#------------------------------------------------------------------------------
#$Date: 2025-04-05 06:57:08 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299067 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160210.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_7160210
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 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             2023-12-12
_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                 109.377(13)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.7758(4)
_cell_length_b                   18.2803(16)
_cell_length_c                   5.4893(7)
_cell_measurement_reflns_used    1535
_cell_measurement_temperature    98.4(8)
_cell_measurement_theta_max      31.0600
_cell_measurement_theta_min      2.2220
_cell_volume                     357.42(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      N~2~
_diffrn_ambient_temperature      98.4(8)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00   5.00   0.50    2.18    --   -5.45 -95.00 -69.00   60
  2  ω    -15.00  12.00   0.50    2.18    --   -5.45 -99.00  30.00   54
  3  ω    -14.00  38.00   0.50    2.18    --    5.68 -99.00  60.00  104
  4  ω    -18.00  20.00   0.50    2.18    --    5.68 -77.00 177.00   76
  5  ω    -67.00 -26.00   0.50    2.18    --    5.68 -77.00 177.00   82
;
_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      0.0837842000
_diffrn_orient_matrix_UB_12      -0.0163575000
_diffrn_orient_matrix_UB_13      0.1229950000
_diffrn_orient_matrix_UB_21      -0.1382435000
_diffrn_orient_matrix_UB_22      -0.0278999000
_diffrn_orient_matrix_UB_23      -0.0334942000
_diffrn_orient_matrix_UB_31      0.1161932000
_diffrn_orient_matrix_UB_32      -0.0213811000
_diffrn_orient_matrix_UB_33      -0.0505284000
_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  0.0244
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2024
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.228
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26602
_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    1.842
_exptl_crystal_description       block
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0311
_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)+(0.0427P)²+0.2186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0793
_reflns_Friedel_coverage         0.000
_reflns_number_gt                651
_reflns_number_total             716
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01573h2.cif
_cod_data_source_block           exp_2588_auto
_cod_depositor_comments
'Adding full bibliography for 7160210--7160217.cif.'
_cod_database_code               7160210
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C6H7N5
_chemical_oxdiff_usercomment     98K
_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   0.960
_shelx_estimated_absorpt_t_min   0.847
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006)
;
_shelx_res_file
;
TITL exp_2588_auto_a.res in P2(1)/n
    exp_2588_auto.res
    created by SHELXL-2018/3 at 16:51:33 on 12-Dec-2023
REM Old TITL exp_2588_auto_a.res in Pn
REM SHELXT solution in P2(1)/n: R1 0.057, Rweak 0.003, Alpha 0.017
REM <I/s> 0.496 for 29 systematic absences, Orientation as input
REM Formula found by SHELXT: C2 N3 Cl
CELL 0.71073 3.7758 18.2803 5.4893 90 109.377 90
ZERR 2 0.0004 0.0016 0.0007 0 0.013 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N S
UNIT 8 4 12 4

L.S. 4
PLAN  1
SIZE 0.06 0.11 0.25
TEMP -175
BOND
list 4
fmap 2
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\exp_2588_auto.hkl">
REM </olex2.extras>

WGHT    0.042700    0.218600
FVAR       1.15508
S01   4    0.727714    0.594781    0.083080    11.00000    0.01750    0.01430 =
         0.01206    0.00089    0.00654    0.00160
N002  3    0.658976    0.640230    0.504115    11.00000    0.01575    0.01534 =
         0.01504   -0.00193    0.00501    0.00017
N003  3    0.929788    0.522543    0.558409    11.00000    0.01464    0.01500 =
         0.01359   -0.00024    0.00529    0.00031
N004  3    0.549811    0.677464    0.080423    11.00000    0.01692    0.01387 =
         0.01878    0.00040    0.00665    0.00047
C005  1    0.779121    0.583951    0.405315    11.00000    0.01198    0.01647 =
         0.00930   -0.00076    0.00357   -0.00203
C006  1    0.535346    0.691232    0.312666    11.00000    0.01418    0.01426 =
         0.01830   -0.00188    0.00473   -0.00035
AFIX  43
H006  2    0.438900    0.736644    0.346907    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_2588_auto_a.res in P2(1)/n
REM wR2 = 0.0793, GooF = S = 1.085, Restrained GooF = 1.085 for all data
REM R1 = 0.0311 for 651 Fo > 4sig(Fo) and 0.0352 for all 716 data
REM 55 parameters refined using 0 restraints

END

WGHT      0.0427      0.2186

REM Highest difference peak  0.371,  deepest hole -0.288,  1-sigma level  0.074
Q1    1   0.9912  0.6018  0.1392  11.00000  0.05    0.37
;
_shelx_res_checksum              95878
_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 1.805
_oxdiff_exptl_absorpt_empirical_full_min 0.375
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
S01 S 0.72771(12) 0.59478(2) 0.08308(9) 0.0142(2) Uani 1 1 d . . . . .
N002 N 0.6590(4) 0.64023(9) 0.5041(3) 0.0154(4) Uani 1 1 d . . . . .
N003 N 0.9298(4) 0.52254(8) 0.5584(3) 0.0143(4) Uani 1 1 d . . . . .
N004 N 0.5498(5) 0.67746(8) 0.0804(3) 0.0163(4) Uani 1 1 d . . . . .
C005 C 0.7791(5) 0.58395(11) 0.4053(3) 0.0126(4) Uani 1 1 d . . . . .
C006 C 0.5353(5) 0.69123(10) 0.3127(4) 0.0157(4) Uani 1 1 d . . . . .
H006 H 0.438900 0.736644 0.346907 0.019 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
S01 0.0175(3) 0.0143(3) 0.0121(3) 0.00089(16) 0.0065(2) 0.00160(16)
N002 0.0157(8) 0.0153(8) 0.0150(9) -0.0019(6) 0.0050(6) 0.0002(6)
N003 0.0146(8) 0.0150(8) 0.0136(8) -0.0002(6) 0.0053(6) 0.0003(6)
N004 0.0169(8) 0.0139(8) 0.0188(9) 0.0004(6) 0.0067(7) 0.0005(6)
C005 0.0120(9) 0.0165(9) 0.0093(10) -0.0008(6) 0.0036(7) -0.0020(6)
C006 0.0142(9) 0.0143(9) 0.0183(11) -0.0019(7) 0.0047(7) -0.0003(7)
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -23 -3 0.0812
1 25 1 0.0332
-2 22 4 0.0297
-2 -24 0 0.0765
4 -15 -3 0.1062
1 -3 7 0.0175
-4 15 4 0.0764
-1 3 -7 0.0429
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
N004 S01 C005 91.21(9) . . ?
C005 N002 C006 107.09(17) . . ?
N003 N003 C005 111.9(2) 3_766 . ?
C006 N004 S01 108.26(14) . . ?
N002 C005 S01 113.39(14) . . ?
N002 C005 N003 120.42(16) . . ?
N003 C005 S01 126.19(14) . . ?
N004 C006 N002 120.03(17) . . ?
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
S01 N004 1.6521(16) . ?
S01 C005 1.7256(19) . ?
N002 C005 1.312(2) . ?
N002 C006 1.366(3) . ?
N003 N003 1.264(3) 3_766 ?
N003 C005 1.405(2) . ?
N004 C006 1.318(3) . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.6765 -22.9755 -3.1956 0.1232 0.5163 0.8475
1.2939 24.6009 0.6609 -0.2127 -0.8874 -0.4090
-2.1730 21.8127 3.5534 -0.1018 -0.4272 -0.8984
-2.0721 -23.5497 0.1123 0.2254 0.9397 0.2571
4.1961 -15.1286 -3.3887 0.1822 -0.0445 0.9822
0.5459 -2.8964 6.9452 0.9473 -0.2273 -0.2256
-4.1258 14.8007 3.9239 -0.1052 0.0260 -0.9941
-0.5256 2.8230 -6.9601 -0.9463 0.2270 0.2303
