Synthesis and Fucosidase Inhibitory Study of Unnatural Pyrrolidine Alkaloid 4-epi-(+)-Codonopsinine
Alexis Kotland; Fabien Accadbled; Koen Robeyns; Jean-Bernard Behr; Journal of Organic Chemistry 76 (2011) 4094–4098; doi:10.1021/jo200176u

data_4026291
_publ_section_title
;
 Synthesis and Fucosidase Inhibitory Study of Unnatural Pyrrolidine
 Alkaloid 4-epi-(+)-Codonopsinine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4094
_journal_page_last               4098
_journal_paper_doi               10.1021/jo200176u
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C13 H19 N O3'
_chemical_formula_sum            'C13 H19 N O3'
_chemical_formula_weight         237.29
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.924(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.8438(3)
_cell_length_b                   6.9463(3)
_cell_length_c                   12.6905(7)
_cell_measurement_reflns_used    11166
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.7134
_cell_measurement_theta_min      2.9266
_cell_volume                     602.51(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    PLATON
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '200 images, \D\F 3\%'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_radiation_source         'RU200 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1538
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14054
_diffrn_reflns_theta_full        25.77
_diffrn_reflns_theta_max         25.77
_diffrn_reflns_theta_min         2.98
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            translucent
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.188
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.231
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2305
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.231
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.1482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                2296
_reflns_number_total             2305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200176u_si_001.cif
_cod_data_source_block           jbk73
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4026291