Catalytic Enantioselective Synthesis of a Pyrrolizidine-Alkaloid-Inspired Compound Collection with Antiplasmodial Activity.
Jia, Zhi-Jun; Takayama, Hiroshi; Futamura, Yushi; Aono, Harumi; Bauer, Jonathan O.; Strohmann, Carsten; Antonchick, Andrey P.; Osada, Hiroyuki; Waldmann, Herbert; The Journal of organic chemistry 83 (2018) 7033–7041; doi:10.1021/acs.joc.7b03202

data_4033514
_publ_section_title
;
 Catalytic Enantioselective Synthesis of a Pyrrolizidine-Alkaloid-Inspired
 Compound Collection with Antiplasmodial Activity.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7033
_journal_page_last               7041
_journal_paper_doi               10.1021/acs.joc.7b03202
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H21 Br N2 O6'
_chemical_formula_sum            'C19 H21 Br N2 O6'
_chemical_formula_weight         453.29
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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_date             2014-01-07T18:20:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.155(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2117(10)
_cell_length_b                   9.0778(7)
_cell_length_c                   10.8267(12)
_cell_measurement_reflns_used    3825
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.46
_cell_volume                     973.16(17)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)'
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_molecular_graphics
;
Ortep-3 (Farrugia, 1997) and Schakal 92
 (Keller 1992)
;
_computing_publication_material  'wingx (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur S Oxford Diffraction'
_diffrn_measurement_method       Omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_av_unetI/netI     0.158
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9550
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    2.151
_exptl_absorpt_correction_T_max  0.814
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd. Empirical absorption correction using
spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3825
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0454
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0075P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0532
_refine_ls_wR_factor_ref         0.0559
_reflns_number_gt                2069
_reflns_number_total             3825
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b03202_si_002.cif
_cod_data_source_block           2168
_cod_depositor_comments          'Adding full bibliography for 4033514.cif.'
_cod_original_cell_volume        973.16(16)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4033514