Iminium ion cascade reaction in the total synthesis of (+)-vincadifformine.
Pandey, Ganesh; C, Prasanna Kumara; Organic letters 13 (2011) 4672–4675; doi:10.1021/ol201892j

data_1502430
_publ_section_title
;
 Iminium ion cascade reaction in the total synthesis of
 (+)-vincadifformine.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4672
_journal_page_last               4675
_journal_paper_doi               10.1021/ol201892j
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C14 H18 N2 O2'
_chemical_formula_sum            'C14 H18 N2 O2'
_chemical_formula_weight         246.30
_chemical_melting_point          379.1(5)
_chemical_name_common            Oxaazapine
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.0581(5)
_cell_length_b                   11.0581(5)
_cell_length_c                   20.481(4)
_cell_measurement_reflns_used    7116
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.735
_cell_measurement_theta_min      2.708
_cell_volume                     2504.4(5)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    'SHELXTL, PyMOL and PLATON'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'Omega Scan'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17820
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2210
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0485P)^2^+0.2381P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0841
_reflns_number_gt                2071
_reflns_number_total             2210
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201892j_si_001.cif
_cod_data_source_block           birchpa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '105.5-106.5 degree centigrade' was
changed to '379.1(5)' - it was converted from degrees Celsius(C) to
Kelvins(K), the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Tetragonal' changed to
'tetragonal' 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_cell_volume        2504.5(5)
_cod_original_sg_symbol_H-M      'P43 21 2'
_cod_database_code               1502430