# 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_ab_k1_0001
_database_code_depnum_ccdc_archive 'CCDC 2024098'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2020-08-19 deposited with the CCDC.	2020-10-07 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2018/3

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.1  (Andrew D. Bond, March 2019)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Ziwei Liu'
_cambridge_user_crsid            zliu@mrc-lmb.cam.ac.uk
_cambridge_supervisor_name       'John Sutherland'
_cambridge_supervisor_crsid      johns@mrc-lmb.cam.ac.uk
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             ZL-17-68
_cambridge_data_id               AB_K1_0001
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C H4 N2 S), C N S -, H4 N +'
_chemical_formula_sum            'C5 H20 N10 S5'
_chemical_formula_weight         380.61

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'
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                   10.5332(5)
_cell_length_b                   21.0945(8)
_cell_length_c                   8.1916(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.7245(13)
_cell_angle_gamma                90
_cell_volume                     1813.93(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    7901
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.645
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   'SORTAV (Blessing, 1995)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14100
_diffrn_reflns_av_unetI/netI     0.1075
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.596
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_full        25.006
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3171
_reflns_number_gt                1679
_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.

#===============================================================================
INTENSITY STATISTICS FOR DATASET # 1  sortav.hkl
#===============================================================================
 Resolution   #Data #Theory %Complete Redundancy Mean I Mean I/s Rmerge  Rsigma
#-------------------------------------------------------------------------------
  Inf - 3.51      50     51     98.0     5.04    171.32   30.76  0.0596  0.0220
 3.51 - 2.34     114    114    100.0     5.45    200.75   37.07  0.0240  0.0196
 2.34 - 1.84     166    166    100.0     5.73     71.16   25.89  0.0413  0.0283
 1.84 - 1.60     165    165    100.0     5.64     79.08   23.87  0.0385  0.0292
 1.60 - 1.45     167    167    100.0     5.77     43.00   17.11  0.0591  0.0436
 1.45 - 1.34     168    168    100.0     5.60     38.62   12.81  0.0644  0.0601
 1.34 - 1.26     170    170    100.0     5.67     33.94   12.97  0.0680  0.0616
 1.26 - 1.20     152    152    100.0     5.71     34.63   13.25  0.0711  0.0633
 1.20 - 1.14     197    197    100.0     5.42     22.14    8.06  0.0889  0.1062
 1.14 - 1.10     150    150    100.0     5.60     17.91    7.67  0.1134  0.1267
 1.10 - 1.06     163    163    100.0     5.57     20.81    8.36  0.1141  0.1174
 1.06 - 1.03     152    152    100.0     4.75     12.62    4.63  0.1481  0.2294
 1.03 - 1.00     161    161    100.0     4.06     20.12    5.06  0.1255  0.1742
 1.00 - 0.97     192    192    100.0     3.84     15.92    4.77  0.1362  0.2281
 0.97 - 0.95     132    132    100.0     3.77      8.65    2.57  0.2050  0.4222
 0.95 - 0.92     231    231    100.0     3.07      7.86    1.86  0.2119  0.5659
 0.92 - 0.90     169    169    100.0     2.93      6.23    1.36  0.2399  0.7655
 0.90 - 0.89      95     95    100.0     2.69      5.77    1.13  0.2694  0.9055
 0.89 - 0.87     191    192     99.5     2.37      7.69    1.36  0.2212  0.7485
 0.87 - 0.85     210    214     98.1     1.98      6.69    1.04  0.2437  0.9889
 0.85 - 0.84      92    106     86.8     1.45      7.05    1.05  0.1970  1.0186
#------------------------------------------------------------------------------
 0.94 - 0.84     912    931     98.0     2.42      6.86    1.28  0.2313  0.8229
  Inf - 0.84    3287   3307     99.4     4.36     32.78    9.57  0.0627  0.1077
#===============================================================================
;

_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_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)+(0.0256P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3171
_refine_ls_number_parameters     193
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0645
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   0.812
_refine_ls_restrained_S_all      0.811
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.051

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 0.48546(7) 0.62653(4) -0.00022(7) 0.0353(2) Uani 1 1 d . . . . .
C1 C 0.3398(3) 0.66212(12) -0.0156(3) 0.0333(7) Uani 1 1 d . . . . .
N11 N 0.2802(2) 0.67572(10) -0.1603(2) 0.0454(7) Uani 1 1 d . . . . .
H11A H 0.204510 0.693656 -0.165885 0.054 Uiso 1 1 calc R U . . .
H11B H 0.316284 0.666819 -0.250634 0.054 Uiso 1 1 calc R U . . .
N12 N 0.2814(2) 0.67646(11) 0.1175(2) 0.0468(7) Uani 1 1 d . . . . .
H12A H 0.205751 0.694383 0.107812 0.056 Uiso 1 1 calc R U . . .
H12B H 0.318523 0.668027 0.215312 0.056 Uiso 1 1 calc R U . . .
S2 S 0.24404(7) 0.45375(3) 0.47258(7) 0.0370(2) Uani 1 1 d . . . . .
C2 C 0.1575(2) 0.52249(12) 0.4631(3) 0.0310(7) Uani 1 1 d . . . . .
N21 N 0.1228(2) 0.54970(10) 0.3204(2) 0.0377(6) Uani 1 1 d . . . . .
H21A H 0.077861 0.584919 0.317163 0.045 Uiso 1 1 calc R U . . .
H21B H 0.144632 0.532523 0.228868 0.045 Uiso 1 1 calc R U . . .
N22 N 0.12286(19) 0.54969(10) 0.5976(2) 0.0373(6) Uani 1 1 d . . . . .
H22A H 0.077953 0.584915 0.591054 0.045 Uiso 1 1 calc R U . . .
H22B H 0.144668 0.532610 0.693884 0.045 Uiso 1 1 calc R U . . .
S3 S 0.40474(7) 0.62561(4) 0.49020(7) 0.0353(2) Uani 1 1 d . . . . .
C3 C 0.5413(3) 0.66883(12) 0.5057(3) 0.0304(7) Uani 1 1 d . . . . .
N31 N 0.5975(2) 0.68600(10) 0.6502(2) 0.0387(6) Uani 1 1 d . . . . .
H31A H 0.668915 0.707817 0.655160 0.046 Uiso 1 1 calc R U . . .
H31B H 0.563294 0.675535 0.740880 0.046 Uiso 1 1 calc R U . . .
N32 N 0.5985(2) 0.68634(10) 0.3742(2) 0.0384(6) Uani 1 1 d . . . . .
H32A H 0.669912 0.708149 0.385510 0.046 Uiso 1 1 calc R U . . .
H32B H 0.564995 0.676103 0.275730 0.046 Uiso 1 1 calc R U . . .
S4 S 0.76542(7) 0.99295(3) 0.52812(8) 0.0394(2) Uani 1 1 d . . . . .
C4 C 0.8155(2) 0.91615(13) 0.5332(3) 0.0354(7) Uani 1 1 d . . . . .
N41 N 0.8360(2) 0.88513(10) 0.3960(2) 0.0434(6) Uani 1 1 d . . . . .
H41A H 0.861480 0.845397 0.400828 0.052 Uiso 1 1 calc R U . . .
H41B H 0.824102 0.904397 0.300726 0.052 Uiso 1 1 calc R U . . .
N42 N 0.8349(2) 0.88483(10) 0.6737(2) 0.0397(6) Uani 1 1 d . . . . .
H42A H 0.860407 0.845095 0.673860 0.048 Uiso 1 1 calc R U . . .
H42B H 0.822321 0.903802 0.766698 0.048 Uiso 1 1 calc R U . . .
S5 S 1.07705(8) 0.70447(4) 0.46792(9) 0.0455(2) Uani 1 1 d . . . . .
C5 C 0.9375(3) 0.72840(13) 0.5196(3) 0.0422(8) Uani 1 1 d . . . . .
N5 N 0.8399(3) 0.74619(13) 0.5563(4) 0.0717(9) Uani 1 1 d . . . . .
N6 N 0.5002(2) 0.50011(10) 0.2572(2) 0.0346(6) Uani 1 1 d D . . . .
H1 H 0.4734(17) 0.5306(6) 0.1906(19) 0.052 Uiso 1 1 d D U . . .
H2 H 0.5320(17) 0.4694(7) 0.199(2) 0.052 Uiso 1 1 d D U . . .
H3 H 0.5600(14) 0.5138(8) 0.3284(18) 0.052 Uiso 1 1 d D U . . .
H4 H 0.4358(13) 0.4852(9) 0.307(2) 0.052 Uiso 1 1 d D U . . .


_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 1.704(3) . ?
C1 N11 1.326(3) . ?
C1 N12 1.330(3) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
S2 C2 1.711(3) . ?
C2 N22 1.320(3) . ?
C2 N21 1.327(3) . ?
N21 H21A 0.8800 . ?
N21 H21B 0.8800 . ?
N22 H22A 0.8800 . ?
N22 H22B 0.8800 . ?
S3 C3 1.699(3) . ?
C3 N31 1.329(3) . ?
C3 N32 1.330(3) . ?
N31 H31A 0.8800 . ?
N31 H31B 0.8800 . ?
N32 H32A 0.8800 . ?
N32 H32B 0.8800 . ?
S4 C4 1.703(3) . ?
C4 N42 1.328(3) . ?
C4 N41 1.333(3) . ?
N41 H41A 0.8800 . ?
N41 H41B 0.8800 . ?
N42 H42A 0.8800 . ?
N42 H42B 0.8800 . ?
S5 C5 1.643(4) . ?
C5 N5 1.157(4) . ?
N6 H1 0.875(8) . ?
N6 H2 0.884(8) . ?
N6 H3 0.872(8) . ?
N6 H4 0.878(8) . ?

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
N11 C1 N12 117.8(3) . . ?
N11 C1 S1 121.3(2) . . ?
N12 C1 S1 120.92(19) . . ?
C1 N11 H11A 120.0 . . ?
C1 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C1 N12 H12A 120.0 . . ?
C1 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
N22 C2 N21 118.2(2) . . ?
N22 C2 S2 120.89(19) . . ?
N21 C2 S2 120.91(19) . . ?
C2 N21 H21A 120.0 . . ?
C2 N21 H21B 120.0 . . ?
H21A N21 H21B 120.0 . . ?
C2 N22 H22A 120.0 . . ?
C2 N22 H22B 120.0 . . ?
H22A N22 H22B 120.0 . . ?
N31 C3 N32 116.6(2) . . ?
N31 C3 S3 121.7(2) . . ?
N32 C3 S3 121.73(18) . . ?
C3 N31 H31A 120.0 . . ?
C3 N31 H31B 120.0 . . ?
H31A N31 H31B 120.0 . . ?
C3 N32 H32A 120.0 . . ?
C3 N32 H32B 120.0 . . ?
H32A N32 H32B 120.0 . . ?
N42 C4 N41 117.5(2) . . ?
N42 C4 S4 121.3(2) . . ?
N41 C4 S4 121.17(19) . . ?
C4 N41 H41A 120.0 . . ?
C4 N41 H41B 120.0 . . ?
H41A N41 H41B 120.0 . . ?
C4 N42 H42A 120.0 . . ?
C4 N42 H42B 120.0 . . ?
H42A N42 H42B 120.0 . . ?
N5 C5 S5 178.9(3) . . ?
H1 N6 H2 108.7(12) . . ?
H1 N6 H3 110.6(12) . . ?
H2 N6 H3 108.5(12) . . ?
H1 N6 H4 109.3(12) . . ?
H2 N6 H4 109.2(12) . . ?
H3 N6 H4 110.5(12) . . ?

