#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:57:08 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299067 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160216.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_7160216
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      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-02-28
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.9619(3)
_cell_length_b                   8.0466(6)
_cell_length_c                   18.1430(11)
_cell_measurement_reflns_used    3993
_cell_measurement_temperature    200.00(14)
_cell_measurement_theta_max      29.9870
_cell_measurement_theta_min      2.2210
_cell_volume                     870.37(9)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  65.00   0.50    0.59    --   -5.45  37.00  60.00  164
  2  ω      8.00  33.00   0.50    0.59    --    5.68  71.00  64.00   50
  3  ω     -6.00  41.00   0.50    0.59    --    5.68  50.00-122.00   94
  4  ω    -14.00  37.00   0.50    0.59    --    5.68 -99.00  60.00  102
;
_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      -0.0951784000
_diffrn_orient_matrix_UB_12      -0.0094070000
_diffrn_orient_matrix_UB_13      0.0230870000
_diffrn_orient_matrix_UB_21      0.0010489000
_diffrn_orient_matrix_UB_22      -0.0868613000
_diffrn_orient_matrix_UB_23      -0.0064567000
_diffrn_orient_matrix_UB_31      0.0714772000
_diffrn_orient_matrix_UB_32      -0.0112059000
_diffrn_orient_matrix_UB_33      0.0308921000
_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  0.0359
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6333
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.875
_diffrn_reflns_theta_min         2.245
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14391
_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    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.88
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 618 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0463
_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)+(0.0733P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1183
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.756
_reflns_number_gt                1810
_reflns_number_total             2249
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01573h2.cif
_cod_data_source_block           exp_2732_auto
_cod_depositor_comments
'Adding full bibliography for 7160210--7160217.cif.'
_cod_database_code               7160216
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C7H6N4S
_chemical_oxdiff_usercomment     '200K, cis_Ph_NN_123N2S'
_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   0.947
_shelx_estimated_absorpt_t_min   0.763
_reflns_odcompleteness_completeness 99.91
_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:
 C10(H10), C5(H5), C6(H6), C4(H4), C3(H3), C2(H2)
;
_shelx_res_file
;
TITL exp_2732_auto_a.res in P2(1)2(1)2(1)
    exp_2732_auto.res
    created by SHELXL-2018/3 at 12:16:55 on 28-Feb-2024
REM Old TITL exp_2732_auto in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1): R1 0.129, Rweak 0.023, Alpha 0.001
REM <I/s> 2.256 for 19 systematic absences, Orientation as input
REM Flack x = 0.003 ( 0.051 ) from 595 Parsons' quotients
REM Formula found by SHELXT: C2 N11 S
CELL 0.71073 5.9619 8.0466 18.143 90 90 90
ZERR 4 0.0003 0.0006 0.0011 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H N S
UNIT 32 24 16 4

L.S. 4
PLAN  1
SIZE 0.17 0.19 0.88
TEMP -73.15(14)
fmap 2
ACTA
OMIT 0 2 1
OMIT 1 1 0
REM <olex2.extras>
REM <HklSrc "%.\\exp_2732_auto.hkl">
REM </olex2.extras>

WGHT    0.073300
FVAR       3.72927
S13   4    0.800615    0.357457    0.590100    11.00000    0.02749    0.04601 =
         0.05814    0.01041   -0.00091    0.00010
N8    3    0.322229    0.303482    0.590515    11.00000    0.02974    0.05508 =
         0.06446    0.00544   -0.00011    0.00195
N11   3    0.702052    0.622123    0.527797    11.00000    0.05453    0.04757 =
         0.06215    0.01368   -0.00183    0.00051
N12   3    0.874875    0.537928    0.550510    11.00000    0.03888    0.04887 =
         0.06617    0.00845    0.00534   -0.00324
N7    3    0.318258    0.174207    0.627992    11.00000    0.03147    0.05479 =
         0.08923    0.01023    0.00366    0.00107
C10   1    0.505011    0.544962    0.541539    11.00000    0.03909    0.05024 =
         0.05241    0.00415   -0.00600    0.00930
AFIX  43
H10   2    0.364870    0.591870    0.527820    11.00000   -1.20000
AFIX   0
C5    1    0.835343   -0.070795    0.657875    11.00000    0.05160    0.05094 =
         0.05680    0.00771    0.00168    0.00794
AFIX  43
H5    2    0.924443   -0.150052    0.632401    11.00000   -1.20000
AFIX   0
C9    1    0.520761    0.396309    0.576176    11.00000    0.02799    0.04848 =
         0.04469   -0.00156   -0.00120    0.00374
C1    1    0.520902    0.110650    0.661763    11.00000    0.03473    0.04481 =
         0.06293    0.01290    0.00502   -0.00501
C6    1    0.644981   -0.007042    0.625164    11.00000    0.04521    0.05131 =
         0.05120    0.00529    0.00153   -0.00101
AFIX  43
H6    2    0.600128   -0.044271    0.577710    11.00000   -1.20000
AFIX   0
C4    1    0.896813   -0.018874    0.728278    11.00000    0.04853    0.05824 =
         0.06293    0.01565   -0.00827   -0.00632
AFIX  43
H4    2    1.030091   -0.060529    0.750241    11.00000   -1.20000
AFIX   0
C3    1    0.764042    0.093363    0.766340    11.00000    0.06210    0.05314 =
         0.05313    0.00251    0.00116   -0.01217
AFIX  43
H3    2    0.802772    0.125407    0.815102    11.00000   -1.20000
AFIX   0
C2    1    0.576217    0.158078    0.733265    11.00000    0.05257    0.05145 =
         0.06792   -0.00198    0.01299   -0.00159
AFIX  43
H2    2    0.484329    0.234965    0.759096    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_2732_auto_a.res in P2(1)2(1)2(1)
REM wR2 = 0.1183, GooF = S = 1.030, Restrained GooF = 1.030 for all data
REM R1 = 0.0463 for 1810 Fo > 4sig(Fo) and 0.0590 for all 2249 data
REM 118 parameters refined using 0 restraints

END

WGHT      0.0734      0.0000

REM Highest difference peak  0.393,  deepest hole -0.185,  1-sigma level  0.073
Q1    1   0.8414  0.4738  0.5896  11.00000  0.05    0.39
;
_shelx_res_checksum              69071
_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 2.881
_oxdiff_exptl_absorpt_empirical_full_min 0.248
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
S13 S 0.80062(12) 0.35746(10) 0.59010(4) 0.0439(2) Uani 1 1 d . . . . .
N8 N 0.3222(4) 0.3035(4) 0.59051(15) 0.0498(6) Uani 1 1 d . . . . .
N11 N 0.7021(5) 0.6221(4) 0.52780(16) 0.0548(7) Uani 1 1 d . . . . .
N12 N 0.8749(5) 0.5379(4) 0.55051(17) 0.0513(7) Uani 1 1 d . . . . .
N7 N 0.3183(5) 0.1742(4) 0.62799(18) 0.0585(8) Uani 1 1 d . . . . .
C10 C 0.5050(6) 0.5450(4) 0.54154(18) 0.0472(8) Uani 1 1 d . . . . .
H10 H 0.364870 0.591870 0.527820 0.057 Uiso 1 1 calc R U . . .
C5 C 0.8353(6) -0.0708(5) 0.65787(18) 0.0531(8) Uani 1 1 d . . . . .
H5 H 0.924443 -0.150052 0.632401 0.064 Uiso 1 1 calc R U . . .
C9 C 0.5208(5) 0.3963(4) 0.57618(16) 0.0404(7) Uani 1 1 d . . . . .
C1 C 0.5209(5) 0.1107(4) 0.66176(19) 0.0475(8) Uani 1 1 d . . . . .
C6 C 0.6450(6) -0.0070(5) 0.62516(17) 0.0492(8) Uani 1 1 d . . . . .
H6 H 0.600128 -0.044271 0.577710 0.059 Uiso 1 1 calc R U . . .
C4 C 0.8968(7) -0.0189(5) 0.7283(2) 0.0566(9) Uani 1 1 d . . . . .
H4 H 1.030091 -0.060529 0.750241 0.068 Uiso 1 1 calc R U . . .
C3 C 0.7640(7) 0.0934(5) 0.7663(2) 0.0561(9) Uani 1 1 d . . . . .
H3 H 0.802772 0.125407 0.815102 0.067 Uiso 1 1 calc R U . . .
C2 C 0.5762(6) 0.1581(5) 0.7333(2) 0.0573(9) Uani 1 1 d . . . . .
H2 H 0.484329 0.234965 0.759096 0.069 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
S13 0.0275(3) 0.0460(4) 0.0581(4) 0.0104(3) -0.0009(3) 0.0001(3)
N8 0.0297(13) 0.0551(16) 0.0645(15) 0.0054(14) -0.0001(13) 0.0020(12)
N11 0.0545(16) 0.0476(15) 0.0622(15) 0.0137(13) -0.0018(14) 0.0005(16)
N12 0.0389(14) 0.0489(18) 0.0662(16) 0.0085(14) 0.0053(13) -0.0032(13)
N7 0.0315(13) 0.0548(18) 0.089(2) 0.0102(15) 0.0037(13) 0.0011(14)
C10 0.0391(16) 0.0502(19) 0.0524(17) 0.0042(14) -0.0060(13) 0.0093(15)
C5 0.052(2) 0.0509(18) 0.0568(17) 0.0077(16) 0.0017(16) 0.0079(16)
C9 0.0280(13) 0.0485(18) 0.0447(14) -0.0016(13) -0.0012(10) 0.0037(12)
C1 0.0347(15) 0.0448(18) 0.0629(19) 0.0129(15) 0.0050(14) -0.0050(14)
C6 0.0452(19) 0.0513(19) 0.0512(17) 0.0053(15) 0.0015(13) -0.0010(15)
C4 0.0485(19) 0.058(2) 0.0629(19) 0.0156(19) -0.0083(16) -0.0063(17)
C3 0.062(2) 0.0531(19) 0.0531(16) 0.0025(15) 0.0012(16) -0.0122(18)
C2 0.053(2) 0.051(2) 0.068(2) -0.0020(19) 0.0130(16) -0.0016(18)
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
N12 S13 C9 92.05(16) . . ?
N7 N8 C9 123.7(3) . . ?
N12 N11 C10 113.0(3) . . ?
N11 N12 S13 112.2(2) . . ?
N8 N7 C1 120.7(3) . . ?
N11 C10 C9 115.5(3) . . ?
C6 C5 C4 120.0(4) . . ?
N8 C9 S13 133.3(2) . . ?
C10 C9 S13 107.3(2) . . ?
C10 C9 N8 119.4(3) . . ?
C6 C1 N7 119.2(3) . . ?
C6 C1 C2 120.8(3) . . ?
C2 C1 N7 119.7(3) . . ?
C1 C6 C5 119.5(3) . . ?
C3 C4 C5 120.2(4) . . ?
C2 C3 C4 119.7(3) . . ?
C3 C2 C1 119.8(3) . . ?
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
S13 N12 1.680(3) . ?
S13 C9 1.716(3) . ?
N8 N7 1.243(4) . ?
N8 C9 1.424(4) . ?
N11 N12 1.300(4) . ?
N11 C10 1.352(5) . ?
N7 C1 1.448(4) . ?
C10 C9 1.354(5) . ?
C5 C6 1.380(5) . ?
C5 C4 1.393(5) . ?
C1 C6 1.373(5) . ?
C1 C2 1.392(5) . ?
C4 C3 1.385(6) . ?
C3 C2 1.373(6) . ?
