# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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 
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data_C6pF
_database_code_depnum_ccdc_archive 'CCDC 2151796'
loop_
_audit_author_name
_audit_author_address
'Ping Lin'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2022-03-14 deposited with the CCDC.	2022-11-04 downloaded from the CCDC.
;
_audit_creation_date             2022-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H2 Cl2, C21 H15 F O4'
_chemical_formula_sum            'C22 H17 Cl2 F O4'
_chemical_formula_weight         435.25
_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'
Cl Cl 0.1484 0.1585 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.218(2)
_cell_length_b                   10.9800(15)
_cell_length_c                   11.7185(16)
_cell_angle_alpha                90
_cell_angle_beta                 107.344(7)
_cell_angle_gamma                90
_cell_volume                     1991.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3532
_cell_measurement_temperature    260(2)
_cell_measurement_theta_max      21.53
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5971
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1332 before and 0.0959 after correction.
The Ratio of minimum to maximum transmission is 0.8013.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1615
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            36123
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.050
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_min         2.274
_diffrn_ambient_temperature      259.98
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1708
_reflns_number_total             3511
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3511
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1472
_refine_ls_R_factor_gt           0.0602
_refine_ls_restrained_S_all      1.052
_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)+(0.0764P)²+1.4905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1999
_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.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
Cl1 Cl 0.02182(12) 0.66391(15) 0.43338(13) 0.0988(6) Uani 1 1 d . . . . .
Cl2 Cl 0.10990(11) 0.79528(15) 0.64810(14) 0.0958(6) Uani 1 1 d . . . . .
O1 O 0.1559(2) 0.4605(3) 0.7953(3) 0.0649(9) Uani 1 1 d . . . . .
O2 O 0.30349(19) 0.2928(2) 0.5991(3) 0.0534(8) Uani 1 1 d . . . . .
F1 F 0.7423(2) 0.2960(3) 0.0008(3) 0.0926(10) Uani 1 1 d . . . . .
O3 O 0.2549(2) 0.4647(3) 0.6498(3) 0.0659(9) Uani 1 1 d . . . . .
O4 O 0.5009(2) -0.0070(3) 0.2215(3) 0.0736(10) Uani 1 1 d . . . . .
C1 C 0.1039(4) 0.5160(5) 0.8614(5) 0.0781(16) Uani 1 1 d . . . . .
H1A H 0.045658 0.486755 0.831560 0.117 Uiso 1 1 calc GR . . . .
H1B H 0.104517 0.602871 0.852164 0.117 Uiso 1 1 calc GR . . . .
H1C H 0.126934 0.495505 0.944474 0.117 Uiso 1 1 calc GR . . . .
C2 C 0.1629(3) 0.3371(4) 0.7976(4) 0.0511(11) Uani 1 1 d . . . . .
C3 C 0.2126(3) 0.2828(4) 0.7303(4) 0.0469(10) Uani 1 1 d . . . . .
C4 C 0.2555(3) 0.3549(4) 0.6609(4) 0.0501(11) Uani 1 1 d . . . . .
C5 C 0.3106(3) 0.1680(4) 0.6008(4) 0.0496(11) Uani 1 1 d . . . . .
C6 C 0.3609(3) 0.1203(4) 0.5289(4) 0.0550(12) Uani 1 1 d . . . . .
H6 H 0.366851 0.036061 0.528706 0.066 Uiso 1 1 calc R . . . .
C7 C 0.4003(3) 0.1831(4) 0.4617(4) 0.0526(11) Uani 1 1 d . . . . .
H7 H 0.399162 0.267725 0.463576 0.063 Uiso 1 1 calc R . . . .
C8 C 0.4442(3) 0.1237(4) 0.3871(4) 0.0536(11) Uani 1 1 d . . . . .
H8 H 0.445595 0.039010 0.389740 0.064 Uiso 1 1 calc R . . . .
C9 C 0.4829(3) 0.1761(4) 0.3149(4) 0.0533(11) Uani 1 1 d . . . . .
H9 H 0.487070 0.260492 0.313621 0.064 Uiso 1 1 calc R . . . .
C10 C 0.5197(3) 0.1020(4) 0.2363(4) 0.0545(12) Uani 1 1 d . . . . .
C11 C 0.5784(3) 0.1564(4) 0.1755(4) 0.0484(11) Uani 1 1 d . . . . .
C12 C 0.6149(3) 0.2718(4) 0.2029(4) 0.0563(12) Uani 1 1 d . . . . .
H12 H 0.600848 0.318708 0.260565 0.068 Uiso 1 1 calc R . . . .
C13 C 0.6713(3) 0.3175(4) 0.1465(4) 0.0603(13) Uani 1 1 d . . . . .
H13 H 0.696485 0.393732 0.166411 0.072 Uiso 1 1 calc R . . . .
C14 C 0.6892(3) 0.2485(5) 0.0606(4) 0.0610(13) Uani 1 1 d . . . . .
C15 C 0.2205(3) 0.1551(4) 0.7317(4) 0.0509(11) Uani 1 1 d . . . . .
C16 C 0.1800(3) 0.0841(4) 0.7990(4) 0.0610(13) Uani 1 1 d . . . . .
H16 H 0.185659 -0.000218 0.800062 0.073 Uiso 1 1 calc R . . . .
C17 C 0.1323(3) 0.1391(4) 0.8630(4) 0.0637(13) Uani 1 1 d . . . . .
H17 H 0.105417 0.091490 0.907184 0.076 Uiso 1 1 calc R . . . .
C18 C 0.1233(3) 0.2649(4) 0.8630(4) 0.0605(12) Uani 1 1 d . . . . .
H18 H 0.090600 0.300789 0.907001 0.073 Uiso 1 1 calc R . . . .
C19 C 0.2712(3) 0.1001(4) 0.6645(4) 0.0531(11) Uani 1 1 d . . . . .
H19 H 0.277037 0.015803 0.664909 0.064 Uiso 1 1 calc R . . . .
C20 C 0.6013(3) 0.0896(4) 0.0891(4) 0.0564(12) Uani 1 1 d . . . . .
H20 H 0.578615 0.011767 0.070823 0.068 Uiso 1 1 calc R . . . .
C21 C 0.6562(3) 0.1339(4) 0.0297(4) 0.0617(13) Uani 1 1 d . . . . .
H21 H 0.670403 0.088484 -0.028771 0.074 Uiso 1 1 calc R . . . .
C22 C 0.1031(4) 0.6601(5) 0.5684(5) 0.0861(17) Uani 1 1 d . . . . .
H22A H 0.157891 0.645005 0.553518 0.103 Uiso 1 1 calc R . . . .
H22B H 0.092361 0.593369 0.616333 0.103 Uiso 1 1 calc R . . . .


_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
Cl1 C22 1.732(6) . ?
Cl2 C22 1.739(5) . ?
O1 C1 1.440(5) . ?
O1 C2 1.359(5) . ?
O2 C4 1.389(5) . ?
O2 C5 1.376(5) . ?
F1 C14 1.366(5) . ?
O3 C4 1.212(5) . ?
O4 C10 1.235(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.415(6) . ?
C2 C18 1.387(6) . ?
C3 C4 1.453(6) . ?
C3 C15 1.408(6) . ?
C5 C6 1.435(6) . ?
C5 C19 1.343(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.342(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.439(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.326(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.481(6) . ?
C10 C11 1.474(6) . ?
C11 C12 1.396(6) . ?
C11 C20 1.387(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.358(6) . ?
C14 C21 1.372(7) . ?
C15 C16 1.403(6) . ?
C15 C19 1.432(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.369(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.373(6) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 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
C2 O1 C1 118.1(4) . . ?
C5 O2 C4 122.6(3) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 117.8(4) . . ?
O1 C2 C18 122.1(4) . . ?
C18 C2 C3 120.1(4) . . ?
C2 C3 C4 122.0(4) . . ?
C15 C3 C2 118.6(4) . . ?
C15 C3 C4 119.4(4) . . ?
O2 C4 C3 117.5(4) . . ?
O3 C4 O2 114.8(4) . . ?
O3 C4 C3 127.7(4) . . ?
O2 C5 C6 114.5(4) . . ?
C19 C5 O2 120.6(4) . . ?
C19 C5 C6 124.8(4) . . ?
C5 C6 H6 116.2 . . ?
C7 C6 C5 127.6(4) . . ?
C7 C6 H6 116.2 . . ?
C6 C7 H7 118.9 . . ?
C6 C7 C8 122.1(4) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 H8 116.4 . . ?
C9 C8 C7 127.3(4) . . ?
C9 C8 H8 116.4 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.9(4) . . ?
C10 C9 H9 119.5 . . ?
O4 C10 C9 119.4(4) . . ?
O4 C10 C11 119.6(4) . . ?
C11 C10 C9 121.1(4) . . ?
C12 C11 C10 123.2(4) . . ?
C20 C11 C10 119.4(4) . . ?
C20 C11 C12 117.4(4) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.9 . . ?
C14 C13 C12 118.2(4) . . ?
C14 C13 H13 120.9 . . ?
F1 C14 C21 118.0(4) . . ?
C13 C14 F1 118.3(4) . . ?
C13 C14 C21 123.7(4) . . ?
C3 C15 C19 118.7(4) . . ?
C16 C15 C3 120.2(4) . . ?
C16 C15 C19 121.1(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(4) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C2 C18 C17 120.2(4) . . ?
C2 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C5 C19 C15 121.2(4) . . ?
C5 C19 H19 119.4 . . ?
C15 C19 H19 119.4 . . ?
C11 C20 H20 118.7 . . ?
C21 C20 C11 122.6(4) . . ?
C21 C20 H20 118.7 . . ?
C14 C21 C20 116.8(4) . . ?
C14 C21 H21 121.6 . . ?
C20 C21 H21 121.6 . . ?
Cl1 C22 Cl2 112.3(3) . . ?
Cl1 C22 H22A 109.1 . . ?
Cl1 C22 H22B 109.1 . . ?
Cl2 C22 H22A 109.1 . . ?
Cl2 C22 H22B 109.1 . . ?
H22A C22 H22B 107.9 . . ?

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 C2 C3 C4 0.3(6) . . . . ?
O1 C2 C3 C15 -180.0(4) . . . . ?
O1 C2 C18 C17 -179.9(4) . . . . ?
O2 C5 C6 C7 -0.2(7) . . . . ?
O2 C5 C19 C15 0.3(7) . . . . ?
F1 C14 C21 C20 -178.4(4) . . . . ?
O4 C10 C11 C12 -168.4(4) . . . . ?
O4 C10 C11 C20 9.5(7) . . . . ?
C1 O1 C2 C3 178.6(4) . . . . ?
C1 O1 C2 C18 -1.3(6) . . . . ?
C2 C3 C4 O2 179.3(4) . . . . ?
C2 C3 C4 O3 -0.7(7) . . . . ?
C2 C3 C15 C16 -0.3(6) . . . . ?
C2 C3 C15 C19 -179.5(4) . . . . ?
C3 C2 C18 C17 0.1(7) . . . . ?
C3 C15 C16 C17 0.4(7) . . . . ?
C3 C15 C19 C5 -0.2(6) . . . . ?
C4 O2 C5 C6 178.3(4) . . . . ?
C4 O2 C5 C19 -0.6(6) . . . . ?
C4 C3 C15 C16 179.5(4) . . . . ?
C4 C3 C15 C19 0.3(6) . . . . ?
C5 O2 C4 O3 -179.4(4) . . . . ?
C5 O2 C4 C3 0.6(6) . . . . ?
C5 C6 C7 C8 -175.8(4) . . . . ?
C6 C5 C19 C15 -178.5(4) . . . . ?
C6 C7 C8 C9 177.9(5) . . . . ?
C7 C8 C9 C10 -175.2(4) . . . . ?
C8 C9 C10 O4 13.1(7) . . . . ?
C8 C9 C10 C11 -166.9(4) . . . . ?
C9 C10 C11 C12 11.6(7) . . . . ?
C9 C10 C11 C20 -170.5(4) . . . . ?
C10 C11 C12 C13 178.1(4) . . . . ?
C10 C11 C20 C21 -179.4(4) . . . . ?
C11 C12 C13 C14 1.5(7) . . . . ?
C11 C20 C21 C14 0.9(7) . . . . ?
C12 C11 C20 C21 -1.4(7) . . . . ?
C12 C13 C14 F1 177.2(4) . . . . ?
C12 C13 C14 C21 -2.1(8) . . . . ?
C13 C14 C21 C20 0.9(7) . . . . ?
C15 C3 C4 O2 -0.5(6) . . . . ?
C15 C3 C4 O3 179.6(4) . . . . ?
C15 C16 C17 C18 -0.3(7) . . . . ?
C16 C15 C19 C5 -179.4(4) . . . . ?
C16 C17 C18 C2 0.0(7) . . . . ?
C18 C2 C3 C4 -179.8(4) . . . . ?
C18 C2 C3 C15 0.0(6) . . . . ?
C19 C5 C6 C7 178.7(5) . . . . ?
C19 C15 C16 C17 179.6(4) . . . . ?
C20 C11 C12 C13 0.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
