Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems.
Khlebnikov, Alexander F.; Novikov, Mikhail S.; Pakalnis, Viktoriia V.; Iakovenko, Roman O.; Yufit, Dmitry S.; Beilstein journal of organic chemistry 10 (2014) 784–793; doi:10.3762/bjoc.10.74

data_4029324
_publ_section_title
;
 Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones:
 Competition between the formation of ortho-fused and bridged heterocyclic
 systems.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              784
_journal_page_last               793
_journal_paper_doi               10.3762/bjoc.10.74
_journal_volume                  10
_journal_year                    2014
_chemical_formula_moiety         'C23 H17 N O2'
_chemical_formula_sum            'C23 H17 N O2'
_chemical_formula_weight         339.38
_chemical_name_systematic
;
4,6,7-Triphenyl-5-oxa-1-azabicyclo[4.1.0]hept-3-en-2-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             2012-01-30
_audit_creation_method
;
  Olex2 1.1-beta
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.619(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   34.473(4)
_cell_length_b                   5.5047(4)
_cell_length_c                   17.7523(17)
_cell_measurement_reflns_used    502
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.3487
_cell_measurement_theta_min      2.8374
_cell_volume                     3299.7(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -94.00   -6.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867  -57.0000   30.0000 176

  2 omega -101.00  -75.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867 -179.0000  -60.0000 52

  3 omega  -96.00   10.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867  -19.0000  -90.0000 212

  4 omega   16.00   52.00   0.5000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       26.8117  -77.0000  -60.0000 72
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       \w-scan
_diffrn_orient_matrix_UB_11      0.0115139000
_diffrn_orient_matrix_UB_12      -0.0235746000
_diffrn_orient_matrix_UB_13      -0.0281309000
_diffrn_orient_matrix_UB_21      0.0174949000
_diffrn_orient_matrix_UB_22      0.0264994000
_diffrn_orient_matrix_UB_23      0.0273381000
_diffrn_orient_matrix_UB_31      0.0015592000
_diffrn_orient_matrix_UB_32      -0.1238894000
_diffrn_orient_matrix_UB_33      0.0111811000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_xray_symbol    Mo
_diffrn_reflns_av_R_equivalents  0.1241
_diffrn_reflns_av_unetI/netI     0.2128
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10670
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.8374
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_type              'sealed tube'
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.997
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.0699
_exptl_crystal_size_min          0.0199
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.902
_refine_ls_R_factor_all          0.1890
_refine_ls_R_factor_gt           0.0737
_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^)+(0.0100P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                1654
_reflns_number_total             3980
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-74-S4.cif
_cod_data_source_block           17_dax46
_cod_depositor_comments
'Adding full bibliography for 4029324--4029326.cif.'
_cod_database_code               4029324
_chemical_oxdiff_formula         'C23 H19 N1 O1'
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44