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_4029325
_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         'C36 H30 N2 O6'
_chemical_formula_sum            'C36 H30 N2 O6'
_chemical_formula_weight         586.62
_chemical_name_systematic
;
(6aRS,12aRS)-6a,12a-Bis(4-methoxyphenyl)-2,8-diphenyl-6,6a,12,12a-tetrahydrobis-
[1,3]oxazino[3,2-a:3',2'-d]pyrazine-4,10-dione 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-07-23
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;
  Olex2 1.2-beta
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.738(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1236(5)
_cell_length_b                   18.2526(7)
_cell_length_c                   13.4793(5)
_cell_measurement_reflns_used    2656
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.5386
_cell_measurement_theta_min      2.5810
_cell_volume                     2897.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.8 (release 13-04-2012 CrysAlis171 .NET)
(compiled Apr 13 2012,18:42:44)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.8 (release 13-04-2012 CrysAlis171 .NET)
(compiled Apr 13 2012,18:42:44)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.8 (release 13-04-2012 CrysAlis171 .NET)
(compiled Apr 13 2012,18:42:44)
;
_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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      120
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -70.00   33.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867   19.0000   30.0000 103

  2 omega  -48.00  -17.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867   57.0000  150.0000 31

  3 omega    7.00   66.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -100.0000  120.0000 59

  4 omega   34.00   92.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -137.0000  -14.0000 58

  5 omega  -12.00   20.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679    0.0000    0.0000 32

  6 omega  -95.00  -70.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867  -57.0000    0.0000 25
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       \w-scan
_diffrn_orient_matrix_UB_11      0.0173530000
_diffrn_orient_matrix_UB_12      0.0372122000
_diffrn_orient_matrix_UB_13      0.0025562000
_diffrn_orient_matrix_UB_21      0.0575716000
_diffrn_orient_matrix_UB_22      -0.0112452000
_diffrn_orient_matrix_UB_23      0.0097824000
_diffrn_orient_matrix_UB_31      -0.0031325000
_diffrn_orient_matrix_UB_32      -0.0002888000
_diffrn_orient_matrix_UB_33      -0.0532126000
_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  0.0596
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16575
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.72
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.8 (release 13-04-2012 CrysAlis171 .NET)
(compiled Apr 13 2012,18:42:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.2065
_exptl_crystal_size_min          0.0757
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         6654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0567
_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^)+(0.0390P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1284
_reflns_number_gt                4337
_reflns_number_total             6654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-74-S3.cif
_cod_data_source_block           4b_dax56
_cod_depositor_comments
'Adding full bibliography for 4029324--4029326.cif.'
_cod_original_cell_volume        2897.46(19)
_cod_database_code               4029325
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44