# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_2
_audit_block_doi                 10.5517/ccdc.csd.cc1p47cf
_database_code_depnum_ccdc_archive 'CCDC 1553204'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/slct.201800719 2018
_audit_update_record             
;
2017-05-30 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.5-0'
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H6 N4 S2'
_chemical_formula_sum            'C14 H6 N4 S2'
_chemical_formula_weight         294.35

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'

_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   7.0827(3)
_cell_length_b                   18.8755(5)
_cell_length_c                   19.6605(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2628.40(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    26109
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    0.398
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6514
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.874
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            24122
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.394
_diffrn_reflns_theta_max         27.560
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3014
_reflns_number_gt                2477
_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       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Platon (Spek, 2009)'
_computing_publication_material  'Platon (Spek, 2009)'
_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)+(0.0499P)²+2.0204P] 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         3014
_refine_ls_number_parameters     194
_refine_ls_number_restraints     202
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.030
_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 0.8905(3) 0.38993(11) 0.65747(10) 0.0271(5) Uani 1 1 d . U . . .
N1 N 0.9308(4) 0.39385(12) 0.71349(9) 0.0440(6) Uani 1 1 d . U . . .
C2 C 0.8430(3) 0.51954(10) 0.58103(9) 0.0188(4) Uani 1 1 d . U . . .
N2 N 0.8833(3) 0.57325(9) 0.60409(9) 0.0264(4) Uani 1 1 d . U . . .
S2 S 0.62187(7) 0.46826(3) 0.34568(2) 0.02249(14) Uani 1 1 d . U . . .
N3 N 0.8345(2) 0.32587(8) 0.55448(8) 0.0193(3) Uani 1 1 d . U . . .
C3 C 0.8391(3) 0.38863(10) 0.58609(9) 0.0188(4) Uani 1 1 d . U . . .
C6 C 0.8038(3) 0.45100(10) 0.55095(9) 0.0165(4) Uani 1 1 d . U . . .
C5 C 0.7156(3) 0.38789(9) 0.45679(9) 0.0150(4) Uani 1 1 d . U . . .
N4 N 0.7374(2) 0.45075(8) 0.48749(7) 0.0166(3) Uani 1 1 d . U . . .
C4 C 0.7846(3) 0.32465(10) 0.48905(9) 0.0172(4) Uani 1 1 d . U . . .
C7 C 0.8094(3) 0.25644(10) 0.45524(9) 0.0182(4) Uani 1 1 d D U . . .
C11 C 0.6224(3) 0.38955(9) 0.39090(9) 0.0166(4) Uani 1 1 d . U . . .
C12 C 0.5196(3) 0.33820(11) 0.35714(10) 0.0224(4) Uani 1 1 d . U . . .
H12 H 0.5001 0.2916 0.3740 0.027 Uiso 1 1 calc R U . . .
C13 C 0.4467(3) 0.36326(12) 0.29455(10) 0.0284(5) Uani 1 1 d . U . . .
H13 H 0.3731 0.3350 0.2647 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4924(3) 0.43146(12) 0.28157(10) 0.0277(5) Uani 1 1 d . U . . .
H14 H 0.4566 0.4560 0.2414 0.033 Uiso 1 1 calc R U . . .
S1 S 0.89881(10) 0.24747(3) 0.37312(3) 0.0249(2) Uani 0.842(2) 1 d D U P A 1
C8 C 0.7875(4) 0.19066(14) 0.48382(16) 0.0169(5) Uani 0.842(2) 1 d D U P A 1
H8 H 0.7472 0.1837 0.5294 0.020 Uiso 0.842(2) 1 calc R U P A 1
C9 C 0.8300(15) 0.1343(2) 0.4394(2) 0.0220(8) Uani 0.842(2) 1 d D U P A 1
H9 H 0.8139 0.0858 0.4508 0.026 Uiso 0.842(2) 1 calc R U P A 1
C10 C 0.8967(6) 0.15727(18) 0.37868(17) 0.0238(8) Uani 0.842(2) 1 d D U P A 1
H10 H 0.9375 0.1266 0.3433 0.029 Uiso 0.842(2) 1 calc R U P A 1
S1A S 0.7687(8) 0.1850(2) 0.5063(2) 0.0249(2) Uani 0.158(2) 1 d D U P A 2
C8A C 0.852(2) 0.2382(7) 0.3893(4) 0.0169(5) Uani 0.158(2) 1 d D U P A 2
H8A H 0.8722 0.2711 0.3534 0.020 Uiso 0.158(2) 1 calc R U P A 2
C9A C 0.862(4) 0.1646(8) 0.3821(7) 0.0220(8) Uani 0.158(2) 1 d D U P A 2
H9A H 0.8808 0.1406 0.3402 0.026 Uiso 0.158(2) 1 calc R U P A 2
C10A C 0.842(9) 0.1310(10) 0.4451(10) 0.0238(8) Uani 0.158(2) 1 d D U P A 2
H10A H 0.8676 0.0822 0.4522 0.029 Uiso 0.158(2) 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
C1 0.0341(13) 0.0291(11) 0.0182(10) 0.0001(8) 0.0008(8) 0.0018(9)
N1 0.0618(15) 0.0519(13) 0.0183(9) -0.0003(9) -0.0057(9) 0.0006(11)
C2 0.0164(10) 0.0250(10) 0.0151(8) -0.0015(7) 0.0022(7) 0.0003(8)
N2 0.0250(10) 0.0282(9) 0.0262(9) -0.0078(7) 0.0008(7) -0.0024(7)
S2 0.0249(3) 0.0248(3) 0.0178(2) 0.00491(19) -0.00109(19) 0.0015(2)
N3 0.0219(9) 0.0210(8) 0.0151(7) 0.0013(6) 0.0007(6) 0.0016(7)
C3 0.0178(10) 0.0252(9) 0.0134(8) -0.0002(7) 0.0006(7) 0.0011(8)
C6 0.0138(9) 0.0204(9) 0.0154(8) -0.0031(7) 0.0024(7) -0.0015(7)
C5 0.0151(9) 0.0163(8) 0.0138(8) 0.0004(7) 0.0032(7) 0.0006(7)
N4 0.0168(8) 0.0166(7) 0.0164(7) -0.0014(6) 0.0003(6) 0.0003(6)
C4 0.0178(9) 0.0185(9) 0.0154(8) 0.0006(7) 0.0015(7) -0.0008(7)
C7 0.0202(10) 0.0200(9) 0.0146(8) -0.0005(7) -0.0016(7) 0.0032(8)
C11 0.0169(9) 0.0180(8) 0.0149(8) -0.0001(7) 0.0005(7) 0.0035(7)
C12 0.0233(11) 0.0223(9) 0.0217(9) -0.0061(8) -0.0025(8) 0.0035(8)
C13 0.0240(11) 0.0396(12) 0.0216(10) -0.0121(9) -0.0052(8) 0.0036(9)
C14 0.0255(12) 0.0429(13) 0.0147(9) 0.0020(8) -0.0040(8) 0.0076(9)
S1 0.0390(5) 0.0198(3) 0.0158(3) 0.0017(2) 0.0052(3) 0.0074(3)
C8 0.0161(12) 0.0210(12) 0.0136(12) 0.0001(10) 0.0010(10) -0.0017(9)
C9 0.023(2) 0.0177(11) 0.0250(13) -0.0002(9) -0.0068(15) 0.0025(11)
C10 0.026(2) 0.0239(13) 0.0211(11) -0.0052(10) -0.0031(10) 0.0083(11)
S1A 0.0390(5) 0.0198(3) 0.0158(3) 0.0017(2) 0.0052(3) 0.0074(3)
C8A 0.0161(12) 0.0210(12) 0.0136(12) 0.0001(10) 0.0010(10) -0.0017(9)
C9A 0.023(2) 0.0177(11) 0.0250(13) -0.0002(9) -0.0068(15) 0.0025(11)
C10A 0.026(2) 0.0239(13) 0.0211(11) -0.0052(10) -0.0031(10) 0.0083(11)

_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 1.140(3) . ?
C1 C3 1.450(3) . ?
C2 N2 1.147(3) . ?
C2 C6 1.449(3) . ?
S2 C14 1.707(2) . ?
S2 C11 1.7313(18) . ?
N3 C4 1.334(2) . ?
N3 C3 1.338(2) . ?
C3 C6 1.388(3) . ?
C6 N4 1.333(2) . ?
C5 N4 1.340(2) . ?
C5 C4 1.437(2) . ?
C5 C11 1.454(2) . ?
C4 C7 1.460(3) . ?
C7 C8 1.372(3) . ?
C7 C8A 1.376(8) . ?
C7 S1A 1.705(5) . ?
C7 S1 1.7424(19) . ?
C11 C12 1.382(3) . ?
C12 C13 1.416(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.352(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
S1 C10 1.706(3) . ?
C8 C9 1.408(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.355(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
S1A C10A 1.66(3) . ?
C8A C9A 1.397(9) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.398(7) . ?
C9A H9A 0.9500 . ?
C10A H10A 0.9500 . ?

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 C3 177.2(2) . . ?
N2 C2 C6 176.6(2) . . ?
C14 S2 C11 91.79(10) . . ?
C4 N3 C3 118.00(16) . . ?
N3 C3 C6 121.02(17) . . ?
N3 C3 C1 118.07(17) . . ?
C6 C3 C1 120.85(18) . . ?
N4 C6 C3 121.77(17) . . ?
N4 C6 C2 116.90(16) . . ?
C3 C6 C2 121.31(17) . . ?
N4 C5 C4 119.81(16) . . ?
N4 C5 C11 115.76(16) . . ?
C4 C5 C11 124.42(16) . . ?
C6 N4 C5 117.73(16) . . ?
N3 C4 C5 120.09(16) . . ?
N3 C4 C7 114.98(16) . . ?
C5 C4 C7 124.92(16) . . ?
C8 C7 C4 126.7(2) . . ?
C8A C7 C4 132.6(5) . . ?
C8A C7 S1A 113.2(5) . . ?
C4 C7 S1A 114.13(19) . . ?
C8 C7 S1 109.44(17) . . ?
C4 C7 S1 123.48(14) . . ?
C12 C11 C5 130.68(17) . . ?
C12 C11 S2 110.73(14) . . ?
C5 C11 S2 118.49(13) . . ?
C11 C12 C13 112.04(19) . . ?
C11 C12 H12 124.0 . . ?
C13 C12 H12 124.0 . . ?
C14 C13 C12 113.28(19) . . ?
C14 C13 H13 123.4 . . ?
C12 C13 H13 123.4 . . ?
C13 C14 S2 112.13(15) . . ?
C13 C14 H14 123.9 . . ?
S2 C14 H14 123.9 . . ?
C10 S1 C7 91.97(12) . . ?
C7 C8 C9 113.9(3) . . ?
C7 C8 H8 123.0 . . ?
C9 C8 H8 123.0 . . ?
C10 C9 C8 112.3(3) . . ?
C10 C9 H9 123.8 . . ?
C8 C9 H9 123.8 . . ?
C9 C10 S1 112.2(3) . . ?
C9 C10 H10 123.9 . . ?
S1 C10 H10 123.9 . . ?
C10A S1A C7 90.3(6) . . ?
C7 C8A C9A 110.8(7) . . ?
C7 C8A H8A 124.6 . . ?
C9A C8A H8A 124.6 . . ?
C8A C9A C10A 110.9(10) . . ?
C8A C9A H9A 124.6 . . ?
C10A C9A H9A 124.6 . . ?
C9A C10A S1A 113.3(13) . . ?
C9A C10A H10A 123.3 . . ?
S1A C10A H10A 123.3 . . ?

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.065
####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc1p47bd
_database_code_depnum_ccdc_archive 'CCDC 1553203'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/slct.201800719 2018
_audit_update_record             
;
2017-05-30 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.5-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 N4 O2 S2'
_chemical_formula_sum            'C16 H10 N4 O2 S2'
_chemical_formula_weight         354.40

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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   16.8041(5)
_cell_length_b                   8.1400(3)
_cell_length_c                   23.1477(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3166.27(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    52177
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7137
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.956
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            48761
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.137
_diffrn_reflns_theta_max         34.067
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6491
_reflns_number_gt                5192
_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       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Platon (Spek, 2009)'
_computing_publication_material  'Platon (Spek, 2009)'
_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)+(0.0461P)²+1.2585P] 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         6491
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.002
_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
S1 S 0.37548(2) 0.44494(4) 0.36564(2) 0.02055(7) Uani 1 1 d . . . . .
C1 C 0.64932(7) 0.26064(16) 0.34142(5) 0.0232(2) Uani 1 1 d . . . . .
O1 O 0.21830(5) 0.48958(12) 0.34396(4) 0.02499(18) Uani 1 1 d . . . . .
N1 N 0.68983(8) 0.28116(17) 0.30232(5) 0.0360(3) Uani 1 1 d . . . . .
O2 O 0.46144(6) 0.16078(14) 0.70858(4) 0.0312(2) Uani 1 1 d . . . . .
S2 S 0.52716(2) 0.12626(3) 0.60199(2) 0.01750(7) Uani 1 1 d . . . . .
C2 C 0.59914(6) 0.23576(14) 0.39121(5) 0.01765(19) Uani 1 1 d . . . . .
N2 N 0.75267(7) -0.03198(14) 0.43320(5) 0.0275(2) Uani 1 1 d . . . . .
N3 N 0.52639(5) 0.30145(12) 0.38999(4) 0.01794(17) Uani 1 1 d . . . . .
C3 C 0.47948(6) 0.28471(13) 0.43650(5) 0.01596(18) Uani 1 1 d . . . . .
N4 N 0.58356(5) 0.14355(12) 0.48766(4) 0.01669(17) Uani 1 1 d . . . . .
C4 C 0.51347(6) 0.22246(13) 0.48960(4) 0.01525(18) Uani 1 1 d . . . . .
C9 C 0.25821(7) 0.32840(16) 0.42555(5) 0.0212(2) Uani 1 1 d . . . . .
H9 H 0.2061 0.3022 0.4384 0.025 Uiso 1 1 calc R U . . .
C8 C 0.32809(7) 0.27515(15) 0.45293(5) 0.0206(2) Uani 1 1 d . . . . .
H8 H 0.3278 0.2081 0.4865 0.025 Uiso 1 1 calc R U . . .
C7 C 0.39711(6) 0.32860(14) 0.42687(5) 0.01718(19) Uani 1 1 d . . . . .
C6 C 0.69686(7) 0.04789(15) 0.43586(5) 0.0197(2) Uani 1 1 d . . . . .
C5 C 0.62476(6) 0.14422(14) 0.43823(5) 0.01684(19) Uani 1 1 d . . . . .
C10 C 0.27434(7) 0.42288(15) 0.37792(5) 0.0187(2) Uani 1 1 d . . . . .
C11 C 0.24639(8) 0.57978(17) 0.29457(5) 0.0266(2) Uani 1 1 d . . . . .
H11A H 0.2733 0.5046 0.2679 0.040 Uiso 1 1 calc R U . . .
H11B H 0.2838 0.6647 0.3072 0.040 Uiso 1 1 calc R U . . .
H11C H 0.2012 0.6315 0.2749 0.040 Uiso 1 1 calc R U . . .
C12 C 0.48006(6) 0.23649(14) 0.54713(4) 0.01633(18) Uani 1 1 d . . . . .
C13 C 0.41854(7) 0.32971(15) 0.56907(5) 0.0201(2) Uani 1 1 d . . . . .
H13 H 0.3870 0.4008 0.5459 0.024 Uiso 1 1 calc R U . . .
C14 C 0.40674(7) 0.30997(16) 0.62882(5) 0.0233(2) Uani 1 1 d . . . . .
H14 H 0.3664 0.3647 0.6502 0.028 Uiso 1 1 calc R U . . .
C15 C 0.46025(7) 0.20250(15) 0.65241(5) 0.0207(2) Uani 1 1 d . . . . .
C16 C 0.51993(10) 0.0430(2) 0.72649(6) 0.0371(3) Uani 1 1 d . . . . .
H16A H 0.5733 0.0856 0.7181 0.056 Uiso 1 1 calc R U . . .
H16B H 0.5117 -0.0602 0.7055 0.056 Uiso 1 1 calc R U . . .
H16C H 0.5148 0.0233 0.7681 0.056 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 0.01757(12) 0.02427(14) 0.01982(12) 0.00606(10) 0.00108(9) -0.00183(10)
C1 0.0238(5) 0.0260(6) 0.0198(5) 0.0002(4) 0.0033(4) -0.0005(4)
O1 0.0207(4) 0.0307(5) 0.0236(4) 0.0052(3) -0.0037(3) 0.0010(3)
N1 0.0388(6) 0.0426(7) 0.0266(5) 0.0016(5) 0.0127(5) -0.0008(6)
O2 0.0351(5) 0.0427(6) 0.0156(4) 0.0017(4) 0.0030(3) 0.0057(4)
S2 0.01719(12) 0.01951(13) 0.01580(11) -0.00129(9) -0.00034(8) 0.00008(9)
C2 0.0166(4) 0.0195(5) 0.0168(4) -0.0016(4) 0.0029(3) -0.0040(4)
N2 0.0208(4) 0.0289(5) 0.0326(5) -0.0010(4) 0.0052(4) 0.0009(4)
N3 0.0175(4) 0.0185(4) 0.0178(4) 0.0006(3) 0.0018(3) -0.0027(3)
C3 0.0160(4) 0.0147(4) 0.0171(4) -0.0004(3) 0.0006(3) -0.0023(4)
N4 0.0143(4) 0.0187(4) 0.0171(4) -0.0015(3) 0.0017(3) -0.0017(3)
C4 0.0148(4) 0.0152(4) 0.0158(4) -0.0012(3) 0.0005(3) -0.0027(3)
C9 0.0167(4) 0.0289(6) 0.0180(4) 0.0016(4) 0.0012(4) -0.0029(4)
C8 0.0186(5) 0.0252(5) 0.0180(5) 0.0039(4) -0.0002(4) -0.0038(4)
C7 0.0172(4) 0.0182(5) 0.0161(4) 0.0014(4) -0.0005(3) -0.0010(4)
C6 0.0175(4) 0.0225(5) 0.0191(5) -0.0005(4) 0.0027(4) -0.0026(4)
C5 0.0142(4) 0.0185(5) 0.0179(4) -0.0023(4) 0.0016(3) -0.0030(4)
C10 0.0168(4) 0.0211(5) 0.0180(4) -0.0013(4) -0.0004(3) -0.0001(4)
C11 0.0318(6) 0.0268(6) 0.0212(5) 0.0036(4) -0.0040(5) 0.0015(5)
C12 0.0168(4) 0.0167(5) 0.0155(4) -0.0015(3) 0.0002(3) -0.0013(4)
C13 0.0203(5) 0.0199(5) 0.0199(5) -0.0030(4) 0.0004(4) 0.0025(4)
C14 0.0229(5) 0.0279(6) 0.0192(5) -0.0048(4) 0.0030(4) 0.0037(5)
C15 0.0225(5) 0.0243(5) 0.0153(4) -0.0032(4) 0.0018(4) -0.0027(4)
C16 0.0417(8) 0.0481(9) 0.0214(6) 0.0059(6) -0.0041(5) 0.0060(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
S1 C10 1.7325(11) . ?
S1 C7 1.7429(11) . ?
C1 N1 1.1448(16) . ?
C1 C2 1.4423(15) . ?
O1 C10 1.3413(14) . ?
O1 C11 1.4384(16) . ?
O2 C15 1.3440(14) . ?
O2 C16 1.4341(18) . ?
S2 C15 1.7355(12) . ?
S2 C12 1.7447(11) . ?
C2 N3 1.3345(14) . ?
C2 C5 1.3876(16) . ?
N2 C6 1.1428(16) . ?
N3 C3 1.3413(13) . ?
C3 C7 1.4467(15) . ?
C3 C4 1.4471(15) . ?
N4 C5 1.3374(14) . ?
N4 C4 1.3423(14) . ?
C4 C12 1.4495(14) . ?
C9 C10 1.3714(16) . ?
C9 C8 1.4030(16) . ?
C9 H9 0.9500 . ?
C8 C7 1.3778(15) . ?
C8 H8 0.9500 . ?
C6 C5 1.4443(15) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.3794(15) . ?
C13 C14 1.4063(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3683(18) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 S1 C7 90.85(5) . . ?
N1 C1 C2 179.19(15) . . ?
C10 O1 C11 116.24(10) . . ?
C15 O2 C16 117.31(10) . . ?
C15 S2 C12 90.67(5) . . ?
N3 C2 C5 121.06(10) . . ?
N3 C2 C1 117.54(10) . . ?
C5 C2 C1 121.39(10) . . ?
C2 N3 C3 118.74(10) . . ?
N3 C3 C7 114.43(9) . . ?
N3 C3 C4 119.03(9) . . ?
C7 C3 C4 126.52(9) . . ?
C5 N4 C4 118.74(10) . . ?
N4 C4 C3 119.05(9) . . ?
N4 C4 C12 114.09(9) . . ?
C3 C4 C12 126.86(9) . . ?
C10 C9 C8 111.78(10) . . ?
C10 C9 H9 124.1 . . ?
C8 C9 H9 124.1 . . ?
C7 C8 C9 114.16(10) . . ?
C7 C8 H8 122.9 . . ?
C9 C8 H8 122.9 . . ?
C8 C7 C3 131.29(10) . . ?
C8 C7 S1 110.61(8) . . ?
C3 C7 S1 117.32(8) . . ?
N2 C6 C5 177.97(13) . . ?
N4 C5 C2 120.85(10) . . ?
N4 C5 C6 117.69(10) . . ?
C2 C5 C6 121.47(10) . . ?
O1 C10 C9 124.02(10) . . ?
O1 C10 S1 123.40(9) . . ?
C9 C10 S1 112.58(9) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C4 132.21(10) . . ?
C13 C12 S2 110.78(8) . . ?
C4 C12 S2 116.90(8) . . ?
C12 C13 C14 113.89(11) . . ?
C12 C13 H13 123.1 . . ?
C14 C13 H13 123.1 . . ?
C15 C14 C13 111.89(10) . . ?
C15 C14 H14 124.1 . . ?
C13 C14 H14 124.1 . . ?
O2 C15 C14 123.88(11) . . ?
O2 C15 S2 123.41(9) . . ?
C14 C15 S2 112.70(9) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.460
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1897538'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.5-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 N4 O2'
_chemical_formula_sum            'C8 H6 N4 O2'
_chemical_formula_weight         190.17

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   9.3323(7)
_cell_length_b                   14.8768(11)
_cell_length_c                   6.3126(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     876.41(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8519
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            'translucent colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6553
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.879
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            7842
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.506
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1043
_reflns_number_gt                826
_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       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Platon (Spek, 2009)'
_computing_publication_material  'Platon (Spek, 2009)'
_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)+(0.0580P)²+0.1812P] 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         1043
_refine_ls_number_parameters     65
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
O1 O 0.20140(11) 0.33803(6) 0.12385(15) 0.0232(3) Uani 1 1 d . . . . .
C1 C 0.39526(14) 0.29614(9) 0.58811(19) 0.0186(3) Uani 1 1 d . . . . .
N1 N 0.33281(12) 0.34456(7) 0.43185(18) 0.0195(3) Uani 1 1 d . . . . .
N2 N 0.51584(15) 0.38298(10) 0.8949(2) 0.0366(4) Uani 1 1 d . . . . .
C2 C 0.26966(14) 0.29857(9) 0.2825(2) 0.0183(3) Uani 1 1 d . . . . .
C3 C 0.46277(16) 0.34515(10) 0.7578(2) 0.0238(3) Uani 1 1 d . . . . .
C4 C 0.19591(17) 0.43570(9) 0.1295(2) 0.0267(4) Uani 1 1 d . . . . .
H4A H 0.2936 0.4598 0.1289 0.040 Uiso 1 1 calc R U . . .
H4B H 0.1464 0.4552 0.2584 0.040 Uiso 1 1 calc R U . . .
H4C H 0.1440 0.4578 0.0050 0.040 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
O1 0.0293(6) 0.0171(5) 0.0232(5) 0.0029(4) -0.0070(4) 0.0003(4)
C1 0.0145(6) 0.0230(7) 0.0183(7) -0.0018(5) 0.0009(5) -0.0004(5)
N1 0.0189(6) 0.0186(6) 0.0210(6) -0.0002(4) -0.0002(5) -0.0008(5)
N2 0.0347(8) 0.0415(8) 0.0335(7) -0.0113(6) -0.0095(6) -0.0002(6)
C2 0.0162(7) 0.0200(7) 0.0188(7) 0.0006(5) 0.0009(5) 0.0002(5)
C3 0.0212(7) 0.0262(7) 0.0241(7) -0.0007(6) -0.0015(6) 0.0015(6)
C4 0.0364(8) 0.0166(7) 0.0270(7) 0.0037(6) -0.0051(6) 0.0015(6)

_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
O1 C2 1.3244(16) . ?
O1 C4 1.4544(16) . ?
C1 N1 1.3534(17) . ?
C1 C1 1.373(3) 7_565 ?
C1 C3 1.4408(19) . ?
N1 C2 1.3052(17) . ?
N2 C3 1.1453(19) . ?
C2 C2 1.445(3) 7_565 ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?

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
C2 O1 C4 116.19(11) . . ?
N1 C1 C1 122.16(7) . 7_565 ?
N1 C1 C3 117.44(12) . . ?
C1 C1 C3 120.41(8) 7_565 . ?
C2 N1 C1 116.22(11) . . ?
N1 C2 O1 122.08(12) . . ?
N1 C2 C2 121.61(8) . 7_565 ?
O1 C2 C2 116.31(7) . 7_565 ?
N2 C3 C1 178.85(16) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045

_shelx_res_file                  
;

    mo_jty180108N1_0ma_a.res created by SHELXL-2014/7


TITL mo_jty180108N1_0ma_a.res in Pnma
REM Old TITL mo_jty180108N1_0ma in Pnma

REM SHELXT solution in Pnma
REM R1 0.104,  Rweak 0.003,  Alpha 0.025,  Orientation as input
REM Formula found by SHELXT:  C4 N2 O

CELL  0.71073   9.3323  14.8768   6.3126   90.000   90.000   90.000
ZERR   4.000   0.0007   0.0011   0.0005    0.000    0.000    0.000
LATT  1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, -Z
SYMM 1/2+X, 1/2-Y, 1/2-Z
SFAC C H N O
UNIT 32 24 16 8
ACTA
TEMP -123.170
L.S. 10
BOND $H
LIST 6
FMAP 2
PLAN 20
WGHT    0.058000    0.181200
FVAR       1.34311
O1    4    0.201398    0.338029    0.123848    11.00000    0.02934    0.01712 =
         0.02322    0.00285   -0.00700    0.00035
C1    1    0.395259    0.296138    0.588114    11.00000    0.01448    0.02298 =
         0.01834   -0.00182    0.00092   -0.00035
N1    3    0.332807    0.344555    0.431845    11.00000    0.01887    0.01862 =
         0.02101   -0.00025   -0.00015   -0.00081
N2    3    0.515838    0.382982    0.894945    11.00000    0.03472    0.04148 =
         0.03350   -0.01128   -0.00950   -0.00020
C2    1    0.269657    0.298569    0.282545    11.00000    0.01616    0.02002 =
         0.01879    0.00061    0.00092    0.00015
C3    1    0.462772    0.345154    0.757784    11.00000    0.02115    0.02625 =
         0.02412   -0.00073   -0.00147    0.00146
C4    1    0.195906    0.435699    0.129485    11.00000    0.03645    0.01664 =
         0.02705    0.00374   -0.00505    0.00150
AFIX 137
H4A   2    0.293607    0.459846    0.128895    11.00000   -1.50000
H4B   2    0.146365    0.455242    0.258387    11.00000   -1.50000
H4C   2    0.144044    0.457824    0.004969    11.00000   -1.50000
AFIX   0
HKLF 4

REM  mo_jty180108N1_0ma_a.res in Pnma
REM R1 =  0.0431 for     826 Fo > 4sig(Fo)  and  0.0606 for all    1043 data
REM     65 parameters refined using      0 restraints

END

WGHT      0.0581      0.1665

REM Highest difference peak  0.310,  deepest hole -0.235,  1-sigma level  0.045
Q1    1   0.2653  0.2500  0.2825  10.50000  0.05    0.31
Q2    1   0.4105  0.2500  0.5738  10.50000  0.05    0.24
Q3    1   0.5031  0.2500  0.9782  10.50000  0.05    0.16
Q4    1   0.1782  0.4380 -0.0421  11.00000  0.05    0.16
Q5    1   0.3846  0.4070  0.4514  11.00000  0.05    0.15
Q6    1   0.1205  0.2500  0.0414  10.50000  0.05    0.15
Q7    1   0.5093  0.3221  0.8809  11.00000  0.05    0.14
Q8    1   0.3054  0.3990  0.4537  11.00000  0.05    0.14
Q9    1   0.5751  0.4117  1.0024  11.00000  0.05    0.14
Q10   1   0.3318  0.3134  0.3202  11.00000  0.05    0.13
Q11   1   0.4597  0.3190  0.6370  11.00000  0.05    0.13
Q12   1   0.4858  0.3865  0.7625  11.00000  0.05    0.12
Q13   1   0.2620  0.3227  0.4000  11.00000  0.05    0.12
Q14   1   0.5419  0.3413  0.7458  11.00000  0.05    0.12
Q15   1   0.3396  0.3164  0.5419  11.00000  0.05    0.12
Q16   1   0.1991  0.2500 -0.1894  10.50000  0.05    0.12
Q17   1   0.3840  0.2500  0.9682  10.50000  0.05    0.12
Q18   1   0.4005  0.3138  0.4923  11.00000  0.05    0.11
Q19   1   0.1211  0.3209  0.0723  11.00000  0.05    0.11
Q20   1   0.4089  0.3123  0.6886  11.00000  0.05    0.11
;
_shelx_res_checksum              84855
####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 1897540'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H6 N6'
_chemical_formula_weight         222.22

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_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'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   3.7497(5)
_cell_length_b                   14.1534(17)
_cell_length_c                   10.3386(13)
_cell_angle_alpha                90
_cell_angle_beta                 97.855(4)
_cell_angle_gamma                90
_cell_volume                     543.53(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6571
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             228
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.081
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6744
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_special_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction.
The ratio of minimum to maximum
apparent transmission was 0.905
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            6571
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.455
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1287
_reflns_number_gt                1009
_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       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Platon (Spek, 2009)'
_computing_publication_material  'Platon (Spek, 2009)'
_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)+(0.0449P)²+0.4732P] 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         1287
_refine_ls_number_parameters     85
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1462
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_restrained_S_all      1.197
_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
N1 N 1.2243(6) 0.7500 0.7211(2) 0.0215(5) Uani 1 2 d S T P . .
C1 C 0.1551(6) 0.66750(16) 0.1808(2) 0.0307(5) Uani 1 1 d . . . . .
H1 H 0.2277 0.6098 0.2234 0.037 Uiso 1 1 calc R U . . .
C2 C -0.0438(7) 0.66665(18) 0.0605(2) 0.0361(6) Uani 1 1 d . . . . .
H2 H -0.1138 0.6082 0.0194 0.043 Uiso 1 1 calc R U . . .
N2 N 0.7455(6) 0.63317(18) 0.4512(2) 0.0450(6) Uani 1 1 d . . . . .
C3 C -0.1430(8) 0.7500 -0.0012(3) 0.0335(8) Uani 1 2 d S T P . .
H3 H -0.2789 0.7500 -0.0858 0.040 Uiso 1 2 calc R U P . .
N3 N 1.4000(7) 0.52657(16) 0.8127(2) 0.0482(6) Uani 1 1 d . . . . .
C4 C 1.1358(6) 0.66610(15) 0.6718(2) 0.0253(5) Uani 1 1 d . . . . .
N4 N 0.2479(8) 0.7500 0.2389(3) 0.0366(7) Uani 1 2 d S T P . .
H4 H 0.396(12) 0.7500 0.329(5) 0.060(13) Uiso 1 2 d S . P . .
C5 C 0.9191(6) 0.64659(16) 0.5491(2) 0.0285(5) Uani 1 1 d . . . . .
C6 C 1.2810(6) 0.58749(16) 0.7483(2) 0.0310(5) Uani 1 1 d . . . . .

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
N1 0.0159(12) 0.0299(13) 0.0183(12) 0.000 0.0012(9) 0.000
C1 0.0323(12) 0.0259(12) 0.0351(12) 0.0094(10) 0.0083(10) 0.0058(10)
C2 0.0376(13) 0.0353(14) 0.0373(13) -0.0124(11) 0.0125(11) -0.0126(11)
N2 0.0449(13) 0.0576(15) 0.0298(11) -0.0074(10) -0.0043(9) -0.0124(11)
C3 0.0185(15) 0.066(2) 0.0149(14) 0.000 0.0000(12) 0.000
N3 0.0584(15) 0.0304(12) 0.0511(14) 0.0061(11) -0.0096(12) -0.0056(11)
C4 0.0222(11) 0.0319(12) 0.0210(10) -0.0005(9) 0.0003(8) -0.0039(9)
N4 0.0225(15) 0.060(2) 0.0258(15) 0.000 -0.0018(12) 0.000
C5 0.0272(11) 0.0325(12) 0.0259(11) -0.0024(9) 0.0040(9) -0.0055(9)
C6 0.0323(13) 0.0287(12) 0.0305(12) -0.0030(9) -0.0006(10) -0.0063(10)

_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
N1 C4 1.317(2) . ?
N1 C4 1.317(2) 4_575 ?
C1 N4 1.337(3) . ?
C1 C2 1.360(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.369(3) . ?
C2 H2 0.9500 . ?
N2 C5 1.142(3) . ?
C3 C2 1.369(3) 4_575 ?
C3 H3 0.9500 . ?
N3 C6 1.143(3) . ?
C4 C6 1.429(3) . ?
C4 C5 1.437(3) . ?
N4 C1 1.337(3) 4_575 ?
N4 H4 1.02(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
C4 N1 C4 128.8(3) . 4_575 ?
N4 C1 C2 119.7(2) . . ?
N4 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C2 119.1(3) 4_575 . ?
C2 C3 H3 120.5 4_575 . ?
C2 C3 H3 120.5 . . ?
N1 C4 C6 115.55(19) . . ?
N1 C4 C5 126.7(2) . . ?
C6 C4 C5 117.8(2) . . ?
C1 N4 C1 121.7(3) 4_575 . ?
C1 N4 H4 119.17(15) 4_575 . ?
C1 N4 H4 119.17(14) . . ?
N2 C5 C4 178.5(3) . . ?
N3 C6 C4 177.8(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 N3 0.95 2.44 3.210(3) 138.0 3_766
N4 H4 N2 1.02(5) 2.36(3) 3.149(3) 133.0(13) .
N4 H4 N2 1.02(5) 2.36(3) 3.149(3) 133.0(13) 4_575

_refine_diff_density_max         0.201
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.056

_shelx_res_file                  
;

    mo_fb170320S1_0m_a.res created by SHELXL-2014/7


TITL mo_fb170320S1_0m_a.res in P2(1)/m
REM Old TITL mo_fb170320S1_0m in P2/m
REM SHELXT solution in P2(1)/m
REM R1 0.142,  Rweak 0.021,  Alpha 0.030,  Orientation as input
REM Formula found by SHELXT:  C12 N5
CELL  0.71073   3.7497  14.1534  10.3386   90.000   97.855   90.000
ZERR    2.000   0.0005   0.0017   0.0013    0.000    0.004    0.000
LATT  1
SYMM -X, 1/2+Y, -Z
SFAC C H N
UNIT 22 12 12
ACTA
TEMP -123.160
L.S. 10
BOND $H
HTAB
EQIV $1 -x+2, -y+1, -z+1
EQIV $2 x, -y+3/2, z
HTAB C1 N3_$1
HTAB N4 N2
HTAB N4 N2_$2
LIST 6
FMAP 2
PLAN 20
WGHT    0.044900    0.473200
FVAR       1.00047
N1    3    1.224287    0.750000    0.721059    10.50000    0.01588    0.02991 =
         0.01830    0.00000    0.00120    0.00000
C1    1    0.155058    0.667502    0.180829    11.00000    0.03227    0.02588 =
         0.03511    0.00941    0.00835    0.00581
AFIX  43
H1    2    0.227677    0.609773    0.223377    11.00000   -1.20000
AFIX   0
C2    1   -0.043830    0.666649    0.060533    11.00000    0.03764    0.03531 =
         0.03730   -0.01242    0.01250   -0.01260
AFIX  43
H2    2   -0.113828    0.608242    0.019411    11.00000   -1.20000
AFIX   0
N2    3    0.745531    0.633169    0.451201    11.00000    0.04492    0.05763 =
         0.02983   -0.00742   -0.00427   -0.01236
C3    1   -0.143050    0.750000   -0.001232    10.50000    0.01851    0.06640 =
         0.01486    0.00000   -0.00001    0.00000
AFIX  43
H3    2   -0.278926    0.750000   -0.085815    10.50000   -1.20000
AFIX   0
N3    3    1.399983    0.526575    0.812743    11.00000    0.05841    0.03040 =
         0.05106    0.00607   -0.00963   -0.00564
C4    1    1.135845    0.666101    0.671768    11.00000    0.02223    0.03189 =
         0.02099   -0.00047    0.00032   -0.00386
N4    3    0.247893    0.750000    0.238925    10.50000    0.02250    0.06010 =
         0.02581    0.00000   -0.00177    0.00000
H4    2    0.395768    0.750000    0.329231    10.50000    0.05966
C5    1    0.919121    0.646594    0.549063    11.00000    0.02720    0.03254 =
         0.02589   -0.00241    0.00402   -0.00549
C6    1    1.281046    0.587486    0.748253    11.00000    0.03230    0.02872 =
         0.03046   -0.00297   -0.00062   -0.00631
HKLF 4

REM  mo_fb170320S1_0m_a.res in P2(1)/m
REM R1 =  0.0644 for    1009 Fo > 4sig(Fo)  and  0.0841 for all    1287 data
REM     85 parameters refined using      0 restraints

END

WGHT      0.0449      0.4732

REM Instructions for potential hydrogen bonds
HTAB C1 N3_$1
HTAB N4 N2
HTAB N4 N2_$2

REM Highest difference peak  0.201,  deepest hole -0.435,  1-sigma level  0.056
Q1    1   0.1570  0.6544  0.1237  11.00000  0.05    0.20
Q2    1   1.5039  0.5121  0.7221  11.00000  0.05    0.18
Q3    1   0.4976  0.7500  0.1570  10.50000  0.05    0.16
Q4    1  -0.6466  0.7500 -0.0784  10.50000  0.05    0.16
Q5    1   0.2873  0.6897  0.1953  11.00000  0.05    0.16
Q6    1   0.5770  0.6108  0.3902  11.00000  0.05    0.15
Q7    1   0.8741  0.7116  0.3824  11.00000  0.05    0.15
Q8    1   0.2822  0.7500  0.0072  10.50000  0.05    0.14
Q9    1   0.1209  0.7500  0.3454  10.50000  0.05    0.14
Q10   1   0.0972  0.5791  0.0604  11.00000  0.05    0.14
Q11   1   0.8208  0.5931  0.2954  11.00000  0.05    0.14
Q12   1   0.2343  0.6792  0.3928  11.00000  0.05    0.14
Q13   1   0.7699  0.7500  0.3211  10.50000  0.05    0.13
Q14   1   1.5408  0.5033  0.9449  11.00000  0.05    0.13
Q15   1   1.2859  0.7500  0.5266  10.50000  0.05    0.13
Q16   1   0.0970  0.7500  0.4232  10.50000  0.05    0.13
Q17   1   0.1780  0.5108  0.3303  11.00000  0.05    0.13
Q18   1  -0.2263  0.6606  0.1768  11.00000  0.05    0.13
Q19   1   0.5408  0.5388  0.5462  11.00000  0.05    0.13
Q20   1   0.7897  0.6439  0.7360  11.00000  0.05    0.13
;
_shelx_res_checksum              68716
####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1897539'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-07-15 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.5-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H5 N2 O S2'
_chemical_formula_sum            'C8 H5 N2 O S2'
_chemical_formula_weight         209.26

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   8.7934(12)
_cell_length_b                   12.8464(14)
_cell_length_c                   16.339(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.394(5)
_cell_angle_gamma                90
_cell_volume                     1809.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    17817
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            'fluorescent yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3675
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.493
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            17327
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.543
_diffrn_reflns_theta_max         27.580
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2081
_reflns_number_gt                1744
_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       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Platon (Spek, 2009)'
_computing_publication_material  'Platon (Spek, 2009)'
_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)+(0.0737P)²+1.3810P] 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         2081
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_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
S1 S 0.63804(7) 0.63712(4) 0.41273(3) 0.0290(2) Uani 1 1 d . . . . .
C1 C 0.6060(3) 0.40626(17) 0.39469(15) 0.0269(5) Uani 1 1 d . . . . .
N1 N 0.5000 0.41007(19) 0.2500 0.0221(5) Uani 1 2 d S T P . .
O2 O 0.6823(2) 1.03527(13) 0.31167(12) 0.0402(5) Uani 1 1 d . . . . .
C2 C 0.5530(2) 0.46476(16) 0.31891(13) 0.0212(4) Uani 1 1 d . . . . .
S2 S 0.71563(7) 0.83370(5) 0.32846(4) 0.0350(2) Uani 1 1 d . . . . .
N2 N 0.5000 0.62828(18) 0.2500 0.0211(5) Uani 1 2 d S T P . .
N3 N 0.6472(3) 0.36069(17) 0.45474(15) 0.0409(6) Uani 1 1 d . . . . .
C3 C 0.5555(2) 0.57440(16) 0.31909(13) 0.0207(4) Uani 1 1 d . . . . .
C5 C 0.5143(3) 0.83414(18) 0.42215(14) 0.0292(5) Uani 1 1 d . . . . .
H5 H 0.4466 0.8120 0.4574 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6068(2) 0.76844(17) 0.38905(13) 0.0237(4) Uani 1 1 d . . . . .
C7 C 0.6336(3) 0.95030(17) 0.34832(14) 0.0287(5) Uani 1 1 d . . . . .
C6 C 0.5292(3) 0.93926(18) 0.39853(15) 0.0316(5) Uani 1 1 d . . . . .
H6 H 0.4726 0.9953 0.4159 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6384(4) 1.13357(19) 0.34237(18) 0.0458(7) Uani 1 1 d . . . . .
H8A H 0.6805 1.1904 0.3135 0.069 Uiso 1 1 calc R U . . .
H8B H 0.6798 1.1384 0.4025 0.069 Uiso 1 1 calc R U . . .
H8C H 0.5250 1.1388 0.3320 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
S1 0.0363(3) 0.0254(3) 0.0217(3) -0.0008(2) -0.0030(2) -0.0004(2)
C1 0.0263(11) 0.0225(11) 0.0320(12) 0.0048(9) 0.0060(9) 0.0024(8)
N1 0.0205(12) 0.0194(12) 0.0275(13) 0.000 0.0074(10) 0.000
O2 0.0545(11) 0.0247(8) 0.0432(10) -0.0022(7) 0.0137(9) -0.0108(8)
C2 0.0187(9) 0.0224(10) 0.0237(11) 0.0024(8) 0.0068(8) 0.0016(8)
S2 0.0360(4) 0.0275(3) 0.0476(4) -0.0062(2) 0.0234(3) -0.0065(2)
N2 0.0204(12) 0.0186(12) 0.0236(12) 0.000 0.0027(10) 0.000
N3 0.0443(13) 0.0403(12) 0.0366(13) 0.0119(9) 0.0041(10) 0.0071(10)
C3 0.0175(9) 0.0210(10) 0.0235(10) -0.0001(8) 0.0038(8) -0.0002(7)
C5 0.0313(12) 0.0323(12) 0.0249(11) -0.0010(9) 0.0077(9) -0.0006(9)
C4 0.0245(10) 0.0239(10) 0.0223(10) -0.0023(8) 0.0037(8) -0.0053(8)
C7 0.0327(12) 0.0250(11) 0.0274(11) -0.0044(9) 0.0031(9) -0.0055(9)
C6 0.0356(12) 0.0277(12) 0.0317(12) -0.0051(9) 0.0073(10) 0.0046(9)
C8 0.073(2) 0.0251(13) 0.0354(14) -0.0007(10) 0.0006(14) -0.0047(12)

_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 C4 1.740(2) . ?
S1 C3 1.754(2) . ?
C1 N3 1.138(3) . ?
C1 C2 1.445(3) . ?
N1 C2 1.331(2) 2_655 ?
N1 C2 1.331(2) . ?
O2 C7 1.354(3) . ?
O2 C8 1.439(3) . ?
C2 C3 1.409(3) . ?
S2 C7 1.721(2) . ?
S2 C4 1.724(2) . ?
N2 C3 1.332(2) 2_655 ?
N2 C3 1.332(2) . ?
C5 C4 1.357(3) . ?
C5 C6 1.418(3) . ?
C5 H5 0.9500 . ?
C7 C6 1.354(4) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C4 S1 C3 103.38(10) . . ?
N3 C1 C2 179.5(3) . . ?
C2 N1 C2 116.3(2) 2_655 . ?
C7 O2 C8 115.0(2) . . ?
N1 C2 C3 122.16(19) . . ?
N1 C2 C1 116.75(19) . . ?
C3 C2 C1 121.08(19) . . ?
C7 S2 C4 90.81(11) . . ?
C3 N2 C3 117.4(2) 2_655 . ?
N2 C3 C2 120.99(19) . . ?
N2 C3 S1 121.30(16) . . ?
C2 C3 S1 117.69(15) . . ?
C4 C5 C6 112.9(2) . . ?
C4 C5 H5 123.6 . . ?
C6 C5 H5 123.6 . . ?
C5 C4 S2 111.77(17) . . ?
C5 C4 S1 126.53(18) . . ?
S2 C4 S1 121.18(13) . . ?
C6 C7 O2 131.6(2) . . ?
C6 C7 S2 112.50(17) . . ?
O2 C7 S2 115.93(18) . . ?
C7 C6 C5 112.0(2) . . ?
C7 C6 H6 124.0 . . ?
C5 C6 H6 124.0 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.087

_shelx_res_file                  
;

    mo_jty171031S4_0m_a.res created by SHELXL-2014/7


TITL mo_jty171031S4_0m_a.res in C2/c
REM Old TITL mo_jty171031S4_0m in C2/c
REM SHELXT solution in C2/c
REM R1 0.128,  Rweak 0.008,  Alpha 0.020,  Orientation as input
REM Formula found by SHELXT:  C8 N3 S2
CELL  0.71073   8.7934  12.8464  16.3386   90.000  101.394   90.000
ZERR    8.000   0.0012   0.0014   0.0021    0.000    0.005    0.000
LATT  7
SYMM -X, Y, 1/2-Z
SFAC C H N O S
UNIT 64 40 16 8 16
ACTA
TEMP -123.140
L.S. 10
BOND $H
LIST 6
FMAP 2
PLAN 20
WGHT    0.073700    1.381000
FVAR       0.39928
S1    5    0.638040    0.637122    0.412727    11.00000    0.03633    0.02541 =
         0.02165   -0.00083   -0.00297   -0.00041
C1    1    0.605971    0.406256    0.394694    11.00000    0.02630    0.02251 =
         0.03199    0.00477    0.00599    0.00239
N1    3    0.500000    0.410068    0.250000    10.50000    0.02048    0.01939 =
         0.02749    0.00000    0.00737    0.00000
O2    4    0.682270    1.035272    0.311668    11.00000    0.05453    0.02472 =
         0.04315   -0.00219    0.01373   -0.01078
C2    1    0.553000    0.464764    0.318911    11.00000    0.01874    0.02236 =
         0.02369    0.00239    0.00683    0.00164
S2    5    0.715634    0.833700    0.328460    11.00000    0.03597    0.02753 =
         0.04759   -0.00616    0.02336   -0.00651
N2    3    0.500000    0.628277    0.250000    10.50000    0.02038    0.01860 =
         0.02363    0.00000    0.00271    0.00000
N3    3    0.647201    0.360688    0.454739    11.00000    0.04427    0.04032 =
         0.03661    0.01195    0.00413    0.00712
C3    1    0.555454    0.574396    0.319094    11.00000    0.01753    0.02099 =
         0.02348   -0.00013    0.00384   -0.00017
C5    1    0.514264    0.834143    0.422151    11.00000    0.03129    0.03231 =
         0.02490   -0.00098    0.00767   -0.00059
AFIX  43
H5    2    0.446610    0.812037    0.457439    11.00000   -1.20000
AFIX   0
C4    1    0.606788    0.768439    0.389052    11.00000    0.02450    0.02395 =
         0.02230   -0.00227    0.00366   -0.00527
C7    1    0.633602    0.950303    0.348316    11.00000    0.03274    0.02496 =
         0.02735   -0.00440    0.00310   -0.00548
C6    1    0.529180    0.939258    0.398529    11.00000    0.03560    0.02770 =
         0.03171   -0.00511    0.00726    0.00461
AFIX  43
H6    2    0.472602    0.995334    0.415875    11.00000   -1.20000
AFIX   0
C8    1    0.638419    1.133567    0.342368    11.00000    0.07271    0.02509 =
         0.03537   -0.00069    0.00065   -0.00466
AFIX 137
H8A   2    0.680515    1.190382    0.313544    11.00000   -1.50000
H8B   2    0.679839    1.138439    0.402498    11.00000   -1.50000
H8C   2    0.525044    1.138813    0.331966    11.00000   -1.50000
AFIX   0
HKLF 4

REM  mo_jty171031S4_0m_a.res in C2/c
REM R1 =  0.0468 for    1744 Fo > 4sig(Fo)  and  0.0592 for all    2081 data
REM    120 parameters refined using      0 restraints

END

WGHT      0.0737      1.3810

REM Highest difference peak  0.355,  deepest hole -0.593,  1-sigma level  0.087
Q1    1   0.5398  0.5221  0.3275  11.00000  0.05    0.36
Q2    1   0.5735  0.9436  0.3727  11.00000  0.05    0.35
Q3    1   0.6554  0.8171  0.3680  11.00000  0.05    0.33
Q4    1   0.5830  1.1414  0.3859  11.00000  0.05    0.28
Q5    1   0.5820  0.4368  0.3563  11.00000  0.05    0.26
Q6    1   0.6265  1.1963  0.4277  11.00000  0.05    0.26
Q7    1   0.5843  0.5955  0.3490  11.00000  0.05    0.26
Q8    1   0.5209  0.6028  0.4299  11.00000  0.05    0.25
Q9    1   0.6497  1.0819  0.3289  11.00000  0.05    0.25
Q10   1   0.6615  0.8986  0.3406  11.00000  0.05    0.25
Q11   1   0.4732  0.4999  0.3529  11.00000  0.05    0.24
Q12   1   0.3654  1.0773  0.2924  11.00000  0.05    0.24
Q13   1   0.5522  0.6887  0.2428  11.00000  0.05    0.24
Q14   1   0.7725  0.8308  0.2598  11.00000  0.05    0.23
Q15   1   0.4782  0.4673  0.3975  11.00000  0.05    0.23
Q16   1   0.5501  0.6201  0.4411  11.00000  0.05    0.23
Q17   1   0.5104  0.8835  0.3959  11.00000  0.05    0.23
Q18   1   0.6959  0.6322  0.3510  11.00000  0.05    0.23
Q19   1   0.7009  1.0800  0.2275  11.00000  0.05    0.22
Q20   1   0.4047  0.6423  0.3793  11.00000  0.05    0.22
;
_shelx_res_checksum              80075
