A novel strategy for the synthesis of 3-(N-heteryl)pyrrole derivatives.
Khlebnikov, Alexander F.; Golovkina, Maria V.; Novikov, Mikhail S.; Yufit, Dmitry S.; Organic letters 14 (2012) 3768–3771; doi:10.1021/ol3016594

data_1508314
_publ_section_title
;
 A novel strategy for the synthesis of 3-(N-heteryl)pyrrole derivatives.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3768
_journal_page_last               3771
_journal_paper_doi               10.1021/ol3016594
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C22 H18 N2, 0.5(O), 0.25(C2 O2), Br'
_chemical_formula_sum            'C22.5 H18 Br N2 O'
_chemical_formula_weight         412.30
_chemical_melting_point          'g.t. 260 C'
_chemical_name_systematic
;
1-(2,4-Diphenyl-1H-pyrrol-3-yl)-2-methylpyridinium bromide 
;
_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             2011-12-16
_audit_creation_method
;
  Olex2 1.1-beta
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.345(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.2498(8)
_cell_length_b                   8.5555(3)
_cell_length_c                   19.2815(6)
_cell_measurement_reflns_used    6888
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.074
_cell_measurement_theta_min      2.268
_cell_volume                     3879.6(3)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (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      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 6000 area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27614
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.73
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           5.0
_diffrn_source_power             0.1
_diffrn_source_target            Mo
_diffrn_source_voltage           20.0
_exptl_absorpt_coefficient_mu    2.133
_exptl_absorpt_correction_T_max  0.6610
_exptl_absorpt_correction_T_min  0.3481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2006/1 (Bruker,2006) was used for absorption correction.
R(int) was 0.0449 before and 0.0215 after correction.
The Ratio of minimum to maximum transmission is 0.5266.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dull light yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         2.160
_refine_diff_density_min         -2.269
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         5158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0835
_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^)+(0.0000P)^2^+45.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.1619
_reflns_number_gt                4144
_reflns_number_total             5158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3016594_si_001.cif
_cod_data_source_block           5f_dax39
_cod_depositor_comments
'Adding full bibliography for 1508313--1508316.cif.'
_cod_original_cell_volume        3879.6(2)
_cod_original_formula_sum        'C22.50 H18 Br N2 O'
_cod_database_code               1508314