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_7245527
_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         'C18 H13 N O'
_chemical_formula_sum            'C18 H13 N O'
_chemical_formula_weight         259.29
_chemical_melting_point          357.0(10)
_chemical_name_systematic        5-Methyl-2,4-diphenylfuran-3-carbonitrile
_chemical_properties_physical    Moisture-sensitive,Light-sensitive
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-01 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.0860(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.7123(2)
_cell_length_b                   15.2241(4)
_cell_length_c                   18.7948(5)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.31
_cell_measurement_theta_min      3.76
_cell_volume                     2727.16(12)
_computing_cell_refinement       'APEX3 v2018.2 (Bruker, 2018)'
_computing_data_collection       'APEX3 v2018.2 (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.37A  (Bruker, 2018)'
_computing_molecular_graphics
'Ortep-3 Ver 2.02 L.J. Farrugia (1997) J. Appl. Cryst. 30, 565'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2018 (Bruker, 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 52.0833
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type
'Bruker D8 Venture \k-geometry diffractometer 208039-01'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13468
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.328
_diffrn_reflns_theta_min         3.765
_diffrn_source                   'micro-focus X-ray source'
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1088
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate/heptane'
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.171
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0695
_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^)+(0.0506P)^2^+1.6590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3828
_reflns_number_total             4942
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra04938d2.cif
_cod_data_source_block           020TOR22
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '356-358' was changed to
'357.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7245527
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.772
_shelx_estimated_absorpt_t_max   0.902
_shelx_res_checksum              81621