One-pot synthesis of pyrrole-2-carboxylates and -carboxamides via an electrocyclization/oxidation sequence.
Imbri, Dennis; Netz, Natalie; Kucukdisli, Murat; Kammer, Lisa Marie; Jung, Philipp; Kretzschmann, Annika; Opatz, Till; The Journal of organic chemistry 79 (2014) 11750–11758; doi:10.1021/jo5021823

data_4030169
_publ_section_title
;
 One-pot synthesis of pyrrole-2-carboxylates and -carboxamides via an
 electrocyclization/oxidation sequence.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11750
_journal_page_last               11758
_journal_paper_doi               10.1021/jo5021823
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C22 H23 F N2 O2'
_chemical_formula_sum            'C22 H23 F N2 O2'
_chemical_formula_weight         366.42
_chemical_name_systematic
;
5-(4-Fluorophenyl)-3-(4-methoxyphenyl)-<i>N</i>-(2-methylpropyl)-
1<i>H</i>-pyrrole-2-carboxamide
;
_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   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                80.454(7)
_cell_angle_beta                 84.455(6)
_cell_angle_gamma                76.543(6)
_cell_formula_units_Z            4
_cell_length_a                   11.7244(9)
_cell_length_b                   13.1147(10)
_cell_length_c                   13.1273(11)
_cell_measurement_reflns_used    15648
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      28.68
_cell_measurement_theta_min      2.45
_cell_volume                     1932.3(3)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      213(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      ' 211 frames, detector distance = 60 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19391
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.455
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         9316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0676P)^2^+0.1978P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1394
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5916
_reflns_number_total             9316
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5021823_si_002.cif
_cod_data_source_block           9c
_cod_depositor_comments
'Adding full bibliography for 4030168--4030169.cif.'
_cod_database_code               4030169
_shelx_estimated_absorpt_t_min   0.949
_shelx_estimated_absorpt_t_max   0.966
_shelxl_version_number           2014-3
_shelx_res_checksum              1426
_shelx_hkl_checksum              77057