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_7160875
_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 Cl O3'
_chemical_formula_sum            'C14 H11 Cl O3'
_chemical_formula_weight         262.68
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_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            16
_cell_length_a                   34.3840(8)
_cell_length_b                   34.3840(8)
_cell_length_c                   3.8114(4)
_cell_measurement_reflns_used    2548
_cell_measurement_temperature    117.60(14)
_cell_measurement_theta_max      66.1990
_cell_measurement_theta_min      5.4400
_cell_volume                     4506.1(5)
_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      117.60(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9923
_diffrn_measured_fraction_theta_max 0.9762
_diffrn_measurement_details
;
  1 omega   21.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -57.0000    0.0000 31

  2 omega    4.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000   90.0000 71

  3 omega   30.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -30.0000   30.0000 45

  4 omega   46.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -30.0000  -30.0000 41

  5 omega   30.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -30.0000  -60.0000 46

  6 omega   49.00   76.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  -30.0000 -150.0000 27

  7 omega  -30.00    3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -57.0000    0.0000 33

  8 omega  -20.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000  150.0000 39

  9 omega  143.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  125.0000   30.0000 25

 10 omega  101.00  137.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  125.0000    0.0000 36

 11 omega   95.00  125.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.5477  125.0000   30.0000 30

 12 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  -30.0000 26

 13 omega   -4.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -99.0000  -60.0000 75

 14 omega    1.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -99.0000 -150.0000 26

 15 omega   23.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.8017  -37.0000  150.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0159566000
_diffrn_orient_matrix_UB_12      0.0418274000
_diffrn_orient_matrix_UB_13      -0.0148115000
_diffrn_orient_matrix_UB_21      0.0383485000
_diffrn_orient_matrix_UB_22      0.0153234000
_diffrn_orient_matrix_UB_23      0.1571059000
_diffrn_orient_matrix_UB_31      0.0168065000
_diffrn_orient_matrix_UB_32      0.0048169000
_diffrn_orient_matrix_UB_33      -0.3723366000
_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  0.0382
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            5201
_diffrn_reflns_theta_full        66.24
_diffrn_reflns_theta_max         66.24
_diffrn_reflns_theta_min         5.15
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89009
_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    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1940
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0397P)^2^+3.5499P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0886
_reflns_number_gt                1726
_reflns_number_total             1940
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5ob01670c2.cif
_cod_data_source_block           exp_10123
_cod_original_cell_volume        4506.0(5)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7160875
_reflns_odcompleteness_completeness 99.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.93