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#$Date: 2023-04-04 13:11:20 +0300 (Tue, 04 Apr 2023) $
#$Revision: 282323 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/63/7246372.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_7246372
loop_
_publ_author_name
'Kolesnik, Irina A.'
'Potkin, Vladimir I.'
'Grigoriev, Mikhail S.'
'Novikov, Anton P.'
'Gomila, Rosa M.'
'Podrezova, Alexandra G.'
'Brazhkin, Vadim V.'
'Zubkov, Fedor I.'
'Frontera, Antonio'
_publ_section_title
;
 Synthesis, X-ray characterization and DFT calculations of a series of
 3-substituted 4,5-dichloroisothiazoles
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              1976
_journal_page_last               1985
_journal_paper_doi               10.1039/D3CE00112A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C15 H16 Cl2 N2 O3 S'
_chemical_formula_weight         375.26
_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   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-01-18 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                105.388(6)
_cell_angle_beta                 106.574(6)
_cell_angle_gamma                100.321(6)
_cell_formula_units_Z            2
_cell_length_a                   7.3058(11)
_cell_length_b                   10.1615(14)
_cell_length_c                   12.4124(18)
_cell_measurement_reflns_used    1398
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.44
_cell_measurement_theta_min      2.93
_cell_volume                     818.5(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_av_unetI/netI     0.1363
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18356
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         4.093
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8653
_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    1.523
_exptl_crystal_description       needle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         4650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0663P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1520
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2573
_reflns_number_total             4650
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00112a2.cif
_cod_data_source_block           I596
_cod_depositor_comments
'Adding full bibliography for 7246372--7246377.cif.'
_cod_database_code               7246372
_shelx_shelxl_version_number     2018/3
_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   0.813
_shelx_estimated_absorpt_t_max   0.979
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
Cl1 Cl 0.80847(12) 0.72093(10) 1.02254(9) 0.0300(2) Uani 1 1 d . . . . .
Cl2 Cl 0.80462(11) 0.42469(10) 0.82136(9) 0.0258(2) Uani 1 1 d . . . . .
S1 S 0.36863(12) 0.61433(10) 0.89171(9) 0.0232(2) Uani 1 1 d . . . . .
O1 O 0.5796(3) 0.3213(3) 0.5215(2) 0.0238(6) Uani 1 1 d . . . . .
O2 O 0.0983(3) -0.0126(3) 0.7464(2) 0.0231(6) Uani 1 1 d . . . . .
O3 O 0.4125(3) 0.0916(3) 0.7686(2) 0.0236(6) Uani 1 1 d . . . . .
N1 N -0.0651(4) 0.2455(3) 0.5296(3) 0.0177(6) Uani 1 1 d . . . . .
H1 H -0.170(5) 0.262(4) 0.512(3) 0.021 Uiso 1 1 d . U . . .
N2 N 0.2625(4) 0.4672(3) 0.7752(3) 0.0202(6) Uani 1 1 d . . . . .
C2 C 0.0661(4) 0.2995(3) 0.4820(3) 0.0153(7) Uani 1 1 d . . . . .
C3 C 0.2596(4) 0.2973(3) 0.5268(3) 0.0139(7) Uani 1 1 d . . . . .
C4 C 0.3290(4) 0.2684(4) 0.6445(3) 0.0161(7) Uani 1 1 d . . . . .
H4A H 0.443952 0.227219 0.646764 0.019 Uiso 1 1 calc R U . . .
C5 C 0.1626(4) 0.1608(4) 0.6517(3) 0.0154(7) Uani 1 1 d . . . . .
C6 C -0.0284(4) 0.1619(4) 0.6000(3) 0.0162(7) Uani 1 1 d . . . . .
C7 C -0.0274(4) 0.3527(4) 0.3837(3) 0.0188(7) Uani 1 1 d . . . . .
H7A H -0.146298 0.378273 0.393474 0.028 Uiso 1 1 calc R U . . .
H7B H -0.064607 0.278097 0.306451 0.028 Uiso 1 1 calc R U . . .
H7C H 0.067573 0.436457 0.387129 0.028 Uiso 1 1 calc R U . . .
C8 C 0.4039(4) 0.3140(3) 0.4677(3) 0.0155(7) Uani 1 1 d . . . . .
C9 C 0.3482(5) 0.3152(4) 0.3417(3) 0.0226(8) Uani 1 1 d . . . . .
H9A H 0.229068 0.237091 0.290611 0.034 Uiso 1 1 calc R U . . .
H9B H 0.457897 0.303623 0.312823 0.034 Uiso 1 1 calc R U . . .
H9C H 0.321301 0.405773 0.339593 0.034 Uiso 1 1 calc R U . . .
C10 C 0.2128(4) 0.0708(4) 0.7243(3) 0.0183(7) Uani 1 1 d . . . . .
C11 C 0.4780(5) 0.0117(5) 0.8469(4) 0.0327(10) Uani 1 1 d . . . . .
H11A H 0.428216 -0.091455 0.801802 0.039 Uiso 1 1 calc R U . . .
H11B H 0.425915 0.031721 0.913176 0.039 Uiso 1 1 calc R U . . .
C12 C 0.7022(5) 0.0565(4) 0.8955(4) 0.0308(9) Uani 1 1 d . . . . .
H12A H 0.749990 0.009698 0.953235 0.046 Uiso 1 1 calc R U . . .
H12B H 0.749955 0.159760 0.934913 0.046 Uiso 1 1 calc R U . . .
H12C H 0.752161 0.029300 0.829824 0.046 Uiso 1 1 calc R U . . .
C13 C -0.2126(4) 0.0773(4) 0.6067(3) 0.0213(8) Uani 1 1 d . . . . .
H13A H -0.318032 0.041758 0.528102 0.032 Uiso 1 1 calc R U . . .
H13B H -0.255608 0.137833 0.664835 0.032 Uiso 1 1 calc R U . . .
H13C H -0.184736 -0.003026 0.631598 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3967(4) 0.4040(4) 0.7501(3) 0.0159(7) Uani 1 1 d . . . . .
C15 C 0.5973(4) 0.4783(4) 0.8301(3) 0.0176(7) Uani 1 1 d . . . . .
C16 C 0.6042(4) 0.5984(4) 0.9133(3) 0.0202(7) Uani 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 '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
N2 S1 C16 94.65(15) . . ?
C10 O3 C11 115.1(2) . . ?
C2 N1 C6 124.2(2) . . ?
C2 N1 H1 116(3) . . ?
C6 N1 H1 120(3) . . ?
C14 N2 S1 111.1(2) . . ?
N1 C2 C3 118.0(3) . . ?
N1 C2 C7 113.4(2) . . ?
C3 C2 C7 128.6(3) . . ?
C2 C3 C8 124.8(3) . . ?
C2 C3 C4 118.4(2) . . ?
C8 C3 C4 116.8(2) . . ?
C14 C4 C5 110.5(3) . . ?
C14 C4 C3 111.1(3) . . ?
C5 C4 C3 110.0(3) . . ?
C14 C4 H4A 108.4 . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4A 108.4 . . ?
C6 C5 C10 122.1(3) . . ?
C6 C5 C4 118.2(3) . . ?
C10 C5 C4 119.3(3) . . ?
C5 C6 N1 118.9(3) . . ?
C5 C6 C13 127.5(3) . . ?
N1 C6 C13 113.5(2) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 C3 118.9(3) . . ?
O1 C8 C9 118.2(3) . . ?
C3 C8 C9 122.9(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 O3 121.6(3) . . ?
O2 C10 C5 127.4(3) . . ?
O3 C10 C5 110.9(3) . . ?
O3 C11 C12 107.9(3) . . ?
O3 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
O3 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 113.5(3) . . ?
N2 C14 C4 119.2(3) . . ?
C15 C14 C4 127.4(3) . . ?
C16 C15 C14 111.6(3) . . ?
C16 C15 Cl2 123.5(3) . . ?
C14 C15 Cl2 124.9(3) . . ?
C15 C16 Cl1 127.9(2) . . ?
C15 C16 S1 109.2(2) . . ?
Cl1 C16 S1 122.9(2) . . ?
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
Cl1 C16 1.703(4) . ?
Cl2 C15 1.720(3) . ?
S1 N2 1.651(3) . ?
S1 C16 1.709(3) . ?
O1 C8 1.245(3) . ?
O2 C10 1.222(4) . ?
O3 C10 1.359(4) . ?
O3 C11 1.458(4) . ?
N1 C2 1.370(4) . ?
N1 C6 1.379(4) . ?
N1 H1 0.80(3) . ?
N2 C14 1.329(4) . ?
C2 C3 1.371(4) . ?
C2 C7 1.501(4) . ?
C3 C8 1.456(4) . ?
C3 C4 1.528(4) . ?
C4 C14 1.512(5) . ?
C4 C5 1.523(4) . ?
C4 H4A 1.0000 . ?
C5 C6 1.363(4) . ?
C5 C10 1.467(4) . ?
C6 C13 1.498(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.504(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.509(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.442(4) . ?
C15 C16 1.357(5) . ?
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
_geom_hbond_publ_flag
N1 H1 O1 0.80(3) 2.05(3) 2.819(3) 162(4) 1_455 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 S1 N2 C14 0.0(3) . . . . ?
C6 N1 C2 C3 -14.9(5) . . . . ?
C6 N1 C2 C7 164.4(3) . . . . ?
N1 C2 C3 C8 162.8(3) . . . . ?
C7 C2 C3 C8 -16.3(6) . . . . ?
N1 C2 C3 C4 -14.2(5) . . . . ?
C7 C2 C3 C4 166.7(3) . . . . ?
C2 C3 C4 C14 -86.4(3) . . . . ?
C8 C3 C4 C14 96.4(3) . . . . ?
C2 C3 C4 C5 36.2(4) . . . . ?
C8 C3 C4 C5 -141.0(3) . . . . ?
C14 C4 C5 C6 89.6(4) . . . . ?
C3 C4 C5 C6 -33.4(4) . . . . ?
C14 C4 C5 C10 -83.7(3) . . . . ?
C3 C4 C5 C10 153.2(3) . . . . ?
C10 C5 C6 N1 -177.9(3) . . . . ?
C4 C5 C6 N1 9.0(5) . . . . ?
C10 C5 C6 C13 0.0(6) . . . . ?
C4 C5 C6 C13 -173.1(3) . . . . ?
C2 N1 C6 C5 17.7(5) . . . . ?
C2 N1 C6 C13 -160.5(3) . . . . ?
C2 C3 C8 O1 174.4(3) . . . . ?
C4 C3 C8 O1 -8.6(5) . . . . ?
C2 C3 C8 C9 -8.9(5) . . . . ?
C4 C3 C8 C9 168.1(3) . . . . ?
C11 O3 C10 O2 -2.2(5) . . . . ?
C11 O3 C10 C5 177.2(3) . . . . ?
C6 C5 C10 O2 1.1(6) . . . . ?
C4 C5 C10 O2 174.2(3) . . . . ?
C6 C5 C10 O3 -178.2(3) . . . . ?
C4 C5 C10 O3 -5.2(4) . . . . ?
C10 O3 C11 C12 -175.4(3) . . . . ?
S1 N2 C14 C15 0.4(3) . . . . ?
S1 N2 C14 C4 -178.9(2) . . . . ?
C5 C4 C14 N2 -52.1(4) . . . . ?
C3 C4 C14 N2 70.3(3) . . . . ?
C5 C4 C14 C15 128.7(3) . . . . ?
C3 C4 C14 C15 -108.9(3) . . . . ?
N2 C14 C15 C16 -0.7(4) . . . . ?
C4 C14 C15 C16 178.5(3) . . . . ?
N2 C14 C15 Cl2 -179.8(2) . . . . ?
C4 C14 C15 Cl2 -0.5(5) . . . . ?
C14 C15 C16 Cl1 -178.0(2) . . . . ?
Cl2 C15 C16 Cl1 1.0(5) . . . . ?
C14 C15 C16 S1 0.7(3) . . . . ?
Cl2 C15 C16 S1 179.71(18) . . . . ?
N2 S1 C16 C15 -0.4(3) . . . . ?
N2 S1 C16 Cl1 178.4(2) . . . . ?
