#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:57:08 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299067 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160212.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_7160212
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 H8 N4 S2'
_chemical_formula_sum            'C8 H8 N4 S2'
_chemical_formula_weight         224.30
_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             2024-06-13
_audit_creation_method
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2024-07-16 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.281(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3127(8)
_cell_length_b                   5.0803(2)
_cell_length_c                   10.6479(7)
_cell_measurement_reflns_used    1537
_cell_measurement_temperature    292.95(10)
_cell_measurement_theta_max      28.1710
_cell_measurement_theta_min      2.2560
_cell_volume                     491.27(7)
_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 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.95(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 0.864
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  92.00   0.50    0.11    --   20.67  61.00-106.00  200
  2  ω      1.00  28.00   0.50    0.11    --  -20.52 -99.00-120.00   54
  3  ω      9.00  35.00   0.50    0.11    --  -20.52 -99.00 -60.00   52
  4  ω    -18.00  35.00   0.50    0.11    --  -20.52 -99.00 -30.00  106
  5  ω    -48.00  36.00   0.50    0.11    --   20.67 -61.00 114.00  168
  6  ω     58.00  91.00   0.50    0.05    --   20.83 178.00-180.00   66
  7  ω    -66.00 -41.00   0.50    0.05    --  -20.67 -61.00 114.00   50
;
_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      -0.0467787000
_diffrn_orient_matrix_UB_12      0.0999940000
_diffrn_orient_matrix_UB_13      -0.0453779000
_diffrn_orient_matrix_UB_21      -0.0365177000
_diffrn_orient_matrix_UB_22      0.0072834000
_diffrn_orient_matrix_UB_23      0.0419899000
_diffrn_orient_matrix_UB_31      0.0509111000
_diffrn_orient_matrix_UB_32      0.0971473000
_diffrn_orient_matrix_UB_33      0.0436016000
_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  0.0290
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3086
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.820
_diffrn_reflns_theta_min         2.265
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69775
_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    1.516
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0366
_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)+(0.0543P)²+0.0883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.000
_reflns_number_gt                931
_reflns_number_total             1107
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01573h2.cif
_cod_data_source_block           exp_2887_auto
_cod_depositor_comments
'Adding full bibliography for 7160210--7160217.cif.'
_cod_original_cell_volume        491.27(6)
_cod_database_code               7160212
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_chemical_oxdiff_usercomment     293K
_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   0.966
_shelx_estimated_absorpt_t_min   0.847
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_file
;
TITL exp_2887_auto_a.res in P2(1)/n
    exp_2887_auto.res
    created by SHELXL-2018/3 at 18:01:04 on 13-Jun-2024
REM Old TITL exp_2887_auto in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.114, Rweak 0.301, Alpha 0.017
REM <I/s> 0.229 for 118 systematic absences, Orientation as input
REM Formula found by SHELXT: C7 N5 Cl
CELL 0.71073 10.3127 5.0803 10.6479 90 118.281 90
ZERR 2 0.0008 0.0002 0.0007 0 0.009 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N S
UNIT 16 16 8 4

L.S. 4
PLAN  5
SIZE 0.07 0.29 0.34
TEMP 19.8(1)
HTAB
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\exp_2887_auto.hkl">
REM </olex2.extras>

WGHT    0.054300    0.088300
FVAR       1.34998
S2    4    0.398557    0.388065    0.294913    11.00000    0.03729    0.03797 =
         0.04014    0.00600    0.02183    0.00347
N6    3    0.559682    0.010176    0.496652    11.00000    0.03625    0.03484 =
         0.03477    0.00174    0.01973    0.00029
N5    3    0.666736    0.240767    0.378588    11.00000    0.03849    0.04658 =
         0.04992    0.00965    0.02646    0.00314
C1    1    0.552953    0.199006    0.398956    11.00000    0.03455    0.03377 =
         0.03071   -0.00033    0.01738    0.00047
C3    1    0.494322    0.533147    0.218225    11.00000    0.04530    0.03225 =
         0.03378   -0.00144    0.02242   -0.00623
C4    1    0.632638    0.428925    0.276146    11.00000    0.04560    0.04416 =
         0.05029    0.00624    0.03178   -0.00240
AFIX  43
H4    2    0.700454    0.483467    0.247218    11.00000   -1.20000
AFIX   0
C7    1    0.428438    0.737548    0.103409    11.00000    0.05777    0.03951 =
         0.04104    0.00665    0.02177   -0.00362
AFIX 137
H7A   2    0.343609    0.665726    0.023015    11.00000   -1.50000
H7B   2    0.499825    0.790049    0.074573    11.00000   -1.50000
H7C   2    0.399690    0.887759    0.139115    11.00000   -1.50000
AFIX   0
HKLF 4




REM  exp_2887_auto_a.res in P2(1)/n
REM wR2 = 0.1021, GooF = S = 1.049, Restrained GooF = 1.049 for all data
REM R1 = 0.0366 for 931 Fo > 4sig(Fo) and 0.0448 for all 1107 data
REM 65 parameters refined using 0 restraints

END

WGHT      0.0543      0.0883

REM Instructions for potential hydrogen bonds
EQIV $2 -x+3/2, y+1/2, -z+1/2
HTAB C4 N5_$2

REM Highest difference peak  0.215,  deepest hole -0.276,  1-sigma level  0.062
Q1    1   0.4959  0.3304  0.3834  11.00000  0.05    0.22
Q2    1   0.4265  0.4123  0.2159  11.00000  0.05    0.21
Q3    1   0.3245  0.8490  0.0742  11.00000  0.05    0.20
Q4    1   0.2785  0.3691  0.1862  11.00000  0.05    0.19
Q5    1   0.4926  0.5887  0.0284  11.00000  0.05    0.19
;
_shelx_res_checksum              94141
_olex2_exptl_crystal_mounting_method 'MiTeGen Micromount'
_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 2.031
_oxdiff_exptl_absorpt_empirical_full_min 0.511
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
S2 S 0.39856(6) 0.38806(9) 0.29491(5) 0.0370(2) Uani 1 1 d . . . . .
N6 N 0.55968(17) 0.0102(3) 0.49665(16) 0.0341(4) Uani 1 1 d . . . . .
N5 N 0.66674(19) 0.2408(3) 0.37859(19) 0.0428(4) Uani 1 1 d . . . . .
C1 C 0.5530(2) 0.1990(4) 0.39896(18) 0.0322(4) Uani 1 1 d . . . . .
C3 C 0.4943(2) 0.5331(4) 0.21822(19) 0.0356(5) Uani 1 1 d . . . . .
C4 C 0.6326(3) 0.4289(4) 0.2761(2) 0.0430(5) Uani 1 1 d . . . . .
H4 H 0.700454 0.483467 0.247218 0.052 Uiso 1 1 calc R U . . .
C7 C 0.4284(3) 0.7375(4) 0.1034(2) 0.0468(5) Uani 1 1 d . . . . .
H7A H 0.343609 0.665726 0.023015 0.070 Uiso 1 1 calc R U . . .
H7B H 0.499825 0.790049 0.074573 0.070 Uiso 1 1 calc R U . . .
H7C H 0.399690 0.887759 0.139115 0.070 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
S2 0.0373(4) 0.0380(3) 0.0401(3) 0.00600(18) 0.0218(3) 0.00347(18)
N6 0.0363(10) 0.0348(8) 0.0348(8) 0.0017(6) 0.0197(7) 0.0003(7)
N5 0.0385(11) 0.0466(10) 0.0499(10) 0.0097(8) 0.0265(9) 0.0031(7)
C1 0.0346(11) 0.0338(9) 0.0307(9) -0.0003(7) 0.0174(8) 0.0005(7)
C3 0.0453(12) 0.0323(10) 0.0338(9) -0.0014(7) 0.0224(9) -0.0062(8)
C4 0.0456(13) 0.0442(11) 0.0503(12) 0.0062(9) 0.0318(11) -0.0024(9)
C7 0.0578(15) 0.0395(11) 0.0410(11) 0.0066(8) 0.0218(11) -0.0036(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
C3 S2 C1 88.89(9) . . ?
N6 N6 C1 113.04(19) 3_656 . ?
C1 N5 C4 109.54(18) . . ?
N6 C1 S2 124.33(15) . . ?
N5 C1 S2 115.35(14) . . ?
N5 C1 N6 120.31(17) . . ?
C4 C3 S2 109.39(15) . . ?
C4 C3 C7 127.61(19) . . ?
C7 C3 S2 122.99(17) . . ?
C3 C4 N5 116.82(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
S2 C1 1.7360(19) . ?
S2 C3 1.717(2) . ?
N6 N6 1.270(3) 3_656 ?
N6 C1 1.392(2) . ?
N5 C1 1.308(2) . ?
N5 C4 1.365(3) . ?
C3 C4 1.364(3) . ?
C3 C7 1.499(3) . ?
