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#$Date: 2024-12-05 22:10:01 +0200 (Thu, 05 Dec 2024) $
#$Revision: 296232 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160282.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_7160282
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                96.72(2)
_cell_angle_beta                 102.06(2)
_cell_angle_gamma                99.58(2)
_cell_formula_units_Z            2
_cell_length_a                   7.904(6)
_cell_length_b                   10.247(7)
_cell_length_c                   11.533(8)
_cell_measurement_reflns_used    2509
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.85
_cell_measurement_theta_min      2.52
_cell_volume                     889.5(11)
_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 Apex Kappa-II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1212
_diffrn_reflns_av_unetI/netI     0.1069
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20493
_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         27.490
_diffrn_reflns_theta_min         3.039
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1244
_refine_ls_R_factor_gt           0.0704
_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)+(0.0511P)²+0.0317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1397
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2451
_reflns_number_total             4075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01023j2.cif
_cod_data_source_block           is_av140f1
_cod_database_code               7160282
_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   0.947
_shelx_estimated_absorpt_t_max   0.992
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
N1 N 0.7438(3) 0.4765(2) 0.3625(2) 0.0225(5) Uani 1 1 d . . . . .
S1 S 0.36828(10) 0.13258(8) 0.64074(7) 0.0242(2) Uani 1 1 d . . . . .
C1 C 0.1735(4) 0.1604(3) 0.5558(2) 0.0238(7) Uani 1 1 d . . . . .
H1 H 0.0605 0.1268 0.5685 0.029 Uiso 1 1 calc R U . . .
C2 C 0.1986(4) 0.2348(3) 0.4695(2) 0.0204(6) Uani 1 1 d . . . . .
H2 H 0.1053 0.2593 0.4153 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3824(4) 0.2734(3) 0.4684(2) 0.0182(6) Uani 1 1 d . . . . .
C4 C 0.4631(4) 0.3561(3) 0.3936(2) 0.0185(6) Uani 1 1 d . . . . .
C5 C 0.3701(4) 0.4001(3) 0.2897(2) 0.0210(6) Uani 1 1 d . . . . .
C6 C 0.4662(4) 0.4820(3) 0.2299(3) 0.0250(7) Uani 1 1 d . . . . .
H6 H 0.4077 0.5135 0.1611 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6503(4) 0.5187(3) 0.2703(3) 0.0264(7) Uani 1 1 d . . . . .
H7 H 0.7119 0.5778 0.2286 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6515(3) 0.3951(3) 0.4234(2) 0.0189(6) Uani 1 1 d . . . . .
C9 C 0.7549(4) 0.3470(3) 0.5201(2) 0.0207(6) Uani 1 1 d . . . . .
H9 H 0.8795 0.3756 0.5392 0.025 Uiso 1 1 calc R U . . .
C10 C 0.6806(3) 0.2609(3) 0.5864(2) 0.0184(6) Uani 1 1 d . . . . .
C11 C 0.4921(4) 0.2258(3) 0.5591(2) 0.0204(6) Uani 1 1 d . . . . .
C12 C 0.1825(4) 0.3578(3) 0.2407(2) 0.0214(6) Uani 1 1 d . . . . .
C13 C 0.0293(4) 0.3209(3) 0.1927(2) 0.0226(6) Uani 1 1 d . . . . .
C14 C -0.1564(4) 0.2701(3) 0.1427(2) 0.0216(6) Uani 1 1 d . . . . .
C15 C -0.2510(4) 0.1803(3) 0.1999(3) 0.0260(7) Uani 1 1 d . . . . .
H15 H -0.1923 0.1536 0.2712 0.031 Uiso 1 1 calc R U . . .
C16 C -0.4287(4) 0.1301(3) 0.1534(3) 0.0356(8) Uani 1 1 d . . . . .
H16 H -0.4919 0.0693 0.1928 0.043 Uiso 1 1 calc R U . . .
C17 C -0.5149(4) 0.1685(3) 0.0495(3) 0.0411(9) Uani 1 1 d . . . . .
H17 H -0.6375 0.1345 0.0181 0.049 Uiso 1 1 calc R U . . .
C18 C -0.4235(4) 0.2559(3) -0.0087(3) 0.0360(8) Uani 1 1 d . . . . .
H18 H -0.4829 0.2804 -0.0809 0.043 Uiso 1 1 calc R U . . .
C19 C -0.2459(4) 0.3079(3) 0.0374(3) 0.0281(7) Uani 1 1 d . . . . .
H19 H -0.1843 0.3695 -0.0023 0.034 Uiso 1 1 calc R U . . .
C20 C 0.7917(3) 0.2076(3) 0.6848(2) 0.0200(6) Uani 1 1 d . . . . .
C21 C 0.9320(4) 0.2931(3) 0.7678(2) 0.0234(7) Uani 1 1 d . . . . .
H21 H 0.9563 0.3858 0.7625 0.028 Uiso 1 1 calc R U . . .
C22 C 1.0357(4) 0.2435(3) 0.8577(3) 0.0276(7) Uani 1 1 d . . . . .
H22 H 1.1307 0.3023 0.9140 0.033 Uiso 1 1 calc R U . . .
C23 C 1.0013(4) 0.1079(3) 0.8658(3) 0.0313(8) Uani 1 1 d . . . . .
H23 H 1.0721 0.0743 0.9282 0.038 Uiso 1 1 calc R U . . .
C24 C 0.8646(4) 0.0217(3) 0.7835(3) 0.0289(7) Uani 1 1 d . . . . .
H24 H 0.8425 -0.0713 0.7885 0.035 Uiso 1 1 calc R U . . .
C25 C 0.7595(4) 0.0712(3) 0.6933(3) 0.0247(7) Uani 1 1 d . . . . .
H25 H 0.6651 0.0118 0.6370 0.030 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
C7 N1 C8 116.7(2) . . ?
C1 S1 C11 91.40(14) . . ?
C2 C1 S1 113.1(2) . . ?
C2 C1 H1 123.5 . . ?
S1 C1 H1 123.5 . . ?
C1 C2 C3 112.8(3) . . ?
C1 C2 H2 123.6 . . ?
C3 C2 H2 123.6 . . ?
C11 C3 C2 111.8(2) . . ?
C11 C3 C4 118.5(2) . . ?
C2 C3 C4 129.6(3) . . ?
C5 C4 C8 116.8(2) . . ?
C5 C4 C3 125.2(2) . . ?
C8 C4 C3 117.9(2) . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 C12 118.2(3) . . ?
C4 C5 C12 123.5(2) . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
N1 C7 C6 124.4(3) . . ?
N1 C7 H7 117.8 . . ?
C6 C7 H7 117.8 . . ?
N1 C8 C9 115.8(2) . . ?
N1 C8 C4 123.8(2) . . ?
C9 C8 C4 120.4(2) . . ?
C10 C9 C8 122.3(3) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C11 117.1(2) . . ?
C9 C10 C20 121.5(2) . . ?
C11 C10 C20 121.3(2) . . ?
C3 C11 C10 123.5(2) . . ?
C3 C11 S1 111.0(2) . . ?
C10 C11 S1 125.3(2) . . ?
C13 C12 C5 175.7(3) . . ?
C12 C13 C14 175.3(3) . . ?
C15 C14 C19 118.7(3) . . ?
C15 C14 C13 119.6(2) . . ?
C19 C14 C13 121.7(3) . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.0(3) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.1(3) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
C21 C20 C25 118.9(3) . . ?
C21 C20 C10 120.5(3) . . ?
C25 C20 C10 120.6(2) . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.1(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.8(3) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C20 120.5(3) . . ?
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
N1 C7 1.322(4) . ?
N1 C8 1.367(3) . ?
S1 C1 1.730(3) . ?
S1 C11 1.744(3) . ?
C1 C2 1.349(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.444(4) . ?
C2 H2 0.9500 . ?
C3 C11 1.401(4) . ?
C3 C4 1.446(4) . ?
C4 C5 1.431(4) . ?
C4 C8 1.432(4) . ?
C5 C6 1.378(4) . ?
C5 C12 1.444(4) . ?
C6 C7 1.404(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.427(4) . ?
C9 C10 1.372(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.431(4) . ?
C10 C20 1.498(4) . ?
C12 C13 1.198(4) . ?
C13 C14 1.442(4) . ?
C14 C15 1.399(4) . ?
C14 C19 1.403(4) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.396(4) . ?
C20 C25 1.397(4) . ?
C21 C22 1.383(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(4) . ?
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 0.5(2) . . . . ?
S1 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C11 -1.0(3) . . . . ?
C1 C2 C3 C4 -177.6(3) . . . . ?
C11 C3 C4 C5 172.9(3) . . . . ?
C2 C3 C4 C5 -10.7(5) . . . . ?
C11 C3 C4 C8 -5.7(4) . . . . ?
C2 C3 C4 C8 170.7(3) . . . . ?
C8 C4 C5 C6 -3.3(4) . . . . ?
C3 C4 C5 C6 178.2(3) . . . . ?
C8 C4 C5 C12 173.3(3) . . . . ?
C3 C4 C5 C12 -5.3(4) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C12 C5 C6 C7 -176.1(3) . . . . ?
C8 N1 C7 C6 -2.1(4) . . . . ?
C5 C6 C7 N1 2.3(5) . . . . ?
C7 N1 C8 C9 178.0(2) . . . . ?
C7 N1 C8 C4 -0.8(4) . . . . ?
C5 C4 C8 N1 3.5(4) . . . . ?
C3 C4 C8 N1 -177.8(2) . . . . ?
C5 C4 C8 C9 -175.3(2) . . . . ?
C3 C4 C8 C9 3.4(4) . . . . ?
N1 C8 C9 C10 -177.7(3) . . . . ?
C4 C8 C9 C10 1.2(4) . . . . ?
C8 C9 C10 C11 -3.3(4) . . . . ?
C8 C9 C10 C20 177.8(2) . . . . ?
C2 C3 C11 C10 -173.3(2) . . . . ?
C4 C3 C11 C10 3.7(4) . . . . ?
C2 C3 C11 S1 1.3(3) . . . . ?
C4 C3 C11 S1 178.4(2) . . . . ?
C9 C10 C11 C3 0.8(4) . . . . ?
C20 C10 C11 C3 179.7(2) . . . . ?
C9 C10 C11 S1 -173.1(2) . . . . ?
C20 C10 C11 S1 5.9(4) . . . . ?
C1 S1 C11 C3 -1.1(2) . . . . ?
C1 S1 C11 C10 173.5(2) . . . . ?
C19 C14 C15 C16 0.0(4) . . . . ?
C13 C14 C15 C16 -179.8(3) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C15 C16 C17 C18 0.6(5) . . . . ?
C16 C17 C18 C19 -1.2(5) . . . . ?
C17 C18 C19 C14 1.2(5) . . . . ?
C15 C14 C19 C18 -0.6(4) . . . . ?
C13 C14 C19 C18 179.2(3) . . . . ?
C9 C10 C20 C21 45.3(4) . . . . ?
C11 C10 C20 C21 -133.6(3) . . . . ?
C9 C10 C20 C25 -133.1(3) . . . . ?
C11 C10 C20 C25 48.0(4) . . . . ?
C25 C20 C21 C22 -0.8(4) . . . . ?
C10 C20 C21 C22 -179.2(3) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C21 C22 C23 C24 0.7(5) . . . . ?
C22 C23 C24 C25 -1.0(5) . . . . ?
C23 C24 C25 C20 0.3(4) . . . . ?
C21 C20 C25 C24 0.5(4) . . . . ?
C10 C20 C25 C24 178.9(3) . . . . ?
