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_7153911
_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_sum            'C28 H24 Br N4'
_chemical_formula_weight         496.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
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_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
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_cell_angle_beta                 79.244(2)
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_cell_formula_units_Z            2
_cell_length_a                   9.1221(2)
_cell_length_b                   10.9612(3)
_cell_length_c                   12.8679(3)
_cell_measurement_reflns_used    15533
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.5020
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_cell_volume                     1199.69(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
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_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22772
_diffrn_reflns_theta_full        70.99
_diffrn_reflns_theta_max         70.99
_diffrn_reflns_theta_min         3.68
_exptl_absorpt_coefficient_mu    2.505
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46988
_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_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.18
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_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.823
_refine_diff_density_min         -1.022
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+4.6368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1449
_reflns_number_gt                4507
_reflns_number_total             4636
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00865k2.cif
_cod_data_source_block           funt2
_cod_depositor_comments
'Adding full bibliography for 7153910--7153912.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7153911