# 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_caozhengq_0519_auto
_database_code_depnum_ccdc_archive 'CCDC 2324543'
loop_
_audit_author_name
_audit_author_address
caozhengq
;Lanzhou University 
China
;
_audit_update_record             
;
2024-01-10 deposited with the CCDC.	2024-04-22 downloaded from the CCDC.
;
_audit_creation_date             2023-05-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H22 F N O5'
_chemical_formula_sum            'C31 H22 F N O5'
_chemical_formula_weight         507.49
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.67378(10)
_cell_length_b                   9.99752(9)
_cell_length_c                   25.0687(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2424.49(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10049
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.0630
_cell_measurement_theta_min      1.7360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            13770
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.310
_diffrn_reflns_theta_min         3.526
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  49.00   0.50    0.08    --   45.34 -52.00 -45.00  130
  2  ω    107.00 173.00   0.50    0.31    --  109.53  30.00-150.00  132
  3  ω    109.00 172.00   0.50    0.31    --  109.53  77.00-120.00  126
  4  ω     64.00  96.00   0.50    0.31    --  109.53-109.00  85.00   64
  5  ω     42.00  67.00   0.50    0.31    --  109.53 -61.00 150.00   50
  6  ω    -26.00  18.00   0.50    0.08    --   45.34 -19.00  60.00   88
  7  ω    -30.00  18.00   0.50    0.08    --   45.34 -19.00   0.00   96
  8  ω    -54.00 -28.00   0.50    0.31    -- -100.00 125.00 -30.00   52
  9  ω   -112.00 -58.00   0.50    0.31    -- -100.00 125.00 -30.00  108
 10  ω    -65.00 -27.00   0.50    0.31    -- -100.00  61.00 -30.00   76
 11  ω    -94.00 -26.00   0.50    0.31    -- -100.00  72.00 -62.00  136
 12  ω    -55.00 -30.00   0.50    0.31    -- -100.00  61.00-150.00   50
 13  ω    -64.00 -36.00   0.50    0.31    -- -100.00 109.00-178.00   56
 14  ω    -51.00 -25.00   0.50    0.31    -- -100.00  45.00-120.00   52
 15  ω    -53.00 -28.00   0.50    0.31    -- -100.00  45.00-150.00   50
 16  ω    -54.00 -25.00   0.50    0.31    -- -100.00  45.00 -60.00   58
 17  ω    -54.00 -25.00   0.50    0.31    -- -100.00  45.00 -90.00   58
 18  ω    -61.00 -26.00   0.50    0.31    -- -100.00  52.00 100.00   70
 19  ω    -54.00 -25.00   0.50    0.31    -- -100.00  45.00 150.00   58
 20  ω    -54.00 -29.00   0.50    0.31    -- -100.00  45.00  60.00   50
 21  ω   -110.00 -81.00   0.50    0.31    -- -100.00 -52.00 -45.00   58
 22  ω   -117.00 -49.00   0.50    0.08    --  -45.34-179.00-180.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1068353000
_diffrn_orient_matrix_UB_12      0.0860994000
_diffrn_orient_matrix_UB_13      -0.0298832000
_diffrn_orient_matrix_UB_21      0.1129350000
_diffrn_orient_matrix_UB_22      0.0451847000
_diffrn_orient_matrix_UB_23      -0.0394251000
_diffrn_orient_matrix_UB_31      -0.0343414000
_diffrn_orient_matrix_UB_32      -0.1196398000
_diffrn_orient_matrix_UB_33      -0.0364350000
_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         0.721
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.907
_reflns_number_gt                4551
_reflns_number_total             4746
_reflns_odcompleteness_completeness 100.00
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1855 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_coef       0.00131(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4746
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0291
_refine_ls_restrained_S_all      1.072
_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)+(0.0364P)²+0.3774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0752
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C24(H24)
1.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C25(H25A,H25B), C19(H19A,H19B)
1.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C6(H6), C17(H17), C21(H21), C10(H10), C27(H27), C11(H11),
 C14(H14), C31(H31), C12(H12), C28(H28), C30(H30), C13(H13), C29(H29)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.14806(14) 0.58100(13) 0.47884(5) 0.0419(3) Uani 1 1 d . . . . .
O4 O 0.37370(15) -0.05049(12) 0.35342(5) 0.0312(3) Uani 1 1 d . . . . .
O3 O -0.07035(15) -0.03884(14) 0.26808(6) 0.0365(3) Uani 1 1 d . . . . .
O2 O -0.08541(15) 0.19176(14) 0.27164(6) 0.0373(3) Uani 1 1 d . . . . .
O1 O 0.54861(15) 0.19175(14) 0.29733(5) 0.0330(3) Uani 1 1 d . . . . .
O5 O 0.57949(19) -0.05084(17) 0.38964(8) 0.0555(5) Uani 1 1 d . . . . .
N1 N 0.48706(16) 0.40694(16) 0.31882(6) 0.0254(3) Uani 1 1 d . . . . .
C3 C 0.33218(18) 0.37228(16) 0.38651(7) 0.0206(3) Uani 1 1 d . . . . .
C4 C 0.24487(18) 0.40806(19) 0.42770(7) 0.0245(3) Uani 1 1 d . . . . .
H4 H 0.195791 0.342865 0.447731 0.029 Uiso 1 1 calc R U . . .
C8 C 0.40168(18) 0.46935(18) 0.35728(7) 0.0230(4) Uani 1 1 d . . . . .
C16 C 0.25207(18) 0.16028(17) 0.33988(7) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.48003(19) 0.27197(19) 0.32281(7) 0.0247(4) Uani 1 1 d . . . . .
C5 C 0.2322(2) 0.5430(2) 0.43840(7) 0.0287(4) Uani 1 1 d . . . . .
C22 C 0.25826(19) 0.02185(18) 0.33655(7) 0.0244(4) Uani 1 1 d . . . . .
C20 C 0.0441(2) 0.01200(19) 0.29298(7) 0.0263(4) Uani 1 1 d . . . . .
C7 C 0.3862(2) 0.60425(18) 0.36765(8) 0.0291(4) Uani 1 1 d . . . . .
H7 H 0.433016 0.669753 0.346984 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5845(2) 0.4768(2) 0.28377(7) 0.0318(4) Uani 1 1 d . . . . .
H9A H 0.535249 0.548781 0.264439 0.038 Uiso 1 1 calc R U . . .
H9B H 0.621180 0.413136 0.257028 0.038 Uiso 1 1 calc R U . . .
C6 C 0.2991(2) 0.64077(19) 0.40965(8) 0.0318(4) Uani 1 1 d . . . . .
H6 H 0.286100 0.732429 0.418290 0.038 Uiso 1 1 calc R U . . .
C2 C 0.37124(19) 0.23540(17) 0.36571(7) 0.0221(3) Uani 1 1 d . . . . .
C17 C 0.13657(19) 0.22668(17) 0.31834(7) 0.0235(4) Uani 1 1 d . . . . .
H17 H 0.128753 0.321322 0.319899 0.028 Uiso 1 1 calc R U . . .
C21 C 0.1546(2) -0.05624(18) 0.31350(7) 0.0271(4) Uani 1 1 d . . . . .
H21 H 0.160351 -0.151036 0.312153 0.033 Uiso 1 1 calc R U . . .
C15 C 0.7032(2) 0.5365(2) 0.31485(8) 0.0304(4) Uani 1 1 d . . . . .
C24 C 0.4391(2) 0.14343(18) 0.40815(7) 0.0257(4) Uani 1 1 d . . . . .
H24 H 0.368766 0.126810 0.436638 0.031 Uiso 1 1 calc R U . . .
C26 C 0.5427(2) 0.3098(2) 0.47627(7) 0.0281(4) Uani 1 1 d . . . . .
C23 C 0.4744(2) 0.00937(19) 0.38320(8) 0.0334(4) Uani 1 1 d . . . . .
C10 C 0.8010(2) 0.4533(2) 0.33864(8) 0.0330(4) Uani 1 1 d . . . . .
H10 H 0.795069 0.359225 0.333810 0.040 Uiso 1 1 calc R U . . .
C27 C 0.4622(2) 0.2853(2) 0.52132(8) 0.0346(5) Uani 1 1 d . . . . .
H27 H 0.420195 0.200127 0.525908 0.042 Uiso 1 1 calc R U . . .
C18 C 0.0359(2) 0.15019(19) 0.29505(7) 0.0259(4) Uani 1 1 d . . . . .
C11 C 0.9059(2) 0.5061(2) 0.36903(10) 0.0384(5) Uani 1 1 d . . . . .
H11 H 0.971734 0.448588 0.385251 0.046 Uiso 1 1 calc R U . . .
C14 C 0.7153(2) 0.6728(2) 0.32101(10) 0.0408(5) Uani 1 1 d . . . . .
H14 H 0.650964 0.730649 0.304069 0.049 Uiso 1 1 calc R U . . .
C31 C 0.6027(2) 0.4350(2) 0.47057(8) 0.0364(5) Uani 1 1 d . . . . .
H31 H 0.658573 0.453324 0.440277 0.044 Uiso 1 1 calc R U . . .
C25 C 0.5686(2) 0.20144(19) 0.43527(8) 0.0294(4) Uani 1 1 d . . . . .
H25A H 0.618853 0.127316 0.452862 0.035 Uiso 1 1 calc R U . . .
H25B H 0.629917 0.238226 0.407271 0.035 Uiso 1 1 calc R U . . .
C12 C 0.9155(2) 0.6434(2) 0.37601(11) 0.0471(6) Uani 1 1 d . . . . .
H12 H 0.987199 0.680081 0.397411 0.057 Uiso 1 1 calc R U . . .
C28 C 0.4427(3) 0.3838(3) 0.55950(8) 0.0457(6) Uani 1 1 d . . . . .
H28 H 0.388073 0.365646 0.590162 0.055 Uiso 1 1 calc R U . . .
C30 C 0.5821(3) 0.5337(3) 0.50855(10) 0.0508(6) Uani 1 1 d . . . . .
H30 H 0.622938 0.619390 0.503983 0.061 Uiso 1 1 calc R U . . .
C13 C 0.8210(3) 0.7263(2) 0.35181(12) 0.0519(7) Uani 1 1 d . . . . .
H13 H 0.828003 0.820423 0.356191 0.062 Uiso 1 1 calc R U . . .
C19 C -0.1551(3) 0.0729(2) 0.25663(13) 0.0548(7) Uani 1 1 d . . . . .
H19A H -0.243242 0.065594 0.276456 0.066 Uiso 1 1 calc R U . . .
H19B H -0.176416 0.075350 0.218015 0.066 Uiso 1 1 calc R U . . .
C29 C 0.5021(3) 0.5078(3) 0.55310(10) 0.0527(7) Uani 1 1 d . . . . .
H29 H 0.488347 0.575339 0.579214 0.063 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C5 1.354(2) . ?
O4 C22 1.396(2) . ?
O4 C23 1.365(2) . ?
O3 C20 1.369(2) . ?
O3 C19 1.415(3) . ?
O2 C18 1.376(2) . ?
O2 C19 1.417(3) . ?
O1 C1 1.221(2) . ?
O5 C23 1.192(3) . ?
N1 C8 1.415(2) . ?
N1 C1 1.355(2) . ?
N1 C9 1.465(2) . ?
C3 C4 1.381(3) . ?
C3 C8 1.389(3) . ?
C3 C2 1.512(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(3) . ?
C8 C7 1.382(3) . ?
C16 C22 1.388(2) . ?
C16 C2 1.521(2) . ?
C16 C17 1.407(2) . ?
C1 C2 1.549(2) . ?
C5 C6 1.376(3) . ?
C22 C21 1.396(3) . ?
C20 C21 1.368(3) . ?
C20 C18 1.385(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.397(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C15 1.511(3) . ?
C6 H6 0.9500 . ?
C2 C24 1.552(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.369(3) . ?
C21 H21 0.9500 . ?
C15 C10 1.394(3) . ?
C15 C14 1.376(3) . ?
C24 H24 1.0000 . ?
C24 C23 1.518(3) . ?
C24 C25 1.539(3) . ?
C26 C27 1.394(3) . ?
C26 C31 1.387(3) . ?
C26 C25 1.514(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.374(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.386(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.387(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.388(3) . ?
C31 H31 0.9500 . ?
C31 C30 1.386(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C13 1.375(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.376(4) . ?
C30 H30 0.9500 . ?
C30 C29 1.383(4) . ?
C13 H13 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C29 H29 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
C23 O4 C22 120.61(14) . . ?
C20 O3 C19 105.53(15) . . ?
C18 O2 C19 105.40(15) . . ?
C8 N1 C9 125.03(16) . . ?
C1 N1 C8 111.08(15) . . ?
C1 N1 C9 123.44(16) . . ?
C4 C3 C8 120.62(16) . . ?
C4 C3 C2 130.15(16) . . ?
C8 C3 C2 109.23(15) . . ?
C3 C4 H4 121.5 . . ?
C5 C4 C3 116.91(17) . . ?
C5 C4 H4 121.5 . . ?
C3 C8 N1 109.51(15) . . ?
C7 C8 N1 128.47(17) . . ?
C7 C8 C3 122.01(17) . . ?
C22 C16 C2 119.04(16) . . ?
C22 C16 C17 118.78(16) . . ?
C17 C16 C2 122.16(15) . . ?
O1 C1 N1 126.03(17) . . ?
O1 C1 C2 125.27(17) . . ?
N1 C1 C2 108.70(15) . . ?
F1 C5 C4 118.21(18) . . ?
F1 C5 C6 118.39(17) . . ?
C6 C5 C4 123.40(18) . . ?
O4 C22 C21 114.23(15) . . ?
C16 C22 O4 122.20(16) . . ?
C16 C22 C21 123.47(17) . . ?
O3 C20 C18 109.95(17) . . ?
C21 C20 O3 128.17(17) . . ?
C21 C20 C18 121.88(17) . . ?
C8 C7 H7 121.2 . . ?
C8 C7 C6 117.54(18) . . ?
C6 C7 H7 121.2 . . ?
N1 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
N1 C9 C15 111.59(15) . . ?
H9A C9 H9B 108.0 . . ?
C15 C9 H9A 109.3 . . ?
C15 C9 H9B 109.3 . . ?
C5 C6 C7 119.52(17) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C3 C2 C16 113.84(14) . . ?
C3 C2 C1 101.28(14) . . ?
C3 C2 C24 113.92(14) . . ?
C16 C2 C1 109.63(14) . . ?
C16 C2 C24 108.65(14) . . ?
C1 C2 C24 109.20(15) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 C16 117.71(16) . . ?
C18 C17 H17 121.1 . . ?
C22 C21 H21 122.0 . . ?
C20 C21 C22 115.97(16) . . ?
C20 C21 H21 122.0 . . ?
C10 C15 C9 120.05(18) . . ?
C14 C15 C9 120.94(19) . . ?
C14 C15 C10 119.0(2) . . ?
C2 C24 H24 107.5 . . ?
C23 C24 C2 109.63(14) . . ?
C23 C24 H24 107.5 . . ?
C23 C24 C25 109.35(16) . . ?
C25 C24 C2 115.08(15) . . ?
C25 C24 H24 107.5 . . ?
C27 C26 C25 121.09(19) . . ?
C31 C26 C27 118.44(19) . . ?
C31 C26 C25 120.44(18) . . ?
O4 C23 C24 116.85(17) . . ?
O5 C23 O4 117.45(17) . . ?
O5 C23 C24 125.58(19) . . ?
C15 C10 H10 119.7 . . ?
C11 C10 C15 120.60(19) . . ?
C11 C10 H10 119.7 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.7(2) . . ?
C28 C27 H27 119.7 . . ?
O2 C18 C20 109.53(17) . . ?
C17 C18 O2 128.30(17) . . ?
C17 C18 C20 122.16(18) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C15 C14 H14 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C26 C31 H31 119.6 . . ?
C30 C31 C26 120.8(2) . . ?
C30 C31 H31 119.6 . . ?
C24 C25 H25A 108.3 . . ?
C24 C25 H25B 108.3 . . ?
C26 C25 C24 115.77(16) . . ?
C26 C25 H25A 108.3 . . ?
C26 C25 H25B 108.3 . . ?
H25A C25 H25B 107.4 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.1 . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.2(2) . . ?
C29 C28 H28 119.9 . . ?
C31 C30 H30 119.9 . . ?
C29 C30 C31 120.1(2) . . ?
C29 C30 H30 119.9 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
O3 C19 O2 109.43(17) . . ?
O3 C19 H19A 109.8 . . ?
O3 C19 H19B 109.8 . . ?
O2 C19 H19A 109.8 . . ?
O2 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
C28 C29 C30 119.8(2) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?

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 C5 C6 C7 -179.84(17) . . . . ?
O4 C22 C21 C20 -175.45(16) . . . . ?
O3 C20 C21 C22 179.53(18) . . . . ?
O3 C20 C18 O2 0.4(2) . . . . ?
O3 C20 C18 C17 179.44(16) . . . . ?
O1 C1 C2 C3 174.76(17) . . . . ?
O1 C1 C2 C16 -64.7(2) . . . . ?
O1 C1 C2 C24 54.3(2) . . . . ?
N1 C8 C7 C6 -177.29(17) . . . . ?
N1 C1 C2 C3 -4.60(18) . . . . ?
N1 C1 C2 C16 115.98(16) . . . . ?
N1 C1 C2 C24 -125.09(15) . . . . ?
N1 C9 C15 C10 69.0(2) . . . . ?
N1 C9 C15 C14 -109.8(2) . . . . ?
C3 C4 C5 F1 -179.52(15) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C3 C8 C7 C6 1.1(3) . . . . ?
C3 C2 C24 C23 -179.84(16) . . . . ?
C3 C2 C24 C25 -56.1(2) . . . . ?
C4 C3 C8 N1 178.21(15) . . . . ?
C4 C3 C8 C7 -0.5(3) . . . . ?
C4 C3 C2 C16 66.6(2) . . . . ?
C4 C3 C2 C1 -175.88(17) . . . . ?
C4 C3 C2 C24 -58.8(2) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C8 N1 C1 O1 -175.06(17) . . . . ?
C8 N1 C1 C2 4.3(2) . . . . ?
C8 N1 C9 C15 67.3(2) . . . . ?
C8 C3 C4 C5 -0.8(3) . . . . ?
C8 C3 C2 C16 -114.20(16) . . . . ?
C8 C3 C2 C1 3.36(17) . . . . ?
C8 C3 C2 C24 120.44(17) . . . . ?
C8 C7 C6 C5 -0.5(3) . . . . ?
C16 C22 C21 C20 1.0(3) . . . . ?
C16 C2 C24 C23 52.1(2) . . . . ?
C16 C2 C24 C25 175.83(15) . . . . ?
C16 C17 C18 O2 179.82(18) . . . . ?
C16 C17 C18 C20 0.9(3) . . . . ?
C1 N1 C8 C3 -2.1(2) . . . . ?
C1 N1 C8 C7 176.47(18) . . . . ?
C1 N1 C9 C15 -104.3(2) . . . . ?
C1 C2 C24 C23 -67.44(19) . . . . ?
C1 C2 C24 C25 56.29(19) . . . . ?
C22 O4 C23 O5 -169.0(2) . . . . ?
C22 O4 C23 C24 14.7(3) . . . . ?
C22 C16 C2 C3 -157.30(16) . . . . ?
C22 C16 C2 C1 90.08(19) . . . . ?
C22 C16 C2 C24 -29.2(2) . . . . ?
C22 C16 C17 C18 0.0(3) . . . . ?
C20 O3 C19 O2 4.0(3) . . . . ?
C9 N1 C8 C3 -174.58(16) . . . . ?
C9 N1 C8 C7 4.0(3) . . . . ?
C9 N1 C1 O1 -2.4(3) . . . . ?
C9 N1 C1 C2 176.93(15) . . . . ?
C9 C15 C10 C11 -177.04(19) . . . . ?
C9 C15 C14 C13 176.8(2) . . . . ?
C2 C3 C4 C5 178.37(17) . . . . ?
C2 C3 C8 N1 -1.11(19) . . . . ?
C2 C3 C8 C7 -179.78(16) . . . . ?
C2 C16 C22 O4 -3.7(3) . . . . ?
C2 C16 C22 C21 -179.84(16) . . . . ?
C2 C16 C17 C18 178.81(16) . . . . ?
C2 C24 C23 O4 -47.4(2) . . . . ?
C2 C24 C23 O5 136.6(2) . . . . ?
C2 C24 C25 C26 74.9(2) . . . . ?
C17 C16 C22 O4 175.22(16) . . . . ?
C17 C16 C22 C21 -1.0(3) . . . . ?
C17 C16 C2 C3 23.9(2) . . . . ?
C17 C16 C2 C1 -88.76(19) . . . . ?
C17 C16 C2 C24 151.97(16) . . . . ?
C21 C20 C18 O2 -179.98(16) . . . . ?
C21 C20 C18 C17 -0.9(3) . . . . ?
C15 C10 C11 C12 -0.4(3) . . . . ?
C15 C14 C13 C12 0.7(4) . . . . ?
C26 C27 C28 C29 0.4(3) . . . . ?
C26 C31 C30 C29 0.7(4) . . . . ?
C23 O4 C22 C16 12.6(3) . . . . ?
C23 O4 C22 C21 -170.86(17) . . . . ?
C23 C24 C25 C26 -161.25(17) . . . . ?
C10 C15 C14 C13 -1.9(3) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C27 C26 C31 C30 -0.5(3) . . . . ?
C27 C26 C25 C24 59.8(2) . . . . ?
C27 C28 C29 C30 -0.3(4) . . . . ?
C18 O2 C19 O3 -3.8(3) . . . . ?
C18 C20 C21 C22 -0.1(3) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C14 C15 C10 C11 1.8(3) . . . . ?
C31 C26 C27 C28 0.0(3) . . . . ?
C31 C26 C25 C24 -122.3(2) . . . . ?
C31 C30 C29 C28 -0.3(4) . . . . ?
C25 C24 C23 O4 -174.46(17) . . . . ?
C25 C24 C23 O5 9.6(3) . . . . ?
C25 C26 C27 C28 177.91(19) . . . . ?
C25 C26 C31 C30 -178.5(2) . . . . ?
C19 O3 C20 C21 177.7(2) . . . . ?
C19 O3 C20 C18 -2.7(2) . . . . ?
C19 O2 C18 C20 2.1(2) . . . . ?
C19 O2 C18 C17 -176.9(2) . . . . ?

_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 1.211
_oxdiff_exptl_absorpt_empirical_full_min 0.708
