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_1508316
_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 H19 N2 O, C H O3'
_chemical_formula_sum            'C23 H20 N2 O4'
_chemical_formula_weight         388.41
_chemical_name_systematic
;
1-(2-(4-methoxy)-4-phenyl-1H-pyrrol-3-yl)piridinium hydrocarbonate
;
_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             2012-01-30
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  Olex2 1.1-beta
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
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_cell_angle_alpha                66.320(8)
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_cell_angle_gamma                84.878(7)
_cell_formula_units_Z            2
_cell_length_a                   8.5504(7)
_cell_length_b                   10.5045(8)
_cell_length_c                   11.7210(11)
_cell_measurement_reflns_used    1825
_cell_measurement_temperature    120
_cell_measurement_theta_max      32.3811
_cell_measurement_theta_min      2.7527
_cell_volume                     933.35(15)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_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
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -93.00  -11.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867  -57.0000   60.0000 82

  2 omega  -95.00  -66.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867  -57.0000   30.0000 29

  3 omega  -77.00  -36.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867 -179.0000  150.0000 41

  4 omega  -42.00   42.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.1867   57.0000 -180.0000 84

  5 omega   27.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -100.0000    0.0000 42

  6 omega   13.00   62.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -101.0000  -70.0000 49

  7 omega   43.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -100.0000 -180.0000 26

  8 omega   37.00   63.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679 -101.0000  109.0000 26

  9 omega  -33.00   52.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.9679  -38.0000  -90.0000 85
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       \w-scan
_diffrn_orient_matrix_UB_11      -0.0258626000
_diffrn_orient_matrix_UB_12      0.0024984000
_diffrn_orient_matrix_UB_13      0.0614713000
_diffrn_orient_matrix_UB_21      0.0633480000
_diffrn_orient_matrix_UB_22      -0.0451456000
_diffrn_orient_matrix_UB_23      0.0203462000
_diffrn_orient_matrix_UB_31      0.0515834000
_diffrn_orient_matrix_UB_32      0.0582479000
_diffrn_orient_matrix_UB_33      -0.0207173000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_xray_symbol    Mo
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0950
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9230
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.76
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_type              'sealed tube'
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         4954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0571
_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^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1156
_reflns_number_gt                3310
_reflns_number_total             4954
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3016594_si_001.cif
_cod_data_source_block           15_dax45
_cod_depositor_comments
'Adding full bibliography for 1508313--1508316.cif.'
_cod_original_cell_volume        933.35(14)
_cod_database_code               1508316
_chemical_oxdiff_formula         'C22 H18 N2 O1'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44