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_1571583
_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         'C16 H10 Br F3 O'
_chemical_formula_sum            'C16 H10 Br F3 O'
_chemical_formula_weight         355.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-07-28 deposited with the CCDC.	2024-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.475(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.291(2)
_cell_length_b                   6.2878(6)
_cell_length_c                   15.4937(18)
_cell_measurement_reflns_used    1307
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.1470
_cell_measurement_theta_min      5.6920
_cell_volume                     1420.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    'ShelXS (Sheldrick, 2008)'
_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 -32.00   1.00    1.00    --  -33.50 178.00-180.00   76
  2  \w   -102.00 -37.00   1.00    1.00    --  -33.50 -57.00-120.00   65
  3  \w    -87.00 -32.00   1.00    1.00    --  -33.50 178.00 -90.00   55
  4  \w    -96.00 -65.00   1.00    1.00    --  -33.50 -57.00   0.00   31
  5  \w     63.00 107.00   1.00    1.00    --   36.54 178.00  30.00   44
  6  \w     57.00 111.00   1.00    1.00    --   36.54 178.00-180.00   54
  7  \w     20.00  64.00   1.00    1.00    --   36.54 -77.00   0.00   44
  8  \w    -21.00   8.00   1.00    1.00    --   36.54 -77.00   0.00   29
  9  \w     77.00 106.00   1.00    1.00    --   36.54  37.00-120.00   29
 10  \w     60.00  97.00   1.00    1.00    --   36.54 178.00 -60.00   37
 11  \w     15.00  49.00   1.00    1.00    --   36.54  37.00-120.00   34
 12  \w    -10.00  35.00   1.00    1.00    --   36.54 -57.00   0.00   45
 13  \w     38.00  81.00   1.00    6.50    --  108.00 -94.00 150.00   43
 14  \w     80.00 134.00   1.00    6.50    --  108.00 -30.00 120.00   54
 15  \w    152.00 177.00   1.00    6.50    --  108.00  77.00 -30.00   25
 16  \w     83.00 144.00   1.00    6.50    --  108.00  77.00 -30.00   61
 17  \w     43.00  70.00   1.00    6.50    --  108.00 -30.00 120.00   27
 18  \w     58.00  85.00   1.00    6.50    --  108.00 -94.00-150.00   27
 19  \w     68.00 120.00   1.00    6.50    --  108.00 178.00 150.00   52
 20  \w     95.00 169.00   1.00    6.50    --  108.00  61.00 -90.00   74
 21  \w     65.00  98.00   1.00    6.50    --  108.00 -94.00  30.00   33
 22  \w     41.00 126.00   1.00    6.50    --  108.00 -61.00-150.00   85
;
_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      -0.0979129000
_diffrn_orient_matrix_UB_12      -0.0505658000
_diffrn_orient_matrix_UB_13      -0.0149782000
_diffrn_orient_matrix_UB_21      -0.0066630000
_diffrn_orient_matrix_UB_22      -0.1797837000
_diffrn_orient_matrix_UB_23      -0.0705990000
_diffrn_orient_matrix_UB_31      0.0390649000
_diffrn_orient_matrix_UB_32      -0.1584690000
_diffrn_orient_matrix_UB_33      0.0845420000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5416
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         5.714
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.235
_exptl_absorpt_correction_T_max  0.756
_exptl_absorpt_correction_T_min  0.444
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.660
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.339
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.078
_refine_diff_density_max         1.104
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0994P)^2^+0.2603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1743
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1784
_reflns_number_total             2534
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00748d2.cif
_cod_data_source_block           202107195
_cod_depositor_comments
'Adding full bibliography for 1571583--1571585.cif.'
_cod_database_code               1571583
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C16H10O1F3Br1
_chemical_oxdiff_usercomment     r
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 Br1A-C3A
 1.9 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(C4A)
Uanis(C5) = Uanis(C5A)
Uanis(C2) = Uanis(C2A)
Uanis(C1) = Uanis(C1A)
Uanis(C3) = Uanis(C3A)
Uanis(C6) = Uanis(C6A)
Uanis(Br1) = Uanis(Br1A)
4. Others
 Sof(Br1A)=Sof(C3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C1A)=
 Sof(H1A)=Sof(C2A)=Sof(H2A)=1-FVAR(1)
 Sof(Br1)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)=
 Sof(H5)=Sof(C6)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4A(H4A), C5A(H5A), C1A(H1A), C2A(H2A), C4(H4), C5(H5),
 C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
5.b Fitted hexagon refined as free rotating group:
 C3A(C4A,C5A,C6A,C1A,C2A)
;
_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 1.263
_oxdiff_exptl_absorpt_empirical_full_min 0.873