Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar Cycloadducts. Evaluation as Inhibitors of a β-Galactofuranosidase.
Oliveira Udry, Guillermo A.; Repetto, Evangelina; Vega, Daniel R.; Varela, Oscar; The Journal of organic chemistry 81 (2016) 4179–4189; doi:10.1021/acs.joc.6b00514

data_4031997
_publ_section_title
;
 Synthesis of Enantiomeric Polyhydroxyalkylpyrrolidines from 1,3-Dipolar
 Cycloadducts. Evaluation as Inhibitors of a \b-Galactofuranosidase.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4179
_journal_page_last               4189
_journal_paper_doi               10.1021/acs.joc.6b00514
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C28 H40 N2 O5'
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_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
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_cell_measurement_reflns_used    178
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;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
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_diffrn_ambient_temperature      293(2)
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_diffrn_measurement_details
;
  1 omega  -11.00   93.00   1.0000   11.0450
omega____ theta____ kappa____ phi______ frames
    -       21.0583   37.0000   60.0000 104

  2 omega  -24.00   40.00   1.0000   11.0450
omega____ theta____ kappa____ phi______ frames
    -       21.0583  -99.0000 -150.0000 64

  3 omega  -25.00   54.00   1.0000   11.0450
omega____ theta____ kappa____ phi______ frames
    -       21.0583  -99.0000  -90.0000 79

  4 omega  -25.00    0.00   1.0000   11.0450
omega____ theta____ kappa____ phi______ frames
    -      -21.4489  -99.0000    0.0000 25

;
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_diffrn_orient_matrix_UB_11      -0.0348418000
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_diffrn_orient_matrix_UB_13      0.0083656000
_diffrn_orient_matrix_UB_21      0.0208366000
_diffrn_orient_matrix_UB_22      -0.0089128000
_diffrn_orient_matrix_UB_23      0.0191190000
_diffrn_orient_matrix_UB_31      0.0246285000
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_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  '0.0291 using hklf4 instruction'
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.918
_diffrn_reflns_Laue_measured_fraction_max 0.797
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
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_diffrn_reflns_limit_l_min       -20
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_diffrn_reflns_point_group_measured_fraction_full 0.716
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_diffrn_reflns_theta_max         28.974
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_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
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_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
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 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -1.6(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         6429
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0526
_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^)+(0.0785P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1441
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_reflns_Friedel_fraction_full    0.461
_reflns_Friedel_fraction_max     0.363
_reflns_number_gt                3991
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_cod_data_source_file            jo6b00514_si_002.cif
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_cod_database_code               4031997
_shelx_shelxl_version_number     2014/7
_cell_oxdiff_length_a            14.99(2)
_cell_oxdiff_length_b            5.395(8)
_cell_oxdiff_length_c            33.41(3)
_cell_oxdiff_angle_alpha         90.07(9)
_cell_oxdiff_angle_beta          90.41(8)
_cell_oxdiff_angle_gamma         89.61(11)
_cell_oxdiff_volume              2702(6)
_cell_oxdiff_measurement_reflns_used 2566
_cell_oxdiff_twin_number         2
_shelx_res_checksum              84898
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