Development of the intramolecular Prins cyclization/Schmidt reaction for the construction of the azaspiro[4,4]nonane: application to the formal synthesis of (±)-stemonamine.
Chen, Zhi-Hua; Tu, Yong-Qiang; Zhang, Shu-Yu; Zhang, Fu-Min; Organic letters 13 (2011) 724–727; doi:10.1021/ol102955e

data_1501939
_publ_section_title
;
 Development of the intramolecular Prins cyclization/Schmidt reaction for
 the construction of the azaspiro[4,4]nonane: application to the formal
 synthesis of (+-)-stemonamine.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              724
_journal_page_last               727
_journal_paper_doi               10.1021/ol102955e
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C12 H17 N O2'
_chemical_formula_weight         207.27
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.527(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.200(3)
_cell_length_b                   11.695(6)
_cell_length_c                   15.337(7)
_cell_measurement_reflns_used    741
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.19
_cell_volume                     1111.7(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0869
_diffrn_reflns_av_sigmaI/netI    0.1072
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6334
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.2436
_refine_ls_R_factor_gt           0.1223
_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^)+(0.1583P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2702
_refine_ls_wR_factor_ref         0.3353
_reflns_number_gt                801
_reflns_number_total             1888
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol102955e_si_002.cif
_cod_data_source_block           p21n2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P2(1)/n
_cod_database_code               1501939