# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_exp_158
_database_code_depnum_ccdc_archive 'CCDC 2107262'
loop_
_audit_author_name
_audit_author_address
'Takumi Abe'
;Okayama University
Japan
;
_audit_update_record             
;
2021-09-03 deposited with the CCDC.	2021-11-16 downloaded from the CCDC.
;
_audit_creation_date             2021-07-19
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 N4 O3 S'
_chemical_formula_sum            'C16 H16 N4 O3 S'
_chemical_formula_weight         344.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   18.10420(10)
_cell_length_b                   8.55940(10)
_cell_length_c                   21.00970(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3255.69(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    39280
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      68.1890
_cell_measurement_theta_min      2.4350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.971
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.533
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -6 0 0.4437
1 6 -1 0.4325
1 0 14 0.0506
-1 -6 0 0.4422
-12 0 3 0.1319
9 0 9 0.0768
3 0 13 0.0356
-5 0 12 0.0658
-7 0 -11 0.0788
-1 0 -14 0.0581
7 0 -11 0.1168

_exptl_crystal_size_max          0.907
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.111
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.3029 -5.5204 0.2860 0.0218 -0.0008 0.9998
1.2760 5.5170 -0.6343 0.0038 0.0028 -1.0000
0.9993 -0.0737 13.5879 -0.9959 -0.0780 0.0460
-0.6677 -5.5443 0.4104 0.0039 0.0512 0.9987
-11.5301 -0.0574 2.6343 -0.0262 -0.9921 0.1224
8.6176 -0.0531 9.2714 -0.7924 0.6088 -0.0397
3.4440 0.0004 13.0395 -0.9913 0.1310 0.0090
-4.9997 -0.0628 12.3421 -0.8206 -0.5636 0.0944
-6.8126 -0.2953 -11.0888 0.8995 -0.4294 0.0801
-1.0305 -0.0515 -13.5853 0.9967 0.0779 -0.0233
7.0888 0.0326 -10.8781 0.6852 0.7210 -0.1033

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            61402
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.499
_diffrn_reflns_theta_min         4.209
_diffrn_ambient_temperature      103.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     73.00 108.00   0.50    0.20    --   40.40  77.00 120.00   70
  2  ω     15.00  69.00   0.50    0.20    --   40.40  77.00 -90.00  108
  3  ω     14.00  49.00   0.50    0.20    --   40.40  77.00 -30.00   70
  4  ω     83.00 109.00   0.50    0.20    --   40.40  77.00 -90.00   52
  5  ω     76.00 108.00   0.50    0.20    --   40.40  77.00-120.00   64
  6  ω     68.00  96.00   0.50    0.20    --   40.40  77.00-180.00   56
  7  ω     14.00  61.00   0.50    0.20    --   40.40  77.00-180.00   94
  8  ω     15.00  49.00   0.50    0.20    --   40.40  77.00-120.00   68
  9  ω     21.00  65.00   0.50    0.20    --   40.40  63.00 -90.00   88
 10  ω     84.00 109.00   0.50    0.20    --   40.40  63.00 -90.00   50
 11  ω     66.00 106.00   0.50    0.20    --   40.40  37.00-120.00   80
 12  ω     60.00 109.00   0.50    0.20    --   40.40  77.00 -30.00   98
 13  ω     21.00  95.00   0.50    0.20    --   40.40  50.00  90.00  148
 14  ω     14.00  70.00   0.50    0.20    --   40.40  77.00 120.00  112
 15  ω     18.00  84.00   0.50    0.20    --   40.40  63.00  30.00  132
 16  ω     25.00  57.00   0.50    0.20    --   40.40  37.00-120.00   64
 17  ω    -12.00  42.00   0.50    0.20    --   40.40 -37.00-120.00  108
 18  ω    -19.00   6.00   0.50    0.20    --   40.40 -50.00 -30.00   50
 19  ω     11.00  53.00   0.50    0.20    --   40.40 -50.00 -30.00   84
 20  ω    117.00 160.00   0.50    0.20    --   96.04 140.00-140.00   86
 21  ω     92.00 117.00   0.50    0.20    --   96.04 129.00  46.00   50
 22  ω     38.00  64.00   0.50    0.20    --   96.04 -59.00 120.00   52
 23  ω     43.00  96.00   0.50    0.20    --   96.04 -77.00 120.00  106
 24  ω     28.00  69.00   0.50    0.20    --   96.04 -59.00 -30.00   82
 25  ω     27.00 106.00   0.50    0.20    --   96.04 -77.00-120.00  158
 26  ω     28.00  72.00   0.50    0.20    --   96.04 -77.00-180.00   88
 27  ω     34.00  82.00   0.50    0.20    --   96.04 -68.00 -60.00   96
 28  ω     -3.00  34.00   0.50    0.20    --   40.40-104.00  60.00   74
 29  ω     22.00  78.00   0.50    0.20    --   40.40-129.00 -27.00  112
 30  ω     42.00  68.00   0.50    0.20    --   40.40-104.00  60.00   52
 31  ω     30.00  95.00   0.50    0.20    --   40.40-140.00 159.00  130
 32  ω     83.00 115.00   0.50    0.20    --   96.04-140.00 159.00   64
 33  ω     88.00 113.00   0.50    0.20    --   96.04-129.00 -27.00   50
 34  ω    -54.00  26.00   0.50    0.20    --  -40.71  50.00  60.00  160
 35  ω    -40.00  26.00   0.50    0.20    --  -40.71  37.00 150.00  132
 36  ω    -33.00  -7.00   0.50    0.20    --  -40.71  37.00 -60.00   52
 37  ω     -4.00  25.00   0.50    0.20    --  -40.71  37.00 -60.00   58
 38  ω    -56.00  26.00   0.50    0.20    --  -40.71  50.00 -90.00  164
 39  ω    -42.00  23.00   0.50    0.20    --  -40.71  37.00-150.00  130
 40  ω    -21.00  19.00   0.50    0.20    --  -40.71  12.00 -90.00   80
 41  ω    -31.00  30.00   0.50    0.20    --  -40.71  25.00  30.00  122
 42  ω      8.00  33.00   0.50    0.20    --   40.40  94.00 124.09   50
 43  ω     11.00  36.00   0.50    0.20    --   40.40  86.00  82.34   50
 44  ω     10.00  35.00   0.50    0.20    --   40.40  87.00 124.50   50
 45  ω     11.00  36.00   0.50    0.20    --   40.40  85.00  34.26   50
 46  ω      8.00  33.00   0.50    0.20    --   40.40  92.00 -19.54   50
 47  ω     11.00  36.00   0.50    0.20    --   40.40  84.00 -64.37   50
 48  ω     11.00  38.00   0.50    0.20    --   40.40  86.00-173.14   54
 49  ω     68.00 119.00   0.50    0.20    --   96.04  80.00 -77.79  102
 50  ω     69.00  96.00   0.50    0.20    --   96.04  79.00 -39.65   54
 51  ω     69.00  94.00   0.50    0.20    --   96.04  77.00 120.00   50
 52  ω     69.00  95.00   0.50    0.20    --   96.04  77.00  90.00   52
 53  ω     69.00  94.00   0.50    0.20    --   96.04  77.00  60.00   50
 54  ω    132.00 165.00   0.50    0.20    --   96.04  77.00  30.00   66
 55  ω    140.00 165.00   0.50    0.20    --   96.04  77.00 -30.00   50
 56  ω    135.00 161.00   0.50    0.20    --   96.04  77.00 -60.00   52
 57  ω     69.00  95.00   0.50    0.20    --   96.04  77.00  30.00   52
 58  ω     69.00  94.00   0.50    0.20    --   96.04  77.00 -30.00   50
 59  ω     70.00 103.00   0.50    0.20    --   96.04  73.00 -50.32   66
 60  ω     69.00  94.00   0.50    0.20    --   96.04  77.00 -60.00   50
 61  ω     72.00 145.00   0.50    0.20    --   96.04  68.00 -90.00  146
 62  ω     69.00  94.00   0.50    0.20    --   96.04  77.00-150.00   50
 63  ω    -66.00 -41.00   0.50    0.20    --  -40.71 140.00-140.00   50
 64  ω    -65.00 -39.00   0.50    0.20    --  -40.71 129.00  46.00   52
 65  ω    -45.00 -20.00   0.50    0.20    --  -40.71 104.00 150.00   50
 66  ω    -78.00 -53.00   0.50    0.20    --  -40.71 104.00 150.00   50
 67  ω   -126.00 -74.00   0.50    0.20    --  -96.35 144.00  60.00  104
 68  ω   -126.00 -41.00   0.50    0.20    --  -96.35 144.00 150.00  170
 69  ω    -97.00 -72.00   0.50    0.20    --  -96.35 129.00  46.00   50
 70  ω    -77.00 -38.00   0.50    0.20    --  -96.35 138.00 -35.96   78
 71  ω   -122.00 -82.00   0.50    0.20    --  -96.35 138.00 -35.96   80
 72  ω    -82.00 -54.00   0.50    0.20    --  -96.35 140.00-140.00   56
 73  ω   -102.00 -46.00   0.50    0.20    --  -96.35  96.00-120.00  112
 74  ω   -110.00 -69.00   0.50    0.20    --  -96.35 115.00 -37.69   82
 75  ω    -94.00 -29.00   0.50    0.20    --  -96.35  77.00  90.00  130
 76  ω    -67.00 -41.00   0.50    0.20    --  -96.35  59.00  90.00   52
 77  ω    -69.00 -37.00   0.50    0.20    --  -96.35  59.00-150.00   64
 78  ω    -57.00 -13.00   0.50    0.20    --  -40.71 -79.00-143.63   88
 79  ω    -64.00 -20.00   0.50    0.20    --  -40.71 -77.00 -90.00   88
 80  ω   -106.00 -79.00   0.50    0.20    --  -40.71 -77.00 -90.00   54
 81  ω   -109.00 -64.00   0.50    0.20    --  -40.71 -63.00   0.00   90
 82  ω   -108.00 -57.00   0.50    0.20    --  -40.71 -77.00  90.00  102
 83  ω   -107.00 -81.00   0.50    0.20    --  -40.71 -63.00 120.00   52
 84  ω    -52.00 -23.00   0.50    0.20    --  -40.71 -63.00 120.00   58
 85  ω    -59.00 -25.00   0.50    0.20    --  -40.71 -37.00 150.00   68
 86  ω   -106.00 -79.00   0.50    0.20    --  -40.71 -37.00 150.00   54
 87  ω    -43.00 -18.00   0.50    0.20    --  -40.71 -63.00   0.00   50
 88  ω    -50.00 -25.00   0.50    0.20    --  -40.71 -37.00 -40.02   50
 89  ω    -73.00 -27.00   0.50    0.20    --  -40.71 -37.00 -90.00   92
 90  ω   -101.00 -76.00   0.50    0.20    --  -40.71 -37.00 -40.02   50
 91  ω    -52.00 -27.00   0.50    0.20    --  -40.71 -37.00  60.00   50
 92  ω   -126.00 -98.00   0.50    0.20    --  -96.35-129.00 -27.00   56
 93  ω   -137.00-112.00   0.50    0.20    --  -96.35-140.00 159.00   50
 94  ω   -133.00 -69.00   0.50    0.20    --  -96.35 -79.00 176.32  128
 95  ω   -143.00 -68.00   0.50    0.20    --  -96.35 -80.00 141.64  150
 96  ω   -164.00 -68.00   0.50    0.20    --  -96.35 -80.00 -18.22  192
 97  ω   -164.00 -68.00   0.50    0.20    --  -96.35 -80.00 -97.90  192
 98  ω   -143.00 -69.00   0.50    0.20    --  -96.35 -79.00-128.15  148
 99  ω    -94.00 -69.00   0.50    0.20    --  -96.35 -79.00-105.17   50
100  ω   -164.00 -69.00   0.50    0.20    --  -96.35 -78.00 -73.66  190
101  ω   -164.00-108.00   0.50    0.20    --  -96.35 -77.00 -60.00  112
102  ω   -135.00-103.00   0.50    0.20    --  -96.35 -77.00-120.00   64
103  ω   -163.00-138.00   0.50    0.20    --  -96.35 -77.00-120.00   50
104  ω    -98.00 -69.00   0.50    0.20    --  -96.35 -78.00  -9.61   58
105  ω    -94.00 -69.00   0.50    0.20    --  -96.35 -77.00 -90.00   50
106  ω   -163.00 -69.00   0.50    0.20    --  -96.35 -77.00  60.00  188
107  ω   -165.00 -69.00   0.50    0.20    --  -96.35 -79.00 130.04  192
108  ω    -96.00 -69.00   0.50    0.20    --  -96.35 -77.00 150.00   54
109  ω    -94.00 -69.00   0.50    0.20    --  -96.35 -77.00 120.00   50
110  ω   -163.00 -69.00   0.50    0.20    --  -96.35 -79.00 162.96  188
111  ω   -150.00-123.00   0.50    0.20    --  -96.35 -77.00 120.00   54
112  ω   -163.00 -69.00   0.50    0.20    --  -96.35 -77.00   0.00  188
113  ω    -94.00 -69.00   0.50    0.20    --  -96.35 -77.00  94.92   50
114  ω    -94.00 -69.00   0.50    0.20    --  -96.35 -77.00  30.00   50
115  ω   -145.00-119.00   0.50    0.20    --  -96.35 -77.00  94.92   52
116  ω   -148.00-123.00   0.50    0.20    --  -96.35 -77.00 -90.00   50
117  ω   -100.00 -69.00   0.50    0.20    --  -96.35 -77.00-180.00   62
118  ω   -155.00 -69.00   0.50    0.20    --  -96.35 -77.00-150.00  172
119  ω   -159.00-133.00   0.50    0.20    --  -96.35 -77.00-180.00   52
120  ω   -158.00 -70.00   0.50    0.20    --  -96.35 -76.00-138.60  176
121  ω    -98.00 -69.00   0.50    0.20    --  -96.35 -77.00-120.00   58
122  ω    -94.00 -69.00   0.50    0.20    --  -96.35 -77.00 -60.00   50
123  ω   -155.00 -72.00   0.50    0.20    --  -96.35 -68.00  30.00  166
124  ω   -133.00 -70.00   0.50    0.20    --  -96.35 -76.00   8.62  126
125  ω    -97.00 -71.00   0.50    0.20    --  -96.35 -72.00  78.65   52
126  ω   -137.00 -71.00   0.50    0.20    --  -96.35 -70.00  68.05  132
127  ω   -164.00 -75.00   0.50    0.20    --  -96.35 -59.00  90.00  178
128  ω   -118.00 -70.00   0.50    0.20    --  -96.35 -74.00  20.15   96
129  ω   -162.00-108.00   0.50    0.20    --  -96.35 -67.00-173.23  108
130  ω   -101.00 -72.00   0.50    0.20    --  -96.35 -68.00-180.00   58
131  ω    -97.00 -72.00   0.50    0.20    --  -96.35 -67.00-173.23   50
132  ω    -37.00 -12.00   0.50    0.20    --  -40.71 -82.00-170.06   50
133  ω    -35.00 -10.00   0.50    0.20    --  -40.71 -89.00  -9.71   50
134  ω    -34.00  -9.00   0.50    0.20    --  -40.71 -89.00  14.95   50
135  ω    -38.00 -13.00   0.50    0.20    --  -40.71 -86.00 -53.49   50
136  ω    -33.00  -8.00   0.50    0.20    --  -40.71 -93.00  83.88   50
137  ω    -34.00  -9.00   0.50    0.20    --  -40.71 -89.00  86.43   50
138  ω    -33.00  -8.00   0.50    0.20    --  -40.71 -92.00 156.38   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0142194000
_diffrn_orient_matrix_UB_12      -0.0043383000
_diffrn_orient_matrix_UB_13      -0.0722704000
_diffrn_orient_matrix_UB_21      0.0834099000
_diffrn_orient_matrix_UB_22      -0.0201678000
_diffrn_orient_matrix_UB_23      -0.0119824000
_diffrn_orient_matrix_UB_31      -0.0090263000
_diffrn_orient_matrix_UB_32      -0.1788133000
_diffrn_orient_matrix_UB_33      0.0030808000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2887
_reflns_number_total             2986
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00060(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2986
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+1.6235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0780
_refine_special_details          ?
_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 Ternary CH refined with riding coordinates:
 C3(H3), C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C19(H19), C8(H8), C7(H7), C22(H22), C6(H6), C20(H20), C5(H5)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_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
S10 S 0.37962(2) 0.50891(3) 0.41332(2) 0.01730(11) Uani 1 1 d . . . . .
O12 O 0.44807(5) 0.56268(11) 0.43936(4) 0.0223(2) Uani 1 1 d . . . . .
O11 O 0.33091(5) 0.61732(10) 0.38247(4) 0.0225(2) Uani 1 1 d . . . . .
O13 O 0.38095(5) 0.36995(12) 0.24750(4) 0.0262(2) Uani 1 1 d . . . . .
N1 N 0.39947(6) 0.37621(12) 0.35903(5) 0.0182(2) Uani 1 1 d . . . . .
N15 N 0.32149(6) 0.08024(15) 0.25151(6) 0.0315(3) Uani 1 1 d . . . . .
N16 N 0.37939(7) 0.05352(16) 0.22135(6) 0.0329(3) Uani 1 1 d . . . . .
C9 C 0.43576(7) 0.23410(15) 0.37729(6) 0.0177(3) Uani 1 1 d . . . . .
C18 C 0.33199(7) 0.41096(14) 0.47442(6) 0.0186(3) Uani 1 1 d . . . . .
C4 C 0.39963(7) 0.10689(15) 0.35059(6) 0.0206(3) Uani 1 1 d . . . . .
C23 C 0.25623(7) 0.38641(15) 0.46917(6) 0.0222(3) Uani 1 1 d . . . . .
H23 H 0.229897 0.423338 0.433065 0.027 Uiso 1 1 calc R U . . .
C3 C 0.33407(7) 0.16228(16) 0.31245(6) 0.0230(3) Uani 1 1 d . . . . .
H3 H 0.289005 0.147356 0.339299 0.028 Uiso 1 1 calc R U . . .
C19 C 0.37116(7) 0.35527(15) 0.52677(6) 0.0216(3) Uani 1 1 d . . . . .
H19 H 0.422915 0.371810 0.529965 0.026 Uiso 1 1 calc R U . . .
C8 C 0.49747(7) 0.21614(16) 0.41567(6) 0.0209(3) Uani 1 1 d . . . . .
H8 H 0.522288 0.303637 0.433464 0.025 Uiso 1 1 calc R U . . .
C7 C 0.52147(8) 0.06384(17) 0.42696(6) 0.0243(3) Uani 1 1 d . . . . .
H7 H 0.563367 0.047355 0.453340 0.029 Uiso 1 1 calc R U . . .
C22 C 0.21984(7) 0.30742(16) 0.51731(6) 0.0245(3) Uani 1 1 d . . . . .
H22 H 0.168127 0.290495 0.513959 0.029 Uiso 1 1 calc R U . . .
C21 C 0.25745(7) 0.25218(15) 0.57062(6) 0.0230(3) Uani 1 1 d . . . . .
C2 C 0.34736(7) 0.34035(16) 0.30594(6) 0.0201(3) Uani 1 1 d . . . . .
H2 H 0.300215 0.400206 0.310459 0.024 Uiso 1 1 calc R U . . .
C6 C 0.48577(8) -0.06416(17) 0.40071(7) 0.0274(3) Uani 1 1 d . . . . .
H6 H 0.503388 -0.166578 0.409247 0.033 Uiso 1 1 calc R U . . .
C20 C 0.33363(7) 0.27549(16) 0.57408(6) 0.0241(3) Uani 1 1 d . . . . .
H20 H 0.360229 0.235869 0.609555 0.029 Uiso 1 1 calc R U . . .
N17 N 0.42728(8) 0.0196(2) 0.18962(7) 0.0460(4) Uani 1 1 d . . . . .
C5 C 0.42424(8) -0.04332(16) 0.36189(7) 0.0259(3) Uani 1 1 d . . . . .
H5 H 0.399701 -0.130523 0.343578 0.031 Uiso 1 1 calc R U . . .
C14 C 0.39031(9) 0.53361(19) 0.23556(7) 0.0353(4) Uani 1 1 d . . . . .
H14A H 0.410884 0.548609 0.192848 0.053 Uiso 1 1 calc R U . . .
H14B H 0.424108 0.577923 0.267209 0.053 Uiso 1 1 calc R U . . .
H14C H 0.342348 0.586195 0.238452 0.053 Uiso 1 1 calc R U . . .
C24 C 0.21742(8) 0.17045(18) 0.62384(7) 0.0322(3) Uani 1 1 d . . . . .
H24A H 0.164067 0.185251 0.618732 0.048 Uiso 1 1 calc R U . . .
H24B H 0.233173 0.214260 0.664735 0.048 Uiso 1 1 calc R U . . .
H24C H 0.228936 0.058613 0.622691 0.048 Uiso 1 1 calc R 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
S10 O12 1.4307(9) . ?
S10 O11 1.4349(9) . ?
S10 N1 1.6493(11) . ?
S10 C18 1.7591(13) . ?
O13 C2 1.3933(15) . ?
O13 C14 1.4331(19) . ?
N1 C9 1.4347(16) . ?
N1 C2 1.4928(15) . ?
N15 N16 1.2462(17) . ?
N15 C3 1.4779(17) . ?
N16 N17 1.1315(18) . ?
C9 C4 1.3886(18) . ?
C9 C8 1.3863(18) . ?
C18 C23 1.3920(18) . ?
C18 C19 1.3928(18) . ?
C4 C3 1.5085(18) . ?
C4 C5 1.381(2) . ?
C23 H23 0.9500 . ?
C23 C22 1.3835(19) . ?
C3 H3 1.0000 . ?
C3 C2 1.5492(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.3841(19) . ?
C8 H8 0.9500 . ?
C8 C7 1.3944(19) . ?
C7 H7 0.9500 . ?
C7 C6 1.386(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.3934(19) . ?
C21 C20 1.3954(19) . ?
C21 C24 1.5049(18) . ?
C2 H2 1.0000 . ?
C6 H6 0.9500 . ?
C6 C5 1.392(2) . ?
C20 H20 0.9500 . ?
C5 H5 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
O12 S10 O11 119.80(6) . . ?
O12 S10 N1 107.29(5) . . ?
O12 S10 C18 107.40(6) . . ?
O11 S10 N1 105.48(5) . . ?
O11 S10 C18 109.67(6) . . ?
N1 S10 C18 106.46(6) . . ?
C2 O13 C14 112.56(10) . . ?
C9 N1 S10 119.91(8) . . ?
C9 N1 C2 108.35(10) . . ?
C2 N1 S10 121.38(8) . . ?
N16 N15 C3 113.46(11) . . ?
N17 N16 N15 172.43(14) . . ?
C4 C9 N1 109.94(10) . . ?
C8 C9 N1 128.21(12) . . ?
C8 C9 C4 121.85(12) . . ?
C23 C18 S10 119.81(10) . . ?
C23 C18 C19 120.84(12) . . ?
C19 C18 S10 119.32(10) . . ?
C9 C4 C3 109.81(11) . . ?
C5 C4 C9 120.56(12) . . ?
C5 C4 C3 129.61(12) . . ?
C18 C23 H23 120.5 . . ?
C22 C23 C18 119.01(12) . . ?
C22 C23 H23 120.5 . . ?
N15 C3 C4 115.60(11) . . ?
N15 C3 H3 107.6 . . ?
N15 C3 C2 114.51(11) . . ?
C4 C3 H3 107.6 . . ?
C4 C3 C2 103.52(10) . . ?
C2 C3 H3 107.6 . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 119.07(12) . . ?
C20 C19 H19 120.5 . . ?
C9 C8 H8 121.5 . . ?
C9 C8 C7 116.98(12) . . ?
C7 C8 H8 121.5 . . ?
C8 C7 H7 119.1 . . ?
C6 C7 C8 121.72(13) . . ?
C6 C7 H7 119.1 . . ?
C23 C22 H22 119.3 . . ?
C23 C22 C21 121.39(12) . . ?
C21 C22 H22 119.3 . . ?
C22 C21 C20 118.44(12) . . ?
C22 C21 C24 121.30(12) . . ?
C20 C21 C24 120.26(13) . . ?
O13 C2 N1 110.19(10) . . ?
O13 C2 C3 108.94(10) . . ?
O13 C2 H2 111.3 . . ?
N1 C2 C3 103.56(10) . . ?
N1 C2 H2 111.3 . . ?
C3 C2 H2 111.3 . . ?
C7 C6 H6 119.8 . . ?
C7 C6 C5 120.32(13) . . ?
C5 C6 H6 119.8 . . ?
C19 C20 C21 121.22(13) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C4 C5 C6 118.56(13) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
S10 N1 C9 C4 132.14(10) . . . . ?
S10 N1 C9 C8 -47.65(16) . . . . ?
S10 N1 C2 O13 119.91(10) . . . . ?
S10 N1 C2 C3 -123.70(10) . . . . ?
S10 C18 C23 C22 179.19(10) . . . . ?
S10 C18 C19 C20 -178.69(10) . . . . ?
O12 S10 N1 C9 63.10(10) . . . . ?
O12 S10 N1 C2 -155.96(9) . . . . ?
O12 S10 C18 C23 161.19(10) . . . . ?
O12 S10 C18 C19 -20.50(12) . . . . ?
O11 S10 N1 C9 -168.12(9) . . . . ?
O11 S10 N1 C2 -27.19(11) . . . . ?
O11 S10 C18 C23 29.51(12) . . . . ?
O11 S10 C18 C19 -152.19(10) . . . . ?
N1 S10 C18 C23 -84.14(11) . . . . ?
N1 S10 C18 C19 94.17(11) . . . . ?
N1 C9 C4 C3 -0.85(14) . . . . ?
N1 C9 C4 C5 -179.48(11) . . . . ?
N1 C9 C8 C7 179.12(12) . . . . ?
N15 C3 C2 O13 -30.13(15) . . . . ?
N15 C3 C2 N1 -147.40(10) . . . . ?
N16 N15 C3 C4 -41.30(18) . . . . ?
N16 N15 C3 C2 78.93(16) . . . . ?
C9 N1 C2 O13 -95.23(12) . . . . ?
C9 N1 C2 C3 21.16(12) . . . . ?
C9 C4 C3 N15 139.87(12) . . . . ?
C9 C4 C3 C2 13.83(13) . . . . ?
C9 C4 C5 C6 0.19(19) . . . . ?
C9 C8 C7 C6 0.50(19) . . . . ?
C18 S10 N1 C9 -51.64(10) . . . . ?
C18 S10 N1 C2 89.30(10) . . . . ?
C18 C23 C22 C21 -0.07(19) . . . . ?
C18 C19 C20 C21 -1.0(2) . . . . ?
C4 C9 C8 C7 -0.66(18) . . . . ?
C4 C3 C2 O13 96.61(11) . . . . ?
C4 C3 C2 N1 -20.66(12) . . . . ?
C23 C18 C19 C20 -0.40(19) . . . . ?
C23 C22 C21 C20 -1.25(19) . . . . ?
C23 C22 C21 C24 178.18(13) . . . . ?
C3 C4 C5 C6 -178.15(13) . . . . ?
C19 C18 C23 C22 0.91(19) . . . . ?
C8 C9 C4 C3 178.96(11) . . . . ?
C8 C9 C4 C5 0.33(19) . . . . ?
C8 C7 C6 C5 0.0(2) . . . . ?
C7 C6 C5 C4 -0.3(2) . . . . ?
C22 C21 C20 C19 1.8(2) . . . . ?
C2 N1 C9 C4 -13.33(13) . . . . ?
C2 N1 C9 C8 166.88(12) . . . . ?
C5 C4 C3 N15 -41.65(19) . . . . ?
C5 C4 C3 C2 -167.70(13) . . . . ?
C14 O13 C2 N1 -71.34(14) . . . . ?
C14 O13 C2 C3 175.68(11) . . . . ?
C24 C21 C20 C19 -177.66(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.811
_oxdiff_exptl_absorpt_empirical_full_min 0.729
