#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/58/2225837.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225837
loop_
_publ_author_name
'Khan, F. Nawaz'
'Manivel, P.'
'Prabakaran, K.'
'Hathwar, Venkatesha R.'
'Akkurt, Mehmet'
_publ_section_title
;
 5-(4-Chlorophenyl)-3-(2,4-dimethylthiazol-5-yl)-1,2,4-triazolo[3,4-a]isoquinoline
;
_journal_coeditor_code           FJ2293
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1056
_journal_page_last               o1057
_journal_paper_doi               10.1107/S160053681001278X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H15 Cl N4 S'
_chemical_formula_moiety         'C21 H15 Cl N4 S'
_chemical_formula_structural     'C21 H15 Cl N4 S'
_chemical_formula_sum            'C21 H15 Cl N4 S'
_chemical_formula_weight         390.89
_chemical_name_systematic
;
5-(4-Chlorophenyl)-3-(2,4-dimethylthiazol-5-yl)-1,2,4-
triazolo[3,4-a]isoquinoline
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                93.514(5)
_cell_angle_beta                 94.805(5)
_cell_angle_gamma                105.963(6)
_cell_formula_units_Z            2
_cell_length_a                   7.8286(5)
_cell_length_b                   8.1754(6)
_cell_length_c                   15.1264(9)
_cell_measurement_reflns_used    954
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      20.35
_cell_measurement_theta_min      1.95
_cell_volume                     923.92(11)
_computing_cell_refinement       'CrysAlis Pro CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis Pro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis Pro RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Oxford Xcalibur Eos (Nova) CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19579
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  0.9243
_exptl_absorpt_correction_T_min  0.8511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis Pro RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0635P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1109
_reflns_number_gt                2518
_reflns_number_total             3439
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2293.cif
_cod_data_source_block           I
_cod_database_code               2225837
_cod_database_fobs_code          2225837
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.55766(7) 0.44377(7) 0.27355(3) 0.05951(19) Uani d . 1 . .
Cl Cl1 0.90834(9) 0.16939(8) 0.06573(5) 0.0843(2) Uani d . 1 . .
N N1 0.84486(17) 0.86756(18) 0.31082(9) 0.0404(3) Uani d . 1 . .
N N2 0.69901(19) 1.0456(2) 0.36035(10) 0.0527(4) Uani d . 1 . .
N N3 0.57837(19) 0.9079(2) 0.31201(11) 0.0552(4) Uani d . 1 . .
N N4 0.4093(2) 0.4452(2) 0.11718(11) 0.0566(4) Uani d . 1 . .
C C1 0.8562(2) 1.0182(2) 0.36077(11) 0.0422(4) Uani d . 1 . .
C C2 1.0238(2) 1.1181(2) 0.40777(11) 0.0424(4) Uani d . 1 . .
C C3 1.0384(3) 1.2657(2) 0.46264(12) 0.0518(5) Uani d . 1 . .
H H3 0.9390 1.3053 0.4684 0.062 Uiso calc R 1 . .
C C4 1.2006(3) 1.3523(2) 0.50822(13) 0.0567(5) Uani d . 1 . .
H H4 1.2103 1.4503 0.5452 0.068 Uiso calc R 1 . .
C C5 1.3493(3) 1.2952(3) 0.49973(13) 0.0572(5) Uani d . 1 . .
H H5 1.4581 1.3545 0.5313 0.069 Uiso calc R 1 . .
C C6 1.3375(2) 1.1514(3) 0.44506(13) 0.0542(5) Uani d . 1 . .
H H6 1.4388 1.1150 0.4390 0.065 Uiso calc R 1 . .
C C7 1.1733(2) 1.0589(2) 0.39819(11) 0.0444(4) Uani d . 1 . .
C C8 1.1543(2) 0.9065(2) 0.34138(12) 0.0466(4) Uani d . 1 . .
H H8 1.2558 0.8710 0.3341 0.056 Uiso calc R 1 . .
C C9 0.9971(2) 0.8117(2) 0.29783(11) 0.0423(4) Uani d . 1 . .
C C10 0.9794(2) 0.6564(2) 0.23864(11) 0.0428(4) Uani d . 1 . .
C C11 1.0353(2) 0.5235(3) 0.27137(13) 0.0519(5) Uani d . 1 . .
H H11 1.0870 0.5347 0.3299 0.062 Uiso calc R 1 . .
C C12 1.0157(3) 0.3744(3) 0.21852(14) 0.0573(5) Uani d . 1 . .
H H12 1.0532 0.2853 0.2412 0.069 Uiso calc R 1 . .
C C13 0.9398(3) 0.3592(3) 0.13168(13) 0.0541(5) Uani d . 1 . .
C C14 0.8902(2) 0.4919(3) 0.09643(12) 0.0527(5) Uani d . 1 . .
H H14 0.8433 0.4820 0.0371 0.063 Uiso calc R 1 . .
C C15 0.9105(2) 0.6405(2) 0.14989(12) 0.0475(4) Uani d . 1 . .
H H15 0.8776 0.7311 0.1262 0.057 Uiso calc R 1 . .
C C16 0.6634(2) 0.8009(2) 0.28300(11) 0.0453(4) Uani d . 1 . .
C C17 0.5732(2) 0.6376(2) 0.23238(12) 0.0471(4) Uani d . 1 . .
C C18 0.4858(2) 0.6136(2) 0.14858(12) 0.0498(5) Uani d . 1 . .
C C19 0.4738(3) 0.7494(3) 0.09026(15) 0.0764(7) Uani d . 1 . .
H H19A 0.3563 0.7645 0.0884 0.115 Uiso calc R 1 . .
H H19B 0.4969 0.7176 0.0312 0.115 Uiso calc R 1 . .
H H19C 0.5605 0.8544 0.1132 0.115 Uiso calc R 1 . .
C C20 0.4383(2) 0.3425(3) 0.17513(14) 0.0558(5) Uani d . 1 . .
C C21 0.3769(4) 0.1526(3) 0.16023(18) 0.0799(7) Uani d . 1 . .
H H21A 0.2505 0.1137 0.1641 0.120 Uiso calc R 1 . .
H H21B 0.4382 0.1043 0.2048 0.120 Uiso calc R 1 . .
H H21C 0.4023 0.1173 0.1023 0.120 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
Cl Cl 0.1484 0.1585 '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'
C C 0.0033 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C17 S1 C20 . . 89.71(9) ?
C1 N1 C16 . . 104.18(13) ?
C1 N1 C9 . . 122.02(14) ?
C16 N1 C9 . . 133.80(15) ?
C1 N2 N3 . . 106.96(14) ?
C16 N3 N2 . . 109.14(14) ?
C20 N4 C18 . . 111.44(17) ?
N2 C1 N1 . . 110.74(15) ?
N2 C1 C2 . . 128.52(16) ?
N1 C1 C2 . . 120.68(14) ?
C3 C2 C7 . . 120.43(17) ?
C3 C2 C1 . . 122.28(16) ?
C7 C2 C1 . . 117.26(16) ?
C4 C3 C2 . . 119.62(18) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 120.64(19) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 120.41(19) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C7 . . 120.40(18) ?
C5 C6 H6 . . 119.8 ?
C7 C6 H6 . . 119.8 ?
C2 C7 C6 . . 118.48(17) ?
C2 C7 C8 . . 119.24(16) ?
C6 C7 C8 . . 122.28(16) ?
C9 C8 C7 . . 123.62(16) ?
C9 C8 H8 . . 118.2 ?
C7 C8 H8 . . 118.2 ?
C8 C9 N1 . . 116.99(16) ?
C8 C9 C10 . . 123.21(15) ?
N1 C9 C10 . . 119.80(14) ?
C11 C10 C15 . . 118.60(17) ?
C11 C10 C9 . . 119.53(16) ?
C15 C10 C9 . . 121.87(16) ?
C12 C11 C10 . . 121.00(18) ?
C12 C11 H11 . . 119.5 ?
C10 C11 H11 . . 119.5 ?
C13 C12 C11 . . 119.11(18) ?
C13 C12 H12 . . 120.4 ?
C11 C12 H12 . . 120.4 ?
C14 C13 C12 . . 121.03(18) ?
C14 C13 Cl1 . . 119.56(16) ?
C12 C13 Cl1 . . 119.41(16) ?
C13 C14 C15 . . 119.30(18) ?
C13 C14 H14 . . 120.3 ?
C15 C14 H14 . . 120.3 ?
C14 C15 C10 . . 120.84(18) ?
C14 C15 H15 . . 119.6 ?
C10 C15 H15 . . 119.6 ?
N3 C16 N1 . . 108.91(16) ?
N3 C16 C17 . . 123.14(15) ?
N1 C16 C17 . . 127.92(15) ?
C18 C17 C16 . . 126.79(17) ?
C18 C17 S1 . . 109.80(14) ?
C16 C17 S1 . . 123.38(14) ?
C17 C18 N4 . . 114.72(17) ?
C17 C18 C19 . . 125.94(18) ?
N4 C18 C19 . . 119.29(17) ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
N4 C20 C21 . . 124.4(2) ?
N4 C20 S1 . . 114.31(16) ?
C21 C20 S1 . . 121.26(17) ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C17 . 1.7150(19) ?
S1 C20 . 1.722(2) ?
Cl1 C13 . 1.7387(19) ?
N1 C1 . 1.382(2) ?
N1 C16 . 1.392(2) ?
N1 C9 . 1.413(2) ?
N2 C1 . 1.310(2) ?
N2 N3 . 1.376(2) ?
N3 C16 . 1.313(2) ?
N4 C20 . 1.299(3) ?
N4 C18 . 1.378(2) ?
C1 C2 . 1.441(2) ?
C2 C3 . 1.394(2) ?
C2 C7 . 1.399(2) ?
C3 C4 . 1.374(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.380(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.372(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.405(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.435(2) ?
C8 C9 . 1.351(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.475(2) ?
C10 C11 . 1.382(2) ?
C10 C15 . 1.389(2) ?
C11 C12 . 1.381(3) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.379(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.371(3) ?
C14 C15 . 1.381(2) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 C17 . 1.460(2) ?
C17 C18 . 1.365(3) ?
C18 C19 . 1.477(3) ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 C21 . 1.490(3) ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H6 N2 1_655 0.93 2.62 3.495(2) 158 yes
C8 H8 N3 1_655 0.93 2.51 3.383(2) 156 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N2 N3 C16 . . . . -0.8(2) ?
N3 N2 C1 N1 . . . . 2.2(2) ?
N3 N2 C1 C2 . . . . -174.89(17) ?
C16 N1 C1 N2 . . . . -2.68(19) ?
C9 N1 C1 N2 . . . . 177.60(14) ?
C16 N1 C1 C2 . . . . 174.71(15) ?
C9 N1 C1 C2 . . . . -5.0(2) ?
N2 C1 C2 C3 . . . . 0.4(3) ?
N1 C1 C2 C3 . . . . -176.44(16) ?
N2 C1 C2 C7 . . . . 178.86(17) ?
N1 C1 C2 C7 . . . . 2.0(2) ?
C7 C2 C3 C4 . . . . -0.7(3) ?
C1 C2 C3 C4 . . . . 177.71(16) ?
C2 C3 C4 C5 . . . . 0.4(3) ?
C3 C4 C5 C6 . . . . 0.4(3) ?
C4 C5 C6 C7 . . . . -1.1(3) ?
C3 C2 C7 C6 . . . . 0.1(3) ?
C1 C2 C7 C6 . . . . -178.40(15) ?
C3 C2 C7 C8 . . . . 179.91(16) ?
C1 C2 C7 C8 . . . . 1.4(2) ?
C5 C6 C7 C2 . . . . 0.8(3) ?
C5 C6 C7 C8 . . . . -179.03(17) ?
C2 C7 C8 C9 . . . . -2.1(3) ?
C6 C7 C8 C9 . . . . 177.69(17) ?
C7 C8 C9 N1 . . . . -0.7(3) ?
C7 C8 C9 C10 . . . . 179.18(16) ?
C1 N1 C9 C8 . . . . 4.3(2) ?
C16 N1 C9 C8 . . . . -175.35(17) ?
C1 N1 C9 C10 . . . . -175.59(15) ?
C16 N1 C9 C10 . . . . 4.8(3) ?
C8 C9 C10 C11 . . . . 56.7(2) ?
N1 C9 C10 C11 . . . . -123.46(18) ?
C8 C9 C10 C15 . . . . -122.2(2) ?
N1 C9 C10 C15 . . . . 57.7(2) ?
C15 C10 C11 C12 . . . . -3.1(3) ?
C9 C10 C11 C12 . . . . 178.05(16) ?
C10 C11 C12 C13 . . . . 0.3(3) ?
C11 C12 C13 C14 . . . . 2.5(3) ?
C11 C12 C13 Cl1 . . . . -178.02(15) ?
C12 C13 C14 C15 . . . . -2.5(3) ?
Cl1 C13 C14 C15 . . . . 178.05(13) ?
C13 C14 C15 C10 . . . . -0.4(3) ?
C11 C10 C15 C14 . . . . 3.1(3) ?
C9 C10 C15 C14 . . . . -178.05(15) ?
N2 N3 C16 N1 . . . . -0.8(2) ?
N2 N3 C16 C17 . . . . 177.39(16) ?
C1 N1 C16 N3 . . . . 2.09(18) ?
C9 N1 C16 N3 . . . . -178.24(17) ?
C1 N1 C16 C17 . . . . -176.03(17) ?
C9 N1 C16 C17 . . . . 3.6(3) ?
N3 C16 C17 C18 . . . . 66.9(3) ?
N1 C16 C17 C18 . . . . -115.2(2) ?
N3 C16 C17 S1 . . . . -111.10(18) ?
N1 C16 C17 S1 . . . . 66.8(2) ?
C20 S1 C17 C18 . . . . 1.01(14) ?
C20 S1 C17 C16 . . . . 179.31(15) ?
C16 C17 C18 N4 . . . . -178.77(15) ?
S1 C17 C18 N4 . . . . -0.5(2) ?
C16 C17 C18 C19 . . . . 3.7(3) ?
S1 C17 C18 C19 . . . . -178.11(17) ?
C20 N4 C18 C17 . . . . -0.5(2) ?
C20 N4 C18 C19 . . . . 177.28(18) ?
C18 N4 C20 C21 . . . . -178.43(18) ?
C18 N4 C20 S1 . . . . 1.3(2) ?
C17 S1 C20 N4 . . . . -1.35(15) ?
C17 S1 C20 C21 . . . . 178.36(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744845
2 PubChem 91156383
