# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_5f-ant
_database_code_depnum_ccdc_archive 'CCDC 2033782'
loop_
_audit_author_name
_audit_author_address
'Si Liu'
;Tianjin University
China
;
_audit_update_record             
;
2020-09-24 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;
_audit_creation_date             2019-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H9 F5'
_chemical_formula_sum            'C20 H9 F5'
_chemical_formula_weight         344.27
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H9 F5'
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'

_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.26360(10)
_cell_length_b                   15.4509(2)
_cell_length_c                   7.56040(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1432.57(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7088
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0400
_cell_measurement_theta_min      3.5980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.3
_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  0.0196
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9117
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.068
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         4.603
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00 -58.00   1.00    2.50    --  -41.12 125.00 -30.00   27
  2  ω    -63.00  30.00   1.00    2.50    --  -41.12  37.00  60.00   93
  3  ω    -69.00  27.00   1.00    2.50    --  -41.12  57.00 -90.00   96
  4  ω   -112.00 -22.00   1.00    2.50    --  -41.12 -57.00 120.00   90
  5  ω     29.00  54.00   1.00    2.50    --   41.12-125.00-180.00   25
  6  ω     95.00 175.00   1.00   13.00    --  105.32  30.00-150.00   80
  7  ω     32.00 116.00   1.00   13.00    --  105.32-125.00  60.00   84
  8  ω     23.00  85.00   1.00   13.00    --  105.32 -94.00-120.00   62
  9  ω     57.00 117.00   1.00   13.00    --  105.32-125.00-120.00   60
 10  ω     24.00  99.00   1.00   13.00    --  105.32 -94.00 -60.00   75
 11  ω    107.00 134.00   1.00   13.00    --  105.32 -77.00  30.00   27
 12  ω     32.00 113.00   1.00   13.00    --  105.32 -45.00  60.00   81
 13  ω     79.00 154.00   1.00   13.00    --  105.32  45.00 -90.00   75
 14  ω     39.00  69.00   1.00   13.00    --  105.32 -77.00  30.00   30
 15  ω     38.00  95.00   1.00   13.00    --  105.32 -45.00 -90.00   57
 16  ω     23.00  94.00   1.00   13.00    --  105.32 -94.00  90.00   71
 17  ω     98.00 178.00   1.00   13.00    --  105.32  15.00 -30.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0498601000
_diffrn_orient_matrix_UB_12      0.1200354000
_diffrn_orient_matrix_UB_13      0.0701762000
_diffrn_orient_matrix_UB_21      0.0286038000
_diffrn_orient_matrix_UB_22      0.1642336000
_diffrn_orient_matrix_UB_23      -0.0544810000
_diffrn_orient_matrix_UB_31      -0.1117053000
_diffrn_orient_matrix_UB_32      -0.0115592000
_diffrn_orient_matrix_UB_33      -0.0452665000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                2424
_reflns_number_total             2484
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1048 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2484
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0266
_refine_ls_restrained_S_all      1.064
_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)+(0.0482P)²+0.0506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0685
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H00A(0.046) H00F(0.051) H00G(0.052) H00H(0.048) H00K(0.052)
 H00M(0.063) H00N(0.065) H00O(0.073) H00P(0.073)
 Fixed X: H00A(0.589278) H00F(0.308512) H00G(0.236323) H00H(0.602763)
 H00K(0.253214) H00M(0.61408) H00N(0.26728) H00O(0.363292) H00P(0.53693)
 Fixed Y: H00A(0.453799) H00F(0.555565) H00G(0.421232) H00H(0.2957)
 H00K(0.261167) H00M(0.13664) H00N(0.101619) H00O(-0.014557) H00P(0.002901)
 Fixed Z: H00A(0.434507) H00F(0.615934) H00G(0.650507) H00H(0.391011)
 H00K(0.61974) H00M(0.336301) H00N(0.5776) H00O(0.476643) H00P(0.356417)
;
_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
F001 F 0.67120(9) 0.56736(7) 0.64333(17) 0.0509(3) Uani 1 1 d . . . . .
F002 F 0.34844(9) 0.65971(7) 0.35898(19) 0.0537(3) Uani 1 1 d . . . . .
F003 F 0.74669(9) 0.72905(8) 0.6326(2) 0.0589(3) Uani 1 1 d . . . . .
F004 F 0.42411(11) 0.82183(8) 0.3559(2) 0.0611(3) Uani 1 1 d . . . . .
F005 F 0.62375(11) 0.85795(8) 0.4926(2) 0.0648(4) Uani 1 1 d . . . . .
C006 C 0.60808(15) 0.62798(13) 0.5686(2) 0.0402(4) Uani 1 1 d . . . . .
C007 C 0.50490(14) 0.60662(11) 0.5052(3) 0.0385(4) Uani 1 1 d . . . . .
C008 C 0.45859(14) 0.51811(12) 0.5198(3) 0.0381(4) Uani 1 1 d . . . . .
C009 C 0.36592(14) 0.35108(13) 0.5578(3) 0.0397(4) Uani 1 1 d . . . . .
C00A C 0.51826(14) 0.44673(12) 0.4751(2) 0.0384(4) Uani 1 1 d . . . . .
H00A H 0.589278 0.453799 0.434507 0.046 Uiso 1 1 calc R . . . .
C00B C 0.64796(15) 0.71132(13) 0.5651(3) 0.0432(4) Uani 1 1 d . . . . .
C00C C 0.47421(14) 0.36173(12) 0.4894(2) 0.0373(4) Uani 1 1 d . . . . .
C00D C 0.44615(15) 0.67472(12) 0.4313(3) 0.0413(4) Uani 1 1 d . . . . .
C00E C 0.58602(16) 0.77707(12) 0.4947(3) 0.0462(4) Uani 1 1 d . . . . .
C00F C 0.34972(14) 0.50721(13) 0.5860(3) 0.0425(4) Uani 1 1 d . . . . .
H00F H 0.308512 0.555565 0.615934 0.051 Uiso 1 1 calc R . . . .
C00G C 0.30647(14) 0.42693(13) 0.6052(3) 0.0434(4) Uani 1 1 d . . . . .
H00G H 0.236323 0.421232 0.650507 0.052 Uiso 1 1 calc R . . . .
C00H C 0.53246(15) 0.28883(12) 0.4349(3) 0.0402(4) Uani 1 1 d . . . . .
H00H H 0.602763 0.295700 0.391011 0.048 Uiso 1 1 calc R . . . .
C00I C 0.48453(17) 0.75855(12) 0.4266(3) 0.0451(4) Uani 1 1 d . . . . .
C00J C 0.48779(16) 0.20582(12) 0.4448(3) 0.0423(4) Uani 1 1 d . . . . .
C00K C 0.32260(15) 0.26815(13) 0.5722(3) 0.0435(4) Uani 1 1 d . . . . .
H00K H 0.253214 0.261167 0.619740 0.052 Uiso 1 1 calc R . . . .
C00L C 0.38055(16) 0.19507(13) 0.5171(3) 0.0430(4) Uani 1 1 d . . . . .
C00M C 0.54469(18) 0.13081(13) 0.3845(3) 0.0527(5) Uani 1 1 d . . . . .
H00M H 0.614080 0.136640 0.336301 0.063 Uiso 1 1 calc R . . . .
C00N C 0.33613(18) 0.10977(14) 0.5288(3) 0.0538(5) Uani 1 1 d . . . . .
H00N H 0.267280 0.101619 0.577600 0.065 Uiso 1 1 calc R . . . .
C00O C 0.3936(2) 0.04050(14) 0.4693(4) 0.0604(6) Uani 1 1 d . . . . .
H00O H 0.363292 -0.014557 0.476643 0.073 Uiso 1 1 calc R . . . .
C00P C 0.4987(2) 0.05105(13) 0.3965(4) 0.0606(6) Uani 1 1 d . . . . .
H00P H 0.536930 0.002901 0.356417 0.073 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
F001 C006 1.340(2) . ?
F002 C00D 1.337(2) . ?
F003 C00B 1.342(2) . ?
F004 C00I 1.338(2) . ?
F005 C00E 1.333(2) . ?
C006 C007 1.393(3) . ?
C006 C00B 1.378(3) . ?
C007 C008 1.485(3) . ?
C007 C00D 1.392(3) . ?
C008 C00A 1.366(3) . ?
C008 C00F 1.436(2) . ?
C009 C00C 1.435(3) . ?
C009 C00G 1.426(3) . ?
C009 C00K 1.391(3) . ?
C00A C00C 1.424(3) . ?
C00B C00E 1.376(3) . ?
C00C C00H 1.396(3) . ?
C00D C00I 1.379(3) . ?
C00E C00I 1.377(3) . ?
C00F C00G 1.357(3) . ?
C00H C00J 1.397(3) . ?
C00J C00L 1.434(3) . ?
C00J C00M 1.428(3) . ?
C00K C00L 1.398(3) . ?
C00L C00N 1.429(3) . ?
C00M C00P 1.358(3) . ?
C00N C00O 1.358(3) . ?
C00O C00P 1.411(4) . ?

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
F001 C006 C007 120.28(17) . . ?
F001 C006 C00B 117.15(16) . . ?
C00B C006 C007 122.51(18) . . ?
C006 C007 C008 122.70(17) . . ?
C00D C007 C006 115.41(16) . . ?
C00D C007 C008 121.86(16) . . ?
C00A C008 C007 121.36(16) . . ?
C00A C008 C00F 119.31(17) . . ?
C00F C008 C007 119.31(16) . . ?
C00G C009 C00C 118.01(17) . . ?
C00K C009 C00C 119.17(17) . . ?
C00K C009 C00G 122.81(17) . . ?
C008 C00A C00C 121.51(16) . . ?
F003 C00B C006 120.24(18) . . ?
F003 C00B C00E 119.64(18) . . ?
C00E C00B C006 120.11(17) . . ?
C00A C00C C009 118.96(16) . . ?
C00H C00C C009 119.17(17) . . ?
C00H C00C C00A 121.85(16) . . ?
F002 C00D C007 119.78(16) . . ?
F002 C00D C00I 117.29(16) . . ?
C00I C00D C007 122.93(17) . . ?
F005 C00E C00B 120.35(18) . . ?
F005 C00E C00I 120.29(18) . . ?
C00B C00E C00I 119.36(17) . . ?
C00G C00F C008 120.54(17) . . ?
C00F C00G C009 121.63(17) . . ?
C00C C00H C00J 121.64(17) . . ?
F004 C00I C00D 120.50(18) . . ?
F004 C00I C00E 119.88(18) . . ?
C00E C00I C00D 119.63(18) . . ?
C00H C00J C00L 119.11(17) . . ?
C00H C00J C00M 122.46(18) . . ?
C00M C00J C00L 118.43(18) . . ?
C009 C00K C00L 121.77(17) . . ?
C00K C00L C00J 119.10(17) . . ?
C00K C00L C00N 122.20(19) . . ?
C00N C00L C00J 118.69(19) . . ?
C00P C00M C00J 120.8(2) . . ?
C00O C00N C00L 120.6(2) . . ?
C00N C00O C00P 120.81(19) . . ?
C00M C00P C00O 120.7(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.365
_oxdiff_exptl_absorpt_empirical_full_min 0.832
