From benzofuro-, benzothieno- and 10-methylindolo-[2,3-b]-fused benzothiopyrano[4,3,2-de]quinolines to the corresponding benzothiopyrano[4,3,2-de]1,8-naphthyridines: synthesis and properties of these hexacyclic heteroaromatic compounds
Mast, Nicolas; Erb, William; Nauton, Lionel; Moreau, Pascale; Mongin, Olivier; Roisnel, Thierry; Macaigne, Margaux; Robert, Thomas; Bach, Stéphane; Picot, Laurent; Thiéry, Valérie; Hurvois, Jean-Pierre; Mongin, Florence; New Journal of Chemistry 47 (2023) 258–283; doi:10.1039/D2NJ04567B

data_7062121
_publ_section_title
;
 From benzofuro-, benzothieno- and 10-methylindolo-[2,3-b]-fused
 benzothiopyrano[4,3,2-de]quinolines to the corresponding
 benzothiopyrano[4,3,2-de]1,8-naphthyridines: synthesis and properties of
 these hexacyclic heteroaromatic compounds
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              258
_journal_page_last               283
_journal_paper_doi               10.1039/D2NJ04567B
_journal_volume                  47
_journal_year                    2023
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C22 H14 N2 S'
_chemical_formula_sum            'C22 H14 N2 S'
_chemical_formula_weight         338.41
_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
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-09-01 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.043(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.8094(10)
_cell_length_b                   12.1986(9)
_cell_length_c                   19.1371(15)
_cell_measurement_reflns_used    4518
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.2097
_cell_measurement_theta_min      2.2400
_cell_measurement_wavelength     0.710730
_cell_volume                     3183.7(4)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_orient_matrix_UB_11      0.0208013
_diffrn_orient_matrix_UB_12      0.0290491
_diffrn_orient_matrix_UB_13      0.0489202
_diffrn_orient_matrix_UB_21      -0.0595745
_diffrn_orient_matrix_UB_22      0.0477419
_diffrn_orient_matrix_UB_23      -0.0053427
_diffrn_orient_matrix_UB_31      -0.0373477
_diffrn_orient_matrix_UB_32      -0.0599755
_diffrn_orient_matrix_UB_33      0.0194416
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0630
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21613
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_min         2.240
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.055
_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     453
_refine_ls_number_reflns         7274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.5384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1140
_reflns_number_gt                4807
_reflns_number_total             7274
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2nj04567b2.cif
_cod_data_source_block           NM022
_cod_depositor_comments
'Adding full bibliography for 7062120--7062126.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7062121
_shelx_res_checksum              25875