# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# 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_ljff
_database_code_depnum_ccdc_archive 'CCDC 1952852'
loop_
_audit_author_name
_audit_author_address
'Hongliang Mu'
;Changchun Institute of Applied Chemistry
China
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2019-12-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H6 F6 N2 O2'
_chemical_formula_weight         372.23

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.7327(12)
_cell_length_b                   9.6358(9)
_cell_length_c                   13.0361(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1473.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2319
_cell_measurement_theta_min      2.7354
_cell_measurement_theta_max      26.3206

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7657
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.735
_diffrn_reflns_theta_max         26.405
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1514
_reflns_number_gt                1249
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+0.6635P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1514
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1028
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F3 F 0.04900(10) 1.09470(13) 0.35558(10) 0.0578(4) Uani 1 1 d . . . . .
F2 F 0.22938(10) 1.11765(12) 0.34988(9) 0.0511(4) Uani 1 1 d . . . . .
F1 F 0.15516(13) 0.95239(13) 0.43566(9) 0.0610(4) Uani 1 1 d . . . . .
O1 O 0.36570(11) 0.81256(16) 0.06757(11) 0.0439(4) Uani 1 1 d . . . . .
C7 C 0.14576(15) 1.02425(18) 0.34870(14) 0.0329(4) Uani 1 1 d . . . . .
C1 C 0.26252(14) 0.83199(18) 0.12270(13) 0.0312(4) Uani 1 1 d . . . . .
C2 C 0.05617(14) 0.85603(16) 0.22290(12) 0.0270(4) Uani 1 1 d . . . . .
C3 C 0.06864(15) 0.76913(17) 0.13774(13) 0.0313(4) Uani 1 1 d . . . . .
H3 H 0.0062 0.7185 0.1147 0.038 Uiso 1 1 calc R U . . .
C8 C 0.45516(15) 0.88102(19) 0.09662(14) 0.0340(4) Uani 1 1 d . . . . .
C4 C 0.15133(14) 0.93140(16) 0.25594(13) 0.0275(4) Uani 1 1 d . . . . .
C5 C 0.17159(15) 0.75668(18) 0.08689(14) 0.0334(4) Uani 1 1 d . . . . .
H5 H 0.1790 0.6990 0.0301 0.040 Uiso 1 1 calc R U . . .
C6 C 0.25555(14) 0.91932(17) 0.20564(13) 0.0295(4) Uani 1 1 d . . . . .
H6 H 0.3189 0.9692 0.2277 0.035 Uiso 1 1 calc R U . . .
N1 N 0.53716(14) 0.93756(18) 0.11755(13) 0.0443(4) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F3 0.0386(7) 0.0592(8) 0.0756(9) -0.0364(7) -0.0075(6) 0.0144(6)
F2 0.0467(7) 0.0498(7) 0.0569(7) -0.0221(6) 0.0069(6) -0.0160(6)
F1 0.1002(11) 0.0537(8) 0.0293(6) -0.0035(5) -0.0027(6) -0.0005(7)
O1 0.0305(7) 0.0569(9) 0.0443(8) -0.0172(7) 0.0069(6) -0.0038(6)
C7 0.0300(9) 0.0336(9) 0.0350(9) -0.0061(7) -0.0013(8) 0.0017(8)
C1 0.0275(9) 0.0358(9) 0.0303(8) 0.0007(7) 0.0015(7) 0.0029(7)
C2 0.0265(8) 0.0262(8) 0.0283(8) 0.0026(6) -0.0026(7) 0.0019(7)
C3 0.0302(9) 0.0312(8) 0.0325(9) -0.0021(7) -0.0052(7) -0.0030(7)
C8 0.0294(9) 0.0396(10) 0.0328(9) -0.0017(8) 0.0040(8) 0.0052(8)
C4 0.0293(9) 0.0259(8) 0.0273(8) 0.0006(7) -0.0036(7) 0.0031(7)
C5 0.0350(10) 0.0340(9) 0.0311(8) -0.0065(7) -0.0007(8) 0.0004(8)
C6 0.0261(8) 0.0299(9) 0.0326(8) -0.0013(7) -0.0038(7) -0.0016(7)
N1 0.0325(9) 0.0519(10) 0.0484(10) -0.0015(8) 0.0024(8) 0.0000(8)

_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
F3 C7 1.326(2) . ?
F2 C7 1.331(2) . ?
F1 C7 1.333(2) . ?
O1 C8 1.296(2) . ?
O1 C1 1.420(2) . ?
C7 C4 1.506(2) . ?
C1 C5 1.372(2) . ?
C1 C6 1.373(2) . ?
C2 C3 1.398(2) . ?
C2 C4 1.400(2) . ?
C2 C2 1.496(3) 3 ?
C3 C5 1.383(2) . ?
C3 H3 0.9300 . ?
C8 N1 1.139(2) . ?
C4 C6 1.392(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

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
C8 O1 C1 118.38(14) . . ?
F3 C7 F2 106.50(14) . . ?
F3 C7 F1 106.22(15) . . ?
F2 C7 F1 106.29(14) . . ?
F3 C7 C4 113.31(14) . . ?
F2 C7 C4 112.26(14) . . ?
F1 C7 C4 111.77(14) . . ?
C5 C1 C6 123.09(16) . . ?
C5 C1 O1 114.89(15) . . ?
C6 C1 O1 122.02(15) . . ?
C3 C2 C4 118.14(15) . . ?
C3 C2 C2 117.86(15) . 3 ?
C4 C2 C2 123.89(15) . 3 ?
C5 C3 C2 121.59(16) . . ?
C5 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
N1 C8 O1 175.98(19) . . ?
C6 C4 C2 120.81(15) . . ?
C6 C4 C7 117.78(15) . . ?
C2 C4 C7 121.38(15) . . ?
C1 C5 C3 118.04(16) . . ?
C1 C5 H5 121.0 . . ?
C3 C5 H5 121.0 . . ?
C1 C6 C4 118.33(16) . . ?
C1 C6 H6 120.8 . . ?
C4 C6 H6 120.8 . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046

_shelx_res_file                  
;

    ljff.res created by SHELXL-2014/7


TITL ljff in Pbcn
CELL 0.71073  11.7327   9.6358  13.0361  90.000  90.000  90.000
ZERR    4.00   0.0012   0.0009   0.0013   0.000   0.000   0.000
LATT 1
SYMM 0.5-X, 0.5-Y, 0.5+Z
SYMM -X, Y, 0.5-Z
SYMM 0.5+X, 0.5-Y, -Z
SFAC C  H  N  O  F
UNIT 64 24 8 8 24
L.S. 9
ACTA
BOND $H
FMAP 2
Size 0.35 0.38 0.30
PLAN 5
TEMP -88.5
TEMP 0
WGHT    0.051800    0.663500
FVAR       0.51883
MOLE 1
F3    5    0.048998    1.094696    0.355581    11.00000    0.03861    0.05922 =
         0.07563   -0.03644   -0.00749    0.01444
F2    5    0.229380    1.117647    0.349878    11.00000    0.04666    0.04984 =
         0.05694   -0.02208    0.00692   -0.01604
F1    5    0.155155    0.952390    0.435658    11.00000    0.10016    0.05368 =
         0.02928   -0.00354   -0.00269   -0.00051
O1    4    0.365698    0.812564    0.067566    11.00000    0.03050    0.05691 =
         0.04431   -0.01717    0.00688   -0.00382
C7    1    0.145763    1.024246    0.348704    11.00000    0.02999    0.03361 =
         0.03501   -0.00612   -0.00133    0.00167
C1    1    0.262524    0.831989    0.122697    11.00000    0.02747    0.03585 =
         0.03025    0.00067    0.00147    0.00287
C2    1    0.056174    0.856026    0.222904    11.00000    0.02650    0.02620 =
         0.02830    0.00257   -0.00261    0.00193
C3    1    0.068636    0.769126    0.137741    11.00000    0.03021    0.03116 =
         0.03246   -0.00213   -0.00518   -0.00300
AFIX  43
H3    2    0.006192    0.718475    0.114736    11.00000   -1.20000
AFIX   0
C8    1    0.455163    0.881023    0.096624    11.00000    0.02945    0.03963 =
         0.03278   -0.00169    0.00405    0.00517
C4    1    0.151333    0.931405    0.255939    11.00000    0.02925    0.02587 =
         0.02726    0.00056   -0.00363    0.00310
C5    1    0.171588    0.756679    0.086888    11.00000    0.03498    0.03401 =
         0.03111   -0.00650   -0.00069    0.00040
AFIX  43
H5    2    0.178964    0.698965    0.030095    11.00000   -1.20000
AFIX   0
C6    1    0.255553    0.919321    0.205639    11.00000    0.02612    0.02989 =
         0.03255   -0.00135   -0.00376   -0.00160
AFIX  43
H6    2    0.318851    0.969172    0.227687    11.00000   -1.20000
AFIX   0
N1    3    0.537155    0.937557    0.117554    11.00000    0.03254    0.05186 =
         0.04840   -0.00152    0.00242   -0.00004

HKLF 4

REM  ljff in Pbcn
REM R1 =  0.0425 for    1249 Fo > 4sig(Fo)  and  0.0526 for all    1514 data
REM    118 parameters refined using      0 restraints

END

WGHT      0.0517      0.6646

REM Highest difference peak  0.264,  deepest hole -0.230,  1-sigma level  0.046
Q1    1   0.1445  0.9715  0.2968  11.00000  0.05    0.26
Q2    1   0.0000  0.8617  0.2500  10.50000  0.05    0.23
Q3    1   0.2018  0.9041  0.2486  11.00000  0.05    0.23
Q4    1   0.0709  1.1532  0.2944  11.00000  0.05    0.23
Q5    1   0.0917  1.0057  0.4128  11.00000  0.05    0.23
;
_shelx_res_checksum              26979
