Synthesis of tetrasubstituted furans through a Cu/base-mediated cascade reaction from terminal alkynes and 1,2-diketones.
Fan, Jian; Liang, Xuecheng; Yao, Liangliang; Wang, Yating; Wang, Kai; Yao, Bangben; Liu, Yujun; Xu, Shuwen; Organic & biomolecular chemistry 23 (2025) 1084–1088; doi:10.1039/d4ob01785d

data_7160278
_publ_section_title
;
 Synthesis of tetrasubstituted furans through a Cu/base-mediated cascade
 reaction from terminal alkynes and 1,2-diketones.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1084
_journal_page_last               1088
_journal_paper_doi               10.1039/d4ob01785d
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C32 H24 O3, 0.05[C6H14]'
_chemical_formula_sum            'C32 H24 O3'
_chemical_formula_weight         456.51
_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     dual
_audit_creation_date             2024-05-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2024-09-24 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.18(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.436(17)
_cell_length_b                   7.306(8)
_cell_length_c                   26.63(4)
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.456
_cell_measurement_theta_min      2.150
_cell_volume                     2413(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1541
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            70026
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.726
_diffrn_reflns_theta_min         2.163
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.277
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5645
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.279
_refine_ls_R_factor_all          0.1316
_refine_ls_R_factor_gt           0.1266
_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^)+(0.1380P)^2^+2.3738P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2964
_refine_ls_wR_factor_ref         0.2999
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5254
_reflns_number_total             5645
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01785d2.cif
_cod_data_source_block           mo_20240430c_0m
_cod_depositor_comments
'Adding full bibliography for 7160277--7160278.cif.'
_cod_original_cell_volume        2414(5)
_cod_database_code               7160278
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24)
\\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.02 and sigma for terminal
atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C20(H20), C14(H14), C5(H5), C32(H32), C17(H17), C28(H28), C25(H25),
 C15(H15), C16(H16), C4(H4), C3(H3), C18(H18), C29(H29), C31(H31), C23(H23),
 C30(H30), C24(H24)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              20744
_shelx_fab_checksum              12141
_olex2_submission_special_instructions 'No special instructions were received'