Silver(i)/base-promoted propargyl alcohol-controlled regio- or stereoselective synthesis of furan-3-carboxamides and (Z)-enaminones.
Sultana, Sabera; Shim, Jae-Jin; Kim, Sung Hong; Lee, Yong Rok; Organic & biomolecular chemistry 16 (2018) 6749–6759; doi:10.1039/c8ob01791c

data_7156401
_publ_section_title
;
 Silver(i)/base-promoted propargyl alcohol-controlled regio- or
 stereoselective synthesis of furan-3-carboxamides and (Z)-enaminones.
;
_journal_issue                   36
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6749
_journal_page_last               6759
_journal_paper_doi               10.1039/c8ob01791c
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C8 H11 N O2'
_chemical_formula_weight         153.18
_chemical_melting_point          403
_chemical_name_systematic        N,2,4-Trimethylfuran-3-carboxamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-06-20 deposited with the CCDC.
2018-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.80(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0234(15)
_cell_length_b                   12.137(4)
_cell_length_c                   13.751(4)
_cell_measurement_reflns_used    3514
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.22
_cell_measurement_theta_min      3.01
_cell_volume                     826.2(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7928
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.048
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         1.503
_exptl_absorpt_coefficient_mu    0.089
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 750 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0500P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.904
_reflns_number_gt                2172
_reflns_number_total             2772
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01791c1.cif
_cod_data_source_block           SS-153-A
_cod_depositor_comments          'Adding full bibliography for 7156401.cif.'
_cod_original_cell_volume        826.1(4)
_cod_database_code               7156401
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              24801