#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:57:08 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299067 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160214.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_7160214
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           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-03-07
_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                 104.253(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.4747(2)
_cell_length_b                   15.4161(6)
_cell_length_c                   10.5241(4)
_cell_measurement_reflns_used    7269
_cell_measurement_temperature    199.95(10)
_cell_measurement_theta_max      31.0510
_cell_measurement_theta_min      2.6160
_cell_volume                     860.88(6)
_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      199.95(10)
_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 0.869
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00  20.00   0.50    0.53    --    5.68 -53.00-109.00  174
  2  ω    -18.00  38.00   0.50    0.53    --    5.68 -99.00 -30.00  112
  3  ω    -67.00  28.00   0.50    0.53    --    5.68 -77.00 120.00  190
  4  ω    -67.00 -10.00   0.50    0.53    --    5.68 -37.00  30.00  114
  5  ω     -8.00  78.00   0.50    0.53    --    5.68  53.00  34.00  172
  6  ω    -18.00  68.00   0.50    0.53    --   -5.45  37.00 -30.00  172
  7  ω    -79.00   7.00   0.50    0.53    --   -5.45 -37.00 150.00  172
  8  ω    -18.00  27.00   0.50    0.53    --   -5.45 -99.00-120.00   90
  9  ω    -18.00  27.00   0.50    0.53    --   -5.45 -99.00-150.00   90
;
_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      -0.0032700000
_diffrn_orient_matrix_UB_12      0.0232772000
_diffrn_orient_matrix_UB_13      0.0577090000
_diffrn_orient_matrix_UB_21      -0.1200239000
_diffrn_orient_matrix_UB_22      -0.0179727000
_diffrn_orient_matrix_UB_23      -0.0016820000
_diffrn_orient_matrix_UB_31      0.0587734000
_diffrn_orient_matrix_UB_32      -0.0353829000
_diffrn_orient_matrix_UB_33      0.0387695000
_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  0.0286
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9818
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.261
_diffrn_reflns_theta_min         2.642
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70393
_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    1.468
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 889 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2236
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0347
_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)+(0.0521P)²+0.1631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.729
_reflns_number_gt                2044
_reflns_number_total             2236
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01573h2.cif
_cod_data_source_block           exp_2735_autored
_cod_depositor_comments
'Adding full bibliography for 7160210--7160217.cif.'
_cod_database_code               7160214
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C8H6N4S
_chemical_oxdiff_usercomment     '200K, cis_Ph_NN_124N2S'
_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   0.956
_shelx_estimated_absorpt_t_min   0.845
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C7(H7), C4(H4), C8(H8), C5(H5)
;
_shelx_res_file
;
TITL exp_2735_autored_a.res in Cc
    exp_2735_autored.res
    created by SHELXL-2018/3 at 11:13:39 on 07-Mar-2024
REM Old TITL exp_2735_autored in C1
REM SHELXT solution in Cc: R1 0.183, Rweak 0.053, Alpha 0.004
REM <I/s> 0.972 for 35 systematic absences, Orientation as input
REM Flack x = 0.107 ( 0.028 ) from 811 Parsons' quotients
REM Formula found by SHELXT: C8 N1 S
CELL 0.71073 5.4747 15.4161 10.5241 90 104.253 90
ZERR 4 0.0002 0.0006 0.0004 0 0.004 0
LATT -7
SYMM +X,-Y,0.5+Z
SFAC C H N S
UNIT 32 24 16 4

L.S. 4
PLAN  5
SIZE 0.14 0.17 0.53
TEMP -73.2(1)
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\exp_2735_autored.hkl">
REM </olex2.extras>

WGHT    0.052100    0.163100
FVAR       0.81992
S1    4    0.260010    0.571761    0.457459    11.00000    0.02196    0.10559 =
         0.04437   -0.02001    0.00640    0.00043
N2    3    0.651106    0.534207    0.378043    11.00000    0.02861    0.06028 =
         0.04292   -0.00703    0.00860    0.00448
N4    3    0.765690    0.637780    0.674927    11.00000    0.03040    0.06116 =
         0.03589    0.00342    0.00378    0.00046
N3    3    0.771808    0.578034    0.596361    11.00000    0.02351    0.05947 =
         0.03534    0.00204    0.00397    0.00235
N1    3    0.447723    0.515106    0.276366    11.00000    0.03819    0.06390 =
         0.04261   -0.01408    0.00566    0.00036
C3    1    0.578865    0.705549    0.643680    11.00000    0.03459    0.04761 =
         0.03087   -0.00279   -0.00019   -0.00243
C1    1    0.581447    0.566229    0.477640    11.00000    0.02253    0.04353 =
         0.03515    0.00252    0.00509    0.00308
C2    1    0.239627    0.783389    0.696165    11.00000    0.04368    0.05227 =
         0.04632   -0.00881    0.01096   -0.00150
AFIX  43
H2    2    0.120401    0.789765    0.747586    11.00000   -1.20000
AFIX   0
C6    1    0.239064    0.841385    0.595623    11.00000    0.05213    0.04306 =
         0.05086   -0.00319    0.00084   -0.00016
AFIX  43
H6    2    0.120706    0.887604    0.578567    11.00000   -1.20000
AFIX   0
C7    1    0.411458    0.831787    0.520096    11.00000    0.05706    0.05177 =
         0.04286    0.00877    0.00079   -0.01225
AFIX  43
H7    2    0.413891    0.872346    0.452457    11.00000   -1.20000
AFIX   0
C4    1    0.412152    0.716330    0.722311    11.00000    0.04401    0.04692 =
         0.03495   -0.00062    0.00771   -0.00137
AFIX  43
H4    2    0.416367    0.678005    0.793507    11.00000   -1.20000
AFIX   0
C8    1    0.579782    0.763641    0.542508    11.00000    0.04422    0.06103 =
         0.03509    0.00236    0.00656   -0.01102
AFIX  43
H8    2    0.695539    0.756383    0.489297    11.00000   -1.20000
AFIX   0
C5    1    0.235334    0.530262    0.305214    11.00000    0.03209    0.04643 =
         0.04013   -0.00491    0.00217   -0.00182
AFIX  43
H5    2    0.077406    0.519041    0.245770    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_2735_autored_a.res in Cc
REM wR2 = 0.0908, GooF = S = 1.081, Restrained GooF = 1.081 for all data
REM R1 = 0.0347 for 2044 Fo > 4sig(Fo) and 0.0383 for all 2236 data
REM 118 parameters refined using 2 restraints

END

WGHT      0.0521      0.1618

REM Highest difference peak  0.346,  deepest hole -0.169,  1-sigma level  0.046
Q1    1   0.3012  0.6106  0.4117  11.00000  0.05    0.35
Q2    1   0.2229  0.5223  0.4000  11.00000  0.05    0.31
Q3    1   0.3108  0.5188  0.4624  11.00000  0.05    0.23
Q4    1   0.6285  0.5077  0.4397  11.00000  0.05    0.20
Q5    1   0.6149  0.5766  0.3901  11.00000  0.05    0.19
;
_shelx_res_checksum              71087
_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 1.385
_oxdiff_exptl_absorpt_empirical_full_min 0.680
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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 0.26001(10) 0.57176(6) 0.45746(7) 0.0576(2) Uani 1 1 d . . . . .
N2 N 0.6511(4) 0.53421(17) 0.3780(2) 0.0440(5) Uani 1 1 d . . . . .
N4 N 0.7657(4) 0.63778(16) 0.6749(2) 0.0433(5) Uani 1 1 d . . . . .
N3 N 0.7718(4) 0.57803(14) 0.5964(2) 0.0400(5) Uani 1 1 d . . . . .
N1 N 0.4477(4) 0.51511(17) 0.2764(2) 0.0490(5) Uani 1 1 d . . . . .
C3 C 0.5789(5) 0.70555(16) 0.6437(2) 0.0391(5) Uani 1 1 d . . . . .
C1 C 0.5814(4) 0.56623(15) 0.4776(2) 0.0341(5) Uani 1 1 d . . . . .
C2 C 0.2396(6) 0.78339(17) 0.6962(3) 0.0474(6) Uani 1 1 d . . . . .
H2 H 0.120401 0.789765 0.747586 0.057 Uiso 1 1 calc R U . . .
C6 C 0.2391(6) 0.84138(18) 0.5956(3) 0.0508(7) Uani 1 1 d . . . . .
H6 H 0.120706 0.887604 0.578567 0.061 Uiso 1 1 calc R U . . .
C7 C 0.4115(6) 0.8318(2) 0.5201(3) 0.0526(7) Uani 1 1 d . . . . .
H7 H 0.413891 0.872346 0.452457 0.063 Uiso 1 1 calc R U . . .
C4 C 0.4122(5) 0.71633(17) 0.7223(3) 0.0423(5) Uani 1 1 d . . . . .
H4 H 0.416367 0.678005 0.793507 0.051 Uiso 1 1 calc R U . . .
C8 C 0.5798(6) 0.76364(19) 0.5425(3) 0.0473(6) Uani 1 1 d . . . . .
H8 H 0.695539 0.756383 0.489297 0.057 Uiso 1 1 calc R U . . .
C5 C 0.2353(5) 0.53026(16) 0.3052(3) 0.0407(5) Uani 1 1 d . . . . .
H5 H 0.077406 0.519041 0.245770 0.049 Uiso 1 1 calc R U . . .
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
S1 0.0220(3) 0.1056(6) 0.0444(3) -0.0200(4) 0.0064(2) 0.0004(3)
N2 0.0286(10) 0.0603(13) 0.0429(11) -0.0070(10) 0.0086(8) 0.0045(9)
N4 0.0304(10) 0.0612(13) 0.0359(10) 0.0034(9) 0.0038(8) 0.0005(9)
N3 0.0235(9) 0.0595(12) 0.0353(10) 0.0020(9) 0.0040(8) 0.0023(8)
N1 0.0382(12) 0.0639(14) 0.0426(11) -0.0141(10) 0.0057(9) 0.0004(9)
C3 0.0346(12) 0.0476(12) 0.0309(11) -0.0028(9) -0.0002(9) -0.0024(10)
C1 0.0225(10) 0.0435(11) 0.0352(11) 0.0025(9) 0.0051(9) 0.0031(8)
C2 0.0437(14) 0.0523(15) 0.0463(14) -0.0088(12) 0.0110(11) -0.0015(11)
C6 0.0521(16) 0.0431(14) 0.0509(16) -0.0032(11) 0.0008(12) -0.0002(11)
C7 0.0571(16) 0.0518(15) 0.0429(13) 0.0088(12) 0.0008(12) -0.0122(13)
C4 0.0440(13) 0.0469(13) 0.0349(11) -0.0006(10) 0.0077(10) -0.0014(11)
C8 0.0442(14) 0.0610(15) 0.0351(12) 0.0024(12) 0.0066(10) -0.0110(12)
C5 0.0321(11) 0.0464(13) 0.0401(12) -0.0049(10) 0.0022(9) -0.0018(9)
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
C5 S1 C1 86.52(13) . . ?
C1 N2 N1 111.6(2) . . ?
N3 N4 C3 121.2(2) . . ?
N4 N3 C1 122.9(2) . . ?
C5 N1 N2 112.4(2) . . ?
C4 C3 N4 119.0(2) . . ?
C4 C3 C8 120.5(3) . . ?
C8 C3 N4 120.3(2) . . ?
N2 C1 S1 114.44(18) . . ?
N2 C1 N3 117.3(2) . . ?
N3 C1 S1 127.24(18) . . ?
C4 C2 C6 120.5(3) . . ?
C7 C6 C2 119.8(3) . . ?
C8 C7 C6 120.3(3) . . ?
C2 C4 C3 119.3(2) . . ?
C7 C8 C3 119.5(3) . . ?
N1 C5 S1 115.0(2) . . ?
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 C1 1.722(2) . ?
S1 C5 1.699(3) . ?
N2 N1 1.373(3) . ?
N2 C1 1.298(3) . ?
N4 N3 1.244(3) . ?
N4 C3 1.442(3) . ?
N3 C1 1.428(3) . ?
N1 C5 1.293(4) . ?
C3 C4 1.385(4) . ?
C3 C8 1.392(4) . ?
C2 C6 1.385(4) . ?
C2 C4 1.382(4) . ?
C6 C7 1.383(5) . ?
C7 C8 1.379(5) . ?
