# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_hpd718_auto
_database_code_depnum_ccdc_archive 'CCDC 2285394'
loop_
_audit_author_name
_audit_author_address
'Hadi Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2023-07-29 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;
_audit_creation_date             2023-06-02
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 F3 O3'
_chemical_formula_sum            'C14 H11 F3 O3'
_chemical_formula_weight         284.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     SB2-167A
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1427(3)
_cell_length_b                   9.1744(4)
_cell_length_c                   9.7896(4)
_cell_angle_alpha                97.571(3)
_cell_angle_beta                 107.127(4)
_cell_angle_gamma                95.412(4)
_cell_volume                     601.69(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6959
_cell_measurement_temperature    100.01(11)
_cell_measurement_theta_max      75.7210
_cell_measurement_theta_min      4.7990
_shelx_estimated_absorpt_T_max   0.897
_shelx_estimated_absorpt_T_min   0.868
_exptl_absorpt_coefficient_mu    1.220
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.649
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
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 dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -2 -5 0.0460
2 -2 -6 0.0515
-2 6 -2 0.0646
-2 1 6 0.0397
2 -6 1 0.0206
-1 -1 -5 0.0513
-4 -2 -1 0.0418
-1 0 6 0.0363
4 2 -2 0.0556

_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.091
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
2.1518 -2.4762 -5.2959 -0.1009 -0.4275 0.8984
1.9920 -1.8040 -5.7062 -0.0726 -0.3103 0.9479
-1.6561 5.5055 -1.8467 0.2311 0.9588 0.1650
-1.6973 0.7656 6.1313 0.0289 0.1294 -0.9912
1.9355 -5.5862 0.7630 -0.2339 -0.9722 0.0089
-0.9683 -1.1703 -5.0965 0.5379 -0.1313 0.8327
-3.6494 -2.0393 -0.8132 0.9580 -0.2309 0.1702
-0.5844 0.4755 6.0913 -0.2082 0.0524 -0.9767
4.2205 1.9258 -2.4151 -0.9129 0.2188 0.3447

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9968
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.802
_diffrn_reflns_theta_min         4.795
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 111.00   0.50    0.60    --  106.29-125.00 150.00  150
  2  ω     36.00 111.00   0.50    0.60    --  106.29-125.00 120.00  150
  3  ω     33.00 105.00   0.50    0.60    --  106.29 -94.00   0.00  144
  4  ω     33.00 105.00   0.50    0.60    --  106.29 -94.00 120.00  144
  5  ω     36.00 111.00   0.50    0.60    --  106.29-125.00 -30.00  150
  6  ω     33.00 105.00   0.50    0.60    --  106.29 -94.00 -60.00  144
  7  ω     33.00 105.00   0.50    0.60    --  106.29 -94.00-180.00  144
  8  ω     33.00 101.00   0.50    0.60    --  106.29 -77.00-180.00  136
  9  ω     33.00  71.00   0.50    0.60    --  106.29 -61.00-120.00   76
 10  ω    -26.00  62.00   0.50    0.15    --   45.90 -57.00-120.00  176
 11  ω     33.00  71.00   0.50    0.60    --  106.29 -61.00 120.00   76
 12  ω    -29.00  33.00   0.50    0.15    --   45.90 -24.00 105.00  124
 13  ω     92.00 178.00   0.50    0.60    --  106.29  24.00 -90.00  172
 14  ω     31.00 120.00   0.50    0.15    --   45.90  37.00 -60.00  178
 15  ω     31.00 120.00   0.50    0.15    --   45.90  37.00   0.00  178
 16  ω     32.00 122.00   0.50    0.15    --   45.90  24.00 -90.00  180
 17  ω     31.00 120.00   0.50    0.15    --   45.90  37.00-120.00  178
 18  ω     31.00 120.00   0.50    0.15    --   45.90  37.00-150.00  178
 19  ω     31.00 120.00   0.50    0.15    --   45.90  37.00-180.00  178
 20  ω    -43.00  28.00   0.50    0.15    --  -45.90  37.00 -60.00  142
 21  ω    -33.00  30.00   0.50    0.15    --  -45.90  24.00 -90.00  126
 22  ω    -30.00  30.00   0.50    0.15    --  -45.90  19.00  60.00  120
 23  ω    -51.00 -19.00   0.50    0.60    --  -91.75  45.00 150.00   64
 24  ω   -101.00 -19.00   0.50    0.60    --  -91.75  77.00  60.00  164
 25  ω    -71.00 -19.00   0.50    0.60    --  -91.75  61.00 -30.00  104
 26  ω    -51.00 -19.00   0.50    0.60    --  -91.75  45.00 -30.00   64
 27  ω    -51.00 -19.00   0.50    0.60    --  -91.75  45.00 -90.00   64
 28  ω    -51.00 -19.00   0.50    0.60    --  -91.75  45.00-180.00   64
 29  ω    -51.00 -19.00   0.50    0.60    --  -91.75  45.00-120.00   64
 30  ω    -51.00 -19.00   0.50    0.60    --  -91.75  45.00  90.00   64
 31  ω    -85.00 -22.00   0.50    0.60    --  -91.75 125.00 150.00  126
 32  ω   -122.00 -31.00   0.50    0.15    --  -45.90 -24.00 105.00  182
 33  ω   -120.00 -31.00   0.50    0.15    --  -45.90 -37.00  30.00  178
 34  ω   -120.00 -31.00   0.50    0.15    --  -45.90 -37.00 -30.00  178
 35  ω   -120.00 -31.00   0.50    0.15    --  -45.90 -37.00 -90.00  178
 36  ω   -164.00 -77.00   0.50    0.60    --  -91.75 -45.00   0.00  174
 37  ω   -164.00 -77.00   0.50    0.60    --  -91.75 -45.00  60.00  174
 38  ω   -167.00 -77.00   0.50    0.60    --  -91.75 -24.00 105.00  180
 39  ω   -164.00-100.00   0.50    0.60    --  -91.75 -94.00 -90.00  128
 40  ω   -164.00-100.00   0.50    0.60    --  -91.75 -94.00-120.00  128
 41  ω   -164.00-100.00   0.50    0.60    --  -91.75 -94.00-150.00  128
;
_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      -0.2263709000
_diffrn_orient_matrix_UB_12      -0.0437319000
_diffrn_orient_matrix_UB_13      -0.0524841000
_diffrn_orient_matrix_UB_21      -0.0267797000
_diffrn_orient_matrix_UB_22      0.1638379000
_diffrn_orient_matrix_UB_23      -0.0067646000
_diffrn_orient_matrix_UB_31      0.0013897000
_diffrn_orient_matrix_UB_32      -0.0227552000
_diffrn_orient_matrix_UB_33      -0.1584312000
_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                2023
_reflns_number_total             2315
_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 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.056
_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)+(0.0625P)²+0.1901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1034
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H7 of C7, H5 of C5, H6 of C6, H4 of C4, H1A of C1
 At 1.5 times of:
  All C(H,H,H) groups, H1 of C12
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1A), C7(H7), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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
F3 F 0.42414(12) 0.24668(10) 0.08987(9) 0.0281(2) Uani 1 1 d . . . . .
F2 F 0.71335(13) 0.30098(11) 0.07302(9) 0.0308(2) Uani 1 1 d . . . . .
F1 F 0.65235(15) 0.11530(10) 0.17494(10) 0.0351(3) Uani 1 1 d . . . . .
O3 O 0.91808(15) 0.19911(11) 0.69283(10) 0.0229(2) Uani 1 1 d . . . . .
O1 O 0.87135(15) 0.57863(11) 0.78297(11) 0.0232(2) Uani 1 1 d . . . . .
O2 O 1.00049(16) 0.35283(11) 0.90666(10) 0.0251(3) Uani 1 1 d . . . . .
C2 C 0.7868(2) 0.44330(15) 0.54887(15) 0.0200(3) Uani 1 1 d . . . . .
C9 C 0.6758(2) 0.35466(16) 0.30497(15) 0.0211(3) Uani 1 1 d . . . . .
C10 C 0.8594(2) 0.45086(15) 0.69461(15) 0.0202(3) Uani 1 1 d . . . . .
C11 C 0.9331(2) 0.32879(15) 0.77572(15) 0.0202(3) Uani 1 1 d . . . . .
C4 C 0.7164(2) 0.71485(16) 0.52442(15) 0.0226(3) Uani 1 1 d . . . . .
H4 H 0.761778 0.752562 0.625428 0.027 Uiso 1 1 calc R U . . .
C3 C 0.7199(2) 0.56698(16) 0.47353(15) 0.0206(3) Uani 1 1 d . . . . .
C1 C 0.7557(2) 0.31468(16) 0.43529(15) 0.0214(3) Uani 1 1 d . . . . .
H1A H 0.786682 0.218515 0.450716 0.026 Uiso 1 1 calc R U . . .
C7 C 0.5803(2) 0.60397(16) 0.22395(16) 0.0231(3) Uani 1 1 d . . . . .
H7 H 0.534343 0.566729 0.122851 0.028 Uiso 1 1 calc R U . . .
C14 C 0.6177(2) 0.25495(16) 0.16266(15) 0.0227(3) Uani 1 1 d . . . . .
C8 C 0.6517(2) 0.51198(16) 0.32297(15) 0.0204(3) Uani 1 1 d . . . . .
C6 C 0.5774(2) 0.75218(17) 0.27581(16) 0.0249(3) Uani 1 1 d . . . . .
H6 H 0.528811 0.816789 0.209348 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6448(2) 0.80690(16) 0.42404(16) 0.0248(3) Uani 1 1 d . . . . .
H5 H 0.642056 0.908499 0.457260 0.030 Uiso 1 1 calc R U . . .
C13 C 0.8348(2) 0.00924(17) 0.82652(16) 0.0268(3) Uani 1 1 d . . . . .
H13A H 0.709067 -0.018832 0.748085 0.040 Uiso 1 1 calc R U . . .
H13B H 0.817156 0.081042 0.903643 0.040 Uiso 1 1 calc R U . . .
H13C H 0.877761 -0.079311 0.865599 0.040 Uiso 1 1 calc R U . . .
C12 C 0.9890(2) 0.07810(16) 0.76850(16) 0.0240(3) Uani 1 1 d . . . . .
H12A H 1.111447 0.116845 0.849609 0.029 Uiso 1 1 calc R U . . .
H12B H 1.020829 0.001500 0.700891 0.029 Uiso 1 1 calc R U . . .
H1 H 0.921(3) 0.563(2) 0.874(2) 0.036 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3 C14 1.3457(17) . ?
F2 C14 1.3458(17) . ?
F1 C14 1.3416(17) . ?
O3 C11 1.3250(17) . ?
O3 C12 1.4627(17) . ?
O1 C10 1.3417(17) . ?
O2 C11 1.2106(17) . ?
C2 C10 1.357(2) . ?
C2 C3 1.4747(19) . ?
C2 C1 1.4620(19) . ?
C9 C1 1.350(2) . ?
C9 C14 1.4838(19) . ?
C9 C8 1.4634(19) . ?
C10 C11 1.504(2) . ?
C4 C3 1.387(2) . ?
C4 C5 1.394(2) . ?
C3 C8 1.414(2) . ?
C7 C8 1.385(2) . ?
C7 C6 1.392(2) . ?
C6 C5 1.393(2) . ?
C13 C12 1.505(2) . ?

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
C11 O3 C12 116.11(11) . . ?
C10 C2 C3 125.68(13) . . ?
C10 C2 C1 128.29(13) . . ?
C1 C2 C3 106.03(12) . . ?
C1 C9 C14 125.65(13) . . ?
C1 C9 C8 110.30(12) . . ?
C8 C9 C14 124.04(13) . . ?
O1 C10 C2 119.83(13) . . ?
O1 C10 C11 112.72(12) . . ?
C2 C10 C11 127.45(13) . . ?
O3 C11 C10 114.78(12) . . ?
O2 C11 O3 124.91(13) . . ?
O2 C11 C10 120.32(12) . . ?
C3 C4 C5 118.54(13) . . ?
C4 C3 C2 132.02(13) . . ?
C4 C3 C8 120.25(13) . . ?
C8 C3 C2 107.72(12) . . ?
C9 C1 C2 108.98(13) . . ?
C8 C7 C6 118.54(13) . . ?
F3 C14 F2 105.18(11) . . ?
F3 C14 C9 112.36(12) . . ?
F2 C14 C9 112.77(12) . . ?
F1 C14 F3 106.54(12) . . ?
F1 C14 F2 106.73(11) . . ?
F1 C14 C9 112.71(12) . . ?
C3 C8 C9 106.96(12) . . ?
C7 C8 C9 132.17(13) . . ?
C7 C8 C3 120.88(13) . . ?
C7 C6 C5 120.77(13) . . ?
C6 C5 C4 121.02(13) . . ?
O3 C12 C13 110.74(12) . . ?

_olex2_exptl_crystal_mounting_method 'nylo loop'
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.737
####################################################################### 
# 
# 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_hpd630b2
_database_code_depnum_ccdc_archive 'CCDC 2285395'
loop_
_audit_author_name
_audit_author_address
'Hadi Arman'
;University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2023-07-29 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;
_audit_creation_date             2023-07-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N5 O4'
_chemical_formula_sum            'C20 H17 N5 O4'
_chemical_formula_weight         391.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'SB2-104B try 2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.4348(2)
_cell_length_b                   9.9373(2)
_cell_length_c                   18.8362(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.256(2)
_cell_angle_gamma                90
_cell_volume                     1927.76(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8976
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.4380
_cell_measurement_theta_min      4.5540
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.834
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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 dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -5 -8 0.0927
-6 1 -4 0.0546
0 5 8 0.0542
6 -1 4 0.0228
6 -1 -8 0.0637
-5 0 9 0.0199
1 5 -6 0.0906

_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.082
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
0.7652 -4.7790 -8.2136 0.6532 -0.1589 0.7404
-5.8005 1.3297 -4.0265 0.7606 -0.1816 -0.6233
-0.2857 4.6297 8.4717 -0.7096 0.1723 -0.6832
5.7315 -1.0681 4.4456 -0.7918 0.1892 0.5807
5.5845 -0.9886 -8.1961 0.1478 0.6218 0.7691
-5.4689 0.0751 8.7064 -0.1732 -0.7263 -0.6652
1.4279 5.4273 -6.4211 0.2188 0.9057 -0.3631

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18614
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.362
_diffrn_reflns_theta_min         4.561
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  71.00   0.50    1.45    --  106.29 -61.00  60.00   76
  2  ω     33.00  71.00   0.50    1.45    --  106.29 -61.00 150.00   76
  3  ω     92.00 178.00   0.50    1.45    --  106.29  45.00  90.00  172
  4  ω     90.00 178.00   0.50    1.45    --  106.29  59.00 172.00  176
  5  ω     30.00 120.00   0.50    0.36    --   46.90  59.00 172.00  180
  6  ω     33.00  68.00   0.50    1.45    --  106.29 -59.00  32.00   70
  7  ω     33.00  65.00   0.50    1.45    --  106.29 -61.00   0.00   64
  8  ω    -25.00  64.00   0.50    0.36    --   46.90 -59.00  32.00  178
  9  ω     35.00  61.00   0.50    1.45    --  106.29 -61.00-180.00   52
 10  ω     33.00 105.00   0.50    1.45    --  106.29 -94.00 -30.00  144
 11  ω    -63.00  26.00   0.50    0.36    --  -46.90  59.00 172.00  178
 12  ω    -68.00 -19.00   0.50    1.45    --  -91.75  59.00 172.00   98
 13  ω    -71.00 -19.00   0.50    1.45    --  -91.75  61.00 120.00  104
 14  ω    -71.00 -19.00   0.50    1.45    --  -91.75  61.00  30.00  104
 15  ω    -51.00 -19.00   0.50    1.45    --  -91.75  45.00  30.00   64
 16  ω    -51.00 -19.00   0.50    1.45    --  -91.75  45.00   0.00   64
 17  ω    -51.00 -19.00   0.50    1.45    --  -91.75  45.00 -60.00   64
 18  ω    -51.00 -19.00   0.50    1.45    --  -91.75  45.00 -90.00   64
 19  ω    -51.00 -19.00   0.50    1.45    --  -91.75  45.00 150.00   64
 20  ω   -164.00 -91.00   0.50    1.45    --  -91.75 -61.00 120.00  146
 21  ω   -164.00-100.00   0.50    1.45    --  -91.75 -94.00 150.00  128
 22  ω   -164.00 -75.00   0.50    1.45    --  -91.75 -59.00  32.00  178
 23  ω   -119.00 -30.00   0.50    0.36    --  -46.90 -59.00  32.00  178
 24  ω   -119.00 -87.00   0.50    0.36    --  -46.90-125.00-150.00   64
 25  ω   -119.00 -87.00   0.50    0.36    --  -46.90-125.00-180.00   64
;
_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      -0.0856504000
_diffrn_orient_matrix_UB_12      -0.0240940000
_diffrn_orient_matrix_UB_13      -0.0734819000
_diffrn_orient_matrix_UB_21      0.0793563000
_diffrn_orient_matrix_UB_22      0.1052097000
_diffrn_orient_matrix_UB_23      -0.0344811000
_diffrn_orient_matrix_UB_31      0.0935328000
_diffrn_orient_matrix_UB_32      -0.1112539000
_diffrn_orient_matrix_UB_33      -0.0166933000
_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                3170
_reflns_number_total             3713
_reflns_odcompleteness_completeness 99.92
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3713
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.035
_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)+(0.0519P)²+0.7248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1231
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N5-O1B
 1.2 with sigma of 0.02
3. Others
 Fixed Sof: O1A(0.85) O1B(0.15)
4.a Ternary CH refined with riding coordinates:
 C4(H4)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C9(H9), C13(H13), C16(H16), C12(H12), C11(H11), C10(H10), C19(H19),
 C18(H18), C17(H17)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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
O3 O 0.04124(14) 0.53158(13) 0.17736(6) 0.0572(4) Uani 1 1 d . . . . .
O4 O 0.55222(13) 0.65005(14) 0.46397(6) 0.0562(3) Uani 1 1 d . . . . .
O2 O 0.08897(13) 0.31955(13) 0.21377(7) 0.0546(3) Uani 1 1 d . . . . .
N1 N 0.24529(13) 0.64430(13) 0.36881(7) 0.0405(3) Uani 1 1 d . . . . .
N2 N 0.17437(13) 0.62582(13) 0.30076(7) 0.0405(3) Uani 1 1 d . . . . .
N3 N 0.34359(14) 0.33310(14) 0.32777(8) 0.0448(3) Uani 1 1 d . . . . .
N4 N 0.45628(14) 0.40490(14) 0.33659(7) 0.0448(3) Uani 1 1 d . . . . .
C1 C 0.16911(15) 0.49910(15) 0.28921(8) 0.0368(3) Uani 1 1 d . . . . .
C4 C 0.31275(15) 0.52171(15) 0.39763(8) 0.0377(3) Uani 1 1 d . . . . .
H4 H 0.312379 0.508764 0.449174 0.045 Uiso 1 1 calc R U . . .
C2 C 0.23770(15) 0.41059(15) 0.34995(8) 0.0368(3) Uani 1 1 d . . . . .
C3 C 0.44615(15) 0.50811(16) 0.37663(8) 0.0395(4) Uani 1 1 d . . . . .
C14 C 0.55551(16) 0.59730(17) 0.40561(8) 0.0420(4) Uani 1 1 d . . . . .
C5 C 0.09565(16) 0.43888(17) 0.22235(8) 0.0412(4) Uani 1 1 d . . . . .
C8 C 0.14078(17) 0.32817(17) 0.38342(8) 0.0425(4) Uani 1 1 d . . . . .
C15 C 0.66134(16) 0.62718(18) 0.36401(9) 0.0455(4) Uani 1 1 d . . . . .
C20 C 0.77261(18) 0.6904(2) 0.39926(12) 0.0589(5) Uani 1 1 d . . . . .
H20 H 0.783234 0.703769 0.448724 0.071 Uiso 1 1 calc R U . . .
C9 C 0.1542(2) 0.19205(19) 0.39430(11) 0.0594(5) Uani 1 1 d . . . . .
H9 H 0.224968 0.146744 0.381431 0.071 Uiso 1 1 calc R U . . .
C13 C 0.0346(2) 0.3927(2) 0.40363(12) 0.0619(5) Uani 1 1 d . . . . .
H13 H 0.024338 0.484896 0.396375 0.074 Uiso 1 1 calc R U . . .
C16 C 0.6481(2) 0.6076(3) 0.29037(11) 0.0674(6) Uani 1 1 d . . . . .
H16 H 0.574943 0.564465 0.266002 0.081 Uiso 1 1 calc R U . . .
C6 C -0.0408(3) 0.4819(2) 0.11216(11) 0.0737(6) Uani 1 1 d . . . . .
H6A H 0.008912 0.423135 0.085729 0.088 Uiso 1 1 calc R U . . .
H6B H -0.113515 0.431477 0.124664 0.088 Uiso 1 1 calc R U . . .
C12 C -0.0564(2) 0.3219(3) 0.43441(14) 0.0760(7) Uani 1 1 d . . . . .
H12 H -0.126941 0.366600 0.447916 0.091 Uiso 1 1 calc R U . . .
C11 C -0.0429(2) 0.1875(3) 0.44497(13) 0.0738(6) Uani 1 1 d . . . . .
H11 H -0.104035 0.140061 0.465852 0.089 Uiso 1 1 calc R U . . .
C10 C 0.0602(3) 0.1219(2) 0.42499(14) 0.0768(7) Uani 1 1 d . . . . .
H10 H 0.068383 0.029418 0.431793 0.092 Uiso 1 1 calc R U . . .
C19 C 0.8671(2) 0.7332(3) 0.36111(16) 0.0760(7) Uani 1 1 d . . . . .
H19 H 0.941386 0.774979 0.385084 0.091 Uiso 1 1 calc R U . . .
C18 C 0.8526(2) 0.7150(3) 0.28837(17) 0.0846(8) Uani 1 1 d . . . . .
H18 H 0.916298 0.745075 0.262871 0.101 Uiso 1 1 calc R U . . .
C17 C 0.7438(3) 0.6522(3) 0.25317(15) 0.0891(8) Uani 1 1 d . . . . .
H17 H 0.734251 0.639360 0.203690 0.107 Uiso 1 1 calc R U . . .
C7 C -0.0874(3) 0.5987(3) 0.06828(13) 0.0859(8) Uani 1 1 d . . . . .
H7A H -0.144639 0.569340 0.026041 0.129 Uiso 1 1 calc R U . . .
H7B H -0.014921 0.645525 0.054358 0.129 Uiso 1 1 calc R U . . .
H7C H -0.133426 0.657965 0.095619 0.129 Uiso 1 1 calc R U . . .
H3 H 0.336(3) 0.282(3) 0.2894(17) 0.103 Uiso 1 1 d . U . A 1
N5 N 0.25001(18) 0.75955(17) 0.40501(11) 0.0623(5) Uani 1 1 d D . . . .
O1A O 0.19330(18) 0.85263(17) 0.37389(11) 0.0700(5) Uani 0.85 1 d . . P . .
O1B O 0.2758(12) 0.7727(12) 0.4597(5) 0.081(3) Uani 0.15 1 d D . P . .


_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
O3 C5 1.317(2) . ?
O3 C6 1.465(2) . ?
O4 C14 1.223(2) . ?
O2 C5 1.197(2) . ?
N1 N2 1.3854(18) . ?
N1 C4 1.467(2) . ?
N1 N5 1.330(2) . ?
N2 C1 1.278(2) . ?
N3 N4 1.363(2) . ?
N3 C2 1.462(2) . ?
N3 H3 0.87(3) . ?
N4 C3 1.288(2) . ?
C1 C2 1.527(2) . ?
C1 C5 1.490(2) . ?
C4 H4 0.9800 . ?
C4 C2 1.553(2) . ?
C4 C3 1.513(2) . ?
C2 C8 1.515(2) . ?
C3 C14 1.478(2) . ?
C14 C15 1.483(2) . ?
C8 C9 1.372(3) . ?
C8 C13 1.386(3) . ?
C15 C20 1.391(3) . ?
C15 C16 1.385(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.377(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.401(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.381(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.462(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.354(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.362(4) . ?
C10 H10 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.366(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.369(4) . ?
C17 H17 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
N5 O1A 1.199(2) . ?
N5 O1B 1.030(9) . ?

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
C5 O3 C6 115.93(15) . . ?
N2 N1 C4 112.67(12) . . ?
N5 N1 N2 123.97(15) . . ?
N5 N1 C4 123.34(15) . . ?
C1 N2 N1 106.86(13) . . ?
N4 N3 C2 111.50(13) . . ?
N4 N3 H3 111(2) . . ?
C2 N3 H3 125(2) . . ?
C3 N4 N3 109.76(14) . . ?
N2 C1 C2 115.99(14) . . ?
N2 C1 C5 122.81(14) . . ?
C5 C1 C2 121.14(13) . . ?
N1 C4 H4 113.4 . . ?
N1 C4 C2 102.07(12) . . ?
N1 C4 C3 112.60(13) . . ?
C2 C4 H4 113.4 . . ?
C3 C4 H4 113.4 . . ?
C3 C4 C2 100.65(12) . . ?
N3 C2 C1 111.97(12) . . ?
N3 C2 C4 101.88(12) . . ?
N3 C2 C8 114.83(13) . . ?
C1 C2 C4 98.95(12) . . ?
C8 C2 C1 111.06(13) . . ?
C8 C2 C4 116.85(12) . . ?
N4 C3 C4 112.95(14) . . ?
N4 C3 C14 124.24(15) . . ?
C14 C3 C4 122.55(14) . . ?
O4 C14 C3 117.20(15) . . ?
O4 C14 C15 121.32(16) . . ?
C3 C14 C15 121.41(14) . . ?
O3 C5 C1 111.89(14) . . ?
O2 C5 O3 126.59(16) . . ?
O2 C5 C1 121.51(15) . . ?
C9 C8 C2 122.43(16) . . ?
C9 C8 C13 118.81(17) . . ?
C13 C8 C2 118.76(15) . . ?
C20 C15 C14 118.25(16) . . ?
C16 C15 C14 122.56(17) . . ?
C16 C15 C20 118.83(18) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.2(2) . . ?
C19 C20 H20 119.9 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.9(2) . . ?
C12 C13 H13 119.6 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
O3 C6 H6A 110.2 . . ?
O3 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C7 C6 O3 107.65(19) . . ?
C7 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 119.9 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C20 C19 H19 119.7 . . ?
C18 C19 C20 120.6(2) . . ?
C18 C19 H19 119.7 . . ?
C19 C18 H18 120.2 . . ?
C19 C18 C17 119.7(2) . . ?
C17 C18 H18 120.2 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.6 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1A N5 N1 116.0(2) . . ?
O1B N5 N1 127.2(7) . . ?
O1B N5 O1A 114.8(7) . . ?

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
O4 C14 C15 C20 15.1(3) . . . . ?
O4 C14 C15 C16 -158.0(2) . . . . ?
N1 N2 C1 C2 0.18(18) . . . . ?
N1 N2 C1 C5 177.33(13) . . . . ?
N1 C4 C2 N3 131.06(12) . . . . ?
N1 C4 C2 C1 16.21(14) . . . . ?
N1 C4 C2 C8 -102.97(15) . . . . ?
N1 C4 C3 N4 -116.15(15) . . . . ?
N1 C4 C3 C14 69.53(18) . . . . ?
N2 N1 C4 C2 -18.75(16) . . . . ?
N2 N1 C4 C3 88.33(15) . . . . ?
N2 N1 N5 O1A -3.6(3) . . . . ?
N2 N1 N5 O1B 159.5(9) . . . . ?
N2 C1 C2 N3 -117.90(15) . . . . ?
N2 C1 C2 C4 -11.15(17) . . . . ?
N2 C1 C2 C8 112.26(16) . . . . ?
N2 C1 C5 O3 1.5(2) . . . . ?
N2 C1 C5 O2 -177.71(16) . . . . ?
N3 N4 C3 C4 -3.13(19) . . . . ?
N3 N4 C3 C14 171.07(14) . . . . ?
N3 C2 C8 C9 2.2(2) . . . . ?
N3 C2 C8 C13 -177.67(16) . . . . ?
N4 N3 C2 C1 86.28(16) . . . . ?
N4 N3 C2 C4 -18.58(16) . . . . ?
N4 N3 C2 C8 -145.87(14) . . . . ?
N4 C3 C14 O4 -148.57(17) . . . . ?
N4 C3 C14 C15 34.5(2) . . . . ?
C1 C2 C8 C9 130.50(17) . . . . ?
C1 C2 C8 C13 -49.4(2) . . . . ?
C4 N1 N2 C1 12.37(17) . . . . ?
C4 N1 N5 O1A 177.83(17) . . . . ?
C4 N1 N5 O1B -19.1(9) . . . . ?
C4 C2 C8 C9 -117.05(18) . . . . ?
C4 C2 C8 C13 63.1(2) . . . . ?
C4 C3 C14 O4 25.1(2) . . . . ?
C4 C3 C14 C15 -151.84(15) . . . . ?
C2 N3 N4 C3 14.44(18) . . . . ?
C2 C1 C5 O3 178.56(14) . . . . ?
C2 C1 C5 O2 -0.7(2) . . . . ?
C2 C4 C3 N4 -8.17(17) . . . . ?
C2 C4 C3 C14 177.52(14) . . . . ?
C2 C8 C9 C10 -179.46(18) . . . . ?
C2 C8 C13 C12 -179.94(19) . . . . ?
C3 C4 C2 N3 14.94(14) . . . . ?
C3 C4 C2 C1 -99.90(13) . . . . ?
C3 C4 C2 C8 140.92(13) . . . . ?
C3 C14 C15 C20 -168.10(16) . . . . ?
C3 C14 C15 C16 18.8(3) . . . . ?
C14 C15 C20 C19 -172.90(19) . . . . ?
C14 C15 C16 C17 172.2(2) . . . . ?
C5 O3 C6 C7 -177.76(19) . . . . ?
C5 C1 C2 N3 64.89(18) . . . . ?
C5 C1 C2 C4 171.64(13) . . . . ?
C5 C1 C2 C8 -64.95(18) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
C8 C13 C12 C11 -0.3(4) . . . . ?
C15 C20 C19 C18 0.3(4) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C20 C15 C16 C17 -0.8(3) . . . . ?
C20 C19 C18 C17 -0.7(4) . . . . ?
C9 C8 C13 C12 0.2(3) . . . . ?
C13 C8 C9 C10 0.4(3) . . . . ?
C13 C12 C11 C10 -0.2(4) . . . . ?
C16 C15 C20 C19 0.4(3) . . . . ?
C6 O3 C5 O2 3.3(3) . . . . ?
C6 O3 C5 C1 -175.89(16) . . . . ?
C12 C11 C10 C9 0.8(4) . . . . ?
C19 C18 C17 C16 0.3(5) . . . . ?
N5 N1 N2 C1 -166.33(15) . . . . ?
N5 N1 C4 C2 159.95(15) . . . . ?
N5 N1 C4 C3 -92.97(18) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_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 3.461
_oxdiff_exptl_absorpt_empirical_full_min 0.380
