#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:57:08 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299067 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160211.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_7160211
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         'C4 H2 N6 S2'
_chemical_formula_sum            'C4 H2 N6 S2'
_chemical_formula_weight         198.24
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-12
_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                 95.154(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.4717(3)
_cell_length_b                   9.3558(5)
_cell_length_c                   7.3148(4)
_cell_measurement_reflns_used    2786
_cell_measurement_temperature    98.8(6)
_cell_measurement_theta_max      31.0690
_cell_measurement_theta_min      3.5250
_cell_volume                     372.95(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      98.8(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  64.00   0.50    0.24    --    5.68  35.00  30.00  142
  2  ω    -32.00  15.00   0.50    0.24    --    5.68 -35.00-126.00   94
  3  ω    -66.00 -40.00   0.50    0.24    --    5.68 -37.00-180.00   52
  4  ω    -19.00  18.00   0.50    0.24    --    5.68 -37.00-180.00   74
  5  ω    -14.00  36.00   0.50    0.24    --    5.68 -99.00-180.00  100
  6  ω    -61.00 -35.00   0.50    0.05    --   -5.53 -35.00-126.00   52
  7  ω      1.00  48.00   0.50    0.05    --   -5.53  35.00  30.00   94
  8  ω    -10.00  24.00   0.50    0.05    --   -5.53 -99.00 -90.00   68
  9  ω    -18.00   7.00   0.50    0.05    --   -5.53 -99.00-120.00   50
 10  ω     -6.00  26.00   0.50    0.05    --   -5.53 -99.00 150.00   64
 11  ω     52.00  79.00   0.50    0.05    --    5.84  37.00 150.00   54
 12  ω      0.00  47.00   0.50    0.05    --    5.84  37.00 150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0972462000
_diffrn_orient_matrix_UB_12      0.0227044000
_diffrn_orient_matrix_UB_13      0.0641433000
_diffrn_orient_matrix_UB_21      -0.0657011000
_diffrn_orient_matrix_UB_22      -0.0248910000
_diffrn_orient_matrix_UB_23      0.0729515000
_diffrn_orient_matrix_UB_31      0.0565317000
_diffrn_orient_matrix_UB_32      -0.0679188000
_diffrn_orient_matrix_UB_33      -0.0052798000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5465
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         3.544
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
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    1.765
_exptl_crystal_description       block
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         756
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0218
_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)+(0.0295P)²+0.0164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0545
_refine_ls_wR_factor_ref         0.0569
_reflns_Friedel_coverage         0.000
_reflns_number_gt                683
_reflns_number_total             756
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01573h2.cif
_cod_data_source_block           exp_2589_auto
_cod_depositor_comments
'Adding full bibliography for 7160210--7160217.cif.'
_cod_database_code               7160211
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C4H2N8S2
_chemical_oxdiff_usercomment     99K
_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.
;
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C1, S002
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Others
 Sof(S002)=Sof(C0)=Sof(H0)=Sof(C1)=Sof(N1)=1-FVAR(1)
 Sof(S001)=Sof(N005)=Sof(C006)=Sof(C2)=Sof(H2)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C0(H0), C2(H2)
;
_shelx_res_file
;
TITL exp_2589_auto_a.res in P2(1)/c
    exp_2589_auto.res
    created by SHELXL-2018/3 at 16:42:55 on 12-Dec-2023
REM Old TITL exp_2589_auto_a.res in P2(1)
REM SHELXT solution in P2(1)/c: R1 0.177, Rweak 0.010, Alpha 0.042
REM <I/s> 0.177 for 54 systematic absences, Orientation as input
REM Formula found by SHELXT: N2 S
CELL 0.71073 5.4717 9.3558 7.3148 90 95.154 90
ZERR 2 0.0003 0.0005 0.0004 0 0.005 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N S
UNIT 8 4 12 4
DELU 0.005 0.005 C1 S002

L.S. 4
PLAN  2
TEMP -174
BOND
list 4
fmap 2
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\exp_2589_auto.hkl">
REM </olex2.extras>

WGHT    0.029500    0.016400
FVAR       0.76341   0.57532
PART 1
S001  4    0.502491    0.204452    0.527326    21.00000    0.02157    0.01594 =
         0.02398   -0.00181    0.00429   -0.00153
PART 2
S002  4    0.906318    0.341250    0.656368   -21.00000    0.01662    0.02384 =
         0.02525   -0.00061    0.00086   -0.00316
PART 0
N003  3    0.727310    0.097792    0.618233    11.00000    0.02941    0.02037 =
         0.02680    0.00275    0.00510    0.00379
N004  3    0.924272    0.166850    0.679739    11.00000    0.02704    0.02524 =
         0.02789    0.00409    0.00383    0.00423
PART 1
N005  3    0.608143    0.494703    0.539138    21.00000    0.01983    0.01687 =
         0.01840    0.00138    0.00311    0.00105
C006  1    0.679008    0.353009    0.579592    21.00000    0.01019    0.01789 =
         0.01665   -0.00237   -0.00160   -0.00235
PART 2
C0    1    0.541502    0.191419    0.553384   -21.00000    0.04853    0.04655 =
         0.03323   -0.01567    0.00947   -0.02518
AFIX  43
H0    2    0.382155    0.159456    0.509468   -21.00000   -1.20000
AFIX   0
PART 1
C2    1    0.887205    0.313170    0.655979    21.00000    0.02675    0.05211 =
         0.03497   -0.00850    0.00680   -0.01746
AFIX  43
H2    2    1.011189    0.380444    0.694827    21.00000   -1.20000
AFIX   0
PART 2
C1    1    0.604135    0.330021    0.557511   -21.00000    0.00523    0.02622 =
         0.01191   -0.00208   -0.00425    0.00032
N1    3    0.447172    0.440459    0.496286   -21.00000    0.02089    0.02215 =
         0.01980   -0.00008    0.00317   -0.00356
HKLF 4




REM  exp_2589_auto_a.res in P2(1)/c
REM wR2 = 0.0569, GooF = S = 1.052, Restrained GooF = 1.056 for all data
REM R1 = 0.0218 for 683 Fo > 4sig(Fo) and 0.0257 for all 756 data
REM 92 parameters refined using 1 restraints

END

WGHT      0.0295      0.0164

REM Highest difference peak  0.170,  deepest hole -0.186,  1-sigma level  0.042
Q1    1   1.0905  0.3577  0.7152  11.00000  0.05    0.17
Q2    1   1.0759  0.1212  0.6557  11.00000  0.05    0.14
;
_shelx_res_checksum              46502
_olex2_exptl_crystal_mounting_method Cryoloop
_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 1.341
_oxdiff_exptl_absorpt_empirical_full_min 0.803
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.5025(5) 0.2045(2) 0.5273(3) 0.0204(3) Uani 0.575(2) 1 d . . P A 1
S002 S 0.9063(6) 0.3412(5) 0.6564(4) 0.0220(4) Uani 0.425(2) 1 d . U P A 2
N003 N 0.7273(2) 0.09779(10) 0.61823(13) 0.0254(3) Uani 1 1 d . . . . .
N004 N 0.92427(19) 0.16685(10) 0.67974(14) 0.0266(3) Uani 1 1 d . . . . .
N005 N 0.6081(4) 0.4947(3) 0.5391(3) 0.0183(5) Uani 0.575(2) 1 d . . P A 1
C006 C 0.6790(7) 0.3530(6) 0.5796(7) 0.0151(8) Uani 0.575(2) 1 d . . P A 1
C0 C 0.542(3) 0.1914(16) 0.5534(17) 0.042(4) Uani 0.425(2) 1 d . . P A 2
H0 H 0.382155 0.159456 0.509468 0.051 Uiso 0.425(2) 1 calc R U P A 2
C2 C 0.887(2) 0.3132(10) 0.6560(15) 0.038(4) Uani 0.575(2) 1 d . . P A 1
H2 H 1.011189 0.380444 0.694827 0.045 Uiso 0.575(2) 1 calc R U P A 1
C1 C 0.6041(11) 0.3300(8) 0.5575(9) 0.0148(11) Uani 0.425(2) 1 d . U P A 2
N1 N 0.4472(7) 0.4405(4) 0.4963(4) 0.0209(7) Uani 0.425(2) 1 d . . P A 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S001 0.0216(5) 0.0159(4) 0.0240(5) -0.0018(3) 0.0043(5) -0.0015(3)
S002 0.0166(8) 0.0238(8) 0.0253(7) -0.0006(4) 0.0009(5) -0.0032(8)
N003 0.0294(6) 0.0204(5) 0.0268(6) 0.0028(4) 0.0051(5) 0.0038(4)
N004 0.0270(6) 0.0252(6) 0.0279(6) 0.0041(4) 0.0038(5) 0.0042(4)
N005 0.0198(14) 0.0169(12) 0.0184(9) 0.0014(8) 0.0031(8) 0.0010(9)
C006 0.010(2) 0.0179(15) 0.0166(17) -0.0024(11) -0.0016(16) -0.0024(16)
C0 0.049(8) 0.047(7) 0.033(5) -0.016(4) 0.009(4) -0.025(5)
C2 0.027(3) 0.052(7) 0.035(3) -0.008(3) 0.0068(18) -0.017(3)
C1 0.005(3) 0.026(3) 0.0119(19) -0.0021(15) -0.0043(19) 0.0003(19)
N1 0.0209(18) 0.0222(17) 0.0198(13) -0.0001(11) 0.0032(11) -0.0036(17)
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'
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
N003 S001 C006 90.9(2) . . ?
N004 S002 C1 91.7(3) . . ?
N004 N003 S001 113.41(12) . . ?
N004 N003 C0 111.2(7) . . ?
N003 N004 S002 114.66(16) . . ?
N003 N004 C2 109.8(5) . . ?
N005 N005 C006 113.4(4) 3_666 . ?
N005 C006 S001 125.3(3) . . ?
C2 C006 S001 108.8(6) . . ?
C2 C006 N005 125.8(5) . . ?
C1 C0 N003 115.0(12) . . ?
C006 C2 N004 117.1(9) . . ?
C0 C1 S002 107.3(7) . . ?
C0 C1 N1 124.2(7) . . ?
N1 C1 S002 128.5(4) . . ?
N1 N1 C1 112.1(5) 3_666 . ?
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
S001 N003 1.675(2) . ?
S001 C006 1.716(5) . ?
S002 N004 1.643(4) . ?
S002 C1 1.747(8) . ?
N003 N004 1.3016(15) . ?
N003 C0 1.393(11) . ?
N004 C2 1.392(9) . ?
N005 N005 1.271(5) 3_666 ?
N005 C006 1.405(6) . ?
C006 C2 1.278(13) . ?
C0 C1 1.341(17) . ?
C1 N1 1.392(9) . ?
N1 N1 1.254(6) 3_666 ?
