A simple approach to pyrrolylimidazole derivatives by azirine ring expansion with imidazolium ylides.
Khlebnikov, Alexander F.; Tomashenko, Olesya A.; Funt, Liya D.; Novikov, Mikhail S.; Organic & biomolecular chemistry 12 (2014) 6598–6609; doi:10.1039/c4ob00865k

data_7153910
_publ_section_title
;
 A simple approach to pyrrolylimidazole derivatives by azirine ring
 expansion with imidazolium ylides.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6598
_journal_page_last               6609
_journal_paper_doi               10.1039/c4ob00865k
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         '2(Br), 2(C20 H17 N4 O2), C H2 Cl2'
_chemical_formula_sum            'C41 H36 Br2 Cl2 N8 O4'
_chemical_formula_weight         935.50
_chemical_name_systematic
;
 ? 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-03-20
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 119.245(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.6382(7)
_cell_length_b                   10.7068(3)
_cell_length_c                   21.8503(9)
_cell_measurement_reflns_used    4367
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.8505
_cell_measurement_theta_min      2.6622
_cell_volume                     4008.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9988
_diffrn_measurement_details
;
  1 omega  -35.00   44.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223   57.0000  -30.0000 79

  2 omega  -81.00  -42.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  124.0000   82.0000 39

  3 omega  -93.00  -17.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223  -57.0000 -180.0000 76

  4 omega   13.00   76.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   57.0000   60.0000 63

  5 omega  -67.00  -17.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.4223   19.0000  -90.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0166601000
_diffrn_orient_matrix_UB_12      0.0447740000
_diffrn_orient_matrix_UB_13      -0.0273727000
_diffrn_orient_matrix_UB_21      -0.0161961000
_diffrn_orient_matrix_UB_22      -0.0488201000
_diffrn_orient_matrix_UB_23      -0.0249698000
_diffrn_orient_matrix_UB_31      -0.0342545000
_diffrn_orient_matrix_UB_32      0.0013476000
_diffrn_orient_matrix_UB_33      0.0031918000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11961
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.67
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1896
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0297P)^2^+5.9334P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                3828
_reflns_number_total             4613
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00865k2.cif
_cod_data_source_block           toa_077
_cod_depositor_comments
'Adding full bibliography for 7153910--7153912.cif.'
_cod_original_cell_volume        4008.7(2)
_cod_database_code               7153910
_chemical_oxdiff_formula         'C20 H17 Br N4 O2'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51