Novel and rapid approach for benzanthrone synthesis: BBr3-promoted annulation of 8-aryl-1-naphthoic acid derivatives
An, Xinkun; Ma, Haoyun; Cui, Guoen; Zhang, Tingting; Xu, Leichuan; Wang, Mingan; New Journal of Chemistry 48 (2024) 1741–1756; doi:10.1039/D3NJ03905F

data_7062918
_publ_section_title
;
 Novel and rapid approach for benzanthrone synthesis: BBr3-promoted
 annulation of 8-aryl-1-naphthoic acid derivatives
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1741
_journal_page_last               1756
_journal_paper_doi               10.1039/D3NJ03905F
_journal_volume                  48
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H14 O2'
_chemical_formula_sum            'C19 H14 O2'
_chemical_formula_weight         274.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-07-01
_audit_creation_method
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  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2022-07-04 deposited with the CCDC.	2023-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.2162(5)
_cell_length_b                   14.4562(15)
_cell_length_c                   21.1593(16)
_cell_measurement_reflns_used    770
_cell_measurement_temperature    124.3(3)
_cell_measurement_theta_max      24.2280
_cell_measurement_theta_min      4.3250
_cell_volume                     1289.7(2)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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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      124.3(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9943
_diffrn_measured_fraction_theta_max 0.8191
_diffrn_measurement_details
;
  1 omega   36.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  178.0000 -120.0000 52

  2 omega  -45.00   18.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -37.0000   30.0000 63

  3 omega  -51.00  -21.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -77.0000  -30.0000 30

  4 omega   54.00   81.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  178.0000   60.0000 27

  5 omega   40.00   71.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   57.0000 -120.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0658549000
_diffrn_orient_matrix_UB_12      0.0447416000
_diffrn_orient_matrix_UB_13      0.0038794000
_diffrn_orient_matrix_UB_21      -0.0718314000
_diffrn_orient_matrix_UB_22      -0.0033466000
_diffrn_orient_matrix_UB_23      -0.0301844000
_diffrn_orient_matrix_UB_31      -0.1369864000
_diffrn_orient_matrix_UB_32      -0.0197355000
_diffrn_orient_matrix_UB_33      0.0139852000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.1038
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5130
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.21
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82773
_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            yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2482
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0411P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                1573
_reflns_number_total             2482
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3nj03905f2.cif
_cod_data_source_block           exp_8094
_cod_depositor_comments          'Adding full bibliography for 7062918.cif.'
_cod_database_code               7062918
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07