#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/81/4518137.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_4518137
loop_
_publ_author_name
'Shyamsivappan, Selvaraj'
'Saravanan, Arjunan'
'Vandana, Nandakumar'
'Suresh, Thangaraj'
'Suresh, Shanmugam'
'Nandhakumar, Raju'
'Mohan, Palathurai Subramaniam'
_publ_section_title
;
 Novel Quinoline-Based Thiazole Derivatives for Selective Detection of
 Fe³⁺, Fe²⁺, and Cu²⁺ Ions.
;
_journal_issue                   42
_journal_name_full               'ACS omega'
_journal_page_first              27245
_journal_page_last               27253
_journal_paper_doi               10.1021/acsomega.0c03445
_journal_volume                  5
_journal_year                    2020
_chemical_formula_sum            'C16 H13 N5 O2 S'
_chemical_formula_weight         339.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 91.509(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.888(2)
_cell_length_b                   4.7349(8)
_cell_length_c                   23.274(4)
_cell_measurement_reflns_used    2452
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.89
_cell_measurement_theta_min      2.63
_cell_volume                     1529.9(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-2014
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.937
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7655
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.934
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0578
_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)+(0.0786P)²+0.9256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1604
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2029
_reflns_number_total             2599
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao0c03445_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4518136--4518137.cif.'
_cod_original_cell_volume        1529.9(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4518137
_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   0.917
_shelx_estimated_absorpt_t_max   0.962
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.47068(5) 0.61988(17) 0.35766(3) 0.0473(3) Uani 1 1 d . . . . .
C1 C 0.52539(19) 0.8521(6) 0.31095(12) 0.0403(6) Uani 1 1 d . . . . .
O1 O 0.08742(16) -0.5724(5) 0.53264(11) 0.0666(7) Uani 1 1 d . . . . .
N1 N 0.16728(18) -0.5206(6) 0.55409(10) 0.0499(6) Uani 1 1 d . . . . .
N2 N 0.11093(15) -0.2015(5) 0.44988(10) 0.0457(6) Uani 1 1 d . . . . .
H2 H 0.0779 -0.3514 0.4562 0.055 Uiso 1 1 calc R U . . .
C2 C 0.6192(2) 0.9549(7) 0.31355(13) 0.0498(7) Uani 1 1 d . . . . .
H2A H 0.6622 0.8986 0.3427 0.060 Uiso 1 1 calc R U . . .
O2 O 0.19678(19) -0.6436(7) 0.59701(12) 0.0888(9) Uani 1 1 d . . . . .
N4 N 0.28990(17) 0.4805(5) 0.32934(10) 0.0461(6) Uani 1 1 d . . . . .
H4N H 0.2372 0.4698 0.3092 0.055 Uiso 1 1 calc R U . . .
C4 C 0.5825(2) 1.2253(8) 0.22885(15) 0.0608(9) Uani 1 1 d . . . . .
H4 H 0.6022 1.3543 0.2014 0.073 Uiso 1 1 calc R U . . .
N3 N 0.30542(16) 0.3384(5) 0.38006(10) 0.0436(6) Uani 1 1 d . . . . .
C3 C 0.6470(2) 1.1424(7) 0.27180(14) 0.0548(8) Uani 1 1 d . . . . .
H3 H 0.7094 1.2135 0.2726 0.066 Uiso 1 1 calc R U . . .
N5 N 0.36852(15) 0.8077(5) 0.26954(10) 0.0421(6) Uani 1 1 d . . . . .
C5 C 0.4598(2) 0.9304(6) 0.26751(12) 0.0402(6) Uani 1 1 d . . . . .
C9 C 0.07280(19) 0.0101(7) 0.41098(12) 0.0457(7) Uani 1 1 d . . . . .
H9A H 0.0517 0.1723 0.4328 0.055 Uiso 1 1 calc R U . . .
H9AB H 0.0174 -0.0658 0.3899 0.055 Uiso 1 1 calc R U . . .
C8 C 0.1482(2) 0.1021(7) 0.36896(12) 0.0495(8) Uani 1 1 d . . . . .
H8A H 0.1584 -0.0480 0.3414 0.059 Uiso 1 1 calc R U . . .
H8AB H 0.1251 0.2669 0.3480 0.059 Uiso 1 1 calc R U . . .
C7 C 0.24123(19) 0.1711(6) 0.39908(11) 0.0390(6) Uani 1 1 d . . . . .
C6A C 0.36698(19) 0.6409(6) 0.31405(11) 0.0382(6) Uani 1 1 d . . . . .
C6 C 0.4901(2) 1.1218(7) 0.22566(14) 0.0552(8) Uani 1 1 d . . . . .
H00L H 0.4480 1.1780 0.1961 0.066 Uiso 1 1 calc R U . . .
C10 C 0.26504(18) 0.0260(6) 0.45378(11) 0.0381(6) Uani 1 1 d . . . . .
C11 C 0.19790(18) -0.1681(6) 0.47659(11) 0.0370(6) Uani 1 1 d . . . . .
C12 C 0.22849(19) -0.3172(6) 0.52685(12) 0.0408(7) Uani 1 1 d . . . . .
C13 C 0.3180(2) -0.2719(7) 0.55332(13) 0.0507(8) Uani 1 1 d . . . . .
H13 H 0.3359 -0.3740 0.5860 0.061 Uiso 1 1 calc R U . . .
C14 C 0.3799(2) -0.0769(8) 0.53131(14) 0.0573(9) Uani 1 1 d . . . . .
H14 H 0.4393 -0.0426 0.5494 0.069 Uiso 1 1 calc R U . . .
C15 C 0.3530(2) 0.0689(7) 0.48170(13) 0.0484(7) Uani 1 1 d . . . . .
H15 H 0.3955 0.1998 0.4667 0.058 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
C1 S1 C6A 88.14(13) . . ?
C2 C1 C5 122.2(3) . . ?
C2 C1 S1 128.3(2) . . ?
C5 C1 S1 109.5(2) . . ?
O2 N1 O1 121.2(3) . . ?
O2 N1 C12 119.4(3) . . ?
O1 N1 C12 119.4(2) . . ?
C11 N2 C9 121.1(2) . . ?
C11 N2 H2 119.5 . . ?
C9 N2 H2 119.5 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C6A N4 N3 113.0(2) . . ?
C6A N4 H4 123.5 . . ?
N3 N4 H4 123.5 . . ?
C6 C4 C3 121.7(3) . . ?
C6 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C7 N3 N4 120.4(2) . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C6A N5 C5 108.2(2) . . ?
C1 C5 N5 116.2(2) . . ?
C1 C5 C6 118.2(3) . . ?
N5 C5 C6 125.6(2) . . ?
N2 C9 C8 110.9(2) . . ?
N2 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N2 C9 H9AB 109.5 . . ?
C8 C9 H9AB 109.5 . . ?
H9A C9 H9AB 108.0 . . ?
C7 C8 C9 111.4(2) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8AB 109.3 . . ?
C9 C8 H8AB 109.3 . . ?
H8A C8 H8AB 108.0 . . ?
N3 C7 C10 116.4(2) . . ?
N3 C7 C8 125.2(3) . . ?
C10 C7 C8 118.4(2) . . ?
N5 C6A N4 125.0(2) . . ?
N5 C6A S1 117.8(2) . . ?
N4 C6A S1 117.2(2) . . ?
C4 C6 C5 119.3(3) . . ?
C4 C6 H00L 120.3 . . ?
C5 C6 H00L 120.3 . . ?
C15 C10 C11 119.9(3) . . ?
C15 C10 C7 120.8(2) . . ?
C11 C10 C7 119.2(2) . . ?
N2 C11 C12 124.3(2) . . ?
N2 C11 C10 119.4(2) . . ?
C12 C11 C10 116.3(2) . . ?
C13 C12 C11 122.2(3) . . ?
C13 C12 N1 116.0(3) . . ?
C11 C12 N1 121.8(2) . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.2(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C10 C15 C14 122.2(3) . . ?
C10 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
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 1.735(3) . ?
S1 C6A 1.743(3) . ?
C1 C2 1.391(4) . ?
C1 C5 1.393(4) . ?
O1 N1 1.229(3) . ?
N1 O2 1.218(3) . ?
N1 C12 1.442(4) . ?
N2 C11 1.353(3) . ?
N2 C9 1.442(4) . ?
N2 H2 0.8600 . ?
C2 C3 1.379(4) . ?
C2 H2A 0.9300 . ?
N4 C6A 1.368(4) . ?
N4 N3 1.371(3) . ?
N4 H4 0.8600 . ?
C4 C6 1.375(4) . ?
C4 C3 1.381(5) . ?
C4 H4 0.9300 . ?
N3 C7 1.280(4) . ?
C3 H3 0.9300 . ?
N5 C6A 1.303(3) . ?
N5 C5 1.396(4) . ?
C5 C6 1.403(4) . ?
C9 C8 1.515(4) . ?
C9 H9A 0.9700 . ?
C9 H9AB 0.9700 . ?
C8 C7 1.490(4) . ?
C8 H8A 0.9700 . ?
C8 H8AB 0.9700 . ?
C7 C10 1.476(4) . ?
C6 H00L 0.9300 . ?
C10 C15 1.383(4) . ?
C10 C11 1.422(4) . ?
C11 C12 1.422(4) . ?
C12 C13 1.389(4) . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.388(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.86 2.34 2.993(3) 132.4 3_546
C9 H9A O1 0.97 2.66 3.455(4) 140.0 1_565
N4 H4N N5 0.86 2.44 3.246(3) 156.0 2_545
C2 H2A O2 0.93 2.67 3.571(4) 163.9 3_656
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
C6A S1 C1 C2 -178.7(3) . . . . ?
C6A S1 C1 C5 1.6(2) . . . . ?
C5 C1 C2 C3 0.6(4) . . . . ?
S1 C1 C2 C3 -179.1(2) . . . . ?
C6A N4 N3 C7 -177.5(2) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C6 C4 C3 C2 -1.1(5) . . . . ?
C2 C1 C5 N5 178.9(3) . . . . ?
S1 C1 C5 N5 -1.3(3) . . . . ?
C2 C1 C5 C6 -0.7(4) . . . . ?
S1 C1 C5 C6 179.1(2) . . . . ?
C6A N5 C5 C1 0.1(3) . . . . ?
C6A N5 C5 C6 179.7(3) . . . . ?
C11 N2 C9 C8 47.1(4) . . . . ?
N2 C9 C8 C7 -48.8(3) . . . . ?
N4 N3 C7 C10 179.5(2) . . . . ?
N4 N3 C7 C8 2.8(4) . . . . ?
C9 C8 C7 N3 -155.1(3) . . . . ?
C9 C8 C7 C10 28.3(4) . . . . ?
C5 N5 C6A N4 -178.8(3) . . . . ?
C5 N5 C6A S1 1.3(3) . . . . ?
N3 N4 C6A N5 -176.0(2) . . . . ?
N3 N4 C6A S1 3.9(3) . . . . ?
C1 S1 C6A N5 -1.7(2) . . . . ?
C1 S1 C6A N4 178.3(2) . . . . ?
C3 C4 C6 C5 1.0(5) . . . . ?
C1 C5 C6 C4 -0.1(5) . . . . ?
N5 C5 C6 C4 -179.7(3) . . . . ?
N3 C7 C10 C15 -0.9(4) . . . . ?
C8 C7 C10 C15 176.0(3) . . . . ?
N3 C7 C10 C11 -178.5(2) . . . . ?
C8 C7 C10 C11 -1.6(4) . . . . ?
C9 N2 C11 C12 160.7(3) . . . . ?
C9 N2 C11 C10 -19.7(4) . . . . ?
C15 C10 C11 N2 177.9(3) . . . . ?
C7 C10 C11 N2 -4.5(4) . . . . ?
C15 C10 C11 C12 -2.5(4) . . . . ?
C7 C10 C11 C12 175.1(2) . . . . ?
N2 C11 C12 C13 -178.8(3) . . . . ?
C10 C11 C12 C13 1.6(4) . . . . ?
N2 C11 C12 N1 -0.2(4) . . . . ?
C10 C11 C12 N1 -179.8(2) . . . . ?
O2 N1 C12 C13 -1.5(4) . . . . ?
O1 N1 C12 C13 -179.4(3) . . . . ?
O2 N1 C12 C11 179.8(3) . . . . ?
O1 N1 C12 C11 1.9(4) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
N1 C12 C13 C14 -178.3(3) . . . . ?
C12 C13 C14 C15 -1.5(5) . . . . ?
C11 C10 C15 C14 1.5(5) . . . . ?
C7 C10 C15 C14 -176.0(3) . . . . ?
C13 C14 C15 C10 0.6(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346835
