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_4029326
_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         'C26 H19 N O4'
_chemical_formula_sum            'C26 H19 N O4'
_chemical_formula_weight         409.42
_chemical_name_systematic
;
4,6,8-Triphenyl-5,7-dioxa-1-azabicyclo[4.4.1]undeca-3,8-diene-2,10-dione 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-12-29
_audit_creation_method
;
  Olex2 1.1-beta
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.8500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.5600(5)
_cell_length_b                   17.9642(6)
_cell_length_c                   17.1799(6)
_cell_measurement_reflns_used    4346
_cell_measurement_temperature    100
_cell_measurement_theta_max      56.608
_cell_measurement_theta_min      3.634
_cell_volume                     4322.7(3)
_computing_cell_refinement       'SAINT V7.60A (Bruker, 2003)'
_computing_data_collection       'Proteum2 V2011.2-0 (Bruker, 2001)'
_computing_data_reduction        'SAINT V7.60A (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
;
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      100.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker Platinum-135 area detector'
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Proteum R'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21195
_diffrn_reflns_theta_full        58.00
_diffrn_reflns_theta_max         60.57
_diffrn_reflns_theta_min         2.46
_diffrn_source                   'rotating anode'
_diffrn_source_target            Cu
_diffrn_source_type              'Bruker Microstar rotating anode'
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.0725 before and 0.0533 after correction.
The Ratio of minimum to maximum transmission is 0.8419.
The \l/2 correction factor is 0.0015.
;
_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    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         5904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1073
_reflns_number_gt                4157
_reflns_number_total             5904
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-74-S2.cif
_cod_data_source_block           3a_dax44
_cod_depositor_comments
'Adding full bibliography for 4029324--4029326.cif.'
_cod_database_code               4029326