Visible Light Induced 6π Electrocyclization: Divergent Synthesis of Seven Membered Ring Derivatives
Wang, Zongkang; Liu, Yiting; Liang, Chaoying; Yan, Yihui; Yang, Linrui; Wang, Yan; Jiang, Yakun; Wang, Chengyu; Li, Yanzhong; Green Chemistry  (2026) –; doi:10.1039/D6GC01010E

data_7251872
_publ_section_title
;
 Visible light induced 6\p electrocyclization: divergent synthesis of
 seven membered ring derivatives
;
_journal_issue                   17
_journal_name_full               'Green Chemistry'
_journal_page_first              7286
_journal_page_last               7292
_journal_paper_doi               10.1039/D6GC01010E
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C26 H23 N O4'
_chemical_formula_sum            'C26 H23 N O4'
_chemical_formula_weight         413.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-07
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-12-19 deposited with the CCDC.	2026-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.9550(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.93140(10)
_cell_length_b                   16.36590(10)
_cell_length_c                   19.2763(2)
_cell_measurement_reflns_used    31203
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      73.3330
_cell_measurement_theta_min      3.6280
_cell_volume                     4104.32(6)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -27.00  47.00   1.00    1.00    --    0.00  57.00 -90.00   74
  2  \w    -12.00  23.00   1.00    1.00    --    0.00  57.00 150.00   35
  3  \w    -33.00  88.00   1.00    1.00    --    0.00  77.00 -60.00  121
  4  \w     -2.00  33.00   1.00    1.00    --    0.00 -77.00  30.00   35
  5  \w    -33.00   6.00   1.00    1.00    --    0.00  77.00  90.00   39
  6  \w     53.00  88.00   1.00    1.00    --    0.00  57.00-180.00   35
  7  \w     52.00  86.00   1.00    1.00    --    0.00  77.00  30.00   34
  8  \w     22.00  57.00   1.00    1.00    --    0.00  77.00  90.00   35
  9  \w      7.00  49.00   1.00    1.00    --    0.00  57.00-180.00   42
 10  \w     57.00  89.00   1.00    1.00    --    0.00  57.00 150.00   32
 11  \w    -26.00   2.00   1.00    1.00    --    0.00  57.00-180.00   28
 12  \w    -33.00  46.00   1.00    1.00    --    0.00  77.00  30.00   79
 13  \w     63.00  89.00   1.00    1.00    --    0.00  77.00  90.00   26
 14  \w    100.00 126.00   1.00    1.00    --   92.10  47.00 -83.49   26
 15  \w     66.00  95.00   1.00    1.00    --   92.10  47.00 -83.49   29
 16  \w    115.00 164.00   1.00    1.00    --   92.10  48.00 106.99   49
 17  \w    152.00 178.00   1.00    1.00    --   92.10  51.00  14.57   26
 18  \w     67.00  96.00   1.00    1.00    --   92.10  51.00  14.57   29
 19  \w     66.00 103.00   1.00    1.00    --   92.10  48.00 106.99   37
 20  \w    156.00 182.00   1.00    1.00    --   92.10  48.00 -26.30   26
 21  \w     63.00 141.00   1.00    1.00    --   92.10  64.00  33.41   78
 22  \w     65.00  91.00   1.00    1.00    --   92.10  57.00 -65.80   26
 23  \w     57.00  82.00   1.00    1.00    --   92.10  81.00 -42.08   25
 24  \w     99.00 182.00   1.00    1.00    --   92.10  81.00 -42.08   83
 25  \w      4.00 120.00   1.00    1.00    --   92.10 -61.00 -90.00  116
 26  \w     59.00  85.00   1.00    1.00    --   92.10  77.00 150.00   26
 27  \w      3.00 128.00   1.00    1.00    --   92.10 -82.00 -90.00  125
 28  \w     33.00 120.00   1.00    1.00    --   92.10 -82.00 150.00   87
 29  \w     57.00  83.00   1.00    1.00    --   92.10  82.00   0.00   26
 30  \w     63.00  93.00   1.00    1.00    --   92.10  64.00 -21.49   30
 31  \w     67.00 119.00   1.00    1.00    --   92.10  53.00  26.47   52
 32  \w    143.00 177.00   1.00    1.00    --   92.10  63.00 139.95   34
 33  \w    127.00 180.00   1.00    1.00    --   92.10  48.00-100.92   53
 34  \w     64.00 177.00   1.00    1.00    --   92.10  61.00-156.26  113
 35  \w    106.00 182.00   1.00    1.00    --   92.10  82.00-150.00   76
 36  \w     57.00  83.00   1.00    1.00    --   92.10  82.00-150.00   26
 37  \w     64.00  90.00   1.00    1.00    --   92.10  63.00 139.95   26
 38  \w    104.00 170.00   1.00    1.00    --   92.10  82.00 -90.00   66
 39  \w     57.00  82.00   1.00    1.00    --   92.10  82.00 120.00   25
 40  \w     59.00  84.00   1.00    1.00    --   92.10  77.00 -60.00   25
 41  \w    115.00 182.00   1.00    1.00    --   92.10  77.00 -60.00   67
 42  \w     59.00  85.00   1.00    1.00    --   92.10  77.00   0.00   26
 43  \w     57.00  82.00   1.00    1.00    --   92.10  82.00-180.00   25
 44  \w     57.00  91.00   1.00    1.00    --   92.10  82.00  30.00   34
 45  \w     59.00  84.00   1.00    1.00    --   92.10  77.00  90.00   25
 46  \w     59.00  84.00   1.00    1.00    --   92.10  77.00-120.00   25
 47  \w     57.00  82.00   1.00    1.00    --   92.10  82.00 -30.00   25
 48  \w      7.00  32.00   1.00    1.00    --   92.10 -82.00   0.00   25
 49  \w     56.00 128.00   1.00    1.00    --   92.10 -82.00   0.00   72
 50  \w     57.00  82.00   1.00    1.00    --   92.10  82.00 -90.00   25
 51  \w    155.00 180.00   1.00    1.00    --   92.10  56.00-119.68   25
 52  \w     67.00  96.00   1.00    1.00    --   92.10  48.00-100.92   29
 53  \w     57.00  83.00   1.00    1.00    --   92.10  82.00 150.00   26
 54  \w     64.00  93.00   1.00    1.00    --   92.10  61.00 -60.00   29
 55  \w     57.00  84.00   1.00    1.00    --   92.10  82.00  60.00   27
 56  \w     65.00  91.00   1.00    1.00    --   92.10  56.00-119.68   26
 57  \w     59.00  84.00   1.00    1.00    --   92.10  77.00-180.00   25
 58  \w     59.00  84.00   1.00    1.00    --   92.10  77.00  30.00   25
 59  \w     57.00  83.00   1.00    1.00    --   92.10  82.00-120.00   26
 60  \w    125.00 182.00   1.00    1.00    --   92.10  82.00   0.00   57
 61  \w     44.00 103.00   1.00    1.00    --   92.10 -82.00-150.00   59
 62  \w     11.00 128.00   1.00    1.00    --   92.10 -82.00  60.00  117
 63  \w    147.00 172.00   1.00    1.00    --   92.10  47.00 -83.49   25
 64  \w     62.00  92.00   1.00    1.00    --   92.10  68.00 116.23   30
 65  \w     67.00  97.00   1.00    1.00    --   92.10  45.00 -60.00   30
 66  \w     66.00  97.00   1.00    1.00    --   92.10  37.00  98.59   31
 67  \w     68.00 104.00   1.00    1.00    --   92.10  48.00 -26.30   36
 68  \w     66.00 142.00   1.00    1.00    --   92.10  45.00-180.00   76
 69  \w     68.00  94.00   1.00    1.00    --   92.10  48.00-149.53   26
 70  \w     65.00 182.00   1.00    1.00    --   92.10  35.00 152.23  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0095198000
_diffrn_orient_matrix_UB_12      -0.0213062000
_diffrn_orient_matrix_UB_13      0.0800284000
_diffrn_orient_matrix_UB_21      0.1110411000
_diffrn_orient_matrix_UB_22      0.0326173000
_diffrn_orient_matrix_UB_23      0.0289772000
_diffrn_orient_matrix_UB_31      -0.0398105000
_diffrn_orient_matrix_UB_32      0.0857584000
_diffrn_orient_matrix_UB_33      0.0089320000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            49416
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         3.650
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.00118(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3668
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0336P)^2^+3.9499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3522
_reflns_number_total             3668
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6gc01010e2.cif
_cod_data_source_block           exp_4792_auto
_cod_depositor_comments
'Adding full bibliography for 7251870--7251872.cif.'
_cod_original_cell_volume        4104.31(6)
_cod_database_code               7251872
_shelx_shelxl_version_number     2018/3
_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, All O(H) groups
2. Restrained distances
 O3-C25 \\sim O3-C25A
 with sigma of 0.02
 C25-C26 \\sim C25A-C26A
 with sigma of 0.02
 O3-C26 \\sim O3-C26A
 with sigma of 0.04
3. Rigid bond restraints
 O3, O4, C24, C25, C26, C25A, C26A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
O3 \\sim O4 \\sim C24 \\sim C25 \\sim C26 \\sim C25A \\sim C26A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
5. Others
 Sof(C25A)=Sof(H25C)=Sof(H25D)=Sof(C26A)=Sof(H26D)=Sof(H26E)=Sof(H26F)=1-FVAR(1)
 Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C25(H25A,H25B), C25A(H25C,H25D)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12)
6.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C26(H26A,H26B,H26C), C26A(H26D,H26E,H26F)
6.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.771