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_7161017
_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         'C33 H29 N O5 S'
_chemical_formula_sum            'C33 H29 N O5 S'
_chemical_formula_weight         551.63
_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             2025-02-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-09-18 deposited with the CCDC.	2026-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.370(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.361(2)
_cell_length_b                   11.211(2)
_cell_length_c                   22.472(4)
_cell_measurement_reflns_used    9859
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      26.64
_cell_measurement_theta_min      2.55
_cell_volume                     2859.8(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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      298.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0761
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            77264
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         1.794
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6163
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1251 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.8266.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         6599
_refine_ls_number_restraints     325
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0487P)^2^+1.5741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1379
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4814
_reflns_number_total             6599
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00097e2.cif
_cod_data_source_block           drb_gm_722_0m
_cod_depositor_comments
'Adding full bibliography for 7161016--7161017.cif.'
_cod_original_cell_volume        2859.9(9)
_cod_database_code               7161017
_shelx_shelxl_version_number     2019/3
_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. Restrained distances
 C11-O2 \\sim C11-O5
 with sigma of 0.02
 O2-C31 \\sim O5-C31
 with sigma of 0.02
 O2-C31 \\sim O2-C33
 with sigma of 0.02
 C31-C2 \\sim C33-C2
 with sigma of 0.02
 C31-O5 \\sim C33-O5
 with sigma of 0.02
 C31-C2 \\sim C31-C17
 with sigma of 0.02
 C2-O5 \\sim C17-O5
 with sigma of 0.02
 C2-C33 \\sim C17-C33
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(O5) = Uanis(O2) = Uanis(C31) = Uanis(C33) = Uanis(C2) = Uanis(C17)
4. Others
 Sof(O5)=1-FVAR(1)
 Sof(O2)=FVAR(1)
 Sof(C33)=Sof(H33A)=Sof(H33B)=1-FVAR(2)
 Sof(C31)=Sof(H31A)=Sof(H31B)=FVAR(2)
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=1-FVAR(3)
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C16(H16)
5.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C31(H31A,H31B), C33(H33A,H33B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C9(H9), C13(H13), C18(H18), C19(H19), C21(H21),
 C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C32(H32),
  C34(H34), C35(H35)
5.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_shelx_res_checksum              73140
_olex2_submission_special_instructions 'No special instructions were received'