# Electronic Supplementary Material (ESI) for RSC Chemical Biology.
# 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_wpu21004
_database_code_depnum_ccdc_archive 'CCDC 2122955'
loop_
_audit_author_name
_audit_author_address
'Dr. Adrian C. Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2021-11-18 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_audit_creation_date             2021-03-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
''
''
_chemical_name_common            KP439_C
_chemical_name_systematic        5-(4-fluorobenzyl)-1,5-diazecane-2,6-dione
_chemical_formula_moiety         'C15 H19 F N2 O2'
_chemical_formula_sum            'C15 H19 F N2 O2'
_chemical_formula_weight         278.32
_chemical_melting_point          435-438
_chemical_oxdiff_formula         'C15 H19 F1 N2 O2'
_chemical_oxdiff_usercomment     'Kleopas Palate KP439_C'
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.0133(3)
_cell_length_b                   11.5495(3)
_cell_length_c                   24.5641(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.326(2)
_cell_angle_gamma                90
_cell_volume                     2803.24(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3876
_cell_measurement_temperature    110.00(14)
_cell_measurement_theta_max      70.8530
_cell_measurement_theta_min      4.2230
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 -1 0.0918
-2 0 1 0.0918
-2 1 2 0.0975
2 -1 1 0.0930
-2 1 -1 0.0930
2 -1 -1 0.0941
0 0 1 0.0228
0 0 -1 0.0354
0 1 -1 0.0338
0 -1 1 0.0370
0 -1 0 0.0318
0 2 1 0.0330
-1 -1 2 0.0746

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: crystallisation from chloroform, dichloromethane and hexane'
_exptl_crystal_size_max          0.186
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.058
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
2.0021 0.0013 -1.0038 0.0723 0.2993 -0.0156
-2.0021 -0.0013 1.0038 -0.0723 -0.2993 0.0156
-2.0022 0.9996 2.0035 -0.1860 -0.2699 0.1053
2.0017 -0.9964 0.9952 0.2243 0.2618 0.0812
-2.0017 0.9964 -0.9952 -0.2243 -0.2618 -0.0812
2.0021 -0.9985 -1.0039 0.1988 0.2672 -0.0431
-0.0002 0.0011 0.9996 0.0128 -0.0027 0.0622
0.0002 -0.0011 -0.9996 -0.0128 0.0027 -0.0622
0.0002 0.9987 -0.9994 -0.1393 0.0348 -0.0346
-0.0002 -0.9987 0.9994 0.1393 -0.0348 0.0346
-0.0000 -0.9998 -0.0002 0.1265 -0.0322 -0.0275
-0.0001 2.0007 0.9999 -0.2401 0.0616 0.1172
-1.0013 -0.9988 2.0011 0.1095 -0.1859 0.0735

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15003
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         3.647
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1450
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  30.00   1.00    5.00    --    0.00 -77.00-150.00   51
  2  ω    -21.00  30.00   1.00    5.00    --    0.00 -77.00 150.00   51
  3  ω    -21.00  30.00   1.00    5.00    --    0.00 -77.00 -60.00   51
  4  ω    -21.00  30.00   1.00    5.00    --    0.00 -77.00   0.00   51
  5  ω    -15.00  75.00   1.00   20.00    --   54.00 -57.00-120.00   90
  6  ω     33.00 123.00   1.00   20.00    --   54.00  57.00-150.00   90
  7  ω    -16.00  84.00   1.00   20.00    --   54.00 -77.00  60.00  100
  8  ω    -15.00  75.00   1.00   20.00    --   54.00 -57.00  90.00   90
  9  ω     27.00 111.00   1.00   20.00    --   54.00-125.00-180.00   84
 10  ω     40.00 130.00   1.00   20.00    --  108.00 -63.00-120.00   90
 11  ω     38.00 130.00   1.00   20.00    --  108.00 -50.00 120.00   92
 12  ω     82.00 178.00   1.00   20.00    --  108.00  38.00-150.00   96
 13  ω     36.00 107.00   1.00   20.00    --  108.00 -91.00 -90.00   71
 14  ω     61.00 146.00   1.00   20.00    --  108.00 178.00   0.00   85
 15  ω     61.00 146.00   1.00   20.00    --  108.00 178.00-180.00   85
 16  ω    103.00 178.00   1.00   20.00    --  108.00  77.00 -30.00   75
 17  ω     49.00 130.00   1.00   20.00    --  108.00 -63.00  30.00   81
 18  ω    111.00 146.00   1.00   20.00    --  108.00 178.00 120.00   35
 19  ω     66.00  93.00   1.00   20.00    --  108.00 178.00 120.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0426829000
_diffrn_orient_matrix_UB_12      -0.1264952000
_diffrn_orient_matrix_UB_13      0.0129356000
_diffrn_orient_matrix_UB_21      0.1481323000
_diffrn_orient_matrix_UB_22      0.0321617000
_diffrn_orient_matrix_UB_23      -0.0027024000
_diffrn_orient_matrix_UB_31      0.0233520000
_diffrn_orient_matrix_UB_32      0.0275175000
_diffrn_orient_matrix_UB_33      0.0621616000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4052
_reflns_number_total             5000
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.213
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     513
_refine_ls_number_reflns         5000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²+1.0135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1016
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
C1 C 0.85750(15) 0.72008(13) 0.79208(6) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.75989(16) 0.73540(14) 0.83289(6) 0.0179(3) Uani 1 1 d . . . . .
H2A H 0.7129(18) 0.6621(16) 0.8418(7) 0.021(4) Uiso 1 1 d . . . . .
H2B H 0.6838(18) 0.7865(15) 0.8154(7) 0.020(4) Uiso 1 1 d . . . . .
C3 C 0.82776(17) 0.79492(15) 0.88616(7) 0.0223(4) Uani 1 1 d . . . . .
H3A H 0.8525(17) 0.8746(16) 0.8771(7) 0.020(4) Uiso 1 1 d . . . . .
H3B H 0.7564(19) 0.8012(16) 0.9104(7) 0.028(5) Uiso 1 1 d . . . . .
C4 C 0.95489(18) 0.73640(16) 0.91706(7) 0.0246(4) Uani 1 1 d . . . . .
H4A H 1.0257(18) 0.7294(16) 0.8929(7) 0.025(5) Uiso 1 1 d . . . . .
H4B H 0.9895(18) 0.7870(16) 0.9466(7) 0.024(5) Uiso 1 1 d . . . . .
C5 C 0.93643(19) 0.61821(16) 0.94289(7) 0.0265(4) Uani 1 1 d . . . . .
H5A H 0.8692(19) 0.6230(16) 0.9685(7) 0.026(5) Uiso 1 1 d . . . . .
H5B H 1.025(2) 0.5926(17) 0.9643(8) 0.034(5) Uiso 1 1 d . . . . .
C6 C 0.96893(16) 0.48704(13) 0.86733(6) 0.0202(3) Uani 1 1 d . . . . .
C7 C 0.89463(18) 0.42395(14) 0.81761(7) 0.0223(4) Uani 1 1 d . . . . .
H7A H 0.9582(18) 0.3900(15) 0.7972(7) 0.021(4) Uiso 1 1 d . . . . .
H7B H 0.8363(19) 0.3633(16) 0.8288(7) 0.025(5) Uiso 1 1 d . . . . .
C8 C 0.80218(17) 0.50747(14) 0.77988(6) 0.0188(3) Uani 1 1 d . . . . .
H8A H 0.7685(16) 0.4691(15) 0.7441(7) 0.016(4) Uiso 1 1 d . . . . .
H8B H 0.7214(17) 0.5264(14) 0.7957(6) 0.014(4) Uiso 1 1 d . . . . .
C9 C 0.96937(16) 0.60262(14) 0.73052(6) 0.0178(3) Uani 1 1 d . . . . .
H9A H 1.0390(18) 0.6649(16) 0.7393(7) 0.022(5) Uiso 1 1 d . . . . .
H9B H 1.0130(17) 0.5255(16) 0.7373(7) 0.017(4) Uiso 1 1 d . . . . .
C10 C 0.90652(15) 0.61270(13) 0.67043(6) 0.0165(3) Uani 1 1 d . . . . .
C11 C 0.85492(16) 0.71824(14) 0.64868(7) 0.0201(3) Uani 1 1 d . . . . .
H11 H 0.8540(16) 0.7832(15) 0.6720(7) 0.017(4) Uiso 1 1 d . . . . .
C12 C 0.80171(17) 0.72946(15) 0.59347(7) 0.0230(4) Uani 1 1 d . . . . .
H12 H 0.768(2) 0.8021(18) 0.5775(8) 0.035(5) Uiso 1 1 d . . . . .
C13 C 0.79970(17) 0.63323(15) 0.56033(6) 0.0230(4) Uani 1 1 d . . . . .
C14 C 0.84987(18) 0.52804(15) 0.57975(7) 0.0249(4) Uani 1 1 d . . . . .
H14 H 0.8459(19) 0.4643(17) 0.5555(7) 0.031(5) Uiso 1 1 d . . . . .
C15 C 0.90363(17) 0.51803(14) 0.63532(7) 0.0215(4) Uani 1 1 d . . . . .
H15 H 0.9415(18) 0.4442(17) 0.6509(7) 0.026(5) Uiso 1 1 d . . . . .
F1 F 0.74510(11) 0.64301(10) 0.50614(4) 0.0370(3) Uani 1 1 d . . . . .
N1 N 0.87089(13) 0.61441(11) 0.76880(5) 0.0163(3) Uani 1 1 d . . . . .
N2 N 0.89065(15) 0.52849(12) 0.90207(5) 0.0213(3) Uani 1 1 d . . . . .
H2 H 0.805(2) 0.5118(17) 0.8962(8) 0.028(5) Uiso 1 1 d . . . . .
O1 O 0.92244(11) 0.80465(9) 0.77994(4) 0.0203(3) Uani 1 1 d . . . . .
O2 O 1.09248(11) 0.50430(10) 0.87341(5) 0.0254(3) Uani 1 1 d . . . . .
C16 C 0.36637(16) 0.70640(13) 0.78781(6) 0.0168(3) Uani 1 1 d . . . . .
C17 C 0.27038(16) 0.72567(14) 0.82892(6) 0.0179(3) Uani 1 1 d . . . . .
H17A H 0.2260(18) 0.6538(16) 0.8384(7) 0.020(4) Uiso 1 1 d . . . . .
H17B H 0.1958(18) 0.7760(16) 0.8101(7) 0.025(5) Uiso 1 1 d . . . . .
C18 C 0.33928(18) 0.78930(14) 0.88090(6) 0.0218(4) Uani 1 1 d . . . . .
H18A H 0.2688(18) 0.8033(15) 0.9041(7) 0.022(4) Uiso 1 1 d . . . . .
H18B H 0.3700(19) 0.8664(17) 0.8693(8) 0.032(5) Uiso 1 1 d . . . . .
C19 C 0.46022(17) 0.72938(15) 0.91538(7) 0.0228(4) Uani 1 1 d . . . . .
H19A H 0.4990(18) 0.7831(16) 0.9443(7) 0.022(4) Uiso 1 1 d . . . . .
H19B H 0.5306(18) 0.7145(15) 0.8928(7) 0.022(5) Uiso 1 1 d . . . . .
C20 C 0.43090(18) 0.61623(15) 0.94342(6) 0.0236(4) Uani 1 1 d . . . . .
H20A H 0.3552(19) 0.6248(16) 0.9644(7) 0.026(5) Uiso 1 1 d . . . . .
H20B H 0.514(2) 0.5935(17) 0.9686(8) 0.030(5) Uiso 1 1 d . . . . .
C21 C 0.48014(16) 0.48021(13) 0.87301(6) 0.0194(3) Uani 1 1 d . . . . .
C22 C 0.41967(18) 0.41410(14) 0.82206(7) 0.0207(3) Uani 1 1 d . . . . .
H22A H 0.4946(19) 0.3863(16) 0.8052(7) 0.024(5) Uiso 1 1 d . . . . .
H22B H 0.3690(19) 0.3477(17) 0.8320(7) 0.028(5) Uiso 1 1 d . . . . .
C23 C 0.32162(17) 0.49020(13) 0.78263(6) 0.0193(3) Uani 1 1 d . . . . .
H23A H 0.2385(19) 0.5070(15) 0.7989(7) 0.023(5) Uiso 1 1 d . . . . .
H23B H 0.2891(18) 0.4489(16) 0.7477(7) 0.023(5) Uiso 1 1 d . . . . .
C24 C 0.47373(16) 0.58668(14) 0.72641(6) 0.0183(3) Uani 1 1 d . . . . .
H24A H 0.5500(19) 0.6403(16) 0.7350(7) 0.022(5) Uiso 1 1 d . . . . .
H24B H 0.5087(18) 0.5034(16) 0.7286(7) 0.021(4) Uiso 1 1 d . . . . .
C25 C 0.40514(16) 0.61329(13) 0.66807(6) 0.0176(3) Uani 1 1 d . . . . .
C26 C 0.26870(17) 0.63572(15) 0.65413(6) 0.0229(4) Uani 1 1 d . . . . .
H26 H 0.209(2) 0.6304(16) 0.6827(8) 0.033(5) Uiso 1 1 d . . . . .
C27 C 0.21021(18) 0.66261(15) 0.60057(7) 0.0248(4) Uani 1 1 d . . . . .
H27 H 0.114(2) 0.6769(17) 0.5903(7) 0.029(5) Uiso 1 1 d . . . . .
C28 C 0.29324(18) 0.66666(15) 0.56137(6) 0.0251(4) Uani 1 1 d . . . . .
C29 C 0.42915(19) 0.64332(18) 0.57290(7) 0.0332(4) Uani 1 1 d . . . . .
H29 H 0.484(2) 0.6441(19) 0.5419(8) 0.045(6) Uiso 1 1 d . . . . .
C30 C 0.48507(18) 0.61622(16) 0.62649(7) 0.0268(4) Uani 1 1 d . . . . .
H30 H 0.584(2) 0.6004(17) 0.6365(7) 0.033(5) Uiso 1 1 d . . . . .
F2 F 0.23767(11) 0.69568(10) 0.50854(4) 0.0381(3) Uani 1 1 d . . . . .
N3 N 0.38474(13) 0.59794(11) 0.76807(5) 0.0169(3) Uani 1 1 d . . . . .
N4 N 0.39199(14) 0.52271(12) 0.90377(5) 0.0193(3) Uani 1 1 d . . . . .
H4 H 0.3050(19) 0.5111(15) 0.8931(7) 0.016(4) Uiso 1 1 d . . . . .
O3 O 0.42582(12) 0.79005(9) 0.77196(4) 0.0225(3) Uani 1 1 d . . . . .
O4 O 0.60276(12) 0.49853(10) 0.88436(5) 0.0267(3) 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
C1 C2 1.520(2) . ?
C1 N1 1.3636(19) . ?
C1 O1 1.2364(18) . ?
C2 H2A 1.009(19) . ?
C2 H2B 1.004(18) . ?
C2 C3 1.536(2) . ?
C3 H3A 0.987(18) . ?
C3 H3B 1.004(19) . ?
C3 C4 1.530(2) . ?
C4 H4A 0.999(18) . ?
C4 H4B 0.951(19) . ?
C4 C5 1.529(2) . ?
C5 H5A 0.994(19) . ?
C5 H5B 1.00(2) . ?
C5 N2 1.463(2) . ?
C6 C7 1.511(2) . ?
C6 N2 1.337(2) . ?
C6 O2 1.238(2) . ?
C7 H7A 0.956(18) . ?
C7 H7B 0.980(19) . ?
C7 C8 1.539(2) . ?
C8 H8A 0.994(17) . ?
C8 H8B 0.977(17) . ?
C8 N1 1.461(2) . ?
C9 H9A 1.000(19) . ?
C9 H9B 0.994(18) . ?
C9 C10 1.513(2) . ?
C9 N1 1.4749(19) . ?
C10 C11 1.396(2) . ?
C10 C15 1.390(2) . ?
C11 H11 0.945(18) . ?
C11 C12 1.380(2) . ?
C12 H12 0.96(2) . ?
C12 C13 1.376(2) . ?
C13 C14 1.371(2) . ?
C13 F1 1.3594(18) . ?
C14 H14 0.94(2) . ?
C14 C15 1.389(2) . ?
C15 H15 0.985(19) . ?
N2 H2 0.87(2) . ?
C16 C17 1.519(2) . ?
C16 N3 1.3664(19) . ?
C16 O3 1.2306(19) . ?
C17 H17A 0.988(19) . ?
C17 H17B 0.998(19) . ?
C17 C18 1.537(2) . ?
C18 H18A 0.989(18) . ?
C18 H18B 1.00(2) . ?
C18 C19 1.527(2) . ?
C19 H19A 0.975(19) . ?
C19 H19B 0.981(18) . ?
C19 C20 1.528(2) . ?
C20 H20A 0.987(19) . ?
C20 H20B 0.992(19) . ?
C20 N4 1.464(2) . ?
C21 C22 1.507(2) . ?
C21 N4 1.344(2) . ?
C21 O4 1.233(2) . ?
C22 H22A 0.968(19) . ?
C22 H22B 0.97(2) . ?
C22 C23 1.538(2) . ?
C23 H23A 0.999(19) . ?
C23 H23B 0.989(18) . ?
C23 N3 1.4659(19) . ?
C24 H24A 0.979(19) . ?
C24 H24B 1.022(18) . ?
C24 C25 1.517(2) . ?
C24 N3 1.4677(19) . ?
C25 C26 1.378(2) . ?
C25 C30 1.396(2) . ?
C26 H26 0.995(19) . ?
C26 C27 1.386(2) . ?
C27 H27 0.966(19) . ?
C27 C28 1.371(2) . ?
C28 C29 1.371(3) . ?
C28 F2 1.3681(18) . ?
C29 H29 1.00(2) . ?
C29 C30 1.380(2) . ?
C30 H30 1.00(2) . ?
N4 H4 0.878(18) . ?

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
N1 C1 C2 119.89(13) . . ?
O1 C1 C2 119.13(14) . . ?
O1 C1 N1 120.97(14) . . ?
C1 C2 H2A 114.7(10) . . ?
C1 C2 H2B 108.1(10) . . ?
C1 C2 C3 111.78(13) . . ?
H2A C2 H2B 103.7(14) . . ?
C3 C2 H2A 110.4(9) . . ?
C3 C2 H2B 107.6(10) . . ?
C2 C3 H3A 108.5(10) . . ?
C2 C3 H3B 106.2(11) . . ?
H3A C3 H3B 107.1(14) . . ?
C4 C3 C2 116.28(14) . . ?
C4 C3 H3A 107.7(10) . . ?
C4 C3 H3B 110.7(10) . . ?
C3 C4 H4A 110.8(10) . . ?
C3 C4 H4B 106.1(11) . . ?
H4A C4 H4B 107.2(15) . . ?
C5 C4 C3 116.97(15) . . ?
C5 C4 H4A 108.6(11) . . ?
C5 C4 H4B 106.6(11) . . ?
C4 C5 H5A 110.6(11) . . ?
C4 C5 H5B 108.9(12) . . ?
H5A C5 H5B 108.6(15) . . ?
N2 C5 C4 113.17(13) . . ?
N2 C5 H5A 107.7(11) . . ?
N2 C5 H5B 107.7(11) . . ?
N2 C6 C7 115.20(14) . . ?
O2 C6 C7 121.78(15) . . ?
O2 C6 N2 122.90(16) . . ?
C6 C7 H7A 109.8(10) . . ?
C6 C7 H7B 110.8(10) . . ?
C6 C7 C8 110.73(13) . . ?
H7A C7 H7B 109.4(15) . . ?
C8 C7 H7A 109.2(10) . . ?
C8 C7 H7B 106.8(11) . . ?
C7 C8 H8A 109.7(10) . . ?
C7 C8 H8B 110.9(9) . . ?
H8A C8 H8B 105.5(13) . . ?
N1 C8 C7 112.75(13) . . ?
N1 C8 H8A 108.4(10) . . ?
N1 C8 H8B 109.3(10) . . ?
H9A C9 H9B 109.6(14) . . ?
C10 C9 H9A 108.6(10) . . ?
C10 C9 H9B 109.5(10) . . ?
N1 C9 H9A 108.1(10) . . ?
N1 C9 H9B 107.3(10) . . ?
N1 C9 C10 113.55(13) . . ?
C11 C10 C9 120.69(14) . . ?
C15 C10 C9 120.57(14) . . ?
C15 C10 C11 118.70(14) . . ?
C10 C11 H11 120.1(10) . . ?
C12 C11 C10 121.19(15) . . ?
C12 C11 H11 118.7(10) . . ?
C11 C12 H12 122.4(11) . . ?
C13 C12 C11 118.15(16) . . ?
C13 C12 H12 119.4(11) . . ?
C14 C13 C12 122.74(15) . . ?
F1 C13 C12 118.51(15) . . ?
F1 C13 C14 118.75(15) . . ?
C13 C14 H14 119.8(11) . . ?
C13 C14 C15 118.53(15) . . ?
C15 C14 H14 121.7(11) . . ?
C10 C15 H15 118.1(10) . . ?
C14 C15 C10 120.68(15) . . ?
C14 C15 H15 121.2(10) . . ?
C1 N1 C8 126.67(13) . . ?
C1 N1 C9 118.12(13) . . ?
C8 N1 C9 115.13(12) . . ?
C5 N2 H2 117.5(13) . . ?
C6 N2 C5 122.67(15) . . ?
C6 N2 H2 118.7(13) . . ?
N3 C16 C17 120.41(13) . . ?
O3 C16 C17 119.07(14) . . ?
O3 C16 N3 120.51(14) . . ?
C16 C17 H17A 113.1(10) . . ?
C16 C17 H17B 106.5(10) . . ?
C16 C17 C18 112.04(13) . . ?
H17A C17 H17B 105.5(14) . . ?
C18 C17 H17A 111.3(10) . . ?
C18 C17 H17B 107.9(10) . . ?
C17 C18 H18A 106.9(10) . . ?
C17 C18 H18B 107.9(11) . . ?
H18A C18 H18B 107.4(15) . . ?
C19 C18 C17 116.95(14) . . ?
C19 C18 H18A 109.3(10) . . ?
C19 C18 H18B 108.0(11) . . ?
C18 C19 H19A 107.6(10) . . ?
C18 C19 H19B 110.1(10) . . ?
C18 C19 C20 116.41(15) . . ?
H19A C19 H19B 106.6(15) . . ?
C20 C19 H19A 107.4(10) . . ?
C20 C19 H19B 108.3(11) . . ?
C19 C20 H20A 111.7(11) . . ?
C19 C20 H20B 107.7(11) . . ?
H20A C20 H20B 110.0(14) . . ?
N4 C20 C19 112.39(13) . . ?
N4 C20 H20A 106.1(11) . . ?
N4 C20 H20B 109.0(11) . . ?
N4 C21 C22 116.09(14) . . ?
O4 C21 C22 121.76(15) . . ?
O4 C21 N4 122.07(15) . . ?
C21 C22 H22A 106.7(10) . . ?
C21 C22 H22B 110.3(11) . . ?
C21 C22 C23 111.29(13) . . ?
H22A C22 H22B 108.5(15) . . ?
C23 C22 H22A 112.3(10) . . ?
C23 C22 H22B 107.6(11) . . ?
C22 C23 H23A 110.3(10) . . ?
C22 C23 H23B 110.9(10) . . ?
H23A C23 H23B 105.2(14) . . ?
N3 C23 C22 112.47(13) . . ?
N3 C23 H23A 110.7(10) . . ?
N3 C23 H23B 107.0(10) . . ?
H24A C24 H24B 109.6(14) . . ?
C25 C24 H24A 107.0(10) . . ?
C25 C24 H24B 109.8(9) . . ?
N3 C24 H24A 109.6(10) . . ?
N3 C24 H24B 106.8(10) . . ?
N3 C24 C25 114.06(13) . . ?
C26 C25 C24 123.48(14) . . ?
C26 C25 C30 118.45(14) . . ?
C30 C25 C24 118.07(14) . . ?
C25 C26 H26 120.0(11) . . ?
C25 C26 C27 121.83(15) . . ?
C27 C26 H26 118.2(11) . . ?
C26 C27 H27 122.4(11) . . ?
C28 C27 C26 117.60(16) . . ?
C28 C27 H27 120.0(11) . . ?
C29 C28 C27 122.87(15) . . ?
F2 C28 C27 118.34(15) . . ?
F2 C28 C29 118.79(15) . . ?
C28 C29 H29 118.9(12) . . ?
C28 C29 C30 118.50(16) . . ?
C30 C29 H29 122.6(12) . . ?
C25 C30 H30 118.6(11) . . ?
C29 C30 C25 120.73(16) . . ?
C29 C30 H30 120.7(11) . . ?
C16 N3 C23 127.12(13) . . ?
C16 N3 C24 117.42(13) . . ?
C23 N3 C24 115.43(12) . . ?
C20 N4 H4 117.1(11) . . ?
C21 N4 C20 121.00(14) . . ?
C21 N4 H4 119.1(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
_geom_hbond_publ_flag
N2 H2 O4 0.87(2) 2.00(2) 2.8657(19) 171.5(18) . yes
N4 H4 O2 0.878(18) 2.106(19) 2.9784(18) 172.2(16) 1_455 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
C1 C2 C3 C4 -56.39(19) . . . . ?
C2 C1 N1 C8 -1.9(2) . . . . ?
C2 C1 N1 C9 -178.42(13) . . . . ?
C2 C3 C4 C5 -66.91(19) . . . . ?
C3 C4 C5 N2 64.8(2) . . . . ?
C4 C5 N2 C6 68.8(2) . . . . ?
C6 C7 C8 N1 47.82(18) . . . . ?
C7 C6 N2 C5 -162.04(14) . . . . ?
C7 C8 N1 C1 -103.13(17) . . . . ?
C7 C8 N1 C9 73.49(16) . . . . ?
C9 C10 C11 C12 177.67(15) . . . . ?
C9 C10 C15 C14 -177.94(15) . . . . ?
C10 C9 N1 C1 -97.00(16) . . . . ?
C10 C9 N1 C8 86.08(16) . . . . ?
C10 C11 C12 C13 0.6(2) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C11 C12 C13 F1 178.76(14) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C10 0.0(3) . . . . ?
C15 C10 C11 C12 0.1(2) . . . . ?
F1 C13 C14 C15 -179.02(15) . . . . ?
N1 C1 C2 C3 129.59(15) . . . . ?
N1 C9 C10 C11 68.82(19) . . . . ?
N1 C9 C10 C15 -113.61(16) . . . . ?
N2 C6 C7 C8 65.68(18) . . . . ?
O1 C1 C2 C3 -51.39(19) . . . . ?
O1 C1 N1 C8 179.10(14) . . . . ?
O1 C1 N1 C9 2.6(2) . . . . ?
O2 C6 C7 C8 -110.39(17) . . . . ?
O2 C6 N2 C5 14.0(2) . . . . ?
C16 C17 C18 C19 -61.18(19) . . . . ?
C17 C16 N3 C23 -0.9(2) . . . . ?
C17 C16 N3 C24 177.02(13) . . . . ?
C17 C18 C19 C20 -65.66(19) . . . . ?
C18 C19 C20 N4 68.34(19) . . . . ?
C19 C20 N4 C21 65.5(2) . . . . ?
C21 C22 C23 N3 54.72(17) . . . . ?
C22 C21 N4 C20 -160.93(14) . . . . ?
C22 C23 N3 C16 -104.03(17) . . . . ?
C22 C23 N3 C24 78.01(16) . . . . ?
C24 C25 C26 C27 178.33(16) . . . . ?
C24 C25 C30 C29 -178.08(17) . . . . ?
C25 C24 N3 C16 -82.58(17) . . . . ?
C25 C24 N3 C23 95.59(16) . . . . ?
C25 C26 C27 C28 -0.2(3) . . . . ?
C26 C25 C30 C29 1.3(3) . . . . ?
C26 C27 C28 C29 1.2(3) . . . . ?
C26 C27 C28 F2 -178.53(15) . . . . ?
C27 C28 C29 C30 -1.0(3) . . . . ?
C28 C29 C30 C25 -0.4(3) . . . . ?
C30 C25 C26 C27 -1.0(3) . . . . ?
F2 C28 C29 C30 178.80(17) . . . . ?
N3 C16 C17 C18 126.47(15) . . . . ?
N3 C24 C25 C26 -5.7(2) . . . . ?
N3 C24 C25 C30 173.68(14) . . . . ?
N4 C21 C22 C23 59.50(18) . . . . ?
O3 C16 C17 C18 -54.54(19) . . . . ?
O3 C16 N3 C23 -179.87(14) . . . . ?
O3 C16 N3 C24 -1.9(2) . . . . ?
O4 C21 C22 C23 -117.35(17) . . . . ?
O4 C21 N4 C20 15.9(2) . . . . ?


_olex2_date_sample_data_collection 2021-03-01
_olex2_date_sample_submission    2021-02-25
_olex2_exptl_crystal_mounting_method 'oil on 200 micrometre micromount'
_olex2_submission_original_sample_id KP439_C
_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 1.458
_oxdiff_exptl_absorpt_empirical_full_min 0.802
