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_1508315
_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         'Br, H2 O, C27 H21 N2'
_chemical_formula_sum            'C27 H23 Br N2 O'
_chemical_formula_weight         471.38
_chemical_melting_point          'g.t. 260 C'
_chemical_name_systematic
;
1-(2,4,5-Triphenyl-1H-pyrrol-3-yl)pyridinium bromide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-11-17
_audit_creation_method
;
  Olex2 1.1-beta
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                85.831(2)
_cell_angle_beta                 70.146(2)
_cell_angle_gamma                67.185(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5612(4)
_cell_length_b                   10.7890(5)
_cell_length_c                   12.4446(5)
_cell_measurement_reflns_used    2989
_cell_measurement_temperature    100
_cell_measurement_theta_max      58.787
_cell_measurement_theta_min      3.785
_cell_volume                     1110.38(9)
_computing_cell_refinement       'SAINT V7.60A (Bruker, 2003)'
_computing_data_collection       'Proteum2 V2011.2-0 (Bruker, 2001)'
_computing_data_reduction        'SAINT V7.60A (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
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker Platinum-135 area detector'
_diffrn_measured_fraction_theta_full 0.887
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Proteum R'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5080
_diffrn_reflns_theta_full        57.48
_diffrn_reflns_theta_max         57.48
_diffrn_reflns_theta_min         3.79
_diffrn_source                   'rotating anode'
_diffrn_source_current           35.0
_diffrn_source_power             1.75
_diffrn_source_target            Cu
_diffrn_source_type              'Bruker Microstar rotating anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.682
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.1022 before and 0.0489 after correction.
The Ratio of minimum to maximum transmission is 0.6517.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0800P)^2^+0.4000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1248
_reflns_number_gt                2262
_reflns_number_total             2711
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3016594_si_001.cif
_cod_data_source_block           5h_dax38
_cod_depositor_comments
'Adding full bibliography for 1508313--1508316.cif.'
_cod_original_cell_volume        1110.38(8)
_cod_database_code               1508315