Diastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with chiral enamides.
Tchabanenko, Kirill; Sloan, Colleen; Bunetel, Yves-Mael; Mullen, Philip; Organic & biomolecular chemistry 10 (2012) 4215–4219; doi:10.1039/c2ob07007c

data_7152349
_publ_section_title
;
 Diastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with
 chiral enamides.
;
_journal_issue                   21
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4215
_journal_page_last               4219
_journal_paper_doi               10.1039/c2ob07007c
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H19 N O4'
_chemical_formula_sum            'C16 H18 N O3'
_chemical_formula_weight         272.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   7.3012(2)
_cell_length_b                   9.1671(2)
_cell_length_c                   21.9003(4)
_cell_measurement_temperature    120(2)
_cell_volume                     1465.81(6)
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12465
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             580
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.133
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.1(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.247
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.247
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0550
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1669
_reflns_number_gt                2960
_reflns_number_total             3337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob07007c.txt
_cod_data_source_block           2010SRC0803
_cod_database_code               7152349