# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20240202-cg-ys_auto
_database_code_depnum_ccdc_archive 'CCDC 2344191'
loop_
_audit_author_name
_audit_author_address
'xiongda xie'
;Sun Yat sen University
China
;
_audit_update_record             
;
2024-03-29 deposited with the CCDC.	2024-06-27 downloaded from the CCDC.
;
_audit_creation_date             2024-02-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H13 F2 N3 O3)'
_chemical_formula_sum            'C38 H26 F4 N6 O6'
_chemical_formula_weight         738.65
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   14.9260(4)
_cell_length_b                   6.5272(2)
_cell_length_c                   17.0520(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.776(2)
_cell_angle_gamma                90
_cell_volume                     1661.14(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11342
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      75.1040
_cell_measurement_theta_min      2.9110
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.789
_exptl_absorpt_coefficient_mu    0.998
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19916
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.031
_diffrn_reflns_theta_min         2.591
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00 -62.00   0.50    1.00    --  -44.96 140.00 -28.00   50
  2  ω    -92.00 -43.00   0.50    1.00    --  -44.96 130.00 158.00   98
  3  ω   -116.00 -72.00   0.50    1.00    --  -44.96-130.00  86.00   88
  4  ω   -117.00 -73.00   0.50    1.00    --  -44.96-140.00 -87.00   88
  5  ω     70.00  95.00   0.50    1.00    --   44.96 140.00 -28.00   50
  6  ω     41.00  66.00   0.50    1.00    --   44.96-140.00 -87.00   50
  7  ω     35.00  60.00   0.50    1.00    --   44.96-130.00  86.00   50
  8  ω   -142.00-117.00   0.50    2.00    -- -100.00-140.00 -87.00   50
  9  ω    -96.00 -71.00   0.50    2.00    -- -100.00 130.00 158.00   50
 10  ω   -121.00 -90.00   0.50    2.00    -- -100.00-130.00  86.00   62
 11  ω   -120.00 -28.00   0.50    2.00    -- -100.00 140.00 -28.00  184
 12  ω    102.00 127.00   0.50    2.00    --  105.85 130.00 158.00   50
 13  ω     84.00 122.00   0.50    2.00    --  105.85-140.00 -87.00   76
 14  ω     97.00 122.00   0.50    2.00    --  105.85 140.00 -28.00   50
 15  ω     71.00 109.00   0.50    2.00    --  105.85-130.00  86.00   76
 16  ω    -23.00  31.00   0.50    1.00    --  -44.96  19.00 -60.00  108
 17  ω    -20.00  33.00   0.50    1.00    --  -44.96  19.00 150.00  106
 18  ω     19.00 114.00   0.50    1.00    --   44.96  77.00  60.00  190
 19  ω    -24.00  45.00   0.50    1.00    --   44.96 -38.00  30.00  138
 20  ω   -170.00-124.00   0.50    2.00    -- -100.00 -77.00   0.00   92
 21  ω    -64.00 -26.00   0.50    2.00    -- -100.00  61.00-180.00   76
 22  ω   -174.00 -75.00   0.50    2.00    -- -100.00 -15.00-180.00  198
 23  ω   -114.00 -78.00   0.50    2.00    -- -100.00 -77.00   0.00   72
 24  ω   -108.00 -30.00   0.50    2.00    -- -100.00 110.00  60.09  156
 25  ω   -156.00-130.00   0.50    2.00    -- -100.00 -30.00 -30.00   52
 26  ω   -127.00 -82.00   0.50    2.00    -- -100.00 -30.00 -30.00   90
 27  ω     73.00 112.00   0.50    2.00    --  105.85-125.00-150.00   78
 28  ω     39.00  73.00   0.50    2.00    --  105.85 -61.00 120.00   68
 29  ω     88.00 174.00   0.50    2.00    --  105.85  30.00-150.00  172
 30  ω     73.00 112.00   0.50    2.00    --  105.85-125.00 -30.00   78
 31  ω     38.00 106.00   0.50    2.00    --  105.85 -77.00 -90.00  136
 32  ω     33.00  88.00   0.50    2.00    --  105.85 -77.00-120.00  110
 33  ω    105.00 131.00   0.50    2.00    --  105.85  77.00  60.00   52
 34  ω     36.00 107.00   0.50    2.00    --  105.85 -77.00-180.00  142
 35  ω     67.00 100.00   0.50    2.00    --  105.85 -77.00  60.00   66
 36  ω     80.00 106.00   0.50    2.00    --  105.85 -94.00 120.00   52
 37  ω     33.00  65.00   0.50    2.00    --  105.85 -61.00 -60.00   64
 38  ω     91.00 116.00   0.50    2.00    --  105.85  45.00  60.00   50
 39  ω    144.00 174.00   0.50    2.00    --  105.85  45.00  60.00   60
 40  ω     47.00  73.00   0.50    2.00    --  105.85 -94.00 120.00   52
 41  ω     49.00 112.00   0.50    2.00    --  105.85-125.00  30.00  126
 42  ω     98.00 158.00   0.50    2.00    --  105.85  30.00  90.00  120
 43  ω     95.00 174.00   0.50    2.00    --  105.85  61.00-120.00  158
 44  ω    148.00 177.00   0.50    2.00    --  105.85  77.00  60.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0526367000
_diffrn_orient_matrix_UB_12      -0.1250530000
_diffrn_orient_matrix_UB_13      -0.0618835000
_diffrn_orient_matrix_UB_21      -0.0297052000
_diffrn_orient_matrix_UB_22      0.2001130000
_diffrn_orient_matrix_UB_23      -0.0406219000
_diffrn_orient_matrix_UB_31      0.0836348000
_diffrn_orient_matrix_UB_32      -0.0075912000
_diffrn_orient_matrix_UB_33      -0.0518104000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.908
_reflns_number_gt                5678
_reflns_number_total             6494
_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 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 2233 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.13(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         6494
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.094
_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)+(0.0868P)²+0.1677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1268
_refine_ls_wR_factor_ref         0.1386
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C36(H36), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5A), N3(H3), C24(H24), C6(H6), C5(H5), C14(H14), C15(H15), C33(H33),
 C30(H30), C13(H13), C25(H25), C4(H4), C31(H31), C3(H3A), C22(H22), C32(H32),
 C12(H12), C26(H26), C2(H2A), C23(H23)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O2(H2)
;
_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 0.95326(14) 0.3492(3) 0.32872(12) 0.0276(5) Uani 1 1 d . . . . .
F2 F 1.03465(14) 0.0894(4) 0.29202(13) 0.0293(5) Uani 1 1 d . . . . .
F3 F 0.33199(15) 0.5275(4) 0.25272(13) 0.0293(5) Uani 1 1 d . . . . .
F4 F 0.37919(14) 0.7882(3) 0.18470(12) 0.0276(5) Uani 1 1 d . . . . .
O51 O 0.67656(18) 0.7541(5) 0.23702(16) 0.0298(6) Uani 1 1 d . . . . .
O1 O 0.70715(18) 0.2702(4) 0.17878(15) 0.0292(6) Uani 1 1 d . . . . .
O4 O 0.47733(19) 0.3005(4) 0.22801(16) 0.0281(6) Uani 1 1 d . . . . .
H4A H 0.5013 0.3198 0.2722 0.042 Uiso 1 1 calc R U . . .
O2 O 0.89278(19) -0.1566(4) 0.26693(16) 0.0289(6) Uani 1 1 d . . . . .
H2 H 0.8935 -0.1443 0.2179 0.043 Uiso 1 1 calc R U . . .
O3 O 0.5180(2) 0.4364(5) 0.36939(16) 0.0320(6) Uani 1 1 d . . . . .
O27 O 0.9132(2) -0.0385(4) 0.11984(16) 0.0326(6) Uani 1 1 d . . . . .
N1 N 0.7933(2) 0.1219(5) 0.27215(19) 0.0266(7) Uani 1 1 d . . . . .
N5 N 0.4359(2) 0.6643(6) 0.44121(19) 0.0295(7) Uani 1 1 d . . . . .
H5A H 0.4446 0.6088 0.4877 0.035 Uiso 1 1 calc R U . . .
N6 N 0.5587(2) 0.5837(5) 0.18317(19) 0.0248(7) Uani 1 1 d . . . . .
N4 N 0.6138(2) 1.0093(6) 0.4011(2) 0.0340(8) Uani 1 1 d . . . . .
N3 N 1.0300(2) 0.1693(6) 0.0846(2) 0.0319(8) Uani 1 1 d . . . . .
H3 H 1.0470 0.1011 0.0429 0.038 Uiso 1 1 calc R U . . .
N2 N 0.8480(2) 0.5056(6) 0.0422(2) 0.0363(8) Uani 1 1 d . . . . .
C38 C 0.5953(3) 0.7209(6) 0.2330(2) 0.0251(8) Uani 1 1 d . . . . .
C37 C 0.5784(3) 0.9432(6) 0.3466(2) 0.0275(8) Uani 1 1 d . . . . .
C1 C 0.8773(3) 0.0069(6) 0.3898(2) 0.0258(8) Uani 1 1 d . . . . .
C35 C 0.4704(3) 0.5893(6) 0.3750(2) 0.0261(8) Uani 1 1 d . . . . .
C24 C 0.3469(3) 0.3761(8) -0.0378(2) 0.0346(9) Uani 1 1 d . . . . .
H24 H 0.3172 0.3540 -0.0866 0.042 Uiso 1 1 calc R U . . .
C6 C 0.9238(3) -0.1546(7) 0.4239(2) 0.0292(8) Uani 1 1 d . . . . .
H6 H 0.9519 -0.2533 0.3915 0.035 Uiso 1 1 calc R U . . .
C34 C 0.3841(2) 0.8420(6) 0.4282(2) 0.0271(8) Uani 1 1 d . . . . .
C8 C 0.9553(2) 0.1859(6) 0.2789(2) 0.0242(8) Uani 1 1 d . . . . .
C20 C 0.4700(3) 0.4862(6) 0.1885(2) 0.0251(8) Uani 1 1 d . . . . .
C28 C 0.4448(3) 0.7404(6) 0.3075(2) 0.0241(7) Uani 1 1 d . . . . .
C36 C 0.5306(2) 0.8523(6) 0.2795(2) 0.0254(8) Uani 1 1 d . . . . .
H36 H 0.5108 0.9673 0.2446 0.030 Uiso 1 1 calc R U . . .
C29 C 0.3820(3) 0.8858(6) 0.3484(2) 0.0264(8) Uani 1 1 d . . . . .
C27 C 0.4063(2) 0.6345(6) 0.2338(2) 0.0241(8) Uani 1 1 d . . . . .
C5 C 0.9298(3) -0.1739(7) 0.5051(2) 0.0318(9) Uani 1 1 d . . . . .
H5 H 0.9616 -0.2853 0.5281 0.038 Uiso 1 1 calc R U . . .
C18 C 0.8488(3) 0.4541(6) 0.1063(2) 0.0275(8) Uani 1 1 d . . . . .
C21 C 0.4310(3) 0.4445(6) 0.1067(2) 0.0254(8) Uani 1 1 d . . . . .
C17 C 0.8596(3) 0.3823(6) 0.1874(2) 0.0250(8) Uani 1 1 d . . . . .
H17 H 0.8604 0.5054 0.2223 0.030 Uiso 1 1 calc R U . . .
C19 C 0.7792(2) 0.2491(6) 0.2107(2) 0.0234(7) Uani 1 1 d . . . . .
C16 C 1.0304(3) 0.4182(6) 0.1787(2) 0.0247(8) Uani 1 1 d . . . . .
C14 C 1.1329(3) 0.6993(7) 0.1831(2) 0.0321(9) Uani 1 1 d . . . . .
H14 H 1.1558 0.8180 0.2086 0.038 Uiso 1 1 calc R U . . .
C15 C 1.0610(3) 0.5941(7) 0.2155(2) 0.0287(8) Uani 1 1 d . . . . .
H15 H 1.0335 0.6424 0.2619 0.034 Uiso 1 1 calc R U . . .
C33 C 0.3426(3) 0.9602(7) 0.4836(2) 0.0315(9) Uani 1 1 d . . . . .
H33 H 0.3467 0.9283 0.5379 0.038 Uiso 1 1 calc R U . . .
C30 C 0.3334(3) 1.0542(6) 0.3214(2) 0.0292(8) Uani 1 1 d . . . . .
H30 H 0.3307 1.0869 0.2671 0.035 Uiso 1 1 calc R U . . .
C13 C 1.1713(3) 0.6321(8) 0.1138(3) 0.0356(10) Uani 1 1 d . . . . .
H13 H 1.2190 0.7082 0.0917 0.043 Uiso 1 1 calc R U . . .
C11 C 1.0718(3) 0.3511(7) 0.1105(2) 0.0293(8) Uani 1 1 d . . . . .
C25 C 0.3430(3) 0.2298(7) 0.0206(2) 0.0350(9) Uani 1 1 d . . . . .
H25 H 0.3120 0.1051 0.0111 0.042 Uiso 1 1 calc R U . . .
C7 C 0.8783(2) 0.0354(6) 0.3012(2) 0.0251(8) Uani 1 1 d . . . . .
C4 C 0.8889(3) -0.0292(7) 0.5522(2) 0.0316(9) Uani 1 1 d . . . . .
H4 H 0.8931 -0.0409 0.6076 0.038 Uiso 1 1 calc R U . . .
C10 C 0.9623(3) 0.1105(6) 0.1297(2) 0.0275(8) Uani 1 1 d . . . . .
C31 C 0.2888(3) 1.1737(7) 0.3765(3) 0.0337(9) Uani 1 1 d . . . . .
H31 H 0.2541 1.2873 0.3590 0.040 Uiso 1 1 calc R U . . .
C3 C 0.8420(3) 0.1323(7) 0.5187(2) 0.0316(9) Uani 1 1 d . . . . .
H3A H 0.8139 0.2309 0.5512 0.038 Uiso 1 1 calc R U . . .
C22 C 0.4374(3) 0.5894(7) 0.0470(2) 0.0309(8) Uani 1 1 d . . . . .
H22 H 0.4710 0.7112 0.0554 0.037 Uiso 1 1 calc R U . . .
C32 C 0.2939(3) 1.1304(7) 0.4562(2) 0.0315(9) Uani 1 1 d . . . . .
H32 H 0.2642 1.2166 0.4925 0.038 Uiso 1 1 calc R U . . .
C12 C 1.1412(3) 0.4558(8) 0.0763(3) 0.0369(10) Uani 1 1 d . . . . .
H12 H 1.1674 0.4092 0.0291 0.044 Uiso 1 1 calc R U . . .
C26 C 0.3842(3) 0.2633(7) 0.0931(2) 0.0308(8) Uani 1 1 d . . . . .
H26 H 0.3803 0.1629 0.1332 0.037 Uiso 1 1 calc R U . . .
C2 C 0.8361(3) 0.1503(7) 0.4377(2) 0.0298(8) Uani 1 1 d . . . . .
H2A H 0.8037 0.2610 0.4149 0.036 Uiso 1 1 calc R U . . .
C9 C 0.9525(2) 0.2740(6) 0.1960(2) 0.0244(8) Uani 1 1 d . . . . .
C23 C 0.3947(3) 0.5561(7) -0.0244(2) 0.0342(9) Uani 1 1 d . . . . .
H23 H 0.3980 0.6566 -0.0646 0.041 Uiso 1 1 calc R U . . .
H6A H 0.597(4) 0.515(9) 0.160(3) 0.035(13) Uiso 1 1 d . . . . .
H1 H 0.749(4) 0.037(10) 0.283(3) 0.047(15) Uiso 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
F1 C8 1.363(5) . ?
F2 C8 1.357(4) . ?
F3 C27 1.353(4) . ?
F4 C27 1.365(4) . ?
O51 C38 1.233(5) . ?
O1 C19 1.207(5) . ?
O4 H4A 0.8400 . ?
O4 C20 1.390(5) . ?
O2 H2 0.8400 . ?
O2 C7 1.400(5) . ?
O3 C35 1.229(5) . ?
O27 C10 1.228(5) . ?
N1 C19 1.351(5) . ?
N1 C7 1.469(5) . ?
N1 H1 0.88(6) . ?
N5 H5A 0.8800 . ?
N5 C35 1.340(5) . ?
N5 C34 1.409(5) . ?
N6 C38 1.345(5) . ?
N6 C20 1.473(5) . ?
N6 H6A 0.83(6) . ?
N4 C37 1.147(5) . ?
N3 H3 0.8800 . ?
N3 C11 1.408(6) . ?
N3 C10 1.335(5) . ?
N2 C18 1.145(5) . ?
C38 C36 1.523(5) . ?
C37 C36 1.466(5) . ?
C1 C6 1.386(6) . ?
C1 C7 1.524(5) . ?
C1 C2 1.391(6) . ?
C35 C28 1.560(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.381(7) . ?
C24 C23 1.391(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.391(6) . ?
C34 C29 1.391(5) . ?
C34 C33 1.373(6) . ?
C8 C7 1.562(5) . ?
C8 C9 1.526(5) . ?
C20 C27 1.567(5) . ?
C20 C21 1.529(5) . ?
C28 C36 1.555(5) . ?
C28 C29 1.511(5) . ?
C28 C27 1.539(5) . ?
C36 H36 1.0000 . ?
C29 C30 1.391(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.387(6) . ?
C18 C17 1.467(5) . ?
C21 C22 1.393(6) . ?
C21 C26 1.392(6) . ?
C17 H17 1.0000 . ?
C17 C19 1.538(5) . ?
C17 C9 1.561(5) . ?
C16 C15 1.383(6) . ?
C16 C11 1.395(6) . ?
C16 C9 1.528(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.394(6) . ?
C14 C13 1.392(6) . ?
C15 H15 0.9500 . ?
C33 H33 0.9500 . ?
C33 C32 1.404(6) . ?
C30 H30 0.9500 . ?
C30 C31 1.397(6) . ?
C13 H13 0.9500 . ?
C13 C12 1.388(7) . ?
C11 C12 1.377(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.390(6) . ?
C4 H4 0.9500 . ?
C4 C3 1.384(6) . ?
C10 C9 1.563(5) . ?
C31 H31 0.9500 . ?
C31 C32 1.390(6) . ?
C3 H3A 0.9500 . ?
C3 C2 1.387(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.385(6) . ?
C32 H32 0.9500 . ?
C12 H12 0.9500 . ?
C26 H26 0.9500 . ?
C2 H2A 0.9500 . ?
C23 H23 0.9500 . ?

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
C20 O4 H4A 109.5 . . ?
C7 O2 H2 109.5 . . ?
C19 N1 C7 128.5(3) . . ?
C19 N1 H1 116(4) . . ?
C7 N1 H1 110(4) . . ?
C35 N5 H5A 123.7 . . ?
C35 N5 C34 112.6(3) . . ?
C34 N5 H5A 123.7 . . ?
C38 N6 C20 127.3(3) . . ?
C38 N6 H6A 112(4) . . ?
C20 N6 H6A 115(4) . . ?
C11 N3 H3 123.3 . . ?
C10 N3 H3 123.3 . . ?
C10 N3 C11 113.4(3) . . ?
O51 C38 N6 122.9(4) . . ?
O51 C38 C36 120.2(3) . . ?
N6 C38 C36 116.6(3) . . ?
N4 C37 C36 177.1(4) . . ?
C6 C1 C7 119.8(3) . . ?
C6 C1 C2 119.2(3) . . ?
C2 C1 C7 120.8(4) . . ?
O3 C35 N5 126.3(4) . . ?
O3 C35 C28 126.3(3) . . ?
N5 C35 C28 107.3(3) . . ?
C25 C24 H24 120.2 . . ?
C25 C24 C23 119.5(4) . . ?
C23 C24 H24 120.2 . . ?
C1 C6 H6 119.6 . . ?
C1 C6 C5 120.7(4) . . ?
C5 C6 H6 119.6 . . ?
C29 C34 N5 109.2(3) . . ?
C33 C34 N5 127.3(4) . . ?
C33 C34 C29 123.6(4) . . ?
F1 C8 C7 108.6(3) . . ?
F1 C8 C9 106.4(3) . . ?
F2 C8 F1 106.7(3) . . ?
F2 C8 C7 108.1(3) . . ?
F2 C8 C9 109.9(3) . . ?
C9 C8 C7 116.8(3) . . ?
O4 C20 N6 110.0(3) . . ?
O4 C20 C27 110.2(3) . . ?
O4 C20 C21 108.3(3) . . ?
N6 C20 C27 108.4(3) . . ?
N6 C20 C21 110.6(3) . . ?
C21 C20 C27 109.5(3) . . ?
C36 C28 C35 109.2(3) . . ?
C29 C28 C35 101.7(3) . . ?
C29 C28 C36 111.4(3) . . ?
C29 C28 C27 115.6(3) . . ?
C27 C28 C35 113.8(3) . . ?
C27 C28 C36 105.1(3) . . ?
C38 C36 C28 115.2(3) . . ?
C38 C36 H36 107.3 . . ?
C37 C36 C38 109.2(3) . . ?
C37 C36 C28 110.2(3) . . ?
C37 C36 H36 107.3 . . ?
C28 C36 H36 107.3 . . ?
C34 C29 C28 108.4(3) . . ?
C34 C29 C30 119.4(4) . . ?
C30 C29 C28 131.8(3) . . ?
F3 C27 F4 106.8(3) . . ?
F3 C27 C20 107.7(3) . . ?
F3 C27 C28 109.6(3) . . ?
F4 C27 C20 109.2(3) . . ?
F4 C27 C28 105.9(3) . . ?
C28 C27 C20 117.2(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 C6 119.4(4) . . ?
C4 C5 H5 120.3 . . ?
N2 C18 C17 174.0(4) . . ?
C22 C21 C20 121.1(4) . . ?
C26 C21 C20 119.2(4) . . ?
C26 C21 C22 119.6(4) . . ?
C18 C17 H17 107.7 . . ?
C18 C17 C19 110.4(3) . . ?
C18 C17 C9 108.6(3) . . ?
C19 C17 H17 107.7 . . ?
C19 C17 C9 114.5(3) . . ?
C9 C17 H17 107.7 . . ?
O1 C19 N1 123.3(4) . . ?
O1 C19 C17 120.8(3) . . ?
N1 C19 C17 115.7(3) . . ?
C15 C16 C11 119.5(4) . . ?
C15 C16 C9 132.2(3) . . ?
C11 C16 C9 108.3(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.6(4) . . ?
C16 C15 C14 118.7(4) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C34 C33 H33 121.5 . . ?
C34 C33 C32 116.9(4) . . ?
C32 C33 H33 121.5 . . ?
C29 C30 H30 121.0 . . ?
C29 C30 C31 118.0(4) . . ?
C31 C30 H30 121.0 . . ?
C14 C13 H13 119.4 . . ?
C12 C13 C14 121.2(4) . . ?
C12 C13 H13 119.4 . . ?
C16 C11 N3 109.1(3) . . ?
C12 C11 N3 128.1(4) . . ?
C12 C11 C16 122.8(4) . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.6(4) . . ?
C26 C25 H25 119.7 . . ?
O2 C7 N1 109.9(3) . . ?
O2 C7 C1 108.0(3) . . ?
O2 C7 C8 110.1(3) . . ?
N1 C7 C1 111.2(3) . . ?
N1 C7 C8 108.1(3) . . ?
C1 C7 C8 109.5(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 H4 119.9 . . ?
O27 C10 N3 127.2(4) . . ?
O27 C10 C9 125.3(4) . . ?
N3 C10 C9 107.4(3) . . ?
C30 C31 H31 119.2 . . ?
C32 C31 C30 121.6(4) . . ?
C32 C31 H31 119.2 . . ?
C4 C3 H3A 120.0 . . ?
C4 C3 C2 120.0(4) . . ?
C2 C3 H3A 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.1(4) . . ?
C23 C22 H22 120.0 . . ?
C33 C32 H32 119.8 . . ?
C31 C32 C33 120.5(4) . . ?
C31 C32 H32 119.8 . . ?
C13 C12 H12 121.4 . . ?
C11 C12 C13 117.2(4) . . ?
C11 C12 H12 121.4 . . ?
C21 C26 H26 120.1 . . ?
C25 C26 C21 119.8(4) . . ?
C25 C26 H26 120.1 . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2A 119.8 . . ?
C8 C9 C17 105.7(3) . . ?
C8 C9 C16 113.6(3) . . ?
C8 C9 C10 114.3(3) . . ?
C17 C9 C10 109.4(3) . . ?
C16 C9 C17 112.3(3) . . ?
C16 C9 C10 101.7(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 C24 120.3(4) . . ?
C22 C23 H23 119.8 . . ?

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
F1 C8 C7 O2 -163.8(3) . . . . ?
F1 C8 C7 N1 76.1(4) . . . . ?
F1 C8 C7 C1 -45.2(4) . . . . ?
F1 C8 C9 C17 -64.4(4) . . . . ?
F1 C8 C9 C16 59.2(4) . . . . ?
F1 C8 C9 C10 175.2(3) . . . . ?
F2 C8 C7 O2 -48.4(4) . . . . ?
F2 C8 C7 N1 -168.5(3) . . . . ?
F2 C8 C7 C1 70.2(4) . . . . ?
F2 C8 C9 C17 -179.5(3) . . . . ?
F2 C8 C9 C16 -55.9(4) . . . . ?
F2 C8 C9 C10 60.1(4) . . . . ?
O51 C38 C36 C37 -23.6(5) . . . . ?
O51 C38 C36 C28 -148.2(4) . . . . ?
O4 C20 C27 F3 -47.0(4) . . . . ?
O4 C20 C27 F4 -162.5(3) . . . . ?
O4 C20 C27 C28 77.0(4) . . . . ?
O4 C20 C21 C22 -163.1(3) . . . . ?
O4 C20 C21 C26 20.5(5) . . . . ?
O3 C35 C28 C36 -65.5(5) . . . . ?
O3 C35 C28 C29 176.6(4) . . . . ?
O3 C35 C28 C27 51.6(5) . . . . ?
O27 C10 C9 C8 57.4(5) . . . . ?
O27 C10 C9 C17 -60.9(5) . . . . ?
O27 C10 C9 C16 -179.8(4) . . . . ?
N5 C35 C28 C36 110.6(3) . . . . ?
N5 C35 C28 C29 -7.3(4) . . . . ?
N5 C35 C28 C27 -132.4(3) . . . . ?
N5 C34 C29 C28 -6.5(4) . . . . ?
N5 C34 C29 C30 179.1(4) . . . . ?
N5 C34 C33 C32 -179.6(4) . . . . ?
N6 C38 C36 C37 162.3(3) . . . . ?
N6 C38 C36 C28 37.8(5) . . . . ?
N6 C20 C27 F3 -167.3(3) . . . . ?
N6 C20 C27 F4 77.1(4) . . . . ?
N6 C20 C27 C28 -43.3(4) . . . . ?
N6 C20 C21 C22 -42.6(5) . . . . ?
N6 C20 C21 C26 141.0(4) . . . . ?
N3 C11 C12 C13 -179.5(4) . . . . ?
N3 C10 C9 C8 -125.7(3) . . . . ?
N3 C10 C9 C17 116.0(3) . . . . ?
N3 C10 C9 C16 -2.9(4) . . . . ?
C38 N6 C20 O4 -93.0(4) . . . . ?
C38 N6 C20 C27 27.5(5) . . . . ?
C38 N6 C20 C21 147.5(4) . . . . ?
C1 C6 C5 C4 -0.2(6) . . . . ?
C35 N5 C34 C29 1.6(5) . . . . ?
C35 N5 C34 C33 -177.3(4) . . . . ?
C35 C28 C36 C38 72.1(4) . . . . ?
C35 C28 C36 C37 -52.0(4) . . . . ?
C35 C28 C29 C34 8.2(4) . . . . ?
C35 C28 C29 C30 -178.4(4) . . . . ?
C35 C28 C27 F3 59.0(4) . . . . ?
C35 C28 C27 F4 173.8(3) . . . . ?
C35 C28 C27 C20 -64.0(4) . . . . ?
C24 C25 C26 C21 -1.1(6) . . . . ?
C6 C1 C7 O2 26.5(5) . . . . ?
C6 C1 C7 N1 147.2(4) . . . . ?
C6 C1 C7 C8 -93.4(4) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
C6 C5 C4 C3 0.4(6) . . . . ?
C34 N5 C35 O3 180.0(4) . . . . ?
C34 N5 C35 C28 3.9(4) . . . . ?
C34 C29 C30 C31 0.3(6) . . . . ?
C34 C33 C32 C31 0.1(6) . . . . ?
C20 N6 C38 O51 160.0(4) . . . . ?
C20 N6 C38 C36 -26.1(5) . . . . ?
C20 C21 C22 C23 -174.2(4) . . . . ?
C20 C21 C26 C25 175.5(4) . . . . ?
C28 C29 C30 C31 -172.5(4) . . . . ?
C36 C28 C29 C34 -108.0(4) . . . . ?
C36 C28 C29 C30 65.4(5) . . . . ?
C36 C28 C27 F3 178.4(3) . . . . ?
C36 C28 C27 F4 -66.8(3) . . . . ?
C36 C28 C27 C20 55.4(4) . . . . ?
C29 C34 C33 C32 1.7(6) . . . . ?
C29 C28 C36 C38 -176.3(3) . . . . ?
C29 C28 C36 C37 59.6(4) . . . . ?
C29 C28 C27 F3 -58.3(4) . . . . ?
C29 C28 C27 F4 56.5(4) . . . . ?
C29 C28 C27 C20 178.7(3) . . . . ?
C29 C30 C31 C32 1.5(7) . . . . ?
C27 C20 C21 C22 76.8(4) . . . . ?
C27 C20 C21 C26 -99.6(4) . . . . ?
C27 C28 C36 C38 -50.4(4) . . . . ?
C27 C28 C36 C37 -174.4(3) . . . . ?
C27 C28 C29 C34 132.1(3) . . . . ?
C27 C28 C29 C30 -54.5(6) . . . . ?
C5 C4 C3 C2 -0.2(6) . . . . ?
C18 C17 C19 O1 -25.6(5) . . . . ?
C18 C17 C19 N1 159.4(3) . . . . ?
C18 C17 C9 C8 -174.7(3) . . . . ?
C18 C17 C9 C16 60.9(4) . . . . ?
C18 C17 C9 C10 -51.2(4) . . . . ?
C21 C20 C27 F3 72.0(4) . . . . ?
C21 C20 C27 F4 -43.6(4) . . . . ?
C21 C20 C27 C28 -164.0(3) . . . . ?
C21 C22 C23 C24 -1.4(6) . . . . ?
C19 N1 C7 O2 -92.9(5) . . . . ?
C19 N1 C7 C1 147.6(4) . . . . ?
C19 N1 C7 C8 27.3(5) . . . . ?
C19 C17 C9 C8 -50.9(4) . . . . ?
C19 C17 C9 C16 -175.2(3) . . . . ?
C19 C17 C9 C10 72.6(4) . . . . ?
C16 C11 C12 C13 1.7(6) . . . . ?
C14 C13 C12 C11 0.2(6) . . . . ?
C15 C16 C11 N3 179.3(3) . . . . ?
C15 C16 C11 C12 -1.7(6) . . . . ?
C15 C16 C9 C8 -55.9(6) . . . . ?
C15 C16 C9 C17 64.0(5) . . . . ?
C15 C16 C9 C10 -179.2(4) . . . . ?
C15 C14 C13 C12 -2.0(7) . . . . ?
C33 C34 C29 C28 172.4(4) . . . . ?
C33 C34 C29 C30 -2.0(6) . . . . ?
C30 C31 C32 C33 -1.7(7) . . . . ?
C13 C14 C15 C16 1.9(6) . . . . ?
C11 N3 C10 O27 178.1(4) . . . . ?
C11 N3 C10 C9 1.3(4) . . . . ?
C11 C16 C15 C14 -0.1(6) . . . . ?
C11 C16 C9 C8 126.8(4) . . . . ?
C11 C16 C9 C17 -113.3(4) . . . . ?
C11 C16 C9 C10 3.6(4) . . . . ?
C25 C24 C23 C22 -0.6(6) . . . . ?
C7 N1 C19 O1 160.1(4) . . . . ?
C7 N1 C19 C17 -25.0(6) . . . . ?
C7 C1 C6 C5 174.8(4) . . . . ?
C7 C1 C2 C3 -174.5(4) . . . . ?
C7 C8 C9 C17 56.9(4) . . . . ?
C7 C8 C9 C16 -179.5(3) . . . . ?
C7 C8 C9 C10 -63.5(4) . . . . ?
C4 C3 C2 C1 -0.2(6) . . . . ?
C10 N3 C11 C16 1.1(5) . . . . ?
C10 N3 C11 C12 -177.8(4) . . . . ?
C22 C21 C26 C25 -0.9(6) . . . . ?
C26 C21 C22 C23 2.2(6) . . . . ?
C2 C1 C6 C5 -0.2(6) . . . . ?
C2 C1 C7 O2 -158.6(4) . . . . ?
C2 C1 C7 N1 -37.9(5) . . . . ?
C2 C1 C7 C8 81.5(4) . . . . ?
C9 C8 C7 O2 76.1(4) . . . . ?
C9 C8 C7 N1 -44.0(4) . . . . ?
C9 C8 C7 C1 -165.3(3) . . . . ?
C9 C17 C19 O1 -148.5(4) . . . . ?
C9 C17 C19 N1 36.4(4) . . . . ?
C9 C16 C15 C14 -177.1(4) . . . . ?
C9 C16 C11 N3 -3.1(4) . . . . ?
C9 C16 C11 C12 175.9(4) . . . . ?
C23 C24 C25 C26 1.8(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.787
_oxdiff_exptl_absorpt_empirical_full_min 0.526
