Divergent copper-catalyzed syntheses of 3-carboxylpyrroles and 3-cyanofurans from O-acetyl oximes and β-ketoesters/nitriles
Almaraz-Ortiz, Wilfrido E.; Ramos Orea, Aldahir; Casadiego-Díaz, Oscar; Reyes-Salgado, Agustín; Mejía-Galindo, Arturo; Torres-Ochoa, Rubén O.; RSC Advances 12 (2022) 26673–26679; doi:10.1039/D2RA04938D

data_7245528
_publ_section_title
;
 Divergent copper-catalyzed syntheses of 3-carboxylpyrroles and
 3-cyanofurans from O-acetyl oximes and \b-ketoesters/nitriles
;
_journal_issue                   41
_journal_name_full               'RSC Advances'
_journal_page_first              26673
_journal_page_last               26679
_journal_paper_doi               10.1039/D2RA04938D
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C14 H15 N O2'
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.27
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2022-06-08 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.7740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.57260(10)
_cell_length_b                   12.6658(2)
_cell_length_c                   12.7853(2)
_cell_measurement_reflns_used    9874
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.59
_cell_measurement_theta_min      2.26
_cell_volume                     1224.84(3)
_computing_cell_refinement       'APEX3 v2019.1-0(Bruker, 2019)'
_computing_data_collection       'APEX3 v2019.1-0(Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2014)'
_computing_molecular_graphics    'SHELXLe (H\"ubschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 83.333
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25655
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.972
_diffrn_reflns_theta_min         2.265
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_correction_T_min  0.7099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.299
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         5361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0624P)^2^+0.2569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4572
_reflns_number_total             5361
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra04938d2.cif
_cod_data_source_block           114TOO22
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7245528
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.966
_shelx_estimated_absorpt_t_max   0.983
_shelx_res_checksum              79207