# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_100423-73-bio2278_100k_final
_database_code_depnum_ccdc_archive 'CCDC 2130542'
loop_
_audit_author_name
_audit_author_address
'Bo Wang '
;Biogen
United States of America
;
_audit_update_record             
;
2021-12-22 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT934_100423-73-bio2278_100k_final 
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          3 Check
RESPONSE: They all are low angle reflections with h index -1 or -2. Considering the high quality of this structure, it is not likely due to a missed symmetry element or twinning.
;
# Added during the CSD deposition process: Wednesday 22 December 2021 02:44 PM
# end Validation Reply Form

_audit_creation_date             2021-09-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
(R)-N-(5-((3-((5-fluoropyrimidin-2-yl)methyl)piperidin-1-yl)methyl)thiazol-2-yl)acetamide
;
_chemical_formula_moiety         'C16 H20 F N5 O S'
_chemical_formula_sum            'C16 H20 F N5 O S'
_chemical_formula_weight         349.43
_chemical_absolute_configuration ad
_chemical_melting_point          437
_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'
F F 0.0727 0.0534 '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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   6.02205(5)
_cell_length_b                   10.98930(12)
_cell_length_c                   13.54829(16)
_cell_angle_alpha                76.0394(10)
_cell_angle_beta                 84.6111(8)
_cell_angle_gamma                78.5505(8)
_cell_volume                     851.802(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    49730
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.9720
_cell_measurement_theta_min      3.3490
_shelx_estimated_absorpt_T_max   0.848
_shelx_estimated_absorpt_T_min   0.714
_exptl_absorpt_coefficient_mu    1.899
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.108a (Rigaku Oxford Diffraction, 2021)
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    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -2 2 0.0498
-1 2 -2 0.0498
-1 -1 1 0.0589
1 2 -2 0.0470
-2 1 1 0.0572
2 -1 -1 0.0639
-1 0 2 0.0529
1 0 -2 0.0548
0 -1 2 0.0420
0 1 -2 0.0504
-1 2 2 0.0605
1 -2 -2 0.0689
0 1 2 0.0529
0 -1 -2 0.0721
0 2 1 0.0595
0 -2 -1 0.0595
0 -1 1 0.0398
0 1 -1 0.0500
-2 -1 0 0.0712
2 1 0 0.0771

_exptl_crystal_preparation       'evaporation in THF'
_exptl_crystal_recrystallization_method 'evaporation in THF'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
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
1.0000 -2.0000 2.0000 0.0092 0.0961 -0.5038
-1.0000 2.0000 -2.0000 -0.0092 -0.0961 0.5038
-1.0000 -1.0000 1.0000 -0.0014 -0.3058 -0.0834
1.0000 2.0000 -2.0000 -0.0012 0.3757 0.2791
-2.0000 1.0000 1.0000 0.1500 -0.4877 0.2724
2.0000 -1.0000 -1.0000 -0.1500 0.4877 -0.2724
-1.0000 -0.0000 2.0000 0.1566 -0.3217 -0.0357
1.0000 0.0000 -2.0000 -0.1566 0.3217 0.0357
0.0000 -1.0000 2.0000 0.0829 -0.1128 -0.2697
-0.0000 1.0000 -2.0000 -0.0829 0.1128 0.2697
-1.0000 2.0000 2.0000 0.3119 -0.2676 0.2078
1.0000 -2.0000 -2.0000 -0.3119 0.2676 -0.2078
0.0000 1.0000 2.0000 0.2382 -0.0587 -0.0263
-0.0000 -1.0000 -2.0000 -0.2382 0.0587 0.0263
-0.0000 2.0000 1.0000 0.2356 0.0112 0.1694
0.0000 -2.0000 -1.0000 -0.2356 -0.0112 -0.1694
0.0000 -1.0000 1.0000 0.0026 -0.0699 -0.1957
-0.0000 1.0000 -1.0000 -0.0026 0.0699 0.1957
-2.0000 -1.0000 0.0000 -0.0857 -0.4988 0.1029
2.0000 1.0000 -0.0000 0.0857 0.4988 -0.1029

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            66717
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.571
_diffrn_reflns_theta_min         3.365
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -28.00   0.50    0.10    --  -47.20 -68.00 -94.00  184
  2  ω     28.00 120.00   0.50    0.10    --   47.20  68.00  38.00  184
  3  ω    -24.00  66.00   0.50    0.10    --   47.20 -68.00 -94.00  180
  4  ω   -177.00 -87.00   0.50    0.40    -- -106.00 -68.00 -94.00  180
  5  ω    -96.00 -33.00   0.50    0.40    -- -106.00  68.00  38.00  126
  6  ω     35.00  92.00   0.50    0.40    --  107.75 -68.00 -94.00  114
  7  ω     89.00 178.00   0.50    0.40    --  107.75  68.00  38.00  178
  8  ω    -19.00   7.00   0.50    0.10    --   14.00  99.00  93.73   52
  9  ω     -9.00  17.00   0.50    0.10    --   18.00  86.00 141.21   52
 10  ω      6.00  33.00   0.50    0.10    --   26.00  70.00-108.98   54
 11  ω     11.00  37.00   0.50    0.10    --   30.00  67.00-170.54   52
 12  ω     17.00  46.00   0.50    0.10    --   34.00  62.00   9.55   58
 13  ω     18.00  48.00   0.50    0.10    --   34.00  61.00 -66.39   60
 14  ω     22.00  50.00   0.50    0.10    --   38.00  60.00 -99.29   56
 15  ω    -56.00 -27.00   0.50    0.10    --  -42.00 -58.00 -13.22   58
 16  ω    -53.00 -26.00   0.50    0.10    --  -42.00 -59.00 149.48   54
 17  ω    -53.00 -26.00   0.50    0.10    --  -42.00 -59.00  35.93   54
 18  ω    -56.00 -27.00   0.50    0.10    --  -42.00 -58.00  93.52   58
 19  ω    -95.00 -13.00   0.50    0.10    --  -47.20 125.00  30.00  164
 20  ω    -66.00  26.00   0.50    0.10    --  -47.20  68.00  38.00  184
 21  ω   -125.00 -39.00   0.50    0.10    --  -54.00 -55.00 -14.40  172
 22  ω   -125.00 -39.00   0.50    0.10    --  -54.00 -56.00  69.16  172
 23  ω   -130.00 -43.00   0.50    0.10    --  -58.00 -56.00-137.19  174
 24  ω   -130.00 -44.00   0.50    0.10    --  -58.00 -52.00 146.83  172
 25  ω   -138.00 -52.00   0.50    0.10    --  -66.00 -50.00  56.97  172
 26  ω   -142.00 -56.00   0.50    0.10    --  -70.00 -54.00 127.42  172
 27  ω   -142.00 -56.00   0.50    0.10    --  -70.00 -50.00 -48.85  172
 28  ω   -142.00 -56.00   0.50    0.10    --  -70.00 -53.00-132.35  172
 29  ω   -142.00 -56.00   0.50    0.10    --  -70.00 -52.00  46.56  172
 30  ω   -145.00 -60.00   0.50    0.10    --  -74.00 -54.00  36.45  170
 31  ω   -145.00 -60.00   0.50    0.10    --  -74.00 -54.00 152.34  170
 32  ω   -145.00 -59.00   0.50    0.10    --  -74.00 -55.00-155.80  172
 33  ω   -145.00 -60.00   0.50    0.10    --  -74.00 -53.00  66.90  170
 34  ω   -145.00 -59.00   0.50    0.10    --  -74.00 -56.00  21.99  172
 35  ω   -145.00 -59.00   0.50    0.10    --  -74.00 -56.00 -89.61  172
 36  ω   -145.00 -59.00   0.50    0.10    --  -74.00 -56.00 -41.40  172
 37  ω   -150.00 -64.00   0.50    0.40    --  -78.00 -51.00 -83.64  172
 38  ω   -150.00 -63.00   0.50    0.40    --  -78.00 -56.00  -5.97  174
 39  ω   -150.00 -64.00   0.50    0.40    --  -78.00 -54.00 113.27  172
 40  ω   -153.00 -67.00   0.50    0.40    --  -82.00 -55.00-165.75  172
 41  ω   -153.00 -68.00   0.50    0.40    --  -82.00 -52.00  61.71  170
 42  ω   -153.00 -68.00   0.50    0.40    --  -82.00 -51.00 -57.09  170
 43  ω   -158.00 -72.00   0.50    0.40    --  -86.00 -51.00-129.33  172
 44  ω   -161.00 -75.00   0.50    0.40    --  -90.00 -55.00 -65.06  172
 45  ω   -161.00 -76.00   0.50    0.40    --  -90.00 -50.00 176.14  170
 46  ω   -161.00 -77.00   0.50    0.40    --  -90.00 -56.00 111.49  168
 47  ω   -166.00 -79.00   0.50    0.40    --  -94.00 -56.00 -86.19  174
 48  ω   -169.00 -84.00   0.50    0.40    --  -98.00 -52.00 -22.45  170
 49  ω   -169.00 -83.00   0.50    0.40    --  -98.00 -56.00-177.99  172
 50  ω   -169.00 -84.00   0.50    0.40    --  -98.00 -52.00  51.91  170
 51  ω   -174.00 -89.00   0.50    0.40    -- -102.00 -60.00-118.86  170
 52  ω   -177.00 -93.00   0.50    0.40    -- -106.00 -63.00 -61.58  168
 53  ω   -177.00 -93.00   0.50    0.40    -- -106.00 -45.00  90.00  168
 54  ω    -78.00 -33.00   0.50    0.40    -- -106.00  61.00  30.00   90
 55  ω   -177.00 -91.00   0.50    0.40    -- -106.00 -61.00 -30.00  172
 56  ω   -177.00 -91.00   0.50    0.40    -- -106.00 -61.00 150.00  172
 57  ω   -177.00 -91.00   0.50    0.40    -- -106.00 -61.00 120.00  172
 58  ω   -129.00 -33.00   0.50    0.40    -- -106.00  77.00 -90.00  192
 59  ω   -126.00 -33.00   0.50    0.40    -- -106.00 144.00 149.27  186
 60  ω   -177.00 -91.00   0.50    0.40    -- -106.00 -61.00-150.00  172
 61  ω   -177.00 -92.00   0.50    0.40    -- -106.00 -62.00 138.28  170
 62  ω   -177.00 -90.00   0.50    0.40    -- -106.00 -60.00 -86.61  174
 63  ω   -177.00 -94.00   0.50    0.40    -- -106.00 -64.00-133.09  166
 64  ω   -177.00 -91.00   0.50    0.40    -- -106.00 -57.00 -80.96  172
 65  ω   -177.00 -90.00   0.50    0.40    -- -106.00 -59.00  41.04  174
 66  ω   -177.00 -91.00   0.50    0.40    -- -106.00 -61.00   0.00  172
 67  ω   -177.00 -90.00   0.50    0.40    -- -106.00 -60.00  19.59  174
 68  ω   -177.00 -91.00   0.50    0.40    -- -106.00 -61.00  30.00  172
 69  ω   -107.00 -33.00   0.50    0.40    -- -106.00 105.00  82.46  148
 70  ω   -177.00 -90.00   0.50    0.40    -- -106.00 -59.00 163.19  174
 71  ω   -177.00 -91.00   0.50    0.40    -- -106.00 -61.00-180.00  172
 72  ω   -177.00 -91.00   0.50    0.40    -- -106.00 -55.00  78.50  172
 73  ω     91.00 178.00   0.50    0.40    --  107.75  61.00-120.00  174
 74  ω     35.00 105.00   0.50    0.40    --  107.75 -95.00 150.00  140
 75  ω     35.00 105.00   0.50    0.40    --  107.75 -95.00  30.00  140
 76  ω     35.00 112.00   0.50    0.40    --  107.75-125.00 -60.00  154
 77  ω     94.00 169.00   0.50    0.40    --  107.75  15.00-150.00  150
 78  ω     35.00 105.00   0.50    0.40    --  107.75 -95.00  90.00  140
 79  ω     35.00 105.00   0.50    0.40    --  107.75 -95.00 -30.00  140
 80  ω     35.00  74.00   0.50    0.40    --  107.75 -61.00 -60.00   78
 81  ω     35.00 105.00   0.50    0.40    --  107.75 -95.00-150.00  140
 82  ω     35.00 105.00   0.50    0.40    --  107.75 -95.00 120.00  140
 83  ω     35.00 105.00   0.50    0.40    --  107.75 -95.00  60.00  140
 84  ω     35.00 105.00   0.50    0.40    --  107.75 -95.00 -60.00  140
 85  ω     91.00 178.00   0.50    0.40    --  107.75  61.00 -30.00  174
 86  ω    -70.00  26.00   0.50    0.10    --  -47.20  77.00 120.00  192
 87  ω    -70.00  26.00   0.50    0.10    --  -47.20  77.00-180.00  192
 88  ω    -70.00  26.00   0.50    0.10    --  -47.20  77.00-120.00  192
 89  ω    -70.00  26.00   0.50    0.10    --  -47.20  77.00-150.00  192
 90  ω    -70.00  26.00   0.50    0.10    --  -47.20  77.00 -30.00  192
 91  ω    -70.00  26.00   0.50    0.10    --  -47.20  77.00 150.00  192
 92  ω    -70.00  26.00   0.50    0.10    --  -47.20  77.00   0.00  192
 93  ω    -70.00  26.00   0.50    0.10    --  -47.20  77.00  90.00  192
 94  ω    -70.00  26.00   0.50    0.10    --  -47.20  77.00  60.00  192
 95  ω    -70.00  26.00   0.50    0.10    --  -47.20  77.00 -90.00  192
 96  ω    -70.00  26.00   0.50    0.10    --  -47.20  77.00 -60.00  192
 97  ω    -70.00  26.00   0.50    0.10    --  -47.20  77.00  30.00  192
 98  ω    -24.00  70.00   0.50    0.10    --   47.20 -77.00  90.00  188
 99  ω    -24.00  70.00   0.50    0.10    --   47.20 -77.00  30.00  188
100  ω    -24.00  70.00   0.50    0.10    --   47.20 -77.00   0.00  188
101  ω    -24.00  70.00   0.50    0.10    --   47.20 -77.00 -30.00  188
102  ω    -24.00  70.00   0.50    0.10    --   47.20 -77.00 -60.00  188
103  ω    -24.00  70.00   0.50    0.10    --   47.20 -77.00-120.00  188
104  ω    -24.00  70.00   0.50    0.10    --   47.20 -77.00-180.00  188
105  ω    -24.00  70.00   0.50    0.10    --   47.20 -77.00 -90.00  188
106  ω    -24.00  70.00   0.50    0.10    --   47.20 -77.00-150.00  188
107  ω    -24.00  70.00   0.50    0.10    --   47.20 -77.00  60.00  188
108  ω   -130.00 -43.00   0.50    0.10    --  -58.00 -56.00 -49.48  174
109  ω   -130.00 -43.00   0.50    0.10    --  -58.00 -56.00  95.80  174
110  ω   -138.00 -52.00   0.50    0.10    --  -66.00 -54.00 178.38  172
111  ω   -138.00 -52.00   0.50    0.10    --  -66.00 -52.00 127.71  172
112  ω   -142.00 -57.00   0.50    0.10    --  -70.00 -49.00-131.65  170
113  ω   -145.00 -60.00   0.50    0.10    --  -74.00 -54.00 160.01  170
114  ω   -145.00 -59.00   0.50    0.10    --  -74.00 -55.00   1.40  172
115  ω   -145.00 -60.00   0.50    0.10    --  -74.00 -50.00-149.49  170
116  ω   -150.00 -63.00   0.50    0.40    --  -78.00 -56.00-178.57  174
117  ω   -150.00 -64.00   0.50    0.40    --  -78.00 -54.00 -60.48  172
118  ω   -158.00 -72.00   0.50    0.40    --  -86.00 -51.00 123.90  172
119  ω   -161.00 -77.00   0.50    0.40    --  -90.00 -46.00  75.08  168
120  ω   -166.00 -79.00   0.50    0.40    --  -94.00 -56.00 164.69  174
121  ω   -169.00 -84.00   0.50    0.40    --  -98.00 -54.00 122.15  170
122  ω   -169.00 -83.00   0.50    0.40    --  -98.00 -57.00 -71.15  172
123  ω   -174.00 -87.00   0.50    0.40    -- -102.00 -55.00  46.21  174
124  ω   -177.00 -90.00   0.50    0.40    -- -106.00 -59.00 -42.95  174
125  ω   -177.00 -91.00   0.50    0.40    -- -106.00 -56.00  38.68  172
126  ω   -177.00 -93.00   0.50    0.40    -- -106.00 -45.00-150.00  168
127  ω   -177.00 -95.00   0.50    0.40    -- -106.00 -65.00  61.59  164
128  ω   -177.00 -95.00   0.50    0.40    -- -106.00 -65.00-152.30  164
129  ω   -106.00 -33.00   0.50    0.40    -- -106.00  98.00 -96.69  146
130  ω   -177.00 -91.00   0.50    0.40    -- -106.00 -61.00  99.94  172
131  ω     35.00  74.00   0.50    0.40    --  107.75 -61.00-180.00   78
132  ω     35.00 131.00   0.50    0.40    --  107.75 -77.00-180.00  192
133  ω     95.00 178.00   0.50    0.40    --  107.75  45.00-150.00  166
134  ω     35.00  74.00   0.50    0.40    --  107.75 -61.00  30.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0039936000
_diffrn_orient_matrix_UB_12      0.0776833000
_diffrn_orient_matrix_UB_13      0.0802771000
_diffrn_orient_matrix_UB_21      0.2359101000
_diffrn_orient_matrix_UB_22      0.0270289000
_diffrn_orient_matrix_UB_23      -0.0428878000
_diffrn_orient_matrix_UB_31      -0.1123340000
_diffrn_orient_matrix_UB_32      0.1217238000
_diffrn_orient_matrix_UB_33      -0.0740086000
_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         0.864
_reflns_Friedel_fraction_full    0.899
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                6533
_reflns_number_total             6654
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.108a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 2946 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(5)
_refine_ls_extinction_coef       0.0024(4)
_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   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6654
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.085
_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)+(0.0315P)²+0.2519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0681
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6B(H6B), C6A(H6A)
2.b Secondary CH2 refined with riding coordinates:
 C5B(H5BA,H5BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB), C9B(H9BA,H9BB), C10B(H10A,
 H10B), C11B(H11A,H11B), C5A(H5AA,H5AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB),
 C9A(H9AA,H9AB), C10A(H10C,H10D), C11A(H11C,H11D)
2.c Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3B(H3B), C13B(H13B), N5B(H5B), C2A(H2A), C3A(H3A), C13A(H13A),
 N5A(H5A)
2.d Idealised Me refined as rotating group:
 C16B(H16A,H16B,H16C), C16A(H16D,H16E,H16F)
;
_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
F2 F 0.3102(3) 1.41486(15) 1.06278(12) 0.0338(3) Uani 1 1 d . . . . .
C1B C 0.4504(4) 1.3229(2) 1.02508(18) 0.0246(5) Uani 1 1 d . . . . .
C2B C 0.6810(4) 1.3104(3) 1.0273(2) 0.0283(5) Uani 1 1 d . . . . .
H2B H 0.743264 1.364084 1.058313 0.034 Uiso 1 1 calc R U . . .
C3B C 0.3618(4) 1.2423(2) 0.98273(19) 0.0249(5) Uani 1 1 d . . . . .
H3B H 0.201994 1.249222 0.982981 0.030 Uiso 1 1 calc R U . . .
C4B C 0.7213(4) 1.1490(2) 0.94349(18) 0.0200(5) Uani 1 1 d . . . . .
C5B C 0.8798(4) 1.0513(2) 0.89666(18) 0.0215(5) Uani 1 1 d . . . . .
H5BA H 0.933591 0.976363 0.951554 0.026 Uiso 1 1 calc R U . . .
H5BB H 1.013870 1.088080 0.864915 0.026 Uiso 1 1 calc R U . . .
C6B C 0.7752(4) 1.0064(2) 0.81669(18) 0.0199(5) Uani 1 1 d . . . . .
H6B H 0.637742 0.971681 0.849027 0.024 Uiso 1 1 calc R U . . .
C7B C 0.9393(4) 0.8999(2) 0.77981(19) 0.0206(5) Uani 1 1 d . . . . .
H7BA H 1.073432 0.933156 0.743879 0.025 Uiso 1 1 calc R U . . .
H7BB H 0.991984 0.830524 0.838920 0.025 Uiso 1 1 calc R U . . .
C8B C 0.7015(5) 1.1134(3) 0.7238(2) 0.0251(5) Uani 1 1 d . . . . .
H8BA H 0.590869 1.182500 0.745861 0.030 Uiso 1 1 calc R U . . .
H8BB H 0.834782 1.149512 0.690133 0.030 Uiso 1 1 calc R U . . .
C9B C 0.5941(5) 1.0618(3) 0.6491(2) 0.0294(6) Uani 1 1 d . . . . .
H9BA H 0.557861 1.129672 0.586937 0.035 Uiso 1 1 calc R U . . .
H9BB H 0.450866 1.035089 0.680123 0.035 Uiso 1 1 calc R U . . .
C10B C 0.7549(5) 0.9485(3) 0.6207(2) 0.0269(6) Uani 1 1 d . . . . .
H10A H 0.677954 0.912106 0.576216 0.032 Uiso 1 1 calc R U . . .
H10B H 0.889751 0.977741 0.582053 0.032 Uiso 1 1 calc R U . . .
C11B C 0.9717(4) 0.7390(3) 0.6821(2) 0.0219(5) Uani 1 1 d . . . . .
H11A H 1.056180 0.685608 0.741442 0.026 Uiso 1 1 calc R U . . .
H11B H 1.083478 0.767835 0.627397 0.026 Uiso 1 1 calc R U . . .
C12B C 0.8323(4) 0.6614(3) 0.6457(2) 0.0212(5) Uani 1 1 d . . . . .
C13B C 0.8510(4) 0.6187(3) 0.5591(2) 0.0231(5) Uani 1 1 d . . . . .
H13B H 0.962512 0.639649 0.506595 0.028 Uiso 1 1 calc R U . . .
C14B C 0.5636(4) 0.5287(2) 0.63320(19) 0.0193(5) Uani 1 1 d . . . . .
C15B C 0.2650(4) 0.4298(3) 0.7344(2) 0.0212(5) Uani 1 1 d . . . . .
C16B C 0.1062(4) 0.3397(3) 0.7349(2) 0.0246(6) Uani 1 1 d . . . . .
H16A H 0.193498 0.253338 0.739707 0.037 Uiso 1 1 calc R U . . .
H16B H 0.024172 0.366964 0.671838 0.037 Uiso 1 1 calc R U . . .
H16C H -0.002398 0.340289 0.793421 0.037 Uiso 1 1 calc R U . . .
N1B N 0.8190(3) 1.2222(2) 0.98573(16) 0.0254(4) Uani 1 1 d . . . . .
N2B N 0.4979(3) 1.1545(2) 0.94126(16) 0.0242(4) Uani 1 1 d . . . . .
N3B N 0.8273(3) 0.8498(2) 0.71097(16) 0.0207(4) Uani 1 1 d . . . . .
N4B N 0.6978(4) 0.5425(2) 0.55124(16) 0.0216(5) Uani 1 1 d . . . . .
N5B N 0.3969(3) 0.4553(2) 0.64573(16) 0.0200(4) Uani 1 1 d . . . . .
H5B H 0.373870 0.423434 0.594694 0.024 Uiso 1 1 calc R U . . .
O1B O 0.2816(3) 0.47550(19) 0.80619(14) 0.0247(4) Uani 1 1 d . . . . .
S1B S 0.61124(8) 0.60627(5) 0.72404(4) 0.02181(14) Uani 1 1 d . . . . .
C1A C 0.6914(4) -0.3301(3) -0.0151(2) 0.0264(5) Uani 1 1 d . . . . .
C2A C 0.7896(4) -0.2660(3) 0.03978(18) 0.0267(5) Uani 1 1 d . . . . .
H2A H 0.949565 -0.283113 0.044893 0.032 Uiso 1 1 calc R U . . .
C3A C 0.4606(4) -0.3064(3) -0.0208(2) 0.0285(5) Uani 1 1 d . . . . .
H3A H 0.392046 -0.351547 -0.057539 0.034 Uiso 1 1 calc R U . . .
C4A C 0.4373(4) -0.1588(2) 0.07545(17) 0.0229(5) Uani 1 1 d . . . . .
C5A C 0.2937(4) -0.0608(2) 0.12515(18) 0.0238(5) Uani 1 1 d . . . . .
H5AA H 0.188340 -0.002785 0.075139 0.029 Uiso 1 1 calc R U . . .
H5AB H 0.392859 -0.009387 0.144541 0.029 Uiso 1 1 calc R U . . .
C6A C 0.1549(4) -0.1174(2) 0.22032(19) 0.0232(5) Uani 1 1 d . . . . .
H6A H 0.041978 -0.159954 0.198495 0.028 Uiso 1 1 calc R U . . .
C7A C 0.0252(4) -0.0106(2) 0.2687(2) 0.0235(5) Uani 1 1 d . . . . .
H7AA H -0.065801 0.054583 0.216842 0.028 Uiso 1 1 calc R U . . .
H7AB H -0.080453 -0.045690 0.323796 0.028 Uiso 1 1 calc R U . . .
C8A C 0.2997(4) -0.2163(3) 0.3004(2) 0.0241(5) Uani 1 1 d . . . . .
H8AA H 0.199296 -0.259678 0.353593 0.029 Uiso 1 1 calc R U . . .
H8AB H 0.395365 -0.281423 0.267789 0.029 Uiso 1 1 calc R U . . .
C9A C 0.4514(5) -0.1533(3) 0.3495(2) 0.0253(5) Uani 1 1 d . . . . .
H9AA H 0.531084 -0.217263 0.405667 0.030 Uiso 1 1 calc R U . . .
H9AB H 0.567101 -0.121004 0.298371 0.030 Uiso 1 1 calc R U . . .
C10A C 0.3108(4) -0.0437(3) 0.3907(2) 0.0243(5) Uani 1 1 d . . . . .
H10C H 0.205453 -0.077380 0.446556 0.029 Uiso 1 1 calc R U . . .
H10D H 0.412433 -0.001355 0.418996 0.029 Uiso 1 1 calc R U . . .
C11A C 0.0510(4) 0.1580(3) 0.3485(2) 0.0224(5) Uani 1 1 d . . . . .
H11C H -0.047929 0.126044 0.407769 0.027 Uiso 1 1 calc R U . . .
H11D H -0.047863 0.213311 0.294664 0.027 Uiso 1 1 calc R U . . .
C12A C 0.1989(4) 0.2362(2) 0.3796(2) 0.0206(5) Uani 1 1 d . . . . .
C13A C 0.1843(4) 0.2790(3) 0.4653(2) 0.0212(5) Uani 1 1 d . . . . .
H13A H 0.076239 0.256613 0.519117 0.025 Uiso 1 1 calc R U . . .
C14A C 0.4637(4) 0.3732(2) 0.38790(19) 0.0190(5) Uani 1 1 d . . . . .
C15A C 0.7578(4) 0.4767(2) 0.28681(19) 0.0201(5) Uani 1 1 d . . . . .
C16A C 0.9212(4) 0.5631(3) 0.2889(2) 0.0222(5) Uani 1 1 d . . . . .
H16D H 1.042432 0.553808 0.236185 0.033 Uiso 1 1 calc R U . . .
H16E H 0.986977 0.540101 0.355801 0.033 Uiso 1 1 calc R U . . .
H16F H 0.840770 0.651749 0.275929 0.033 Uiso 1 1 calc R U . . .
F1A F 0.8240(3) -0.41535(17) -0.06228(12) 0.0365(4) Uani 1 1 d . . . . .
N1A N 0.6617(3) -0.1800(2) 0.08570(16) 0.0266(4) Uani 1 1 d . . . . .
N2A N 0.3309(3) -0.2203(2) 0.02478(17) 0.0263(5) Uani 1 1 d . . . . .
N3A N 0.1809(3) 0.0497(2) 0.31079(16) 0.0202(4) Uani 1 1 d . . . . .
N4A N 0.3341(3) 0.3572(2) 0.47160(16) 0.0210(4) Uani 1 1 d . . . . .
N5A N 0.6304(4) 0.4464(2) 0.37545(16) 0.0199(4) Uani 1 1 d . . . . .
H5A H 0.656280 0.475433 0.427611 0.024 Uiso 1 1 calc R U . . .
O1A O 0.7357(3) 0.4369(2) 0.21231(14) 0.0272(4) Uani 1 1 d . . . . .
S1A S 0.41338(8) 0.29454(5) 0.29796(4) 0.02107(14) Uani 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
F2 C1B 1.350(3) . ?
C1B C2B 1.370(3) . ?
C1B C3B 1.374(3) . ?
C2B H2B 0.9500 . ?
C2B N1B 1.343(3) . ?
C3B H3B 0.9500 . ?
C3B N2B 1.334(3) . ?
C4B C5B 1.508(3) . ?
C4B N1B 1.339(3) . ?
C4B N2B 1.337(3) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B C6B 1.524(3) . ?
C6B H6B 1.0000 . ?
C6B C7B 1.526(3) . ?
C6B C8B 1.532(4) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7B N3B 1.464(3) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C9B 1.520(4) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C9B C10B 1.522(4) . ?
C10B H10A 0.9900 . ?
C10B H10B 0.9900 . ?
C10B N3B 1.461(4) . ?
C11B H11A 0.9900 . ?
C11B H11B 0.9900 . ?
C11B C12B 1.496(3) . ?
C11B N3B 1.462(3) . ?
C12B C13B 1.352(4) . ?
C12B S1B 1.735(3) . ?
C13B H13B 0.9500 . ?
C13B N4B 1.390(3) . ?
C14B N4B 1.307(3) . ?
C14B N5B 1.382(3) . ?
C14B S1B 1.730(3) . ?
C15B C16B 1.504(3) . ?
C15B N5B 1.378(3) . ?
C15B O1B 1.218(3) . ?
C16B H16A 0.9800 . ?
C16B H16B 0.9800 . ?
C16B H16C 0.9800 . ?
N5B H5B 0.8800 . ?
C1A C2A 1.378(3) . ?
C1A C3A 1.368(3) . ?
C1A F1A 1.349(3) . ?
C2A H2A 0.9500 . ?
C2A N1A 1.333(3) . ?
C3A H3A 0.9500 . ?
C3A N2A 1.337(3) . ?
C4A C5A 1.494(3) . ?
C4A N1A 1.340(3) . ?
C4A N2A 1.348(3) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A C6A 1.538(3) . ?
C6A H6A 1.0000 . ?
C6A C7A 1.526(3) . ?
C6A C8A 1.533(4) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A N3A 1.474(3) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.531(4) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.521(4) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C10A N3A 1.464(4) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C11A C12A 1.502(3) . ?
C11A N3A 1.463(4) . ?
C12A C13A 1.344(4) . ?
C12A S1A 1.738(2) . ?
C13A H13A 0.9500 . ?
C13A N4A 1.385(3) . ?
C14A N4A 1.311(3) . ?
C14A N5A 1.381(3) . ?
C14A S1A 1.733(2) . ?
C15A C16A 1.503(3) . ?
C15A N5A 1.370(3) . ?
C15A O1A 1.220(3) . ?
C16A H16D 0.9800 . ?
C16A H16E 0.9800 . ?
C16A H16F 0.9800 . ?
N5A H5A 0.8800 . ?

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
F2 C1B C2B 120.5(2) . . ?
F2 C1B C3B 119.9(2) . . ?
C2B C1B C3B 119.6(2) . . ?
C1B C2B H2B 120.0 . . ?
N1B C2B C1B 120.1(2) . . ?
N1B C2B H2B 120.0 . . ?
C1B C3B H3B 119.7 . . ?
N2B C3B C1B 120.7(2) . . ?
N2B C3B H3B 119.7 . . ?
N1B C4B C5B 116.25(19) . . ?
N2B C4B C5B 118.30(19) . . ?
N2B C4B N1B 125.4(2) . . ?
C4B C5B H5BA 108.6 . . ?
C4B C5B H5BB 108.6 . . ?
C4B C5B C6B 114.49(19) . . ?
H5BA C5B H5BB 107.6 . . ?
C6B C5B H5BA 108.6 . . ?
C6B C5B H5BB 108.6 . . ?
C5B C6B H6B 108.0 . . ?
C5B C6B C7B 111.18(19) . . ?
C5B C6B C8B 113.3(2) . . ?
C7B C6B H6B 108.0 . . ?
C7B C6B C8B 108.3(2) . . ?
C8B C6B H6B 108.0 . . ?
C6B C7B H7BA 109.6 . . ?
C6B C7B H7BB 109.6 . . ?
H7BA C7B H7BB 108.2 . . ?
N3B C7B C6B 110.10(19) . . ?
N3B C7B H7BA 109.6 . . ?
N3B C7B H7BB 109.6 . . ?
C6B C8B H8BA 109.7 . . ?
C6B C8B H8BB 109.7 . . ?
H8BA C8B H8BB 108.2 . . ?
C9B C8B C6B 110.0(2) . . ?
C9B C8B H8BA 109.7 . . ?
C9B C8B H8BB 109.7 . . ?
C8B C9B H9BA 109.6 . . ?
C8B C9B H9BB 109.6 . . ?
C8B C9B C10B 110.5(2) . . ?
H9BA C9B H9BB 108.1 . . ?
C10B C9B H9BA 109.6 . . ?
C10B C9B H9BB 109.6 . . ?
C9B C10B H10A 109.3 . . ?
C9B C10B H10B 109.3 . . ?
H10A C10B H10B 108.0 . . ?
N3B C10B C9B 111.5(2) . . ?
N3B C10B H10A 109.3 . . ?
N3B C10B H10B 109.3 . . ?
H11A C11B H11B 108.1 . . ?
C12B C11B H11A 109.5 . . ?
C12B C11B H11B 109.5 . . ?
N3B C11B H11A 109.5 . . ?
N3B C11B H11B 109.5 . . ?
N3B C11B C12B 110.7(2) . . ?
C11B C12B S1B 119.24(19) . . ?
C13B C12B C11B 131.0(2) . . ?
C13B C12B S1B 109.71(19) . . ?
C12B C13B H13B 121.9 . . ?
C12B C13B N4B 116.2(2) . . ?
N4B C13B H13B 121.9 . . ?
N4B C14B N5B 121.4(2) . . ?
N4B C14B S1B 115.67(18) . . ?
N5B C14B S1B 122.88(18) . . ?
N5B C15B C16B 114.5(2) . . ?
O1B C15B C16B 123.8(2) . . ?
O1B C15B N5B 121.7(2) . . ?
C15B C16B H16A 109.5 . . ?
C15B C16B H16B 109.5 . . ?
C15B C16B H16C 109.5 . . ?
H16A C16B H16B 109.5 . . ?
H16A C16B H16C 109.5 . . ?
H16B C16B H16C 109.5 . . ?
C4B N1B C2B 117.2(2) . . ?
C3B N2B C4B 117.0(2) . . ?
C10B N3B C7B 111.2(2) . . ?
C10B N3B C11B 110.7(2) . . ?
C11B N3B C7B 111.7(2) . . ?
C14B N4B C13B 109.6(2) . . ?
C14B N5B H5B 118.4 . . ?
C15B N5B C14B 123.1(2) . . ?
C15B N5B H5B 118.4 . . ?
C14B S1B C12B 88.82(12) . . ?
C3A C1A C2A 119.5(2) . . ?
F1A C1A C2A 119.6(2) . . ?
F1A C1A C3A 121.0(2) . . ?
C1A C2A H2A 119.8 . . ?
N1A C2A C1A 120.5(2) . . ?
N1A C2A H2A 119.8 . . ?
C1A C3A H3A 119.7 . . ?
N2A C3A C1A 120.5(2) . . ?
N2A C3A H3A 119.7 . . ?
N1A C4A C5A 117.5(2) . . ?
N1A C4A N2A 125.0(2) . . ?
N2A C4A C5A 117.5(2) . . ?
C4A C5A H5AA 108.8 . . ?
C4A C5A H5AB 108.8 . . ?
C4A C5A C6A 113.8(2) . . ?
H5AA C5A H5AB 107.7 . . ?
C6A C5A H5AA 108.8 . . ?
C6A C5A H5AB 108.8 . . ?
C5A C6A H6A 108.2 . . ?
C7A C6A C5A 109.7(2) . . ?
C7A C6A H6A 108.2 . . ?
C7A C6A C8A 109.1(2) . . ?
C8A C6A C5A 113.4(2) . . ?
C8A C6A H6A 108.2 . . ?
C6A C7A H7AA 109.4 . . ?
C6A C7A H7AB 109.4 . . ?
H7AA C7A H7AB 108.0 . . ?
N3A C7A C6A 111.28(19) . . ?
N3A C7A H7AA 109.4 . . ?
N3A C7A H7AB 109.4 . . ?
C6A C8A H8AA 109.4 . . ?
C6A C8A H8AB 109.4 . . ?
H8AA C8A H8AB 108.0 . . ?
C9A C8A C6A 111.1(2) . . ?
C9A C8A H8AA 109.4 . . ?
C9A C8A H8AB 109.4 . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 108.1 . . ?
C10A C9A C8A 110.5(2) . . ?
C10A C9A H9AA 109.5 . . ?
C10A C9A H9AB 109.5 . . ?
C9A C10A H10C 109.4 . . ?
C9A C10A H10D 109.4 . . ?
H10C C10A H10D 108.0 . . ?
N3A C10A C9A 111.1(2) . . ?
N3A C10A H10C 109.4 . . ?
N3A C10A H10D 109.4 . . ?
H11C C11A H11D 107.8 . . ?
C12A C11A H11C 109.0 . . ?
C12A C11A H11D 109.0 . . ?
N3A C11A H11C 109.0 . . ?
N3A C11A H11D 109.0 . . ?
N3A C11A C12A 113.0(2) . . ?
C11A C12A S1A 121.48(19) . . ?
C13A C12A C11A 128.8(2) . . ?
C13A C12A S1A 109.58(18) . . ?
C12A C13A H13A 121.6 . . ?
C12A C13A N4A 116.9(2) . . ?
N4A C13A H13A 121.6 . . ?
N4A C14A N5A 120.9(2) . . ?
N4A C14A S1A 115.47(18) . . ?
N5A C14A S1A 123.65(18) . . ?
N5A C15A C16A 114.8(2) . . ?
O1A C15A C16A 123.5(2) . . ?
O1A C15A N5A 121.6(2) . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C2A N1A C4A 117.3(2) . . ?
C3A N2A C4A 117.2(2) . . ?
C10A N3A C7A 110.4(2) . . ?
C11A N3A C7A 109.34(19) . . ?
C11A N3A C10A 111.7(2) . . ?
C14A N4A C13A 109.4(2) . . ?
C14A N5A H5A 118.0 . . ?
C15A N5A C14A 124.0(2) . . ?
C15A N5A H5A 118.0 . . ?
C14A S1A C12A 88.72(12) . . ?

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
F2 C1B C2B N1B -177.2(2) . . . . ?
F2 C1B C3B N2B 177.1(2) . . . . ?
C1B C2B N1B C4B -0.2(4) . . . . ?
C1B C3B N2B C4B 0.3(4) . . . . ?
C2B C1B C3B N2B -1.9(4) . . . . ?
C3B C1B C2B N1B 1.9(4) . . . . ?
C4B C5B C6B C7B -175.1(2) . . . . ?
C4B C5B C6B C8B 62.6(3) . . . . ?
C5B C4B N1B C2B 179.6(2) . . . . ?
C5B C4B N2B C3B -179.6(2) . . . . ?
C5B C6B C7B N3B 174.32(19) . . . . ?
C5B C6B C8B C9B -178.7(2) . . . . ?
C6B C7B N3B C10B 61.5(3) . . . . ?
C6B C7B N3B C11B -174.3(2) . . . . ?
C6B C8B C9B C10B -54.8(3) . . . . ?
C7B C6B C8B C9B 57.5(3) . . . . ?
C8B C6B C7B N3B -60.6(2) . . . . ?
C8B C9B C10B N3B 54.8(3) . . . . ?
C9B C10B N3B C7B -58.2(3) . . . . ?
C9B C10B N3B C11B 177.0(2) . . . . ?
C11B C12B C13B N4B 176.8(3) . . . . ?
C11B C12B S1B C14B -177.2(2) . . . . ?
C12B C11B N3B C7B 159.1(2) . . . . ?
C12B C11B N3B C10B -76.4(3) . . . . ?
C12B C13B N4B C14B 0.1(4) . . . . ?
C13B C12B S1B C14B 0.4(2) . . . . ?
C16B C15B N5B C14B -175.5(2) . . . . ?
N1B C4B C5B C6B -157.8(2) . . . . ?
N1B C4B N2B C3B 1.5(4) . . . . ?
N2B C4B C5B C6B 23.2(3) . . . . ?
N2B C4B N1B C2B -1.5(4) . . . . ?
N3B C11B C12B C13B 127.6(3) . . . . ?
N3B C11B C12B S1B -55.4(3) . . . . ?
N4B C14B N5B C15B 174.4(2) . . . . ?
N4B C14B S1B C12B -0.4(2) . . . . ?
N5B C14B N4B C13B -179.0(2) . . . . ?
N5B C14B S1B C12B 178.9(2) . . . . ?
O1B C15B N5B C14B 3.2(4) . . . . ?
S1B C12B C13B N4B -0.4(3) . . . . ?
S1B C14B N4B C13B 0.3(3) . . . . ?
S1B C14B N5B C15B -4.9(4) . . . . ?
C1A C2A N1A C4A -0.5(4) . . . . ?
C1A C3A N2A C4A 0.2(4) . . . . ?
C2A C1A C3A N2A 1.1(4) . . . . ?
C3A C1A C2A N1A -1.0(4) . . . . ?
C4A C5A C6A C7A 176.79(19) . . . . ?
C4A C5A C6A C8A 54.5(3) . . . . ?
C5A C4A N1A C2A -178.9(2) . . . . ?
C5A C4A N2A C3A 179.0(2) . . . . ?
C5A C6A C7A N3A -67.1(3) . . . . ?
C5A C6A C8A C9A 68.9(3) . . . . ?
C6A C7A N3A C10A -61.4(3) . . . . ?
C6A C7A N3A C11A 175.3(2) . . . . ?
C6A C8A C9A C10A 53.3(3) . . . . ?
C7A C6A C8A C9A -53.7(3) . . . . ?
C8A C6A C7A N3A 57.7(3) . . . . ?
C8A C9A C10A N3A -56.2(3) . . . . ?
C9A C10A N3A C7A 60.1(3) . . . . ?
C9A C10A N3A C11A -178.0(2) . . . . ?
C11A C12A C13A N4A -175.6(3) . . . . ?
C11A C12A S1A C14A 175.8(2) . . . . ?
C12A C11A N3A C7A -172.0(2) . . . . ?
C12A C11A N3A C10A 65.4(3) . . . . ?
C12A C13A N4A C14A 0.1(3) . . . . ?
C13A C12A S1A C14A -0.3(2) . . . . ?
C16A C15A N5A C14A 177.0(2) . . . . ?
F1A C1A C2A N1A 179.0(2) . . . . ?
F1A C1A C3A N2A -178.9(2) . . . . ?
N1A C4A C5A C6A -107.1(2) . . . . ?
N1A C4A N2A C3A -1.9(4) . . . . ?
N2A C4A C5A C6A 72.1(3) . . . . ?
N2A C4A N1A C2A 2.0(4) . . . . ?
N3A C11A C12A C13A -132.4(3) . . . . ?
N3A C11A C12A S1A 52.4(3) . . . . ?
N4A C14A N5A C15A -173.8(3) . . . . ?
N4A C14A S1A C12A 0.4(2) . . . . ?
N5A C14A N4A C13A -179.2(2) . . . . ?
N5A C14A S1A C12A 179.2(2) . . . . ?
O1A C15A N5A C14A -2.1(4) . . . . ?
S1A C12A C13A N4A 0.2(3) . . . . ?
S1A C14A N4A C13A -0.3(3) . . . . ?
S1A C14A N5A C15A 7.4(4) . . . . ?

_olex2_exptl_crystal_mounting_method 'Mounted with Paraton-N oil'
_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 1.185
_oxdiff_exptl_absorpt_empirical_full_min 0.869



####################################################################### 
# 
# 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_540p2s3_p1_x-final
_database_code_depnum_ccdc_archive 'CCDC 2130868'
loop_
_audit_author_name
_audit_author_address
'Jessica Bruhn'
;NanoImaging Services
United States of America
;
_audit_update_record             
;
2021-12-24 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;

_audit_creation_date             2021-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            
N-(5-{[(3R)-3-[(5-fluoropyrimidin-2-yl)methyl]piperidin-1-yl]methyl}-1,3-thiazol-2-yl)acetamide
_chemical_name_systematic        
N-(5-{[(3R)-3-[(5-fluoropyrimidin-2-yl)methyl]piperidin-1-yl]methyl}-1,3-thiazol-2-yl)acetamide
_chemical_formula_moiety         'C16 H20 F N5 O S'
_chemical_formula_sum            'C16 H20 F N5 O S'
_chemical_formula_weight         349.43
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 'International Tables Vol C Tables 4.3.1.1 and 4.3.2.2'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.3.1.1 and 4.3.2.2'
F F 0.0000 0.0000 'International Tables Vol C Tables 4.3.1.1 and 4.3.2.2'
N N 0.0000 0.0000 'International Tables Vol C Tables 4.3.1.1 and 4.3.2.2'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.3.1.1 and 4.3.2.2'
S S 0.0000 0.0000 'International Tables Vol C Tables 4.3.1.1 and 4.3.2.2'

_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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
_cell_length_a                   6.0289(12)
_cell_length_b                   10.902(2)
_cell_length_c                   13.522(3)
_cell_angle_alpha                75.67(3)
_cell_angle_beta                 84.27(3)
_cell_angle_gamma                78.20(3)
_cell_volume                     841.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14102
_cell_measurement_temperature    80(2)
_cell_measurement_theta_max      1.39
_cell_measurement_theta_min      0.11
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'electron diffraction, unknown absorption'
_exptl_absorpt_special_details   dials.scale
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             141
_exptl_crystal_size_max          0.0012
_exptl_crystal_size_mid          0.0006
_exptl_crystal_size_min          0.0001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2564
_diffrn_reflns_av_unetI/netI     0.3166
_diffrn_reflns_Laue_measured_fraction_full 0.928
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20220
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        0.800
_diffrn_reflns_theta_max         0.800
_diffrn_reflns_theta_min         0.055
_diffrn_ambient_temperature      80.15
_diffrn_detector_area_resol_mean 35.7
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'Thermo Fisher Glacios at 200keV'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           electron
_diffrn_radiation_wavelength     0.02501
_diffrn_source                   'transmission electron microscope'
_diffrn_standards_number         0
_diffrn_detector                 CMOS
_diffrn_detector_type            'Thermo Fisher CETA-D'
_diffrn_measurement_device       'transmission electron microscope'
_diffrn_radiation_probe          electron
_diffrn_source_type              'Thermo Fisher Glacios at 200keV'
_diffrn_source_voltage           200
_reflns_Friedel_coverage         0.982
_reflns_Friedel_fraction_full    0.912
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                1738
_reflns_number_total             4510
_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       'dials.cosym (Gildea, et al., 2018)'
_computing_data_collection       'Leginon (Cheng et al., 2021)'
_computing_data_reduction        'DIALS (Clabbers et al., 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD (Schneider, 2002)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         4510
_refine_ls_number_restraints     315
_refine_ls_R_factor_all          0.2291
_refine_ls_R_factor_gt           0.1481
_refine_ls_restrained_S_all      0.918
_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)+(0.1828P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3243
_refine_ls_wR_factor_ref         0.3507
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.004 and sigma
for terminal atoms of 0.004
3.a Ternary CH refined with riding coordinates:
 C6B(H6B), C6A(H6A)
3.b Secondary CH2 refined with riding coordinates:
 C11B(H11A,H11B), C5B(H5BA,H5BB), C5A(H5AA,H5AB), C10B(H10A,H10B), C9A(H9AA,
 H9AB), C8B(H8BA,H8BB), C9B(H9BA,H9BB), C7A(H7AA,H7AB), C11A(H11C,H11D),
 C7B(H7BA,H7BB), C10A(H10C,H10D), C8A(H8AA,H8AB)
3.c Aromatic/amide H refined with riding coordinates:
 N5A(H5A), C13B(H13B), N5B(H5B), C2B(H2B), C2A(H2A), C13A(H13A), C3A(H3A),
 C3B(H3B)
3.d Idealised Me refined as rotating group:
 C16A(H16D,H16E,H16F), C16B(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual space'
_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
S1B S 0.7034(16) 0.0440(10) 0.0890(9) 0.031(2) Uani 1 1 d . U . . .
S1A S 0.5080(17) 0.7304(11) 0.6646(10) 0.035(3) Uani 1 1 d . U . . .
N3B N 0.929(4) 0.284(2) 0.0701(19) 0.037(3) Uani 1 1 d . U . . .
N4A N 0.421(4) 0.792(2) 0.837(2) 0.040(3) Uani 1 1 d . U . . .
N5A N 0.721(3) 0.886(2) 0.734(2) 0.036(3) Uani 1 1 d . U . . .
H5A H 0.744770 0.927081 0.791993 0.044 Uiso 1 1 calc R . . . .
C16A C 1.012(3) 1.002(2) 0.659(2) 0.035(4) Uani 1 1 d . U . . .
H16D H 0.923163 1.093380 0.672073 0.053 Uiso 1 1 calc GR . . . .
H16E H 1.098618 1.016699 0.584136 0.053 Uiso 1 1 calc GR . . . .
H16F H 1.134090 0.957610 0.716437 0.053 Uiso 1 1 calc GR . . . .
C11B C 1.065(4) 0.179(2) 0.055(2) 0.037(3) Uani 1 1 d . U . . .
H11A H 1.142549 0.123567 0.127206 0.044 Uiso 1 1 calc R . . . .
H11B H 1.203153 0.206188 -0.002148 0.044 Uiso 1 1 calc R . . . .
O1B O 0.375(3) -0.0803(19) 0.1642(17) 0.034(4) Uani 1 1 d . U . . .
C12B C 0.931(4) 0.096(2) 0.015(2) 0.033(3) Uani 1 1 d . U . . .
C14B C 0.657(4) -0.031(2) -0.0012(19) 0.030(3) Uani 1 1 d . U . . .
C14A C 0.561(4) 0.814(2) 0.757(2) 0.038(3) Uani 1 1 d . U . . .
C13B C 0.966(4) 0.050(2) -0.077(2) 0.035(3) Uani 1 1 d . U . . .
H13B H 1.105840 0.066289 -0.134880 0.042 Uiso 1 1 calc R . . . .
F1B F 0.396(3) 0.859(2) 0.4216(18) 0.048(4) Uani 1 1 d . U . . .
C5B C 0.968(3) 0.489(2) 0.2595(19) 0.039(3) Uani 1 1 d . U . . .
H5BA H 1.020145 0.404977 0.323398 0.046 Uiso 1 1 calc R . . . .
H5BB H 1.122925 0.527156 0.225089 0.046 Uiso 1 1 calc R . . . .
C15B C 0.348(4) -0.133(2) 0.1033(19) 0.032(3) Uani 1 1 d . U . . .
F1A F 0.917(3) 0.020(2) 0.2991(19) 0.052(4) Uani 1 1 d . U . . .
C5A C 0.397(4) 0.378(2) 0.490(2) 0.044(3) Uani 1 1 d . U . . .
H5AA H 0.290383 0.447837 0.431013 0.053 Uiso 1 1 calc R . . . .
H5AB H 0.510539 0.431463 0.516165 0.053 Uiso 1 1 calc R . . . .
O1A O 0.834(3) 0.880(2) 0.5689(17) 0.037(4) Uani 1 1 d . U . . .
N2A N 0.423(3) 0.213(2) 0.3935(19) 0.045(3) Uani 1 1 d . U . . .
C4B C 0.810(4) 0.590(2) 0.300(2) 0.042(3) Uani 1 1 d . U . . .
C1A C 0.796(4) 0.104(2) 0.348(2) 0.048(3) Uani 1 1 d . U . . .
C15A C 0.835(4) 0.910(2) 0.664(2) 0.035(3) Uani 1 1 d . U . . .
N5B N 0.483(3) -0.104(2) 0.0068(18) 0.031(3) Uani 1 1 d . U . . .
H5B H 0.451378 -0.136694 -0.054885 0.037 Uiso 1 1 calc R . . . .
C2B C 0.448(4) 0.679(2) 0.344(2) 0.044(3) Uani 1 1 d . U . . .
H2B H 0.262379 0.690008 0.345243 0.053 Uiso 1 1 calc R . . . .
C2A C 0.883(4) 0.173(2) 0.397(2) 0.047(4) Uani 1 1 d . U . . .
H2A H 1.068068 0.164793 0.392933 0.057 Uiso 1 1 calc R . . . .
C13A C 0.295(4) 0.713(2) 0.833(2) 0.038(3) Uani 1 1 d . U . . .
H13A H 0.185312 0.676475 0.899012 0.045 Uiso 1 1 calc R . . . .
C12A C 0.298(3) 0.675(2) 0.747(2) 0.036(3) Uani 1 1 d . U . . .
N3A N 0.284(3) 0.478(2) 0.6751(19) 0.039(3) Uani 1 1 d . U . . .
C3A C 0.539(4) 0.133(2) 0.340(2) 0.047(4) Uani 1 1 d . U . . .
H3A H 0.454946 0.090485 0.291513 0.056 Uiso 1 1 calc R . . . .
C10B C 0.849(4) 0.395(2) -0.020(2) 0.040(3) Uani 1 1 d . U . . .
H10A H 0.999134 0.430393 -0.062191 0.048 Uiso 1 1 calc R . . . .
H10B H 0.764946 0.357178 -0.072673 0.048 Uiso 1 1 calc R . . . .
C9A C 0.561(4) 0.276(2) 0.718(2) 0.040(3) Uani 1 1 d . U . . .
H9AA H 0.644051 0.204016 0.783267 0.048 Uiso 1 1 calc R . . . .
H9AB H 0.694879 0.307010 0.659982 0.048 Uiso 1 1 calc R . . . .
N2B N 0.905(3) 0.662(2) 0.3538(18) 0.042(3) Uani 1 1 d . U . . .
N4B N 0.790(3) -0.021(2) -0.0850(18) 0.033(3) Uani 1 1 d . U . . .
C6B C 0.862(4) 0.446(2) 0.179(2) 0.037(3) Uani 1 1 d . U . . .
H6B H 0.709786 0.404902 0.215859 0.044 Uiso 1 1 calc R . . . .
C8B C 0.793(4) 0.541(2) 0.089(2) 0.037(3) Uani 1 1 d . U . . .
H8BA H 0.940094 0.586087 0.055787 0.045 Uiso 1 1 calc R . . . .
H8BB H 0.659960 0.616390 0.112839 0.045 Uiso 1 1 calc R . . . .
C9B C 0.701(4) 0.497(2) 0.006(2) 0.040(3) Uani 1 1 d . U . . .
H9BA H 0.535167 0.467507 0.033557 0.048 Uiso 1 1 calc R . . . .
H9BB H 0.672654 0.577699 -0.062082 0.048 Uiso 1 1 calc R . . . .
C7A C 0.109(4) 0.427(2) 0.638(2) 0.042(3) Uani 1 1 d . U . . .
H7AA H -0.000322 0.504344 0.584473 0.051 Uiso 1 1 calc R . . . .
H7AB H 0.000870 0.381982 0.702178 0.051 Uiso 1 1 calc R . . . .
C11A C 0.144(4) 0.599(2) 0.713(2) 0.037(3) Uani 1 1 d . U . . .
H11C H 0.040496 0.663642 0.650652 0.044 Uiso 1 1 calc R . . . .
H11D H 0.025779 0.565824 0.778314 0.044 Uiso 1 1 calc R . . . .
C7B C 1.039(3) 0.333(2) 0.1429(19) 0.037(3) Uani 1 1 d . U . . .
H7BA H 1.191813 0.370714 0.104765 0.044 Uiso 1 1 calc R . . . .
H7BB H 1.093087 0.254267 0.210096 0.044 Uiso 1 1 calc R . . . .
N1B N 0.579(3) 0.593(2) 0.3033(19) 0.042(3) Uani 1 1 d . U . . .
C1B C 0.551(4) 0.759(2) 0.385(2) 0.044(3) Uani 1 1 d . U . . .
C10A C 0.391(3) 0.213(2) 0.668(2) 0.040(3) Uani 1 1 d . U . . .
H10C H 0.272555 0.169354 0.728815 0.048 Uiso 1 1 calc R . . . .
H10D H 0.490275 0.134762 0.633341 0.048 Uiso 1 1 calc R . . . .
N1A N 0.751(4) 0.255(2) 0.4532(19) 0.046(3) Uani 1 1 d . U . . .
C8A C 0.411(4) 0.398(2) 0.756(2) 0.041(3) Uani 1 1 d . U . . .
H8AA H 0.295513 0.364818 0.821744 0.049 Uiso 1 1 calc R . . . .
H8AB H 0.523906 0.452342 0.780530 0.049 Uiso 1 1 calc R . . . .
C3B C 0.780(4) 0.750(2) 0.389(2) 0.042(3) Uani 1 1 d . U . . .
H3B H 0.850426 0.816198 0.421806 0.051 Uiso 1 1 calc R . . . .
C6A C 0.246(4) 0.323(2) 0.581(2) 0.042(3) Uani 1 1 d . U . . .
H6A H 0.121529 0.278171 0.551604 0.050 Uiso 1 1 calc R . . . .
C4A C 0.535(4) 0.277(2) 0.446(2) 0.045(3) Uani 1 1 d . U . . .
C16B C 0.191(4) -0.217(2) 0.1042(19) 0.034(4) Uani 1 1 d . U . . .
H16A H 0.281217 -0.315103 0.115363 0.050 Uiso 1 1 calc GR . . . .
H16B H 0.110199 -0.188738 0.032136 0.050 Uiso 1 1 calc GR . . . .
H16C H 0.063953 -0.208804 0.165584 0.050 Uiso 1 1 calc GR . . . .
_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
S1B C12B 1.72(3) . ?
S1B C14B 1.70(2) . ?
S1A C14A 1.80(2) . ?
S1A C12A 1.71(3) . ?
N3B C11B 1.31(3) . ?
N3B C10B 1.53(3) . ?
N3B C7B 1.50(3) . ?
N4A C14A 1.32(3) . ?
N4A C13A 1.28(3) . ?
N5A H5A 1.0300 . ?
N5A C14A 1.33(3) . ?
N5A C15A 1.12(3) . ?
C16A H16D 1.0801 . ?
C16A H16E 1.0801 . ?
C16A H16F 1.0801 . ?
C16A C15A 1.59(3) . ?
C11B H11A 1.1100 . ?
C11B H11B 1.1100 . ?
C11B C12B 1.55(3) . ?
O1B C15B 1.16(2) . ?
C12B C13B 1.44(3) . ?
C14B N5B 1.42(3) . ?
C14B N4B 1.32(3) . ?
C13B H13B 1.1000 . ?
C13B N4B 1.45(3) . ?
F1B C1B 1.43(3) . ?
C5B H5BA 1.1100 . ?
C5B H5BB 1.1100 . ?
C5B C4B 1.48(3) . ?
C5B C6B 1.53(3) . ?
C15B N5B 1.47(3) . ?
C15B C16B 1.44(3) . ?
F1A C1A 1.32(3) . ?
C5A H5AA 1.1100 . ?
C5A H5AB 1.1100 . ?
C5A C6A 1.53(3) . ?
C5A C4A 1.46(3) . ?
O1A C15A 1.41(3) . ?
N2A C3A 1.32(3) . ?
N2A C4A 1.40(3) . ?
C4B N2B 1.42(3) . ?
C4B N1B 1.38(3) . ?
C1A C2A 1.32(3) . ?
C1A C3A 1.53(3) . ?
N5B H5B 1.0300 . ?
C2B H2B 1.1000 . ?
C2B N1B 1.29(3) . ?
C2B C1B 1.42(3) . ?
C2A H2A 1.1000 . ?
C2A N1A 1.39(3) . ?
C13A H13A 1.1000 . ?
C13A C12A 1.32(3) . ?
C12A C11A 1.53(3) . ?
N3A C7A 1.48(3) . ?
N3A C11A 1.58(3) . ?
N3A C8A 1.40(3) . ?
C3A H3A 1.1000 . ?
C10B H10A 1.1100 . ?
C10B H10B 1.1100 . ?
C10B C9B 1.37(3) . ?
C9A H9AA 1.1100 . ?
C9A H9AB 1.1100 . ?
C9A C10A 1.62(2) . ?
C9A C8A 1.62(3) . ?
N2B C3B 1.26(3) . ?
C6B H6B 1.1200 . ?
C6B C8B 1.42(3) . ?
C6B C7B 1.59(3) . ?
C8B H8BA 1.1100 . ?
C8B H8BB 1.1100 . ?
C8B C9B 1.52(3) . ?
C9B H9BA 1.1100 . ?
C9B H9BB 1.1100 . ?
C7A H7AA 1.1100 . ?
C7A H7AB 1.1100 . ?
C7A C6A 1.57(3) . ?
C11A H11C 1.1100 . ?
C11A H11D 1.1100 . ?
C7B H7BA 1.1100 . ?
C7B H7BB 1.1100 . ?
C1B C3B 1.37(3) . ?
C10A H10C 1.1100 . ?
C10A H10D 1.1100 . ?
C10A C6A 1.64(3) . ?
N1A C4A 1.28(3) . ?
C8A H8AA 1.1100 . ?
C8A H8AB 1.1100 . ?
C3B H3B 1.1000 . ?
C6A H6A 1.1200 . ?
C16B H16A 1.0801 . ?
C16B H16B 1.0801 . ?
C16B H16C 1.0801 . ?
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
C14B S1B C12B 90.0(12) . . ?
C12A S1A C14A 88.0(12) . . ?
C11B N3B C10B 120(2) . . ?
C11B N3B C7B 107(2) . . ?
C7B N3B C10B 109.3(19) . . ?
C13A N4A C14A 113(2) . . ?
C14A N5A H5A 113.8 . . ?
C15A N5A H5A 113.8 . . ?
C15A N5A C14A 132(2) . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
N3B C11B H11A 109.6 . . ?
N3B C11B H11B 109.6 . . ?
N3B C11B C12B 110.2(19) . . ?
H11A C11B H11B 108.1 . . ?
C12B C11B H11A 109.6 . . ?
C12B C11B H11B 109.6 . . ?
C11B C12B S1B 118.6(17) . . ?
C13B C12B S1B 111.1(16) . . ?
C13B C12B C11B 130(2) . . ?
N5B C14B S1B 124.7(18) . . ?
N4B C14B S1B 117.8(16) . . ?
N4B C14B N5B 117.4(17) . . ?
N4A C14A S1A 109.7(16) . . ?
N4A C14A N5A 132(2) . . ?
N5A C14A S1A 119(2) . . ?
C12B C13B H13B 124.5 . . ?
C12B C13B N4B 111(2) . . ?
N4B C13B H13B 124.5 . . ?
H5BA C5B H5BB 107.9 . . ?
C4B C5B H5BA 109.2 . . ?
C4B C5B H5BB 109.2 . . ?
C4B C5B C6B 112.0(18) . . ?
C6B C5B H5BA 109.2 . . ?
C6B C5B H5BB 109.2 . . ?
O1B C15B N5B 115(2) . . ?
O1B C15B C16B 130(2) . . ?
C16B C15B N5B 114.2(19) . . ?
H5AA C5A H5AB 108.0 . . ?
C6A C5A H5AA 109.4 . . ?
C6A C5A H5AB 109.4 . . ?
C4A C5A H5AA 109.4 . . ?
C4A C5A H5AB 109.4 . . ?
C4A C5A C6A 111(2) . . ?
C3A N2A C4A 121(2) . . ?
N2B C4B C5B 116.8(18) . . ?
N1B C4B C5B 119.8(18) . . ?
N1B C4B N2B 122.0(19) . . ?
F1A C1A C2A 124(2) . . ?
F1A C1A C3A 118(2) . . ?
C2A C1A C3A 117(2) . . ?
N5A C15A C16A 121(2) . . ?
N5A C15A O1A 129(2) . . ?
O1A C15A C16A 110(2) . . ?
C14B N5B C15B 119.7(18) . . ?
C14B N5B H5B 120.1 . . ?
C15B N5B H5B 120.1 . . ?
N1B C2B H2B 121.1 . . ?
N1B C2B C1B 118(2) . . ?
C1B C2B H2B 121.1 . . ?
C1A C2A H2A 118.5 . . ?
C1A C2A N1A 123(2) . . ?
N1A C2A H2A 118.5 . . ?
N4A C13A H13A 120.4 . . ?
N4A C13A C12A 119(3) . . ?
C12A C13A H13A 120.4 . . ?
C13A C12A S1A 109.5(17) . . ?
C13A C12A C11A 131(2) . . ?
C11A C12A S1A 119.5(18) . . ?
C7A N3A C11A 103.5(17) . . ?
C8A N3A C7A 118(2) . . ?
C8A N3A C11A 108.0(19) . . ?
N2A C3A C1A 116(2) . . ?
N2A C3A H3A 121.9 . . ?
C1A C3A H3A 121.9 . . ?
N3B C10B H10A 108.6 . . ?
N3B C10B H10B 108.6 . . ?
H10A C10B H10B 107.6 . . ?
C9B C10B N3B 115(2) . . ?
C9B C10B H10A 108.6 . . ?
C9B C10B H10B 108.6 . . ?
H9AA C9A H9AB 108.5 . . ?
C10A C9A H9AA 110.2 . . ?
C10A C9A H9AB 110.2 . . ?
C8A C9A H9AA 110.2 . . ?
C8A C9A H9AB 110.2 . . ?
C8A C9A C10A 107.5(17) . . ?
C3B N2B C4B 120(2) . . ?
C14B N4B C13B 110.0(18) . . ?
C5B C6B H6B 107.9 . . ?
C5B C6B C7B 108.7(18) . . ?
C8B C6B C5B 117.0(18) . . ?
C8B C6B H6B 107.9 . . ?
C8B C6B C7B 107(2) . . ?
C7B C6B H6B 107.9 . . ?
C6B C8B H8BA 108.0 . . ?
C6B C8B H8BB 108.0 . . ?
C6B C8B C9B 117(2) . . ?
H8BA C8B H8BB 107.2 . . ?
C9B C8B H8BA 108.0 . . ?
C9B C8B H8BB 108.0 . . ?
C10B C9B C8B 111(2) . . ?
C10B C9B H9BA 109.4 . . ?
C10B C9B H9BB 109.4 . . ?
C8B C9B H9BA 109.4 . . ?
C8B C9B H9BB 109.4 . . ?
H9BA C9B H9BB 108.0 . . ?
N3A C7A H7AA 110.8 . . ?
N3A C7A H7AB 110.8 . . ?
N3A C7A C6A 104.9(17) . . ?
H7AA C7A H7AB 108.8 . . ?
C6A C7A H7AA 110.8 . . ?
C6A C7A H7AB 110.8 . . ?
C12A C11A N3A 112.0(18) . . ?
C12A C11A H11C 109.2 . . ?
C12A C11A H11D 109.2 . . ?
N3A C11A H11C 109.2 . . ?
N3A C11A H11D 109.2 . . ?
H11C C11A H11D 107.9 . . ?
N3B C7B C6B 108.7(18) . . ?
N3B C7B H7BA 109.9 . . ?
N3B C7B H7BB 109.9 . . ?
C6B C7B H7BA 109.9 . . ?
C6B C7B H7BB 109.9 . . ?
H7BA C7B H7BB 108.3 . . ?
C2B N1B C4B 117.5(19) . . ?
C2B C1B F1B 114.9(18) . . ?
C3B C1B F1B 120.0(18) . . ?
C3B C1B C2B 125(2) . . ?
C9A C10A H10C 109.6 . . ?
C9A C10A H10D 109.6 . . ?
C9A C10A C6A 110.1(17) . . ?
H10C C10A H10D 108.2 . . ?
C6A C10A H10C 109.6 . . ?
C6A C10A H10D 109.6 . . ?
C4A N1A C2A 117.5(19) . . ?
N3A C8A C9A 109.0(19) . . ?
N3A C8A H8AA 109.9 . . ?
N3A C8A H8AB 109.9 . . ?
C9A C8A H8AA 109.9 . . ?
C9A C8A H8AB 109.9 . . ?
H8AA C8A H8AB 108.3 . . ?
N2B C3B C1B 116(2) . . ?
N2B C3B H3B 121.9 . . ?
C1B C3B H3B 121.9 . . ?
C5A C6A C7A 113.5(18) . . ?
C5A C6A C10A 112.3(18) . . ?
C5A C6A H6A 108.5 . . ?
C7A C6A C10A 105.6(18) . . ?
C7A C6A H6A 108.5 . . ?
C10A C6A H6A 108.5 . . ?
N2A C4A C5A 118(2) . . ?
N1A C4A C5A 118.1(19) . . ?
N1A C4A N2A 124(2) . . ?
C15B C16B H16A 109.5 . . ?
C15B C16B H16B 109.5 . . ?
C15B C16B H16C 109.5 . . ?
H16A C16B H16B 109.5 . . ?
H16A C16B H16C 109.5 . . ?
H16B C16B H16C 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
S1B C12B C13B N4B 3(3) . . . . ?
S1B C14B N5B C15B -8(3) . . . . ?
S1B C14B N4B C13B 4(3) . . . . ?
S1A C12A C11A N3A 55(3) . . . . ?
N3B C11B C12B S1B -58(3) . . . . ?
N3B C11B C12B C13B 122(3) . . . . ?
N3B C10B C9B C8B 51(3) . . . . ?
N4A C13A C12A S1A 7(3) . . . . ?
N4A C13A C12A C11A -169(2) . . . . ?
C11B N3B C10B C9B 178(2) . . . . ?
C11B N3B C7B C6B -170(2) . . . . ?
C11B C12B C13B N4B -177(2) . . . . ?
O1B C15B N5B C14B 9(3) . . . . ?
C12B S1B C14B N5B 179(2) . . . . ?
C12B S1B C14B N4B -2(2) . . . . ?
C12B C13B N4B C14B -4(3) . . . . ?
C14B S1B C12B C11B 179(2) . . . . ?
C14B S1B C12B C13B -1(2) . . . . ?
C14A S1A C12A C13A -4(2) . . . . ?
C14A S1A C12A C11A 173(2) . . . . ?
C14A N4A C13A C12A -7(4) . . . . ?
C14A N5A C15A C16A 179(2) . . . . ?
C14A N5A C15A O1A 6(6) . . . . ?
F1B C1B C3B N2B -178(3) . . . . ?
C5B C4B N2B C3B 179(3) . . . . ?
C5B C4B N1B C2B 177(3) . . . . ?
C5B C6B C8B C9B 176.2(18) . . . . ?
C5B C6B C7B N3B 176(2) . . . . ?
F1A C1A C2A N1A -176(3) . . . . ?
F1A C1A C3A N2A 177(3) . . . . ?
C4B C5B C6B C8B 61(3) . . . . ?
C4B C5B C6B C7B -178(2) . . . . ?
C4B N2B C3B C1B 9(4) . . . . ?
C1A C2A N1A C4A -9(4) . . . . ?
C15A N5A C14A S1A 2(5) . . . . ?
C15A N5A C14A N4A -176(4) . . . . ?
N5B C14B N4B C13B -176.6(19) . . . . ?
C2B C1B C3B N2B -1(4) . . . . ?
C2A C1A C3A N2A -9(4) . . . . ?
C2A N1A C4A C5A -170(3) . . . . ?
C2A N1A C4A N2A 7(4) . . . . ?
C13A N4A C14A S1A 4(3) . . . . ?
C13A N4A C14A N5A -178(3) . . . . ?
C13A C12A C11A N3A -128(3) . . . . ?
C12A S1A C14A N4A 0(2) . . . . ?
C12A S1A C14A N5A -179(2) . . . . ?
N3A C7A C6A C5A -61(3) . . . . ?
N3A C7A C6A C10A 63(2) . . . . ?
C3A N2A C4A C5A 170(3) . . . . ?
C3A N2A C4A N1A -7(4) . . . . ?
C3A C1A C2A N1A 10(4) . . . . ?
C10B N3B C11B C12B -75(3) . . . . ?
C10B N3B C7B C6B 58(2) . . . . ?
C9A C10A C6A C5A 64(2) . . . . ?
C9A C10A C6A C7A -60(2) . . . . ?
N2B C4B N1B C2B 11(4) . . . . ?
N4B C14B N5B C15B 172(3) . . . . ?
C6B C5B C4B N2B -164(2) . . . . ?
C6B C5B C4B N1B 29(3) . . . . ?
C6B C8B C9B C10B -53(3) . . . . ?
C8B C6B C7B N3B -57(2) . . . . ?
C7A N3A C11A C12A -175(2) . . . . ?
C7A N3A C8A C9A 65(2) . . . . ?
C11A N3A C7A C6A 170(2) . . . . ?
C11A N3A C8A C9A -178.6(16) . . . . ?
C7B N3B C11B C12B 159(2) . . . . ?
C7B N3B C10B C9B -57(3) . . . . ?
C7B C6B C8B C9B 54(3) . . . . ?
N1B C4B N2B C3B -14(4) . . . . ?
N1B C2B C1B F1B 175(3) . . . . ?
N1B C2B C1B C3B -2(4) . . . . ?
C1B C2B N1B C4B -3(4) . . . . ?
C10A C9A C8A N3A -52(2) . . . . ?
C8A N3A C7A C6A -71(3) . . . . ?
C8A N3A C11A C12A 59(3) . . . . ?
C8A C9A C10A C6A 53(2) . . . . ?
C6A C5A C4A N2A 69(3) . . . . ?
C6A C5A C4A N1A -113(3) . . . . ?
C4A C5A C6A C7A 175(2) . . . . ?
C4A C5A C6A C10A 55(2) . . . . ?
C4A N2A C3A C1A 7(4) . . . . ?
C16B C15B N5B C14B -175(2) . . . . ?
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT020_540p2s3_p1_x-final  
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.256 Report
RESPONSE: These data were collected with electron diffraction.
Dynamical scattering and aberrations in the electron optics could
be sources of these errors.
;
_vrf_PLAT029_540p2s3_p1_x-final  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.928 Why?  
RESPONSE: These data were collected using a transmission electron
microscope with a goniometer that can only rotate -70 to +70. This
leads to incomplete data from individual crystals, depending on the 
orientation of the crystal and the crystallographic symmetry. To 
ameliorate this, data from nine individual crystals were combined. 
Unfortunately, in this case the completeness was still a little low
(96% in the low resolution shell and 93% overall), likely due to 
preferred orientation of the crystals on the grid surface. 
;
_vrf_PLAT050_540p2s3_p1_x-final  
;
PROBLEM: Absorption Coefficient mu Not Given ............     Please Do !  
RESPONSE: There is currently no literature describing the absorption
coefficient mu for electron diffraction.
;
_vrf_PLAT316_540p2s3_p1_x-final  
;
PROBLEM: Too many H on C in C=N Moiety in Main Residue ..       C11B Check 
RESPONSE: The bond between C11B and N3B should be a single bond, so the 
number of hydrogen atoms is appropriate. The geometry of N3B is 
tetragonal and therefore this nitrogen cannot form a double bond with 
C11B. Additionally, the second copy of the molecule in the asymmetric 
unit clearly contains a single bond for the corresponding C and N 
atoms. We suspect that slight inaccuracies in unit cell measurements 
are causing this bond to appear shorter than expected. We restrained 
the detector distance during cell refinement, as must be done for 
electron diffraction, and suspect that this has led to less
accurate cell parameters, which will affect bond lengths.
;
# end Validation Reply Form





####################################################################### 
# 
# 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_540p4s1_p21_t3_102ax
_database_code_depnum_ccdc_archive 'CCDC 2132512'
loop_
_audit_author_name
_audit_author_address
'Jessica Bruhn'
;NanoImaging Services
United States of America
;
_audit_update_record             
;
2022-02-26 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_540p4s1_p21_t3_102ax 
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: These data were collected with electron diffraction. Dynamical scattering and aberrations in the electron optics could be sources of these errors.
;
_vrf_THETM01_540p4s1_p21_t3_102ax 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The resolution was limited by the quality of the crystals. These data were collected by electron diffraction from crystals several orders of magnitude smaller than those typically used for X-ray diffraction. Data was recorded to 0.66 Ang. and subsequently truncated to the resolution limit of the crystals.
;
_vrf_PLAT020_540p4s1_p21_t3_102ax 
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.281 Report
RESPONSE: These data were collected with electron diffraction. Dynamical scattering and aberrations in the electron optics could be sources of these errors.
;
_vrf_PLAT340_540p4s1_p21_t3_102ax 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0368 Ang.
RESPONSE: The resolution of these crystals was low (1.02 Ang), likely leading to lower bond precision. Many restraints were added to  idealize the structure.
;
# Added during the CSD deposition process: Saturday 26 February 2022 02:05 AM
# end Validation Reply Form


_audit_creation_date             2022-02-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'C16H21FN5OS D-malate'
_chemical_name_systematic        
'(3R)-1-[(2-acetamido-1,3-thiazol-5-yl)methyl]-3-[(5-fluoropyrimidin-2-yl)methyl]piperidin-1-ium (2R)-3-carboxy-2-hydroxypropanoate'
_chemical_formula_moiety         
'0.5(C4 H5 O5), C16 H21 F N5 O S, 0.5[D-malate]'
_chemical_formula_sum            'C18 H23.50 F N5 O3.50 S'
_chemical_formula_weight         416.97
_chemical_absolute_configuration rm
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 'International Tables Vol C Tables 4.3.1.1 and 4.3.2.2'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.3.1.1 and 4.3.2.2'
F F 0.0000 0.0000 'International Tables Vol C Tables 4.3.1.1 and 4.3.2.2'
N N 0.0000 0.0000 'International Tables Vol C Tables 4.3.1.1 and 4.3.2.2'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.3.1.1 and 4.3.2.2'
S S 0.0000 0.0000 'International Tables Vol C Tables 4.3.1.1 and 4.3.2.2'
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a                   9.2423(19)
_cell_length_b                   6.0071(12)
_cell_length_c                   40.582(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.35(3)
_cell_angle_gamma                90
_cell_volume                     2246.6(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4988
_cell_measurement_temperature    80.15
_cell_measurement_theta_max      0.92
_cell_measurement_theta_min      0.04
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   'electron diffraction, unknown absorption'
_exptl_absorpt_special_details   dials.scale
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       planks
_exptl_crystal_F_000             330
_exptl_crystal_size_max          0.0012
_exptl_crystal_size_mid          0.0006
_exptl_crystal_size_min          0.0001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2812
_diffrn_detector                 CMOS
_diffrn_detector_type            'Thermo Fisher CETA-D'
_diffrn_measurement_device       'transmission electron microscope'
_diffrn_radiation_probe          electron
_diffrn_source_type              'Thermo Fisher Glacios at 200keV'
_diffrn_source_voltage           200
_exptl_absorpt_correction_T_min  0.99996
_exptl_absorpt_correction_T_max  1
_diffrn_reflns_av_unetI/netI     0.4945
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            22340
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        0.702
_diffrn_reflns_theta_max         0.702
_diffrn_reflns_theta_min         0.018
_diffrn_ambient_temperature      80.15
_diffrn_detector_area_resol_mean 35.7
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Thermo Fisher Glacios at 200keV'
_diffrn_measurement_method       'w/ scans'
_diffrn_radiation_type           electron
_diffrn_radiation_wavelength     0.02501
_diffrn_source                   'transmission electron microscope'
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                1031
_reflns_number_total             4190
_reflns_special_details          
;
This structure was determined by electron diffraction for 
the purpose of absolute configuration determination via
an internal chiral probe. The resolution was fairly low 
(1.02A), and therefore the structure needed to be 
highly restrained. A disordered solvent molecule was 
accounted for with a solvent mask.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'dials.cosym (Gildea, et al., 2018)'
_computing_data_collection       'Leginon (Cheng et al., 2021)'
_computing_data_reduction        'DIALS (Clabbers et al., 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD (Schneider, 2002)'
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         4190
_refine_ls_number_restraints     375
_refine_ls_R_factor_all          0.2292
_refine_ls_R_factor_gt           0.1215
_refine_ls_restrained_S_all      0.800
_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)+(0.1339P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2803
_refine_ls_wR_factor_ref         0.3056
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C2D-C3D
 1.54 with sigma of 0.01
 C2D-C1D = C4D-C3D = C6A-C10A = C5A-C6A = C9A-C10A = C6B-C10B
 1.54 with sigma of 0.02
 H5D-O2D_$1
 1.6 with sigma of 0.02
 C12A-C13A = C11A-C12A = C15B-C16B
 1.47 with sigma of 0.02
 O5D-C4D
 1.43 with sigma of 0.01
 H5D-H3DA
 1.9 with sigma of 0.02
 C2D-O3D
 1.43 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.005 within 2A
4.a Ternary CH refined with riding coordinates:
 C2D(H2D), N3B(H3B), C6B(H6B), N3A(H3AA), C6A(H6A)
4.b Secondary CH2 refined with riding coordinates:
 C3D(H3DA,H3DB), C5B(H5BA,H5BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB), C9B(H9BA,
 H9BB), C10B(H10A,H10B), C11B(H11A,H11B), C5A(H5AA,H5AB), C7A(H7AA,H7AB),
 C8A(H8AA,H8AB), C9A(H9AA,H9AB), C10A(H10C,H10D), C11A(H11C,H11D)
4.c Aromatic/amide H refined with riding coordinates:
 N5B(H5B), C3B(H3BA), C2B(H2B), C13B(H13B), C2A(H2A), C3A(H3A), N5A(H5A),
 C13A(H13A)
4.d Fitted hexagon refined as free rotating group:
 C3B(N2B,C4B,N1B,C2B,C1B), N2A(C4A,N1A,C2A,C1A,C3A)
4.e Idealised Me refined as rotating group:
 C16B(H16A,H16B,H16C), C16A(H16D,H16E,H16F)
4.f Idealised tetrahedral OH refined as rotating group:
 O3D(H3D), O5D(H5D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'dual space'
_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
O1D O 0.500(3) 0.702(4) 0.8879(11) 0.117(7) Uani 1 1 d . U . . .
O2D O 0.617(2) 0.477(4) 0.8537(11) 0.120(7) Uani 1 1 d . U . . .
O3D O 0.745(3) 0.896(4) 0.9058(9) 0.116(7) Uani 1 1 d D U . . .
H3D H 0.659013 0.991067 0.904777 0.175 Uiso 1 1 calc R U . . .
O4D O 1.014(3) 0.998(4) 0.8579(10) 0.112(7) Uani 1 1 d . U . . .
O5D O 0.858(2) 1.301(3) 0.8430(9) 0.119(7) Uani 1 1 d D U . . .
H5D H 0.763786 1.328132 0.851995 0.178 Uiso 1 1 calc DR U . . .
C1D C 0.606(3) 0.646(5) 0.8706(11) 0.120(7) Uani 1 1 d D U . . .
C2D C 0.753(3) 0.782(5) 0.8743(8) 0.118(7) Uani 1 1 d D U . . .
H2D H 0.848074 0.671332 0.874493 0.142 Uiso 1 1 calc R U . . .
C3D C 0.747(2) 0.947(4) 0.8440(8) 0.120(7) Uani 1 1 d D U . . .
H3DA H 0.656595 1.062763 0.844775 0.144 Uiso 1 1 calc DR U . . .
H3DB H 0.736434 0.856235 0.820612 0.144 Uiso 1 1 calc R U . . .
C4D C 0.899(3) 1.073(3) 0.8488(10) 0.117(7) Uani 1 1 d D U . . .
S1B S 0.5947(12) 0.1222(18) 0.6967(4) 0.071(4) Uani 1 1 d . U . . .
F1B F -0.029(2) 1.047(4) 0.5324(9) 0.102(6) Uani 1 1 d . U . . .
O1B O 0.518(2) -0.237(4) 0.7234(9) 0.072(6) Uani 1 1 d . U . . .
N3B N 0.627(3) 0.393(4) 0.6244(9) 0.083(4) Uani 1 1 d . U . . .
H3B H 0.544909 0.275464 0.623040 0.100 Uiso 1 1 calc R U . . .
N4B N 0.866(2) 0.172(4) 0.7258(8) 0.070(5) Uani 1 1 d . U . . .
N5B N 0.744(2) -0.127(4) 0.7456(8) 0.074(5) Uani 1 1 d . U . . .
H5B H 0.827589 -0.147486 0.762739 0.089 Uiso 1 1 calc R U . . .
C3B C 0.1183(15) 0.733(3) 0.5404(6) 0.103(5) Uani 1 1 d G U . . .
H3BA H 0.025536 0.626715 0.543010 0.123 Uiso 1 1 calc R U . . .
N2B N 0.2572(19) 0.643(2) 0.5424(7) 0.101(5) Uani 1 1 d G U . . .
C4B C 0.3765(13) 0.779(3) 0.5391(7) 0.103(5) Uani 1 1 d G U . . .
N1B N 0.3569(15) 1.006(3) 0.5336(6) 0.106(5) Uani 1 1 d G U . . .
C2B C 0.2180(19) 1.096(2) 0.5316(6) 0.105(5) Uani 1 1 d G U . . .
H2B H 0.202860 1.272678 0.527381 0.127 Uiso 1 1 calc R U . . .
C1B C 0.0987(13) 0.960(3) 0.5350(6) 0.103(5) Uani 1 1 d G U . . .
C5B C 0.516(2) 0.648(4) 0.5372(9) 0.097(5) Uani 1 1 d . U . . .
H5BA H 0.606022 0.763873 0.539073 0.116 Uiso 1 1 calc R U . . .
H5BB H 0.514683 0.571126 0.513109 0.116 Uiso 1 1 calc R U . . .
C6B C 0.546(2) 0.468(4) 0.5632(9) 0.092(4) Uani 1 1 d D U . . .
H6B H 0.455465 0.349340 0.563854 0.110 Uiso 1 1 calc R U . . .
C7B C 0.578(3) 0.599(4) 0.5984(9) 0.089(5) Uani 1 1 d . U . . .
H7BA H 0.481056 0.683410 0.605703 0.107 Uiso 1 1 calc R U . . .
H7BB H 0.665153 0.720205 0.597074 0.107 Uiso 1 1 calc R U . . .
C8B C 0.758(2) 0.284(4) 0.6206(8) 0.083(5) Uani 1 1 d . U . . .
H8BA H 0.778139 0.154908 0.639264 0.099 Uiso 1 1 calc R U . . .
H8BB H 0.848627 0.400954 0.622353 0.099 Uiso 1 1 calc R U . . .
C9B C 0.739(3) 0.183(4) 0.5862(9) 0.084(5) Uani 1 1 d . U . . .
H9BA H 0.839764 0.102193 0.580733 0.101 Uiso 1 1 calc R U . . .
H9BB H 0.655259 0.054445 0.586154 0.101 Uiso 1 1 calc R U . . .
C10B C 0.698(2) 0.345(4) 0.5597(9) 0.088(5) Uani 1 1 d D U . . .
H10A H 0.692532 0.258237 0.536075 0.105 Uiso 1 1 calc R U . . .
H10B H 0.782586 0.470261 0.559418 0.105 Uiso 1 1 calc R U . . .
C11B C 0.625(2) 0.524(4) 0.6606(8) 0.080(4) Uani 1 1 d . U . . .
H11A H 0.682527 0.682205 0.660334 0.096 Uiso 1 1 calc R U . . .
H11B H 0.514949 0.551886 0.667391 0.096 Uiso 1 1 calc R U . . .
C12B C 0.705(3) 0.358(4) 0.6838(9) 0.073(4) Uani 1 1 d . U . . .
C13B C 0.835(3) 0.343(4) 0.7043(8) 0.070(5) Uani 1 1 d . U . . .
H13B H 0.914097 0.474266 0.702834 0.085 Uiso 1 1 calc R U . . .
C14B C 0.739(3) 0.040(4) 0.7241(9) 0.071(4) Uani 1 1 d . U . . .
C15B C 0.625(3) -0.272(4) 0.7431(8) 0.073(5) Uani 1 1 d D U . . .
C16B C 0.644(2) -0.450(4) 0.7671(7) 0.074(6) Uani 1 1 d D U . . .
H16A H 0.755780 -0.483247 0.772009 0.111 Uiso 1 1 calc R U . . .
H16B H 0.590264 -0.594686 0.757541 0.111 Uiso 1 1 calc R U . . .
H16C H 0.598578 -0.401165 0.789237 0.111 Uiso 1 1 calc R U . . .
S1A S 0.3021(11) 0.7633(18) 0.8038(4) 0.059(4) Uani 1 1 d . U . . .
F1A F 0.249(3) 0.911(5) 1.0671(10) 0.097(6) Uani 1 1 d . U . . .
O1A O 0.389(2) 1.115(4) 0.7676(8) 0.067(5) Uani 1 1 d . U . . .
N2A N 0.0931(16) 0.611(3) 0.9949(7) 0.095(5) Uani 1 1 d G U . . .
C4A C 0.152(2) 0.748(4) 0.9719(5) 0.093(5) Uani 1 1 d G U . . .
N1A N 0.241(2) 0.925(3) 0.9824(6) 0.095(5) Uani 1 1 d G U . . .
C2A C 0.2711(15) 0.964(3) 1.0159(7) 0.095(6) Uani 1 1 d G U . . .
H2A H 0.340196 1.101782 1.024121 0.113 Uiso 1 1 calc R U . . .
C1A C 0.212(2) 0.827(4) 1.0390(5) 0.096(5) Uani 1 1 d G U . . .
C3A C 0.1230(19) 0.650(3) 1.0285(6) 0.097(6) Uani 1 1 d G U . . .
H3A H 0.077111 0.543700 1.046410 0.116 Uiso 1 1 calc R U . . .
N3A N 0.292(2) 0.379(4) 0.8716(9) 0.072(4) Uani 1 1 d . U . . .
H3AA H 0.377490 0.489671 0.872278 0.086 Uiso 1 1 calc R U . . .
N4A N 0.035(2) 0.747(4) 0.7810(8) 0.064(4) Uani 1 1 d . U . . .
N5A N 0.156(3) 1.043(4) 0.7593(8) 0.065(4) Uani 1 1 d . U . . .
H5A H 0.064171 1.086992 0.745875 0.078 Uiso 1 1 calc R U . . .
C5A C 0.101(2) 0.674(4) 0.9383(8) 0.086(5) Uani 1 1 d D U . . .
H5AA H 0.061451 0.816308 0.923658 0.104 Uiso 1 1 calc R U . . .
H5AB H 0.012158 0.556396 0.939759 0.104 Uiso 1 1 calc R U . . .
C6A C 0.230(3) 0.559(4) 0.9211(8) 0.079(4) Uani 1 1 d D U . . .
H6A H 0.320172 0.678638 0.921071 0.095 Uiso 1 1 calc R U . . .
C7A C 0.178(2) 0.511(4) 0.8852(8) 0.075(5) Uani 1 1 d . U . . .
H7AA H 0.075755 0.418614 0.883938 0.089 Uiso 1 1 calc R U . . .
H7AB H 0.160552 0.665980 0.871458 0.089 Uiso 1 1 calc R U . . .
C8A C 0.352(3) 0.197(4) 0.8910(9) 0.073(5) Uani 1 1 d . U . . .
H8AA H 0.435490 0.124672 0.877152 0.088 Uiso 1 1 calc R U . . .
H8AB H 0.266971 0.073239 0.891474 0.088 Uiso 1 1 calc R U . . .
C9A C 0.415(2) 0.222(4) 0.9255(8) 0.075(5) Uani 1 1 d D U . . .
H9AA H 0.513180 0.322448 0.926742 0.090 Uiso 1 1 calc R U . . .
H9AB H 0.439025 0.060475 0.936962 0.090 Uiso 1 1 calc R U . . .
C10A C 0.288(2) 0.344(4) 0.9422(7) 0.079(5) Uani 1 1 d D U . . .
H10C H 0.326199 0.396981 0.967070 0.095 Uiso 1 1 calc R U . . .
H10D H 0.198094 0.228505 0.944380 0.095 Uiso 1 1 calc R U . . .
C11A C 0.249(3) 0.359(4) 0.8343(8) 0.066(4) Uani 1 1 d D U . . .
H11C H 0.341264 0.290752 0.822639 0.079 Uiso 1 1 calc R U . . .
H11D H 0.161397 0.237109 0.831130 0.079 Uiso 1 1 calc R U . . .
C12A C 0.202(2) 0.556(4) 0.8163(7) 0.063(4) Uani 1 1 d D U . . .
C13A C 0.047(2) 0.571(4) 0.8028(7) 0.065(4) Uani 1 1 d D U . . .
H13A H -0.039519 0.462675 0.809050 0.079 Uiso 1 1 calc R U . . .
C14A C 0.148(3) 0.869(4) 0.7797(8) 0.063(4) Uani 1 1 d . U . . .
C15A C 0.270(3) 1.158(4) 0.7552(8) 0.067(5) Uani 1 1 d . U . . .
C16A C 0.253(2) 1.359(4) 0.7311(7) 0.068(5) Uani 1 1 d . U . . .
H16D H 0.317239 1.331019 0.710835 0.103 Uiso 1 1 calc R U . . .
H16E H 0.289187 1.505906 0.743651 0.103 Uiso 1 1 calc R U . . .
H16F H 0.143106 1.376710 0.722329 0.103 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
O1D C1D 1.29(4) . ?
O2D C1D 1.23(4) . ?
O3D H3D 0.9801 . ?
O3D C2D 1.46(2) . ?
O4D C4D 1.18(3) . ?
O5D H5D 0.9801 . ?
O5D C4D 1.437(14) . ?
C1D C2D 1.58(2) . ?
C2D H2D 1.1000 . ?
C2D C3D 1.575(14) . ?
C3D H3DA 1.0900 . ?
C3D H3DB 1.0900 . ?
C3D C4D 1.60(2) . ?
S1B C12B 1.84(3) . ?
S1B C14B 1.74(3) . ?
F1B C1B 1.29(2) . ?
O1B C15B 1.24(3) . ?
N3B H3B 1.0330 . ?
N3B C7B 1.66(4) . ?
N3B C8B 1.40(3) . ?
N3B C11B 1.67(4) . ?
N4B C13B 1.37(4) . ?
N4B C14B 1.41(3) . ?
N5B H5B 1.0100 . ?
N5B C14B 1.33(3) . ?
N5B C15B 1.40(3) . ?
C3B H3BA 1.0800 . ?
C3B N2B 1.3900 . ?
C3B C1B 1.3900 . ?
N2B C4B 1.3900 . ?
C4B N1B 1.3900 . ?
C4B C5B 1.52(2) . ?
N1B C2B 1.3900 . ?
C2B H2B 1.0800 . ?
C2B C1B 1.3900 . ?
C5B H5BA 1.0800 . ?
C5B H5BB 1.0800 . ?
C5B C6B 1.52(4) . ?
C6B H6B 1.1000 . ?
C6B C7B 1.64(4) . ?
C6B C10B 1.60(2) . ?
C7B H7BA 1.0900 . ?
C7B H7BB 1.0900 . ?
C8B H8BA 1.0900 . ?
C8B H8BB 1.0900 . ?
C8B C9B 1.52(4) . ?
C9B H9BA 1.0900 . ?
C9B H9BB 1.0900 . ?
C9B C10B 1.48(4) . ?
C10B H10A 1.0900 . ?
C10B H10B 1.0900 . ?
C11B H11A 1.0900 . ?
C11B H11B 1.0900 . ?
C11B C12B 1.52(3) . ?
C12B C13B 1.41(3) . ?
C13B H13B 1.0800 . ?
C15B C16B 1.45(2) . ?
C16B H16A 1.0601 . ?
C16B H16B 1.0601 . ?
C16B H16C 1.0601 . ?
S1A C12A 1.65(2) . ?
S1A C14A 1.78(3) . ?
F1A C1A 1.27(4) . ?
O1A C15A 1.20(3) . ?
N2A C4A 1.3900 . ?
N2A C3A 1.3901 . ?
C4A N1A 1.3900 . ?
C4A C5A 1.47(3) . ?
N1A C2A 1.3900 . ?
C2A H2A 1.0800 . ?
C2A C1A 1.3900 . ?
C1A C3A 1.3900 . ?
C3A H3A 1.0800 . ?
N3A H3AA 1.0330 . ?
N3A C7A 1.46(3) . ?
N3A C8A 1.43(3) . ?
N3A C11A 1.54(4) . ?
N4A C13A 1.37(3) . ?
N4A C14A 1.29(3) . ?
N5A H5A 1.0100 . ?
N5A C14A 1.34(3) . ?
N5A C15A 1.28(3) . ?
C5A H5AA 1.0900 . ?
C5A H5AB 1.0900 . ?
C5A C6A 1.59(2) . ?
C6A H6A 1.1000 . ?
C6A C7A 1.53(3) . ?
C6A C10A 1.61(2) . ?
C7A H7AA 1.0900 . ?
C7A H7AB 1.0900 . ?
C8A H8AA 1.0800 . ?
C8A H8AB 1.0800 . ?
C8A C9A 1.49(4) . ?
C9A H9AA 1.0900 . ?
C9A H9AB 1.0900 . ?
C9A C10A 1.58(2) . ?
C10A H10C 1.0900 . ?
C10A H10D 1.0900 . ?
C11A H11C 1.0900 . ?
C11A H11D 1.0900 . ?
C11A C12A 1.44(2) . ?
C12A C13A 1.49(2) . ?
C13A H13A 1.0800 . ?
C15A C16A 1.55(3) . ?
C16A H16D 1.0601 . ?
C16A H16E 1.0601 . ?
C16A H16F 1.0601 . ?
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
C2D O3D H3D 109.5 . . ?
C4D O5D H5D 109.5 . . ?
O1D C1D C2D 120(3) . . ?
O2D C1D O1D 128(3) . . ?
O2D C1D C2D 112(3) . . ?
O3D C2D C1D 103(3) . . ?
O3D C2D H2D 111.6 . . ?
O3D C2D C3D 113(3) . . ?
C1D C2D H2D 111.6 . . ?
C3D C2D C1D 106(2) . . ?
C3D C2D H2D 111.6 . . ?
C2D C3D H3DA 111.2 . . ?
C2D C3D H3DB 111.2 . . ?
C2D C3D C4D 103(2) . . ?
H3DA C3D H3DB 109.1 . . ?
C4D C3D H3DA 111.2 . . ?
C4D C3D H3DB 111.2 . . ?
O4D C4D O5D 130(3) . . ?
O4D C4D C3D 128(2) . . ?
O5D C4D C3D 102(2) . . ?
C14B S1B C12B 89.2(14) . . ?
C7B N3B H3B 108.2 . . ?
C7B N3B C11B 100.9(19) . . ?
C8B N3B H3B 108.2 . . ?
C8B N3B C7B 118(3) . . ?
C8B N3B C11B 112(3) . . ?
C11B N3B H3B 108.2 . . ?
C13B N4B C14B 105(3) . . ?
C14B N5B H5B 122.1 . . ?
C14B N5B C15B 116(3) . . ?
C15B N5B H5B 122.1 . . ?
N2B C3B H3BA 120.0 . . ?
N2B C3B C1B 120.0 . . ?
C1B C3B H3BA 120.0 . . ?
C3B N2B C4B 120.0 . . ?
N2B C4B N1B 120.0 . . ?
N2B C4B C5B 112.5(15) . . ?
N1B C4B C5B 127.0(16) . . ?
C2B N1B C4B 120.0 . . ?
N1B C2B H2B 120.0 . . ?
N1B C2B C1B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
F1B C1B C3B 121.4(17) . . ?
F1B C1B C2B 118.6(18) . . ?
C2B C1B C3B 120.0 . . ?
C4B C5B H5BA 108.2 . . ?
C4B C5B H5BB 108.2 . . ?
C4B C5B C6B 116(2) . . ?
H5BA C5B H5BB 107.4 . . ?
C6B C5B H5BA 108.2 . . ?
C6B C5B H5BB 108.2 . . ?
C5B C6B H6B 112.2 . . ?
C5B C6B C7B 106(2) . . ?
C5B C6B C10B 112(2) . . ?
C7B C6B H6B 112.2 . . ?
C10B C6B H6B 112.2 . . ?
C10B C6B C7B 101(2) . . ?
N3B C7B H7BA 111.3 . . ?
N3B C7B H7BB 111.3 . . ?
C6B C7B N3B 102(2) . . ?
C6B C7B H7BA 111.3 . . ?
C6B C7B H7BB 111.3 . . ?
H7BA C7B H7BB 109.2 . . ?
N3B C8B H8BA 110.9 . . ?
N3B C8B H8BB 110.9 . . ?
N3B C8B C9B 104(3) . . ?
H8BA C8B H8BB 108.9 . . ?
C9B C8B H8BA 110.9 . . ?
C9B C8B H8BB 110.9 . . ?
C8B C9B H9BA 108.7 . . ?
C8B C9B H9BB 108.7 . . ?
H9BA C9B H9BB 107.6 . . ?
C10B C9B C8B 114(2) . . ?
C10B C9B H9BA 108.7 . . ?
C10B C9B H9BB 108.7 . . ?
C6B C10B H10A 108.6 . . ?
C6B C10B H10B 108.6 . . ?
C9B C10B C6B 115(3) . . ?
C9B C10B H10A 108.6 . . ?
C9B C10B H10B 108.6 . . ?
H10A C10B H10B 107.6 . . ?
N3B C11B H11A 111.4 . . ?
N3B C11B H11B 111.4 . . ?
H11A C11B H11B 109.3 . . ?
C12B C11B N3B 102(2) . . ?
C12B C11B H11A 111.4 . . ?
C12B C11B H11B 111.4 . . ?
C11B C12B S1B 115.1(19) . . ?
C13B C12B S1B 104(2) . . ?
C13B C12B C11B 139(2) . . ?
N4B C13B C12B 124(3) . . ?
N4B C13B H13B 118.2 . . ?
C12B C13B H13B 118.2 . . ?
N4B C14B S1B 118(2) . . ?
N5B C14B S1B 128(2) . . ?
N5B C14B N4B 114(3) . . ?
O1B C15B N5B 122(3) . . ?
O1B C15B C16B 127(3) . . ?
N5B C15B C16B 111(3) . . ?
C15B C16B H16A 109.5 . . ?
C15B C16B H16B 109.5 . . ?
C15B C16B H16C 109.5 . . ?
H16A C16B H16B 109.5 . . ?
H16A C16B H16C 109.5 . . ?
H16B C16B H16C 109.5 . . ?
C12A S1A C14A 89.6(13) . . ?
C4A N2A C3A 120.00(6) . . ?
N2A C4A C5A 109(2) . . ?
N1A C4A N2A 120.0 . . ?
N1A C4A C5A 131(2) . . ?
C2A N1A C4A 120.00(6) . . ?
N1A C2A H2A 120.0 . . ?
C1A C2A N1A 120.00(7) . . ?
C1A C2A H2A 120.0 . . ?
F1A C1A C2A 106(2) . . ?
F1A C1A C3A 134(2) . . ?
C2A C1A C3A 120.0 . . ?
N2A C3A H3A 120.0 . . ?
C1A C3A N2A 120.0 . . ?
C1A C3A H3A 120.0 . . ?
C7A N3A H3AA 102.4 . . ?
C7A N3A C11A 106(2) . . ?
C8A N3A H3AA 102.4 . . ?
C8A N3A C7A 118(3) . . ?
C8A N3A C11A 123(3) . . ?
C11A N3A H3AA 102.4 . . ?
C14A N4A C13A 116(3) . . ?
C14A N5A H5A 117.0 . . ?
C15A N5A H5A 117.0 . . ?
C15A N5A C14A 126(3) . . ?
C4A C5A H5AA 109.7 . . ?
C4A C5A H5AB 109.7 . . ?
C4A C5A C6A 110(2) . . ?
H5AA C5A H5AB 108.2 . . ?
C6A C5A H5AA 109.7 . . ?
C6A C5A H5AB 109.7 . . ?
C5A C6A H6A 107.9 . . ?
C5A C6A C10A 110(2) . . ?
C7A C6A C5A 108(2) . . ?
C7A C6A H6A 107.9 . . ?
C7A C6A C10A 115(2) . . ?
C10A C6A H6A 107.9 . . ?
N3A C7A C6A 106(2) . . ?
N3A C7A H7AA 110.6 . . ?
N3A C7A H7AB 110.6 . . ?
C6A C7A H7AA 110.6 . . ?
C6A C7A H7AB 110.6 . . ?
H7AA C7A H7AB 108.7 . . ?
N3A C8A H8AA 106.5 . . ?
N3A C8A H8AB 106.5 . . ?
N3A C8A C9A 123(3) . . ?
H8AA C8A H8AB 106.5 . . ?
C9A C8A H8AA 106.5 . . ?
C9A C8A H8AB 106.5 . . ?
C8A C9A H9AA 111.5 . . ?
C8A C9A H9AB 111.5 . . ?
C8A C9A C10A 102(2) . . ?
H9AA C9A H9AB 109.3 . . ?
C10A C9A H9AA 111.5 . . ?
C10A C9A H9AB 111.5 . . ?
C6A C10A H10C 109.3 . . ?
C6A C10A H10D 109.3 . . ?
C9A C10A C6A 112(2) . . ?
C9A C10A H10C 109.3 . . ?
C9A C10A H10D 109.3 . . ?
H10C C10A H10D 108.0 . . ?
N3A C11A H11C 107.6 . . ?
N3A C11A H11D 107.6 . . ?
H11C C11A H11D 107.1 . . ?
C12A C11A N3A 119(3) . . ?
C12A C11A H11C 107.6 . . ?
C12A C11A H11D 107.6 . . ?
C11A C12A S1A 128.4(19) . . ?
C11A C12A C13A 118(2) . . ?
C13A C12A S1A 112.7(19) . . ?
N4A C13A C12A 108(2) . . ?
N4A C13A H13A 125.9 . . ?
C12A C13A H13A 125.9 . . ?
N4A C14A S1A 113(2) . . ?
N4A C14A N5A 124(3) . . ?
N5A C14A S1A 123(2) . . ?
O1A C15A N5A 124(3) . . ?
O1A C15A C16A 118(3) . . ?
N5A C15A C16A 118(3) . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
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
O3D H3D O1D 0.98 2.34 2.60(4) 93.9 . yes
O5D H5D O2D 0.98 1.63 2.53(3) 150.4 1_565 yes
N3A H3AA O1D 1.03 1.79 2.78(4) 158.7 . 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
O1D C1D C2D O3D 19(5) . . . . ?
O1D C1D C2D C3D -100(4) . . . . ?
O2D C1D C2D O3D -152(4) . . . . ?
O2D C1D C2D C3D 89(4) . . . . ?
O3D C2D C3D C4D 70(3) . . . . ?
C1D C2D C3D C4D -179(2) . . . . ?
C2D C3D C4D O4D 39(5) . . . . ?
C2D C3D C4D O5D -135(3) . . . . ?
S1B C12B C13B N4B 6(4) . . . . ?
N3B C8B C9B C10B 55(3) . . . . ?
N3B C11B C12B S1B -80(2) . . . . ?
N3B C11B C12B C13B 115(4) . . . . ?
C3B N2B C4B N1B 0.0 . . . . ?
C3B N2B C4B C5B -172(2) . . . . ?
N2B C3B C1B F1B 179(3) . . . . ?
N2B C3B C1B C2B 0.0 . . . . ?
N2B C4B N1B C2B 0.0 . . . . ?
N2B C4B C5B C6B -48(3) . . . . ?
C4B N1B C2B C1B 0.0 . . . . ?
C4B C5B C6B C7B -68(3) . . . . ?
C4B C5B C6B C10B -178(2) . . . . ?
N1B C4B C5B C6B 141(2) . . . . ?
N1B C2B C1B F1B -179(3) . . . . ?
N1B C2B C1B C3B 0.0 . . . . ?
C1B C3B N2B C4B 0.0 . . . . ?
C5B C4B N1B C2B 171(3) . . . . ?
C5B C6B C7B N3B -174.0(18) . . . . ?
C5B C6B C10B C9B 174(3) . . . . ?
C7B N3B C8B C9B -62(3) . . . . ?
C7B N3B C11B C12B -166.3(17) . . . . ?
C7B C6B C10B C9B 62(3) . . . . ?
C8B N3B C7B C6B 68(3) . . . . ?
C8B N3B C11B C12B -39(3) . . . . ?
C8B C9B C10B C6B -62(3) . . . . ?
C10B C6B C7B N3B -57(3) . . . . ?
C11B N3B C7B C6B -169.0(17) . . . . ?
C11B N3B C8B C9B -179(2) . . . . ?
C11B C12B C13B N4B 171(3) . . . . ?
C12B S1B C14B N4B 1(3) . . . . ?
C12B S1B C14B N5B 177(3) . . . . ?
C13B N4B C14B S1B 2(3) . . . . ?
C13B N4B C14B N5B -175(3) . . . . ?
C14B S1B C12B C11B -173(2) . . . . ?
C14B S1B C12B C13B -3(2) . . . . ?
C14B N4B C13B C12B -5(4) . . . . ?
C14B N5B C15B O1B -4(5) . . . . ?
C14B N5B C15B C16B 178(3) . . . . ?
C15B N5B C14B S1B 9(4) . . . . ?
C15B N5B C14B N4B -175(2) . . . . ?
S1A C12A C13A N4A 5(3) . . . . ?
F1A C1A C3A N2A 174(3) . . . . ?
N2A C4A N1A C2A 0.0 . . . . ?
N2A C4A C5A C6A -107.8(19) . . . . ?
C4A N2A C3A C1A 0.0 . . . . ?
C4A N1A C2A C1A 0.0 . . . . ?
C4A C5A C6A C7A -173(2) . . . . ?
C4A C5A C6A C10A 61(3) . . . . ?
N1A C4A C5A C6A 74(2) . . . . ?
N1A C2A C1A F1A -176(2) . . . . ?
N1A C2A C1A C3A 0.0 . . . . ?
C2A C1A C3A N2A 0.0 . . . . ?
C3A N2A C4A N1A 0.0 . . . . ?
C3A N2A C4A C5A -178.8(17) . . . . ?
N3A C8A C9A C10A 52(3) . . . . ?
N3A C11A C12A S1A 76(4) . . . . ?
N3A C11A C12A C13A -113(3) . . . . ?
C5A C4A N1A C2A 178(2) . . . . ?
C5A C6A C7A N3A -172.6(19) . . . . ?
C5A C6A C10A C9A 179(2) . . . . ?
C7A N3A C8A C9A -55(4) . . . . ?
C7A N3A C11A C12A 46(3) . . . . ?
C7A C6A C10A C9A 57(3) . . . . ?
C8A N3A C7A C6A 46(3) . . . . ?
C8A N3A C11A C12A -174(2) . . . . ?
C8A C9A C10A C6A -50(3) . . . . ?
C10A C6A C7A N3A -49(3) . . . . ?
C11A N3A C7A C6A -172(2) . . . . ?
C11A N3A C8A C9A 170(2) . . . . ?
C11A C12A C13A N4A -167(3) . . . . ?
C12A S1A C14A N4A -2(3) . . . . ?
C12A S1A C14A N5A -174(3) . . . . ?
C13A N4A C14A S1A 6(4) . . . . ?
C13A N4A C14A N5A 178(3) . . . . ?
C14A S1A C12A C11A 170(3) . . . . ?
C14A S1A C12A C13A -2(2) . . . . ?
C14A N4A C13A C12A -7(4) . . . . ?
C14A N5A C15A O1A 5(6) . . . . ?
C14A N5A C15A C16A -178(3) . . . . ?
C15A N5A C14A S1A -2(5) . . . . ?
C15A N5A C14A N4A -174(3) . . . . ?
_smtbx_masks_special_details     
;
A solvent mask calculation revealed a single void per unit cell 
with a volume of 320Å³ and some additional 
unaccounted-for scattering. The exact composition of this 
solvent void is difficult to assess due to a lack of solvent 
masking tools built specifically for electron diffraction. We 
expect a 1:1 ratio of C16H21FN5OS to D-malate based on 
NMR data and have therefore modeled this void as containing 
a single disordered D-malate. Each non-hydrogen atom in 
D-malate therefore occupies 17.8 Ang³ in this void, which 
is reasonable.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.145 -0.685 0.359 162.0 23.3 '1 D-malate'
2 0.145 -0.198 0.641 162.0 23.3 '1 D-malate'
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: isopropyl acetate'
