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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/83/7228308.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_7228308
loop_
_publ_author_name
'shukla, rahul'
'Khan, Imtiaz'
'Ibrar, Aliya'
'Simpson, Jim'
'Chopra, Deepak'
_publ_section_title
;
 Complex Electronic interplay of -hole and π-hole interactions in
 crystals of halogen substituted 1,3,4-oxadiazol-2(3H)-thiones
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00678K
_journal_year                    2017
_chemical_formula_moiety         'C9 H7 Cl N2 O S'
_chemical_formula_sum            'C9 H7 Cl N2 O S'
_chemical_formula_weight         226.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-19 deposited with the CCDC.
2017-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.878(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.7860(5)
_cell_length_b                   12.8784(5)
_cell_length_c                   13.3520(6)
_cell_measurement_reflns_used    9861
_cell_measurement_temperature    91(2)
_cell_measurement_theta_max      28.80
_cell_measurement_theta_min      2.33
_cell_volume                     1961.07(14)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2011)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material
;
'SHELXL-2014/7 (Sheldrick, 2014), enCIFer (Allen et al., 2004), 
PLATON (Spek, 2009),  PublCIF (Westrip 2010), WINGX (Farrugia 1997)
;
_computing_structure_refinement
;
'SHELXL-2014/7 (Sheldrick, 2014) & TITAN (Hunter & Simpson, 1999)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999)
;
_diffrn_ambient_temperature      91(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1333
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49037
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.052
_diffrn_reflns_theta_min         1.786
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 2011)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.580
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         5234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0413
_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)+(0.0595P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1160
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4070
_reflns_number_total             5234
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce00678k2.cif
_cod_data_source_block           OT3
_cod_database_code               7228308
_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   0.692
_shelx_estimated_absorpt_t_max   0.857
_exptl_absorpt_special_details
;
?
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.04495(10) 0.35668(9) 0.29173(10) 0.0185(3) Uani 1 1 d . .
C12 C 0.04311(14) 0.41440(12) 0.37751(14) 0.0171(3) Uani 1 1 d . .
S12 S 0.15819(4) 0.47978(4) 0.46981(4) 0.02074(12) Uani 1 1 d . .
N13 N -0.06499(13) 0.40575(11) 0.36505(12) 0.0183(3) Uani 1 1 d . .
H13N H -0.0877(18) 0.4323(14) 0.4044(17) 0.022 Uiso 1 1 d . U
N14 N -0.13613(12) 0.34697(11) 0.27320(12) 0.0199(3) Uani 1 1 d . .
C15 C -0.06721(14) 0.31894(13) 0.23178(14) 0.0186(4) Uani 1 1 d . .
C16 C -0.09444(16) 0.25345(14) 0.13175(15) 0.0241(4) Uani 1 1 d . .
H16A H -0.1806 0.2486 0.0866 0.029 Uiso 1 1 calc R U
H16B H -0.0639 0.1825 0.1565 0.029 Uiso 1 1 calc R U
C11' C -0.04164(15) 0.29637(13) 0.05888(14) 0.0219(4) Uani 1 1 d . .
C12' C -0.10600(16) 0.35993(13) -0.03326(15) 0.0235(4) Uani 1 1 d . .
H11' H -0.1855 0.3752 -0.0524 0.028 Uiso 1 1 calc R U
C13' C -0.05602(16) 0.40109(14) -0.09713(16) 0.0252(4) Uani 1 1 d . .
H13' H -0.1005 0.4444 -0.1597 0.030 Uiso 1 1 calc R U
C14' C 0.05951(16) 0.37844(13) -0.06871(14) 0.0215(4) Uani 1 1 d . .
Cl14 Cl 0.12490(4) 0.43068(3) -0.14753(4) 0.02919(14) Uani 1 1 d . .
C15' C 0.12620(15) 0.31481(14) 0.02231(15) 0.0238(4) Uani 1 1 d . .
H15' H 0.2057 0.2997 0.0411 0.029 Uiso 1 1 calc R U
C16' C 0.07416(15) 0.27427(14) 0.08452(15) 0.0235(4) Uani 1 1 d . .
H16' H 0.1186 0.2302 0.1464 0.028 Uiso 1 1 calc R U
O2 O 0.46121(10) 0.12814(8) 0.74751(9) 0.0174(3) Uani 1 1 d . .
C22 C 0.46202(15) 0.06940(12) 0.83324(14) 0.0173(4) Uani 1 1 d . .
S22 S 0.34550(4) 0.00495(3) 0.82391(4) 0.02066(12) Uani 1 1 d . .
N23 N 0.56882(12) 0.07951(11) 0.91707(12) 0.0179(3) Uani 1 1 d . .
H23N H 0.5960(17) 0.0561(14) 0.9870(16) 0.021 Uiso 1 1 d . U
N24 N 0.63905(12) 0.14488(10) 0.88980(12) 0.0185(3) Uani 1 1 d . .
C25 C 0.57094(14) 0.17170(12) 0.78855(14) 0.0161(3) Uani 1 1 d . .
C26 C 0.59491(14) 0.24510(13) 0.71581(14) 0.0182(4) Uani 1 1 d . .
H26A H 0.6807 0.2502 0.7428 0.022 Uiso 1 1 calc R U
H26B H 0.5659 0.3149 0.7221 0.022 Uiso 1 1 calc R U
C21' C 0.53773(14) 0.21251(12) 0.59352(14) 0.0171(3) Uani 1 1 d . .
C22' C 0.43093(14) 0.25572(13) 0.51869(14) 0.0189(4) Uani 1 1 d . .
H22' H 0.3966 0.3086 0.5438 0.023 Uiso 1 1 calc R U
C23' C 0.37388(15) 0.22244(13) 0.40769(14) 0.0198(4) Uani 1 1 d . .
H23' H 0.3010 0.2521 0.3569 0.024 Uiso 1 1 calc R U
C24' C 0.42513(15) 0.14546(13) 0.37256(14) 0.0190(4) Uani 1 1 d . .
Cl24 Cl 0.35023(4) 0.09978(3) 0.23472(4) 0.02529(13) Uani 1 1 d . .
C25' C 0.53260(15) 0.10316(13) 0.44417(14) 0.0206(4) Uani 1 1 d . .
H25' H 0.5677 0.0519 0.4180 0.025 Uiso 1 1 calc R U
C26' C 0.58841(15) 0.13664(13) 0.55469(14) 0.0191(4) Uani 1 1 d . .
H26' H 0.6620 0.1076 0.6046 0.023 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'
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_3
C12 O1 C15 105.64(12) .
N13 C12 O1 105.11(14) .
N13 C12 S12 131.51(14) .
O1 C12 S12 123.36(12) .
C12 N13 N14 113.02(14) .
C12 N13 H13N 124.3(15) .
N14 N13 H13N 122.7(15) .
C15 N14 N13 103.43(14) .
N14 C15 O1 112.77(14) .
N14 C15 C16 128.32(15) .
O1 C15 C16 118.91(15) .
C15 C16 C11' 112.29(14) .
C15 C16 H16A 109.1 .
C11' C16 H16A 109.1 .
C15 C16 H16B 109.1 .
C11' C16 H16B 109.1 .
H16A C16 H16B 107.9 .
C16' C11' C12' 118.39(17) .
C16' C11' C16 120.05(16) .
C12' C11' C16 121.55(16) .
C13' C12' C11' 121.09(17) .
C13' C12' H11' 119.5 .
C11' C12' H11' 119.5 .
C14' C13' C12' 119.04(17) .
C14' C13' H13' 120.5 .
C12' C13' H13' 120.5 .
C13' C14' C15' 121.43(17) .
C13' C14' Cl14 119.81(14) .
C15' C14' Cl14 118.76(14) .
C16' C15' C14' 118.45(17) .
C16' C15' H15' 120.8 .
C14' C15' H15' 120.8 .
C15' C16' C11' 121.60(16) .
C15' C16' H16' 119.2 .
C11' C16' H16' 119.2 .
C22 O2 C25 105.78(12) .
N23 C22 O2 105.53(14) .
N23 C22 S22 131.32(14) .
O2 C22 S22 123.13(12) .
C22 N23 N24 112.24(14) .
C22 N23 H23N 128.2(13) .
N24 N23 H23N 119.1(12) .
C25 N24 N23 103.16(13) .
N24 C25 O2 113.27(14) .
N24 C25 C26 128.31(15) .
O2 C25 C26 118.36(14) .
C25 C26 C21' 112.77(13) .
C25 C26 H26A 109.0 .
C21' C26 H26A 109.0 .
C25 C26 H26B 109.0 .
C21' C26 H26B 109.0 .
H26A C26 H26B 107.8 .
C22' C21' C26' 118.86(16) .
C22' C21' C26 120.08(15) .
C26' C21' C26 121.02(15) .
C23' C22' C21' 120.87(16) .
C23' C22' H22' 119.6 .
C21' C22' H22' 119.6 .
C24' C23' C22' 118.81(15) .
C24' C23' H23' 120.6 .
C22' C23' H23' 120.6 .
C23' C24' C25' 121.57(16) .
C23' C24' Cl24 118.72(13) .
C25' C24' Cl24 119.71(13) .
C24' Cl24 S12 169.51(6) 4_565
C24' C25' C26' 119.09(16) .
C24' C25' H25' 120.5 .
C26' C25' H25' 120.5 .
C25' C26' C21' 120.76(16) .
C25' C26' H26' 119.6 .
C21' C26' H26' 119.6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C12 1.3744(19) .
O1 C15 1.3769(19) .
C12 N13 1.320(2) .
C12 S12 1.6593(17) .
N13 N14 1.3769(19) .
N13 H13N 0.784(19) .
N14 C15 1.286(2) .
C15 C16 1.482(2) .
C16 C11' 1.517(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C11' C16' 1.390(2) .
C11' C12' 1.395(2) .
C12' C13' 1.382(3) .
C12' H11' 0.9500 .
C13' C14' 1.380(2) .
C13' H13' 0.9500 .
C14' C15' 1.392(2) .
C14' Cl14 1.7478(18) .
C15' C16' 1.380(3) .
C15' H15' 0.9500 .
C16' H16' 0.9500 .
O2 C22 1.3681(19) .
O2 C25 1.3742(19) .
C22 N23 1.324(2) .
C22 S22 1.6603(17) .
N23 N24 1.3939(19) .
N23 H23N 0.889(19) .
N24 C25 1.281(2) .
C25 C26 1.483(2) .
C26 C21' 1.516(2) .
C26 H26A 0.9900 .
C26 H26B 0.9900 .
C21' C22' 1.393(2) .
C21' C26' 1.395(2) .
C22' C23' 1.391(2) .
C22' H22' 0.9500 .
C23' C24' 1.382(2) .
C23' H23' 0.9500 .
C24' C25' 1.382(2) .
C24' Cl24 1.7484(17) .
Cl24 S12 3.4259(6) 4_565
C25' C26' 1.386(2) .
C25' H25' 0.9500 .
C26' H26' 0.9500 .
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
N13 H13N S12 0.784(19) 2.507(19) 3.2911(16) 178.9(19) 3_566
C26 H26A N14 0.99 2.52 3.382(2) 145.3 4_666
C26' H26' N14 0.95 2.61 3.416(2) 142.8 4_666
N23 H23N S22 0.889(19) 2.417(19) 3.3043(15) 175.4(17) 3_657
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_4
C15 O1 C12 N13 1.29(16) .
C15 O1 C12 S12 -177.42(12) .
O1 C12 N13 N14 -1.51(18) .
S12 C12 N13 N14 177.05(13) .
C12 N13 N14 C15 1.08(19) .
N13 N14 C15 O1 -0.18(18) .
N13 N14 C15 C16 179.63(17) .
C12 O1 C15 N14 -0.70(18) .
C12 O1 C15 C16 179.47(14) .
N14 C15 C16 C11' 136.72(19) .
O1 C15 C16 C11' -43.5(2) .
C15 C16 C11' C16' 83.9(2) .
C15 C16 C11' C12' -94.87(19) .
C16' C11' C12' C13' -0.7(3) .
C16 C11' C12' C13' 178.08(16) .
C11' C12' C13' C14' 0.1(3) .
C12' C13' C14' C15' 0.3(3) .
C12' C13' C14' Cl14 -179.39(14) .
C13' C14' C15' C16' 0.0(3) .
Cl14 C14' C15' C16' 179.67(14) .
C14' C15' C16' C11' -0.6(3) .
C12' C11' C16' C15' 1.0(3) .
C16 C11' C16' C15' -177.82(16) .
C25 O2 C22 N23 -0.90(16) .
C25 O2 C22 S22 177.70(11) .
O2 C22 N23 N24 0.81(18) .
S22 C22 N23 N24 -177.62(12) .
C22 N23 N24 C25 -0.37(18) .
N23 N24 C25 O2 -0.24(18) .
N23 N24 C25 C26 176.88(16) .
C22 O2 C25 N24 0.73(18) .
C22 O2 C25 C26 -176.70(14) .
N24 C25 C26 C21' 144.49(17) .
O2 C25 C26 C21' -38.5(2) .
C25 C26 C21' C22' 97.53(18) .
C25 C26 C21' C26' -80.21(19) .
C26' C21' C22' C23' 1.5(2) .
C26 C21' C22' C23' -176.28(14) .
C21' C22' C23' C24' 0.0(2) .
C22' C23' C24' C25' -1.7(2) .
C22' C23' C24' Cl24 177.24(12) .
C23' C24' Cl24 S12 -31.6(4) 4_565
C25' C24' Cl24 S12 147.4(3) 4_565
C23' C24' C25' C26' 2.0(3) .
Cl24 C24' C25' C26' -176.97(13) .
C24' C25' C26' C21' -0.5(3) .
C22' C21' C26' C25' -1.3(2) .
C26 C21' C26' C25' 176.51(15) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203517
