Ynones as versatile electrophiles for the divergent synthesis of 4<i>H</i>-chromenes and 1,4-dihydroquinolines.
Mishra, Gitanjali; Indu, Potnuru; Muduli, Gitanjali; Thirupathi, Barla; Organic & biomolecular chemistry 24 (2026) 2481–2486; doi:10.1039/d6ob00097e

data_7161016
_publ_section_title
;
 Ynones as versatile electrophiles for the divergent synthesis of
 4<i>H</i>-chromenes and 1,4-dihydroquinolines.
;
_journal_issue                   12
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2481
_journal_page_last               2486
_journal_paper_doi               10.1039/d6ob00097e
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C27 H21 F3 O4'
_chemical_formula_sum            'C27 H21 F3 O4'
_chemical_formula_weight         466.44
_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             2025-03-21
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2025-09-18 deposited with the CCDC.	2026-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                70.5120(10)
_cell_angle_beta                 83.8130(10)
_cell_angle_gamma                69.3340(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4931(3)
_cell_length_b                   11.6134(5)
_cell_length_c                   13.1704(5)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      25.287
_cell_measurement_theta_min      2.563
_cell_volume                     1145.75(8)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      300.0
_diffrn_measured_fraction_theta_full 50
_diffrn_measured_fraction_theta_max 0.651
_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  0.1338
_diffrn_reflns_av_unetI/netI     0.2949
_diffrn_reflns_Laue_measured_fraction_full 0.651
_diffrn_reflns_Laue_measured_fraction_max 0.651
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4265
_diffrn_reflns_point_group_measured_fraction_full 0.651
_diffrn_reflns_point_group_measured_fraction_max 0.651
_diffrn_reflns_theta_full        24.664
_diffrn_reflns_theta_max         24.664
_diffrn_reflns_theta_min         1.640
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0855 before and 0.0572 after correction. The Ratio of minimum to maximum transmission is 0.7704. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       needle
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         2533
_refine_ls_number_restraints     270
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.2837
_refine_ls_R_factor_gt           0.0908
_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^)+(0.1261P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2126
_refine_ls_wR_factor_ref         0.3045
_reflns_Friedel_coverage         0.000
_reflns_number_gt                821
_reflns_number_total             2533
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00097e2.cif
_cod_data_source_block           ext69_0m
_cod_depositor_comments
'Adding full bibliography for 7161016--7161017.cif.'
_cod_database_code               7161016
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C26(H26A,H26B)
3.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C11(H11), C15(H15), C12(H12), C18(H18), C3(H3), C5(H5), C14(H14),
 C19(H19), C2(H2), C4(H4), C20(H20), C21(H21)
3.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              1775
_olex2_submission_special_instructions 'No special instructions were received'