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_1571585
_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         'C18 H15 F3 O'
_chemical_formula_sum            'C18 H15 F3 O'
_chemical_formula_weight         304.30
_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             2024-04-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-04-16 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                75.775(6)
_cell_angle_beta                 80.036(6)
_cell_angle_gamma                89.708(5)
_cell_formula_units_Z            4
_cell_length_a                   6.9554(4)
_cell_length_b                   13.0085(7)
_cell_length_c                   17.4007(13)
_cell_measurement_reflns_used    3211
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.6650
_cell_measurement_theta_min      5.2840
_cell_volume                     1501.96(17)
_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 0.999
_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   -108.00 -35.00   1.00    1.50    --  -33.50 178.00  30.00   73
  2  \w   -108.00 -35.00   1.00    1.50    --  -33.50 178.00 -30.00   73
  3  \w   -104.00 -11.00   1.00    1.50    --  -33.50 -37.00-150.00   93
  4  \w   -103.00 -15.00   1.00    1.50    --  -33.50 149.00 145.00   88
  5  \w   -104.00 -11.00   1.00    1.50    --  -33.50 -37.00  90.00   93
  6  \w    -56.00  37.00   1.00    1.50    --  -33.50  37.00  30.00   93
  7  \w     36.00 106.00   1.00    1.50    --   36.47-149.00  98.00   70
  8  \w     61.00 110.00   1.00    1.50    --   36.47 178.00 -60.00   49
  9  \w     38.00 107.00   1.00   17.50    --  108.00 -94.00 -90.00   69
 10  \w     38.00 128.00   1.00   17.50    --  108.00 -45.00  60.00   90
 11  \w     61.00 146.00   1.00   17.50    --  108.00 178.00 -90.00   85
 12  \w     49.00 123.00   1.00   17.50    --  108.00 -45.00 -30.00   74
 13  \w    102.00 155.00   1.00   17.50    --  108.00  77.00 150.00   53
 14  \w    145.00 175.00   1.00   17.50    --  108.00 111.00  60.00   30
 15  \w    114.00 169.00   1.00   17.50    --  108.00  77.00  90.00   55
 16  \w     43.00  93.00   1.00   17.50    --  108.00 -94.00   0.00   50
 17  \w     66.00 109.00   1.00   17.50    --  108.00-111.00 150.00   43
 18  \w    129.00 175.00   1.00   17.50    --  108.00 111.00-150.00   46
 19  \w     88.00 176.00   1.00   17.50    --  108.00  45.00  30.00   88
 20  \w     89.00 172.00   1.00   17.50    --  108.00  61.00 120.00   83
 21  \w     43.00 106.00   1.00   17.50    --  108.00-111.00-120.00   63
 22  \w    101.00 169.00   1.00   17.50    --  108.00  77.00  60.00   68
 23  \w     74.00 108.00   1.00   17.50    --  108.00-111.00  60.00   34
 24  \w     98.00 145.00   1.00   17.50    --  108.00 123.00 -17.00   47
;
_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      0.2086409000
_diffrn_orient_matrix_UB_12      0.0009977000
_diffrn_orient_matrix_UB_13      -0.0477138000
_diffrn_orient_matrix_UB_21      0.0820367000
_diffrn_orient_matrix_UB_22      -0.0184886000
_diffrn_orient_matrix_UB_23      0.0788512000
_diffrn_orient_matrix_UB_31      -0.0197506000
_diffrn_orient_matrix_UB_32      -0.1208568000
_diffrn_orient_matrix_UB_33      0.0108833000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8516
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.508
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94132
_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    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         8516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0797
_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^)+(0.0607P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5199
_reflns_number_total             8516
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9685\% 
around [0.92 0.01 0.40] (reciprocal) or [1.00 -0.00 0.00] (direct)
;
_cod_data_source_file            d4sc00748d2.cif
_cod_data_source_block           202404129_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 1571583--1571585.cif.'
_cod_original_cell_volume        1501.95(17)
_cod_database_code               1571585
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N4O4F3
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.846
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5445(12)
 0.4555(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C1'(H1'), C3'(H3'), C5'(H5'), C8'(H8'), C11'(H11'), C12'(H12'),
 C13'(H13'), C14'(H14'), C15'(H15')
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C16'(H16D,H16E,H16F), C17'(H17D,
 H17E,H17F)
;
_shelx_res_checksum              82946
_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 1.117
_oxdiff_exptl_absorpt_empirical_full_min 0.898
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2