Synthesis of 1,2-Dihydroxyindolizidines from 1-(2-Pyridyl)-2-propen-1-ol
Donatella Giomi; Renzo Alfini; Alessandra Micoli; Elisa Calamai; Cristina Faggi; Alberto Brandi; Journal of Organic Chemistry 76 (2011) 9536–9541; doi:10.1021/jo201830b

data_4026746
_publ_contact_author_address
;Universit\`a Firenze
Dipartimento Chimica "U.Schiff"
Via della Lastruccia 3
50019 Sesto Fiorentino
Firenze
Italy
;
_publ_contact_author_email       cristina.faggi@unifi.it
_publ_contact_author_name        'Dr. Cristina Faggi'
_publ_section_title
;
 Synthesis of 1,2-Dihydroxyindolizidines from 1-(2-Pyridyl)-2-propen-1-ol
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9536
_journal_page_last               9541
_journal_paper_doi               10.1021/jo201830b
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         '(C8 H12 Br N O)3'
_chemical_formula_sum            'C8 H12 Br N O'
_chemical_formula_weight         218.10
_chemical_name_systematic
(1S,2S,8aS)-2-bromo-1,2,3,5,8,8a-hexahydro-1-indolizinol
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
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_audit_creation_method
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CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
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_cell_length_a                   10.3126(2)
_cell_length_b                   13.3307(3)
_cell_length_c                   20.6168(5)
_cell_measurement_reflns_used    2409
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      61.8468
_cell_measurement_theta_min      3.9461
_cell_volume                     2834.28(11)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
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CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
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CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_molecular_graphics    Ortep3
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_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details
;
  1 omega  -40.00   31.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -        0.1562  -86.0000  218.0000    0.0000    0.0000 71

  2 omega   30.00   71.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -        0.1562   36.0000  172.0000    0.0000    0.0000 41

  3 omega  -59.00   -6.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -77.8666   77.0000  330.0000    0.0000    0.0000 53

  4 omega   60.00   99.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       78.1791  -45.0000  150.0000    0.0000    0.0000 39

  5 omega  121.00  147.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       78.1791   45.0000  240.0000    0.0000    0.0000 26

  6 omega  110.00  150.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       78.1791  130.0000  223.0000    0.0000    0.0000 40

  7 omega   77.00  117.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       78.1791   86.0000  141.0000    0.0000    0.0000 40

  8 omega   10.00   58.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       78.1791  -77.0000  120.0000    0.0000    0.0000 48

;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'omega scan'
_diffrn_orient_matrix_UB_11      0.0046892441
_diffrn_orient_matrix_UB_12      0.0147493441
_diffrn_orient_matrix_UB_13      -0.0740803613
_diffrn_orient_matrix_UB_21      0.0683083155
_diffrn_orient_matrix_UB_22      0.1017744147
_diffrn_orient_matrix_UB_23      0.0095979274
_diffrn_orient_matrix_UB_31      0.1327766017
_diffrn_orient_matrix_UB_32      -0.0528784182
_diffrn_orient_matrix_UB_33      -0.0022284741
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0645
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6433
_diffrn_reflns_theta_full        62.06
_diffrn_reflns_theta_max         62.06
_diffrn_reflns_theta_min         3.95
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        50
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.505
_exptl_absorpt_correction_T_max  0.7187
_exptl_absorpt_correction_T_min  0.5767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       'sharp needle'
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.942
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0625P)^2^+1.0976P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1211
_reflns_number_gt                2196
_reflns_number_total             3523
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201830b_si_001.cif
_cod_data_source_block           exp_115
_cod_original_cell_volume        2834.5(4)
_cod_database_code               4026746