Studies of intramolecular cyclizations of N-acyliminium ions derived from acyclic ketones: unanticipated stereochemical and structural results.
Chao, Wenchun; Waldman, Jacob H.; Weinreb, Steven M.; Organic letters 5 (2003) 2915–2918; doi:10.1021/ol035046m

data_1507352
_publ_section_title
;
 Studies of intramolecular cyclizations of N-acyliminium ions derived from
 acyclic ketones: unanticipated stereochemical and structural results.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              2915
_journal_page_last               2918
_journal_paper_doi               10.1021/ol035046m
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C16 H21 N O'
_chemical_formula_weight         243.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                82.979(3)
_cell_angle_beta                 84.235(3)
_cell_angle_gamma                88.777(3)
_cell_formula_units_Z            8
_cell_length_a                   10.1195(5)
_cell_length_b                   14.1443(7)
_cell_length_c                   19.3863(10)
_cell_measurement_temperature    293(2)
_cell_volume                     2740.0(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11795
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.073
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     972
_refine_ls_number_reflns         7132
_refine_ls_number_restraints     3015
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0526
_refine_ls_shift/su_max          1.578
_refine_ls_shift/su_mean         0.025
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0477P)^2^+1.5697P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                5856
_reflns_number_total             7132
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol035046msi20030610_034855.cif
_cod_data_source_block           cfc1
_cod_database_code               1507352