Synthesis of novel polysubstituted N-benzyl-1H-pyrroles via a cascade reaction of alkynyl Fischer carbenes with α-imino glycine methyl esters.
de la Cruz, Fabiola N.; López, Julio; Jiménez-Halla, J Óscar C; Flores-Álamo, Marcos; Tamaríz, Joaquín; Delgado, Francisco; Vázquez, Miguel A; Organic & biomolecular chemistry 13 (2015) 11753–11760; doi:10.1039/c5ob01655j

data_7154750
_publ_section_title
;
 Synthesis of novel polysubstituted N-benzyl-1H-pyrroles via a cascade
 reaction of alkynyl Fischer carbenes with \a-imino glycine methyl esters.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              11753
_journal_page_last               11760
_journal_paper_doi               10.1039/c5ob01655j
_journal_volume                  13
_journal_year                    2015
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H22 F1 N1 O4'
_chemical_formula_sum            'C22 H22 F N O4'
_chemical_formula_weight         383.41
_chemical_name_systematic
;
 Methyl 5-ethoxy-1-(4-fluorobenzyl)-3-(4-methoxyphenyl)
 -pyrrole-2-carboxylate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2013-05-29T19:16:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2013-11-06 deposited with the CCDC.
2015-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.206(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.3264(13)
_cell_length_b                   8.0732(5)
_cell_length_c                   10.6434(6)
_cell_measurement_reflns_used    2461
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3.4892
_cell_measurement_wavelength     0.71073
_cell_volume                     2002.9(2)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0299171
_diffrn_orient_matrix_UB_12      -0.0150744
_diffrn_orient_matrix_UB_13      -0.0065986
_diffrn_orient_matrix_UB_21      -0.0054875
_diffrn_orient_matrix_UB_22      0.075394
_diffrn_orient_matrix_UB_23      0.0315218
_diffrn_orient_matrix_UB_31      -0.0008985
_diffrn_orient_matrix_UB_32      0.0424656
_diffrn_orient_matrix_UB_33      -0.058421
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8362
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.5
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.5097
_exptl_crystal_size_mid          0.3157
_exptl_crystal_size_min          0.2954
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.03
_refine_ls_extinction_coef       0.044(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.5652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                2573
_reflns_number_total             3644
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c5ob01655j2.cif
_cod_data_source_block           rx-37
_cod_depositor_comments          'Adding full bibliography for 7154750.cif.'
_cod_database_code               7154750