Visible light-driven dearomative ring expansion of (aza)arenes to access dihydrofuran-based polycyclic compounds.
Zhang, Linghong; You, Mengdi; Ban, Xu; Zhao, Xiaowei; Yin, Yanli; Cao, Shanshan; Jiang, Zhiyong; Chemical science 15 (2024) 8828–8834; doi:10.1039/d4sc00748d

data_1571584
_publ_section_title
;
 Visible light-driven dearomative ring expansion of (aza)arenes to access
 dihydrofuran-based polycyclic compounds.
;
_journal_issue                   23
_journal_name_full               'Chemical science'
_journal_page_first              8828
_journal_page_last               8834
_journal_paper_doi               10.1039/d4sc00748d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C28 H31 F3 O'
_chemical_formula_sum            'C28 H31 F3 O'
_chemical_formula_weight         440.53
_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     iterative
_audit_creation_date             2023-08-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-08-02 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.074(4)
_cell_angle_beta                 92.871(4)
_cell_angle_gamma                96.049(5)
_cell_formula_units_Z            2
_cell_length_a                   9.1987(6)
_cell_length_b                   11.0072(6)
_cell_length_c                   12.2093(6)
_cell_measurement_reflns_used    3615
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.0840
_cell_measurement_theta_min      4.0220
_cell_volume                     1227.76(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00  90.00   93
  2  \w    -71.00  39.00   1.00    1.00    --  -33.50  19.00  30.00  110
  3  \w    -62.00  36.00   1.00    1.00    --  -33.50  77.00  60.00   98
  4  \w   -108.00 -35.00   1.00    1.00    --  -33.50 178.00 -30.00   73
  5  \w   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00-150.00   87
  6  \w   -108.00 -35.00   1.00    1.00    --  -33.50 178.00-180.00   73
  7  \w      1.00  76.00   1.00    1.00    --   36.47 -99.00-180.00   75
  8  \w      1.00  76.00   1.00    1.00    --   36.47 -99.00 -30.00   75
  9  \w     38.00 128.00   1.00    5.00    --  108.00 -45.00  60.00   90
 10  \w     38.00 107.00   1.00    5.00    --  108.00 -94.00   0.00   69
 11  \w    101.00 177.00   1.00    5.00    --  108.00  77.00   0.00   76
 12  \w     71.00 107.00   1.00    5.00    --  108.00 -94.00  90.00   36
 13  \w     41.00 105.00   1.00    5.00    --  108.00 -94.00-150.00   64
 14  \w     63.00 126.00   1.00    5.00    --  108.00 -61.00 -30.00   63
 15  \w     42.00 128.00   1.00    5.00    --  108.00 -45.00-120.00   86
 16  \w    126.00 166.00   1.00    5.00    --  108.00 111.00  30.00   40
 17  \w     89.00 170.00   1.00    5.00    --  108.00  45.00  60.00   81
 18  \w    105.00 157.00   1.00    5.00    --  108.00  61.00-180.00   52
 19  \w     65.00  91.00   1.00    5.00    --  108.00 178.00-180.00   26
 20  \w     75.00 105.00   1.00    5.00    --  108.00 -94.00  30.00   30
 21  \w     64.00 109.00   1.00    5.00    --  108.00-111.00 -30.00   45
 22  \w     68.00 105.00   1.00    5.00    --  108.00 -94.00 150.00   37
 23  \w     72.00 177.00   1.00    5.00    --  108.00   0.00 -30.00  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0978974000
_diffrn_orient_matrix_UB_12      -0.1167849000
_diffrn_orient_matrix_UB_13      0.0285323000
_diffrn_orient_matrix_UB_21      -0.1372199000
_diffrn_orient_matrix_UB_22      0.0634575000
_diffrn_orient_matrix_UB_23      -0.0322972000
_diffrn_orient_matrix_UB_31      0.0047381000
_diffrn_orient_matrix_UB_32      -0.0463040000
_diffrn_orient_matrix_UB_33      -0.1187635000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8391
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         3.625
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4357
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0731
_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^)+(0.1306P)^2^+0.3075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2102
_refine_ls_wR_factor_ref         0.2280
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3413
_reflns_number_total             4357
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00748d2.cif
_cod_data_source_block           zhlh202308_auto
_cod_depositor_comments
'Adding full bibliography for 1571583--1571585.cif.'
_cod_database_code               1571584
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4F3
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C13(H13), C15(H15)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              3344
_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 1.257
_oxdiff_exptl_absorpt_empirical_full_min 0.846