# 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_js220j
_database_code_depnum_ccdc_archive 'CCDC 2024028'
loop_
_audit_author_name
_audit_author_address
'Lu Hu'
;University of Idaho
United States of America
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-02-18
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
staples@chemistry.msu.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H6 O S, C5 H4 N8 O4, 0.5(H2 O)'
_chemical_formula_sum            'C7 H11 N8 O5.50 S'
_chemical_formula_weight         327.30
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9526(2)
_cell_length_b                   11.2186(3)
_cell_length_c                   17.4355(5)
_cell_angle_alpha                88.790(2)
_cell_angle_beta                 85.798(2)
_cell_angle_gamma                79.513(2)
_cell_volume                     1333.59(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    173(1
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.768
_shelx_estimated_absorpt_T_min   0.529
_exptl_absorpt_coefficient_mu    2.598
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0610 before and 0.0484 after correction.
The Ratio of minimum to maximum transmission is 0.8518.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chunk
_exptl_crystal_F_000             676
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.0420
0.00 -1.00 0.00 0.0870
1.00 1.00 0.00 0.0880
-1.00 -1.00 0.00 0.1110
1.00 1.00 1.00 0.1020
-1.00 -1.00 -1.00 0.1070
0.00 0.00 -1.00 0.0130
0.00 0.00 1.00 0.0530

_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.107
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structure was solved 
by the direct method using the SHELXT program and refined by least squares 
method on F2, SHELXL, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21093
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.278
_diffrn_reflns_theta_min         2.541
_diffrn_ambient_temperature      173(1
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4388
_reflns_number_total             4781
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution    
'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         4781
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+0.7197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          
;
The structure was refined by Least Squares using version 2014/6 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom on the non-carbon atom(s) which was found 
by difference Fourier methods and refined isotropically.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4A), C4A(H4AB)
2.b Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,H2SC), C3S(H3SA,H3SB,H3SC), C4S(H4SA,H4SB,
 H4SC)
;
_atom_sites_solution_hydrogens   mixed
_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 0.31495(7) 0.67994(5) 0.88616(3) 0.03840(14) Uani 1 1 d . . . . .
O1S O 0.1078(2) 0.66986(16) 0.91460(9) 0.0507(4) Uani 1 1 d . . . . .
C1S C 0.3331(5) 0.8314(3) 0.9033(2) 0.0886(12) Uani 1 1 d . . . . .
H1SA H 0.228530 0.885876 0.878617 0.133 Uiso 1 1 calc R U . . .
H1SB H 0.460891 0.846698 0.882024 0.133 Uiso 1 1 calc R U . . .
H1SC H 0.320109 0.846039 0.958819 0.133 Uiso 1 1 calc R U . . .
C2S C 0.3164(4) 0.6878(4) 0.78606(15) 0.0850(12) Uani 1 1 d . . . . .
H2SA H 0.292410 0.611018 0.766358 0.128 Uiso 1 1 calc R U . . .
H2SB H 0.444231 0.702659 0.764609 0.128 Uiso 1 1 calc R U . . .
H2SC H 0.213352 0.754042 0.770991 0.128 Uiso 1 1 calc R U . . .
S2 S 0.11300(7) 0.25395(4) 0.91141(3) 0.03006(13) Uani 1 1 d . . . . .
O2S O 0.21640(19) 0.21379(13) 0.83333(7) 0.0323(3) Uani 1 1 d . . . . .
C3S C 0.2567(4) 0.3509(2) 0.94954(14) 0.0558(7) Uani 1 1 d . . . . .
H3SA H 0.394988 0.311716 0.945418 0.084 Uiso 1 1 calc R U . . .
H3SB H 0.213696 0.367045 1.003709 0.084 Uiso 1 1 calc R U . . .
H3SC H 0.240709 0.427427 0.920556 0.084 Uiso 1 1 calc R U . . .
C4S C 0.1701(3) 0.12751(18) 0.97336(12) 0.0385(5) Uani 1 1 d . . . . .
H4SA H 0.103657 0.062655 0.958237 0.058 Uiso 1 1 calc R U . . .
H4SB H 0.126021 0.151353 1.026423 0.058 Uiso 1 1 calc R U . . .
H4SC H 0.312146 0.098488 0.969738 0.058 Uiso 1 1 calc R U . . .
O1 O 0.7006(2) 0.45401(12) 0.90841(7) 0.0366(3) Uani 1 1 d . . . . .
O2 O 0.6839(2) 0.32332(13) 0.81983(8) 0.0397(3) Uani 1 1 d . . . . .
O3 O 0.6356(2) 0.59333(11) 0.45528(7) 0.0326(3) Uani 1 1 d . . . . .
O4 O 0.7676(2) 0.47780(12) 0.36033(7) 0.0342(3) Uani 1 1 d . . . . .
N1 N 0.7205(2) 0.54729(13) 0.66984(8) 0.0236(3) Uani 1 1 d . . . . .
N2 N 0.7259(2) 0.53079(13) 0.59291(8) 0.0225(3) Uani 1 1 d . . . . .
H2 H 0.666(3) 0.591(2) 0.5690(13) 0.034(6) Uiso 1 1 d . . . . .
N3 N 1.0138(2) 0.22441(12) 0.57725(8) 0.0215(3) Uani 1 1 d . . . . .
N4 N 1.0247(2) 0.24890(13) 0.70375(9) 0.0232(3) Uani 1 1 d . . . . .
H4 H 1.073(3) 0.236(2) 0.7472(14) 0.038(6) Uiso 1 1 d . . . . .
N5 N 0.8158(2) 0.48658(14) 0.79007(8) 0.0271(3) Uani 1 1 d . . . . .
H5 H 0.804(3) 0.563(2) 0.8051(14) 0.040(6) Uiso 1 1 d . . . . .
N6 N 0.7255(2) 0.41708(13) 0.84265(9) 0.0272(3) Uani 1 1 d . . . . .
N7 N 0.8283(2) 0.41054(12) 0.47650(8) 0.0224(3) Uani 1 1 d . . . . .
N8 N 0.7395(2) 0.49816(13) 0.42967(8) 0.0233(3) Uani 1 1 d . . . . .
C1 C 0.8125(2) 0.46049(15) 0.71180(10) 0.0230(3) Uani 1 1 d . . . . .
C2 C 0.8128(2) 0.43075(15) 0.55270(10) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.9079(2) 0.33586(15) 0.59928(9) 0.0202(3) Uani 1 1 d . . . . .
C4 C 1.0810(2) 0.17622(15) 0.64212(10) 0.0231(3) Uani 1 1 d . . . . .
H4A H 1.160957 0.098235 0.645155 0.028 Uiso 1 1 calc R U . . .
C5 C 0.9125(2) 0.35154(15) 0.67718(10) 0.0219(3) Uani 1 1 d . . . . .
O1A O 0.5156(2) 0.22737(11) 0.45154(7) 0.0326(3) Uani 1 1 d . . . . .
O2A O 0.6588(2) 0.11573(12) 0.35615(7) 0.0331(3) Uani 1 1 d . . . . .
O3A O 0.6608(2) 0.07723(13) 0.90748(7) 0.0375(3) Uani 1 1 d . . . . .
O4A O 0.89140(19) 0.03810(13) 0.81533(8) 0.0344(3) Uani 1 1 d . . . . .
N1A N 0.5731(2) 0.15330(13) 0.59047(8) 0.0210(3) Uani 1 1 d . . . . .
H1A H 0.514(3) 0.215(2) 0.5666(13) 0.031(6) Uiso 1 1 d . . . . .
N2A N 0.5464(2) 0.16110(13) 0.66851(8) 0.0225(3) Uani 1 1 d . . . . .
N3A N 0.8423(2) -0.14158(13) 0.70341(8) 0.0232(3) Uani 1 1 d . . . . .
N4A N 0.8875(2) -0.14324(12) 0.57503(8) 0.0208(3) Uani 1 1 d . . . . .
H4AA H 0.923(3) -0.170(2) 0.5293(14) 0.032(6) Uiso 1 1 d . . . . .
N5A N 0.7155(2) 0.04726(12) 0.47216(8) 0.0216(3) Uani 1 1 d . . . . .
N6A N 0.6259(2) 0.13473(13) 0.42553(8) 0.0227(3) Uani 1 1 d . . . . .
N7A N 0.5771(2) 0.07707(14) 0.78841(8) 0.0248(3) Uani 1 1 d . . . . .
H7A H 0.474(3) 0.124(2) 0.8039(13) 0.033(6) Uiso 1 1 d . . . . .
N8A N 0.7199(2) 0.06388(13) 0.83974(8) 0.0264(3) Uani 1 1 d . . . . .
C1A C 0.6835(2) 0.06194(14) 0.54887(9) 0.0195(3) Uani 1 1 d . . . . .
C2A C 0.6305(2) 0.06991(15) 0.70934(10) 0.0208(3) Uani 1 1 d . . . . .
C3A C 0.7495(2) -0.03371(15) 0.67417(9) 0.0203(3) Uani 1 1 d . . . . .
C4A C 0.9230(3) -0.20347(15) 0.64163(10) 0.0236(3) Uani 1 1 d . . . . .
H4AB H 0.998626 -0.282830 0.644110 0.028 Uiso 1 1 calc R U . . .
C5A C 0.7756(2) -0.03387(14) 0.59488(9) 0.0191(3) Uani 1 1 d . . . . .
O1W O 0.7900(2) 0.71769(12) 0.83512(8) 0.0302(3) Uani 1 1 d . . . . .
H1WA H 0.804(4) 0.766(2) 0.8000(15) 0.039(6) Uiso 1 1 d . . . . .
H1WB H 0.897(4) 0.711(2) 0.8604(16) 0.050(7) 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 O1S 1.5118(17) . ?
S1 C1S 1.760(3) . ?
S1 C2S 1.745(3) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
S2 O2S 1.5290(13) . ?
S2 C3S 1.773(3) . ?
S2 C4S 1.7689(19) . ?
C3S H3SA 0.9800 . ?
C3S H3SB 0.9800 . ?
C3S H3SC 0.9800 . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 0.9800 . ?
O1 N6 1.217(2) . ?
O2 N6 1.222(2) . ?
O3 N8 1.2463(19) . ?
O4 N8 1.2300(19) . ?
N1 N2 1.355(2) . ?
N1 C1 1.306(2) . ?
N2 H2 0.84(2) . ?
N2 C2 1.357(2) . ?
N3 C3 1.377(2) . ?
N3 C4 1.323(2) . ?
N4 H4 0.85(3) . ?
N4 C4 1.353(2) . ?
N4 C5 1.361(2) . ?
N5 H5 0.89(3) . ?
N5 N6 1.380(2) . ?
N5 C1 1.404(2) . ?
N7 N8 1.354(2) . ?
N7 C2 1.346(2) . ?
C1 C5 1.415(2) . ?
C2 C3 1.420(2) . ?
C3 C5 1.377(2) . ?
C4 H4A 0.9500 . ?
O1A N6A 1.2461(19) . ?
O2A N6A 1.2302(19) . ?
O3A N8A 1.225(2) . ?
O4A N8A 1.221(2) . ?
N1A H1A 0.86(2) . ?
N1A N2A 1.362(2) . ?
N1A C1A 1.352(2) . ?
N2A C2A 1.307(2) . ?
N3A C3A 1.370(2) . ?
N3A C4A 1.326(2) . ?
N4A H4AA 0.86(2) . ?
N4A C4A 1.347(2) . ?
N4A C5A 1.364(2) . ?
N5A N6A 1.353(2) . ?
N5A C1A 1.348(2) . ?
N7A H7A 0.84(2) . ?
N7A N8A 1.371(2) . ?
N7A C2A 1.401(2) . ?
C1A C5A 1.413(2) . ?
C2A C3A 1.421(2) . ?
C3A C5A 1.381(2) . ?
C4A H4AB 0.9500 . ?
O1W H1WA 0.82(3) . ?
O1W H1WB 0.88(3) . ?

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
O1S S1 C1S 104.89(13) . . ?
O1S S1 C2S 105.92(12) . . ?
C2S S1 C1S 98.3(2) . . ?
S1 C1S H1SA 109.5 . . ?
S1 C1S H1SB 109.5 . . ?
S1 C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
S1 C2S H2SA 109.5 . . ?
S1 C2S H2SB 109.5 . . ?
S1 C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
O2S S2 C3S 105.37(10) . . ?
O2S S2 C4S 105.36(9) . . ?
C4S S2 C3S 99.25(12) . . ?
S2 C3S H3SA 109.5 . . ?
S2 C3S H3SB 109.5 . . ?
S2 C3S H3SC 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 109.5 . . ?
S2 C4S H4SA 109.5 . . ?
S2 C4S H4SB 109.5 . . ?
S2 C4S H4SC 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?
C1 N1 N2 118.40(14) . . ?
N1 N2 H2 113.7(15) . . ?
N1 N2 C2 127.40(15) . . ?
C2 N2 H2 118.9(15) . . ?
C4 N3 C3 103.63(14) . . ?
C4 N4 H4 123.5(16) . . ?
C4 N4 C5 106.35(14) . . ?
C5 N4 H4 129.0(16) . . ?
N6 N5 H5 112.5(16) . . ?
N6 N5 C1 117.46(15) . . ?
C1 N5 H5 120.0(16) . . ?
O1 N6 O2 126.20(16) . . ?
O1 N6 N5 116.11(15) . . ?
O2 N6 N5 117.66(15) . . ?
C2 N7 N8 118.52(14) . . ?
O3 N8 N7 122.05(14) . . ?
O4 N8 O3 122.16(14) . . ?
O4 N8 N7 115.79(14) . . ?
N1 C1 N5 115.86(15) . . ?
N1 C1 C5 120.24(15) . . ?
N5 C1 C5 123.76(15) . . ?
N2 C2 C3 113.60(15) . . ?
N7 C2 N2 130.05(15) . . ?
N7 C2 C3 116.30(14) . . ?
N3 C3 C2 128.80(15) . . ?
C5 C3 N3 110.59(14) . . ?
C5 C3 C2 120.50(15) . . ?
N3 C4 N4 113.40(15) . . ?
N3 C4 H4A 123.3 . . ?
N4 C4 H4A 123.3 . . ?
N4 C5 C1 134.20(16) . . ?
N4 C5 C3 106.02(15) . . ?
C3 C5 C1 119.77(15) . . ?
N2A N1A H1A 113.9(15) . . ?
C1A N1A H1A 118.7(15) . . ?
C1A N1A N2A 127.31(14) . . ?
C2A N2A N1A 117.97(14) . . ?
C4A N3A C3A 103.94(14) . . ?
C4A N4A H4AA 127.1(15) . . ?
C4A N4A C5A 105.88(14) . . ?
C5A N4A H4AA 126.9(15) . . ?
C1A N5A N6A 118.44(13) . . ?
O1A N6A N5A 121.89(14) . . ?
O2A N6A O1A 122.58(14) . . ?
O2A N6A N5A 115.52(14) . . ?
N8A N7A H7A 113.2(16) . . ?
N8A N7A C2A 119.65(14) . . ?
C2A N7A H7A 119.1(16) . . ?
O3A N8A N7A 115.49(15) . . ?
O4A N8A O3A 125.77(15) . . ?
O4A N8A N7A 118.72(14) . . ?
N1A C1A C5A 113.15(15) . . ?
N5A C1A N1A 130.72(15) . . ?
N5A C1A C5A 116.11(14) . . ?
N2A C2A N7A 114.90(14) . . ?
N2A C2A C3A 121.56(15) . . ?
N7A C2A C3A 123.19(15) . . ?
N3A C3A C2A 132.47(15) . . ?
N3A C3A C5A 110.06(14) . . ?
C5A C3A C2A 117.40(15) . . ?
N3A C4A N4A 113.67(15) . . ?
N3A C4A H4AB 123.2 . . ?
N4A C4A H4AB 123.2 . . ?
N4A C5A C1A 130.82(15) . . ?
N4A C5A C3A 106.45(14) . . ?
C3A C5A C1A 122.54(15) . . ?
H1WA O1W H1WB 105(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
_geom_hbond_publ_flag
N2 H2 O3 0.84(2) 2.01(2) 2.5758(19) 124(2) . yes
N2 H2 O1A 0.84(2) 2.23(2) 3.0374(19) 160(2) 2_666 yes
N4 H4 O2S 0.85(3) 1.85(3) 2.6923(19) 170(2) 1_655 yes
N5 H5 O1W 0.89(3) 1.81(3) 2.696(2) 178(2) . yes
N1A H1A O3 0.86(2) 2.25(2) 3.0650(19) 160(2) 2_666 yes
N1A H1A O1A 0.86(2) 2.01(2) 2.5795(19) 123.2(19) . yes
N4A H4AA N3 0.86(2) 1.96(2) 2.821(2) 176(2) 2_756 yes
N7A H7A O2S 0.84(2) 1.93(2) 2.760(2) 172(2) . yes
O1W H1WA N3A 0.82(3) 1.99(3) 2.799(2) 170(2) 1_565 yes
O1W H1WB O1S 0.88(3) 1.79(3) 2.660(2) 170(3) 1_655 yes

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
N1 N2 C2 N7 -177.66(16) . . . . ?
N1 N2 C2 C3 -0.6(2) . . . . ?
N1 C1 C5 N4 177.20(18) . . . . ?
N1 C1 C5 C3 -1.8(3) . . . . ?
N2 N1 C1 N5 174.82(14) . . . . ?
N2 N1 C1 C5 -0.9(2) . . . . ?
N2 C2 C3 N3 -178.05(16) . . . . ?
N2 C2 C3 C5 -2.3(2) . . . . ?
N3 C3 C5 N4 0.69(19) . . . . ?
N3 C3 C5 C1 179.96(15) . . . . ?
N5 C1 C5 N4 1.8(3) . . . . ?
N5 C1 C5 C3 -177.23(16) . . . . ?
N6 N5 C1 N1 117.52(17) . . . . ?
N6 N5 C1 C5 -66.9(2) . . . . ?
N7 C2 C3 N3 -0.5(3) . . . . ?
N7 C2 C3 C5 175.20(15) . . . . ?
N8 N7 C2 N2 -3.2(3) . . . . ?
N8 N7 C2 C3 179.75(14) . . . . ?
C1 N1 N2 C2 2.2(3) . . . . ?
C1 N5 N6 O1 -167.83(15) . . . . ?
C1 N5 N6 O2 14.3(2) . . . . ?
C2 N7 N8 O3 -4.1(2) . . . . ?
C2 N7 N8 O4 176.06(14) . . . . ?
C2 C3 C5 N4 -175.76(15) . . . . ?
C2 C3 C5 C1 3.5(2) . . . . ?
C3 N3 C4 N4 0.24(19) . . . . ?
C4 N3 C3 C2 175.50(17) . . . . ?
C4 N3 C3 C5 -0.57(18) . . . . ?
C4 N4 C5 C1 -179.63(19) . . . . ?
C4 N4 C5 C3 -0.52(18) . . . . ?
C5 N4 C4 N3 0.2(2) . . . . ?
N1A N2A C2A N7A -172.27(14) . . . . ?
N1A N2A C2A C3A 1.2(2) . . . . ?
N1A C1A C5A N4A 175.74(16) . . . . ?
N1A C1A C5A C3A 1.5(2) . . . . ?
N2A N1A C1A N5A 179.30(16) . . . . ?
N2A N1A C1A C5A 0.8(2) . . . . ?
N2A C2A C3A N3A -175.67(17) . . . . ?
N2A C2A C3A C5A 0.9(2) . . . . ?
N3A C3A C5A N4A -0.46(19) . . . . ?
N3A C3A C5A C1A 174.97(15) . . . . ?
N5A C1A C5A N4A -3.0(3) . . . . ?
N5A C1A C5A C3A -177.23(15) . . . . ?
N6A N5A C1A N1A -0.4(3) . . . . ?
N6A N5A C1A C5A 178.06(14) . . . . ?
N7A C2A C3A N3A -2.8(3) . . . . ?
N7A C2A C3A C5A 173.80(15) . . . . ?
N8A N7A C2A N2A -127.69(17) . . . . ?
N8A N7A C2A C3A 59.0(2) . . . . ?
C1A N1A N2A C2A -2.1(2) . . . . ?
C1A N5A N6A O1A -0.1(2) . . . . ?
C1A N5A N6A O2A -179.20(14) . . . . ?
C2A N7A N8A O3A 176.59(15) . . . . ?
C2A N7A N8A O4A -4.8(2) . . . . ?
C2A C3A C5A N4A -177.76(14) . . . . ?
C2A C3A C5A C1A -2.3(2) . . . . ?
C3A N3A C4A N4A -0.35(19) . . . . ?
C4A N3A C3A C2A 177.25(18) . . . . ?
C4A N3A C3A C5A 0.49(18) . . . . ?
C4A N4A C5A C1A -174.67(17) . . . . ?
C4A N4A C5A C3A 0.23(18) . . . . ?
C5A N4A C4A N3A 0.1(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id LU-020
_olex2_submission_special_instructions 'No special instructions were received'
