Nonconcerted Cycloaddition of 2H-Azirines to Acylketenes: A Route to N-Bridgehead Heterocycles
Alexander F. Khlebnikov; Mikhail S. Novikov; Viktoriia V. Pakalnis; Dmitry S. Yufit; Journal of Organic Chemistry 76 (2011) 9344–9352; doi:10.1021/jo201563b

data_4026740
_publ_contact_author_address
;
Department of Chemistry
Durham University
South Rd.
Durham
DH1 3LE
UK
;
_publ_contact_author_email       d.s.yufit@durham.ac.uk
_publ_contact_author_name        'Dmitry Yufit'
_publ_section_title
;
 Nonconcerted Cycloaddition of 2H-Azirines to Acylketenes: A Route to
 N-Bridgehead Heterocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9344
_journal_page_last               9352
_journal_paper_doi               10.1021/jo201563b
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C39 H31 N O5, C2 H6 O'
_chemical_formula_sum            'C41 H37 N O6'
_chemical_formula_weight         639.72
_chemical_name_systematic
;
(Z)-Methyl 3-(5-oxo-2,6,7-triphenyl-2,3,4,5-tetrahydro-1,4-oxazepin-2-yloxy)-
2,3-diphenylacrylate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-11-24
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;
  Olex2 1.1-beta
  (compiled 2010.10.26 svn.r1482, GUI svn.r3310)
;
_cell_angle_alpha                96.969(10)
_cell_angle_beta                 104.944(10)
_cell_angle_gamma                106.416(10)
_cell_formula_units_Z            2
_cell_length_a                   10.1297(3)
_cell_length_b                   12.8314(4)
_cell_length_c                   14.6074(4)
_cell_measurement_reflns_used    5207
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      29.695
_cell_measurement_theta_min      2.202
_cell_volume                     1720.58(19)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_limit_h_max       14
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_diffrn_reflns_limit_l_min       -20
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_diffrn_reflns_theta_max         29.50
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_diffrn_source_power             0.1
_diffrn_source_target            Mo
_diffrn_source_voltage           20.0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            less
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   whitish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       blob
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         9595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.921
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0441
_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^)+(0.0400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                5796
_reflns_number_total             9595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201563b_si_005.cif
_cod_data_source_block           40a_dax19
_cod_original_cell_volume        1720.58(12)
_cod_database_code               4026740