Efficient Synthesis of Quinoline-Enone Esters via Copper-Catalyzed Coupling with Electron-Deficient Alkynes and Exploration of Fluorescence in Difluoroboron Complexes †
Wang, Xiaojiao; Cao, Xin; Li, Zhenjiang; Qi, Jialin; Gong, Shuwen; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00213G

data_7161097
_publ_section_title
;
 Efficient synthesis of quinoline-enone esters <i>via</i> copper-catalyzed
 coupling with electron-deficient alkynes and exploration of fluorescence
 in difluoroboron complexes.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3239
_journal_page_last               3243
_journal_paper_doi               10.1039/d6ob00213g
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C28 H30 N2 O5'
_chemical_formula_sum            'C28 H30 N2 O5'
_chemical_formula_weight         474.54
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2026-01-04 deposited with the CCDC.	2026-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                106.305(8)
_cell_angle_beta                 98.029(8)
_cell_angle_gamma                90.268(8)
_cell_formula_units_Z            4
_cell_length_a                   11.1309(17)
_cell_length_b                   12.6805(19)
_cell_length_c                   19.595(3)
_cell_measurement_reflns_used    9621
_cell_measurement_temperature    303.00
_cell_measurement_theta_max      68.004
_cell_measurement_theta_min      2.375
_cell_volume                     2625.7(7)
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      303.00
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            48516
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.524
_diffrn_reflns_theta_min         2.375
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1420 before and 0.0591 after correction.
The Ratio of minimum to maximum transmission is 0.8963.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     661
_refine_ls_number_reflns         9347
_refine_ls_number_restraints     1203
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0940P)^2^+0.7881P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.1849
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7022
_reflns_number_total             9347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00213g2.cif
_cod_data_source_block           cu_20250616_j580_0m
_cod_depositor_comments          'Adding full bibliography for 7161097.cif.'
_cod_original_cell_volume        2625.6(7)
_cod_database_code               7161097
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.900
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O7-C50 \\sim O7-C57
 with sigma of 0.02
 O7-C51 \\sim O7-C01Z
 with sigma of 0.04
 C50-C51 \\sim C57-C01Z
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O7 \\sim C50 \\sim C51 \\sim C57 \\sim C01Z: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
C21 \\sim C20 \\sim C49 \\sim C24 \\sim C52 \\sim C40 \\sim C48 \\sim C11 \\sim
C12 \\sim C42 \\sim C14 \\sim C13 \\sim C39 \\sim C41 \\sim C19 \\sim C43 \\sim
C8 \\sim C53 \\sim C25 \\sim C47 \\sim C15 \\sim C36 \\sim C10 \\sim C3 \\sim
C7 \\sim C31 \\sim C35 \\sim C44 \\sim C9 \\sim C46 \\sim C18 \\sim C22 \\sim
C54 \\sim C37 \\sim C38 \\sim C56 \\sim C45 \\sim C6 \\sim C2 \\sim C30 \\sim
C34 \\sim C27 \\sim C16 \\sim C5 \\sim C29 \\sim C4 \\sim C17 \\sim C32 \\sim
C55 \\sim C33 \\sim C1 \\sim C26 \\sim C50 \\sim C28 \\sim C23 \\sim C51:
within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 3.8A
4. Others
 Sof(C57)=Sof(H57A)=Sof(H57B)=Sof(C01Z)=Sof(H01A)=Sof(H01B)=Sof(H01C)=1-FVAR(1)
 Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H51C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C2(H2A,H2B), C30(H30A,H30B), C50(H50A,H50B), C57(H57A,H57B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C19(H19), C43(H43), C47(H47), C15(H15), C10(H10), C44(H44),
 C9(H9), C46(H46), C18(H18), C37(H37), C38(H38), C45(H45), C6(H6), C34(H34),
 C16(H16), C5(H5), C4(H4A), C17(H17), C32(H32), C33(H33)
5.c Idealised Me refined as rotating group:
 C54(H54A,H54B,H54C), C56(H56A,H56B,H56C), C27(H27A,H27B,H27C), C29(H29A,H29B,
 H29C), C55(H55A,H55B,H55C), C1(H1A,H1B,H1C), C26(H26A,H26B,H26C), C28(H28A,
 H28B,H28C), C23(H23A,H23B,H23C), C51(H51A,H51B,H51C), C01Z(H01A,H01B,H01C)
;
_shelx_res_checksum              73589
_olex2_submission_special_instructions 'No special instructions were received'