A regioselective sustainable neat approach to naphtho[2,3-<i>b</i>]thiophene-4,9-dione: detailed mechanistic study and DFT analysis.
Manik, Soumen K.; Ali, Sk Asraf; Sepay, Nayim; Deb, Aniruddha; Shit, Manik; Barik, Paritosh; Rath, Jyotirmoy; Maity, Kankan K.; Pal, Sudhir C.; Samanta, Shubhankar; Hazra, Nirmal K.; RSC advances 16 (2026) 6090–6105; doi:10.1039/d5ra08362a

data_7251745
_publ_section_title
;
 A regioselective sustainable neat approach to
 naphtho[2,3-<i>b</i>]thiophene-4,9-dione: detailed mechanistic study and
 DFT analysis.
;
_journal_issue                   7
_journal_name_full               'RSC advances'
_journal_page_first              6090
_journal_page_last               6105
_journal_paper_doi               10.1039/d5ra08362a
_journal_volume                  16
_journal_year                    2026
_chemical_formula_moiety         'C16 H13 Cl O5'
_chemical_formula_sum            'C16 H13 Cl O5'
_chemical_formula_weight         320.71
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2023-04-20 deposited with the CCDC.	2026-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.648(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4440(6)
_cell_length_b                   10.3940(5)
_cell_length_c                   15.2628(9)
_cell_measurement_reflns_used    9823
_cell_measurement_temperature    104(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.39
_cell_volume                     1442.68(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      104(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.785
_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  0.1008
_diffrn_reflns_av_unetI/netI     0.1214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.785
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            46215
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.798
_diffrn_reflns_theta_min         2.294
_exptl_absorpt_coefficient_mu    0.286
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         5679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1422
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+0.6571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1303
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3347
_reflns_number_total             5679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra08362a2.cif
_cod_data_source_block           ARD_CD_85B_autored
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7251745
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              45234