# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_ng0830
_database_code_depnum_ccdc_archive 'CCDC 1972034'
loop_
_audit_author_name
_audit_author_address
'ning wang'
;nanjing tech universtry
China
;
_audit_update_record             
;
2019-12-14 deposited with the CCDC.	2020-04-29 downloaded from the CCDC.
;
_audit_creation_date             2019-08-30
_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         'C26 H14 F6 N2 O4 S2'
_chemical_formula_sum            'C26 H14 F6 N2 O4 S2'
_chemical_formula_weight         596.51
_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                   4.7270(6)
_cell_length_b                   6.3735(4)
_cell_length_c                   19.4848(16)
_cell_angle_alpha                85.692(6)
_cell_angle_beta                 87.707(9)
_cell_angle_gamma                86.270(7)
_cell_volume                     583.77(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1544
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.6340
_cell_measurement_theta_min      3.1940
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74089
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             302
_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  0.0319
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4426
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.456
_diffrn_reflns_theta_min         2.098
_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 1.000
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  16.00   1.00    3.00    --  -11.59 -77.00 -90.00   92
  2  ω    -12.00  79.00   1.00    3.00    --   11.74  57.00-180.00   91
  3  ω    -60.00  39.00   1.00    3.00    --   11.74 -57.00  30.00   99
;
_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      0.0548992000
_diffrn_orient_matrix_UB_12      0.0476919000
_diffrn_orient_matrix_UB_13      -0.0313744000
_diffrn_orient_matrix_UB_21      -0.0157391000
_diffrn_orient_matrix_UB_22      -0.0941386000
_diffrn_orient_matrix_UB_23      -0.0163268000
_diffrn_orient_matrix_UB_31      -0.1392044000
_diffrn_orient_matrix_UB_32      0.0369791000
_diffrn_orient_matrix_UB_33      -0.0091335000
_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                2080
_reflns_number_total             2706
_reflns_odcompleteness_completeness 99.96
_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         0.378
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2706
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.083
_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)+(0.0289P)²+0.3448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12), C5(H5), C2(H2), C6(H6)
;
_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
S1 S 1.23896(14) 0.46049(10) 0.09574(4) 0.02119(19) Uani 1 1 d . . . . .
F1 F 1.3198(3) 0.2084(2) 0.00076(8) 0.0246(4) Uani 1 1 d . . . . .
F3 F 0.9113(3) 0.1803(3) 0.05347(9) 0.0300(4) Uani 1 1 d . . . . .
F2 F 1.2871(4) 0.0452(2) 0.10129(8) 0.0317(4) Uani 1 1 d . . . . .
O2 O 0.7481(4) 0.4858(3) 0.42482(9) 0.0180(4) Uani 1 1 d . . . . .
O1 O 0.0346(4) 0.9562(3) 0.34835(9) 0.0203(4) Uani 1 1 d . . . . .
N1 N 0.3809(4) 0.6896(3) 0.37292(10) 0.0133(5) Uani 1 1 d . . . . .
C10 C 0.3523(5) 0.9657(4) 0.44360(12) 0.0129(5) Uani 1 1 d . . . . .
C3 C 0.8239(5) 0.6694(4) 0.16814(13) 0.0165(5) Uani 1 1 d . . . . .
H3 H 0.865718 0.783073 0.137490 0.020 Uiso 1 1 calc R . . . .
C9 C 0.5689(5) 0.8229(4) 0.46703(12) 0.0125(5) Uani 1 1 d . . . . .
C12 C 0.7261(5) 0.8513(4) 0.52382(12) 0.0130(5) Uani 1 1 d . . . . .
H12 H 0.871877 0.755966 0.538885 0.016 Uiso 1 1 calc R . . . .
C1 C 0.5498(5) 0.5240(4) 0.26578(12) 0.0131(5) Uani 1 1 d . . . . .
C5 C 0.9089(5) 0.3046(4) 0.20832(13) 0.0159(5) Uani 1 1 d . . . . .
H5 H 1.010575 0.175456 0.205544 0.019 Uiso 1 1 calc R . . . .
C11 C 0.2298(5) 0.8811(4) 0.38295(12) 0.0135(5) Uani 1 1 d . . . . .
C2 C 0.6177(5) 0.6947(4) 0.22017(13) 0.0160(5) Uani 1 1 d . . . . .
H2 H 0.524151 0.826164 0.224685 0.019 Uiso 1 1 calc R . . . .
C6 C 0.6960(5) 0.3300(4) 0.25909(13) 0.0155(5) Uani 1 1 d . . . . .
H6 H 0.651028 0.215268 0.288954 0.019 Uiso 1 1 calc R . . . .
C4 C 0.9683(5) 0.4737(4) 0.16184(13) 0.0154(5) Uani 1 1 d . . . . .
C7 C 0.3157(5) 0.5475(4) 0.32050(13) 0.0148(5) Uani 1 1 d . . . . .
H7A H 0.142252 0.600995 0.298583 0.018 Uiso 1 1 calc R . . . .
H7B H 0.282751 0.409683 0.342901 0.018 Uiso 1 1 calc R . . . .
C8 C 0.5895(5) 0.6431(4) 0.42119(13) 0.0132(5) Uani 1 1 d . . . . .
C13 C 1.1836(5) 0.2134(4) 0.06204(13) 0.0192(6) Uani 1 1 d . . . . .


_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
S1 C4 1.781(2) . ?
S1 C13 1.790(3) . ?
F1 C13 1.335(3) . ?
F3 C13 1.337(3) . ?
F2 C13 1.346(3) . ?
O2 C8 1.212(3) . ?
O1 C11 1.216(3) . ?
N1 C11 1.396(3) . ?
N1 C7 1.469(3) . ?
N1 C8 1.392(3) . ?
C10 C9 1.393(3) . ?
C10 C12 1.392(3) 2_676 ?
C10 C11 1.488(4) . ?
C3 C2 1.389(3) . ?
C3 C4 1.393(3) . ?
C9 C12 1.387(4) . ?
C9 C8 1.501(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.389(3) . ?
C1 C7 1.514(3) . ?
C5 C6 1.393(3) . ?
C5 C4 1.390(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
C4 S1 C13 101.77(12) . . ?
C11 N1 C7 124.0(2) . . ?
C8 N1 C11 112.0(2) . . ?
C8 N1 C7 123.92(19) . . ?
C9 C10 C11 108.0(2) . . ?
C12 C10 C9 122.3(2) 2_676 . ?
C12 C10 C11 129.7(2) 2_676 . ?
C2 C3 C4 120.0(2) . . ?
C10 C9 C8 107.8(2) . . ?
C12 C9 C10 123.2(2) . . ?
C12 C9 C8 128.9(2) . . ?
C9 C12 C10 114.4(2) . 2_676 ?
C2 C1 C7 120.9(2) . . ?
C6 C1 C2 118.9(2) . . ?
C6 C1 C7 120.2(2) . . ?
C4 C5 C6 119.5(2) . . ?
O1 C11 N1 125.0(2) . . ?
O1 C11 C10 128.7(2) . . ?
N1 C11 C10 106.3(2) . . ?
C3 C2 C1 120.5(2) . . ?
C1 C6 C5 121.0(2) . . ?
C3 C4 S1 116.52(19) . . ?
C5 C4 S1 123.41(19) . . ?
C5 C4 C3 120.0(2) . . ?
N1 C7 C1 113.1(2) . . ?
O2 C8 N1 125.6(2) . . ?
O2 C8 C9 128.5(2) . . ?
N1 C8 C9 105.92(19) . . ?
F1 C13 S1 108.00(17) . . ?
F1 C13 F3 108.0(2) . . ?
F1 C13 F2 106.80(19) . . ?
F3 C13 S1 114.18(17) . . ?
F3 C13 F2 105.8(2) . . ?
F2 C13 S1 113.69(19) . . ?

_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 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.567
