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_4026747
_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_formula_moiety         'C8 H14 Br N O'
_chemical_formula_sum            'C8 H14 Br N O'
_chemical_formula_weight         220.11
_chemical_name_systematic
;
 (1SR,2SR,8aSR)-2.bromooctahydro-1-indolizinol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.495(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7350(10)
_cell_length_b                   6.6050(10)
_cell_length_c                   17.8320(10)
_cell_measurement_reflns_used    2783
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      70.5621
_cell_measurement_theta_min      4.9541
_cell_volume                     910.17(19)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
;
_computing_molecular_graphics    Ortep3
_computing_publication_material  Ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
  1 omega  -76.00  -32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -5.5021  179.0000    0.0000 44

  2 omega  -26.00   31.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        5.5021   91.0000  -34.0000 57

  3 omega   34.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        5.5021  179.0000  -60.0000 39

  4 omega   62.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        5.5021  179.0000 -150.0000 31

  5 omega -104.00  -75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -45.0000   30.0000 29

  6 omega   77.00  166.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       97.3169   45.0000  -30.0000 89

  7 omega   20.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       97.3169  -15.0000  150.0000 98

  8 omega   40.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       97.3169  -45.0000  -60.0000 75

  9 omega   54.00  128.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       97.3169  -77.0000  -90.0000 74

 10 omega  -76.00   17.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -5.5021  -37.0000  120.0000 93

 11 omega  -28.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -5.5021   37.0000  -90.0000 93

 12 omega   67.00  163.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       97.3169   77.0000 -120.0000 96

;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'omega scan'
_diffrn_orient_matrix_UB_11      0.1910680140
_diffrn_orient_matrix_UB_12      0.0664475024
_diffrn_orient_matrix_UB_13      0.0023331864
_diffrn_orient_matrix_UB_21      -0.0261511070
_diffrn_orient_matrix_UB_22      0.0921271110
_diffrn_orient_matrix_UB_23      -0.0790485565
_diffrn_orient_matrix_UB_31      -0.0506465432
_diffrn_orient_matrix_UB_32      0.2037668731
_diffrn_orient_matrix_UB_33      0.0350040115
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3844
_diffrn_reflns_theta_full        70.67
_diffrn_reflns_theta_max         70.67
_diffrn_reflns_theta_min         4.96
_diffrn_standards_decay_%        50
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.716
_exptl_absorpt_correction_T_max  0.7097
_exptl_absorpt_correction_T_min  0.5332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.194
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0788
_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^)+(0.1020P)^2^+5.2897P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2170
_refine_ls_wR_factor_ref         0.2224
_reflns_number_gt                1462
_reflns_number_total             1674
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201830b_si_002.cif
_cod_data_source_block           exp_310
_cod_original_sg_symbol_Hall     -P2yn
_cod_database_code               4026747