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_7161103
_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         'C44 H34 N2 O6 S2'
_chemical_formula_sum            'C44 H34 N2 O6 S2'
_chemical_formula_weight         750.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-22
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-03-13 deposited with the CCDC.	2026-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.338(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1396(5)
_cell_length_b                   16.5438(8)
_cell_length_c                   23.8646(12)
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.475
_cell_measurement_theta_min      2.846
_cell_volume                     3925.1(3)
_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      170.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0379
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            51500
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.636
_diffrn_reflns_theta_min         3.286
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_exptl_absorpt_coefficient_mu    1.070
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1135 before and 0.0548 after correction.
The Ratio of minimum to maximum transmission is 0.8944.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       needle
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         8990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0563P)^2^+1.6072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1121
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7532
_reflns_number_total             8990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00444j2.cif
_cod_data_source_block           240120_fjl_50_1_3_0m
_cod_depositor_comments
'Adding full bibliography for 7161103--7161104.cif.'
_cod_database_code               7161103
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.910
_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.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C16(H16), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23), C27(H27), C28(H28), C30(H30), C31(H31),
  C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C40(H40), C41(H41),
 C42(H42), C43(H43), C44(H44)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C32(H32A,H32B,H32C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 172 electrons were 
found in a volume of 518\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1[CH2Cl2] per Asymmetric Unit 
which account for 168 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              72683
_shelx_fab_checksum              68428
_olex2_submission_special_instructions 'No special instructions were received'