# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_cxl
_database_code_depnum_ccdc_archive 'CCDC 1998826'
loop_
_audit_author_name
_audit_author_address
Chenxiaolong
;Peking univercity
China
;
_audit_update_record             
;
2020-04-23 deposited with the CCDC.	2020-04-24 downloaded from the CCDC.
;
_audit_creation_date             2019-08-23
_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         'C28 H14 F6 N2 O6 S'
_chemical_formula_sum            'C28 H14 F6 N2 O6 S'
_chemical_formula_weight         620.47
_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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.4105(2)
_cell_length_b                   7.0350(4)
_cell_length_c                   19.7087(13)
_cell_angle_alpha                87.105(5)
_cell_angle_beta                 88.775(4)
_cell_angle_gamma                80.022(4)
_cell_volume                     601.45(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2221
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.4550
_cell_measurement_theta_min      2.9410
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             314
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4220
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.069
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  85.00   1.00    3.50    --   11.74  57.00   0.00   96
  2  ω     37.00  63.00   1.00    3.50    --   11.74 178.00-180.00   26
  3  ω    -12.00  78.00   1.00    3.50    --   11.74  77.00 120.00   90
  4  ω    -54.00  39.00   1.00    3.50    --   11.74 -57.00-150.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0343722000
_diffrn_orient_matrix_UB_12      0.0844478000
_diffrn_orient_matrix_UB_13      -0.0215970000
_diffrn_orient_matrix_UB_21      0.0378991000
_diffrn_orient_matrix_UB_22      0.0564377000
_diffrn_orient_matrix_UB_23      0.0263637000
_diffrn_orient_matrix_UB_31      0.1550821000
_diffrn_orient_matrix_UB_32      -0.0136874000
_diffrn_orient_matrix_UB_33      -0.0117164000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1857
_reflns_number_total             2121
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         0.252
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.079
_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)+(0.0329P)²+0.5309P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1003
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: S1(0.5) C15(0.5) C14(0.5) H1B(0.5) H1A(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C9(H9), C8(H8), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
F2 F 0.1848(3) 0.88459(19) 0.59220(7) 0.0296(4) Uani 1 1 d . . . . .
F1 F 0.2452(3) 0.6708(2) 0.51735(7) 0.0333(4) Uani 1 1 d . . . . .
F3 F -0.1991(3) 0.8442(2) 0.53274(7) 0.0359(4) Uani 1 1 d . . . . .
O3 O -0.0362(3) 0.6246(2) 0.60992(8) 0.0231(4) Uani 1 1 d . . . . .
O1 O 0.5780(4) -0.1082(2) 0.79581(9) 0.0346(5) Uani 1 1 d . . . . .
N14 N 0.7726(4) 0.1312(3) 0.84378(9) 0.0183(4) Uani 1 1 d . . . . .
O2 O 0.9687(5) 0.3758(3) 0.89043(11) 0.0493(6) Uani 1 1 d . . . . .
C10 C 0.2025(5) 0.5153(3) 0.64987(11) 0.0192(5) Uani 1 1 d . . . . .
C7 C 0.6456(5) 0.2976(3) 0.73112(11) 0.0197(5) Uani 1 1 d . . . . .
C5 C 0.6137(5) -0.0266(3) 0.84676(12) 0.0214(5) Uani 1 1 d . . . . .
C13 C 0.0499(5) 0.7526(3) 0.56405(11) 0.0225(5) Uani 1 1 d . . . . .
C11 C 0.3278(5) 0.3324(3) 0.63176(12) 0.0236(5) Uani 1 1 d . . . . .
H11 H 0.265322 0.282778 0.592532 0.028 Uiso 1 1 calc R . . . .
C9 C 0.2912(5) 0.5927(3) 0.70745(11) 0.0218(5) Uani 1 1 d . . . . .
H9 H 0.201612 0.716486 0.719173 0.026 Uiso 1 1 calc R . . . .
C8 C 0.5156(5) 0.4831(3) 0.74746(12) 0.0221(5) Uani 1 1 d . . . . .
H8 H 0.580364 0.534839 0.786018 0.027 Uiso 1 1 calc R . . . .
C6 C 0.8913(5) 0.1823(3) 0.77572(12) 0.0237(5) Uani 1 1 d . . . . .
H6A H 0.979026 0.064719 0.753686 0.028 Uiso 1 1 calc R . . . .
H6B H 1.054527 0.256675 0.780848 0.028 Uiso 1 1 calc R . . . .
C12 C 0.5495(5) 0.2227(3) 0.67311(12) 0.0244(5) Uani 1 1 d . . . . .
H12 H 0.634589 0.097738 0.661808 0.029 Uiso 1 1 calc R . . . .
C4 C 0.8283(5) 0.2436(4) 0.89824(13) 0.0292(6) Uani 1 1 d . . . . .
C1 C 0.5012(6) -0.0799(4) 0.91402(15) 0.0408(7) Uani 1 1 d . . . . .
C2 C 0.5546(6) 0.0266(5) 0.96790(14) 0.0465(9) Uani 1 1 d . . . . .
C3 C 0.7045(7) 0.1845(5) 0.96414(14) 0.0481(9) Uani 1 1 d . . . . .
S1 S 0.3279(3) -0.23979(18) 0.95368(9) 0.0178(3) Uani 0.5 1 d . . P . .
C15 C 0.2139(11) -0.3098(7) 0.9807(3) 0.0188(10) Uani 0.5 1 d . . P . .
C14 C 0.3281(11) -0.2546(7) 0.9138(4) 0.0209(11) Uani 0.5 1 d . . P . .
H1B H 0.103(10) -0.426(7) 0.987(2) 0.018(12) Uiso 0.5 1 d . . P . .
H1A H 0.295(9) -0.325(6) 0.875(2) 0.007(10) Uiso 0.5 1 d . . P . .


_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
F2 C13 1.335(3) . ?
F1 C13 1.330(3) . ?
F3 C13 1.321(3) . ?
O3 C10 1.419(3) . ?
O3 C13 1.340(3) . ?
O1 C5 1.208(3) . ?
N14 C5 1.410(3) . ?
N14 C6 1.480(3) . ?
N14 C4 1.415(3) . ?
O2 C4 1.205(3) . ?
C10 C11 1.371(3) . ?
C10 C9 1.376(3) . ?
C7 C8 1.383(3) . ?
C7 C6 1.506(3) . ?
C7 C12 1.387(3) . ?
C5 C1 1.460(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.379(3) . ?
C8 H8 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C12 H12 0.9300 . ?
C4 C3 1.467(4) . ?
C1 C2 1.377(5) . ?
C1 S1 1.626(3) . ?
C1 C14 1.555(6) . ?
C2 C2 1.401(6) 2_657 ?
C2 C3 1.386(5) . ?
C3 S1 1.682(3) 2_657 ?
C3 C15 1.520(6) 2_657 ?
S1 C15 0.910(6) . ?
S1 C14 0.797(6) . ?
S1 H1B 1.86(5) . ?
S1 H1A 1.71(4) . ?
C15 C14 1.460(7) . ?
C15 H1B 1.03(5) . ?
C14 H1A 0.96(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
C13 O3 C10 116.04(16) . . ?
C5 N14 C6 115.32(18) . . ?
C5 N14 C4 127.1(2) . . ?
C4 N14 C6 117.6(2) . . ?
C11 C10 O3 119.09(19) . . ?
C11 C10 C9 121.9(2) . . ?
C9 C10 O3 118.9(2) . . ?
C8 C7 C6 119.6(2) . . ?
C8 C7 C12 119.0(2) . . ?
C12 C7 C6 121.4(2) . . ?
O1 C5 N14 120.3(2) . . ?
O1 C5 C1 124.2(2) . . ?
N14 C5 C1 115.5(2) . . ?
F2 C13 O3 112.71(18) . . ?
F1 C13 F2 106.83(18) . . ?
F1 C13 O3 113.06(19) . . ?
F3 C13 F2 107.81(19) . . ?
F3 C13 F1 108.08(18) . . ?
F3 C13 O3 108.15(18) . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.7(2) . . ?
C12 C11 H11 120.6 . . ?
C10 C9 H9 120.7 . . ?
C10 C9 C8 118.7(2) . . ?
C8 C9 H9 120.7 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.0(2) . . ?
C9 C8 H8 119.5 . . ?
N14 C6 C7 112.69(18) . . ?
N14 C6 H6A 109.1 . . ?
N14 C6 H6B 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C7 C12 C11 120.6(2) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
N14 C4 C3 114.5(2) . . ?
O2 C4 N14 122.0(3) . . ?
O2 C4 C3 123.4(3) . . ?
C5 C1 S1 141.7(3) . . ?
C5 C1 C14 113.0(4) . . ?
C2 C1 C5 118.4(3) . . ?
C2 C1 S1 99.8(2) . . ?
C2 C1 C14 128.6(4) . . ?
C14 C1 S1 28.9(2) . . ?
C1 C2 C2 117.7(5) . 2_657 ?
C1 C2 C3 125.6(3) . . ?
C3 C2 C2 116.7(4) . 2_657 ?
C4 C3 S1 142.7(3) . 2_657 ?
C4 C3 C15 110.2(4) . 2_657 ?
C2 C3 C4 118.8(3) . . ?
C2 C3 S1 98.6(2) . 2_657 ?
C2 C3 C15 130.9(4) . 2_657 ?
C15 C3 S1 32.5(2) 2_657 2_657 ?
C1 S1 C3 107.2(2) . 2_657 ?
C1 S1 H1B 171.5(14) . . ?
C1 S1 H1A 85.1(14) . . ?
C3 S1 H1B 80.3(14) 2_657 . ?
C3 S1 H1A 167.0(14) 2_657 . ?
C15 S1 C1 168.9(3) . . ?
C15 S1 C3 63.9(3) . 2_657 ?
C15 S1 H1B 16.7(15) . . ?
C15 S1 H1A 103.4(15) . . ?
C14 S1 C1 70.6(4) . . ?
C14 S1 C3 173.1(4) . 2_657 ?
C14 S1 C15 117.4(5) . . ?
C14 S1 H1B 101.4(15) . . ?
C14 S1 H1A 14.7(15) . . ?
H1B S1 H1A 87(2) . . ?
C3 C15 H1B 127(3) 2_657 . ?
S1 C15 C3 83.6(4) . 2_657 ?
S1 C15 C14 29.0(3) . . ?
S1 C15 H1B 149(3) . . ?
C14 C15 C3 112.3(5) . 2_657 ?
C14 C15 H1B 120(3) . . ?
C1 C14 H1A 126(3) . . ?
S1 C14 C1 80.5(5) . . ?
S1 C14 C15 33.6(4) . . ?
S1 C14 H1A 153(3) . . ?
C15 C14 C1 113.7(5) . . ?
C15 C14 H1A 120(3) . . ?


_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.610
