One-Pot Synthesis of 6H-Benzo[c]chromene and 6,7dihydrodibenzo[b,d]oxepine Scaffolds through Sequence Reaction of Oxidative Dearomatization and Dienone-Phenol Rearrangement
Yang, Bowei; An, Xinkun; Zhang, Tingting; He, Xie; Li, Yiyi; Wang, Mingan; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01670C

data_7160874
_publ_section_title
;
 One-Pot Synthesis of 6H-Benzo[c]chromene and
 6,7dihydrodibenzo[b,d]oxepine Scaffolds through Sequence Reaction of
 Oxidative Dearomatization and Dienone-Phenol Rearrangement
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01670C
_journal_year                    2025
_chemical_formula_moiety         'C14 H11 F O2'
_chemical_formula_sum            'C14 H11 F O2'
_chemical_formula_weight         230.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2025-09-12
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2025-10-15 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.7379(4)
_cell_length_b                   10.0334(3)
_cell_length_c                   16.1142(4)
_cell_measurement_reflns_used    2014
_cell_measurement_temperature    117.30(14)
_cell_measurement_theta_max      66.4230
_cell_measurement_theta_min      5.4740
_cell_volume                     2221.15(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      117.30(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9743
_diffrn_measurement_details
;
  1 omega  -29.00   -3.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000  -90.0000 26

  2 omega   -1.00   55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -37.0000  -90.0000 56

  3 omega  100.00  125.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -77.0000 -120.0000 25

  4 omega   55.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919 -178.0000  -90.0000 52

  5 omega   32.00   57.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -77.0000 -120.0000 25

  6 omega   45.00   80.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -30.0000   60.0000 35

  7 omega   75.00  166.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477   15.0000  150.0000 91

  8 omega   74.00  165.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477   77.0000    0.0000 91

  9 omega   60.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000   90.0000 38

 10 omega   48.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   57.0000 -120.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0682288000
_diffrn_orient_matrix_UB_12      0.0332486000
_diffrn_orient_matrix_UB_13      0.0729017000
_diffrn_orient_matrix_UB_21      -0.0612144000
_diffrn_orient_matrix_UB_22      0.1246733000
_diffrn_orient_matrix_UB_23      0.0196479000
_diffrn_orient_matrix_UB_31      -0.0646344000
_diffrn_orient_matrix_UB_32      -0.0831444000
_diffrn_orient_matrix_UB_33      0.0586247000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4512
_diffrn_reflns_theta_full        66.46
_diffrn_reflns_theta_max         66.46
_diffrn_reflns_theta_min         5.49
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.2803P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                1672
_reflns_number_total             1907
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5ob01670c2.cif
_cod_data_source_block           exp_10119
_cod_original_cell_volume        2221.14(12)
_cod_database_code               7160874
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.93