# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2323256'
loop_
_audit_author_name
_audit_author_address
'weining zhao'
;Shenzhen Technology University
China
;
_audit_update_record             
;
2024-01-03 deposited with the CCDC.	2024-02-05 downloaded from the CCDC.
;
_audit_creation_date             2024-01-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 F O'
_chemical_formula_sum            'C20 H15 F O'
_chemical_formula_weight         290.32
_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'
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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   16.4099(16)
_cell_length_b                   10.0684(10)
_cell_length_c                   18.6788(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3086.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2220
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.77
_cell_measurement_theta_min      18.11
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.865
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.3678
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1566 before and 0.0864 after correction.
The Ratio of minimum to maximum transmission is 0.4886.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15338
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.756
_diffrn_reflns_theta_max         66.756
_diffrn_reflns_theta_min         4.735
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2034
_reflns_number_total             2713
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2713
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0822
_refine_ls_restrained_S_all      1.082
_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)+(0.1512P)²+0.2314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2170
_refine_ls_wR_factor_ref         0.2324
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C1-F1A = C11-F1B
 1.36 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(F1A) = Uanis(F1B)
4. Others
 Sof(H1)=Sof(F1B)=1-FVAR(1)
 Sof(H11)=Sof(F1A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_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
C1 C 0.1289(3) 0.7786(4) 0.06818(17) 0.1080(12) Uani 1 1 d D . . . .
H1 H 0.0920 0.7965 0.0302 0.130 Uiso 0.643(4) 1 calc R U P A 2
C2 C 0.1073(2) 0.6939(4) 0.1201(2) 0.1071(11) Uani 1 1 d . . . . .
H2 H 0.0546 0.6547 0.1194 0.129 Uiso 1 1 calc R U . . .
C3 C 0.16147(19) 0.6630(3) 0.17489(17) 0.0862(8) Uani 1 1 d . . . . .
H3 H 0.1461 0.6014 0.2110 0.103 Uiso 1 1 calc R U . . .
C4 C 0.23771(15) 0.7217(2) 0.17700(12) 0.0606(6) Uani 1 1 d . . . . .
C5 C 0.25713(19) 0.8124(3) 0.12437(14) 0.0850(8) Uani 1 1 d . . . . .
H5 H 0.3081 0.8570 0.1260 0.102 Uiso 1 1 calc R U . . .
C6 C 0.2030(2) 0.8395(4) 0.06905(17) 0.1074(11) Uani 1 1 d . . . . .
H6 H 0.2176 0.9000 0.0322 0.129 Uiso 1 1 calc R U . . .
C7 C 0.29654(14) 0.68510(17) 0.23679(10) 0.0562(6) Uani 1 1 d . . . . .
H7 H 0.2816 0.5938 0.2533 0.067 Uiso 1 1 calc R U . . .
C8 C 0.38491(14) 0.67949(18) 0.21186(10) 0.0549(6) Uani 1 1 d . . . . .
C9 C 0.41562(16) 0.5627(2) 0.18322(12) 0.0677(6) Uani 1 1 d . . . . .
H9 H 0.3820 0.4859 0.1821 0.081 Uiso 1 1 calc R U . . .
C10 C 0.49373(19) 0.5553(3) 0.15630(15) 0.0837(8) Uani 1 1 d . . . . .
H10 H 0.5137 0.4751 0.1362 0.100 Uiso 1 1 calc R U . . .
C11 C 0.54145(18) 0.6654(3) 0.15923(16) 0.0870(8) Uani 1 1 d D . . . .
H11 H 0.5954 0.6606 0.1409 0.104 Uiso 0.357(4) 1 calc R U P A 1
C12 C 0.51478(19) 0.7824(3) 0.18743(16) 0.0866(8) Uani 1 1 d . . . . .
H12 H 0.5495 0.8578 0.1888 0.104 Uiso 1 1 calc R U . . .
C13 C 0.43589(17) 0.7894(2) 0.21413(14) 0.0702(7) Uani 1 1 d . . . . .
H13 H 0.4166 0.8703 0.2342 0.084 Uiso 1 1 calc R U . . .
C14 C 0.28934(17) 0.77638(19) 0.30120(12) 0.0640(6) Uani 1 1 d . . . . .
C15 C 0.32934(15) 0.7366(2) 0.36966(11) 0.0616(6) Uani 1 1 d . . . . .
C16 C 0.35366(17) 0.6072(2) 0.38360(13) 0.0716(7) Uani 1 1 d . . . . .
H16 H 0.3438 0.5394 0.3493 0.086 Uiso 1 1 calc R U . . .
C17 C 0.39223(18) 0.5766(3) 0.44731(15) 0.0894(9) Uani 1 1 d . . . . .
H17 H 0.4078 0.4875 0.4569 0.107 Uiso 1 1 calc R U . . .
C18 C 0.4080(2) 0.6735(4) 0.49643(15) 0.0997(10) Uani 1 1 d . . . . .
H18 H 0.4358 0.6519 0.5395 0.120 Uiso 1 1 calc R U . . .
C19 C 0.3842(2) 0.8012(4) 0.48394(16) 0.0983(10) Uani 1 1 d . . . . .
H19 H 0.3949 0.8681 0.5185 0.118 Uiso 1 1 calc R U . . .
C20 C 0.34449(19) 0.8333(3) 0.42126(13) 0.0809(8) Uani 1 1 d . . . . .
H20 H 0.3273 0.9222 0.4132 0.097 Uiso 1 1 calc R U . . .
F1A F 0.0855(3) 0.8234(7) 0.0128(3) 0.1297(11) Uani 0.357(4) 1 d D . P A 1
F1B F 0.61824(19) 0.6648(4) 0.1340(2) 0.1297(11) Uani 0.643(4) 1 d D . P A 2
O1 O 0.25507(17) 0.88217(18) 0.29667(9) 0.1064(8) Uani 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
C1 H1 0.9500 . ?
C1 C2 1.339(6) . ?
C1 C6 1.363(6) . ?
C1 F1A 1.335(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(4) . ?
C4 C5 1.379(3) . ?
C4 C7 1.522(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(4) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.524(3) . ?
C7 C14 1.519(3) . ?
C8 C9 1.387(3) . ?
C8 C13 1.388(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.358(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.363(4) . ?
C11 F1B 1.345(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.492(3) . ?
C14 O1 1.207(3) . ?
C15 C16 1.387(3) . ?
C15 C20 1.392(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.364(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.365(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.378(5) . ?
C20 H20 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
C2 C1 H1 119.5 . . ?
C2 C1 C6 121.0(3) . . ?
C6 C1 H1 119.5 . . ?
F1A C1 C2 129.5(5) . . ?
F1A C1 C6 109.5(5) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C7 119.4(2) . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 C7 122.5(2) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C4 C7 H7 107.1 . . ?
C4 C7 C8 112.85(17) . . ?
C8 C7 H7 107.1 . . ?
C14 C7 C4 112.68(17) . . ?
C14 C7 H7 107.1 . . ?
C14 C7 C8 109.78(19) . . ?
C9 C8 C7 119.68(19) . . ?
C9 C8 C13 118.0(2) . . ?
C13 C8 C7 122.31(18) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.6(2) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.7 . . ?
C11 C10 C9 118.5(2) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 118.8 . . ?
C10 C11 C12 122.4(3) . . ?
C12 C11 H11 118.8 . . ?
F1B C11 C10 121.5(3) . . ?
F1B C11 C12 116.1(3) . . ?
C11 C12 H12 120.6 . . ?
C11 C12 C13 118.8(3) . . ?
C13 C12 H12 120.6 . . ?
C8 C13 C12 120.7(2) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C7 118.84(18) . . ?
O1 C14 C7 121.0(2) . . ?
O1 C14 C15 120.11(19) . . ?
C16 C15 C14 122.64(19) . . ?
C16 C15 C20 118.4(2) . . ?
C20 C15 C14 118.9(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.5(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.3(3) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.1(3) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.5(3) . . ?
C19 C20 H20 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.3(5) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C2 C3 C4 C7 -179.1(2) . . . . ?
C3 C4 C5 C6 -2.8(4) . . . . ?
C3 C4 C7 C8 143.4(2) . . . . ?
C3 C4 C7 C14 -91.5(3) . . . . ?
C4 C5 C6 C1 2.1(5) . . . . ?
C4 C7 C8 C9 -87.2(2) . . . . ?
C4 C7 C8 C13 90.3(2) . . . . ?
C4 C7 C14 C15 166.9(2) . . . . ?
C4 C7 C14 O1 -16.4(3) . . . . ?
C5 C4 C7 C8 -36.9(3) . . . . ?
C5 C4 C7 C14 88.1(3) . . . . ?
C6 C1 C2 C3 -2.1(6) . . . . ?
C7 C4 C5 C6 177.5(3) . . . . ?
C7 C8 C9 C10 176.3(2) . . . . ?
C7 C8 C13 C12 -176.6(2) . . . . ?
C7 C14 C15 C16 -17.8(3) . . . . ?
C7 C14 C15 C20 160.9(2) . . . . ?
C8 C7 C14 C15 -66.4(2) . . . . ?
C8 C7 C14 O1 110.3(3) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C8 C13 C12 1.0(3) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C9 C10 C11 F1B 179.9(3) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C8 -0.3(4) . . . . ?
C13 C8 C9 C10 -1.3(3) . . . . ?
C14 C7 C8 C9 146.22(19) . . . . ?
C14 C7 C8 C13 -36.3(3) . . . . ?
C14 C15 C16 C17 178.4(2) . . . . ?
C14 C15 C20 C19 -177.5(3) . . . . ?
C15 C16 C17 C18 -1.2(4) . . . . ?
C16 C15 C20 C19 1.3(4) . . . . ?
C16 C17 C18 C19 1.6(5) . . . . ?
C17 C18 C19 C20 -0.5(5) . . . . ?
C18 C19 C20 C15 -0.9(5) . . . . ?
C20 C15 C16 C17 -0.3(4) . . . . ?
F1A C1 C2 C3 -177.9(5) . . . . ?
F1A C1 C6 C5 177.0(4) . . . . ?
F1B C11 C12 C13 179.8(3) . . . . ?
O1 C14 C15 C16 165.4(3) . . . . ?
O1 C14 C15 C20 -15.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
