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_7251742
_publ_section_title
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 A regioselective sustainable neat approach to
 naphtho[2,3-<i>b</i>]thiophene-4,9-dione: detailed mechanistic study and
 DFT analysis.
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_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_sum            'C21 H15 N O4 S'
_chemical_formula_weight         377.40
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2cyqwy
_audit_creation_method           SHELXL-97
_audit_update_record
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2022-08-24 deposited with the CCDC.	2026-01-23 downloaded from the CCDC.
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_cell_angle_alpha                90.00
_cell_angle_beta                 93.995(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5042(4)
_cell_length_b                   11.6247(4)
_cell_length_c                   14.2377(6)
_cell_measurement_reflns_used    794
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     1734.32(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29404
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.9295
_exptl_absorpt_correction_T_min  0.7557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            RED
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.0190(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0559P)^2^+0.4823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0922
_reflns_number_gt                2765
_reflns_number_total             3055
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5ra08362a2.cif
_cod_data_source_block           t7
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'MONOCLINIC' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
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_cod_original_sg_symbol_H-M      P21/C
_cod_database_code               7251742