# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2114703'
loop_
_audit_author_name
_audit_author_address
'Alireza Salimi'
;Ferdowsi University of Mashhad
Iran
;
_audit_update_record             
;
2021-10-08 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H6 N4 O S'
_chemical_formula_weight         206.23

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.883(4)
_cell_length_b                   7.0318(14)
_cell_length_c                   25.673(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3589.5(12)
_cell_formula_units_Z            16
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3093
_cell_measurement_theta_min      1.888
_cell_measurement_theta_max      24.999

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             1696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.329
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_reflns_number            15764
_diffrn_reflns_av_unetI/netI     0.4072
_diffrn_reflns_av_R_equivalents  0.2625
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.888
_diffrn_reflns_theta_max         29.209
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4833
_reflns_number_gt                1040
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4833
_refine_ls_number_parameters     261
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.3369
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0536
_refine_ls_goodness_of_fit_ref   0.704
_refine_ls_restrained_S_all      0.704
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N6 N 0.0454(3) 1.0399(7) 0.32391(19) 0.0446(14) Uani 1 1 d D . . . .
C11 C 0.1846(3) 0.9559(8) 0.2284(2) 0.0658(19) Uani 1 1 d . . . . .
H11 H 0.210759 0.926204 0.199474 0.079 Uiso 1 1 calc R U . . .
N5 N 0.1611(3) 1.0708(7) 0.31000(17) 0.0545(14) Uani 1 1 d . . . . .
C10 C 0.2079(3) 1.0376(8) 0.2718(2) 0.0612(18) Uani 1 1 d . . . . .
H10 H 0.252961 1.069673 0.275886 0.073 Uiso 1 1 calc R U . . .
C9 C 0.1031(4) 1.0144(7) 0.2944(2) 0.0411(15) Uani 1 1 d . . . . .
C12 C -0.0154(4) 0.9745(8) 0.3097(2) 0.0443(17) Uani 1 1 d . . . . .
C14 C -0.1211(4) 1.1883(10) 0.4085(2) 0.080(2) Uani 1 1 d . . . . .
H14 H -0.118404 1.277477 0.435169 0.096 Uiso 1 1 calc R U . . .
C16 C -0.1351(4) 0.9336(9) 0.3353(2) 0.0597(18) Uani 1 1 d . . . . .
H16 H -0.137853 0.842065 0.309203 0.072 Uiso 1 1 calc R U . . .
N7 N -0.0659(3) 1.1476(7) 0.38132(19) 0.0620(16) Uani 1 1 d . . . . .
C13 C -0.0743(3) 1.0216(8) 0.3441(2) 0.0416(16) Uani 1 1 d . . . . .
C15 C -0.1819(4) 1.1027(12) 0.3984(3) 0.084(3) Uani 1 1 d . . . . .
H15 H -0.219083 1.137896 0.418075 0.101 Uiso 1 1 calc R U . . .
O2 O -0.02491(18) 0.8890(5) 0.26875(15) 0.0592(11) Uani 1 1 d . . . . .
N8 N -0.1893(3) 0.9741(8) 0.3623(2) 0.0733(18) Uani 1 1 d . . . . .
H2N H -0.291(3) 1.349(7) 0.6128(10) 0.07(2) Uiso 1 1 d D . . . .
H6N H 0.055(2) 1.068(6) 0.3549(9) 0.038(17) Uiso 1 1 d D . . . .
S2 S 0.10035(8) 0.9138(2) 0.23308(6) 0.0560(5) Uani 1 1 d . . . . .
S1 S -0.34027(9) 1.2116(2) 0.48712(6) 0.0579(5) Uani 1 1 d . . . . .
O1 O -0.21262(18) 1.2252(5) 0.51701(15) 0.0614(11) Uani 1 1 d . . . . .
C1 C -0.3426(4) 1.2878(8) 0.5507(2) 0.0484(16) Uani 1 1 d . . . . .
N2 N -0.2850(3) 1.3153(7) 0.58033(18) 0.0426(12) Uani 1 1 d D . . . .
N3 N -0.1771(2) 1.4165(6) 0.64111(16) 0.0451(13) Uani 1 1 d . . . . .
C5 C -0.1644(3) 1.3372(7) 0.5953(2) 0.0396(15) Uani 1 1 d . . . . .
N1 N -0.4018(3) 1.3200(7) 0.56901(16) 0.0535(14) Uani 1 1 d . . . . .
C8 C -0.0997(4) 1.3074(8) 0.5784(2) 0.0522(17) Uani 1 1 d . . . . .
H8 H -0.093477 1.249685 0.546174 0.063 Uiso 1 1 calc R U . . .
C4 C -0.2220(4) 1.2864(8) 0.5610(2) 0.0441(16) Uani 1 1 d . . . . .
C6 C -0.1241(4) 1.4670(8) 0.6686(2) 0.0503(17) Uani 1 1 d . . . . .
H6 H -0.130355 1.523968 0.700925 0.060 Uiso 1 1 calc R U . . .
N4 N -0.0457(3) 1.3565(7) 0.6055(2) 0.0598(16) Uani 1 1 d . . . . .
C3 C -0.4257(3) 1.2270(9) 0.4845(3) 0.070(2) Uani 1 1 d . . . . .
H3 H -0.452228 1.198767 0.455698 0.084 Uiso 1 1 calc R U . . .
C7 C -0.0600(4) 1.4380(8) 0.6509(2) 0.0525(18) Uani 1 1 d . . . . .
H7 H -0.024377 1.477461 0.671737 0.063 Uiso 1 1 calc R U . . .
C2 C -0.4480(4) 1.2859(9) 0.5305(2) 0.068(2) Uani 1 1 d . . . . .
H2 H -0.493763 1.303601 0.536391 0.081 Uiso 1 1 calc R U . . .


_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
N6 C12 1.345(7) . ?
N6 C9 1.386(7) . ?
C11 C10 1.338(7) . ?
C11 S2 1.705(6) . ?
N5 C9 1.285(6) . ?
N5 C10 1.371(6) . ?
C9 S2 1.726(5) . ?
C12 O2 1.226(5) . ?
C12 C13 1.504(8) . ?
C14 N7 1.331(8) . ?
C14 C15 1.375(8) . ?
C16 N8 1.313(7) . ?
C16 C13 1.377(7) . ?
N7 C13 1.313(6) . ?
C15 N8 1.304(7) . ?
S1 C3 1.703(6) . ?
S1 C1 1.718(5) . ?
O1 C4 1.223(6) . ?
C1 N1 1.288(7) . ?
C1 N2 1.389(7) . ?
N2 C4 1.361(7) . ?
N3 C6 1.318(7) . ?
N3 C5 1.326(6) . ?
C5 C8 1.374(7) . ?
C5 C4 1.488(7) . ?
N1 C2 1.371(6) . ?
C8 N4 1.326(7) . ?
C6 C7 1.369(7) . ?
N4 C7 1.328(6) . ?
C3 C2 1.328(7) . ?

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 N6 C9 123.5(5) . . ?
C10 C11 S2 110.8(5) . . ?
C9 N5 C10 109.5(5) . . ?
C11 C10 N5 115.7(6) . . ?
N5 C9 N6 122.2(5) . . ?
N5 C9 S2 116.1(5) . . ?
N6 C9 S2 121.7(5) . . ?
O2 C12 N6 122.5(6) . . ?
O2 C12 C13 119.5(6) . . ?
N6 C12 C13 117.8(5) . . ?
N7 C14 C15 122.1(7) . . ?
N8 C16 C13 122.4(6) . . ?
C13 N7 C14 114.9(6) . . ?
N7 C13 C16 122.4(6) . . ?
N7 C13 C12 118.5(6) . . ?
C16 C13 C12 119.1(6) . . ?
N8 C15 C14 122.6(7) . . ?
C15 N8 C16 115.6(6) . . ?
C11 S2 C9 87.9(3) . . ?
C3 S1 C1 89.4(4) . . ?
N1 C1 N2 122.0(5) . . ?
N1 C1 S1 115.3(5) . . ?
N2 C1 S1 122.8(5) . . ?
C4 N2 C1 122.6(5) . . ?
C6 N3 C5 115.9(5) . . ?
N3 C5 C8 121.5(6) . . ?
N3 C5 C4 118.6(6) . . ?
C8 C5 C4 119.9(5) . . ?
C1 N1 C2 108.6(5) . . ?
N4 C8 C5 123.6(5) . . ?
O1 C4 N2 122.0(6) . . ?
O1 C4 C5 120.8(6) . . ?
N2 C4 C5 117.2(5) . . ?
N3 C6 C7 121.8(5) . . ?
C8 N4 C7 113.6(5) . . ?
C2 C3 S1 108.6(5) . . ?
N4 C7 C6 123.7(6) . . ?
C3 C2 N1 118.1(6) . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042



# start Validation Reply Form
_vrf_RINTA01_shelx               
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: The investigated single crystals was poorly diffracting crystals. 
Numerous datasets were collected on single crystals from different batches 
and the highest quality is reported herein. 
Since the fine crystals tend to crack under the N2 flow, 
the data collection was performed on the room temprature
;
_vrf_PLAT026_shelx               
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        22% Check 
RESPONSE: The investigated single crystals was poorly diffracting crystals. 
Numerous datasets were collected on single crystals from different batches 
and the highest quality is reported herein. 
Since the fine crystals tend to crack under the N2 flow, 
the data collection was performed on the room temprature   
;
# end Validation Reply Form
####################################################################### 
# 
# 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_iran-ft-9-cold
_database_code_depnum_ccdc_archive 'CCDC 2114705'
loop_
_audit_author_name
_audit_author_address
'Alireza Salimi'
;Ferdowsi University of Mashhad
Iran
;
_audit_update_record             
;
2021-10-08 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;
_audit_creation_date             2014-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H6 N4 O S'
_chemical_formula_sum            'C8 H6 N4 O S'
_chemical_formula_weight         206.23
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H5 N3 O1 S1'
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'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.8771(5)
_cell_length_b                   5.1276(2)
_cell_length_c                   17.5128(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.776(5)
_cell_angle_gamma                90
_cell_volume                     868.29(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2118
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.0280
_cell_measurement_theta_min      4.5710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3500
_diffrn_reflns_point_group_measured_fraction_full 0.736
_diffrn_reflns_point_group_measured_fraction_max 0.689
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.566
_diffrn_reflns_theta_min         4.573
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2603
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -111.00  -22.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      -45.5339  -57.0000 -150.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega  -66.00   17.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      -45.5339   57.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
  3 omega   69.00   95.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -       45.5339   38.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   44.00   96.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      108.9025  -95.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega   91.00  176.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      108.9025   45.0000  120.0000 85

#__ type_ start__ end____ width___ exp.time_
  6 omega   43.00  108.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      108.9025  -95.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
  7 omega   49.00   74.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      108.9025  -45.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   41.00   66.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      108.9025  -30.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00  137.00   1.0000    2.4600
omega____ theta____ kappa____ phi______ frames
    -      108.9025  -15.0000  120.0000 103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0139419000
_diffrn_orient_matrix_UB_12      -0.0145989000
_diffrn_orient_matrix_UB_13      -0.0891138000
_diffrn_orient_matrix_UB_21      -0.1580294000
_diffrn_orient_matrix_UB_22      -0.0246594000
_diffrn_orient_matrix_UB_23      -0.0101576000
_diffrn_orient_matrix_UB_31      -0.0135745000
_diffrn_orient_matrix_UB_32      0.2993223000
_diffrn_orient_matrix_UB_33      -0.0052047000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.295
_reflns_Friedel_fraction_full    0.407
_reflns_Friedel_fraction_max     0.355
_reflns_number_gt                2345
_reflns_number_total             2518
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details 
;
 Flack x determined using 525 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2518
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.103
_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)+(0.1058P)²+0.5486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1691
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7A), N7(H7), C15(H15), C10(H10), C3(H3A), C2(H2), C9(H9),
 C16(H16), C8(H8), C11(H11), C1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.61302(15) -0.3774(3) -0.46517(8) 0.0238(4) Uani 1 1 d . . . . .
S1 S -0.63751(14) 1.3147(3) -0.01682(8) 0.0251(4) Uani 1 1 d . . . . .
O1 O -0.6224(4) 0.9482(10) -0.1268(3) 0.0294(10) Uani 1 1 d . . . . .
N3 N -0.8385(5) 1.1165(11) -0.1347(3) 0.0210(10) Uani 1 1 d . . . . .
H3 H -0.9253 1.1091 -0.1596 0.025 Uiso 1 1 calc R . . . .
N6 N -0.4203(5) 0.3492(11) -0.2489(3) 0.0229(11) Uani 1 1 d . . . . .
N2 N -0.9370(5) 0.7751(11) -0.2552(3) 0.0199(10) Uani 1 1 d . . . . .
C4 C -0.8028(6) 0.7640(13) -0.2203(3) 0.0214(12) Uani 1 1 d . . . . .
C12 C -0.3576(6) 0.1515(13) -0.2790(3) 0.0220(12) Uani 1 1 d . . . . .
N8 N -0.8004(5) -0.0787(11) -0.4273(3) 0.0241(11) Uani 1 1 d . . . . .
N1 N -0.7586(5) 0.3911(10) -0.2941(3) 0.0217(11) Uani 1 1 d . . . . .
N5 N -0.1358(5) 0.2543(11) -0.2025(3) 0.0235(11) Uani 1 1 d . . . . .
C7 C -0.8338(6) 1.6023(15) 0.0070(4) 0.0283(13) Uani 1 1 d . . . . .
H7A H -0.8848 1.7276 0.0295 0.034 Uiso 1 1 calc R . . . .
C6 C -0.8023(5) 1.2958(13) -0.0745(3) 0.0191(11) Uani 1 1 d . . . . .
N7 N -0.5786(5) 0.0168(10) -0.3561(3) 0.0204(10) Uani 1 1 d . . . . .
H7 H -0.6132 0.1397 -0.3306 0.025 Uiso 1 1 calc R . . . .
C15 C -0.7821(7) -0.4176(14) -0.5124(4) 0.0291(15) Uani 1 1 d . . . . .
H15 H -0.8132 -0.5414 -0.5525 0.035 Uiso 1 1 calc R . . . .
C10 C -0.1971(6) 0.4546(14) -0.1741(4) 0.0264(13) Uani 1 1 d . . . . .
H10 H -0.1425 0.5695 -0.1378 0.032 Uiso 1 1 calc R . . . .
C3 C -0.9796(6) 0.5942(13) -0.3094(3) 0.0212(12) Uani 1 1 d . . . . .
H3A H -1.0736 0.5962 -0.3360 0.025 Uiso 1 1 calc R . . . .
C14 C -0.6691(6) -0.1278(12) -0.4127(3) 0.0218(12) Uani 1 1 d . . . . .
C2 C -0.8926(6) 0.4021(12) -0.3287(3) 0.0219(12) Uani 1 1 d . . . . .
H2 H -0.9291 0.2763 -0.3673 0.026 Uiso 1 1 calc R . . . .
C5 C -0.7458(6) 0.9520(14) -0.1568(4) 0.0258(13) Uani 1 1 d . . . . .
C9 C -0.2169(6) 0.1072(14) -0.2552(3) 0.0241(13) Uani 1 1 d . . . . .
H9 H -0.1767 -0.0346 -0.2776 0.029 Uiso 1 1 calc R . . . .
C16 C -0.8639(6) -0.2488(14) -0.4845(4) 0.0273(14) Uani 1 1 d . . . . .
H16 H -0.9612 -0.2467 -0.5033 0.033 Uiso 1 1 calc R . . . .
N4 N -0.8932(5) 1.4539(12) -0.0566(3) 0.0248(11) Uani 1 1 d . . . . .
C13 C -0.4407(6) -0.0247(13) -0.3390(3) 0.0208(12) Uani 1 1 d . . . . .
C8 C -0.6980(7) 1.5572(13) 0.0351(4) 0.0260(13) Uani 1 1 d . . . . .
H8 H -0.6432 1.6475 0.0778 0.031 Uiso 1 1 calc R . . . .
C11 C -0.3385(6) 0.4990(14) -0.1963(4) 0.0261(13) Uani 1 1 d . . . . .
H11 H -0.3783 0.6402 -0.1735 0.031 Uiso 1 1 calc R . . . .
C1 C -0.7153(6) 0.5721(12) -0.2396(3) 0.0219(13) Uani 1 1 d . . . . .
H1 H -0.6213 0.5700 -0.2130 0.026 Uiso 1 1 calc R . . . .
O2 O -0.3828(4) -0.1952(10) -0.3698(2) 0.0266(9) Uani 1 1 d . . . . .


_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 C15 1.718(7) . ?
S2 C14 1.731(6) . ?
S1 C6 1.735(5) . ?
S1 C8 1.717(6) . ?
O1 C5 1.225(7) . ?
N3 C6 1.390(8) . ?
N3 C5 1.358(8) . ?
N6 C12 1.350(8) . ?
N6 C11 1.336(8) . ?
N2 C4 1.342(7) . ?
N2 C3 1.332(8) . ?
C4 C5 1.492(9) . ?
C4 C1 1.396(8) . ?
C12 C9 1.387(8) . ?
C12 C13 1.496(9) . ?
N8 C14 1.294(7) . ?
N8 C16 1.379(8) . ?
N1 C2 1.340(7) . ?
N1 C1 1.337(8) . ?
N5 C10 1.339(8) . ?
N5 C9 1.327(8) . ?
C7 N4 1.377(9) . ?
C7 C8 1.351(9) . ?
C6 N4 1.294(8) . ?
N7 C14 1.404(8) . ?
N7 C13 1.350(7) . ?
C15 C16 1.343(9) . ?
C10 C11 1.390(8) . ?
C3 C2 1.393(8) . ?
C13 O2 1.229(8) . ?

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
C15 S2 C14 87.7(3) . . ?
C8 S1 C6 87.9(3) . . ?
C5 N3 C6 122.9(5) . . ?
C11 N6 C12 116.1(5) . . ?
C3 N2 C4 115.8(5) . . ?
N2 C4 C5 120.0(5) . . ?
N2 C4 C1 121.4(6) . . ?
C1 C4 C5 118.5(5) . . ?
N6 C12 C9 121.1(6) . . ?
N6 C12 C13 119.9(5) . . ?
C9 C12 C13 119.0(6) . . ?
C14 N8 C16 108.0(5) . . ?
C1 N1 C2 115.9(5) . . ?
C9 N5 C10 116.1(5) . . ?
C8 C7 N4 115.3(6) . . ?
N3 C6 S1 123.0(4) . . ?
N4 C6 S1 116.0(4) . . ?
N4 C6 N3 121.0(5) . . ?
C13 N7 C14 122.8(5) . . ?
C16 C15 S2 110.2(5) . . ?
N5 C10 C11 121.8(6) . . ?
N2 C3 C2 123.0(5) . . ?
N8 C14 S2 117.1(5) . . ?
N8 C14 N7 120.3(5) . . ?
N7 C14 S2 122.6(4) . . ?
N1 C2 C3 121.4(6) . . ?
O1 C5 N3 123.8(6) . . ?
O1 C5 C4 120.0(6) . . ?
N3 C5 C4 116.1(5) . . ?
N5 C9 C12 122.8(6) . . ?
C15 C16 N8 117.0(6) . . ?
C6 N4 C7 109.9(5) . . ?
N7 C13 C12 116.4(5) . . ?
O2 C13 C12 120.0(5) . . ?
O2 C13 N7 123.6(5) . . ?
C7 C8 S1 110.9(5) . . ?
N6 C11 C10 122.0(6) . . ?
N1 C1 C4 122.6(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2114704'
loop_
_audit_author_name
_audit_author_address
'Alireza Salimi'
;Ferdowsi University of Mashhad
Iran
;
_audit_update_record             
;
2021-10-14 deposited with the CCDC.	2022-11-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H6 N4 O S'
_chemical_formula_weight         206.23

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   19.421(4)
_cell_length_b                   11.050(2)
_cell_length_c                   8.1836(16)
_cell_angle_alpha                90
_cell_angle_beta                 101.58(3)
_cell_angle_gamma                90
_cell_volume                     1720.4(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3100
_cell_measurement_theta_min      2.825
_cell_measurement_theta_max      25.247

_exptl_crystal_description       PLATE
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.343
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_reflns_number            8882
_diffrn_reflns_av_unetI/netI     0.2499
_diffrn_reflns_av_R_equivalents  0.2426
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.825
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3100
_reflns_number_gt                1448
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0544P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3100
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2322
_refine_ls_R_factor_gt           0.1225
_refine_ls_wR_factor_ref         0.2179
_refine_ls_wR_factor_gt          0.1831
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.1586(5) 0.2569(9) 1.1457(13) 0.019(2) Uani 1 1 d . . . . .
C2 C 0.2305(4) 0.1361(9) 1.3116(12) 0.0186(16) Uani 1 1 d . . . . .
H2 H 0.248369 0.062714 1.357097 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2598(5) 0.2459(8) 1.3679(13) 0.0186(16) Uani 1 1 d . . . . .
H3 H 0.299111 0.255117 1.453077 0.022 Uiso 1 1 calc R U . . .
C4 C 0.0868(4) 0.3995(8) 0.9683(12) 0.0182(14) Uani 1 1 d . . . . .
C5 C 0.0242(5) 0.4172(8) 0.8283(12) 0.0177(12) Uani 1 1 d . . . . .
C6 C -0.0722(5) 0.3422(8) 0.6516(13) 0.025(3) Uani 1 1 d . . . . .
H6 H -0.101270 0.277898 0.609308 0.030 Uiso 1 1 calc R U . . .
C7 C -0.0869(5) 0.4564(8) 0.5822(12) 0.015(2) Uani 1 1 d . . . . .
H7 H -0.126064 0.467522 0.497325 0.019 Uiso 1 1 calc R U . . .
C8 C 0.0094(4) 0.5294(8) 0.7581(12) 0.0177(12) Uani 1 1 d . . . . .
H8 H 0.039213 0.593446 0.797859 0.021 Uiso 1 1 calc R U . . .
N1 N 0.1741(4) 0.1432(7) 1.1856(10) 0.0178(18) Uani 1 1 d . . . . .
N2 N 0.1023(4) 0.2853(7) 1.0211(10) 0.0182(14) Uani 1 1 d . . . . .
H2N H 0.075676 0.227550 0.974705 0.022 Uiso 1 1 calc R U . . .
N3 N -0.0168(4) 0.3210(7) 0.7788(10) 0.0177(12) Uani 1 1 d . . . . .
N4 N -0.0451(4) 0.5505(7) 0.6366(10) 0.022(2) Uani 1 1 d . . . . .
O1 O 0.1205(3) 0.4890(6) 1.0314(9) 0.0221(16) Uani 1 1 d . . . . .
S1 S 0.21365(12) 0.3634(2) 1.2592(3) 0.0201(6) Uani 1 1 d . . . . .
C9 C 0.3391(5) 0.7742(8) 0.9877(13) 0.0160(14) Uani 1 1 d . . . . .
C10 C 0.2645(4) 0.6602(9) 1.0835(12) 0.0204(16) Uani 1 1 d . . . . .
H10 H 0.245105 0.587752 1.110486 0.024 Uiso 1 1 calc R U . . .
C11 C 0.2369(5) 0.7687(8) 1.1126(12) 0.0204(16) Uani 1 1 d . . . . .
H11 H 0.197645 0.779485 1.160056 0.024 Uiso 1 1 calc R U . . .
C12 C 0.4120(5) 0.9179(8) 0.8759(13) 0.021(2) Uani 1 1 d . . . . .
C13 C 0.4743(5) 0.9316(7) 0.7983(12) 0.015(2) Uani 1 1 d . . . . .
C14 C 0.5675(5) 0.8546(9) 0.7066(13) 0.0266(16) Uani 1 1 d . . . . .
H14 H 0.596119 0.789647 0.691988 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5848(5) 0.9676(8) 0.6560(12) 0.019(2) Uani 1 1 d . . . . .
H15 H 0.623795 0.976045 0.606981 0.023 Uiso 1 1 calc R U . . .
C16 C 0.4912(5) 1.0437(8) 0.7456(12) 0.019(2) Uani 1 1 d . . . . .
H16 H 0.462457 1.108763 0.759148 0.022 Uiso 1 1 calc R U . . .
N5 N 0.3229(4) 0.6627(7) 1.0119(11) 0.023(2) Uani 1 1 d . . . . .
N6 N 0.3957(4) 0.8037(7) 0.9157(10) 0.0160(14) Uani 1 1 d . . . . .
H6N H 0.422202 0.745825 0.894811 0.019 Uiso 1 1 calc R U . . .
N7 N 0.5115(4) 0.8333(7) 0.7759(11) 0.0266(16) Uani 1 1 d . . . . .
N8 N 0.5470(4) 1.0646(6) 0.6756(11) 0.022(2) Uani 1 1 d . . . . .
O2 O 0.3791(3) 1.0053(5) 0.9069(9) 0.0216(16) Uani 1 1 d . . . . .
S2 S 0.28549(12) 0.8841(2) 1.0485(3) 0.0220(6) Uani 1 1 d . . . . .


_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
C1 N1 1.318(12) . ?
C1 N2 1.373(12) . ?
C1 S1 1.730(10) . ?
C2 N1 1.347(11) . ?
C2 C3 1.379(13) . ?
C3 S1 1.721(9) . ?
C4 O1 1.239(10) . ?
C4 N2 1.349(12) . ?
C4 C5 1.507(12) . ?
C5 N3 1.342(11) . ?
C5 C8 1.372(13) . ?
C6 N3 1.358(12) . ?
C6 C7 1.390(12) . ?
C7 N4 1.339(12) . ?
C8 N4 1.320(11) . ?
C9 N5 1.297(11) . ?
C9 N6 1.386(12) . ?
C9 S2 1.737(9) . ?
C10 C11 1.354(14) . ?
C10 N5 1.376(13) . ?
C11 S2 1.730(10) . ?
C12 O2 1.212(10) . ?
C12 N6 1.355(12) . ?
C12 C13 1.484(14) . ?
C13 N7 1.337(11) . ?
C13 C16 1.373(12) . ?
C14 N7 1.345(13) . ?
C14 C15 1.378(14) . ?
C15 N8 1.327(12) . ?
C16 N8 1.344(13) . ?

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
N1 C1 N2 120.7(9) . . ?
N1 C1 S1 115.5(7) . . ?
N2 C1 S1 123.9(7) . . ?
N1 C2 C3 115.0(8) . . ?
C2 C3 S1 110.7(7) . . ?
O1 C4 N2 123.2(8) . . ?
O1 C4 C5 119.4(8) . . ?
N2 C4 C5 117.3(8) . . ?
N3 C5 C8 121.9(8) . . ?
N3 C5 C4 117.8(8) . . ?
C8 C5 C4 120.3(8) . . ?
N3 C6 C7 122.4(8) . . ?
N4 C7 C6 120.6(8) . . ?
N4 C8 C5 122.9(9) . . ?
C1 N1 C2 110.8(8) . . ?
C4 N2 C1 123.0(8) . . ?
C5 N3 C6 115.1(8) . . ?
C8 N4 C7 117.0(8) . . ?
C3 S1 C1 88.0(5) . . ?
N5 C9 N6 121.8(8) . . ?
N5 C9 S2 116.3(7) . . ?
N6 C9 S2 121.9(7) . . ?
C11 C10 N5 116.5(9) . . ?
C10 C11 S2 109.9(8) . . ?
O2 C12 N6 122.2(9) . . ?
O2 C12 C13 121.1(8) . . ?
N6 C12 C13 116.6(8) . . ?
N7 C13 C16 121.4(9) . . ?
N7 C13 C12 119.0(8) . . ?
C16 C13 C12 119.6(8) . . ?
N7 C14 C15 123.5(9) . . ?
N8 C15 C14 121.4(10) . . ?
N8 C16 C13 123.6(9) . . ?
C9 N5 C10 109.3(8) . . ?
C12 N6 C9 124.4(8) . . ?
C13 N7 C14 114.8(8) . . ?
C15 N8 C16 115.2(8) . . ?
C11 S2 C9 88.0(5) . . ?

_refine_diff_density_max         0.564
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.105



