# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_UM3255
_database_code_depnum_ccdc_archive 'CCDC 1960382'
loop_
_audit_author_name
_audit_author_address
'Peter Y. Zavalij'
;University of Maryland
United States of America
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;

_audit_creation_method           'SHELXL-2015 & ZCIF'
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 N5 O5 S, 2(H2 O)'
_chemical_formula_sum            'C10 H17 N5 O7 S'
_chemical_formula_weight         351.34

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   23.123(2)
_cell_length_b                   9.7734(9)
_cell_length_c                   6.3397(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.2914(14)
_cell_angle_gamma                90
_cell_volume                     1432.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2458
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      28.4

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    0.275
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'SADABS (Krause et al, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8608
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.762
_diffrn_reflns_theta_max         29.984
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4064
_reflns_number_gt                3438
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_max     0.943
_reflns_Friedel_fraction_full    0.998

_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       'Apex2 (Bruker, 2010)'
_computing_cell_refinement       'Apex2, Saint'
_computing_data_reduction        'Apex2, Saint'
_computing_structure_solution    'ShelXT-2014 (Sheldrick, 2015a)'
_computing_structure_refinement  'ShelXL-2015 (Sheldrick, 2015c)'
_computing_molecular_graphics    'Olex2 (Dolomanov, 2009)'
_computing_publication_material  'Apex2, SHELXL-2015, Platon (Spek, 2015)'
_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)+(0.0044P)²+0.9441P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1397 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4064 # 2200 w/o Fiedel pairs
_refine_ls_number_parameters     242
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0596
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_restrained_S_all      1.187
_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 0.38067(3) 0.84817(8) 0.74245(14) 0.03116(19) Uani 1 1 d . . . . .
C2 C 0.41499(11) 0.6953(3) 0.7396(4) 0.0196(6) Uani 1 1 d . . . . .
N3 N 0.47249(9) 0.6735(2) 0.7509(3) 0.0198(5) Uani 1 1 d . . . . .
H3 H 0.499144 0.737658 0.758160 0.035(10) Uiso 1 1 calc R . . . .
C4 C 0.48308(11) 0.5332(3) 0.7493(4) 0.0162(5) Uani 1 1 d . . . . .
C5 C 0.53605(11) 0.4600(3) 0.7578(4) 0.0173(5) Uani 1 1 d . . . . .
O6 O 0.58545(7) 0.5061(2) 0.7682(3) 0.0219(4) Uani 1 1 d . . . . .
N7 N 0.52533(9) 0.3189(2) 0.7538(3) 0.0171(5) Uani 1 1 d . . . . .
H7 H 0.555544 0.264138 0.756933 0.037(10) Uiso 1 1 calc R . . . .
C8 C 0.47172(11) 0.2590(3) 0.7454(4) 0.0178(6) Uani 1 1 d . . . . .
N9 N 0.47043(12) 0.1227(3) 0.7437(4) 0.0255(6) Uani 1 1 d . . . . .
H9A H 0.4342(16) 0.070(4) 0.738(6) 0.042(7) Uiso 1 1 d . . . . .
H9B H 0.5006(16) 0.079(4) 0.755(6) 0.042(7) Uiso 1 1 d . . . . .
N10 N 0.42221(8) 0.3305(2) 0.7367(3) 0.0158(5) Uani 1 1 d . . . . .
C11 C 0.43134(11) 0.4677(3) 0.7373(4) 0.0156(5) Uani 1 1 d . . . . .
N12 N 0.38918(9) 0.5682(2) 0.7267(3) 0.0155(5) Uani 1 1 d . . . . .
C13 C 0.32682(10) 0.5504(3) 0.7091(4) 0.0158(5) Uani 1 1 d . . . . .
H13 H 0.307841 0.642144 0.698763 0.008(6) Uiso 1 1 calc R . . . .
C14 C 0.30483(10) 0.4599(3) 0.5266(4) 0.0168(5) Uani 1 1 d . . . . .
H14 H 0.329751 0.377106 0.510082 0.008(6) Uiso 1 1 calc R . . . .
O15 O 0.29872(8) 0.5321(2) 0.3358(3) 0.0254(5) Uani 1 1 d . . . . .
H15 H 0.327377 0.516503 0.260328 0.042(10) Uiso 1 1 calc R . . . .
C16 C 0.24551(11) 0.4218(3) 0.6096(4) 0.0184(6) Uani 1 1 d . . . . .
H16 H 0.229966 0.336231 0.543144 0.019(7) Uiso 1 1 calc R . . . .
O17 O 0.20717(7) 0.5363(2) 0.5774(3) 0.0213(4) Uani 1 1 d . . . . .
H17 H 0.207425 0.559984 0.450050 0.040(10) Uiso 1 1 calc R . . . .
C18 C 0.25684(10) 0.4049(3) 0.8470(4) 0.0176(5) Uani 1 1 d . . . . .
H18 H 0.223735 0.445098 0.924672 0.024(8) Uiso 1 1 calc R . . . .
C19 C 0.26750(11) 0.2618(3) 0.9250(5) 0.0225(6) Uani 1 1 d . . . . .
H19A H 0.277001 0.264957 1.077920 0.018(5) Uiso 1 1 calc R . . . .
H19B H 0.231536 0.207805 0.905688 0.018(5) Uiso 1 1 calc R . . . .
O20 O 0.31372(8) 0.1934(2) 0.8180(3) 0.0227(4) Uani 1 1 d . . . . .
H20 H 0.341189 0.248346 0.801403 0.022(8) Uiso 1 1 calc R . . . .
O21 O 0.30900(7) 0.48385(19) 0.8957(3) 0.0171(4) Uani 1 1 d . . . . .
O1W O 0.55374(10) 0.8782(2) 0.7371(4) 0.0374(6) Uani 1 1 d . . . . .
H11W H 0.5756(19) 0.869(5) 0.647(7) 0.086(12) Uiso 1 1 d . . . . .
H12W H 0.574(2) 0.890(5) 0.860(7) 0.086(12) Uiso 1 1 d . . . . .
O2W O 0.11696(9) 0.6331(2) 0.8108(4) 0.0305(5) Uani 1 1 d . . . . .
H21W H 0.135(2) 0.632(4) 0.923(6) 0.089(12) Uiso 1 1 d D . . . .
H22W H 0.137(2) 0.606(5) 0.711(7) 0.089(12) 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 C2 1.692(3) . ?
C2 N3 1.347(3) . ?
C2 N12 1.379(3) . ?
N3 C4 1.393(4) . ?
N3 H3 0.8800 . ?
C4 C11 1.357(4) . ?
C4 C5 1.418(3) . ?
C5 O6 1.228(3) . ?
C5 N7 1.401(4) . ?
N7 C8 1.371(3) . ?
N7 H7 0.8800 . ?
C8 N9 1.333(3) . ?
C8 N10 1.341(3) . ?
N9 H9A 0.98(4) . ?
N9 H9B 0.82(4) . ?
N10 C11 1.357(3) . ?
C11 N12 1.385(3) . ?
N12 C13 1.454(3) . ?
C13 O21 1.419(3) . ?
C13 C14 1.534(4) . ?
C13 H13 1.0000 . ?
C14 O15 1.405(3) . ?
C14 C16 1.526(3) . ?
C14 H14 1.0000 . ?
O15 H15 0.8400 . ?
C16 O17 1.439(3) . ?
C16 C18 1.530(4) . ?
C16 H16 1.0000 . ?
O17 H17 0.8400 . ?
C18 O21 1.459(3) . ?
C18 C19 1.502(4) . ?
C18 H18 1.0000 . ?
C19 O20 1.443(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
O20 H20 0.8400 . ?
O1W H11W 0.78(4) . ?
O1W H12W 0.91(4) . ?
O2W H21W 0.82(4) . ?
O2W H22W 0.83(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
N3 C2 N12 106.6(2) . . ?
N3 C2 S1 127.0(2) . . ?
N12 C2 S1 126.39(19) . . ?
C2 N3 C4 109.2(2) . . ?
C2 N3 H3 125.4 . . ?
C4 N3 H3 125.4 . . ?
C11 C4 N3 108.0(2) . . ?
C11 C4 C5 121.6(2) . . ?
N3 C4 C5 130.4(2) . . ?
O6 C5 N7 121.7(2) . . ?
O6 C5 C4 128.2(3) . . ?
N7 C5 C4 110.1(2) . . ?
C8 N7 C5 125.5(2) . . ?
C8 N7 H7 117.3 . . ?
C5 N7 H7 117.3 . . ?
N9 C8 N10 120.1(3) . . ?
N9 C8 N7 116.6(2) . . ?
N10 C8 N7 123.3(2) . . ?
C8 N9 H9A 123(2) . . ?
C8 N9 H9B 120(2) . . ?
H9A N9 H9B 117(3) . . ?
C8 N10 C11 112.5(2) . . ?
N10 C11 C4 127.1(2) . . ?
N10 C11 N12 126.3(2) . . ?
C4 C11 N12 106.7(2) . . ?
C2 N12 C11 109.4(2) . . ?
C2 N12 C13 122.6(2) . . ?
C11 N12 C13 127.9(2) . . ?
O21 C13 N12 107.27(19) . . ?
O21 C13 C14 105.50(19) . . ?
N12 C13 C14 116.0(2) . . ?
O21 C13 H13 109.3 . . ?
N12 C13 H13 109.3 . . ?
C14 C13 H13 109.3 . . ?
O15 C14 C16 110.22(19) . . ?
O15 C14 C13 112.6(2) . . ?
C16 C14 C13 99.52(19) . . ?
O15 C14 H14 111.3 . . ?
C16 C14 H14 111.3 . . ?
C13 C14 H14 111.3 . . ?
C14 O15 H15 109.5 . . ?
O17 C16 C14 108.5(2) . . ?
O17 C16 C18 108.4(2) . . ?
C14 C16 C18 103.3(2) . . ?
O17 C16 H16 112.1 . . ?
C14 C16 H16 112.1 . . ?
C18 C16 H16 112.1 . . ?
C16 O17 H17 109.5 . . ?
O21 C18 C19 107.1(2) . . ?
O21 C18 C16 105.9(2) . . ?
C19 C18 C16 116.6(2) . . ?
O21 C18 H18 109.0 . . ?
C19 C18 H18 109.0 . . ?
C16 C18 H18 109.0 . . ?
O20 C19 C18 113.2(2) . . ?
O20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
O20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C19 O20 H20 109.5 . . ?
C13 O21 C18 108.65(18) . . ?
H11W O1W H12W 108(4) . . ?
H21W O2W H22W 112(4) . . ?

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
N12 C2 N3 C4 -1.1(3) . . . . ?
S1 C2 N3 C4 178.4(2) . . . . ?
C2 N3 C4 C11 -0.1(3) . . . . ?
C2 N3 C4 C5 179.8(3) . . . . ?
C11 C4 C5 O6 179.8(3) . . . . ?
N3 C4 C5 O6 -0.1(5) . . . . ?
C11 C4 C5 N7 -0.6(4) . . . . ?
N3 C4 C5 N7 179.5(2) . . . . ?
O6 C5 N7 C8 179.0(2) . . . . ?
C4 C5 N7 C8 -0.7(4) . . . . ?
C5 N7 C8 N9 -179.7(3) . . . . ?
C5 N7 C8 N10 1.1(4) . . . . ?
N9 C8 N10 C11 -179.3(3) . . . . ?
N7 C8 N10 C11 -0.1(4) . . . . ?
C8 N10 C11 C4 -1.3(4) . . . . ?
C8 N10 C11 N12 179.1(2) . . . . ?
N3 C4 C11 N10 -178.4(2) . . . . ?
C5 C4 C11 N10 1.7(4) . . . . ?
N3 C4 C11 N12 1.3(3) . . . . ?
C5 C4 C11 N12 -178.6(2) . . . . ?
N3 C2 N12 C11 2.0(3) . . . . ?
S1 C2 N12 C11 -177.6(2) . . . . ?
N3 C2 N12 C13 -179.1(2) . . . . ?
S1 C2 N12 C13 1.3(4) . . . . ?
N10 C11 N12 C2 177.7(2) . . . . ?
C4 C11 N12 C2 -2.0(3) . . . . ?
N10 C11 N12 C13 -1.2(4) . . . . ?
C4 C11 N12 C13 179.1(2) . . . . ?
C2 N12 C13 O21 -114.7(2) . . . . ?
C11 N12 C13 O21 64.0(3) . . . . ?
C2 N12 C13 C14 127.7(3) . . . . ?
C11 N12 C13 C14 -53.6(3) . . . . ?
O21 C13 C14 O15 157.15(18) . . . . ?
N12 C13 C14 O15 -84.3(3) . . . . ?
O21 C13 C14 C16 40.4(2) . . . . ?
N12 C13 C14 C16 159.0(2) . . . . ?
O15 C14 C16 O17 -40.9(3) . . . . ?
C13 C14 C16 O17 77.6(2) . . . . ?
O15 C14 C16 C18 -155.8(2) . . . . ?
C13 C14 C16 C18 -37.3(2) . . . . ?
O17 C16 C18 O21 -92.3(2) . . . . ?
C14 C16 C18 O21 22.7(3) . . . . ?
O17 C16 C18 C19 148.7(2) . . . . ?
C14 C16 C18 C19 -96.3(3) . . . . ?
O21 C18 C19 O20 -63.7(3) . . . . ?
C16 C18 C19 O20 54.6(3) . . . . ?
N12 C13 O21 C18 -151.9(2) . . . . ?
C14 C13 O21 C18 -27.7(2) . . . . ?
C19 C18 O21 C13 128.1(2) . . . . ?
C16 C18 O21 C13 3.0(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
_geom_hbond_publ_flag
N3 H3 O1W 0.88 1.87 2.747(3) 173 . yes
N7 H7 O2W 0.88 1.94 2.808(3) 170 3_545 yes
N9 H9A S1 0.98(4) 2.50(4) 3.392(3) 151(3) 1_545 yes
N9 H9B O1W 0.82(4) 2.32(4) 3.071(3) 153(3) 1_545 yes
O15 H15 O6 0.84 2.03 2.784(2) 149 2_656 yes
O15 H15 O21 0.84 2.36 2.844(3) 117 1_554 yes
O17 H17 O20 0.84 2.19 2.970(3) 155 4_556 yes
O20 H20 N10 0.84 2.09 2.901(3) 163 . yes
O1W H11W S1 0.78(4) 2.70(5) 3.440(3) 161(4) 2_656 yes
O1W H12W S1 0.91(4) 2.74(4) 3.612(3) 162(4) 2_657 yes
O2W H21W O20 0.82(4) 2.09(3) 2.878(3) 162(4) 4_557 yes
O2W H22W O17 0.83(5) 1.97(5) 2.752(3) 156(5) . yes

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.052


_diffrn_radiation_monochromator  graphite
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.0424143
_diffrn_orient_matrix_UB_12      -0.0198939
_diffrn_orient_matrix_UB_13      -0.0011236
_diffrn_orient_matrix_UB_21      0.0081831
_diffrn_orient_matrix_UB_22      0.0996055
_diffrn_orient_matrix_UB_23      -0.0196350
_diffrn_orient_matrix_UB_31      0.0023135
_diffrn_orient_matrix_UB_32      0.0123322
_diffrn_orient_matrix_UB_33      0.1565447
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_detector                 'CCD area detector'
