# 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_45
_database_code_depnum_ccdc_archive 'CCDC 2076932'
loop_
_audit_author_name
_audit_author_address
'wang  rong'
;Hunan  University
China
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2021-09-06 downloaded from the CCDC.
;
_audit_creation_date             2021-01-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H7 F4 N O2'
_chemical_formula_sum            'C14 H7 F4 N O2'
_chemical_formula_weight         297.21
_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'

_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                   5.9650(6)
_cell_length_b                   7.5856(11)
_cell_length_c                   13.5287(15)
_cell_angle_alpha                82.212(11)
_cell_angle_beta                 82.531(9)
_cell_angle_gamma                88.960(10)
_cell_volume                     601.36(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1336
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      28.1300
_cell_measurement_theta_min      2.9310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95174
_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    1.641
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3832
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.710
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(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 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    -58.00  35.00   1.00    1.00    --   12.05 -57.00  90.00   93
  2  ω    -16.00  79.00   1.00    1.00    --   12.05  77.00   0.00   95
  3  ω    -16.00  83.00   1.00    1.00    --   12.05  57.00-120.00   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      0.0232291000
_diffrn_orient_matrix_UB_12      0.0369914000
_diffrn_orient_matrix_UB_13      0.0430089000
_diffrn_orient_matrix_UB_21      0.1150673000
_diffrn_orient_matrix_UB_22      0.0108563000
_diffrn_orient_matrix_UB_23      -0.0208953000
_diffrn_orient_matrix_UB_31      -0.0245470000
_diffrn_orient_matrix_UB_32      0.0861441000
_diffrn_orient_matrix_UB_33      -0.0236870000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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                1595
_reflns_number_total             2113
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2113
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.081
_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)+(0.0435P)²+0.0474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1060
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C7, N1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim C7: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
4.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 -0.0580(2) 0.47612(15) 0.63254(10) 0.0409(4) Uani 1 1 d . . . . .
F2 F -0.0427(2) 0.46739(15) 0.83398(10) 0.0444(4) Uani 1 1 d . . . . .
F3 F 0.3101(2) 0.31829(17) 0.91920(9) 0.0474(4) Uani 1 1 d . . . . .
F4 F 0.6611(2) 0.17421(15) 0.80815(9) 0.0400(4) Uani 1 1 d . . . . .
O1 O 0.3327(2) 0.31875(16) 0.51782(10) 0.0290(4) Uani 1 1 d . . . . .
O2 O 0.8882(3) 0.10653(19) 0.11632(11) 0.0380(4) Uani 1 1 d . . . . .
N1 N 0.6349(3) 0.19353(19) 0.58572(12) 0.0244(4) Uani 1 1 d . U . . .
C1 C 0.2983(3) 0.3300(2) 0.61936(15) 0.0251(5) Uani 1 1 d . . . . .
C2 C 0.1177(4) 0.4016(2) 0.67450(17) 0.0297(5) Uani 1 1 d . . . . .
C3 C 0.1268(4) 0.3960(3) 0.77596(17) 0.0315(5) Uani 1 1 d . . . . .
C4 C 0.3085(4) 0.3197(3) 0.81955(16) 0.0317(5) Uani 1 1 d . . . . .
C5 C 0.4877(4) 0.2487(2) 0.76322(16) 0.0287(5) Uani 1 1 d . . . . .
C6 C 0.4827(3) 0.2542(2) 0.66097(15) 0.0251(5) Uani 1 1 d . . . . .
C7 C 0.5401(4) 0.2354(2) 0.50451(16) 0.0273(5) Uani 1 1 d . U . . .
C8 C 0.6252(3) 0.2041(2) 0.40281(15) 0.0245(5) Uani 1 1 d . . . . .
C9 C 0.4964(3) 0.2467(2) 0.32435(15) 0.0268(5) Uani 1 1 d . . . . .
H9 H 0.353070 0.295425 0.337127 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5789(4) 0.2174(3) 0.22711(15) 0.0286(5) Uani 1 1 d . . . . .
H10 H 0.492283 0.247342 0.174888 0.034 Uiso 1 1 calc R U . . .
C11 C 0.7913(4) 0.1431(2) 0.20876(15) 0.0269(5) Uani 1 1 d . . . . .
C12 C 0.9219(4) 0.0990(2) 0.28662(16) 0.0292(5) Uani 1 1 d . . . . .
H12 H 1.064254 0.048598 0.273906 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8392(4) 0.1302(2) 0.38285(16) 0.0279(5) Uani 1 1 d . . . . .
H13 H 0.927087 0.101807 0.434759 0.033 Uiso 1 1 calc R U . . .
C14 C 0.7670(5) 0.1594(3) 0.03299(17) 0.0463(6) Uani 1 1 d . . . . .
H14A H 0.852563 0.128297 -0.027322 0.069 Uiso 1 1 calc R U . . .
H14B H 0.743185 0.285744 0.026104 0.069 Uiso 1 1 calc R U . . .
H14C H 0.623518 0.099754 0.044080 0.069 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 C2 1.336(2) . ?
F2 C3 1.350(2) . ?
F3 C4 1.348(2) . ?
F4 C5 1.344(2) . ?
O1 C1 1.376(2) . ?
O1 C7 1.381(2) . ?
O2 C11 1.369(2) . ?
O2 C14 1.426(3) . ?
N1 C6 1.394(2) . ?
N1 C7 1.299(3) . ?
C1 C2 1.375(3) . ?
C1 C6 1.381(3) . ?
C2 C3 1.376(3) . ?
C3 C4 1.381(3) . ?
C4 C5 1.376(3) . ?
C5 C6 1.382(3) . ?
C7 C8 1.452(3) . ?
C8 C9 1.390(3) . ?
C8 C13 1.394(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.389(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(3) . ?
C11 C12 1.391(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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
C1 O1 C7 103.55(15) . . ?
C11 O2 C14 117.31(17) . . ?
C7 N1 C6 104.02(17) . . ?
O1 C1 C6 107.86(17) . . ?
C2 C1 O1 128.8(2) . . ?
C2 C1 C6 123.3(2) . . ?
F1 C2 C1 122.4(2) . . ?
F1 C2 C3 120.81(19) . . ?
C1 C2 C3 116.8(2) . . ?
F2 C3 C2 119.8(2) . . ?
F2 C3 C4 119.2(2) . . ?
C2 C3 C4 121.0(2) . . ?
F3 C4 C3 118.74(19) . . ?
F3 C4 C5 119.8(2) . . ?
C5 C4 C3 121.4(2) . . ?
F4 C5 C4 119.88(19) . . ?
F4 C5 C6 121.58(19) . . ?
C4 C5 C6 118.5(2) . . ?
C1 C6 N1 109.30(18) . . ?
C1 C6 C5 118.91(19) . . ?
C5 C6 N1 131.8(2) . . ?
O1 C7 C8 116.83(18) . . ?
N1 C7 O1 115.27(17) . . ?
N1 C7 C8 127.90(19) . . ?
C9 C8 C7 121.05(19) . . ?
C9 C8 C13 119.05(19) . . ?
C13 C8 C7 119.90(19) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.30(19) . . ?
C11 C10 H10 120.3 . . ?
O2 C11 C10 124.26(19) . . ?
O2 C11 C12 115.24(18) . . ?
C10 C11 C12 120.50(19) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.5(2) . . ?
C12 C13 H13 119.7 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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 C2 C3 F2 -0.4(3) . . . . ?
F1 C2 C3 C4 -179.76(17) . . . . ?
F2 C3 C4 F3 0.3(3) . . . . ?
F2 C3 C4 C5 -178.53(17) . . . . ?
F3 C4 C5 F4 1.7(3) . . . . ?
F3 C4 C5 C6 -179.15(17) . . . . ?
F4 C5 C6 N1 -0.4(3) . . . . ?
F4 C5 C6 C1 178.96(16) . . . . ?
O1 C1 C2 F1 -0.7(3) . . . . ?
O1 C1 C2 C3 -179.77(17) . . . . ?
O1 C1 C6 N1 -0.3(2) . . . . ?
O1 C1 C6 C5 -179.78(16) . . . . ?
O1 C7 C8 C9 -3.9(3) . . . . ?
O1 C7 C8 C13 176.17(16) . . . . ?
O2 C11 C12 C13 -179.89(17) . . . . ?
N1 C7 C8 C9 175.79(17) . . . . ?
N1 C7 C8 C13 -4.2(3) . . . . ?
C1 O1 C7 N1 0.4(2) . . . . ?
C1 O1 C7 C8 -179.87(15) . . . . ?
C1 C2 C3 F2 178.61(16) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C1 C6 N1 179.71(17) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C2 C3 C4 F3 179.63(17) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 F4 -179.48(17) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 N1 -179.51(18) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C6 N1 C7 O1 -0.6(2) . . . . ?
C6 N1 C7 C8 179.73(18) . . . . ?
C6 C1 C2 F1 179.24(16) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C7 O1 C1 C2 179.93(19) . . . . ?
C7 O1 C1 C6 -0.1(2) . . . . ?
C7 N1 C6 C1 0.6(2) . . . . ?
C7 N1 C6 C5 179.9(2) . . . . ?
C7 C8 C9 C10 179.69(17) . . . . ?
C7 C8 C13 C12 179.67(17) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C8 C13 C12 -0.3(3) . . . . ?
C9 C10 C11 O2 179.22(17) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C8 0.6(3) . . . . ?
C13 C8 C9 C10 -0.3(3) . . . . ?
C14 O2 C11 C10 4.2(3) . . . . ?
C14 O2 C11 C12 -176.23(18) . . . . ?

_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 1.247
_oxdiff_exptl_absorpt_empirical_full_min 0.763
