# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mono_a
_database_code_depnum_ccdc_archive 'CCDC 1882434'
_audit_update_record             
;
2018-11-30 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H20 N4 O4 S'
_chemical_formula_sum            'C13 H20 N4 O4 S'
_chemical_formula_weight         328.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.8970(4)
_cell_length_b                   12.6136(9)
_cell_length_c                   21.8512(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.674(4)
_cell_angle_gamma                90
_cell_volume                     1625.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5940
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   0.960
_exptl_transmission_factor_max   0.979
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.222
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   Sheldrick,G.M.,(2003)
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14152
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.864
_diffrn_reflns_theta_max         26.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3363
_reflns_number_gt                2733
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0886P)²+0.2091P] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.051(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3363
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1446
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_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 0.46351(8) 0.27360(3) 0.28513(2) 0.0391(2) Uani 1 1 d . . . . .
O1 O 0.1863(5) 0.06117(18) 0.55176(9) 0.0995(7) Uani 1 1 d . . . . .
O2 O -0.1121(4) 0.1531(2) 0.53370(9) 0.0964(7) Uani 1 1 d . . . . .
O3 O 0.2864(3) 0.25361(11) 0.24078(6) 0.0511(4) Uani 1 1 d . . . . .
O4 O 0.6730(3) 0.21886(12) 0.27659(7) 0.0581(4) Uani 1 1 d . . . . .
N1 N 0.0754(5) 0.12149(17) 0.52046(9) 0.0677(6) Uani 1 1 d . . . . .
N2 N 0.4866(3) 0.39544(12) 0.29842(7) 0.0421(4) Uani 1 1 d . . . . .
N3 N 0.7790(3) 0.45261(12) 0.23219(7) 0.0433(4) Uani 1 1 d . . . . .
N4 N 0.7039(3) 0.54098(13) 0.32064(7) 0.0410(4) Uani 1 1 d . . . . .
C1 C 0.1732(4) 0.15990(15) 0.46273(9) 0.0485(5) Uani 1 1 d . . . . .
C2 C 0.0509(4) 0.23000(17) 0.42807(10) 0.0534(5) Uani 1 1 d . . . . .
H2 H -0.090190 0.253627 0.440862 0.064 Uiso 1 1 calc R U . . .
C3 C 0.1407(4) 0.26511(17) 0.37373(10) 0.0504(5) Uani 1 1 d . . . . .
H3 H 0.059974 0.312647 0.349298 0.060 Uiso 1 1 calc R U . . .
C4 C 0.3506(3) 0.22942(13) 0.35579(9) 0.0381(4) Uani 1 1 d . . . . .
C5 C 0.4698(4) 0.15883(17) 0.39086(11) 0.0546(5) Uani 1 1 d . . . . .
H5 H 0.610627 0.134741 0.378125 0.066 Uiso 1 1 calc R U . . .
C6 C 0.3807(4) 0.12319(19) 0.44537(11) 0.0623(6) Uani 1 1 d . . . . .
H6 H 0.460467 0.075194 0.469728 0.075 Uiso 1 1 calc R U . . .
C7 C 0.6561(3) 0.45978(13) 0.28327(8) 0.0360(4) Uani 1 1 d . . . . .
C8 C 0.7039(5) 0.39218(19) 0.17881(9) 0.0627(6) Uani 1 1 d . . . . .
H8A H 0.787504 0.326985 0.176796 0.094 Uiso 1 1 calc R U . . .
H8B H 0.729782 0.432868 0.142427 0.094 Uiso 1 1 calc R U . . .
H8C H 0.545042 0.376886 0.182058 0.094 Uiso 1 1 calc R U . . .
C9 C 0.9916(4) 0.51012(18) 0.22523(10) 0.0521(5) Uani 1 1 d . . . . .
H9A H 0.961146 0.579030 0.208386 0.078 Uiso 1 1 calc R U . . .
H9B H 1.088926 0.471588 0.198233 0.078 Uiso 1 1 calc R U . . .
H9C H 1.064682 0.517610 0.264477 0.078 Uiso 1 1 calc R U . . .
C10 C 0.6163(3) 0.55912(15) 0.38284(8) 0.0399(4) Uani 1 1 d . . . . .
C11 C 0.6864(4) 0.46764(19) 0.42402(9) 0.0574(6) Uani 1 1 d . . . . .
H11A H 0.607428 0.404567 0.411500 0.086 Uiso 1 1 calc R U . . .
H11B H 0.649185 0.484083 0.465607 0.086 Uiso 1 1 calc R U . . .
H11C H 0.846868 0.456417 0.420999 0.086 Uiso 1 1 calc R U . . .
C12 C 0.3617(4) 0.57591(19) 0.38217(10) 0.0565(6) Uani 1 1 d . . . . .
H12A H 0.322831 0.629250 0.352518 0.085 Uiso 1 1 calc R U . . .
H12B H 0.314020 0.598440 0.421953 0.085 Uiso 1 1 calc R U . . .
H12C H 0.287168 0.510662 0.371597 0.085 Uiso 1 1 calc R U . . .
C13 C 0.7322(4) 0.66028(19) 0.40508(11) 0.0606(6) Uani 1 1 d . . . . .
H13A H 0.893295 0.649470 0.406776 0.091 Uiso 1 1 calc R U . . .
H13B H 0.678695 0.677887 0.445139 0.091 Uiso 1 1 calc R U . . .
H13C H 0.697615 0.717180 0.377327 0.091 Uiso 1 1 calc R U . . .
H4A H 0.760(4) 0.5902(18) 0.3045(10) 0.045(6) 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 O4 1.4295(15) . ?
S1 O3 1.4387(15) . ?
S1 N2 1.5696(15) . ?
S1 C4 1.7782(19) . ?
O1 N1 1.210(3) . ?
O2 N1 1.213(3) . ?
N1 C1 1.475(3) . ?
N2 C7 1.333(2) . ?
N3 C7 1.341(2) . ?
N3 C8 1.458(3) . ?
N3 C9 1.458(3) . ?
N4 C7 1.338(2) . ?
N4 C10 1.478(2) . ?
N4 H4A 0.79(2) . ?
C1 C2 1.365(3) . ?
C1 C6 1.366(3) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(3) . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C12 1.516(3) . ?
C10 C11 1.518(3) . ?
C10 C13 1.524(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
O4 S1 O3 116.68(9) . . ?
O4 S1 N2 115.09(9) . . ?
O3 S1 N2 110.91(9) . . ?
O4 S1 C4 107.17(9) . . ?
O3 S1 C4 104.70(9) . . ?
N2 S1 C4 100.30(8) . . ?
O1 N1 O2 124.1(2) . . ?
O1 N1 C1 118.4(3) . . ?
O2 N1 C1 117.6(2) . . ?
C7 N2 S1 127.88(13) . . ?
C7 N3 C8 122.64(17) . . ?
C7 N3 C9 121.80(16) . . ?
C8 N3 C9 115.47(16) . . ?
C7 N4 C10 127.34(16) . . ?
C7 N4 H4A 114.6(16) . . ?
C10 N4 H4A 116.2(16) . . ?
C2 C1 C6 122.33(19) . . ?
C2 C1 N1 118.5(2) . . ?
C6 C1 N1 119.1(2) . . ?
C1 C2 C3 118.7(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.79(18) . . ?
C5 C4 S1 119.77(15) . . ?
C3 C4 S1 119.42(15) . . ?
C4 C5 C6 119.8(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N2 C7 N4 117.90(15) . . ?
N2 C7 N3 125.45(16) . . ?
N4 C7 N3 116.60(16) . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 C12 111.69(16) . . ?
N4 C10 C11 109.38(15) . . ?
C12 C10 C11 112.02(17) . . ?
N4 C10 C13 105.21(16) . . ?
C12 C10 C13 109.06(17) . . ?
C11 C10 C13 109.23(18) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.105



