Regioselective synthesis of tetrasubstituted pyrroles by 1,3-dipolar cycloaddition and spontaneous decarboxylation.
Kim, Yongju; Kim, Jonghoon; Park, Seung Bum; Organic letters 11 (2009) 17–20; doi:10.1021/ol8022193

data_1503713
_publ_section_title
;
 Regioselective synthesis of tetrasubstituted pyrroles by 1,3-dipolar
 cycloaddition and spontaneous decarboxylation.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              17
_journal_page_last               20
_journal_paper_doi               10.1021/ol8022193
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C24 H19 Br N2 O2'
_chemical_formula_weight         447.32
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'I -2ya'
_symmetry_space_group_name_H-M   'I 1 a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.914(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.979(5)
_cell_length_b                   9.253(2)
_cell_length_c                   24.348(8)
_cell_measurement_reflns_used    922
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.54
_cell_measurement_theta_min      2.20
_cell_volume                     4176(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1249
_diffrn_reflns_av_sigmaI/netI    0.2803
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11279
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    1.991
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.669
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         6249
_refine_ls_number_restraints     130
_refine_ls_restrained_S_all      0.663
_refine_ls_R_factor_all          0.1664
_refine_ls_R_factor_gt           0.0643
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0682P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1482
_refine_ls_wR_factor_ref         0.1643
_reflns_number_gt                1929
_reflns_number_total             6249
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8022193_si_004.cif
_cod_data_source_block           park2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

 Changing the _atom_site_aniso_U_23 value from "0..000" to "0.000" so
 that it is a valid floating point number:

-N12 0.082(11) 0.015(6) 0.032(7) 0..000(5) 0.014(6) -0.008(5)
+N12 0.082(11) 0.015(6) 0.032(7) 0.000(5) 0.014(6) -0.008(5)

 Saulius Gra\<zulis
 2014-01-20
;
_cod_original_sg_symbol_H-M      Ia
_cod_database_code               1503713