Synthesis and properties of thienonaphtho[<i>bc</i>]pyridines and thienonaphtho[<i>bc</i>]quinolines.
Vardanyan, Arpine; Polkaehn, Jonas; Bauder, Marie-Louis; Villinger, Alexander; Ehlers, Peter; Langer, Peter; Organic & biomolecular chemistry 22 (2024) 8631–8648; doi:10.1039/d4ob01023j

data_7160283
_publ_section_title
;
 Synthesis and properties of thienonaphtho[<i>bc</i>]pyridines and
 thienonaphtho[<i>bc</i>]quinolines.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8631
_journal_page_last               8648
_journal_paper_doi               10.1039/d4ob01023j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C29 H17 N S'
_chemical_formula_sum            'C29 H17 N S'
_chemical_formula_weight         411.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-06-18 deposited with the CCDC.	2024-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                105.953(2)
_cell_angle_beta                 95.907(2)
_cell_angle_gamma                108.672(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0321(4)
_cell_length_b                   10.3560(5)
_cell_length_c                   13.1722(6)
_cell_measurement_reflns_used    9861
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.07
_cell_measurement_theta_min      2.27
_cell_volume                     975.86(8)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            53873
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.738
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.7108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5693
_refine_ls_number_restraints     193
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.3554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4636
_reflns_number_total             5693
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01023j2.cif
_cod_data_source_block           is_jp226ph
_cod_database_code               7160283
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              707