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_4030168
_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         'C19 H15 Cl N2 O4'
_chemical_formula_sum            'C19 H15 Cl N2 O4'
_chemical_formula_weight         370.78
_chemical_name_systematic
;
Ethyl 5-(4-chlorophenyl)-3-(3-nitrophenyl)-1<i>H</i>-pyrrole-2-
carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 103.1103(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2411(7)
_cell_length_b                   7.7513(5)
_cell_length_c                   19.5834(12)
_cell_measurement_reflns_used    5318
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.9613
_cell_measurement_theta_min      2.3456
_cell_volume                     1661.89(18)
_computing_cell_refinement       'Apex II suite'
_computing_data_collection       'Apex II suite'
_computing_data_reduction        'Apex II suite'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Smart APEX II'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15311
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.962
_diffrn_reflns_theta_min         1.923
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.6539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0906
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3336
_reflns_number_total             3991
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5021823_si_002.cif
_cod_data_source_block           6c
_cod_depositor_comments
'Adding full bibliography for 4030168--4030169.cif.'
_cod_database_code               4030168
_shelx_estimated_absorpt_t_min   0.904
_shelx_estimated_absorpt_t_max   0.965
_shelxl_version_number           2014-3
_shelx_res_checksum              6739
_shelx_hkl_checksum              39519