Organocatalytic asymmetric aza-Nazarov cyclization of an azirine.
Shimada, Naoyuki; Ashburn, Bradley O.; Basak, Ashok K.; Bow, William F.; Vicic, David A.; Tius, Marcus A.; Chemical communications (Cambridge, England) 46 (2010) 3774–3775; doi:10.1039/b927564a

data_7105576
_publ_section_title
;
 Organocatalytic asymmetric aza-Nazarov cyclization of an azirine.
;
_journal_issue                   21
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3774
_journal_page_last               3775
_journal_paper_doi               10.1039/b927564a
_journal_volume                  46
_journal_year                    2010
_chemical_absolute_configuration rm
_chemical_formula_sum            'C27 H33 N O7'
_chemical_formula_weight         483.54
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 95.46(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.998(15)
_cell_length_b                   6.500(7)
_cell_length_c                   16.73(2)
_cell_measurement_reflns_used    1551
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.921
_cell_measurement_theta_min      1.705
_cell_volume                     1299(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1821
_diffrn_reflns_av_sigmaI/netI    0.3767
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17444
_diffrn_reflns_theta_full        32.72
_diffrn_reflns_theta_max         32.72
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_correction_T_min  0.9653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Rigaku
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   8(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         8691
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.3463
_refine_ls_R_factor_gt           0.0997
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1023P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2014
_refine_ls_wR_factor_ref         0.3209
_reflns_number_gt                2248
_reflns_number_total             8691
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b927564a.txt
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7105576