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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_rkpq3_abs
_database_code_depnum_ccdc_archive 'CCDC 1998111'
loop_
_audit_author_name
_audit_author_address
'Samantha MacMillan'
;Cornell University
United States of America
;
_audit_update_record             
;
2020-04-20 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_audit_creation_date             2019-05-28
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 F3 O2, C20 H27 N2'
_chemical_formula_sum            'C22 H27 F3 N2 O2'
_chemical_formula_weight         408.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H28F3N2O2
_chemical_oxdiff_usercomment     'Crystallized from MeCN'
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.36910(10)
_cell_length_b                   13.80880(10)
_cell_length_c                   12.46330(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.4170(10)
_cell_angle_gamma                90
_cell_volume                     1947.92(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    67726
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.6770
_cell_measurement_theta_min      4.7850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.657
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
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 colourless'
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 0 -1 0.0832
-1 6 -6 0.0609
1 -6 6 0.0630
7 -2 2 0.0817
7 3 -2 0.0970
-1 6 6 0.0538
-7 4 1 0.0828
-4 -4 -6 0.0604
1 -6 -6 0.0483
4 -6 -4 0.0638
-6 -6 -1 0.0644
0 -9 1 0.0656
0 3 -8 0.0651
5 2 -6 0.0702
7 0 -2 0.0791
4 -2 6 0.0688
-6 -1 6 0.0381
7 1 2 0.0762
0 -1 -8 0.0577
5 -2 -7 0.0559

_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.102
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
-7.1168 0.4318 -1.3592 0.1417 0.0106 0.9899
-0.5081 6.2874 -5.6606 -0.9056 -0.0715 0.4181
0.5179 -6.2855 5.6602 0.9050 0.0714 -0.4194
6.6198 -1.7839 2.4935 0.0705 0.0061 -0.9975
6.7387 3.3348 -2.0420 -0.6821 -0.0533 -0.7293
-0.6010 6.1047 5.9232 -0.0782 0.9939 -0.0777
-6.5350 4.1529 0.8913 -0.0372 0.4758 0.8787
-3.6985 -3.7493 -5.7214 0.0586 -0.7434 0.6663
0.5465 -6.0901 -5.9362 0.0781 -0.9933 0.0856
3.9414 -6.2044 -4.3138 0.0708 -0.9012 -0.4275
-5.5366 -5.7459 -0.7415 0.6450 -0.3950 0.6542
0.0931 -8.8441 1.2941 0.8323 -0.5102 -0.2169
-0.1953 2.6916 -7.6596 -0.7540 -0.5177 0.4043
5.2462 1.6301 -6.0136 -0.7583 -0.5215 -0.3912
7.3350 -0.0853 -1.6355 -0.3883 -0.2676 -0.8818
4.0870 -2.4318 5.9181 0.4613 0.3162 -0.8290
-5.5475 -1.4975 5.7111 0.7376 0.5073 0.4457
7.0097 1.1811 1.5615 -0.2594 0.1245 -0.9577
0.0525 -0.8167 -8.0265 -0.4933 -0.8051 0.3293
4.5058 -1.6950 -6.6587 -0.4946 -0.8069 -0.3228

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            87403
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.042
_diffrn_reflns_theta_min         4.791
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  28.00   0.50    0.18    --   26.00  96.00-122.95   60
  2  ω     27.00  54.00   0.50    0.18    --   48.42  77.00-150.00   54
  3  ω     44.00  72.00   0.50    0.18    --   62.00  72.00-143.36   56
  4  ω     68.00  94.00   0.50    0.18    --   54.00  77.00 -95.72   52
  5  ω    100.00 126.00   0.50    0.18    --   58.00  77.00 -54.87   52
  6  ω     83.00 118.00   0.50    0.73    --  102.00  75.00 -72.98   70
  7  ω    120.00 159.00   0.50    0.73    --  107.75  77.00 -60.00   78
  8  ω    132.00 178.00   0.50    0.73    --  107.75  77.00-120.00   92
  9  ω    146.00 172.00   0.50    0.73    --  107.75  77.00-180.00   52
 10  ω    141.00 167.00   0.50    0.73    --  107.75  77.00-150.00   52
 11  ω    126.00 151.00   0.50    0.73    --  107.75  45.00-120.00   50
 12  ω    125.00 172.00   0.50    0.73    --  107.75  77.00 -90.00   94
 13  ω    133.00 177.00   0.50    0.73    --  107.75 125.00-120.00   88
 14  ω    138.00 175.00   0.50    0.73    --  107.75 116.00   4.00   74
 15  ω    153.00 178.00   0.50    0.73    --  107.75 125.00  90.00   50
 16  ω    141.00 177.00   0.50    0.73    --  107.75  77.00 120.00   72
 17  ω    134.00 160.00   0.50    0.73    --  107.75  61.00 150.00   52
 18  ω    143.00 176.00   0.50    0.73    --  107.75  30.00 150.00   66
 19  ω    153.00 178.00   0.50    0.73    --  107.75  30.00 120.00   50
 20  ω    143.00 171.00   0.50    0.73    --  107.75  61.00  90.00   56
 21  ω    140.00 172.00   0.50    0.73    --  107.75  77.00  60.00   64
 22  ω    134.00 161.00   0.50    0.73    --  107.75  15.00 120.00   54
 23  ω    108.00 133.00   0.50    0.18    --   66.00  78.00 171.77   50
 24  ω     89.00 128.00   0.50    0.73    --  107.75  71.00 112.23   78
 25  ω    113.00 165.00   0.50    0.73    --   94.00  82.00  62.33  104
 26  ω    133.00 169.00   0.50    0.73    --  107.75  77.00  30.00   72
 27  ω    119.00 145.00   0.50    0.73    --  107.75 163.00 152.00   52
 28  ω    110.00 161.00   0.50    0.73    --  107.75 125.00 150.00  102
 29  ω     95.00 135.00   0.50    0.73    --  107.75  61.00  60.00   80
 30  ω    104.00 140.00   0.50    0.73    --  107.75  30.00 120.00   72
 31  ω    105.00 130.00   0.50    0.73    --  107.75  30.00 150.00   50
 32  ω     87.00 118.00   0.50    0.73    --  107.75  77.00 120.00   62
 33  ω     93.00 120.00   0.50    0.73    --  107.75  61.00 150.00   54
 34  ω     93.00 119.00   0.50    0.73    --  107.75  61.00  90.00   52
 35  ω     86.00 125.00   0.50    0.73    --  107.75  77.00  30.00   78
 36  ω    100.00 128.00   0.50    0.73    --  107.75  45.00 -30.00   56
 37  ω    104.00 177.00   0.50    0.73    --  107.75  45.00 -90.00  146
 38  ω    112.00 170.00   0.50    0.73    --  107.75 125.00-180.00  116
 39  ω    101.00 178.00   0.50    0.73    --  107.75  45.00 -60.00  154
 40  ω     99.00 125.00   0.50    0.73    --  107.75  45.00-180.00   52
 41  ω     97.00 123.00   0.50    0.73    --  107.75  45.00-120.00   52
 42  ω     93.00 175.00   0.50    0.73    --  107.75  61.00-120.00  164
 43  ω     94.00 173.00   0.50    0.73    --  107.75  61.00   0.00  158
 44  ω     93.00 144.00   0.50    0.73    --  107.75  61.00 -90.00  102
 45  ω     93.00 141.00   0.50    0.73    --  107.75  61.00-150.00   96
 46  ω     98.00 178.00   0.50    0.73    --  107.75  45.00-150.00  160
 47  ω     95.00 141.00   0.50    0.73    --  107.75  61.00-180.00   92
 48  ω     86.00 112.00   0.50    0.73    --  107.75  77.00 -90.00   52
 49  ω     86.00 112.00   0.50    0.73    --  107.75  77.00 -60.00   52
 50  ω     94.00 149.00   0.50    0.73    --  107.75  61.00 -30.00  110
 51  ω     88.00 155.00   0.50    0.73    --  107.75  73.00  25.94  134
 52  ω     86.00 158.00   0.50    0.73    --  107.75  77.00 150.00  144
 53  ω     95.00 132.00   0.50    0.73    --  107.75 125.00  90.00   74
 54  ω     86.00 153.00   0.50    0.73    --  107.75  77.00   0.00  134
 55  ω     86.00 112.00   0.50    0.73    --  107.75  77.00-120.00   52
 56  ω     86.00 115.00   0.50    0.73    --  107.75  77.00-180.00   58
 57  ω     87.00 113.00   0.50    0.73    --  107.75  77.00-150.00   52
 58  ω     44.00  79.00   0.50    0.18    --   66.00  78.00 -30.45   70
 59  ω     36.00  78.00   0.50    0.18    --   58.00  77.00 -54.87   84
 60  ω     34.00  59.00   0.50    0.18    --   58.00  83.00  -8.67   50
 61  ω     35.00  68.00   0.50    0.18    --   58.00  80.00  15.53   66
 62  ω     46.00  84.00   0.50    0.18    --   66.00  73.00  75.69   76
 63  ω     70.00 108.00   0.50    0.73    --   94.00  82.00  62.33   76
 64  ω     86.00 115.00   0.50    0.73    --  107.75  77.00  90.00   58
 65  ω     87.00 117.00   0.50    0.73    --  107.75  77.00  60.00   60
 66  ω     97.00 131.00   0.50    0.73    --  107.75  15.00 120.00   68
 67  ω    101.00 127.00   0.50    0.73    --  107.75 -82.00 127.28   52
 68  ω     92.00 127.00   0.50    0.73    --  107.75-138.00 138.30   70
 69  ω    107.00 143.00   0.50    0.73    --  107.75-163.00 127.00   72
 70  ω     84.00 109.00   0.50    0.73    --  107.75 -94.00  90.00   50
 71  ω     66.00  95.00   0.50    0.73    --  107.75 -77.00  60.00   58
 72  ω     66.00  92.00   0.50    0.73    --  107.75 -94.00   0.00   52
 73  ω     86.00 111.00   0.50    0.73    --  107.75-105.00 -15.87   50
 74  ω     90.00 116.00   0.50    0.73    --  107.75-125.00 -30.00   52
 75  ω     65.00 113.00   0.50    0.73    --  107.75-116.00 -84.00   96
 76  ω     71.00  96.00   0.50    0.73    --  107.75 -77.00-120.00   50
 77  ω     76.00 116.00   0.50    0.73    --  107.75-125.00-120.00   80
 78  ω     48.00  74.00   0.50    0.73    --  107.75-105.00 -15.87   52
 79  ω     45.00  71.00   0.50    0.73    --  107.75-125.00 -30.00   52
 80  ω     41.00  99.00   0.50    0.73    --  107.75 -94.00  30.00  116
 81  ω     50.00  76.00   0.50    0.73    --  107.75-138.00 138.30   52
 82  ω     64.00 113.00   0.50    0.73    --  107.75-125.00 150.00   98
 83  ω     53.00 116.00   0.50    0.18    --   48.42-163.00 127.00  126
 84  ω     36.00  70.00   0.50    0.73    --  107.75-125.00  60.00   68
 85  ω     43.00  93.00   0.50    0.73    --  107.75 -82.00 127.28  100
 86  ω     37.00  65.00   0.50    0.73    --  107.75 -61.00  30.00   56
 87  ω     41.00  98.00   0.50    0.73    --  107.75 -77.00 -30.00  114
 88  ω     41.00  66.00   0.50    0.73    --  107.75-125.00-120.00   50
 89  ω     36.00 114.00   0.50    0.73    --  107.75-125.00-150.00  156
 90  ω     36.00  99.00   0.50    0.73    --  107.75 -77.00-150.00  126
 91  ω     36.00  75.00   0.50    0.73    --  107.75 -77.00-180.00   78
 92  ω     36.00  70.00   0.50    0.73    --  107.75 -61.00-150.00   68
 93  ω     37.00 103.00   0.50    0.73    --  107.75 -77.00 -90.00  132
 94  ω     38.00  64.00   0.50    0.73    --  107.75 -94.00   0.00   52
 95  ω     36.00  89.00   0.50    0.73    --  107.75 -94.00 -30.00  106
 96  ω     36.00  67.00   0.50    0.73    --  107.75 -61.00-120.00   62
 97  ω     40.00  65.00   0.50    0.73    --  107.75 -94.00 -60.00   50
 98  ω     27.00  89.00   0.50    0.18    --   48.42-116.00 -84.00  124
 99  ω     36.00  88.00   0.50    0.73    --  107.75-125.00-180.00  104
100  ω     32.00  64.00   0.50    0.18    --   54.00  77.00 -95.72   64
101  ω     49.00 100.00   0.50    0.18    --   70.00  76.00-146.20  102
102  ω     86.00 178.00   0.50    0.73    --  107.75  77.00 -30.00  184
103  ω     68.00  94.00   0.50    0.18    --   48.42 163.00 152.00   52
104  ω     34.00  61.00   0.50    0.18    --   54.00  74.00 151.37   54
105  ω     42.00  74.00   0.50    0.18    --   62.00  72.00 118.26   64
106  ω     44.00  69.00   0.50    0.18    --   66.00  77.00 162.04   50
107  ω     44.00  70.00   0.50    0.18    --   66.00  78.00 171.77   52
108  ω     20.00  45.00   0.50    0.18    --   46.00  86.00  87.55   50
109  ω     33.00 105.00   0.50    0.18    --   54.00  79.00  78.14  144
110  ω     26.00  52.00   0.50    0.18    --   50.00  83.00 -31.47   52
111  ω     15.00  40.00   0.50    0.18    --   42.00  89.00  48.19   50
112  ω     33.00  76.00   0.50    0.18    --   54.00  77.00  57.16   86
113  ω     18.00  43.00   0.50    0.18    --   46.00  90.00 129.77   50
114  ω    -10.00  15.00   0.50    0.18    --   22.00 101.00  43.46   50
115  ω      3.00  28.00   0.50    0.18    --   34.00  97.00 -17.08   50
116  ω    -14.00  28.00   0.50    0.18    --   18.00  98.00 -58.66   84
117  ω     26.00  69.00   0.50    0.18    --   50.00  82.00-133.26   86
118  ω    -38.00  -8.00   0.50    0.18    --    6.00 122.00-168.12   60
119  ω    -60.00  -7.00   0.50    0.18    --  -48.42 116.00   4.00  106
120  ω    -75.00 -50.00   0.50    0.73    --  -86.25 116.00   4.00   50
121  ω    -97.00 -72.00   0.50    0.18    --  -48.42 163.00 152.00   50
122  ω    -97.00 -72.00   0.50    0.73    --  -86.25 163.00 152.00   50
123  ω    -11.00  17.00   0.50    0.18    --   22.00 102.00 133.10   56
124  ω     45.00  71.00   0.50    0.73    --  107.75 -61.00 120.00   52
125  ω     40.00  77.00   0.50    0.73    --  107.75 -77.00 150.00   74
126  ω     37.00  71.00   0.50    0.73    --  107.75 -94.00  90.00   68
127  ω    -66.00 -25.00   0.50    0.18    --  -50.00 -83.00 -64.91   82
128  ω    -67.00 -41.00   0.50    0.18    --  -66.00 -83.00  16.91   52
129  ω    -77.00 -48.00   0.50    0.18    --  -66.00 -69.00  99.60   58
130  ω    -76.00 -50.00   0.50    0.73    --  -74.00 -81.00 109.99   52
131  ω    -81.00 -55.00   0.50    0.73    --  -78.00 -83.00  77.26   52
132  ω    -83.00 -57.00   0.50    0.73    --  -78.00 -74.00 128.75   52
133  ω    -92.00 -63.00   0.50    0.73    --  -82.00 -69.00 152.11   58
134  ω    -93.00 -66.00   0.50    0.73    --  -86.25 -73.00 128.46   54
135  ω    -92.00 -66.00   0.50    0.73    --  -86.25 -74.00  97.97   52
136  ω   -105.00 -66.00   0.50    0.73    --  -86.25 -73.00  14.07   78
137  ω    -83.00 -51.00   0.50    0.73    --  -70.00 -69.00 -23.66   64
138  ω    -68.00 -42.00   0.50    0.18    --  -66.00 -83.00 -79.26   52
139  ω    -69.00 -42.00   0.50    0.18    --  -66.00 -81.00-137.38   54
140  ω    -75.00 -49.00   0.50    0.73    --  -74.00 -83.00-177.70   52
141  ω   -105.00 -53.00   0.50    0.73    --  -74.00 -75.00-100.88  104
142  ω   -100.00 -64.00   0.50    0.73    --  -86.25 -77.00   0.00   72
143  ω   -104.00 -67.00   0.50    0.73    --  -86.25 -71.00 -47.43   74
144  ω   -101.00 -64.00   0.50    0.73    --  -86.25 -77.00  30.00   74
145  ω   -102.00 -67.00   0.50    0.73    --  -86.25 -74.00 -54.55   70
146  ω    -98.00 -65.00   0.50    0.73    --  -86.25 -76.00-137.08   66
147  ω   -117.00 -64.00   0.50    0.73    --  -86.25 -77.00-150.00  106
148  ω   -110.00 -66.00   0.50    0.73    --  -86.25 -77.00 -90.00   88
149  ω   -116.00 -66.00   0.50    0.73    --  -86.25 -74.00 -21.80  100
150  ω   -122.00 -64.00   0.50    0.73    --  -86.25 -77.00  90.00  116
151  ω    -98.00 -64.00   0.50    0.73    --  -86.25 -77.00 120.00   68
152  ω   -101.00 -68.00   0.50    0.73    --  -86.25 -69.00 179.45   66
153  ω   -112.00 -68.00   0.50    0.73    --  -86.25 -67.00 151.41   88
154  ω   -115.00 -66.00   0.50    0.18    --  -48.42-163.00 127.00   98
155  ω   -119.00 -94.00   0.50    0.73    --  -86.25-163.00 127.00   50
156  ω   -158.00 -65.00   0.50    0.73    --  -86.25 -77.00  60.00  186
157  ω   -141.00-116.00   0.50    0.73    --  -86.25-116.00 -84.00   50
158  ω   -152.00 -62.00   0.50    0.73    --  -82.00 -73.00-120.55  180
159  ω   -155.00-123.00   0.50    0.73    --  -86.25 -74.00 -21.80   64
160  ω   -158.00-109.00   0.50    0.73    --  -86.25 -74.00 -54.55   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0383532000
_diffrn_orient_matrix_UB_12      -0.0842970000
_diffrn_orient_matrix_UB_13      0.0697881000
_diffrn_orient_matrix_UB_21      -0.0149316000
_diffrn_orient_matrix_UB_22      0.0711316000
_diffrn_orient_matrix_UB_23      0.0929713000
_diffrn_orient_matrix_UB_31      -0.1297442000
_diffrn_orient_matrix_UB_32      0.0167832000
_diffrn_orient_matrix_UB_33      -0.0435822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4008
_reflns_number_total             4166
_reflns_odcompleteness_completeness 97.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.034
_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)+(0.0476P)²+1.0859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.0996
_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
2. Restrained distances
 N1-H1
 0.88 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1A), C4(H4), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B), C11(H11A,
 H11B), C14(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.70640(9) 0.22246(8) 0.59090(8) 0.0506(3) Uani 1 1 d . . . . .
F2 F 0.87223(9) 0.27023(6) 0.66479(7) 0.0418(2) Uani 1 1 d . . . . .
F3 F 0.86544(13) 0.16698(7) 0.53671(8) 0.0616(3) Uani 1 1 d . . . . .
O1 O 0.78675(10) 0.30223(7) 0.39111(8) 0.0352(2) Uani 1 1 d . . . . .
O2 O 0.83166(8) 0.41097(6) 0.52300(7) 0.0243(2) Uani 1 1 d . . . . .
C21 C 0.81061(10) 0.32864(8) 0.48509(10) 0.0199(2) Uani 1 1 d . . . . .
C22 C 0.81528(12) 0.24682(9) 0.57033(10) 0.0245(3) Uani 1 1 d . . . . .
N1 N 0.77239(8) 0.56276(7) 0.39630(7) 0.01418(19) Uani 1 1 d D . . . .
H1 H 0.7965(12) 0.5099(10) 0.4358(11) 0.017 Uiso 1 1 d DR . . . .
N2 N 0.65520(8) 0.58874(7) 0.43050(7) 0.01536(19) Uani 1 1 d . . . . .
C1 C 0.86229(10) 0.64226(8) 0.42254(9) 0.0167(2) Uani 1 1 d . . . . .
H1A H 0.935215 0.630613 0.385402 0.020 Uiso 1 1 calc R . . . .
C2 C 0.88949(10) 0.63664(9) 0.54529(9) 0.0187(2) Uani 1 1 d . . . . .
H2A H 0.935329 0.694214 0.571775 0.022 Uiso 1 1 calc R . . . .
H2B H 0.937008 0.578117 0.564955 0.022 Uiso 1 1 calc R . . . .
C3 C 0.77090(10) 0.63246(9) 0.59715(9) 0.0188(2) Uani 1 1 d . . . . .
H3A H 0.755226 0.565437 0.620149 0.023 Uiso 1 1 calc R . . . .
H3B H 0.774539 0.675000 0.661312 0.023 Uiso 1 1 calc R . . . .
C4 C 0.67263(10) 0.66622(8) 0.51336(9) 0.0173(2) Uani 1 1 d . . . . .
H4 H 0.597996 0.675800 0.548537 0.021 Uiso 1 1 calc R . . . .
C5 C 0.71102(10) 0.76299(8) 0.46580(9) 0.0195(2) Uani 1 1 d . . . . .
H5A H 0.742630 0.807014 0.524250 0.023 Uiso 1 1 calc R . . . .
H5B H 0.642708 0.794846 0.425049 0.023 Uiso 1 1 calc R . . . .
C6 C 0.80749(10) 0.74006(8) 0.39013(9) 0.0191(2) Uani 1 1 d . . . . .
H6A H 0.772334 0.737786 0.314415 0.023 Uiso 1 1 calc R . . . .
H6B H 0.868891 0.791110 0.396341 0.023 Uiso 1 1 calc R . . . .
C7 C 0.74795(9) 0.52493(8) 0.28117(8) 0.0151(2) Uani 1 1 d . . . . .
H7 H 0.727058 0.454916 0.287100 0.018 Uiso 1 1 calc R . . . .
C8 C 0.63567(9) 0.57672(8) 0.23421(9) 0.0153(2) Uani 1 1 d . . . . .
H8 H 0.653419 0.630018 0.183869 0.018 Uiso 1 1 calc R . . . .
C9 C 0.54206(10) 0.50586(8) 0.18191(9) 0.0179(2) Uani 1 1 d . . . . .
H9 H 0.572993 0.457232 0.132178 0.021 Uiso 1 1 calc R . . . .
C10 C 0.43676(10) 0.56619(9) 0.13205(10) 0.0214(2) Uani 1 1 d . . . . .
H10A H 0.380360 0.525488 0.086536 0.026 Uiso 1 1 calc R . . . .
H10B H 0.463694 0.620100 0.088074 0.026 Uiso 1 1 calc R . . . .
C11 C 0.37991(10) 0.60496(9) 0.23282(10) 0.0231(3) Uani 1 1 d . . . . .
H11A H 0.381891 0.676596 0.235512 0.028 Uiso 1 1 calc R . . . .
H11B H 0.297073 0.582850 0.232798 0.028 Uiso 1 1 calc R . . . .
C12 C 0.45835(10) 0.56080(9) 0.32775(9) 0.0196(2) Uani 1 1 d . . . . .
H12 H 0.421217 0.557535 0.397265 0.024 Uiso 1 1 calc R . . . .
C13 C 0.57678(9) 0.61536(8) 0.33324(9) 0.0162(2) Uani 1 1 d . . . . .
H13 H 0.564344 0.686988 0.328625 0.019 Uiso 1 1 calc R . . . .
C14 C 0.49086(10) 0.46234(8) 0.28132(9) 0.0199(2) Uani 1 1 d . . . . .
H14A H 0.421054 0.420789 0.262190 0.024 Uiso 1 1 calc R . . . .
H14B H 0.550569 0.426806 0.329118 0.024 Uiso 1 1 calc R . . . .
C15 C 0.85674(10) 0.52903(8) 0.22050(9) 0.0164(2) Uani 1 1 d . . . . .
C16 C 0.88596(11) 0.60989(9) 0.16124(10) 0.0209(2) Uani 1 1 d . . . . .
H16 H 0.834793 0.664402 0.155191 0.025 Uiso 1 1 calc R . . . .
C17 C 0.99030(11) 0.61043(10) 0.11099(10) 0.0245(3) Uani 1 1 d . . . . .
H17 H 1.010253 0.665656 0.071019 0.029 Uiso 1 1 calc R . . . .
C18 C 1.06517(10) 0.53121(10) 0.11881(10) 0.0252(3) Uani 1 1 d . . . . .
H18 H 1.136438 0.532251 0.084696 0.030 Uiso 1 1 calc R . . . .
C19 C 1.03590(11) 0.45043(10) 0.17648(10) 0.0248(3) Uani 1 1 d . . . . .
H19 H 1.086876 0.395781 0.181510 0.030 Uiso 1 1 calc R . . . .
C20 C 0.93183(10) 0.44916(9) 0.22713(9) 0.0194(2) Uani 1 1 d . . . . .
H20 H 0.911977 0.393496 0.266424 0.023 Uiso 1 1 calc R . . . .


_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
F1 C22 1.3308(16) . ?
F2 C22 1.3288(16) . ?
F3 C22 1.3272(15) . ?
O1 C21 1.2323(16) . ?
O2 C21 1.2456(15) . ?
C21 C22 1.5484(16) . ?
N1 N2 1.4808(12) . ?
N1 C1 1.5145(13) . ?
N1 C7 1.5276(13) . ?
N2 C4 1.4872(14) . ?
N2 C13 1.4817(14) . ?
C1 C2 1.5339(15) . ?
C1 C6 1.5256(15) . ?
C2 C3 1.5502(15) . ?
C3 C4 1.5283(15) . ?
C4 C5 1.5415(15) . ?
C5 C6 1.5452(16) . ?
C7 C8 1.5305(14) . ?
C7 C15 1.5104(15) . ?
C8 C9 1.5440(15) . ?
C8 C13 1.5531(15) . ?
C9 C10 1.5404(16) . ?
C9 C14 1.5399(15) . ?
C10 C11 1.5605(16) . ?
C11 C12 1.5387(16) . ?
C12 C13 1.5388(15) . ?
C12 C14 1.5363(16) . ?
C15 C16 1.3960(16) . ?
C15 C20 1.3925(16) . ?
C16 C17 1.3928(16) . ?
C17 C18 1.3838(19) . ?
C18 C19 1.3845(19) . ?
C19 C20 1.3927(16) . ?

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
O1 C21 O2 130.37(11) . . ?
O1 C21 C22 115.24(11) . . ?
O2 C21 C22 114.39(10) . . ?
F1 C22 C21 110.14(11) . . ?
F2 C22 F1 105.97(11) . . ?
F2 C22 C21 114.37(10) . . ?
F3 C22 F1 106.62(12) . . ?
F3 C22 F2 107.09(12) . . ?
F3 C22 C21 112.18(10) . . ?
N2 N1 C1 111.68(8) . . ?
N2 N1 C7 105.33(8) . . ?
C1 N1 C7 120.66(8) . . ?
N1 N2 C4 108.03(8) . . ?
N1 N2 C13 108.23(8) . . ?
C13 N2 C4 114.84(9) . . ?
N1 C1 C2 104.31(8) . . ?
N1 C1 C6 109.51(9) . . ?
C6 C1 C2 110.34(9) . . ?
C1 C2 C3 108.44(9) . . ?
C4 C3 C2 108.19(9) . . ?
N2 C4 C3 107.21(9) . . ?
N2 C4 C5 112.37(9) . . ?
C3 C4 C5 108.18(9) . . ?
C4 C5 C6 107.46(9) . . ?
C1 C6 C5 108.39(9) . . ?
N1 C7 C8 105.70(8) . . ?
C15 C7 N1 111.87(8) . . ?
C15 C7 C8 118.94(9) . . ?
C7 C8 C9 112.47(9) . . ?
C7 C8 C13 105.26(8) . . ?
C9 C8 C13 102.80(8) . . ?
C10 C9 C8 107.82(9) . . ?
C14 C9 C8 101.86(9) . . ?
C14 C9 C10 101.38(9) . . ?
C9 C10 C11 103.06(9) . . ?
C12 C11 C10 103.23(9) . . ?
C11 C12 C13 106.34(9) . . ?
C14 C12 C11 101.76(9) . . ?
C14 C12 C13 102.09(9) . . ?
N2 C13 C8 107.08(8) . . ?
N2 C13 C12 111.79(9) . . ?
C12 C13 C8 103.74(9) . . ?
C12 C14 C9 94.60(9) . . ?
C16 C15 C7 122.81(10) . . ?
C20 C15 C7 117.85(10) . . ?
C20 C15 C16 119.32(10) . . ?
C17 C16 C15 119.84(11) . . ?
C18 C17 C16 120.56(12) . . ?
C17 C18 C19 119.80(11) . . ?
C18 C19 C20 120.11(11) . . ?
C15 C20 C19 120.36(11) . . ?

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
N1 H1 O2 0.908(12) 1.768(12) 2.6721(12) 173.5(13) .

_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 1.170
_oxdiff_exptl_absorpt_empirical_full_min 0.890
