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_4026748
_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
;
 (1S,2S,8aS)-2.bromooctahydro-1-indolizinol
;
_space_group_IT_number           161
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'R 3 -2"c'
_symmetry_space_group_name_H-M   'R 3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   21.7590(10)
_cell_length_b                   21.7590(10)
_cell_length_c                   10.3880(10)
_cell_measurement_reflns_used    1053
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      61.8373
_cell_measurement_theta_min      4.2524
_cell_volume                     4259.3(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_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      295(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega  -80.00  -55.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -        0.4688  179.0000  -30.0000 25

  2 omega  -86.00  -32.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -        0.4688  179.0000   60.0000 54

  3 omega -147.00  -87.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -77.8666 -144.0000  -64.0000 60

  4 omega   10.00   47.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       78.8041  -37.0000   90.0000 37

  5 omega   12.00   56.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       78.8041  -37.0000  -30.0000 44

  6 omega   69.00  145.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       78.8041   37.0000  -30.0000 76

;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       'omega scan'
_diffrn_orient_matrix_UB_11      0.0649306000
_diffrn_orient_matrix_UB_12      -0.0042065000
_diffrn_orient_matrix_UB_13      -0.0473726000
_diffrn_orient_matrix_UB_21      -0.0493463000
_diffrn_orient_matrix_UB_22      -0.0764743000
_diffrn_orient_matrix_UB_23      -0.0468532000
_diffrn_orient_matrix_UB_31      -0.0057636000
_diffrn_orient_matrix_UB_32      0.0284926000
_diffrn_orient_matrix_UB_33      -0.1324912000
_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  0.0745
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2466
_diffrn_reflns_theta_full        61.59
_diffrn_reflns_theta_max         61.8373
_diffrn_reflns_theta_min         4.2524
_diffrn_standards_decay_%        50
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    5.496
_exptl_absorpt_correction_T_max  0.6806
_exptl_absorpt_correction_T_min  0.5171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       needle
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         985
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0730P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                690
_reflns_number_total             985
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201830b_si_003.cif
_cod_data_source_block           exp_342
_cod_original_sg_symbol_Hall     R3-2"c
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               4026748