# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_20221124mmf_auto
_database_code_depnum_ccdc_archive 'CCDC 2285093'
loop_
_audit_author_name
_audit_author_address
HXP
;Jining Medical University
China
;
_audit_update_record             
;
2023-07-28 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;
_audit_creation_date             2023-02-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H9 F4 N4 O6'
_chemical_formula_sum            'C32 H0.25 F4 N4 O6'
_chemical_formula_weight         612.61
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CNOF
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'
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'
H H 0.0000 0.0000 '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                   8.4673(3)
_cell_length_b                   11.7335(6)
_cell_length_c                   28.0005(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2781.88(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4361
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      68.7830
_cell_measurement_theta_min      4.0660
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    1.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1217
_exptl_crystal_size_max          0.05
_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  0.0627
_diffrn_reflns_av_unetI/netI     0.0676
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            13212
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.014
_diffrn_reflns_theta_min         3.157
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00 103.00   1.00    5.39    --  106.65 -99.00-150.00   69
  2  ω     40.00  66.00   1.00    5.39    --  106.65 -57.00 -30.00   26
  3  ω     44.00  70.00   1.00    5.39    --  106.65 -60.00 117.00   26
  4  ω     92.00 178.00   1.00    5.39    --  106.65  57.00  60.00   86
  5  ω   -159.00 -73.00   1.00    5.39    --  -91.75 -76.00  -7.00   86
  6  ω   -163.00-138.00   1.00    5.39    --  -91.75 -57.00  60.00   25
  7  ω   -128.00 -77.00   1.00    5.39    --  -91.75 -57.00  60.00   51
  8  ω   -121.00 -26.00   1.00    0.91    --  -48.42 -76.00  -7.00   95
  9  ω    -27.00  27.00   1.00    0.91    --  -48.42  19.00 -90.00   54
 10  ω    -69.00 -31.00   1.00    5.39    --  -91.75  60.00-102.00   38
 11  ω   -117.00 -72.00   1.00    5.39    --  -91.75  88.00   4.00   45
 12  ω    -56.00 -30.00   1.00    5.39    --  -91.75  88.00   4.00   26
 13  ω    -65.00 -20.00   1.00    5.39    --  -91.75  57.00  90.00   45
;
_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      -0.0850772000
_diffrn_orient_matrix_UB_12      -0.0701611000
_diffrn_orient_matrix_UB_13      -0.0386746000
_diffrn_orient_matrix_UB_21      -0.1247641000
_diffrn_orient_matrix_UB_22      0.0948959000
_diffrn_orient_matrix_UB_23      -0.0051560000
_diffrn_orient_matrix_UB_31      0.1015159000
_diffrn_orient_matrix_UB_32      0.0574890000
_diffrn_orient_matrix_UB_33      -0.0387974000
_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         0.705
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.865
_reflns_number_gt                4032
_reflns_number_total             5247
_reflns_odcompleteness_completeness 99.30
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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         0.924
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.145
_refine_ls_abs_structure_details 
;
 Flack x determined using 1289 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.65(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.530
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         5247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1581
_refine_ls_R_factor_gt           0.1410
_refine_ls_restrained_S_all      1.530
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3637
_refine_ls_wR_factor_ref         0.3817
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C4(H4), C27(H27), C5(H5), C26(H26)
2.d Idealised tetrahedral OH refined as rotating group:
 O42(H42)
;
_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
O14 O 0.6089(8) 0.3893(5) 0.3664(2) 0.0434(14) Uani 1 1 d . . . . .
O24 O 0.6062(8) 0.1180(6) 0.6273(2) 0.0462(15) Uani 1 1 d . . . . .
F41 F 0.9727(9) 0.6055(7) 0.2713(2) 0.0724(19) Uani 1 1 d . . . . .
O7 O 0.5613(8) 0.5824(6) 0.4245(2) 0.0521(17) Uani 1 1 d . . . . .
O29 O 0.6496(9) -0.1136(7) 0.6070(2) 0.0568(19) Uani 1 1 d . . . . .
F40 F 0.9242(11) 0.7911(7) 0.3286(3) 0.086(2) Uani 1 1 d . . . . .
O17 O 0.4891(9) 0.1897(7) 0.3877(2) 0.0557(18) Uani 1 1 d . . . . .
F34 F 0.9652(11) -0.1449(10) 0.7411(4) 0.102(3) Uani 1 1 d . . . . .
C28 C 0.5596(11) -0.0523(10) 0.5762(3) 0.047(2) Uani 1 1 d . . . . .
F35 F 0.9290(13) 0.0783(10) 0.7618(3) 0.109(3) Uani 1 1 d . . . . .
O42 O 0.1905(11) 0.0721(10) 0.4024(3) 0.079(3) Uani 1 1 d . . . . .
H42 H 0.221696 0.063720 0.374130 0.119 Uiso 1 1 calc R U . . .
C8 C 0.6548(10) 0.5906(8) 0.3867(3) 0.044(2) Uani 1 1 d . . . . .
C15 C 0.5237(11) 0.3920(9) 0.4086(3) 0.045(2) Uani 1 1 d . . . . .
C11 C 0.8626(13) 0.6016(10) 0.3079(5) 0.065(3) Uani 1 1 d . . . . .
C6 C 0.5030(12) 0.4768(10) 0.4364(5) 0.057(3) Uani 1 1 d . . . . .
C21 C 0.4055(12) -0.0224(10) 0.5062(3) 0.050(2) Uani 1 1 d . . . . .
C25 C 0.5382(10) 0.0751(9) 0.5867(3) 0.045(2) Uani 1 1 d . . . . .
C13 C 0.6824(10) 0.4912(9) 0.3554(3) 0.047(2) Uani 1 1 d . . . . .
C18 C 0.4717(15) 0.0808(10) 0.4076(4) 0.059(3) Uani 1 1 d . . . . .
H18 H 0.549972 0.023114 0.404833 0.071 Uiso 1 1 calc R U . . .
C43 C 0.8145(15) 0.4055(9) 0.2894(5) 0.061(3) Uani 1 1 d . . . . .
C12 C 0.7827(13) 0.4992(10) 0.3184(4) 0.057(3) Uani 1 1 d . . . . .
C1 C 0.3872(13) 0.0960(12) 0.5146(3) 0.061(3) Uani 1 1 d . . . . .
C4 C 0.3503(13) 0.3705(12) 0.4892(4) 0.059(3) Uani 1 1 d . . . . .
H4 H 0.288723 0.363549 0.517422 0.071 Uiso 1 1 calc R U . . .
C16 C 0.4627(10) 0.2797(8) 0.4194(4) 0.046(2) Uani 1 1 d . . . . .
C9 C 0.7437(14) 0.6873(9) 0.3764(4) 0.056(3) Uani 1 1 d . . . . .
C2 C 0.3078(12) 0.1519(10) 0.4750(4) 0.052(2) Uani 1 1 d . . . . .
H2 H 0.193939 0.161863 0.483533 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3737(13) 0.2665(9) 0.4603(4) 0.052(2) Uani 1 1 d . . . . .
C10 C 0.8438(13) 0.6930(11) 0.3374(5) 0.061(3) Uani 1 1 d . . . . .
C27 C 0.4921(14) -0.0942(12) 0.5359(4) 0.060(3) Uani 1 1 d . . . . .
H27 H 0.503846 -0.172442 0.527954 0.072 Uiso 1 1 calc R U . . .
C23 C 0.6942(12) 0.0432(12) 0.6526(3) 0.058(3) Uani 1 1 d . . . . .
C33 C 0.8094(14) -0.1371(13) 0.6756(4) 0.068(4) Uani 1 1 d . . . . .
C5 C 0.4077(12) 0.4725(15) 0.4791(5) 0.070(4) Uani 1 1 d . . . . .
H5 H 0.387924 0.537612 0.498322 0.085 Uiso 1 1 calc R U . . .
C30 C 0.7753(13) 0.0989(11) 0.6961(5) 0.061(3) Uani 1 1 d . . . . .
C22 C 0.7135(13) -0.0605(11) 0.6441(3) 0.054(3) Uani 1 1 d . . . . .
C26 C 0.4575(11) 0.1405(10) 0.5558(4) 0.052(2) Uani 1 1 d . . . . .
H26 H 0.447828 0.219753 0.562204 0.062 Uiso 1 1 calc R U . . .
N46 N 0.7210(16) 0.8521(11) 0.4362(6) 0.086(3) Uani 1 1 d . . . . .
C31 C 0.8569(17) 0.0343(18) 0.7239(4) 0.083(5) Uani 1 1 d . . . . .
N44 N 0.8304(16) 0.3223(12) 0.2637(5) 0.087(3) Uani 1 1 d . . . . .
C36 C 0.8259(17) -0.2460(18) 0.6634(4) 0.084(5) Uani 1 1 d . . . . .
N37 N 0.863(3) -0.333(2) 0.6588(6) 0.166(12) Uani 1 1 d . . . . .
N39 N 0.7494(13) 0.3184(14) 0.7039(4) 0.081(3) Uani 1 1 d . . . . .
C19 C 0.3192(13) 0.0633(10) 0.4335(4) 0.056(3) Uani 1 1 d . . . . .
C38 C 0.7587(14) 0.2215(13) 0.7020(5) 0.063(3) Uani 1 1 d . . . . .
C32 C 0.8811(17) -0.0850(14) 0.7125(6) 0.076(4) Uani 1 1 d . . . . .
C45 C 0.728(2) 0.7850(13) 0.4099(6) 0.078(4) Uani 1 1 d . . . . .
C20 C 0.3211(16) -0.0549(10) 0.4598(4) 0.064(3) Uani 1 1 d . . . . .
H20A H 0.212920 -0.083267 0.465958 0.076 Uiso 1 1 calc R U . . .
H20B H 0.381071 -0.112755 0.441585 0.076 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
O14 C15 1.384(11) . ?
O14 C13 1.382(12) . ?
O24 C25 1.371(12) . ?
O24 C23 1.352(12) . ?
F41 C11 1.387(16) . ?
O7 C8 1.326(12) . ?
O7 C6 1.374(14) . ?
O29 C28 1.357(12) . ?
O29 C22 1.328(14) . ?
F40 C10 1.360(13) . ?
O17 C18 1.402(13) . ?
O17 C16 1.398(13) . ?
F34 C32 1.281(17) . ?
C28 C25 1.533(16) . ?
C28 C27 1.357(15) . ?
F35 C31 1.329(16) . ?
O42 H42 0.8400 . ?
O42 C19 1.400(14) . ?
C8 C13 1.478(15) . ?
C8 C9 1.391(14) . ?
C15 C6 1.274(16) . ?
C15 C16 1.448(14) . ?
C11 C12 1.410(14) . ?
C11 C10 1.36(2) . ?
C6 C5 1.444(18) . ?
C21 C1 1.417(18) . ?
C21 C27 1.392(15) . ?
C21 C20 1.529(15) . ?
C25 C26 1.342(14) . ?
C13 C12 1.342(15) . ?
C18 H18 0.9500 . ?
C18 C19 1.496(16) . ?
C43 C12 1.394(17) . ?
C43 N44 1.220(17) . ?
C1 C2 1.454(16) . ?
C1 C26 1.400(15) . ?
C4 H4 0.9500 . ?
C4 C3 1.477(16) . ?
C4 C5 1.32(2) . ?
C16 C3 1.381(15) . ?
C9 C10 1.383(17) . ?
C9 C45 1.49(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.513(16) . ?
C2 C19 1.561(17) . ?
C27 H27 0.9500 . ?
C23 C30 1.544(18) . ?
C23 C22 1.250(18) . ?
C33 C22 1.497(16) . ?
C33 C36 1.33(2) . ?
C33 C32 1.35(2) . ?
C5 H5 0.9500 . ?
C30 C31 1.29(2) . ?
C30 C38 1.45(2) . ?
C26 H26 0.9500 . ?
N46 C45 1.080(19) . ?
C31 C32 1.45(3) . ?
C36 N37 1.07(3) . ?
N39 C38 1.142(18) . ?
C19 C20 1.569(16) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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
C13 O14 C15 113.9(8) . . ?
C23 O24 C25 115.3(9) . . ?
C8 O7 C6 118.3(9) . . ?
C22 O29 C28 118.6(9) . . ?
C16 O17 C18 114.8(8) . . ?
O29 C28 C25 117.5(8) . . ?
O29 C28 C27 124.9(11) . . ?
C27 C28 C25 117.6(9) . . ?
C19 O42 H42 109.5 . . ?
O7 C8 C13 120.7(8) . . ?
O7 C8 C9 123.2(10) . . ?
C9 C8 C13 115.8(9) . . ?
O14 C15 C16 110.1(9) . . ?
C6 C15 O14 127.6(9) . . ?
C6 C15 C16 122.3(9) . . ?
F41 C11 C12 120.4(12) . . ?
C10 C11 F41 120.1(9) . . ?
C10 C11 C12 119.2(12) . . ?
O7 C6 C5 115.6(12) . . ?
C15 C6 O7 120.4(10) . . ?
C15 C6 C5 123.7(12) . . ?
C1 C21 C20 109.5(9) . . ?
C27 C21 C1 123.4(10) . . ?
C27 C21 C20 127.0(11) . . ?
O24 C25 C28 117.9(7) . . ?
C26 C25 O24 122.5(10) . . ?
C26 C25 C28 119.6(9) . . ?
O14 C13 C8 118.6(8) . . ?
C12 C13 O14 121.2(10) . . ?
C12 C13 C8 120.1(9) . . ?
O17 C18 H18 122.9 . . ?
O17 C18 C19 114.1(10) . . ?
C19 C18 H18 122.9 . . ?
N44 C43 C12 175.2(14) . . ?
C13 C12 C11 121.7(12) . . ?
C13 C12 C43 121.1(10) . . ?
C43 C12 C11 117.2(11) . . ?
C21 C1 C2 111.4(9) . . ?
C26 C1 C21 117.2(11) . . ?
C26 C1 C2 131.1(12) . . ?
C3 C4 H4 117.2 . . ?
C5 C4 H4 117.2 . . ?
C5 C4 C3 125.5(11) . . ?
O17 C16 C15 119.9(9) . . ?
C3 C16 O17 122.0(9) . . ?
C3 C16 C15 118.1(9) . . ?
C8 C9 C45 116.7(11) . . ?
C10 C9 C8 122.3(11) . . ?
C10 C9 C45 121.0(11) . . ?
C1 C2 H2 108.4 . . ?
C1 C2 C3 115.9(9) . . ?
C1 C2 C19 103.8(10) . . ?
C3 C2 H2 108.4 . . ?
C3 C2 C19 111.6(8) . . ?
C19 C2 H2 108.4 . . ?
C4 C3 C2 122.5(10) . . ?
C16 C3 C4 115.8(10) . . ?
C16 C3 C2 121.7(9) . . ?
F40 C10 C11 119.8(11) . . ?
F40 C10 C9 119.4(12) . . ?
C11 C10 C9 120.8(11) . . ?
C28 C27 C21 119.9(12) . . ?
C28 C27 H27 120.0 . . ?
C21 C27 H27 120.0 . . ?
O24 C23 C30 112.5(11) . . ?
C22 C23 O24 127.3(11) . . ?
C22 C23 C30 120.2(10) . . ?
C36 C33 C22 118.8(13) . . ?
C36 C33 C32 125.9(12) . . ?
C32 C33 C22 115.1(13) . . ?
C6 C5 H5 122.7 . . ?
C4 C5 C6 114.5(14) . . ?
C4 C5 H5 122.7 . . ?
C31 C30 C23 117.8(13) . . ?
C31 C30 C38 124.4(13) . . ?
C38 C30 C23 117.7(12) . . ?
O29 C22 C33 113.6(11) . . ?
C23 C22 O29 123.4(10) . . ?
C23 C22 C33 122.9(11) . . ?
C25 C26 C1 122.2(12) . . ?
C25 C26 H26 118.9 . . ?
C1 C26 H26 118.9 . . ?
F35 C31 C32 119.0(14) . . ?
C30 C31 F35 120.1(17) . . ?
C30 C31 C32 120.8(13) . . ?
N37 C36 C33 167(2) . . ?
O42 C19 C18 111.1(9) . . ?
O42 C19 C2 111.4(10) . . ?
O42 C19 C20 111.4(9) . . ?
C18 C19 C2 108.9(8) . . ?
C18 C19 C20 109.9(10) . . ?
C2 C19 C20 103.9(8) . . ?
N39 C38 C30 175.9(15) . . ?
F34 C32 C33 118.7(14) . . ?
F34 C32 C31 118.1(14) . . ?
C33 C32 C31 122.9(13) . . ?
N46 C45 C9 175.8(17) . . ?
C21 C20 C19 100.5(8) . . ?
C21 C20 H20A 111.7 . . ?
C21 C20 H20B 111.7 . . ?
C19 C20 H20A 111.7 . . ?
C19 C20 H20B 111.7 . . ?
H20A C20 H20B 109.4 . . ?

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
O14 C15 C6 O7 3.7(16) . . . . ?
O14 C15 C6 C5 178.0(9) . . . . ?
O14 C15 C16 O17 -2.4(11) . . . . ?
O14 C15 C16 C3 -179.7(8) . . . . ?
O14 C13 C12 C11 -177.7(10) . . . . ?
O14 C13 C12 C43 1.0(16) . . . . ?
O24 C25 C26 C1 -179.4(8) . . . . ?
O24 C23 C30 C31 177.2(11) . . . . ?
O24 C23 C30 C38 -4.9(13) . . . . ?
O24 C23 C22 O29 1.3(17) . . . . ?
O24 C23 C22 C33 -177.8(9) . . . . ?
F41 C11 C12 C13 176.1(9) . . . . ?
F41 C11 C12 C43 -2.5(16) . . . . ?
F41 C11 C10 F40 5.1(17) . . . . ?
F41 C11 C10 C9 -174.9(10) . . . . ?
O7 C8 C13 O14 -0.1(12) . . . . ?
O7 C8 C13 C12 -177.1(9) . . . . ?
O7 C8 C9 C10 178.2(10) . . . . ?
O7 C8 C9 C45 -1.0(16) . . . . ?
O7 C6 C5 C4 178.7(9) . . . . ?
O29 C28 C25 O24 -2.4(11) . . . . ?
O29 C28 C25 C26 176.3(8) . . . . ?
O29 C28 C27 C21 -178.2(9) . . . . ?
O17 C18 C19 O42 63.5(12) . . . . ?
O17 C18 C19 C2 -59.6(11) . . . . ?
O17 C18 C19 C20 -172.7(8) . . . . ?
O17 C16 C3 C4 -177.3(8) . . . . ?
O17 C16 C3 C2 4.0(15) . . . . ?
C28 O29 C22 C23 0.6(15) . . . . ?
C28 O29 C22 C33 179.7(8) . . . . ?
C28 C25 C26 C1 1.9(13) . . . . ?
F35 C31 C32 F34 4(2) . . . . ?
F35 C31 C32 C33 178.2(13) . . . . ?
O42 C19 C20 C21 -151.9(10) . . . . ?
C8 O7 C6 C15 -7.9(14) . . . . ?
C8 O7 C6 C5 177.4(8) . . . . ?
C8 C13 C12 C11 -0.7(16) . . . . ?
C8 C13 C12 C43 177.9(10) . . . . ?
C8 C9 C10 F40 178.2(10) . . . . ?
C8 C9 C10 C11 -1.8(17) . . . . ?
C15 O14 C13 C8 -4.0(11) . . . . ?
C15 O14 C13 C12 173.0(9) . . . . ?
C15 C6 C5 C4 4.1(15) . . . . ?
C15 C16 C3 C4 -0.1(13) . . . . ?
C15 C16 C3 C2 -178.8(9) . . . . ?
C6 O7 C8 C13 6.0(12) . . . . ?
C6 O7 C8 C9 -167.6(9) . . . . ?
C6 C15 C16 O17 -179.9(9) . . . . ?
C6 C15 C16 C3 2.8(14) . . . . ?
C21 C1 C2 C3 -138.4(10) . . . . ?
C21 C1 C2 C19 -15.7(11) . . . . ?
C21 C1 C26 C25 -0.5(14) . . . . ?
C25 O24 C23 C30 176.5(7) . . . . ?
C25 O24 C23 C22 -3.6(15) . . . . ?
C25 C28 C27 C21 -0.8(14) . . . . ?
C13 O14 C15 C6 2.4(13) . . . . ?
C13 O14 C15 C16 -175.0(7) . . . . ?
C13 C8 C9 C10 4.2(15) . . . . ?
C13 C8 C9 C45 -174.9(10) . . . . ?
C18 O17 C16 C15 160.4(9) . . . . ?
C18 O17 C16 C3 -22.4(13) . . . . ?
C18 C19 C20 C21 84.6(11) . . . . ?
C12 C11 C10 F40 177.9(10) . . . . ?
C12 C11 C10 C9 -2.1(17) . . . . ?
C1 C21 C27 C28 2.3(16) . . . . ?
C1 C21 C20 C19 23.5(12) . . . . ?
C1 C2 C3 C4 -73.3(13) . . . . ?
C1 C2 C3 C16 105.3(12) . . . . ?
C1 C2 C19 O42 149.9(8) . . . . ?
C1 C2 C19 C18 -87.3(10) . . . . ?
C1 C2 C19 C20 29.8(10) . . . . ?
C16 O17 C18 C19 51.6(11) . . . . ?
C16 C15 C6 O7 -179.3(8) . . . . ?
C16 C15 C6 C5 -5.0(16) . . . . ?
C9 C8 C13 O14 174.0(8) . . . . ?
C9 C8 C13 C12 -3.0(13) . . . . ?
C2 C1 C26 C25 -173.9(10) . . . . ?
C2 C19 C20 C21 -31.8(11) . . . . ?
C3 C4 C5 C6 -1.3(15) . . . . ?
C3 C2 C19 O42 -84.6(11) . . . . ?
C3 C2 C19 C18 38.2(12) . . . . ?
C3 C2 C19 C20 155.3(9) . . . . ?
C10 C11 C12 C13 3.4(17) . . . . ?
C10 C11 C12 C43 -175.3(10) . . . . ?
C27 C28 C25 O24 -180.0(9) . . . . ?
C27 C28 C25 C26 -1.3(13) . . . . ?
C27 C21 C1 C2 173.0(9) . . . . ?
C27 C21 C1 C26 -1.7(15) . . . . ?
C27 C21 C20 C19 -154.7(11) . . . . ?
C23 O24 C25 C28 3.8(11) . . . . ?
C23 O24 C25 C26 -174.8(9) . . . . ?
C23 C30 C31 F35 180.0(11) . . . . ?
C23 C30 C31 C32 4.6(19) . . . . ?
C5 C4 C3 C16 -0.4(15) . . . . ?
C5 C4 C3 C2 178.3(10) . . . . ?
C30 C23 C22 O29 -178.8(9) . . . . ?
C30 C23 C22 C33 2.2(16) . . . . ?
C30 C31 C32 F34 179.0(12) . . . . ?
C30 C31 C32 C33 -6(2) . . . . ?
C22 O29 C28 C25 0.1(12) . . . . ?
C22 O29 C28 C27 177.4(10) . . . . ?
C22 C23 C30 C31 -2.8(16) . . . . ?
C22 C23 C30 C38 175.2(11) . . . . ?
C22 C33 C36 N37 159(7) . . . . ?
C22 C33 C32 F34 179.9(11) . . . . ?
C22 C33 C32 C31 5.3(18) . . . . ?
C26 C1 C2 C3 35.3(16) . . . . ?
C26 C1 C2 C19 158.0(10) . . . . ?
C36 C33 C22 O29 2.0(15) . . . . ?
C36 C33 C22 C23 -178.8(12) . . . . ?
C36 C33 C32 F34 -5(2) . . . . ?
C36 C33 C32 C31 -179.7(14) . . . . ?
C19 C2 C3 C4 168.2(9) . . . . ?
C19 C2 C3 C16 -13.2(14) . . . . ?
C38 C30 C31 F35 2(2) . . . . ?
C38 C30 C31 C32 -173.2(12) . . . . ?
C32 C33 C22 O29 177.4(10) . . . . ?
C32 C33 C22 C23 -3.5(16) . . . . ?
C32 C33 C36 N37 -16(8) . . . . ?
C45 C9 C10 F40 -2.7(17) . . . . ?
C45 C9 C10 C11 177.3(12) . . . . ?
C20 C21 C1 C2 -5.4(12) . . . . ?
C20 C21 C1 C26 180.0(9) . . . . ?
C20 C21 C27 C28 -179.6(11) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.137 0.082 0.347 65.6 15.7 ?
2 0.137 0.582 0.153 65.6 15.7 ?
3 0.363 0.418 0.653 65.6 15.7 ?
4 0.637 -0.082 0.847 65.6 15.7 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.270
_oxdiff_exptl_absorpt_empirical_full_min 0.710
