# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1897688'
loop_
_audit_author_name
_audit_author_address
'Yu Song'
;OUC
China
;
_audit_update_record             
;
2019-04-03 deposited with the CCDC.	2019-04-15 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            'C9 H15 N5 O5 S2'
_chemical_formula_weight         337.38

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.2350(4)
_cell_length_b                   10.4510(9)
_cell_length_c                   13.2627(11)
_cell_angle_alpha                80.451(3)
_cell_angle_beta                 85.302(3)
_cell_angle_gamma                83.095(3)
_cell_volume                     708.95(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7361
_cell_measurement_theta_min      3.122
_cell_measurement_theta_max      27.462

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.730
_exptl_crystal_size_mid          0.412
_exptl_crystal_size_min          0.146
_exptl_absorpt_coefficient_mu    0.405
_shelx_estimated_absorpt_T_min   0.756
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14674
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.121
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3254
_reflns_number_gt                2607
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0677P)²+0.4578P] 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         3254
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
S1 S 0.39291(12) 0.60235(6) 0.16168(5) 0.0428(2) Uani 1 1 d . . . . .
S2 S 0.21496(11) 0.38629(6) 0.32197(5) 0.03902(19) Uani 1 1 d . . . . .
O1 O 0.2249(4) 0.2485(2) 0.33304(19) 0.0640(6) Uani 1 1 d . . . . .
O2 O -0.0208(3) 0.4679(2) 0.30598(15) 0.0511(5) Uani 1 1 d . . . . .
O3 O 0.4712(4) 0.81946(19) 0.03571(17) 0.0601(6) Uani 1 1 d . . . . .
N1 N 0.7487(4) 0.4389(2) 0.09763(16) 0.0387(5) Uani 1 1 d . . . . .
N2 N 0.6091(4) 0.3663(2) 0.17503(16) 0.0398(5) Uani 1 1 d . . . . .
N3 N 0.7731(4) 0.6523(2) 0.01328(16) 0.0405(5) Uani 1 1 d D . . . .
N4 N 0.3309(5) 0.4235(3) 0.41864(17) 0.0458(5) Uani 1 1 d . . . . .
C1 C 0.6598(4) 0.5626(2) 0.08408(18) 0.0357(5) Uani 1 1 d . . . . .
C2 C 0.4231(5) 0.4391(2) 0.21425(18) 0.0362(5) Uani 1 1 d . . . . .
C3 C 0.6724(5) 0.7806(3) -0.0079(2) 0.0449(6) Uani 1 1 d . . . . .
C4 C 0.8271(7) 0.8639(3) -0.0857(3) 0.0647(9) Uani 1 1 d . . . . .
H4C H 0.776972 0.954117 -0.080559 0.097 Uiso 1 1 calc R U . . .
H4D H 0.797319 0.848562 -0.152988 0.097 Uiso 1 1 calc R U . . .
H4E H 1.006869 0.842740 -0.073933 0.097 Uiso 1 1 calc R U . . .
O4 O 0.2350(3) 0.8904(2) 0.45966(17) 0.0569(6) Uani 1 1 d . . . . .
O5 O 0.3165(4) 0.69292(19) 0.42039(19) 0.0603(6) Uani 1 1 d . . . . .
N5 N -0.2541(4) 0.9198(2) 0.4130(2) 0.0463(6) Uani 1 1 d . . . . .
C5 C 0.1745(4) 0.7942(2) 0.42715(19) 0.0376(5) Uani 1 1 d . . . . .
C6 C -0.0921(4) 0.8027(3) 0.3863(2) 0.0404(6) Uani 1 1 d . . . . .
H6 H -0.174233 0.724308 0.415939 0.049 Uiso 1 1 calc R U . . .
C7 C -0.0861(6) 0.8197(3) 0.2681(2) 0.0563(8) Uani 1 1 d . . . . .
H7A H 0.081619 0.840907 0.237785 0.068 Uiso 1 1 calc R U . . .
H7B H -0.124447 0.740582 0.245838 0.068 Uiso 1 1 calc R U . . .
C8 C -0.2904(6) 0.9301(3) 0.2387(2) 0.0584(8) Uani 1 1 d . . . . .
H8A H -0.251183 0.976281 0.170497 0.070 Uiso 1 1 calc R U . . .
H8B H -0.458329 0.898985 0.240997 0.070 Uiso 1 1 calc R U . . .
C9 C -0.2817(7) 1.0150(3) 0.3175(3) 0.0656(9) Uani 1 1 d . . . . .
H9A H -0.135806 1.065766 0.303303 0.079 Uiso 1 1 calc R U . . .
H9B H -0.439121 1.073780 0.321471 0.079 Uiso 1 1 calc R U . . .
H3 H 0.911(4) 0.630(3) -0.019(2) 0.045(8) Uiso 1 1 d D . . . .
H4A H 0.320(7) 0.508(4) 0.420(3) 0.066(10) Uiso 1 1 d . . . . .
H5A H -0.423(7) 0.892(3) 0.441(3) 0.069(10) Uiso 1 1 d . . . . .
H5B H -0.167(8) 0.954(4) 0.460(3) 0.088(12) Uiso 1 1 d . . . . .
H4B H 0.459(7) 0.370(3) 0.439(3) 0.058(10) Uiso 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
S1 C1 1.718(2) . ?
S1 C2 1.726(3) . ?
S2 O1 1.419(2) . ?
S2 O2 1.4235(19) . ?
S2 N4 1.585(2) . ?
S2 C2 1.778(3) . ?
O3 C3 1.218(3) . ?
N1 C1 1.309(3) . ?
N1 N2 1.384(3) . ?
N2 C2 1.292(3) . ?
N3 C1 1.365(3) . ?
N3 C3 1.373(3) . ?
N3 H3 0.837(17) . ?
N4 H4A 0.89(4) . ?
N4 H4B 0.85(4) . ?
C3 C4 1.488(4) . ?
C4 H4C 0.9600 . ?
C4 H4D 0.9600 . ?
C4 H4E 0.9600 . ?
O4 C5 1.241(3) . ?
O5 C5 1.230(3) . ?
N5 C6 1.479(3) . ?
N5 C9 1.480(4) . ?
N5 H5A 0.99(4) . ?
N5 H5B 0.94(4) . ?
C5 C6 1.526(3) . ?
C6 C7 1.546(4) . ?
C6 H6 0.9800 . ?
C7 C8 1.500(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.486(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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
C1 S1 C2 85.61(12) . . ?
O1 S2 O2 121.31(13) . . ?
O1 S2 N4 108.86(15) . . ?
O2 S2 N4 106.93(14) . . ?
O1 S2 C2 107.81(13) . . ?
O2 S2 C2 104.58(12) . . ?
N4 S2 C2 106.42(12) . . ?
C1 N1 N2 112.13(19) . . ?
C2 N2 N1 111.0(2) . . ?
C1 N3 C3 122.9(2) . . ?
C1 N3 H3 120(2) . . ?
C3 N3 H3 117(2) . . ?
S2 N4 H4A 114(2) . . ?
S2 N4 H4B 112(2) . . ?
H4A N4 H4B 124(3) . . ?
N1 C1 N3 121.8(2) . . ?
N1 C1 S1 115.04(19) . . ?
N3 C1 S1 123.13(18) . . ?
N2 C2 S1 116.16(19) . . ?
N2 C2 S2 125.1(2) . . ?
S1 C2 S2 118.55(14) . . ?
O3 C3 N3 120.6(3) . . ?
O3 C3 C4 124.5(3) . . ?
N3 C3 C4 114.9(2) . . ?
C3 C4 H4C 109.5 . . ?
C3 C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
C3 C4 H4E 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
C6 N5 C9 107.4(2) . . ?
C6 N5 H5A 107(2) . . ?
C9 N5 H5A 111(2) . . ?
C6 N5 H5B 108(2) . . ?
C9 N5 H5B 110(2) . . ?
H5A N5 H5B 113(3) . . ?
O5 C5 O4 125.4(2) . . ?
O5 C5 C6 116.1(2) . . ?
O4 C5 C6 118.4(2) . . ?
N5 C6 C5 110.2(2) . . ?
N5 C6 C7 104.6(2) . . ?
C5 C6 C7 113.3(2) . . ?
N5 C6 H6 109.6 . . ?
C5 C6 H6 109.6 . . ?
C7 C6 H6 109.6 . . ?
C8 C7 C6 104.7(2) . . ?
C8 C7 H7A 110.8 . . ?
C6 C7 H7A 110.8 . . ?
C8 C7 H7B 110.8 . . ?
C6 C7 H7B 110.8 . . ?
H7A C7 H7B 108.9 . . ?
C9 C8 C7 103.2(2) . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
N5 C9 C8 102.8(2) . . ?
N5 C9 H9A 111.2 . . ?
C8 C9 H9A 111.2 . . ?
N5 C9 H9B 111.2 . . ?
C8 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C2 0.6(3) . . . . ?
N2 N1 C1 N3 178.3(2) . . . . ?
N2 N1 C1 S1 -1.6(3) . . . . ?
C3 N3 C1 N1 174.9(2) . . . . ?
C3 N3 C1 S1 -5.2(3) . . . . ?
C2 S1 C1 N1 1.62(19) . . . . ?
C2 S1 C1 N3 -178.3(2) . . . . ?
N1 N2 C2 S1 0.7(3) . . . . ?
N1 N2 C2 S2 -174.76(16) . . . . ?
C1 S1 C2 N2 -1.3(2) . . . . ?
C1 S1 C2 S2 174.46(15) . . . . ?
O1 S2 C2 N2 -20.7(3) . . . . ?
O2 S2 C2 N2 -151.0(2) . . . . ?
N4 S2 C2 N2 96.0(2) . . . . ?
O1 S2 C2 S1 164.00(15) . . . . ?
O2 S2 C2 S1 33.64(17) . . . . ?
N4 S2 C2 S1 -79.34(18) . . . . ?
C1 N3 C3 O3 -1.2(4) . . . . ?
C1 N3 C3 C4 178.7(3) . . . . ?
C9 N5 C6 C5 107.8(3) . . . . ?
C9 N5 C6 C7 -14.3(3) . . . . ?
O5 C5 C6 N5 171.7(2) . . . . ?
O4 C5 C6 N5 -11.6(3) . . . . ?
O5 C5 C6 C7 -71.6(3) . . . . ?
O4 C5 C6 C7 105.1(3) . . . . ?
N5 C6 C7 C8 -11.8(3) . . . . ?
C5 C6 C7 C8 -131.7(3) . . . . ?
C6 C7 C8 C9 33.1(3) . . . . ?
C6 N5 C9 C8 35.1(3) . . . . ?
C7 C8 C9 N5 -41.8(3) . . . . ?

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
N3 H3 N1_$1 0.837(17) 2.102(18) 2.937(3) 176(3) 2_765
N4 H4A O5 0.89(4) 1.93(4) 2.812(3) 177(3) .
N4 H4B O5_$2 0.85(4) 2.25(3) 2.948(3) 139(3) 2_666
N5 H5A O4_$3 0.99(4) 1.79(4) 2.737(3) 160(3) 1_455
N5 H5B O4_$4 0.94(4) 2.07(4) 2.826(3) 137(3) 2_576
C9 H9B O1_$5 0.97 2.39 3.351(4) 169.4 1_465

_refine_diff_density_max         0.686
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.066

