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_4026741
_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         'C30 H25 N O3'
_chemical_formula_sum            'C30 H25 N O3'
_chemical_formula_weight         447.51
_chemical_name_systematic
;
(2RS,3SR)-2-Methoxy-2,3,6,7-tetraphenyl-3,4-dihydro-1,4-oxazepin-5(2H)-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2010-12-16
_audit_creation_method
;
  Olex2 1.1-beta
  (compiled 2010.10.26 svn.r1482, GUI svn.r3310)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 117.263(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.4292(6)
_cell_length_b                   10.2810(3)
_cell_length_c                   21.1739(5)
_cell_measurement_reflns_used    5682
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.98
_cell_measurement_theta_min      2.16
_cell_volume                     4727.2(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0233
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            26620
_diffrn_reflns_theta_full        29.50
_diffrn_reflns_theta_max         29.50
_diffrn_reflns_theta_min         1.88
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2006/1 (Bruker,2006) was used for absorption correction.
 R(int) was 0.0933 before and 0.0211 after correction.
 The Ratio of minimum to maximum transmission is 0.5936.
 The \l/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       block
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.38
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0700P)^2^+2.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1217
_reflns_number_gt                5481
_reflns_number_total             6588
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201563b_si_006.cif
_cod_data_source_block           '_41_dax21'
_cod_original_cell_volume        4727.2(3)
_cod_database_code               4026741