# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2588_auto
_database_code_depnum_ccdc_archive 'CCDC 2371065'
loop_
_audit_author_name
_audit_author_address
'Kiyonori Takahashi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2024-07-16 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_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)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 N6 S2'
_chemical_formula_sum            'C4 H2 N6 S2'
_chemical_formula_weight         198.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C6H7N5
_chemical_oxdiff_usercomment     98K
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   3.7758(4)
_cell_length_b                   18.2803(16)
_cell_length_c                   5.4893(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.377(13)
_cell_angle_gamma                90
_cell_volume                     357.42(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1535
_cell_measurement_temperature    98.4(8)
_cell_measurement_theta_max      31.0600
_cell_measurement_theta_min      2.2220
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.847
_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_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             200
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

_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.061
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

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                651
_reflns_number_total             716
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.085
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_
_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) . . ?

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2589_auto
_database_code_depnum_ccdc_archive 'CCDC 2371066'
loop_
_audit_author_name
_audit_author_address
'Kiyonori Takahashi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2024-07-16 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_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)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 N6 S2'
_chemical_formula_sum            'C4 H2 N6 S2'
_chemical_formula_weight         198.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H2N8S2
_chemical_oxdiff_usercomment     99K
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   5.4717(3)
_cell_length_b                   9.3558(5)
_cell_length_c                   7.3148(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.154(5)
_cell_angle_gamma                90
_cell_volume                     372.95(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2786
_cell_measurement_temperature    98.8(6)
_cell_measurement_theta_max      31.0690
_cell_measurement_theta_min      3.5250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                683
_reflns_number_total             756
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0218
_refine_ls_restrained_S_all      1.056
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 ?

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 . ?

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2887_auto
_database_code_depnum_ccdc_archive 'CCDC 2371068'
loop_
_audit_author_name
_audit_author_address
'Kiyonori Takahashi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2024-07-16 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_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)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H8 N4 S2'
_chemical_formula_sum            'C8 H8 N4 S2'
_chemical_formula_weight         224.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
_chemical_oxdiff_usercomment     293K
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   10.3127(8)
_cell_length_b                   5.0803(2)
_cell_length_c                   10.6479(7)
_cell_angle_alpha                90
_cell_angle_beta                 118.281(9)
_cell_angle_gamma                90
_cell_volume                     491.27(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1537
_cell_measurement_temperature    292.95(10)
_cell_measurement_theta_max      28.1710
_cell_measurement_theta_min      2.2560
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.847
_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_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                931
_reflns_number_total             1107
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.049
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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) . ?

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) . . ?

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_867_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2371069'
loop_
_audit_author_name
_audit_author_address
'Kiyonori Takahashi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2024-07-16 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_audit_creation_date             2024-07-16
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 N4 S'
_chemical_formula_sum            'C8 H6 N4 S'
_chemical_formula_weight         190.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         C4H2N6S2
_chemical_oxdiff_usercomment     200K
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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'

_cell_length_a                   8.1698(4)
_cell_length_b                   5.5451(3)
_cell_length_c                   19.2296(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.039(4)
_cell_angle_gamma                90
_cell_volume                     864.58(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7106
_cell_measurement_temperature    200.00(14)
_cell_measurement_theta_max      71.9670
_cell_measurement_theta_min      2.3440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.954
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5133
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.627
_diffrn_reflns_theta_min         4.634
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  89.00   0.50    1.37    --    0.00  46.00 -90.00  356
  2  ω    -84.00  94.00   0.50    5.48    --    5.00  37.00-180.00  356
  3  ω   -185.00  -6.00   0.50    5.48    --  -95.70  49.00 -17.48  358
  4  ω   -185.00  -6.00   0.50    5.48    --  -95.70  46.00 150.00  358
  5  ω   -185.00  -6.00   0.50    5.48    --  -95.70  55.00-104.90  358
  6  ω   -185.00  -6.00   0.50    5.48    --  -95.70  55.00-104.90  358
  7  ω   -185.00  -6.00   0.50    5.48    --  -95.70  54.00  89.06  358
  8  ω   -185.00  -6.00   0.50    5.48    --  -95.70  38.00-140.93  358
  9  ω   -185.00  -6.00   0.50    5.48    --  -95.70  55.00  41.60  358
 10  ω   -185.00  -6.00   0.50    5.48    --  -95.70  46.00 150.00  358
 11  ω   -185.00  -6.00   0.50    5.48    --  -95.70  52.00 140.44  358
 12  ω   -185.00  -6.00   0.50    5.48    --  -95.70  55.00 -37.38  358
 13  ω    -89.00  89.00   0.50    1.37    --    0.00  18.00  60.00  356
 14  ω    -89.00  89.00   0.50    1.37    --    0.00  46.00-180.00  356
 15  ω   -185.00  -6.00   0.50    5.48    --  -95.70   0.00 -90.00  358
 16  ω   -185.00 -74.00   0.50    5.48    --  -95.70  46.00  60.00  222
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0180777000
_diffrn_orient_matrix_UB_12      0.0364390000
_diffrn_orient_matrix_UB_13      0.0800177000
_diffrn_orient_matrix_UB_21      0.1837785000
_diffrn_orient_matrix_UB_22      -0.0682352000
_diffrn_orient_matrix_UB_23      0.0047537000
_diffrn_orient_matrix_UB_31      0.0445926000
_diffrn_orient_matrix_UB_32      0.2667297000
_diffrn_orient_matrix_UB_33      -0.0098369000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4535
_reflns_number_total             5133
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         5133
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.059
_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)+(0.0808P)²+0.2122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1412
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.620(2)
 0.380(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 C7-C8 \\sim C7A-C8A
 with sigma of 0.02
4. Rigid bond restraints
 C8A, C7A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Uiso/Uaniso restraints and constraints
Uanis(C8A) = Uanis(S1)
6. Others
 Sof(N1A)=Sof(N2A)=Sof(C7A)=Sof(S1A)=Sof(C8A)=Sof(H8A)=1-FVAR(1)
 Sof(S1)=Sof(C8)=Sof(H8)=Sof(N1)=Sof(N2)=Sof(C7)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C6(H6), C4(H4), C3(H3), C2(H2), C8A(H8A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.0838(2) 0.8809(3) 0.58589(5) 0.0537(4) Uani 0.726(5) 1 d . . P A 1
C8 C 0.1718(17) 0.509(3) 0.6602(8) 0.146(8) Uani 0.726(5) 1 d D . P A 1
H8 H 0.210254 0.353538 0.675569 0.175 Uiso 0.726(5) 1 calc R U P A 1
N1 N 0.2212(5) 0.5702(11) 0.4849(2) 0.0451(9) Uani 0.726(5) 1 d . . P A 1
N2 N 0.2349(4) 0.4663(8) 0.54480(18) 0.0462(9) Uani 0.726(5) 1 d . . P A 1
C1 C 0.2949(3) 0.4393(5) 0.43335(12) 0.0505(7) Uani 1 1 d . . . . .
C7 C 0.1696(9) 0.5974(10) 0.5956(3) 0.0437(13) Uani 0.726(5) 1 d D . P A 1
C5 C 0.4463(4) 0.1273(7) 0.38472(18) 0.0693(9) Uani 1 1 d . . . . .
H5 H 0.502751 -0.022626 0.389376 0.083 Uiso 1 1 calc R U . . .
C6 C 0.3764(3) 0.2215(6) 0.44050(15) 0.0622(8) Uani 1 1 d . . . . .
H6 H 0.384340 0.136654 0.483696 0.075 Uiso 1 1 calc R U . . .
C4 C 0.4339(3) 0.2519(7) 0.32184(15) 0.0707(10) Uani 1 1 d . . . . .
H4 H 0.482946 0.187773 0.283511 0.085 Uiso 1 1 calc R U . . .
C3 C 0.3514(4) 0.4667(7) 0.31473(15) 0.0703(9) Uani 1 1 d . . . . .
H3 H 0.342757 0.551039 0.271427 0.084 Uiso 1 1 calc R U . . .
C2 C 0.2808(4) 0.5609(6) 0.37017(14) 0.0592(7) Uani 1 1 d . . . . .
H2 H 0.222489 0.709342 0.365027 0.071 Uiso 1 1 calc R U . . .
N1A N 0.2466(15) 0.452(3) 0.5085(9) 0.067(4) Uani 0.274(5) 1 d . . P A 2
N2A N 0.1874(17) 0.646(3) 0.5090(8) 0.072(4) Uani 0.274(5) 1 d . . P A 2
C7A C 0.144(3) 0.681(3) 0.5816(9) 0.052(4) Uani 0.274(5) 1 d D U P A 2
S1A S 0.1717(5) 0.5156(10) 0.6546(3) 0.0612(13) Uani 0.274(5) 1 d . . P A 2
N4 N 0.1032(3) 0.6963(5) 0.70377(11) 0.0662(8) Uani 1 1 d . . . . .
N3 N 0.0522(3) 0.8915(5) 0.67066(12) 0.0677(7) Uani 1 1 d . . . . .
C8A C 0.082(3) 0.886(4) 0.6021(9) 0.0537(4) Uani 0.274(5) 1 d D U P A 2
H8A H 0.058462 1.019728 0.571469 0.064 Uiso 0.274(5) 1 calc R U 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
S1 0.0682(6) 0.0545(6) 0.0404(7) -0.0021(6) 0.0145(6) -0.0009(4)
C8 0.177(13) 0.141(13) 0.123(12) -0.026(9) 0.029(8) -0.055(10)
N1 0.050(2) 0.051(3) 0.036(2) -0.0035(18) 0.0107(14) -0.0062(17)
N2 0.0552(19) 0.055(2) 0.0297(15) -0.0015(17) 0.0102(14) -0.0074(14)
C1 0.0459(14) 0.0616(19) 0.0455(12) -0.0099(11) 0.0116(10) -0.0100(12)
C7 0.046(3) 0.044(3) 0.041(2) 0.000(2) 0.0076(19) -0.005(2)
C5 0.0564(17) 0.062(2) 0.091(2) -0.0160(16) 0.0158(14) 0.0008(14)
C6 0.0565(16) 0.072(2) 0.0596(15) 0.0080(14) 0.0115(12) -0.0038(15)
C4 0.0542(16) 0.102(3) 0.0584(16) -0.0298(17) 0.0183(12) -0.0105(17)
C3 0.0655(18) 0.100(3) 0.0480(14) 0.0073(15) 0.0170(12) -0.0046(18)
C2 0.0586(16) 0.0611(19) 0.0599(15) 0.0013(13) 0.0147(12) -0.0044(14)
N1A 0.062(7) 0.061(8) 0.074(11) 0.001(8) -0.005(7) -0.013(6)
N2A 0.077(8) 0.072(10) 0.065(8) 0.002(6) 0.004(6) -0.019(7)
C7A 0.054(9) 0.055(8) 0.050(8) -0.006(7) 0.019(6) -0.007(7)
S1A 0.057(2) 0.064(3) 0.063(2) 0.025(2) 0.0111(17) -0.002(2)
N4 0.0837(18) 0.0736(19) 0.0445(11) -0.0088(11) 0.0215(11) -0.0136(14)
N3 0.0847(17) 0.0702(19) 0.0517(13) -0.0125(12) 0.0216(11) -0.0087(14)
C8A 0.0682(6) 0.0545(6) 0.0404(7) -0.0021(6) 0.0145(6) -0.0009(4)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C7 1.722(5) . ?
S1 N3 1.682(2) . ?
C8 C7 1.334(14) . ?
C8 N4 1.489(15) . ?
N1 N2 1.281(6) . ?
N1 C1 1.420(5) . ?
N2 C7 1.376(7) . ?
C1 C6 1.378(4) . ?
C1 C2 1.382(4) . ?
C1 N1A 1.546(19) . ?
C5 C6 1.378(4) . ?
C5 C4 1.385(5) . ?
C4 C3 1.367(5) . ?
C3 C2 1.376(4) . ?
N1A N2A 1.18(2) . ?
N2A C7A 1.49(2) . ?
C7A S1A 1.671(17) . ?
C7A C8A 1.33(2) . ?
S1A N4 1.530(7) . ?
N4 N3 1.298(4) . ?
N3 C8A 1.368(16) . ?

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
N3 S1 C7 92.1(2) . . ?
C7 C8 N4 107.6(11) . . ?
N2 N1 C1 113.6(5) . . ?
N1 N2 C7 113.7(5) . . ?
C6 C1 N1 128.3(3) . . ?
C6 C1 C2 120.2(2) . . ?
C6 C1 N1A 97.0(6) . . ?
C2 C1 N1 111.5(3) . . ?
C2 C1 N1A 142.8(7) . . ?
C8 C7 S1 113.4(8) . . ?
C8 C7 N2 120.2(8) . . ?
N2 C7 S1 126.4(4) . . ?
C6 C5 C4 119.8(3) . . ?
C1 C6 C5 119.7(3) . . ?
C3 C4 C5 120.3(3) . . ?
C4 C3 C2 120.1(3) . . ?
C3 C2 C1 119.9(3) . . ?
N2A N1A C1 101.5(17) . . ?
N1A N2A C7A 105.7(16) . . ?
N2A C7A S1A 133.7(12) . . ?
C8A C7A N2A 122.3(15) . . ?
C8A C7A S1A 103.7(13) . . ?
N4 S1A C7A 97.9(6) . . ?
N3 N4 C8 115.3(6) . . ?
N3 N4 S1A 111.3(2) . . ?
N4 N3 S1 111.6(2) . . ?
N4 N3 C8A 111.8(11) . . ?
C7A C8A N3 115.1(19) . . ?

_shelx_res_file                  
;
TITL exp_867_twin1_hklf4_a.res in P2(1)/n
    exp_867_twin1_hklf4.res
    created by SHELXL-2018/3 at 16:53:36 on 26-Mar-2024
REM Old TITL exp_867_twin1_hklf4 in P2
REM SHELXT solution in P2(1)/n: R1 0.226, Rweak 0.209, Alpha 0.035
REM <I/s> 1.838 for 167 systematic absences, Orientation as input
REM Formula found by SHELXT: C2 N1 S
CELL 1.54184 8.1698 5.5451 19.2296 90 97.039 90
ZERR 4 0.0004 0.0003 0.0009 0 0.004 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N S
UNIT 32 24 16 4
DELU 0.001 0.001 C8A C7A
EADP C8A S1
SADI C7 C8 C7A C8A

L.S. 50
PLAN  5
TEMP -73
fmap 2
ACTA
OMIT -2 -2 1
REM <olex2.extras>
REM <HklSrc "%.\\exp_867_twin1_hklf5.hkl">
REM </olex2.extras>

WGHT    0.080800    0.212200
BASF   0.38018
FVAR       6.63366   0.72575
PART 1
S1    4    0.083765    0.880893    0.585891    21.00000    0.06825    0.05452 =
         0.04044   -0.00210    0.01454   -0.00086
C8    1    0.171823    0.508578    0.660178    21.00000    0.17743    0.14101 =
         0.12265   -0.02602    0.02907   -0.05465
AFIX  43
H8    2    0.210254    0.353538    0.675569    21.00000   -1.20000
AFIX   0
N1    3    0.221201    0.570191    0.484853    21.00000    0.04976    0.05135 =
         0.03552   -0.00349    0.01072   -0.00620
N2    3    0.234919    0.466323    0.544798    21.00000    0.05517    0.05496 =
         0.02975   -0.00149    0.01015   -0.00741
PART 0
C1    1    0.294929    0.439340    0.433346    11.00000    0.04593    0.06164 =
         0.04546   -0.00995    0.01161   -0.00997
PART 1
C7    1    0.169623    0.597429    0.595578    21.00000    0.04629    0.04406 =
         0.04129   -0.00019    0.00762   -0.00537
PART 0
C5    1    0.446251    0.127342    0.384719    11.00000    0.05638    0.06182 =
         0.09143   -0.01598    0.01585    0.00077
AFIX  43
H5    2    0.502751   -0.022626    0.389376    11.00000   -1.20000
AFIX   0
C6    1    0.376376    0.221542    0.440500    11.00000    0.05647    0.07157 =
         0.05959    0.00796    0.01149   -0.00382
AFIX  43
H6    2    0.384340    0.136654    0.483696    11.00000   -1.20000
AFIX   0
C4    1    0.433896    0.251878    0.321838    11.00000    0.05424    0.10221 =
         0.05843   -0.02978    0.01832   -0.01045
AFIX  43
H4    2    0.482946    0.187773    0.283511    11.00000   -1.20000
AFIX   0
C3    1    0.351376    0.466711    0.314726    11.00000    0.06548    0.09984 =
         0.04799    0.00733    0.01698   -0.00455
AFIX  43
H3    2    0.342757    0.551039    0.271427    11.00000   -1.20000
AFIX   0
C2    1    0.280816    0.560937    0.370166    11.00000    0.05859    0.06108 =
         0.05987    0.00130    0.01470   -0.00435
AFIX  43
H2    2    0.222489    0.709342    0.365027    11.00000   -1.20000
AFIX   0
PART 2
N1A   3    0.246644    0.452019    0.508528   -21.00000    0.06191    0.06130 =
         0.07395    0.00098   -0.00505   -0.01318
N2A   3    0.187361    0.645978    0.508965   -21.00000    0.07687    0.07243 =
         0.06467    0.00243    0.00374   -0.01899
C7A   1    0.144488    0.681377    0.581567   -21.00000    0.05386    0.05501 =
         0.05043   -0.00609    0.01919   -0.00729
S1A   4    0.171665    0.515550    0.654617   -21.00000    0.05746    0.06409 =
         0.06291    0.02476    0.01108   -0.00228
PART 0
N4    3    0.103167    0.696324    0.703768    11.00000    0.08374    0.07359 =
         0.04455   -0.00876    0.02150   -0.01365
N3    3    0.052222    0.891527    0.670655    11.00000    0.08466    0.07015 =
         0.05169   -0.01246    0.02158   -0.00874
PART 2
C8A   1    0.081511    0.886358    0.602116   -21.00000    0.06825    0.05452 =
         0.04044   -0.00210    0.01454   -0.00086
AFIX  43
H8A   2    0.058462    1.019728    0.571469   -21.00000   -1.20000
AFIX   0
HKLF 5




REM  exp_867_twin1_hklf4_a.res in P2(1)/n
REM wR2 = 0.1412, GooF = S = 1.059, Restrained GooF = 1.059 for all data
REM R1 = 0.0475 for 4535 Fo > 4sig(Fo) and 0.0527 for all 5133 data
REM 159 parameters refined using 2 restraints

END

WGHT      0.0812      0.2093

REM Highest difference peak  0.135,  deepest hole -0.158,  1-sigma level  0.040
Q1    1   0.0457  0.6208  0.5974  11.00000  0.05    0.13
Q2    1   0.1081  0.6157  0.5864  11.00000  0.05    0.13
Q3    1   0.5000  0.0000  0.5000  10.50000  0.05    0.13
Q4    1   0.3925  0.5558  0.3477  11.00000  0.05    0.13
Q5    1   0.4939  0.0435  0.2984  11.00000  0.05    0.12
;
_shelx_res_checksum              30557
_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 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.812
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.620(2) 5844 9741 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.380(2) 5869 9741 nmt -1.0004 -0.0012 -0.0006 0.0013 -0.9983 -0.0000 0.5720
-0.0046 1.0006

_twin_special_details            
;
Component 2 rotated by 179.9170° 
around [-0.00 0.00 1.00] (reciprocal) or [0.27 -0.00 0.96] (direct)
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2735_autored
_database_code_depnum_ccdc_archive 'CCDC 2371071'
loop_
_audit_author_name
_audit_author_address
'Kiyonori Takahashi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2024-07-16 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_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)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 N4 S'
_chemical_formula_sum            'C8 H6 N4 S'
_chemical_formula_weight         190.23
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H6N4S
_chemical_oxdiff_usercomment     '200K, cis_Ph_NN_124N2S'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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'

_cell_length_a                   5.4747(2)
_cell_length_b                   15.4161(6)
_cell_length_c                   10.5241(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.253(4)
_cell_angle_gamma                90
_cell_volume                     860.88(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7269
_cell_measurement_temperature    199.95(10)
_cell_measurement_theta_max      31.0510
_cell_measurement_theta_min      2.6160
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.845
_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_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_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_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_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_coef       .
_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_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.081
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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) . ?

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) . . ?

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2755_auto
_database_code_depnum_ccdc_archive 'CCDC 2371070'
loop_
_audit_author_name
_audit_author_address
'Kiyonori Takahashi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2024-07-16 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_audit_creation_date             2024-03-07
_audit_creation_method           
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 N4 S'
_chemical_formula_sum            'C8 H6 N4 S'
_chemical_formula_weight         190.23
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H6N4S
_chemical_oxdiff_usercomment     200K
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   4.6262(2)
_cell_length_b                   10.7086(4)
_cell_length_c                   17.0055(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     842.45(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6979
_cell_measurement_temperature    199.90(14)
_cell_measurement_theta_max      30.6840
_cell_measurement_theta_min      2.2600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39162
_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_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9703
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.786
_diffrn_reflns_theta_min         2.248
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.90(14)
_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 0.880
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  38.00   0.50    1.79    --    5.68 -99.00 -60.00  112
  2  ω    -18.00  38.00   0.50    1.79    --    5.68 -99.00   0.00  112
  3  ω    -67.00  -8.00   0.50    1.79    --    5.68 -37.00  90.00  118
  4  ω     -7.00  78.00   0.50    1.79    --    5.68  40.00  68.00  170
  5  ω    -22.00  40.00   0.50    1.79    --    5.68  89.00-168.00  124
;
_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      0.0768119000
_diffrn_orient_matrix_UB_12      -0.0412923000
_diffrn_orient_matrix_UB_13      0.0250480000
_diffrn_orient_matrix_UB_21      -0.0115930000
_diffrn_orient_matrix_UB_22      0.0436876000
_diffrn_orient_matrix_UB_23      0.0311885000
_diffrn_orient_matrix_UB_31      -0.1321504000
_diffrn_orient_matrix_UB_32      -0.0278476000
_diffrn_orient_matrix_UB_33      0.0118136000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.623
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.794
_reflns_number_gt                1988
_reflns_number_total             2235
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 708 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.047
_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)+(0.0392P)²+0.0205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0705
_refine_special_details          ?
_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), C5(H5), C3(H3), C12(H12), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.11911(10) 0.77037(4) 0.69642(3) 0.03097(14) Uani 1 1 d . . . . .
N8 N 0.3923(3) 0.54409(13) 0.66467(9) 0.0261(3) Uani 1 1 d . . . . .
N7 N 0.5055(3) 0.60844(14) 0.61096(9) 0.0251(3) Uani 1 1 d . . . . .
N10 N 0.0512(4) 0.55919(15) 0.76587(10) 0.0342(4) Uani 1 1 d . . . . .
N11 N -0.1333(4) 0.64169(15) 0.80325(10) 0.0370(4) Uani 1 1 d . . . . .
C1 C 0.7102(4) 0.54319(16) 0.56427(11) 0.0242(4) Uani 1 1 d . . . . .
C2 C 0.8035(4) 0.42152(16) 0.57865(11) 0.0274(4) Uani 1 1 d . . . . .
H2 H 0.726175 0.375350 0.621455 0.033 Uiso 1 1 calc R U . . .
C9 C 0.1945(4) 0.61348(15) 0.70959(10) 0.0253(4) Uani 1 1 d . . . . .
C6 C 0.8196(4) 0.60993(16) 0.50067(11) 0.0292(4) Uani 1 1 d . . . . .
H6 H 0.755822 0.692816 0.490921 0.035 Uiso 1 1 calc R U . . .
C5 C 1.0220(4) 0.5549(2) 0.45165(12) 0.0348(4) Uani 1 1 d . . . . .
H5 H 1.096175 0.600015 0.407983 0.042 Uiso 1 1 calc R U . . .
C3 C 1.0091(4) 0.36877(17) 0.53022(12) 0.0318(4) Uani 1 1 d . . . . .
H3 H 1.077757 0.286862 0.540777 0.038 Uiso 1 1 calc R U . . .
C12 C -0.1182(4) 0.75302(18) 0.77262(12) 0.0324(4) Uani 1 1 d . . . . .
H12 H -0.232181 0.820435 0.791509 0.039 Uiso 1 1 calc R U . . .
C4 C 1.1166(5) 0.43450(17) 0.46604(11) 0.0324(4) Uani 1 1 d . . . . .
H4 H 1.254662 0.396810 0.432172 0.039 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 0.0338(2) 0.0253(2) 0.0337(3) 0.00006(17) 0.0038(2) 0.00181(17)
N8 0.0271(7) 0.0248(7) 0.0263(7) -0.0004(6) -0.0003(7) -0.0009(7)
N7 0.0242(7) 0.0247(7) 0.0265(8) -0.0007(6) -0.0018(6) -0.0018(6)
N10 0.0392(10) 0.0306(8) 0.0327(9) 0.0003(7) 0.0070(7) -0.0008(7)
N11 0.0383(9) 0.0390(8) 0.0335(9) -0.0042(7) 0.0100(9) -0.0018(7)
C1 0.0229(8) 0.0243(8) 0.0254(9) -0.0015(7) -0.0025(7) -0.0015(6)
C2 0.0294(10) 0.0234(8) 0.0292(10) 0.0017(7) 0.0005(7) -0.0024(7)
C9 0.0267(9) 0.0237(8) 0.0256(9) -0.0020(7) -0.0015(7) -0.0018(6)
C6 0.0312(10) 0.0254(8) 0.0309(10) 0.0055(8) -0.0006(7) 0.0008(7)
C5 0.0342(10) 0.0401(10) 0.0301(10) 0.0067(8) 0.0040(8) -0.0009(8)
C3 0.0327(9) 0.0249(9) 0.0380(11) -0.0022(8) -0.0026(9) 0.0014(7)
C12 0.0299(9) 0.0355(10) 0.0319(9) -0.0089(7) 0.0007(8) -0.0001(8)
C4 0.0304(9) 0.0375(10) 0.0293(9) -0.0062(7) 0.0004(9) 0.0031(9)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C9 1.7304(17) . ?
S13 C12 1.708(2) . ?
N8 N7 1.258(2) . ?
N8 C9 1.405(2) . ?
N7 C1 1.420(2) . ?
N10 N11 1.383(2) . ?
N10 C9 1.301(2) . ?
N11 C12 1.303(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.392(2) . ?
C2 C3 1.379(3) . ?
C6 C5 1.385(3) . ?
C5 C4 1.383(3) . ?
C3 C4 1.391(3) . ?

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
C12 S13 C9 85.74(9) . . ?
N7 N8 C9 112.09(14) . . ?
N8 N7 C1 114.45(15) . . ?
C9 N10 N11 111.53(16) . . ?
C12 N11 N10 111.57(16) . . ?
C2 C1 N7 124.64(16) . . ?
C6 C1 N7 115.12(15) . . ?
C6 C1 C2 120.24(17) . . ?
C3 C2 C1 119.45(17) . . ?
N8 C9 S13 125.06(13) . . ?
N10 C9 S13 115.23(14) . . ?
N10 C9 N8 119.71(16) . . ?
C5 C6 C1 119.67(17) . . ?
C4 C5 C6 120.25(18) . . ?
C2 C3 C4 120.53(18) . . ?
N11 C12 S13 115.92(15) . . ?
C5 C4 C3 119.83(19) . . ?

_shelx_res_file                  
;
TITL exp_2755_auto_a.res in P2(1)2(1)2(1)
    exp_2755_auto.res
    created by SHELXL-2018/3 at 11:57:12 on 07-Mar-2024
REM Old TITL exp_2755_auto in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1): R1 0.072, Rweak 0.013, Alpha 0.001
REM <I/s> 0.511 for 19 systematic absences, Orientation as input
REM Flack x = 0.027 ( 0.036 ) from 626 Parsons' quotients
REM Formula found by SHELXT: C4 N7 S
CELL 0.71073 4.6262 10.7086 17.0055 90 90 90
ZERR 4 0.0002 0.0004 0.0007 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  5
TEMP -73
fmap 2
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\exp_2755_auto.hkl">
REM </olex2.extras>

WGHT    0.039200    0.020500
FVAR       2.07007
S13   4    0.119113    0.770370    0.696419    11.00000    0.03385    0.02534 =
         0.03371    0.00006    0.00380    0.00181
N8    3    0.392311    0.544090    0.664670    11.00000    0.02714    0.02478 =
         0.02629   -0.00038   -0.00030   -0.00087
N7    3    0.505466    0.608442    0.610962    11.00000    0.02424    0.02469 =
         0.02648   -0.00066   -0.00180   -0.00184
N10   3    0.051197    0.559193    0.765873    11.00000    0.03923    0.03059 =
         0.03272    0.00028    0.00700   -0.00084
N11   3   -0.133269    0.641685    0.803252    11.00000    0.03834    0.03898 =
         0.03354   -0.00423    0.01002   -0.00181
C1    1    0.710207    0.543189    0.564267    11.00000    0.02291    0.02426 =
         0.02545   -0.00149   -0.00254   -0.00152
C2    1    0.803533    0.421525    0.578648    11.00000    0.02942    0.02343 =
         0.02921    0.00172    0.00051   -0.00242
AFIX  43
H2    2    0.726175    0.375350    0.621455    11.00000   -1.20000
AFIX   0
C9    1    0.194492    0.613479    0.709592    11.00000    0.02666    0.02365 =
         0.02565   -0.00205   -0.00153   -0.00185
C6    1    0.819623    0.609926    0.500670    11.00000    0.03123    0.02536 =
         0.03094    0.00548   -0.00058    0.00080
AFIX  43
H6    2    0.755822    0.692816    0.490921    11.00000   -1.20000
AFIX   0
C5    1    1.022032    0.554898    0.451650    11.00000    0.03421    0.04011 =
         0.03013    0.00666    0.00396   -0.00094
AFIX  43
H5    2    1.096175    0.600015    0.407983    11.00000   -1.20000
AFIX   0
C3    1    1.009071    0.368767    0.530217    11.00000    0.03266    0.02487 =
         0.03796   -0.00219   -0.00259    0.00139
AFIX  43
H3    2    1.077757    0.286862    0.540777    11.00000   -1.20000
AFIX   0
C12   1   -0.118183    0.753018    0.772622    11.00000    0.02994    0.03550 =
         0.03186   -0.00885    0.00067   -0.00012
AFIX  43
H12   2   -0.232181    0.820435    0.791509    11.00000   -1.20000
AFIX   0
C4    1    1.116607    0.434495    0.466042    11.00000    0.03039    0.03754 =
         0.02934   -0.00624    0.00043    0.00314
AFIX  43
H4    2    1.254662    0.396810    0.432172    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_2755_auto_a.res in P2(1)2(1)2(1)
REM wR2 = 0.0705, GooF = S = 1.047, Restrained GooF = 1.047 for all data
REM R1 = 0.0291 for 1988 Fo > 4sig(Fo) and 0.0357 for all 2235 data
REM 118 parameters refined using 0 restraints

END

WGHT      0.0392      0.0205

REM Highest difference peak  0.281,  deepest hole -0.159,  1-sigma level  0.042
Q1    1   0.1289  0.6903  0.6992  11.00000  0.05    0.28
Q2    1   0.7424  0.5603  0.5240  11.00000  0.05    0.19
Q3    1   0.0708  0.4835  0.7649  11.00000  0.05    0.18
Q4    1   0.8617  0.5592  0.4751  11.00000  0.05    0.16
Q5    1  -0.0812  0.6998  0.7992  11.00000  0.05    0.16
;
_shelx_res_checksum              54226
_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 1.923
_oxdiff_exptl_absorpt_empirical_full_min 0.413
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2732_auto
_database_code_depnum_ccdc_archive 'CCDC 2371067'
loop_
_audit_author_name
_audit_author_address
'Kiyonori Takahashi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2024-07-16 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_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)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 N4 S'
_chemical_formula_sum            'C8 H6 N4 S'
_chemical_formula_weight         190.23
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C7H6N4S
_chemical_oxdiff_usercomment     '200K, cis_Ph_NN_123N2S'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   5.9619(3)
_cell_length_b                   8.0466(6)
_cell_length_c                   18.1430(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     870.37(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3993
_cell_measurement_temperature    200.00(14)
_cell_measurement_theta_max      29.9870
_cell_measurement_theta_min      2.2210
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.763
_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_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_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_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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    ?
_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_coef       .
_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_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.030
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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) . ?

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) . . ?

_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
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2955_auto
_database_code_depnum_ccdc_archive 'CCDC 2371072'
loop_
_audit_author_name
_audit_author_address
'Kiyonori Takahashi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2024-07-16 deposited with the CCDC.	2024-11-06 downloaded from the CCDC.
;
_audit_creation_date             2024-07-09
_audit_creation_method           
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H8 N4 S2'
_chemical_formula_sum            'C8 H8 N4 S2'
_chemical_formula_weight         224.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H8N4S2
_chemical_oxdiff_usercomment     293K
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   18.2855(12)
_cell_length_b                   4.9987(3)
_cell_length_c                   11.3283(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.829(6)
_cell_angle_gamma                90
_cell_volume                     1030.08(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2648
_cell_measurement_temperature    292.95(10)
_cell_measurement_theta_max      27.3360
_cell_measurement_theta_min      2.2800
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.699
_exptl_absorpt_coefficient_mu    0.481
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59482
_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_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6044
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.795
_diffrn_reflns_theta_min         2.239
_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 0.996
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00  -9.00   0.50    1.01    --  -21.77 -42.00 106.00  186
  2  ω     -1.00  25.00   0.50    1.01    --  -21.77 -99.00  30.00   52
  3  ω     -5.00  36.00   0.50    1.01    --  -21.77 -99.00   0.00   82
  4  ω    -12.00  36.00   0.50    1.01    --  -21.77 -99.00-120.00   96
  5  ω    -40.00  51.00   0.50    1.01    --  -21.77  42.00-100.00  182
  6  ω     47.00 101.00   0.50    1.01    --   21.93 178.00 150.00  108
;
_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      -0.0316475000
_diffrn_orient_matrix_UB_12      0.0722043000
_diffrn_orient_matrix_UB_13      -0.0230426000
_diffrn_orient_matrix_UB_21      -0.0122997000
_diffrn_orient_matrix_UB_22      0.0038856000
_diffrn_orient_matrix_UB_23      0.0574333000
_diffrn_orient_matrix_UB_31      0.0191094000
_diffrn_orient_matrix_UB_32      0.1220360000
_diffrn_orient_matrix_UB_33      0.0118586000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1600
_reflns_number_total             2342
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_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     129
_refine_ls_number_reflns         2342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0775P)²+0.6087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1738
_refine_special_details          ?
_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:
 C3(H3), C11(H11)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
S9 S 0.81544(5) 0.83433(16) 0.86551(7) 0.0594(3) Uani 1 1 d . . . . .
S1 S 0.69877(6) 0.1471(2) 0.51410(8) 0.0764(3) Uani 1 1 d . . . . .
N6 N 0.73708(15) 0.4307(5) 0.7219(2) 0.0592(7) Uani 1 1 d . . . . .
N7 N 0.78703(15) 0.5193(5) 0.6648(2) 0.0593(7) Uani 1 1 d . . . . .
N12 N 0.88865(16) 0.8069(5) 0.6832(2) 0.0625(7) Uani 1 1 d . . . . .
N5 N 0.63145(19) -0.0720(7) 0.5131(3) 0.0817(9) Uani 1 1 d . . . . .
C8 C 0.83089(18) 0.7109(6) 0.7279(3) 0.0541(7) Uani 1 1 d . . . . .
C10 C 0.89230(17) 1.0296(6) 0.8649(3) 0.0546(7) Uani 1 1 d . . . . .
C3 C 0.63990(18) 0.0975(7) 0.7033(3) 0.0609(8) Uani 1 1 d . . . . .
H3 H 0.627545 0.113627 0.780577 0.073 Uiso 1 1 calc R U . . .
C2 C 0.69295(18) 0.2384(6) 0.6584(3) 0.0571(8) Uani 1 1 d . . . . .
C4 C 0.60484(19) -0.0807(7) 0.6165(3) 0.0665(9) Uani 1 1 d . . . . .
C11 C 0.92285(19) 0.9861(7) 0.7617(3) 0.0652(9) Uani 1 1 d . . . . .
H11 H 0.965350 1.074852 0.745252 0.078 Uiso 1 1 calc R U . . .
C13 C 0.9190(2) 1.2109(7) 0.9648(3) 0.0703(9) Uani 1 1 d . . . . .
H13A H 0.881092 1.336662 0.978483 0.106 Uiso 1 1 calc R U . . .
H13B H 0.961762 1.305683 0.944980 0.106 Uiso 1 1 calc R U . . .
H13C H 0.931381 1.107014 1.035318 0.106 Uiso 1 1 calc R U . . .
C14 C 0.5428(2) -0.2649(9) 0.6365(5) 0.0972(14) Uani 1 1 d . . . . .
H14A H 0.496976 -0.181387 0.608872 0.146 Uiso 1 1 calc R U . . .
H14B H 0.543686 -0.302844 0.719740 0.146 Uiso 1 1 calc R U . . .
H14C H 0.547974 -0.428582 0.593852 0.146 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
S9 0.0600(5) 0.0658(5) 0.0523(5) -0.0017(3) 0.0057(4) 0.0007(4)
S1 0.0812(7) 0.0936(7) 0.0534(5) -0.0116(4) 0.0017(5) -0.0040(5)
N6 0.0590(16) 0.0684(15) 0.0493(14) 0.0018(12) 0.0002(12) 0.0027(13)
N7 0.0577(16) 0.0687(16) 0.0506(15) 0.0047(12) 0.0011(12) 0.0073(13)
N12 0.0627(17) 0.0737(17) 0.0524(16) -0.0010(12) 0.0129(13) -0.0108(14)
N5 0.079(2) 0.086(2) 0.076(2) -0.0218(17) -0.0095(17) 0.0005(17)
C8 0.0550(18) 0.0570(16) 0.0490(17) 0.0033(13) -0.0007(14) 0.0055(13)
C10 0.0557(18) 0.0489(15) 0.0574(18) 0.0045(13) -0.0032(14) 0.0067(13)
C3 0.0541(19) 0.075(2) 0.0532(18) -0.0025(15) 0.0013(14) 0.0016(15)
C2 0.0543(19) 0.0632(17) 0.0511(18) -0.0011(14) -0.0079(14) 0.0090(14)
C4 0.054(2) 0.0609(18) 0.081(3) -0.0049(17) -0.0085(18) 0.0087(15)
C11 0.057(2) 0.070(2) 0.068(2) 0.0022(16) 0.0046(17) -0.0089(16)
C13 0.076(2) 0.0611(19) 0.072(2) -0.0069(16) -0.0031(18) 0.0006(16)
C14 0.077(3) 0.079(2) 0.133(4) -0.011(3) -0.007(3) -0.011(2)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
S9 C8 1.726(3) . ?
S9 C10 1.712(3) . ?
S1 N5 1.647(4) . ?
S1 C2 1.710(3) . ?
N6 N7 1.253(4) . ?
N6 C2 1.406(4) . ?
N7 C8 1.398(4) . ?
N12 C8 1.308(4) . ?
N12 C11 1.368(4) . ?
N5 C4 1.314(5) . ?
C10 C11 1.364(5) . ?
C10 C13 1.493(5) . ?
C3 C2 1.340(5) . ?
C3 C4 1.429(5) . ?
C4 C14 1.496(6) . ?

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
C10 S9 C8 89.46(16) . . ?
N5 S1 C2 93.73(18) . . ?
N7 N6 C2 112.8(3) . . ?
N6 N7 C8 112.8(3) . . ?
C8 N12 C11 108.8(3) . . ?
C4 N5 S1 111.1(3) . . ?
N7 C8 S9 124.7(2) . . ?
N12 C8 S9 115.5(2) . . ?
N12 C8 N7 119.8(3) . . ?
C11 C10 S9 108.7(2) . . ?
C11 C10 C13 128.0(3) . . ?
C13 C10 S9 123.3(3) . . ?
C2 C3 C4 111.0(3) . . ?
N6 C2 S1 125.7(3) . . ?
C3 C2 S1 109.9(3) . . ?
C3 C2 N6 124.4(3) . . ?
N5 C4 C3 114.3(3) . . ?
N5 C4 C14 120.7(4) . . ?
C3 C4 C14 125.0(4) . . ?
C10 C11 N12 117.5(3) . . ?

_shelx_res_file                  
;
TITL exp_2955_auto_a.res in P2(1)/c
    exp_2955_auto.res
    created by SHELXL-2018/3 at 11:37:09 on 09-Jul-2024
REM Old TITL exp_2955_auto in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.163, Rweak 0.260, Alpha 0.020
REM <I/s> 0.191 for 240 systematic absences, Orientation as input
REM Formula found by SHELXT: C14 N12 S1
CELL 0.71073 18.285507 4.998659 11.328251 90 95.8292 90
ZERR 4 0.001234 0.000256 0.000676 0 0.006 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N S
UNIT 32 32 16 8

L.S. 4
PLAN  2
SIZE 0.1 0.15 0.8
TEMP 20
fmap 2
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\exp_2955_auto.hkl">
REM </olex2.extras>

WGHT    0.077500    0.608700
FVAR       3.43893
S9    4    0.815437    0.834329    0.865509    11.00000    0.05999    0.06584 =
         0.05230   -0.00170    0.00572    0.00075
S1    4    0.698775    0.147123    0.514102    11.00000    0.08117    0.09361 =
         0.05341   -0.01161    0.00168   -0.00398
N6    3    0.737079    0.430714    0.721916    11.00000    0.05896    0.06842 =
         0.04926    0.00179    0.00017    0.00273
N7    3    0.787032    0.519311    0.664757    11.00000    0.05770    0.06872 =
         0.05061    0.00475    0.00110    0.00726
N12   3    0.888654    0.806941    0.683172    11.00000    0.06270    0.07375 =
         0.05245   -0.00100    0.01286   -0.01078
N5    3    0.631445   -0.071978    0.513086    11.00000    0.07926    0.08602 =
         0.07623   -0.02180   -0.00951    0.00049
C8    1    0.830887    0.710875    0.727884    11.00000    0.05498    0.05703 =
         0.04902    0.00334   -0.00072    0.00551
C10   1    0.892295    1.029588    0.864909    11.00000    0.05570    0.04895 =
         0.05738    0.00449   -0.00322    0.00667
C3    1    0.639903    0.097526    0.703259    11.00000    0.05411    0.07451 =
         0.05317   -0.00253    0.00127    0.00165
AFIX  43
H3    2    0.627545    0.113627    0.780577    11.00000   -1.20000
AFIX   0
C2    1    0.692954    0.238381    0.658354    11.00000    0.05430    0.06318 =
         0.05112   -0.00114   -0.00788    0.00904
C4    1    0.604839   -0.080746    0.616512    11.00000    0.05446    0.06094 =
         0.08103   -0.00486   -0.00854    0.00873
C11   1    0.922850    0.986052    0.761663    11.00000    0.05665    0.07034 =
         0.06836    0.00224    0.00463   -0.00888
AFIX  43
H11   2    0.965350    1.074852    0.745252    11.00000   -1.20000
AFIX   0
C13   1    0.919018    1.210925    0.964844    11.00000    0.07555    0.06113 =
         0.07216   -0.00686   -0.00311    0.00055
AFIX 137
H13A  2    0.881092    1.336662    0.978483    11.00000   -1.50000
H13B  2    0.961762    1.305683    0.944980    11.00000   -1.50000
H13C  2    0.931381    1.107014    1.035318    11.00000   -1.50000
AFIX   0
C14   1    0.542815   -0.264877    0.636537    11.00000    0.07677    0.07858 =
         0.13284   -0.01094   -0.00664   -0.01085
AFIX 137
H14A  2    0.496976   -0.181387    0.608872    11.00000   -1.50000
H14B  2    0.543686   -0.302844    0.719740    11.00000   -1.50000
H14C  2    0.547974   -0.428582    0.593852    11.00000   -1.50000
AFIX   0
HKLF 4




REM  exp_2955_auto_a.res in P2(1)/c
REM wR2 = 0.1738, GooF = S = 1.052, Restrained GooF = 1.052 for all data
REM R1 = 0.0559 for 1600 Fo > 4sig(Fo) and 0.0810 for all 2342 data
REM 129 parameters refined using 0 restraints

END

WGHT      0.0774      0.6097

REM Highest difference peak  0.347,  deepest hole -0.364,  1-sigma level  0.064
Q1    1   0.8219  0.7284  0.8028  11.00000  0.05    0.35
Q2    1   0.6984  0.1929  0.5950  11.00000  0.05    0.28
;
_shelx_res_checksum              18548
_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 2.592
_oxdiff_exptl_absorpt_empirical_full_min 0.351
