# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_hlf006
_database_code_depnum_ccdc_archive 'CCDC 2067319'
loop_
_audit_author_name
_audit_author_address
'Wang Zhen'
;Chongqing Universuty
China
;
_audit_update_record             
;
2021-03-01 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 F O5'
_chemical_formula_sum            'C23 H21 F O5'
_chemical_formula_weight         396.40

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'
O O 0.0492 0.0322 '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'

_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'

_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. 
;

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                   8.5243(2)
_cell_length_b                   14.7793(4)
_cell_length_c                   15.8032(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1990.94(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    145(2)
_cell_measurement_reflns_used    9099
_cell_measurement_theta_min      4.10
_cell_measurement_theta_max      80.30

_exptl_crystal_description       triagnle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.097
_exptl_absorpt_coefficient_mu    0.824
_shelx_estimated_absorpt_T_min   0.784
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8576
_exptl_absorpt_correction_T_max  0.9541
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      145(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38786
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.095
_diffrn_reflns_theta_max         80.744
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4317
_reflns_number_gt                4148
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.998

_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. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+0.5303P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1753 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4317
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.90293(12) 0.41924(8) 0.26835(7) 0.0222(2) Uani 1 1 d . . . . .
O1 O 0.48291(15) 0.41665(9) 0.30507(8) 0.0187(3) Uani 1 1 d . . . . .
O2 O 0.80844(17) 0.54020(11) 0.15578(9) 0.0273(3) Uani 1 1 d . . . . .
O3 O 0.72845(16) 0.32477(10) 0.50922(8) 0.0212(3) Uani 1 1 d . . . . .
O4 O 0.4782(2) 0.30511(13) 0.55128(12) 0.0405(4) Uani 1 1 d . . . . .
O5 O 0.66923(16) 0.33256(9) 0.37123(8) 0.0198(3) Uani 1 1 d . . . . .
C1 C 0.4355(2) 0.47987(12) 0.24660(11) 0.0173(4) Uani 1 1 d . . . . .
C2 C 0.2743(2) 0.49314(13) 0.23900(13) 0.0206(4) Uani 1 1 d . . . . .
H2A H 0.203130 0.458764 0.272240 0.025 Uiso 1 1 calc R U . . .
C3 C 0.2194(2) 0.55726(13) 0.18221(13) 0.0229(4) Uani 1 1 d . . . . .
H3A H 0.109615 0.567048 0.177198 0.027 Uiso 1 1 calc R U . . .
C4 C 0.3222(2) 0.60759(13) 0.13236(13) 0.0234(4) Uani 1 1 d . . . . .
H4A H 0.282823 0.651698 0.094121 0.028 Uiso 1 1 calc R U . . .
C5 C 0.4821(2) 0.59281(13) 0.13901(12) 0.0216(4) Uani 1 1 d . . . . .
H5A H 0.552619 0.625972 0.104302 0.026 Uiso 1 1 calc R U . . .
C6 C 0.5404(2) 0.52906(13) 0.19681(11) 0.0179(3) Uani 1 1 d . . . . .
C7 C 0.7100(2) 0.51217(12) 0.20487(12) 0.0185(4) Uani 1 1 d . . . . .
C8 C 0.7558(2) 0.45817(13) 0.28306(11) 0.0174(3) Uani 1 1 d . . . . .
C9 C 0.6388(2) 0.37956(12) 0.29660(11) 0.0174(3) Uani 1 1 d . . . . .
C10 C 0.6483(2) 0.31001(12) 0.22668(12) 0.0197(4) Uani 1 1 d . . . . .
H10A H 0.744643 0.278692 0.219418 0.024 Uiso 1 1 calc R U . . .
C11 C 0.5307(2) 0.28963(13) 0.17455(12) 0.0216(4) Uani 1 1 d . . . . .
H11A H 0.435028 0.321620 0.182087 0.026 Uiso 1 1 calc R U . . .
C12 C 0.5358(2) 0.22198(13) 0.10634(12) 0.0214(4) Uani 1 1 d . . . . .
C13 C 0.4216(3) 0.22546(15) 0.04301(14) 0.0295(4) Uani 1 1 d . . . . .
H13A H 0.342565 0.270715 0.045157 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4224(3) 0.16338(17) -0.02317(15) 0.0354(5) Uani 1 1 d . . . . .
H14A H 0.345008 0.167113 -0.066283 0.042 Uiso 1 1 calc R U . . .
C15 C 0.5351(3) 0.09638(17) -0.02651(15) 0.0344(5) Uani 1 1 d . . . . .
H15A H 0.535494 0.054068 -0.071756 0.041 Uiso 1 1 calc R U . . .
C16 C 0.6478(3) 0.09125(15) 0.03664(15) 0.0315(5) Uani 1 1 d . . . . .
H16A H 0.724905 0.044865 0.034864 0.038 Uiso 1 1 calc R U . . .
C17 C 0.6486(3) 0.15356(13) 0.10247(13) 0.0254(4) Uani 1 1 d . . . . .
H17A H 0.726578 0.149599 0.145256 0.031 Uiso 1 1 calc R U . . .
C21 C 0.8904(3) 0.59406(14) 0.35170(14) 0.0283(4) Uani 1 1 d . . . . .
H21A H 0.864910 0.631266 0.302249 0.042 Uiso 1 1 calc R U . . .
H21B H 0.890908 0.632043 0.402537 0.042 Uiso 1 1 calc R U . . .
H21C H 0.994177 0.566713 0.344063 0.042 Uiso 1 1 calc R U . . .
C22 C 0.7672(2) 0.51923(13) 0.36151(12) 0.0199(4) Uani 1 1 d . . . . .
H22A H 0.662713 0.548463 0.370537 0.024 Uiso 1 1 calc R U . . .
C23 C 0.8028(2) 0.45947(13) 0.43819(12) 0.0219(4) Uani 1 1 d . . . . .
H23A H 0.907264 0.431165 0.431389 0.026 Uiso 1 1 calc R U . . .
H23B H 0.804661 0.496961 0.490091 0.026 Uiso 1 1 calc R U . . .
C24 C 0.6796(2) 0.38699(13) 0.44663(12) 0.0195(4) Uani 1 1 d . . . . .
H24A H 0.575403 0.413811 0.461248 0.023 Uiso 1 1 calc R U . . .
C25 C 0.6143(3) 0.28760(14) 0.55845(13) 0.0252(4) Uani 1 1 d . . . . .
C26 C 0.6859(3) 0.22278(17) 0.62008(16) 0.0391(6) Uani 1 1 d . . . . .
H26A H 0.799863 0.221500 0.612163 0.059 Uiso 1 1 calc R U . . .
H26B H 0.661678 0.242252 0.677908 0.059 Uiso 1 1 calc R U . . .
H26C H 0.642892 0.162126 0.610551 0.059 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 C8 1.399(2) . ?
O1 C1 1.375(2) . ?
O1 C9 1.444(2) . ?
O2 C7 1.215(2) . ?
O3 C25 1.361(2) . ?
O3 C24 1.413(2) . ?
O4 C25 1.194(3) . ?
O5 C9 1.393(2) . ?
O5 C24 1.440(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.396(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.393(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.403(3) . ?
C6 C7 1.473(2) . ?
C7 C8 1.522(2) . ?
C8 C22 1.536(2) . ?
C8 C9 1.546(2) . ?
C9 C10 1.511(2) . ?
C10 C11 1.332(3) . ?
C11 C12 1.471(3) . ?
C12 C17 1.397(3) . ?
C12 C13 1.397(3) . ?
C13 C14 1.391(3) . ?
C14 C15 1.381(4) . ?
C15 C16 1.387(3) . ?
C16 C17 1.389(3) . ?
C21 C22 1.533(3) . ?
C22 C23 1.530(3) . ?
C23 C24 1.506(3) . ?
C25 C26 1.496(3) . ?

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
C1 O1 C9 117.80(14) . . ?
C25 O3 C24 116.89(16) . . ?
C9 O5 C24 115.68(13) . . ?
O1 C1 C2 116.34(16) . . ?
O1 C1 C6 122.98(16) . . ?
C2 C1 C6 120.68(17) . . ?
C3 C2 C1 119.03(18) . . ?
C2 C3 C4 121.21(18) . . ?
C5 C4 C3 119.47(19) . . ?
C4 C5 C6 120.28(18) . . ?
C1 C6 C5 119.30(17) . . ?
C1 C6 C7 119.49(17) . . ?
C5 C6 C7 121.20(17) . . ?
O2 C7 C6 124.37(18) . . ?
O2 C7 C8 121.33(17) . . ?
C6 C7 C8 114.27(16) . . ?
F1 C8 C7 108.10(14) . . ?
F1 C8 C22 108.62(14) . . ?
C7 C8 C22 111.30(15) . . ?
F1 C8 C9 107.00(14) . . ?
C7 C8 C9 109.92(14) . . ?
C22 C8 C9 111.73(14) . . ?
O5 C9 O1 106.39(14) . . ?
O5 C9 C10 105.66(14) . . ?
O1 C9 C10 112.03(14) . . ?
O5 C9 C8 111.81(14) . . ?
O1 C9 C8 108.76(14) . . ?
C10 C9 C8 112.05(14) . . ?
C11 C10 C9 124.47(18) . . ?
C10 C11 C12 125.79(19) . . ?
C17 C12 C13 118.36(19) . . ?
C17 C12 C11 122.99(18) . . ?
C13 C12 C11 118.64(19) . . ?
C14 C13 C12 120.7(2) . . ?
C15 C14 C13 120.3(2) . . ?
C14 C15 C16 119.6(2) . . ?
C15 C16 C17 120.4(2) . . ?
C16 C17 C12 120.6(2) . . ?
C23 C22 C21 111.14(16) . . ?
C23 C22 C8 108.21(15) . . ?
C21 C22 C8 112.66(16) . . ?
C24 C23 C22 110.04(15) . . ?
O3 C24 O5 103.52(14) . . ?
O3 C24 C23 108.64(15) . . ?
O5 C24 C23 111.53(15) . . ?
O4 C25 O3 123.5(2) . . ?
O4 C25 C26 126.6(2) . . ?
O3 C25 C26 109.83(19) . . ?

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
C9 O1 C1 C2 160.31(16) . . . . ?
C9 O1 C1 C6 -19.7(2) . . . . ?
O1 C1 C2 C3 178.80(16) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
O1 C1 C6 C5 -179.56(17) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
O1 C1 C6 C7 1.4(3) . . . . ?
C2 C1 C6 C7 -178.65(18) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C4 C5 C6 C7 179.92(18) . . . . ?
C1 C6 C7 O2 167.68(18) . . . . ?
C5 C6 C7 O2 -11.3(3) . . . . ?
C1 C6 C7 C8 -14.4(2) . . . . ?
C5 C6 C7 C8 166.59(17) . . . . ?
O2 C7 C8 F1 -23.3(2) . . . . ?
C6 C7 C8 F1 158.74(15) . . . . ?
O2 C7 C8 C22 95.9(2) . . . . ?
C6 C7 C8 C22 -82.06(19) . . . . ?
O2 C7 C8 C9 -139.72(18) . . . . ?
C6 C7 C8 C9 42.3(2) . . . . ?
C24 O5 C9 O1 -65.81(18) . . . . ?
C24 O5 C9 C10 174.95(14) . . . . ?
C24 O5 C9 C8 52.8(2) . . . . ?
C1 O1 C9 O5 168.29(14) . . . . ?
C1 O1 C9 C10 -76.72(19) . . . . ?
C1 O1 C9 C8 47.69(19) . . . . ?
F1 C8 C9 O5 67.49(17) . . . . ?
C7 C8 C9 O5 -175.36(14) . . . . ?
C22 C8 C9 O5 -51.28(19) . . . . ?
F1 C8 C9 O1 -175.32(13) . . . . ?
C7 C8 C9 O1 -58.17(18) . . . . ?
C22 C8 C9 O1 65.91(18) . . . . ?
F1 C8 C9 C10 -50.92(18) . . . . ?
C7 C8 C9 C10 66.23(19) . . . . ?
C22 C8 C9 C10 -169.68(15) . . . . ?
O5 C9 C10 C11 120.1(2) . . . . ?
O1 C9 C10 C11 4.7(3) . . . . ?
C8 C9 C10 C11 -117.9(2) . . . . ?
C9 C10 C11 C12 -179.58(17) . . . . ?
C10 C11 C12 C17 18.4(3) . . . . ?
C10 C11 C12 C13 -162.4(2) . . . . ?
C17 C12 C13 C14 -1.3(3) . . . . ?
C11 C12 C13 C14 179.5(2) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C17 -0.6(4) . . . . ?
C15 C16 C17 C12 0.3(3) . . . . ?
C13 C12 C17 C16 0.7(3) . . . . ?
C11 C12 C17 C16 179.88(19) . . . . ?
F1 C8 C22 C23 -64.80(18) . . . . ?
C7 C8 C22 C23 176.30(15) . . . . ?
C9 C8 C22 C23 52.99(19) . . . . ?
F1 C8 C22 C21 58.5(2) . . . . ?
C7 C8 C22 C21 -60.4(2) . . . . ?
C9 C8 C22 C21 176.28(16) . . . . ?
C21 C22 C23 C24 179.67(16) . . . . ?
C8 C22 C23 C24 -56.1(2) . . . . ?
C25 O3 C24 O5 -96.47(17) . . . . ?
C25 O3 C24 C23 144.88(16) . . . . ?
C9 O5 C24 O3 -173.45(14) . . . . ?
C9 O5 C24 C23 -56.8(2) . . . . ?
C22 C23 C24 O3 170.87(15) . . . . ?
C22 C23 C24 O5 57.4(2) . . . . ?
C24 O3 C25 O4 -0.2(3) . . . . ?
C24 O3 C25 C26 179.22(17) . . . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.046

