#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:57:08 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299067 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160213.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_7160213
loop_
_publ_author_name
'Cheruthu, Nusaiba Madappuram'
'Hashim, P. K.'
'Sahu, Saugata'
'Takahashi, Kiyonori'
'Nakamura, Takayoshi'
'Mitomo, Hideyuki'
'Ijiro, Kuniharu'
'Tamaoki, Nobuyuki'
_publ_section_title
;
 Azophotoswitches containing thiazole, isothiazole, thiadiazole, and
 isothiadiazole.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              207
_journal_page_last               212
_journal_paper_doi               10.1039/d4ob01573h
_journal_volume                  23
_journal_year                    2024
_chemical_formula_moiety         'C8 H6 N4 S'
_chemical_formula_sum            'C8 H6 N4 S'
_chemical_formula_weight         190.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-16
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2024-07-16 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.039(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1698(4)
_cell_length_b                   5.5451(3)
_cell_length_c                   19.2296(9)
_cell_measurement_reflns_used    7106
_cell_measurement_temperature    200.00(14)
_cell_measurement_theta_max      71.9670
_cell_measurement_theta_min      2.3440
_cell_volume                     864.58(8)
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  89.00   0.50    1.37    --    0.00  46.00 -90.00  356
  2  ω    -84.00  94.00   0.50    5.48    --    5.00  37.00-180.00  356
  3  ω   -185.00  -6.00   0.50    5.48    --  -95.70  49.00 -17.48  358
  4  ω   -185.00  -6.00   0.50    5.48    --  -95.70  46.00 150.00  358
  5  ω   -185.00  -6.00   0.50    5.48    --  -95.70  55.00-104.90  358
  6  ω   -185.00  -6.00   0.50    5.48    --  -95.70  55.00-104.90  358
  7  ω   -185.00  -6.00   0.50    5.48    --  -95.70  54.00  89.06  358
  8  ω   -185.00  -6.00   0.50    5.48    --  -95.70  38.00-140.93  358
  9  ω   -185.00  -6.00   0.50    5.48    --  -95.70  55.00  41.60  358
 10  ω   -185.00  -6.00   0.50    5.48    --  -95.70  46.00 150.00  358
 11  ω   -185.00  -6.00   0.50    5.48    --  -95.70  52.00 140.44  358
 12  ω   -185.00  -6.00   0.50    5.48    --  -95.70  55.00 -37.38  358
 13  ω    -89.00  89.00   0.50    1.37    --    0.00  18.00  60.00  356
 14  ω    -89.00  89.00   0.50    1.37    --    0.00  46.00-180.00  356
 15  ω   -185.00  -6.00   0.50    5.48    --  -95.70   0.00 -90.00  358
 16  ω   -185.00 -74.00   0.50    5.48    --  -95.70  46.00  60.00  222
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0180777000
_diffrn_orient_matrix_UB_12      0.0364390000
_diffrn_orient_matrix_UB_13      0.0800177000
_diffrn_orient_matrix_UB_21      0.1837785000
_diffrn_orient_matrix_UB_22      -0.0682352000
_diffrn_orient_matrix_UB_23      0.0047537000
_diffrn_orient_matrix_UB_31      0.0445926000
_diffrn_orient_matrix_UB_32      0.2667297000
_diffrn_orient_matrix_UB_33      -0.0098369000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5133
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.627
_diffrn_reflns_theta_min         4.634
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.954
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         5133
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0475
_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)+(0.0808P)²+0.2122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1412
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4535
_reflns_number_total             5133
_reflns_threshold_expression     'I > 2σ(I)'
_twin_special_details
;
Component 2 rotated by 179.9170° 
around [-0.00 0.00 1.00] (reciprocal) or [0.27 -0.00 0.96] (direct)
;
_cod_data_source_file            d4ob01573h2.cif
_cod_data_source_block           exp_867_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 7160210--7160217.cif.'
_cod_database_code               7160213
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C4H2N6S2
_chemical_oxdiff_usercomment     200K
_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.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.620(2)
 0.380(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 C7-C8 \\sim C7A-C8A
 with sigma of 0.02
4. Rigid bond restraints
 C8A, C7A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Uiso/Uaniso restraints and constraints
Uanis(C8A) = Uanis(S1)
6. Others
 Sof(N1A)=Sof(N2A)=Sof(C7A)=Sof(S1A)=Sof(C8A)=Sof(H8A)=1-FVAR(1)
 Sof(S1)=Sof(C8)=Sof(H8)=Sof(N1)=Sof(N2)=Sof(C7)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C6(H6), C4(H4), C3(H3), C2(H2), C8A(H8A)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.812
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.0838(2) 0.8809(3) 0.58589(5) 0.0537(4) Uani 0.726(5) 1 d . . P A 1
C8 C 0.1718(17) 0.509(3) 0.6602(8) 0.146(8) Uani 0.726(5) 1 d D . P A 1
H8 H 0.210254 0.353538 0.675569 0.175 Uiso 0.726(5) 1 calc R U P A 1
N1 N 0.2212(5) 0.5702(11) 0.4849(2) 0.0451(9) Uani 0.726(5) 1 d . . P A 1
N2 N 0.2349(4) 0.4663(8) 0.54480(18) 0.0462(9) Uani 0.726(5) 1 d . . P A 1
C1 C 0.2949(3) 0.4393(5) 0.43335(12) 0.0505(7) Uani 1 1 d . . . . .
C7 C 0.1696(9) 0.5974(10) 0.5956(3) 0.0437(13) Uani 0.726(5) 1 d D . P A 1
C5 C 0.4463(4) 0.1273(7) 0.38472(18) 0.0693(9) Uani 1 1 d . . . . .
H5 H 0.502751 -0.022626 0.389376 0.083 Uiso 1 1 calc R U . . .
C6 C 0.3764(3) 0.2215(6) 0.44050(15) 0.0622(8) Uani 1 1 d . . . . .
H6 H 0.384340 0.136654 0.483696 0.075 Uiso 1 1 calc R U . . .
C4 C 0.4339(3) 0.2519(7) 0.32184(15) 0.0707(10) Uani 1 1 d . . . . .
H4 H 0.482946 0.187773 0.283511 0.085 Uiso 1 1 calc R U . . .
C3 C 0.3514(4) 0.4667(7) 0.31473(15) 0.0703(9) Uani 1 1 d . . . . .
H3 H 0.342757 0.551039 0.271427 0.084 Uiso 1 1 calc R U . . .
C2 C 0.2808(4) 0.5609(6) 0.37017(14) 0.0592(7) Uani 1 1 d . . . . .
H2 H 0.222489 0.709342 0.365027 0.071 Uiso 1 1 calc R U . . .
N1A N 0.2466(15) 0.452(3) 0.5085(9) 0.067(4) Uani 0.274(5) 1 d . . P A 2
N2A N 0.1874(17) 0.646(3) 0.5090(8) 0.072(4) Uani 0.274(5) 1 d . . P A 2
C7A C 0.144(3) 0.681(3) 0.5816(9) 0.052(4) Uani 0.274(5) 1 d D U P A 2
S1A S 0.1717(5) 0.5156(10) 0.6546(3) 0.0612(13) Uani 0.274(5) 1 d . . P A 2
N4 N 0.1032(3) 0.6963(5) 0.70377(11) 0.0662(8) Uani 1 1 d . . . . .
N3 N 0.0522(3) 0.8915(5) 0.67066(12) 0.0677(7) Uani 1 1 d . . . . .
C8A C 0.082(3) 0.886(4) 0.6021(9) 0.0537(4) Uani 0.274(5) 1 d D U P A 2
H8A H 0.058462 1.019728 0.571469 0.064 Uiso 0.274(5) 1 calc R U P A 2
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'
N N 0.0311 0.0180 '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
N3 S1 C7 92.1(2) . . ?
C7 C8 N4 107.6(11) . . ?
N2 N1 C1 113.6(5) . . ?
N1 N2 C7 113.7(5) . . ?
C6 C1 N1 128.3(3) . . ?
C6 C1 C2 120.2(2) . . ?
C6 C1 N1A 97.0(6) . . ?
C2 C1 N1 111.5(3) . . ?
C2 C1 N1A 142.8(7) . . ?
C8 C7 S1 113.4(8) . . ?
C8 C7 N2 120.2(8) . . ?
N2 C7 S1 126.4(4) . . ?
C6 C5 C4 119.8(3) . . ?
C1 C6 C5 119.7(3) . . ?
C3 C4 C5 120.3(3) . . ?
C4 C3 C2 120.1(3) . . ?
C3 C2 C1 119.9(3) . . ?
N2A N1A C1 101.5(17) . . ?
N1A N2A C7A 105.7(16) . . ?
N2A C7A S1A 133.7(12) . . ?
C8A C7A N2A 122.3(15) . . ?
C8A C7A S1A 103.7(13) . . ?
N4 S1A C7A 97.9(6) . . ?
N3 N4 C8 115.3(6) . . ?
N3 N4 S1A 111.3(2) . . ?
N4 N3 S1 111.6(2) . . ?
N4 N3 C8A 111.8(11) . . ?
C7A C8A N3 115.1(19) . . ?
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
S1 C7 1.722(5) . ?
S1 N3 1.682(2) . ?
C8 C7 1.334(14) . ?
C8 N4 1.489(15) . ?
N1 N2 1.281(6) . ?
N1 C1 1.420(5) . ?
N2 C7 1.376(7) . ?
C1 C6 1.378(4) . ?
C1 C2 1.382(4) . ?
C1 N1A 1.546(19) . ?
C5 C6 1.378(4) . ?
C5 C4 1.385(5) . ?
C4 C3 1.367(5) . ?
C3 C2 1.376(4) . ?
N1A N2A 1.18(2) . ?
N2A C7A 1.49(2) . ?
C7A S1A 1.671(17) . ?
C7A C8A 1.33(2) . ?
S1A N4 1.530(7) . ?
N4 N3 1.298(4) . ?
N3 C8A 1.368(16) . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.620(2) 5844 9741 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.380(2) 5869 9741 nmt -1.0004 -0.0012 -0.0006 0.0013 -0.9983 -0.0000 0.5720
-0.0046 1.0006
