# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_zxm_lz_5f_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2hpmhb
_database_code_depnum_ccdc_archive 'CCDC 2314692'
loop_
_audit_author_name
_audit_author_address
'Zheng Luo'
;Sichuan university
China
;
_audit_update_record             
;
2023-12-15 deposited with the CCDC.	2024-06-09 downloaded from the CCDC.
;
_audit_creation_date             2023-08-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 F5 O'
_chemical_formula_sum            'C12 H9 F5 O'
_chemical_formula_weight         264.19
_chemical_absolute_configuration .
_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      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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   4.915(3)
_cell_length_b                   11.218(7)
_cell_length_c                   20.402(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1124.8(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2190
_cell_measurement_temperature    285(2)
_cell_measurement_theta_max      22.627
_cell_measurement_theta_min      2.699
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1635 before and 0.0754 after correction.
The Ratio of minimum to maximum transmission is 0.6154.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            9067
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.806
_diffrn_reflns_theta_min         2.072
_diffrn_ambient_temperature      285.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_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         0.673
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                1498
_reflns_number_total             2622
_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 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 415 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2622
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.026
_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)+(0.0583P)²+0.1395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1573
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.0796(8) 0.3167(3) 0.86465(16) 0.0998(11) Uani 1 1 d . . . . .
F2 F 0.8550(5) 0.1713(2) 0.65743(14) 0.0691(8) Uani 1 1 d . . . . .
F3 F 1.1621(6) 0.1610(3) 0.76580(18) 0.0886(10) Uani 1 1 d . . . . .
F4 F 0.3658(6) 0.4926(2) 0.74794(15) 0.0750(8) Uani 1 1 d . . . . .
F5 F 0.6778(8) 0.4837(3) 0.85475(16) 0.0936(11) Uani 1 1 d . . . . .
O1 O 0.2044(7) 0.2923(3) 0.5140(2) 0.0821(12) Uani 1 1 d . . . . .
H1 H 0.3563 0.2841 0.4980 0.123 Uiso 1 1 calc R U . . .
C1 C 0.9255(11) 0.3221(5) 0.8108(3) 0.0690(13) Uani 1 1 d . . . . .
C2 C 0.7235(11) 0.4072(4) 0.8055(3) 0.0643(13) Uani 1 1 d . . . . .
C3 C 0.5693(9) 0.4111(4) 0.7495(2) 0.0572(11) Uani 1 1 d . . . . .
C4 C 0.6042(9) 0.3351(3) 0.6972(2) 0.0512(10) Uani 1 1 d . . . . .
C5 C 0.4328(9) 0.3321(4) 0.6385(2) 0.0552(11) Uani 1 1 d . . . . .
H5 H 0.3741 0.2572 0.6251 0.066 Uiso 1 1 calc R U . . .
C6 C 0.3508(9) 0.4231(4) 0.6020(2) 0.0537(11) Uani 1 1 d . . . . .
C7 C 0.4294(13) 0.5522(4) 0.6070(3) 0.0744(15) Uani 1 1 d . . . . .
H7A H 0.6227 0.5602 0.6155 0.089 Uiso 1 1 calc R U . . .
H7B H 0.3295 0.5911 0.6420 0.089 Uiso 1 1 calc R U . . .
C8 C 0.3568(19) 0.6055(5) 0.5415(3) 0.118(3) Uani 1 1 d . . . . .
H8A H 0.2049 0.6600 0.5462 0.142 Uiso 1 1 calc R U . . .
H8B H 0.5106 0.6491 0.5239 0.142 Uiso 1 1 calc R U . . .
C9 C 0.8101(9) 0.2504(4) 0.7056(2) 0.0542(11) Uani 1 1 d . . . . .
C10 C 0.9665(10) 0.2437(4) 0.7602(3) 0.0618(12) Uani 1 1 d . . . . .
C11 C 0.1822(10) 0.4074(4) 0.5418(3) 0.0674(13) Uani 1 1 d . . . . .
H11 H -0.0088 0.4225 0.5528 0.081 Uiso 1 1 calc R U . . .
C12 C 0.282(2) 0.5056(6) 0.4971(3) 0.110(2) Uani 1 1 d . . . . .
H12A H 0.4389 0.4792 0.4721 0.132 Uiso 1 1 calc R U . . .
H12B H 0.1402 0.5298 0.4668 0.132 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 C1 1.336(6) . ?
F2 C9 1.342(5) . ?
F3 C10 1.341(5) . ?
F4 C3 1.355(5) . ?
F5 C2 1.340(5) . ?
O1 H1 0.8200 . ?
O1 C11 1.414(5) . ?
C1 C2 1.382(7) . ?
C1 C10 1.371(7) . ?
C2 C3 1.372(7) . ?
C3 C4 1.377(6) . ?
C4 C5 1.465(6) . ?
C4 C9 1.399(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.325(6) . ?
C6 C7 1.502(6) . ?
C6 C11 1.492(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.507(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C12 1.488(8) . ?
C9 C10 1.355(7) . ?
C11 H11 0.9800 . ?
C11 C12 1.512(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
C11 O1 H1 109.5 . . ?
F1 C1 C2 120.2(5) . . ?
F1 C1 C10 120.5(5) . . ?
C10 C1 C2 119.3(5) . . ?
F5 C2 C1 120.3(5) . . ?
F5 C2 C3 120.8(5) . . ?
C3 C2 C1 119.0(5) . . ?
F4 C3 C2 116.7(4) . . ?
F4 C3 C4 119.5(4) . . ?
C2 C3 C4 123.8(4) . . ?
C3 C4 C5 125.2(4) . . ?
C3 C4 C9 114.5(4) . . ?
C9 C4 C5 120.1(4) . . ?
C4 C5 H5 116.0 . . ?
C6 C5 C4 128.0(4) . . ?
C6 C5 H5 116.0 . . ?
C5 C6 C7 128.7(4) . . ?
C5 C6 C11 122.7(4) . . ?
C11 C6 C7 108.2(4) . . ?
C6 C7 H7A 110.7 . . ?
C6 C7 H7B 110.7 . . ?
C6 C7 C8 105.1(5) . . ?
H7A C7 H7B 108.8 . . ?
C8 C7 H7A 110.7 . . ?
C8 C7 H7B 110.7 . . ?
C7 C8 H8A 110.2 . . ?
C7 C8 H8B 110.2 . . ?
H8A C8 H8B 108.5 . . ?
C12 C8 C7 107.5(5) . . ?
C12 C8 H8A 110.2 . . ?
C12 C8 H8B 110.2 . . ?
F2 C9 C4 118.5(4) . . ?
F2 C9 C10 118.2(4) . . ?
C10 C9 C4 123.3(4) . . ?
F3 C10 C1 119.0(5) . . ?
F3 C10 C9 121.0(5) . . ?
C9 C10 C1 120.0(5) . . ?
O1 C11 C6 113.2(4) . . ?
O1 C11 H11 108.9 . . ?
O1 C11 C12 113.4(5) . . ?
C6 C11 H11 108.9 . . ?
C6 C11 C12 103.4(4) . . ?
C12 C11 H11 108.9 . . ?
C8 C12 C11 105.1(5) . . ?
C8 C12 H12A 110.7 . . ?
C8 C12 H12B 110.7 . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F5 -1.1(7) . . . . ?
F1 C1 C2 C3 179.6(5) . . . . ?
F1 C1 C10 F3 0.5(7) . . . . ?
F1 C1 C10 C9 -179.6(4) . . . . ?
F2 C9 C10 F3 0.4(6) . . . . ?
F2 C9 C10 C1 -179.4(4) . . . . ?
F4 C3 C4 C5 -1.4(6) . . . . ?
F4 C3 C4 C9 -176.5(4) . . . . ?
F5 C2 C3 F4 -2.2(6) . . . . ?
F5 C2 C3 C4 -179.7(4) . . . . ?
O1 C11 C12 C8 -156.0(6) . . . . ?
C1 C2 C3 F4 177.1(4) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C2 C1 C10 F3 -179.7(4) . . . . ?
C2 C1 C10 C9 0.2(7) . . . . ?
C2 C3 C4 C5 176.0(4) . . . . ?
C2 C3 C4 C9 0.9(6) . . . . ?
C3 C4 C5 C6 47.5(7) . . . . ?
C3 C4 C9 F2 178.9(4) . . . . ?
C3 C4 C9 C10 -0.9(6) . . . . ?
C4 C5 C6 C7 5.9(8) . . . . ?
C4 C5 C6 C11 178.0(4) . . . . ?
C4 C9 C10 F3 -179.8(4) . . . . ?
C4 C9 C10 C1 0.4(7) . . . . ?
C5 C4 C9 F2 3.5(6) . . . . ?
C5 C4 C9 C10 -176.3(4) . . . . ?
C5 C6 C7 C8 160.9(6) . . . . ?
C5 C6 C11 O1 -22.5(7) . . . . ?
C5 C6 C11 C12 -145.6(5) . . . . ?
C6 C7 C8 C12 -9.0(9) . . . . ?
C6 C11 C12 C8 -33.0(8) . . . . ?
C7 C6 C11 O1 151.1(4) . . . . ?
C7 C6 C11 C12 28.0(6) . . . . ?
C7 C8 C12 C11 26.3(9) . . . . ?
C9 C4 C5 C6 -137.6(5) . . . . ?
C10 C1 C2 F5 179.1(5) . . . . ?
C10 C1 C2 C3 -0.2(7) . . . . ?
C11 C6 C7 C8 -12.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
