#------------------------------------------------------------------------------
#$Date: 2022-06-06 03:52:13 +0200 (Mon 06 de Jun de 2022) $
#$Revision: 275789 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/14/7061444.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_7061444
loop_
_publ_author_name
'Dou, Li'
'Shi, Huabin'
'Niu, Xue'
'Zhang, Hong'
'Zhang, Kankan'
'Wu, Zhibing'
_publ_section_title
;
 Design, synthesis and antifungal mechanism of novel acetophenone
 derivatives containing 1,3,4-thiadiazole-2-thioethers
;
_journal_issue                   19
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9017
_journal_page_last               9023
_journal_paper_doi               10.1039/D2NJ01709A
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C16 H11 Cl N2 O S2'
_chemical_formula_sum            'C16 H11 Cl N2 O S2'
_chemical_formula_weight         346.84
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-07
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-05-10 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                105.112(2)
_cell_angle_beta                 93.310(2)
_cell_angle_gamma                111.564(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1736(4)
_cell_length_b                   8.9413(4)
_cell_length_c                   12.3309(6)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      71.966
_cell_measurement_theta_min      3.768
_cell_volume                     797.19(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20086
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.569
_diffrn_reflns_theta_min         3.768
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.585
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.2359
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.808
_refine_diff_density_min         -1.245
_refine_diff_density_rms         0.328
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0953
_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)+(0.1729P)²+0.2279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2294
_refine_ls_wR_factor_ref         0.2356
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2825
_reflns_number_total             3126
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj01709a2.cif
_cod_data_source_block           20210428wuzhibing_0m
_cod_depositor_comments          'Adding full bibliography for 7061444.cif.'
_cod_database_code               7061444
_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_max   0.432
_shelx_estimated_absorpt_t_min   0.382
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.70877(17) 1.12972(14) 0.95189(11) 0.0902(5) Uani 1 1 d . . . . .
S1 S 0.72369(11) 0.36634(10) 0.67558(6) 0.0498(3) Uani 1 1 d . . . . .
S2 S 0.73566(10) 0.02744(10) 0.57499(6) 0.0474(3) Uani 1 1 d . . . . .
O1 O 0.7806(5) -0.2695(4) 0.4417(2) 0.0732(8) Uani 1 1 d . . . . .
N1 N 0.7542(4) 0.2306(3) 0.4585(2) 0.0493(6) Uani 1 1 d . . . . .
N2 N 0.7605(4) 0.0897(3) 0.3845(2) 0.0483(6) Uani 1 1 d . . . . .
C1 C 0.7143(5) 0.9528(4) 0.8541(3) 0.0520(7) Uani 1 1 d . . . . .
C2 C 0.8756(4) 0.9424(5) 0.8417(3) 0.0587(8) Uani 1 1 d . . . . .
H2 H 0.980476 1.028377 0.885794 0.070 Uiso 1 1 calc R U . . .
C3 C 0.8814(5) 0.8036(5) 0.7631(3) 0.0580(8) Uani 1 1 d . . . . .
H3 H 0.990622 0.796213 0.754245 0.070 Uiso 1 1 calc R U . . .
C4 C 0.7252(5) 0.6748(4) 0.6973(3) 0.0506(7) Uani 1 1 d . . . . .
C5 C 0.5640(5) 0.6882(4) 0.7124(3) 0.0539(8) Uani 1 1 d . . . . .
H5 H 0.458449 0.601977 0.669347 0.065 Uiso 1 1 calc R U . . .
C6 C 0.5572(4) 0.8270(4) 0.7899(3) 0.0525(7) Uani 1 1 d . . . . .
H6 H 0.448540 0.835687 0.798737 0.063 Uiso 1 1 calc R U . . .
C7 C 0.7321(7) 0.5269(5) 0.6090(3) 0.0672(10) Uani 1 1 d . . . . .
H7A H 0.841472 0.561842 0.577804 0.081 Uiso 1 1 calc R U . . .
H7B H 0.631809 0.482101 0.547151 0.081 Uiso 1 1 calc R U . . .
C8 C 0.7401(4) 0.2140(4) 0.5605(2) 0.0405(6) Uani 1 1 d . . . . .
C9 C 0.7513(4) -0.0261(4) 0.4316(2) 0.0420(6) Uani 1 1 d . . . . .
C10 C 0.7626(4) -0.1914(4) 0.3783(2) 0.0472(7) Uani 1 1 d . . . . .
C11 C 0.7578(4) -0.2545(4) 0.2545(3) 0.0458(7) Uani 1 1 d . . . . .
C12 C 0.6727(4) -0.2114(5) 0.1747(3) 0.0538(8) Uani 1 1 d . . . . .
H12 H 0.619035 -0.135720 0.198116 0.065 Uiso 1 1 calc R U . . .
C13 C 0.6680(5) -0.2822(5) 0.0589(3) 0.0686(11) Uani 1 1 d . . . . .
H13 H 0.609921 -0.255272 0.004500 0.082 Uiso 1 1 calc R U . . .
C14 C 0.7509(6) -0.3933(6) 0.0255(4) 0.0807(14) Uani 1 1 d . . . . .
H14 H 0.748591 -0.440112 -0.051664 0.097 Uiso 1 1 calc R U . . .
C15 C 0.8360(6) -0.4347(5) 0.1047(4) 0.0772(13) Uani 1 1 d . . . . .
H15 H 0.892749 -0.507801 0.081436 0.093 Uiso 1 1 calc R U . . .
C16 C 0.8373(5) -0.3680(5) 0.2187(3) 0.0611(9) Uani 1 1 d . . . . .
H16 H 0.891780 -0.399078 0.272297 0.073 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C8 S1 C7 100.31(15) . . ?
C8 S2 C9 86.11(14) . . ?
C8 N1 N2 111.2(3) . . ?
C9 N2 N1 113.0(3) . . ?
C2 C1 Cl1 119.1(3) . . ?
C2 C1 C6 121.3(3) . . ?
C6 C1 Cl1 119.5(3) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C7 120.4(3) . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 C7 120.8(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 H6 120.6 . . ?
S1 C7 H7A 110.0 . . ?
S1 C7 H7B 110.0 . . ?
C4 C7 S1 108.5(2) . . ?
C4 C7 H7A 110.0 . . ?
C4 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
S2 C8 S1 120.68(16) . . ?
N1 C8 S1 123.9(2) . . ?
N1 C8 S2 115.4(2) . . ?
N2 C9 S2 114.3(2) . . ?
N2 C9 C10 127.5(3) . . ?
C10 C9 S2 118.1(2) . . ?
O1 C10 C9 116.9(3) . . ?
O1 C10 C11 121.5(3) . . ?
C11 C10 C9 121.6(3) . . ?
C12 C11 C10 123.2(3) . . ?
C12 C11 C16 119.8(3) . . ?
C16 C11 C10 116.9(3) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(4) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.5(4) . . ?
C15 C16 H16 119.8 . . ?
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 C1 1.739(3) . ?
S1 C7 1.814(4) . ?
S1 C8 1.742(3) . ?
S2 C8 1.711(3) . ?
S2 C9 1.733(3) . ?
O1 C10 1.211(4) . ?
N1 N2 1.370(4) . ?
N1 C8 1.311(4) . ?
N2 C9 1.294(4) . ?
C1 C2 1.370(5) . ?
C1 C6 1.377(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(5) . ?
C4 C5 1.385(5) . ?
C4 C7 1.500(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.492(4) . ?
C10 C11 1.476(4) . ?
C11 C12 1.384(5) . ?
C11 C16 1.390(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.395(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.374(6) . ?
C16 H16 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
Cl1 C1 C2 C3 -179.1(3) . . . . ?
Cl1 C1 C6 C5 179.6(3) . . . . ?
S2 C9 C10 O1 -8.1(4) . . . . ?
S2 C9 C10 C11 173.7(2) . . . . ?
O1 C10 C11 C12 154.3(3) . . . . ?
O1 C10 C11 C16 -22.9(5) . . . . ?
N1 N2 C9 S2 -0.6(3) . . . . ?
N1 N2 C9 C10 -177.0(3) . . . . ?
N2 N1 C8 S1 -178.6(2) . . . . ?
N2 N1 C8 S2 0.6(3) . . . . ?
N2 C9 C10 O1 168.1(3) . . . . ?
N2 C9 C10 C11 -10.0(5) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C2 C3 C4 C7 177.8(3) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C3 C4 C7 S1 89.1(4) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C5 C4 C7 S1 -92.9(4) . . . . ?
C6 C1 C2 C3 0.1(6) . . . . ?
C7 S1 C8 S2 -179.1(2) . . . . ?
C7 S1 C8 N1 0.1(3) . . . . ?
C7 C4 C5 C6 -177.2(3) . . . . ?
C8 S1 C7 C4 -178.3(3) . . . . ?
C8 S2 C9 N2 0.8(2) . . . . ?
C8 S2 C9 C10 177.5(2) . . . . ?
C8 N1 N2 C9 0.0(4) . . . . ?
C9 S2 C8 S1 178.44(19) . . . . ?
C9 S2 C8 N1 -0.8(2) . . . . ?
C9 C10 C11 C12 -27.6(4) . . . . ?
C9 C10 C11 C16 155.2(3) . . . . ?
C10 C11 C12 C13 -177.3(3) . . . . ?
C10 C11 C16 C15 179.0(3) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C11 C16 C15 1.6(5) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C13 C14 C15 C16 1.1(6) . . . . ?
C14 C15 C16 C11 -2.1(6) . . . . ?
C16 C11 C12 C13 -0.2(5) . . . . ?
