Visible light-induced synthesis of benzofuro[3,2b]pyridines from aurone-derived azadienes
Fan, Jiale; Xie, Jianwei; Lu, Ping; Wang, Yanguang; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00444J

data_7161104
_publ_section_title
;
 Visible light-induced synthesis of benzofuro[3,2-<i>b</i>]pyridines from
 aurone-derived azadienes.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3654
_journal_page_last               3658
_journal_paper_doi               10.1039/d6ob00444j
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         'C37 H26 N2 O4 S, C4 H8 O2'
_chemical_formula_sum            'C41 H34 N2 O6 S'
_chemical_formula_weight         682.76
_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             2023-11-08
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-03-16 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                108.513(4)
_cell_angle_beta                 90.182(4)
_cell_angle_gamma                98.579(5)
_cell_formula_units_Z            2
_cell_length_a                   7.8835(12)
_cell_length_b                   14.574(2)
_cell_length_c                   16.220(2)
_cell_measurement_reflns_used    6809
_cell_measurement_temperature    250.00
_cell_measurement_theta_max      56.958
_cell_measurement_theta_min      2.817
_cell_volume                     1744.8(4)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      250.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23891
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.286
_diffrn_reflns_theta_min         2.817
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1169 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.8640.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       needle
_exptl_crystal_F_000             716
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         7126
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0794P)^2^+0.2651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1551
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5180
_reflns_number_total             7126
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00444j2.cif
_cod_data_source_block           231103_fjl_42_1_0m
_cod_depositor_comments
'Adding full bibliography for 7161103--7161104.cif.'
_cod_database_code               7161104
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.836
_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, All O(H) groups
2. Restrained distances
 C40-C41
 1.53 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B)
3.b Aromatic/amide H refined with riding coordinates:
 C30(H30), C27(H27), C4(H4), C29(H29), C1(H1), C28(H28), C32(H32), C13(H13),
 C17(H17), C36(H36), C33(H33), C23(H23), C3(H3), C35(H35), C2(H2A), C16(H16),
 C14(H14), C15(H15), C19(H19), C21(H21), C22(H22), C20(H20)
3.c Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C41(H41A,H41B,H41C)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              52241
_olex2_submission_special_instructions 'No special instructions were received'