# 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_dmxztj190104
_database_code_depnum_ccdc_archive 'CCDC 2063120'
loop_
_audit_author_name
_audit_author_address
'Li Jinhui'
;Hebei Agricultural University
China
;
_audit_update_record             
;
2021-02-15 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2019-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H5 N O3 S, C5 H7 N3 O2'
_chemical_formula_sum            'C12 H12 N4 O5 S'
_chemical_formula_weight         324.32
_chemical_melting_point          ?
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.80680(10)
_cell_length_b                   7.9890(2)
_cell_length_c                   25.3855(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.693(2)
_cell_angle_gamma                90
_cell_volume                     1371.04(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6267
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      78.5810
_cell_measurement_theta_min      3.4970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.412
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8455
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.454
_diffrn_reflns_theta_min         3.506
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00 -46.00   0.50    0.50    --    0.00 -37.00 -90.00   52
  2  ω    -29.00  36.00   0.50    0.50    --    0.00 -82.00 150.00  130
  3  ω    -63.00  10.00   0.50    0.50    --    0.00 -57.00-150.00  146
  4  ω     67.00 119.00   0.50    0.50    --  106.20 -82.00 120.00  104
  5  ω    129.00 194.00   0.50    0.50    --  106.20  82.00  30.00  130
  6  ω     39.00  66.00   0.50    0.50    --  106.20 -82.00-180.00   54
  7  ω     77.00 118.00   0.50    0.50    --  106.20  82.00  30.00   82
  8  ω     78.00 141.00   0.50    0.50    --  106.20 -82.00-180.00  126
  9  ω     23.00  49.00   0.50    0.50    --  106.20 -82.00  60.00   52
 10  ω    104.00 130.00   0.50    0.50    --  106.20 -82.00  60.00   52
 11  ω    114.00 185.00   0.50    0.50    --  106.20  30.00-120.00  142
 12  ω     40.00 136.00   0.50    0.50    --  106.20 -61.00  60.00  192
 13  ω     36.00  61.00   0.50    0.50    --  106.20 -82.00 120.00   50
 14  ω    107.00 181.00   0.50    0.50    --  106.20  45.00 -90.00  148
 15  ω     70.00 194.00   0.50    0.50    --  106.20  82.00 -30.00  248
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0190325000
_diffrn_orient_matrix_UB_12      -0.1912409000
_diffrn_orient_matrix_UB_13      -0.0053806000
_diffrn_orient_matrix_UB_21      0.0363257000
_diffrn_orient_matrix_UB_22      -0.0162476000
_diffrn_orient_matrix_UB_23      0.0608184000
_diffrn_orient_matrix_UB_31      -0.2241537000
_diffrn_orient_matrix_UB_32      -0.0189135000
_diffrn_orient_matrix_UB_33      0.0021819000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2744
_reflns_number_total             2910
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2910
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+1.1917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1100
_refine_ls_wR_factor_ref         0.1113
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N4(H4), C6(H6), C1(H1), C10(H10), C9(H9), C11(H11)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.30417(6) 0.33166(5) 0.60162(2) 0.02022(14) Uani 1 1 d . . . . .
O5 O 0.1322(2) 0.23970(17) 0.61195(6) 0.0309(3) Uani 1 1 d . . . . .
O4 O 0.4841(2) 0.23832(17) 0.60392(6) 0.0309(3) Uani 1 1 d . . . . .
O3 O 0.2460(2) 0.70400(18) 0.51327(6) 0.0356(4) Uani 1 1 d . . . . .
O1 O 0.1424(2) 0.56325(19) 0.29727(6) 0.0381(4) Uani 1 1 d . . . . .
N3 N 0.1747(2) 0.17946(18) 0.36846(6) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.0850(2) 0.3138(2) 0.26541(6) 0.0365(4) Uani 1 1 d . . . . .
N1 N 0.2187(2) 0.33025(18) 0.44243(6) 0.0214(3) Uani 1 1 d . . . . .
N2 N 0.1296(2) 0.4106(2) 0.30267(6) 0.0249(3) Uani 1 1 d . . . . .
N4 N 0.2638(3) 0.43648(19) 0.54573(6) 0.0277(4) Uani 1 1 d . . . . .
H4 H 0.240696 0.387297 0.515512 0.033 Uiso 1 1 calc R . . . .
C3 C 0.2056(2) 0.1758(2) 0.42205(7) 0.0188(3) Uani 1 1 d . . . . .
C7 C 0.3091(2) 0.6544(2) 0.60751(7) 0.0192(4) Uani 1 1 d . . . . .
C2 C 0.1682(3) 0.3478(2) 0.35499(7) 0.0202(3) Uani 1 1 d . . . . .
C8 C 0.3323(2) 0.5152(2) 0.64014(7) 0.0184(3) Uani 1 1 d . . . . .
C6 C 0.3259(3) 0.8141(2) 0.62890(8) 0.0229(4) Uani 1 1 d . . . . .
H6 H 0.310076 0.908300 0.607301 0.027 Uiso 1 1 calc R . . . .
C1 C 0.1960(2) 0.4380(2) 0.40081(7) 0.0209(4) Uani 1 1 d . . . . .
H1 H 0.198840 0.554199 0.403174 0.025 Uiso 1 1 calc R . . . .
C12 C 0.2694(3) 0.6090(2) 0.55043(7) 0.0237(4) Uani 1 1 d . . . . .
C10 C 0.3905(3) 0.6877(2) 0.71601(8) 0.0265(4) Uani 1 1 d . . . . .
H10 H 0.418423 0.701140 0.752510 0.032 Uiso 1 1 calc R . . . .
C9 C 0.3730(3) 0.5268(2) 0.69481(7) 0.0227(4) Uani 1 1 d . . . . .
H9 H 0.387847 0.432106 0.716220 0.027 Uiso 1 1 calc R . . . .
C11 C 0.3670(3) 0.8292(2) 0.68360(8) 0.0255(4) Uani 1 1 d . . . . .
H11 H 0.379063 0.935086 0.698851 0.031 Uiso 1 1 calc R . . . .
C4 C 0.1583(3) 0.0309(2) 0.33413(7) 0.0249(4) Uani 1 1 d . . . . .
H4A H 0.217992 -0.063202 0.353318 0.037 Uiso 1 1 calc GR . . . .
H4B H 0.224915 0.051411 0.303442 0.037 Uiso 1 1 calc GR . . . .
H4C H 0.021291 0.007455 0.323188 0.037 Uiso 1 1 calc GR . . . .
C5 C 0.2227(3) 0.0209(2) 0.45437(8) 0.0265(4) Uani 1 1 d . . . . .
H5A H 0.109084 -0.048615 0.444754 0.040 Uiso 1 1 calc GR . . . .
H5B H 0.229738 0.049507 0.491276 0.040 Uiso 1 1 calc GR . . . .
H5C H 0.340196 -0.038551 0.448033 0.040 Uiso 1 1 calc GR . . . .


_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 O5 1.4317(14) . ?
S1 O4 1.4293(14) . ?
S1 N4 1.6428(16) . ?
S1 C8 1.7602(18) . ?
O3 C12 1.207(2) . ?
O1 N2 1.231(2) . ?
N3 C3 1.352(2) . ?
N3 C2 1.387(2) . ?
N3 C4 1.469(2) . ?
O2 N2 1.232(2) . ?
N1 C3 1.337(2) . ?
N1 C1 1.358(2) . ?
N2 C2 1.416(2) . ?
N4 H4 0.8600 . ?
N4 C12 1.383(2) . ?
C3 C5 1.482(2) . ?
C7 C8 1.385(2) . ?
C7 C6 1.386(2) . ?
C7 C12 1.488(2) . ?
C2 C1 1.363(3) . ?
C8 C9 1.386(2) . ?
C6 H6 0.9300 . ?
C6 C11 1.389(3) . ?
C1 H1 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.393(3) . ?
C10 C11 1.396(3) . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

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
O5 S1 N4 111.20(9) . . ?
O5 S1 C8 111.36(8) . . ?
O4 S1 O5 116.09(9) . . ?
O4 S1 N4 110.94(9) . . ?
O4 S1 C8 112.00(8) . . ?
N4 S1 C8 92.95(8) . . ?
C3 N3 C2 105.42(14) . . ?
C3 N3 C4 124.85(14) . . ?
C2 N3 C4 129.71(15) . . ?
C3 N1 C1 106.73(15) . . ?
O1 N2 O2 123.41(16) . . ?
O1 N2 C2 116.61(16) . . ?
O2 N2 C2 119.98(16) . . ?
S1 N4 H4 122.2 . . ?
C12 N4 S1 115.67(13) . . ?
C12 N4 H4 122.2 . . ?
N3 C3 C5 124.62(15) . . ?
N1 C3 N3 111.39(15) . . ?
N1 C3 C5 123.99(16) . . ?
C8 C7 C6 120.43(16) . . ?
C8 C7 C12 112.43(15) . . ?
C6 C7 C12 127.14(17) . . ?
N3 C2 N2 124.92(16) . . ?
C1 C2 N3 107.77(15) . . ?
C1 C2 N2 127.24(16) . . ?
C7 C8 S1 109.84(13) . . ?
C7 C8 C9 122.72(16) . . ?
C9 C8 S1 127.44(14) . . ?
C7 C6 H6 121.0 . . ?
C7 C6 C11 117.99(17) . . ?
C11 C6 H6 121.0 . . ?
N1 C1 C2 108.69(16) . . ?
N1 C1 H1 125.7 . . ?
C2 C1 H1 125.7 . . ?
O3 C12 N4 124.02(18) . . ?
O3 C12 C7 126.88(18) . . ?
N4 C12 C7 109.10(15) . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.36(17) . . ?
C11 C10 H10 119.3 . . ?
C8 C9 C10 116.52(17) . . ?
C8 C9 H9 121.7 . . ?
C10 C9 H9 121.7 . . ?
C6 C11 C10 120.97(17) . . ?
C6 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.536
_oxdiff_exptl_absorpt_empirical_full_min 0.549
