#------------------------------------------------------------------------------
#$Date: 2024-12-05 22:10:01 +0200 (Thu, 05 Dec 2024) $
#$Revision: 296232 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160281.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7160281
loop_
_publ_author_name
'Vardanyan, Arpine'
'Polkaehn, Jonas'
'Bauder, Marie-Louis'
'Villinger, Alexander'
'Ehlers, Peter'
'Langer, Peter'
_publ_section_title
;
 Synthesis and properties of thienonaphtho[bc]pyridines and
 thienonaphtho[bc]quinolines.
;
_journal_issue                   43
_journal_name_full               'Organic & 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         'C25 H15 N S'
_chemical_formula_sum            'C25 H15 N S'
_chemical_formula_weight         361.44
_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                96.301(4)
_cell_angle_beta                 101.547(3)
_cell_angle_gamma                101.238(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0985(9)
_cell_length_b                   10.3014(12)
_cell_length_c                   11.0803(12)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      32.45
_cell_measurement_theta_min      2.63
_cell_volume                     877.60(17)
_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 0.998
_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  0.0668
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36309
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_min         2.563
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         5119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0516
_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/[σ²(Fo²)+(0.0330P)²+1.0990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1255
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3778
_reflns_number_total             5119
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01023j2.cif
_cod_data_source_block           av_av140f4b
_cod_database_code               7160281
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.910
_shelx_estimated_absorpt_t_max   0.996
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.63272(6) 0.87344(5) 0.34413(4) 0.02200(12) Uani 1 1 d . . . . .
N1 N 0.5532(2) 0.51633(16) 0.77104(15) 0.0217(3) Uani 1 1 d . . . . .
C1 C 0.8233(2) 0.84981(19) 0.42999(17) 0.0216(4) Uani 1 1 d . . . . .
H1 H 0.9335 0.8848 0.4148 0.026 Uiso 1 1 calc R U . . .
C2 C 0.7998(2) 0.77603(18) 0.52171(17) 0.0194(4) Uani 1 1 d . . . . .
H2 H 0.8916 0.7539 0.5777 0.023 Uiso 1 1 calc R U . . .
C3 C 0.6213(2) 0.73490(17) 0.52509(16) 0.0158(3) Uani 1 1 d . . . . .
C4 C 0.5420(2) 0.65134(17) 0.60338(16) 0.0156(3) Uani 1 1 d . . . . .
C5 C 0.6320(2) 0.60019(17) 0.70582(17) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.3789(2) 0.48178(19) 0.74117(18) 0.0224(4) Uani 1 1 d . . . . .
H6 H 0.3226 0.4210 0.7865 0.027 Uiso 1 1 calc R U . . .
C7 C 0.2792(2) 0.52932(18) 0.64954(17) 0.0198(4) Uani 1 1 d . . . . .
H7 H 0.1567 0.5044 0.6343 0.024 Uiso 1 1 calc R U . . .
C8 C 0.3591(2) 0.61559(17) 0.57763(16) 0.0160(3) Uani 1 1 d . . . . .
C9 C 0.2576(2) 0.66650(18) 0.48152(16) 0.0176(3) Uani 1 1 d . . . . .
H9 H 0.1352 0.6422 0.4677 0.021 Uiso 1 1 calc R U . . .
C10 C 0.3297(2) 0.74893(17) 0.40850(16) 0.0166(3) Uani 1 1 d . . . . .
C11 C 0.5138(2) 0.78142(17) 0.43213(16) 0.0167(3) Uani 1 1 d . . . . .
C12 C 0.8156(2) 0.63955(18) 0.75171(17) 0.0200(4) Uani 1 1 d . . . . .
C13 C 0.9665(2) 0.67520(18) 0.80126(17) 0.0197(4) Uani 1 1 d . . . . .
C14 C 1.1469(2) 0.71876(18) 0.85851(17) 0.0188(3) Uani 1 1 d . . . . .
C15 C 1.2505(2) 0.82183(19) 0.81768(18) 0.0235(4) Uani 1 1 d . . . . .
H15 H 1.2012 0.8641 0.7519 0.028 Uiso 1 1 calc R U . . .
C16 C 1.4246(3) 0.8624(2) 0.8728(2) 0.0304(5) Uani 1 1 d . . . . .
H16 H 1.4951 0.9322 0.8444 0.036 Uiso 1 1 calc R U . . .
C17 C 1.4967(3) 0.8016(2) 0.9692(2) 0.0342(5) Uani 1 1 d . . . . .
H17 H 1.6166 0.8300 1.0068 0.041 Uiso 1 1 calc R U . . .
C18 C 1.3957(3) 0.7001(2) 1.01106(19) 0.0294(4) Uani 1 1 d . . . . .
H18 H 1.4460 0.6593 1.0777 0.035 Uiso 1 1 calc R U . . .
C19 C 1.2215(2) 0.65766(19) 0.95606(17) 0.0219(4) Uani 1 1 d . . . . .
H19 H 1.1523 0.5871 0.9844 0.026 Uiso 1 1 calc R U . . .
C20 C 0.2187(2) 0.79916(18) 0.30927(16) 0.0170(3) Uani 1 1 d . . . . .
C21 C 0.0770(2) 0.71098(19) 0.22798(17) 0.0196(4) Uani 1 1 d . . . . .
H21 H 0.0551 0.6183 0.2344 0.023 Uiso 1 1 calc R U . . .
C22 C -0.0320(2) 0.7578(2) 0.13808(17) 0.0224(4) Uani 1 1 d . . . . .
H22 H -0.1279 0.6971 0.0833 0.027 Uiso 1 1 calc R U . . .
C23 C -0.0015(2) 0.8926(2) 0.12784(18) 0.0243(4) Uani 1 1 d . . . . .
H23 H -0.0765 0.9245 0.0663 0.029 Uiso 1 1 calc R U . . .
C24 C 0.1392(3) 0.9809(2) 0.20797(19) 0.0247(4) Uani 1 1 d . . . . .
H24 H 0.1605 1.0735 0.2011 0.030 Uiso 1 1 calc R U . . .
C25 C 0.2486(2) 0.93474(19) 0.29795(18) 0.0220(4) Uani 1 1 d . . . . .
H25 H 0.3445 0.9959 0.3523 0.026 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C11 91.56(9) . . ?
C5 N1 C6 117.99(16) . . ?
C2 C1 S1 112.87(14) . . ?
C2 C1 H1 123.6 . . ?
S1 C1 H1 123.6 . . ?
C1 C2 C3 112.75(16) . . ?
C1 C2 H2 123.6 . . ?
C3 C2 H2 123.6 . . ?
C11 C3 C2 111.56(15) . . ?
C11 C3 C4 118.34(15) . . ?
C2 C3 C4 130.03(16) . . ?
C8 C4 C5 116.40(15) . . ?
C8 C4 C3 117.88(15) . . ?
C5 C4 C3 125.72(16) . . ?
N1 C5 C4 123.61(16) . . ?
N1 C5 C12 113.57(16) . . ?
C4 C5 C12 122.76(16) . . ?
N1 C6 C7 123.61(17) . . ?
N1 C6 H6 118.2 . . ?
C7 C6 H6 118.2 . . ?
C6 C7 C8 119.50(17) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C4 118.75(16) . . ?
C7 C8 C9 120.48(16) . . ?
C4 C8 C9 120.77(15) . . ?
C10 C9 C8 122.40(16) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C11 116.68(15) . . ?
C9 C10 C20 120.48(15) . . ?
C11 C10 C20 122.83(15) . . ?
C3 C11 C10 123.85(15) . . ?
C3 C11 S1 111.26(13) . . ?
C10 C11 S1 124.77(13) . . ?
C13 C12 C5 173.7(2) . . ?
C12 C13 C14 179.0(2) . . ?
C15 C14 C19 119.27(17) . . ?
C15 C14 C13 120.51(16) . . ?
C19 C14 C13 120.22(17) . . ?
C16 C15 C14 120.10(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.12(19) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 120.45(19) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.05(19) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 120.01(18) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C25 C20 C21 118.74(17) . . ?
C25 C20 C10 121.21(16) . . ?
C21 C20 C10 120.00(16) . . ?
C22 C21 C20 120.51(17) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 120.30(18) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.62(18) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C25 C24 C23 120.36(18) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C20 120.46(18) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7194(19) . ?
S1 C11 1.7318(17) . ?
N1 C5 1.335(2) . ?
N1 C6 1.349(2) . ?
C1 C2 1.356(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.434(2) . ?
C2 H2 0.9500 . ?
C3 C11 1.400(2) . ?
C3 C4 1.441(2) . ?
C4 C8 1.417(2) . ?
C4 C5 1.431(2) . ?
C5 C12 1.433(2) . ?
C6 C7 1.363(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.407(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.423(2) . ?
C9 C10 1.365(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.427(2) . ?
C10 C20 1.481(2) . ?
C12 C13 1.201(3) . ?
C13 C14 1.431(3) . ?
C14 C15 1.395(3) . ?
C14 C19 1.402(2) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.394(3) . ?
C20 C21 1.398(2) . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 S1 C1 C2 -0.17(16) . . . . ?
S1 C1 C2 C3 0.2(2) . . . . ?
C1 C2 C3 C11 0.0(2) . . . . ?
C1 C2 C3 C4 176.77(18) . . . . ?
C11 C3 C4 C8 3.1(2) . . . . ?
C2 C3 C4 C8 -173.58(17) . . . . ?
C11 C3 C4 C5 -177.09(16) . . . . ?
C2 C3 C4 C5 6.3(3) . . . . ?
C6 N1 C5 C4 -2.4(3) . . . . ?
C6 N1 C5 C12 174.89(16) . . . . ?
C8 C4 C5 N1 4.1(3) . . . . ?
C3 C4 C5 N1 -175.72(17) . . . . ?
C8 C4 C5 C12 -172.88(16) . . . . ?
C3 C4 C5 C12 7.3(3) . . . . ?
C5 N1 C6 C7 -1.0(3) . . . . ?
N1 C6 C7 C8 2.4(3) . . . . ?
C6 C7 C8 C4 -0.4(3) . . . . ?
C6 C7 C8 C9 -179.97(17) . . . . ?
C5 C4 C8 C7 -2.6(2) . . . . ?
C3 C4 C8 C7 177.27(16) . . . . ?
C5 C4 C8 C9 176.98(16) . . . . ?
C3 C4 C8 C9 -3.2(2) . . . . ?
C7 C8 C9 C10 -179.10(17) . . . . ?
C4 C8 C9 C10 1.3(3) . . . . ?
C8 C9 C10 C11 0.6(3) . . . . ?
C8 C9 C10 C20 179.82(16) . . . . ?
C2 C3 C11 C10 175.98(16) . . . . ?
C4 C3 C11 C10 -1.2(3) . . . . ?
C2 C3 C11 S1 -0.08(19) . . . . ?
C4 C3 C11 S1 -177.32(13) . . . . ?
C9 C10 C11 C3 -0.6(3) . . . . ?
C20 C10 C11 C3 -179.83(16) . . . . ?
C9 C10 C11 S1 174.93(14) . . . . ?
C20 C10 C11 S1 -4.3(2) . . . . ?
C1 S1 C11 C3 0.14(14) . . . . ?
C1 S1 C11 C10 -175.88(16) . . . . ?
C19 C14 C15 C16 0.2(3) . . . . ?
C13 C14 C15 C16 -179.46(19) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C14 -0.7(3) . . . . ?
C15 C14 C19 C18 0.3(3) . . . . ?
C13 C14 C19 C18 180.00(18) . . . . ?
C9 C10 C20 C25 130.92(19) . . . . ?
C11 C10 C20 C25 -49.9(2) . . . . ?
C9 C10 C20 C21 -46.5(2) . . . . ?
C11 C10 C20 C21 132.71(18) . . . . ?
C25 C20 C21 C22 -0.2(3) . . . . ?
C10 C20 C21 C22 177.30(16) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C20 0.0(3) . . . . ?
C21 C20 C25 C24 0.2(3) . . . . ?
C10 C20 C25 C24 -177.24(17) . . . . ?
