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#$Date: 2025-03-04 22:19:33 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298272 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/76/7717625.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_7717625
loop_
_publ_author_name
'Angarkhe, Priyanka R.'
'Sahoo, Satyajit'
'Singhdeo, Simran'
'Shankar, Sr, Kripa'
'Upadhyay, Manav'
'Mahiya, Kuldeep'
'Tripathy, Jagnyaseni'
'Behera, Rakesh K.'
'Mohapatra, Swagat K.'
_publ_section_title
;
 Structural and optical studies of fluoride ion binding using
 N-heteroaromatic ligands.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2069
_journal_page_last               2077
_journal_paper_doi               10.1039/d4dt02857k
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C16 H10 N2 O S'
_chemical_formula_sum            'C16 H10 N2 O S'
_chemical_formula_weight         278.32
_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-2019/1
_audit_update_record
;
2024-10-30 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                99.948(5)
_cell_angle_beta                 108.024(4)
_cell_angle_gamma                96.408(5)
_cell_formula_units_Z            2
_cell_length_a                   8.0639(10)
_cell_length_b                   8.1559(11)
_cell_length_c                   10.4359(14)
_cell_measurement_reflns_used    1768
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      0.956
_cell_measurement_theta_min      0.946
_cell_volume                     632.80(15)
_computing_cell_refinement       'Bruker SHELXL'
_computing_data_collection       'Bruker APEX4'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      299(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 quest photon detector'
_diffrn_measurement_method       'Omega and Phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0891
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20160
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         2.698
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.251
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       Rod
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0496
_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)+(0.0508P)²+0.1872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1437
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1768
_reflns_number_total             2915
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02857k2.cif
_cod_data_source_block           bt_tbaf_0m_a
_cod_depositor_comments
'Adding full bibliography for 7717624--7717629.cif.'
_cod_original_cell_volume        632.80(14)
_cod_database_code               7717625
_shelx_shelxl_version_number     2019/1
_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.
;
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 -0.01593(9) 0.48299(9) 0.18891(7) 0.0617(3) Uani 1 1 d . . . . .
O1 O 0.7836(2) 0.2992(2) 0.4119(2) 0.0651(5) Uani 1 1 d . . . . .
H1 H 0.873592 0.370027 0.453179 0.098 Uiso 1 1 calc R U . . .
N3 N 0.8340(3) 0.6415(2) 0.4796(2) 0.0492(5) Uani 1 1 d . . . . .
N1 N 0.1838(3) 0.7635(3) 0.2082(2) 0.0569(6) Uani 1 1 d . . . . .
C13 C 0.5207(3) 0.6390(3) 0.3576(2) 0.0443(5) Uani 1 1 d . . . . .
C8 C 0.3525(3) 0.5383(3) 0.2738(2) 0.0466(6) Uani 1 1 d . . . . .
C12 C 0.6675(3) 0.5576(3) 0.4027(2) 0.0443(5) Uani 1 1 d . . . . .
C16 C 0.8566(3) 0.8077(3) 0.5145(3) 0.0532(6) Uani 1 1 d . . . . .
H16 H 0.969586 0.866818 0.567171 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6456(3) 0.3776(3) 0.3663(3) 0.0490(6) Uani 1 1 d . . . . .
C14 C 0.5539(3) 0.8170(3) 0.3992(3) 0.0500(6) Uani 1 1 d . . . . .
H14 H 0.462298 0.877516 0.373738 0.060 Uiso 1 1 calc R U . . .
C15 C 0.7207(3) 0.8998(3) 0.4768(3) 0.0554(6) Uani 1 1 d . . . . .
H15 H 0.743607 1.017108 0.504451 0.066 Uiso 1 1 calc R U . . .
C2 C 0.1906(3) 0.6106(3) 0.2252(2) 0.0493(6) Uani 1 1 d . . . . .
C1 C 0.0095(3) 0.7910(3) 0.1659(3) 0.0553(7) Uani 1 1 d . . . . .
C9 C 0.3409(3) 0.3655(3) 0.2402(3) 0.0545(6) Uani 1 1 d . . . . .
H9 H 0.232279 0.299617 0.184576 0.065 Uiso 1 1 calc R U . . .
C10 C 0.4848(4) 0.2853(3) 0.2859(3) 0.0562(6) Uani 1 1 d . . . . .
H10 H 0.470740 0.168122 0.261354 0.067 Uiso 1 1 calc R U . . .
C3 C -0.1178(3) 0.6509(3) 0.1494(2) 0.0536(6) Uani 1 1 d . . . . .
C5 C -0.3450(4) 0.8149(5) 0.0910(3) 0.0794(10) Uani 1 1 d . . . . .
H5 H -0.463907 0.824903 0.066299 0.095 Uiso 1 1 calc R U . . .
C7 C -0.0436(4) 0.9423(4) 0.1433(3) 0.0740(9) Uani 1 1 d . . . . .
H7 H 0.039789 1.036306 0.153315 0.089 Uiso 1 1 calc R U . . .
C4 C -0.2968(4) 0.6622(4) 0.1117(3) 0.0665(8) Uani 1 1 d . . . . .
H4 H -0.381641 0.569001 0.100886 0.080 Uiso 1 1 calc R U . . .
C6 C -0.2203(5) 0.9524(5) 0.1061(3) 0.0826(9) Uani 1 1 d . . . . .
H6 H -0.256058 1.053915 0.090891 0.099 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'
O O 0.0106 0.0060 '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
C3 S1 C2 89.32(12) . . ?
C11 O1 H1 109.5 . . ?
C16 N3 C12 117.2(2) . . ?
C2 N1 C1 111.1(2) . . ?
C14 C13 C12 116.2(2) . . ?
C14 C13 C8 124.9(2) . . ?
C12 C13 C8 118.9(2) . . ?
C9 C8 C13 118.3(2) . . ?
C9 C8 C2 118.7(2) . . ?
C13 C8 C2 123.0(2) . . ?
N3 C12 C13 123.7(2) . . ?
N3 C12 C11 116.3(2) . . ?
C13 C12 C11 120.0(2) . . ?
N3 C16 C15 123.6(2) . . ?
N3 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
O1 C11 C10 119.9(2) . . ?
O1 C11 C12 120.2(2) . . ?
C10 C11 C12 119.9(2) . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
N1 C2 C8 126.3(2) . . ?
N1 C2 S1 115.03(19) . . ?
C8 C2 S1 118.67(18) . . ?
C7 C1 N1 125.8(3) . . ?
C7 C1 C3 119.4(2) . . ?
N1 C1 C3 114.7(2) . . ?
C8 C9 C10 122.8(2) . . ?
C8 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C4 C3 C1 120.8(3) . . ?
C4 C3 S1 129.4(2) . . ?
C1 C3 S1 109.80(19) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C6 C7 C1 119.5(3) . . ?
C6 C7 H7 120.3 . . ?
C1 C7 H7 120.3 . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
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 C3 1.720(3) . ?
S1 C2 1.757(2) . ?
O1 C11 1.346(3) . ?
O1 H1 0.8200 . ?
N3 C16 1.318(3) . ?
N3 C12 1.362(3) . ?
N1 C2 1.294(3) . ?
N1 C1 1.393(3) . ?
C13 C14 1.411(3) . ?
C13 C12 1.416(3) . ?
C13 C8 1.431(3) . ?
C8 C9 1.378(3) . ?
C8 C2 1.475(3) . ?
C12 C11 1.427(3) . ?
C16 C15 1.393(3) . ?
C16 H16 0.9300 . ?
C11 C10 1.358(4) . ?
C14 C15 1.362(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C1 C7 1.385(4) . ?
C1 C3 1.396(4) . ?
C9 C10 1.392(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C3 C4 1.391(4) . ?
C5 C6 1.372(5) . ?
C5 C4 1.378(4) . ?
C5 H5 0.9300 . ?
C7 C6 1.372(4) . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
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
C14 C13 C8 C9 179.3(2) . . . . ?
C12 C13 C8 C9 -0.1(3) . . . . ?
C14 C13 C8 C2 -2.5(4) . . . . ?
C12 C13 C8 C2 178.1(2) . . . . ?
C16 N3 C12 C13 0.8(3) . . . . ?
C16 N3 C12 C11 -179.8(2) . . . . ?
C14 C13 C12 N3 -1.2(3) . . . . ?
C8 C13 C12 N3 178.2(2) . . . . ?
C14 C13 C12 C11 179.5(2) . . . . ?
C8 C13 C12 C11 -1.1(3) . . . . ?
C12 N3 C16 C15 -0.1(4) . . . . ?
N3 C12 C11 O1 2.4(3) . . . . ?
C13 C12 C11 O1 -178.2(2) . . . . ?
N3 C12 C11 C10 -177.9(2) . . . . ?
C13 C12 C11 C10 1.5(3) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C8 C13 C14 C15 -178.6(2) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
N3 C16 C15 C14 -0.3(4) . . . . ?
C1 N1 C2 C8 -177.8(2) . . . . ?
C1 N1 C2 S1 0.9(3) . . . . ?
C9 C8 C2 N1 -156.7(2) . . . . ?
C13 C8 C2 N1 25.1(4) . . . . ?
C9 C8 C2 S1 24.7(3) . . . . ?
C13 C8 C2 S1 -153.53(19) . . . . ?
C3 S1 C2 N1 -0.5(2) . . . . ?
C3 S1 C2 C8 178.23(19) . . . . ?
C2 N1 C1 C7 177.6(3) . . . . ?
C2 N1 C1 C3 -0.8(3) . . . . ?
C13 C8 C9 C10 0.9(4) . . . . ?
C2 C8 C9 C10 -177.4(2) . . . . ?
O1 C11 C10 C9 179.0(2) . . . . ?
C12 C11 C10 C9 -0.7(4) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C7 C1 C3 C4 -0.6(4) . . . . ?
N1 C1 C3 C4 178.0(2) . . . . ?
C7 C1 C3 S1 -178.1(2) . . . . ?
N1 C1 C3 S1 0.5(3) . . . . ?
C2 S1 C3 C4 -177.2(2) . . . . ?
C2 S1 C3 C1 0.02(19) . . . . ?
N1 C1 C7 C6 -177.9(3) . . . . ?
C3 C1 C7 C6 0.5(4) . . . . ?
C6 C5 C4 C3 0.4(4) . . . . ?
C1 C3 C4 C5 0.1(4) . . . . ?
S1 C3 C4 C5 177.1(2) . . . . ?
C1 C7 C6 C5 0.0(5) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
