Access to functionalized benzo[<i>b</i>]fluorene/benzo[<i>a</i>]anthracene derivatives through TfOH-promoted tandem isomerization/cyclodehydration.
Sahoo, Raj Kamal; Ghosh, Sourav; Nur, Asadujjaman; Mandal, Kush; Rana, Gopal; Jana, Umasish; Organic & biomolecular chemistry 23 (2025) 10345–10356; doi:10.1039/d5ob01225b

data_7160832
_publ_section_title
;
 Access to functionalized
 benzo[<i>b</i>]fluorene/benzo[<i>a</i>]anthracene derivatives through
 TfOH-promoted tandem isomerization/cyclodehydration.
;
_journal_issue                   45
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              10345
_journal_page_last               10356
_journal_paper_doi               10.1039/d5ob01225b
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C27 H20 O4'
_chemical_formula_sum            'C27 H20 O4'
_chemical_formula_weight         408.43
_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     dual
_audit_creation_date             2024-08-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-01-29 deposited with the CCDC.	2025-10-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.349(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3527(6)
_cell_length_b                   25.4679(17)
_cell_length_c                   10.5950(7)
_cell_measurement_reflns_used    9183
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.78
_cell_measurement_theta_min      2.60
_cell_volume                     2113.2(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            71316
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.830
_diffrn_reflns_theta_min         2.600
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7050
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1400 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.9458.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0501P)^2^+0.8414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1417
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3907
_reflns_number_total             4495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01225b2.cif
_cod_data_source_block           raj
_cod_depositor_comments          'Adding full bibliography for 7160832.cif.'
_cod_database_code               7160832
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.991
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C1A(H1A), C1B(H1B), C1C(H1C), C1D(H1D), C1F(H1F)
2.b Idealised Me refined as rotating group:
 C1E(H1EA,H1EB,H1EC), C1G(H1GA,H1GB,H1GC)
;
_shelx_res_checksum              16548
_olex2_submission_original_sample_id UJ(O)_RKS_30
_olex2_submission_special_instructions 'No special instructions were received'