Mn(III)-Mediated Reactions of Cyclopropanols with Vinyl Azides: Synthesis of Pyridine and 2-Azabicyclo[3.3.1]non-2-en-1-ol Derivatives
Yi-Feng Wang; Shunsuke Chiba; Journal of the American Chemical Society 131 (2009) 12570–12572; doi:10.1021/ja905110c

data_4104992
_publ_contact_author
;
Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
;
_publ_contact_author_email       shunsuke@ntu.edu.sg
_publ_contact_author_fax         '+65 6791 1961'
_publ_contact_author_phone       '+65 6513 8013'
_publ_section_title
;
 Mn(III)-Mediated Reactions of Cyclopropanols with Vinyl Azides: Synthesis
 of Pyridine and 2-Azabicyclo[3.3.1]non-2-en-1-ol Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12570
_journal_page_last               12572
_journal_paper_doi               10.1021/ja905110c
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H19 N O'
_chemical_formula_sum            'C23 H19 N O'
_chemical_formula_weight         325.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             2008-12-16
_audit_creation_method           'by CrystalStructure 3.8.2'
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.346(4)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.858(2)
_cell_length_b                   12.9873(14)
_cell_length_c                   13.198(3)
_cell_measurement_reflns_used    335
_cell_measurement_temperature    80.1
_cell_measurement_theta_max      36.3
_cell_measurement_theta_min      1.6
_cell_volume                     1650.6(5)
_computing_cell_refinement       PROCESS
_computing_data_collection       PROCESS
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.774
_diffrn_measured_fraction_theta_max 0.774
_diffrn_measurement_device_type  'Rigaku RAXIS-SPIDER'
_diffrn_measurement_method       \w
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.122
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28622
_diffrn_reflns_theta_full        36.32
_diffrn_reflns_theta_max         36.32
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Rigaku MM-007HF'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       prism
_exptl_crystal_F_000             688.00
_exptl_crystal_size_max          1.00
_exptl_crystal_size_mid          1.00
_exptl_crystal_size_min          1.00
_refine_diff_density_max         1.23
_refine_diff_density_min         -1.49
_refine_ls_extinction_coef       337(12)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   8.582
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     294
_refine_ls_number_reflns         13306
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0.0508
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1.0'
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_ref         0.1059
_reflns_number_gt                13098
_reflns_number_total             6201
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja905110c_si_002.cif
_cod_data_source_block           '__Chiba-4an'
_cod_original_cell_volume        1650.6(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4104992