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_7153912
_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         'C20 H16 N4 O2'
_chemical_formula_sum            'C20 H16 N4 O2'
_chemical_formula_weight         344.37
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.162(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4914(4)
_cell_length_b                   11.8011(3)
_cell_length_c                   13.0430(6)
_cell_measurement_reflns_used    5541
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.5772
_cell_measurement_theta_min      2.6968
_cell_volume                     1690.02(12)
_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
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9597
_diffrn_measured_fraction_theta_max 0.9597
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0542389000
_diffrn_orient_matrix_UB_12      -0.0197775000
_diffrn_orient_matrix_UB_13      -0.0094042000
_diffrn_orient_matrix_UB_21      -0.0275236000
_diffrn_orient_matrix_UB_22      0.0056666000
_diffrn_orient_matrix_UB_23      -0.0560887000
_diffrn_orient_matrix_UB_31      0.0218171000
_diffrn_orient_matrix_UB_32      0.0564512000
_diffrn_orient_matrix_UB_33      0.0023565000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7769
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.70
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85599
_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            'translucent colorless'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0173P)^2^+2.9620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                2331
_reflns_number_total             2827
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob00865k2.cif
_cod_data_source_block           ole1
_cod_depositor_comments
'Adding full bibliography for 7153910--7153912.cif.'
_cod_original_cell_volume        1690.02(11)
_cod_database_code               7153912
_reflns_odcompleteness_completeness 92.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C12(H12), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C23(H23), C24(H24), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;