12      0.030459
_diffrn_orient_matrix_UB_13      -0.088473
_diffrn_orient_matrix_UB_21      -0.017942
_diffrn_orient_matrix_UB_22      0.050895
_diffrn_orient_matrix_UB_23      0.060974
_diffrn_orient_matrix_UB_31      0.154834
_diffrn_orient_matrix_UB_32      -0.008194
_diffrn_orient_matrix_UB_33      0.049856
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11801
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.191
_diffrn_reflns_theta_min         2.413
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2, AcOEt'
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 982 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3577
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0363P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                2628
_reflns_number_total             3577
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01255c2.cif
_cod_data_source_block           2015RE001ROB01
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159013
_shelx_estimated_absorpt_t_min   0.96
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              3804