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#$Date: 2025-03-04 21:24:29 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298138 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/37/1573708.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_1573708
loop_
_publ_author_name
'Sentürk, Bengi'
'Butschke, Burkhard'
'Eisenreich, Fabian'
_publ_section_title
;
 Thiosemicarbazones as versatile photoswitches with light-controllable
 supramolecular activity.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              3130
_journal_page_last               3140
_journal_paper_doi               10.1039/d4sc08530b
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C14 H11 Cl2 N3 S'
_chemical_formula_sum            'C14 H11 Cl2 N3 S'
_chemical_formula_weight         324.22
_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
_atom_sites_solution_primary     direct
_audit_creation_method
;FinalCif V137 by Daniel Kratzert, Freiburg 2024, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2024-05-24 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                92.336(4)
_cell_angle_beta                 96.812(11)
_cell_angle_gamma                111.933(13)
_cell_formula_units_Z            2
_cell_length_a                   7.866(2)
_cell_length_b                   8.231(2)
_cell_length_c                   11.963(5)
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.4645
_cell_measurement_theta_min      2.679
_cell_volume                     710.4(4)
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_collection
'Bruker BIS 2018.9.0.3/05-Dec-2018 and APEX5_2023.9-2'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33050
_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         31.518
_diffrn_reflns_theta_min         1.722
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.6
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
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    1.516
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_recrystallization_method
'Crystals were obtained at room temperature from a mixture of dichloromethane and ethanol by slow solvent evaporation.'
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_min          0.162
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         4732
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0264
_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)+(0.0301P)²+0.3561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4300
_reflns_number_total             4732
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc08530b2.cif
_cod_data_source_block           Eisenreich_TSC_13_a
_cod_depositor_comments
'Adding full bibliography for 1573706--1573712.cif.'
_cod_original_cell_volume        710.3(4)
_cod_database_code               1573708
_shelx_shelxl_version_number     2019/3
_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   0.778
_shelx_estimated_absorpt_t_max   0.910
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
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 0.25214(4) 0.72448(3) 0.97677(2) 0.02021(6) Uani 1 1 d . . . . .
Cl2 Cl 0.15773(4) 0.04931(3) 0.84415(2) 0.01577(6) Uani 1 1 d . . . . .
S1 S 0.11921(4) 0.37352(3) 0.38691(2) 0.01488(6) Uani 1 1 d . . . . .
N1 N 0.29239(13) 0.22829(12) 0.53363(7) 0.01432(16) Uani 1 1 d D . . . .
H1N H 0.330(2) 0.2217(19) 0.6019(10) 0.017 Uiso 1 1 d D U . . .
N2 N 0.15462(12) 0.39912(11) 0.60947(7) 0.01301(15) Uani 1 1 d D . . . .
H2N H 0.0860(19) 0.4601(18) 0.6031(11) 0.016 Uiso 1 1 d D U . . .
N3 N 0.21467(12) 0.36154(11) 0.71403(7) 0.01240(15) Uani 1 1 d D . . . .
C1 C 0.19318(14) 0.32886(12) 0.51586(8) 0.01191(16) Uani 1 1 d D . . . .
C2 C 0.34809(14) 0.14477(13) 0.44565(8) 0.01229(17) Uani 1 1 d D . . . .
C3 C 0.21530(14) 0.01006(13) 0.37179(9) 0.01448(18) Uani 1 1 d . . . . .
H3 H 0.087742 -0.026001 0.379019 0.017 Uiso 1 1 calc R U . . .
C4 C 0.27137(15) -0.07121(14) 0.28726(9) 0.01579(18) Uani 1 1 d . . . . .
H4 H 0.181620 -0.162901 0.236253 0.019 Uiso 1 1 calc R U . . .
C5 C 0.45842(15) -0.01877(14) 0.27708(9) 0.01593(18) Uani 1 1 d . . . . .
H5 H 0.495886 -0.073811 0.218708 0.019 Uiso 1 1 calc R U . . .
C6 C 0.59050(14) 0.11416(14) 0.35232(9) 0.01613(18) Uani 1 1 d . . . . .
H6 H 0.718205 0.148789 0.345891 0.019 Uiso 1 1 calc R U . . .
C7 C 0.53544(14) 0.19679(13) 0.43737(8) 0.01440(18) Uani 1 1 d . . . . .
H7 H 0.625141 0.287562 0.488981 0.017 Uiso 1 1 calc R U . . .
C8 C 0.16914(14) 0.42834(13) 0.79885(8) 0.01288(17) Uani 1 1 d . . . . .
H8 H 0.102044 0.502527 0.786637 0.015 Uiso 1 1 calc R U . . .
C9 C 0.21949(13) 0.39151(13) 0.91462(8) 0.01169(16) Uani 1 1 d . . . . .
C10 C 0.26073(15) 0.52148(13) 1.00494(8) 0.01404(17) Uani 1 1 d . . . . .
C11 C 0.30946(16) 0.49591(15) 1.11618(9) 0.01756(19) Uani 1 1 d . . . . .
H11 H 0.337183 0.587193 1.174822 0.021 Uiso 1 1 calc R U . . .
C12 C 0.31722(16) 0.33515(15) 1.14072(9) 0.0183(2) Uani 1 1 d . . . . .
H12 H 0.352458 0.316646 1.216380 0.022 Uiso 1 1 calc R U . . .
C13 C 0.27354(15) 0.20154(14) 1.05485(9) 0.01611(18) Uani 1 1 d . . . . .
H13 H 0.277319 0.091077 1.071836 0.019 Uiso 1 1 calc R U . . .
C14 C 0.22430(14) 0.22937(13) 0.94403(8) 0.01236(17) 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'
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
C1 N1 C2 124.26(8) . . ?
C1 N1 H1N 116.2(10) . . ?
C2 N1 H1N 119.4(10) . . ?
C1 N2 N3 119.21(8) . . ?
C1 N2 H2N 120.3(9) . . ?
N3 N2 H2N 120.3(9) . . ?
C8 N3 N2 116.00(9) . . ?
N1 C1 N2 116.21(9) . . ?
N1 C1 S1 124.20(8) . . ?
N2 C1 S1 119.59(8) . . ?
C7 C2 C3 121.00(9) . . ?
C7 C2 N1 119.15(9) . . ?
C3 C2 N1 119.83(9) . . ?
C4 C3 C2 119.28(10) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.30(10) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.06(9) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.04(10) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 119.31(9) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
N3 C8 C9 120.85(9) . . ?
N3 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C14 C9 C10 115.86(9) . . ?
C14 C9 C8 124.31(9) . . ?
C10 C9 C8 119.80(9) . . ?
C11 C10 C9 122.90(10) . . ?
C11 C10 Cl1 118.10(8) . . ?
C9 C10 Cl1 119.00(8) . . ?
C10 C11 C12 119.14(10) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.06(10) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 119.96(10) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 122.03(9) . . ?
C13 C14 Cl2 116.33(8) . . ?
C9 C14 Cl2 121.57(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 C10 1.7420(11) . ?
Cl2 C14 1.7394(11) . ?
S1 C1 1.6871(11) . ?
N1 C1 1.3405(13) . ?
N1 C2 1.4310(13) . ?
N1 H1N 0.845(12) . ?
N2 C1 1.3562(13) . ?
N2 N3 1.3725(12) . ?
N2 H2N 0.863(11) . ?
N3 C8 1.2837(13) . ?
C2 C7 1.3899(15) . ?
C2 C3 1.3918(14) . ?
C3 C4 1.3913(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.3923(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3912(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.3976(15) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.4699(14) . ?
C8 H8 0.9500 . ?
C9 C14 1.4068(14) . ?
C9 C10 1.4073(14) . ?
C10 C11 1.3871(15) . ?
C11 C12 1.3886(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3872(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3890(15) . ?
C13 H13 0.9500 . ?
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
C1 N2 N3 C8 -178.16(9) . . . . ?
C2 N1 C1 N2 -179.30(9) . . . . ?
C2 N1 C1 S1 -0.29(15) . . . . ?
N3 N2 C1 N1 -1.20(14) . . . . ?
N3 N2 C1 S1 179.74(7) . . . . ?
C1 N1 C2 C7 114.59(12) . . . . ?
C1 N1 C2 C3 -67.14(14) . . . . ?
C7 C2 C3 C4 -1.16(15) . . . . ?
N1 C2 C3 C4 -179.40(9) . . . . ?
C2 C3 C4 C5 0.29(15) . . . . ?
C3 C4 C5 C6 0.68(16) . . . . ?
C4 C5 C6 C7 -0.81(16) . . . . ?
C3 C2 C7 C6 1.04(15) . . . . ?
N1 C2 C7 C6 179.29(9) . . . . ?
C5 C6 C7 C2 -0.05(15) . . . . ?
N2 N3 C8 C9 177.62(9) . . . . ?
N3 C8 C9 C14 -35.65(15) . . . . ?
N3 C8 C9 C10 146.54(10) . . . . ?
C14 C9 C10 C11 2.10(15) . . . . ?
C8 C9 C10 C11 -179.92(10) . . . . ?
C14 C9 C10 Cl1 -178.34(7) . . . . ?
C8 C9 C10 Cl1 -0.35(13) . . . . ?
C9 C10 C11 C12 -0.44(17) . . . . ?
Cl1 C10 C11 C12 179.99(9) . . . . ?
C10 C11 C12 C13 -1.07(17) . . . . ?
C11 C12 C13 C14 0.82(17) . . . . ?
C12 C13 C14 C9 0.97(16) . . . . ?
C12 C13 C14 Cl2 -175.99(8) . . . . ?
C10 C9 C14 C13 -2.35(15) . . . . ?
C8 C9 C14 C13 179.76(10) . . . . ?
C10 C9 C14 Cl2 174.46(7) . . . . ?
C8 C9 C14 Cl2 -3.43(14) . . . . ?
