# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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. 
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data_mo_zjb_285_a_0m
_database_code_depnum_ccdc_archive 'CCDC 2328809'
loop_
_audit_author_name
_audit_author_address
'Jun-Bo Zhao'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2024-01-27 deposited with the CCDC.	2024-07-25 downloaded from the CCDC.
;
_audit_creation_date             2024-01-15
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 I2 O2, 0.8[CHCl3]'
_chemical_formula_sum            'C23 H18 I2 O2'
_chemical_formula_weight         580.17
_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 0.0033 0.0016 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   16.5721(19)
_cell_length_b                   8.3586(8)
_cell_length_c                   17.0294(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.605(4)
_cell_angle_gamma                90
_cell_volume                     2356.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.616
_shelx_estimated_absorpt_T_min   0.500
_exptl_absorpt_coefficient_mu    2.682
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0926 before and 0.0632 after correction.
The Ratio of minimum to maximum transmission is 0.8211.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            53896
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_min         1.677
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4170
_reflns_number_total             5851
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.781
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         5851
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.068
_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)+(0.0787P)²+4.4748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1651
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
I1 I 0.51310(3) 0.25624(6) 0.96235(3) 0.08278(19) Uani 1 1 d . . . . .
I2 I 0.14432(3) 1.20989(5) 0.35350(2) 0.06633(16) Uani 1 1 d . . . . .
O1 O 0.55157(18) 0.6107(4) 0.59517(19) 0.0450(7) Uani 1 1 d . . . . .
O2 O 0.4139(2) 0.7792(6) 0.6025(2) 0.0663(11) Uani 1 1 d . . . . .
C1 C 0.5463(3) 0.3477(7) 0.8538(3) 0.0576(13) Uani 1 1 d . . . . .
C2 C 0.6146(4) 0.2852(7) 0.8196(4) 0.0668(16) Uani 1 1 d . . . . .
H2 H 0.646986 0.206977 0.846451 0.080 Uiso 1 1 calc R U . . .
C3 C 0.6344(3) 0.3386(7) 0.7461(4) 0.0596(13) Uani 1 1 d . . . . .
H3 H 0.679062 0.292590 0.721216 0.072 Uiso 1 1 calc R U . . .
C4 C 0.5894(3) 0.4603(6) 0.7078(3) 0.0474(11) Uani 1 1 d . . . . .
C5 C 0.6113(3) 0.5159(6) 0.6298(3) 0.0475(11) Uani 1 1 d . . . . .
C6 C 0.5562(3) 0.6657(6) 0.5207(3) 0.0447(10) Uani 1 1 d . . . . .
C7 C 0.4934(3) 0.7589(6) 0.4915(3) 0.0434(10) Uani 1 1 d . . . . .
H7 H 0.496298 0.793551 0.438594 0.052 Uiso 1 1 calc R U . . .
C8 C 0.4239(3) 0.8094(6) 0.5323(3) 0.0465(10) Uani 1 1 d . . . . .
C9 C 0.3605(3) 0.9037(6) 0.4871(3) 0.0423(9) Uani 1 1 d . . . . .
C10 C 0.3703(3) 0.9691(7) 0.4130(3) 0.0522(12) Uani 1 1 d . . . . .
H10 H 0.420036 0.954983 0.388175 0.063 Uiso 1 1 calc R U . . .
C11 C 0.3081(3) 1.0550(7) 0.3748(3) 0.0564(12) Uani 1 1 d . . . . .
H11 H 0.315198 1.098523 0.324077 0.068 Uiso 1 1 calc R U . . .
C12 C 0.2370(3) 1.0764(6) 0.4104(3) 0.0490(11) Uani 1 1 d . . . . .
C13 C 0.5017(3) 0.4661(7) 0.8167(3) 0.0584(13) Uani 1 1 d . . . . .
H13 H 0.456228 0.509777 0.841012 0.070 Uiso 1 1 calc R U . . .
C14 C 0.5228(3) 0.5224(6) 0.7439(3) 0.0475(11) Uani 1 1 d . . . . .
H14 H 0.491372 0.603986 0.718515 0.057 Uiso 1 1 calc R U . . .
C15 C 0.6780(3) 0.4868(7) 0.5906(3) 0.0551(13) Uani 1 1 d . . . . .
H15 H 0.720886 0.427863 0.615747 0.066 Uiso 1 1 calc R U . . .
C16 C 0.6862(3) 0.5417(6) 0.5126(3) 0.0520(12) Uani 1 1 d . . . . .
C17 C 0.6254(3) 0.6259(6) 0.4773(3) 0.0458(10) Uani 1 1 d . . . . .
C18 C 0.6271(3) 0.6805(8) 0.3933(3) 0.0630(15) Uani 1 1 d . . . . .
H18A H 0.635655 0.797669 0.392191 0.076 Uiso 1 1 calc R U . . .
H18B H 0.574207 0.657582 0.366355 0.076 Uiso 1 1 calc R U . . .
C19 C 0.6931(5) 0.5992(15) 0.3491(5) 0.114(3) Uani 1 1 d . . . . .
H19A H 0.674749 0.490788 0.333227 0.137 Uiso 1 1 calc R U . . .
H19B H 0.702608 0.660708 0.300718 0.137 Uiso 1 1 calc R U . . .
C20 C 0.7684(5) 0.5863(15) 0.3955(6) 0.120(3) Uani 1 1 d . . . . .
H20A H 0.789289 0.695462 0.406157 0.144 Uiso 1 1 calc R U . . .
H20B H 0.808182 0.530107 0.363782 0.144 Uiso 1 1 calc R U . . .
C21 C 0.7628(3) 0.5000(8) 0.4725(4) 0.0689(17) Uani 1 1 d . . . . .
H21A H 0.809970 0.528545 0.507440 0.083 Uiso 1 1 calc R U . . .
H21B H 0.764393 0.383139 0.463183 0.083 Uiso 1 1 calc R U . . .
C22 C 0.2252(3) 1.0159(7) 0.4840(3) 0.0538(12) Uani 1 1 d . . . . .
H22 H 0.175410 1.031487 0.508371 0.065 Uiso 1 1 calc R U . . .
C23 C 0.2876(3) 0.9316(7) 0.5219(3) 0.0500(11) Uani 1 1 d . . . . .
H23 H 0.280211 0.891752 0.573365 0.060 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
I1 C1 2.096(6) . ?
I2 C12 2.099(5) . ?
O1 C5 1.379(6) . ?
O1 C6 1.354(6) . ?
O2 C8 1.241(6) . ?
C1 C2 1.399(9) . ?
C1 C13 1.372(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.405(8) . ?
C4 C5 1.468(7) . ?
C4 C14 1.389(7) . ?
C5 C15 1.339(7) . ?
C6 C7 1.376(7) . ?
C6 C17 1.431(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.435(7) . ?
C8 C9 1.497(7) . ?
C9 C10 1.392(7) . ?
C9 C23 1.390(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.394(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.361(8) . ?
C12 C22 1.373(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.418(8) . ?
C16 C17 1.349(7) . ?
C16 C21 1.508(7) . ?
C17 C18 1.503(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.515(9) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.449(12) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.504(11) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22 0.9500 . ?
C22 C23 1.385(7) . ?
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
C6 O1 C5 121.6(4) . . ?
C2 C1 I1 118.8(4) . . ?
C13 C1 I1 120.9(5) . . ?
C13 C1 C2 120.4(5) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(6) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(5) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 120.1(5) . . ?
C14 C4 C3 118.8(5) . . ?
C14 C4 C5 121.1(5) . . ?
O1 C5 C4 111.5(4) . . ?
C15 C5 O1 119.0(5) . . ?
C15 C5 C4 129.6(5) . . ?
O1 C6 C7 117.2(4) . . ?
O1 C6 C17 119.1(4) . . ?
C7 C6 C17 123.7(5) . . ?
C6 C7 H7 116.5 . . ?
C6 C7 C8 127.1(5) . . ?
C8 C7 H7 116.5 . . ?
O2 C8 C7 123.5(5) . . ?
O2 C8 C9 118.7(4) . . ?
C7 C8 C9 117.8(4) . . ?
C10 C9 C8 124.3(4) . . ?
C23 C9 C8 118.2(4) . . ?
C23 C9 C10 117.5(5) . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.7(5) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(5) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 I2 119.6(4) . . ?
C11 C12 C22 121.3(5) . . ?
C22 C12 I2 119.1(4) . . ?
C1 C13 H13 119.8 . . ?
C1 C13 C14 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C4 C14 H14 119.8 . . ?
C13 C14 C4 120.5(5) . . ?
C13 C14 H14 119.8 . . ?
C5 C15 H15 119.2 . . ?
C5 C15 C16 121.6(5) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C21 117.9(5) . . ?
C17 C16 C15 119.0(4) . . ?
C17 C16 C21 123.1(5) . . ?
C6 C17 C18 118.2(5) . . ?
C16 C17 C6 119.4(5) . . ?
C16 C17 C18 122.4(4) . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C17 C18 C19 112.5(6) . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 C18 112.7(7) . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C19 C20 H20A 108.5 . . ?
C19 C20 H20B 108.5 . . ?
C19 C20 C21 115.2(8) . . ?
H20A C20 H20B 107.5 . . ?
C21 C20 H20A 108.5 . . ?
C21 C20 H20B 108.5 . . ?
C16 C21 H21A 109.3 . . ?
C16 C21 H21B 109.3 . . ?
C20 C21 C16 111.7(6) . . ?
C20 C21 H21A 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C12 C22 H22 120.7 . . ?
C12 C22 C23 118.7(5) . . ?
C23 C22 H22 120.7 . . ?
C9 C23 H23 119.0 . . ?
C22 C23 C9 122.0(5) . . ?
C22 C23 H23 119.0 . . ?

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
I1 C1 C2 C3 176.5(4) . . . . ?
I1 C1 C13 C14 -178.1(4) . . . . ?
I2 C12 C22 C23 -178.3(4) . . . . ?
O1 C5 C15 C16 -4.4(8) . . . . ?
O1 C6 C7 C8 2.3(7) . . . . ?
O1 C6 C17 C16 -3.4(7) . . . . ?
O1 C6 C17 C18 176.6(4) . . . . ?
O2 C8 C9 C10 168.3(5) . . . . ?
O2 C8 C9 C23 -9.9(7) . . . . ?
C1 C2 C3 C4 3.4(9) . . . . ?
C1 C13 C14 C4 -0.3(8) . . . . ?
C2 C1 C13 C14 1.6(8) . . . . ?
C2 C3 C4 C5 179.9(5) . . . . ?
C2 C3 C4 C14 -2.1(8) . . . . ?
C3 C4 C5 O1 167.8(4) . . . . ?
C3 C4 C5 C15 -11.9(8) . . . . ?
C3 C4 C14 C13 0.6(7) . . . . ?
C4 C5 C15 C16 175.2(5) . . . . ?
C5 O1 C6 C7 179.8(4) . . . . ?
C5 O1 C6 C17 -0.7(6) . . . . ?
C5 C4 C14 C13 178.5(5) . . . . ?
C5 C15 C16 C17 0.3(8) . . . . ?
C5 C15 C16 C21 -178.7(5) . . . . ?
C6 O1 C5 C4 -175.1(4) . . . . ?
C6 O1 C5 C15 4.6(7) . . . . ?
C6 C7 C8 O2 3.3(8) . . . . ?
C6 C7 C8 C9 -176.7(4) . . . . ?
C6 C17 C18 C19 -166.7(6) . . . . ?
C7 C6 C17 C16 176.1(5) . . . . ?
C7 C6 C17 C18 -3.9(7) . . . . ?
C7 C8 C9 C10 -11.6(7) . . . . ?
C7 C8 C9 C23 170.1(5) . . . . ?
C8 C9 C10 C11 179.8(5) . . . . ?
C8 C9 C23 C22 -179.2(5) . . . . ?
C9 C10 C11 C12 0.5(8) . . . . ?
C10 C9 C23 C22 2.4(8) . . . . ?
C10 C11 C12 I2 178.8(4) . . . . ?
C10 C11 C12 C22 0.5(8) . . . . ?
C11 C12 C22 C23 0.0(8) . . . . ?
C12 C22 C23 C9 -1.5(8) . . . . ?
C13 C1 C2 C3 -3.1(9) . . . . ?
C14 C4 C5 O1 -10.2(6) . . . . ?
C14 C4 C5 C15 170.2(5) . . . . ?
C15 C16 C17 C6 3.6(7) . . . . ?
C15 C16 C17 C18 -176.5(5) . . . . ?
C15 C16 C21 C20 -171.4(7) . . . . ?
C16 C17 C18 C19 13.3(8) . . . . ?
C17 C6 C7 C8 -177.2(5) . . . . ?
C17 C16 C21 C20 9.7(9) . . . . ?
C17 C18 C19 C20 -41.9(11) . . . . ?
C18 C19 C20 C21 56.9(13) . . . . ?
C19 C20 C21 C16 -39.5(11) . . . . ?
C21 C16 C17 C6 -177.5(5) . . . . ?
C21 C16 C17 C18 2.5(8) . . . . ?
C23 C9 C10 C11 -1.9(8) . . . . ?

_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 -0.250 0.059 0.250 235.4 90.2 '1.6 CHCl3'
2 0.250 -0.059 0.750 235.4 90.2 '1.6 CHCl3'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2328810'
loop_
_audit_author_name
_audit_author_address
'Jun-Bo Zhao'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2024-01-27 deposited with the CCDC.	2024-07-25 downloaded from the CCDC.
;
_audit_creation_date             2024-01-15
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H19 F3 O4'
_chemical_formula_sum            'C25 H19 F3 O4'
_chemical_formula_weight         440.40
_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 0.0033 0.0016 '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 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   9.6264(17)
_cell_length_b                   10.7417(18)
_cell_length_c                   11.025(2)
_cell_angle_alpha                97.196(6)
_cell_angle_beta                 113.780(6)
_cell_angle_gamma                92.477(6)
_cell_volume                     1029.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9609
_cell_measurement_temperature    300
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1164 before and 0.0656 after correction.
The Ratio of minimum to maximum transmission is 0.9378.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            38754
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_min         2.044
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3595
_reflns_number_total             5079
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5079
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.1031
_refine_ls_R_factor_gt           0.0815
_refine_ls_restrained_S_all      1.129
_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)+(0.1345P)²+0.4503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2446
_refine_ls_wR_factor_ref         0.2684
_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. Rigid bond restraints
 C2, F1, F2, F3, F1A, F2A, F3A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C2 \\sim F1 \\sim F2 \\sim F3 \\sim F1A \\sim F2A \\sim F3A: within 1.7A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
4. Rigid body (RIGU) restrains
 C2, F1, F2, F3, F1A, F2A, F3A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C8(H8), C12(H12), C13(H13), C16(H16), C23(H23), C24(H24),
 C28(H28), C29(H29)
6.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O1 O 0.54481(18) 0.50096(13) 0.21409(17) 0.0518(4) Uani 1 1 d . . . . .
C1 C 1.0544(4) 0.1717(3) -0.0227(4) 0.0890(11) Uani 1 1 d . . . . .
H1A H 1.007879 0.204775 -0.105233 0.133 Uiso 1 1 calc R U . . .
H1B H 1.094433 0.094017 -0.038836 0.133 Uiso 1 1 calc R U . . .
H1C H 1.135831 0.231471 0.041280 0.133 Uiso 1 1 calc R U . . .
O2 O 0.6616(3) 0.91809(19) 0.1193(3) 0.1015(9) Uani 1 1 d . . . . .
O3 O 0.4326(3) 0.31253(19) 0.2936(3) 0.0980(9) Uani 1 1 d . . . . .
C2 C -0.0462(5) 0.2146(4) 0.5462(5) 0.1004(9) Uani 1 1 d . U . . .
C3 C 0.0598(3) 0.2614(3) 0.4912(3) 0.0715(8) Uani 1 1 d . . . . .
C4 C 0.1200(3) 0.3861(3) 0.5281(3) 0.0656(7) Uani 1 1 d . . . . .
H4 H 0.094630 0.439909 0.587287 0.079 Uiso 1 1 calc R U . . .
C5 C 0.2184(3) 0.4304(2) 0.4764(3) 0.0583(6) Uani 1 1 d . . . . .
H5 H 0.259583 0.514349 0.501198 0.070 Uiso 1 1 calc R U . . .
C6 C 0.2560(3) 0.3505(2) 0.3877(3) 0.0545(6) Uani 1 1 d . . . . .
C7 C 0.3646(3) 0.3922(2) 0.3296(3) 0.0608(6) Uani 1 1 d . . . . .
C8 C 0.3785(3) 0.5246(2) 0.3182(3) 0.0547(6) Uani 1 1 d . . . . .
H8 H 0.322925 0.577187 0.350868 0.066 Uiso 1 1 calc R U . . .
C9 C 0.4658(3) 0.5791(2) 0.2639(2) 0.0494(5) Uani 1 1 d . . . . .
C10 C 0.6351(3) 0.54228(19) 0.1552(2) 0.0472(5) Uani 1 1 d . . . . .
C11 C 0.7145(3) 0.44064(19) 0.1199(2) 0.0481(5) Uani 1 1 d . . . . .
C12 C 0.6952(3) 0.3194(2) 0.1466(3) 0.0522(5) Uani 1 1 d . . . . .
H12 H 0.629095 0.302056 0.186173 0.063 Uiso 1 1 calc R U . . .
C13 C 0.7730(3) 0.2246(2) 0.1151(3) 0.0571(6) Uani 1 1 d . . . . .
H13 H 0.758682 0.143994 0.133255 0.068 Uiso 1 1 calc R U . . .
C14 C 0.8723(3) 0.2493(2) 0.0565(3) 0.0562(6) Uani 1 1 d . . . . .
O15 O 0.9431(2) 0.14896(17) 0.0289(2) 0.0752(6) Uani 1 1 d . . . . .
C16 C 0.6445(3) 0.6636(2) 0.1402(3) 0.0538(6) Uani 1 1 d . . . . .
H16 H 0.701864 0.691217 0.096326 0.065 Uiso 1 1 calc R U . . .
C17 C 0.5663(3) 0.7505(2) 0.1916(3) 0.0517(5) Uani 1 1 d . . . . .
C18 C 0.4819(3) 0.7120(2) 0.2559(2) 0.0506(5) Uani 1 1 d . . . . .
C19 C 0.4042(4) 0.8023(2) 0.3175(3) 0.0659(7) Uani 1 1 d . . . . .
H19A H 0.421167 0.784232 0.406114 0.079 Uiso 1 1 calc R U . . .
H19B H 0.295176 0.791157 0.262777 0.079 Uiso 1 1 calc R U . . .
C20 C 0.4658(7) 0.9382(3) 0.3283(5) 0.1272(19) Uani 1 1 d . . . . .
H20A H 0.393713 0.992443 0.342043 0.153 Uiso 1 1 calc R U . . .
H20B H 0.560225 0.956412 0.408596 0.153 Uiso 1 1 calc R U . . .
C21 C 0.4945(5) 0.9734(3) 0.2219(5) 0.0960(12) Uani 1 1 d . . . . .
H21A H 0.549995 1.056906 0.250289 0.115 Uiso 1 1 calc R U . . .
H21B H 0.397834 0.978583 0.147708 0.115 Uiso 1 1 calc R U . . .
C22 C 0.5831(3) 0.8859(2) 0.1738(3) 0.0691(7) Uani 1 1 d . . . . .
C23 C 0.0973(4) 0.1807(3) 0.4040(4) 0.0806(9) Uani 1 1 d . . . . .
H23 H 0.055581 0.096931 0.379016 0.097 Uiso 1 1 calc R U . . .
C24 C 0.1971(4) 0.2251(3) 0.3540(3) 0.0701(7) Uani 1 1 d . . . . .
H24 H 0.224921 0.170324 0.297320 0.084 Uiso 1 1 calc R U . . .
C28 C 0.8113(3) 0.4622(2) 0.0575(3) 0.0701(8) Uani 1 1 d . . . . .
H28 H 0.823306 0.541874 0.036318 0.084 Uiso 1 1 calc R U . . .
C29 C 0.8896(4) 0.3682(2) 0.0265(4) 0.0722(8) Uani 1 1 d . . . . .
H29 H 0.954275 0.384910 -0.014678 0.087 Uiso 1 1 calc R U . . .
F1 F 0.0165(7) 0.1301(4) 0.6290(5) 0.1236(15) Uani 0.651(5) 1 d . U P A 1
F2 F -0.0596(5) 0.3043(4) 0.6443(5) 0.1135(13) Uani 0.651(5) 1 d . U P A 1
F3 F -0.1744(7) 0.1771(9) 0.4668(7) 0.180(3) Uani 0.651(5) 1 d . U P A 1
F1A F -0.0095(15) 0.1973(14) 0.6497(12) 0.161(3) Uani 0.349(5) 1 d . U P A 2
F2A F -0.1886(9) 0.2609(7) 0.4834(10) 0.107(2) Uani 0.349(5) 1 d . U P A 2
F3A F -0.1259(9) 0.0900(7) 0.4708(11) 0.116(2) Uani 0.349(5) 1 d . U P A 2


_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
O1 C9 1.364(2) . ?
O1 C10 1.367(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 O15 1.426(3) . ?
O2 C22 1.202(3) . ?
O3 C7 1.222(3) . ?
C2 C3 1.481(4) . ?
C2 F1 1.354(6) . ?
C2 F2 1.407(6) . ?
C2 F3 1.203(7) . ?
C2 F1A 1.094(11) . ?
C2 F2A 1.409(9) . ?
C2 F3A 1.479(9) . ?
C3 C4 1.379(4) . ?
C3 C23 1.380(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(3) . ?
C6 C7 1.509(3) . ?
C6 C24 1.383(4) . ?
C7 C8 1.449(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.363(3) . ?
C9 C18 1.447(3) . ?
C10 C11 1.461(3) . ?
C10 C16 1.338(3) . ?
C11 C12 1.391(3) . ?
C11 C28 1.389(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(3) . ?
C14 O15 1.367(3) . ?
C14 C29 1.379(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.424(3) . ?
C17 C18 1.357(3) . ?
C17 C22 1.503(3) . ?
C18 C19 1.506(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.523(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.400(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.484(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.381(4) . ?
C24 H24 0.9300 . ?
C28 H28 0.9300 . ?
C28 C29 1.375(3) . ?
C29 H29 0.9300 . ?

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
C9 O1 C10 123.03(17) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O15 C1 H1A 109.5 . . ?
O15 C1 H1B 109.5 . . ?
O15 C1 H1C 109.5 . . ?
F1 C2 C3 111.1(4) . . ?
F1 C2 F2 95.9(4) . . ?
F2 C2 C3 113.0(3) . . ?
F3 C2 C3 116.8(5) . . ?
F3 C2 F1 111.7(5) . . ?
F3 C2 F2 106.3(5) . . ?
F1A C2 C3 123.5(8) . . ?
F1A C2 F2A 118.8(9) . . ?
F1A C2 F3A 101.2(9) . . ?
F2A C2 C3 109.3(4) . . ?
F2A C2 F3A 85.6(5) . . ?
F3A C2 C3 110.6(4) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 C23 120.7(2) . . ?
C23 C3 C2 120.1(3) . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 123.1(2) . . ?
C24 C6 C5 119.3(2) . . ?
C24 C6 C7 117.5(2) . . ?
O3 C7 C6 118.2(2) . . ?
O3 C7 C8 124.6(2) . . ?
C8 C7 C6 117.2(2) . . ?
C7 C8 H8 117.1 . . ?
C9 C8 C7 125.8(2) . . ?
C9 C8 H8 117.1 . . ?
O1 C9 C18 117.86(18) . . ?
C8 C9 O1 116.71(19) . . ?
C8 C9 C18 125.4(2) . . ?
O1 C10 C11 111.41(17) . . ?
C16 C10 O1 119.84(19) . . ?
C16 C10 C11 128.7(2) . . ?
C12 C11 C10 121.30(19) . . ?
C28 C11 C10 120.79(19) . . ?
C28 C11 C12 117.9(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
O15 C14 C13 115.6(2) . . ?
O15 C14 C29 124.8(2) . . ?
C29 C14 C13 119.5(2) . . ?
C14 O15 C1 117.6(2) . . ?
C10 C16 H16 120.1 . . ?
C10 C16 C17 119.9(2) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C22 117.5(2) . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 C22 121.6(2) . . ?
C9 C18 C19 119.4(2) . . ?
C17 C18 C9 118.27(19) . . ?
C17 C18 C19 122.3(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 C20 110.7(2) . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C19 C20 H20A 107.6 . . ?
C19 C20 H20B 107.6 . . ?
H20A C20 H20B 107.1 . . ?
C21 C20 C19 118.7(3) . . ?
C21 C20 H20A 107.6 . . ?
C21 C20 H20B 107.6 . . ?
C20 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
C20 C21 C22 114.2(3) . . ?
H21A C21 H21B 107.6 . . ?
C22 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
O2 C22 C17 120.2(2) . . ?
O2 C22 C21 123.2(2) . . ?
C21 C22 C17 116.5(2) . . ?
C3 C23 H23 120.2 . . ?
C3 C23 C24 119.6(3) . . ?
C24 C23 H23 120.2 . . ?
C6 C24 H24 119.8 . . ?
C23 C24 C6 120.4(3) . . ?
C23 C24 H24 119.8 . . ?
C11 C28 H28 119.3 . . ?
C29 C28 C11 121.5(2) . . ?
C29 C28 H28 119.3 . . ?
C14 C29 H29 120.0 . . ?
C28 C29 C14 120.0(2) . . ?
C28 C29 H29 120.0 . . ?

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
O1 C9 C18 C17 4.3(3) . . . . ?
O1 C9 C18 C19 -176.2(2) . . . . ?
O1 C10 C11 C12 -0.3(3) . . . . ?
O1 C10 C11 C28 179.3(2) . . . . ?
O1 C10 C16 C17 3.1(4) . . . . ?
O3 C7 C8 C9 1.4(5) . . . . ?
C2 C3 C4 C5 -179.6(3) . . . . ?
C2 C3 C23 C24 -179.6(3) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C3 C23 C24 C6 -1.9(5) . . . . ?
C4 C3 C23 C24 0.5(5) . . . . ?
C4 C5 C6 C7 -178.9(2) . . . . ?
C4 C5 C6 C24 -1.6(4) . . . . ?
C5 C6 C7 O3 154.4(3) . . . . ?
C5 C6 C7 C8 -26.7(4) . . . . ?
C5 C6 C24 C23 2.4(4) . . . . ?
C6 C7 C8 C9 -177.4(2) . . . . ?
C7 C6 C24 C23 179.9(3) . . . . ?
C7 C8 C9 O1 1.1(4) . . . . ?
C7 C8 C9 C18 -178.4(3) . . . . ?
C8 C9 C18 C17 -176.2(2) . . . . ?
C8 C9 C18 C19 3.3(4) . . . . ?
C9 O1 C10 C11 175.9(2) . . . . ?
C9 O1 C10 C16 -2.4(4) . . . . ?
C9 C18 C19 C20 166.2(3) . . . . ?
C10 O1 C9 C8 179.1(2) . . . . ?
C10 O1 C9 C18 -1.3(3) . . . . ?
C10 C11 C12 C13 -178.8(2) . . . . ?
C10 C11 C28 C29 178.4(3) . . . . ?
C10 C16 C17 C18 0.0(4) . . . . ?
C10 C16 C17 C22 179.0(2) . . . . ?
C11 C10 C16 C17 -174.9(2) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C11 C28 C29 C14 0.4(5) . . . . ?
C12 C11 C28 C29 -1.9(5) . . . . ?
C12 C13 C14 O15 -179.8(2) . . . . ?
C12 C13 C14 C29 -1.8(4) . . . . ?
C13 C14 O15 C1 -175.7(3) . . . . ?
C13 C14 C29 C28 1.5(5) . . . . ?
O15 C14 C29 C28 179.3(3) . . . . ?
C16 C10 C11 C12 177.9(3) . . . . ?
C16 C10 C11 C28 -2.5(4) . . . . ?
C16 C17 C18 C9 -3.7(4) . . . . ?
C16 C17 C18 C19 176.9(2) . . . . ?
C16 C17 C22 O2 -0.9(5) . . . . ?
C16 C17 C22 C21 177.0(3) . . . . ?
C17 C18 C19 C20 -14.3(4) . . . . ?
C18 C17 C22 O2 178.2(3) . . . . ?
C18 C17 C22 C21 -3.9(5) . . . . ?
C18 C19 C20 C21 40.6(6) . . . . ?
C19 C20 C21 C22 -48.1(7) . . . . ?
C20 C21 C22 O2 -153.9(4) . . . . ?
C20 C21 C22 C17 28.3(5) . . . . ?
C22 C17 C18 C9 177.3(2) . . . . ?
C22 C17 C18 C19 -2.1(4) . . . . ?
C23 C3 C4 C5 0.3(5) . . . . ?
C24 C6 C7 O3 -23.0(4) . . . . ?
C24 C6 C7 C8 155.9(3) . . . . ?
C28 C11 C12 C13 1.6(4) . . . . ?
C29 C14 O15 C1 6.4(5) . . . . ?
F1 C2 C3 C4 -113.1(4) . . . . ?
F1 C2 C3 C23 66.9(6) . . . . ?
F2 C2 C3 C4 -6.6(5) . . . . ?
F2 C2 C3 C23 173.5(4) . . . . ?
F3 C2 C3 C4 117.1(7) . . . . ?
F3 C2 C3 C23 -62.8(7) . . . . ?
F1A C2 C3 C4 -73.9(12) . . . . ?
F1A C2 C3 C23 106.2(12) . . . . ?
F2A C2 C3 C4 73.7(6) . . . . ?
F2A C2 C3 C23 -106.2(6) . . . . ?
F3A C2 C3 C4 166.3(5) . . . . ?
F3A C2 C3 C23 -13.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
