Asymmetric synthesis of polyhydroxylated pyrrolizidines via transannular iodoamination with concomitant N-debenzylation.
Brock, E. Anne; Davies, Stephen G.; Lee, James A.; Roberts, Paul M.; Thomson, James E.; Organic letters 13 (2011) 1594–1597; doi:10.1021/ol103090z

data_1501963
_publ_section_title
;
 Asymmetric synthesis of polyhydroxylated pyrrolizidines via transannular
 iodoamination with concomitant N-debenzylation.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1594
_journal_page_last               1597
_journal_paper_doi               10.1021/ol103090z
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H35 I2 N1 O5'
_chemical_formula_sum            'C24 H35 I2 N O5'
_chemical_formula_weight         671.35
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                96.9997(19)
_cell_angle_beta                 101.3959(18)
_cell_angle_gamma                96.5153(14)
_cell_formula_units_Z            1
_cell_length_a                   8.3429(2)
_cell_length_b                   8.7613(3)
_cell_length_c                   9.7629(3)
_cell_measurement_reflns_used    2745
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     687.36(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5243
_diffrn_reflns_theta_full        26.678
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         5.215
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.319
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.32
_refine_diff_density_min         -0.78
_refine_ls_abs_structure_details 'Flack (1983), 2128 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.052(18)
_refine_ls_extinction_method     None
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5242
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0242
_refine_ls_shift/su_max          0.000105
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.01P)^2^ + 0.64P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0558
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_refine_ls_wR_factor_ref         0.0558
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              9
_reflns_limit_k_min              -11
_reflns_limit_l_max              12
_reflns_limit_l_min              -12
_reflns_number_gt                5061
_reflns_number_total             5243
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.11
_oxford_diffrn_Wilson_scale      2.54
_oxford_refine_ls_r_factor_ref   0.0255
_oxford_refine_ls_scale          0.6228(6)
_oxford_reflns_number_all        5242
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            ol103090z_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 1 '
_cod_original_formula_sum        'C24 H35 I2 N1 O5'
_cod_database_code               1501963