# 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_zqc114m
_database_code_depnum_ccdc_archive 'CCDC 2111795'
loop_
_audit_author_name
_audit_author_address
'Zongrui Wang'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2021-09-24 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H28 F4 N6'
_chemical_formula_iupac          ?
_chemical_formula_weight         764.76

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   8.9947(4)
_cell_length_b                   10.5212(4)
_cell_length_c                   10.7845(4)
_cell_angle_alpha                79.6858(13)
_cell_angle_beta                 67.3649(12)
_cell_angle_gamma                68.3715(14)
_cell_volume                     874.84(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3076
_cell_measurement_theta_min      2.6904
_cell_measurement_theta_max      32.9579
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             394

_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.4074

_diffrn_reflns_number            15345
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0963
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         33.74
_diffrn_reflns_theta_full        33.74
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       10

_refine_special_details          
;
;

_reflns_number_total             6778
_reflns_number_gt                4374
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1550
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_number_reflns         6778
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.2740P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.347
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8095(2) 0.51277(16) 0.66606(15) 0.0161(3) Uani d . . . 1 . .
C C2 0.9412(2) 0.39014(16) 0.62419(16) 0.0185(3) Uani d . . . 1 . .
H H2 0.94039 0.335599 0.563301 0.022 Uiso calc U . R 1 . .
C C3 1.0734(2) 0.35005(17) 0.67386(17) 0.0217(3) Uani d . . . 1 . .
H H3 1.163186 0.26612 0.646813 0.026 Uiso calc U . R 1 . .
C C4 1.0792(2) 0.42858(18) 0.76222(18) 0.0243(4) Uani d . . . 1 . .
H H4 1.171457 0.397563 0.794865 0.029 Uiso calc U . R 1 . .
C C5 0.9506(2) 0.55171(18) 0.80222(17) 0.0216(3) Uani d . . . 1 . .
H H5 0.953968 0.606039 0.86195 0.026 Uiso calc U . R 1 . .
C C6 0.8159(2) 0.59504(16) 0.75380(15) 0.0171(3) Uani d . . . 1 . .
C C7 0.6678(2) 0.71726(16) 0.77395(15) 0.0170(3) Uani d . . . 1 . .
C C8 0.6036(2) 0.83475(17) 0.84677(16) 0.0209(3) Uani d . . . 1 . .
H H8 0.66235 0.847711 0.897684 0.025 Uiso calc U . R 1 . .
C C9 0.4520(2) 0.93144(16) 0.84238(16) 0.0214(3) Uani d . . . 1 . .
H H9 0.404373 1.010635 0.893604 0.026 Uiso calc U . R 1 . .
C C10 0.3662(2) 0.91588(16) 0.76409(16) 0.0193(3) Uani d . . . 1 . .
H H10 0.262213 0.984866 0.763848 0.023 Uiso calc U . R 1 . .
C C11 0.4297(2) 0.80195(15) 0.68689(15) 0.0156(3) Uani d . . . 1 . .
C C12 0.5786(2) 0.70439(15) 0.69725(14) 0.0157(3) Uani d . . . 1 . .
C C13 0.3599(2) 0.78568(15) 0.58444(15) 0.0162(3) Uani d . . . 1 . .
C C14 0.4185(2) 0.87589(16) 0.45788(16) 0.0201(3) Uani d . . . 1 . .
H H14A 0.371618 0.97193 0.481706 0.03 Uiso calc U . R 1 . .
H H14B 0.37754 0.865518 0.389421 0.03 Uiso calc U . R 1 . .
H H14C 0.543389 0.847364 0.422333 0.03 Uiso calc U . R 1 . .
C C15 0.1648(2) 0.83277(17) 0.64031(18) 0.0236(4) Uani d . . . 1 . .
H H15A 0.126764 0.769745 0.714263 0.035 Uiso calc U . R 1 . .
H H15B 0.122293 0.833581 0.568926 0.035 Uiso calc U . R 1 . .
H H15C 0.120261 0.925126 0.673537 0.035 Uiso calc U . R 1 . .
C C16 0.4355(2) 0.63594(15) 0.54364(14) 0.0145(3) Uani d . . . 1 . .
C C17 0.58083(19) 0.54054(15) 0.56550(14) 0.0141(3) Uani d . . . 1 . .
C C18 0.6405(2) 0.40725(15) 0.52347(15) 0.0152(3) Uani d . . . 1 . .
H H18 0.737341 0.343238 0.541597 0.018 Uiso calc U . R 1 . .
C C19 0.37337(19) 0.53572(15) 0.94566(15) 0.0150(3) Uani d . . . 1 . .
C C20 0.4991(2) 0.41434(15) 0.91750(14) 0.0147(3) Uani d . . . 1 . .
C C21 0.63764(19) 0.36945(15) 0.96798(14) 0.0145(3) Uani d . . . 1 . .
C C22 0.7712(2) 0.24780(15) 0.93408(15) 0.0167(3) Uani d . . . 1 . .
C C23 0.7842(2) 0.15661(16) 0.84305(17) 0.0197(3) Uani d . . . 1 . .
C C24 0.9150(2) 0.20347(16) 0.97815(16) 0.0187(3) Uani d . . . 1 . .
F F1 0.25135(12) 0.56823(9) 0.89282(9) 0.0198(2) Uani d . . . 1 . .
F F2 0.49375(13) 0.33178(9) 0.83965(10) 0.0206(2) Uani d . . . 1 . .
N N1 0.66185(17) 0.58094(13) 0.63295(13) 0.0153(3) Uani d . . . 1 . .
N N2 0.8030(2) 0.08151(15) 0.76909(16) 0.0275(3) Uani d . . . 1 . .
N N3 1.03559(19) 0.16186(15) 1.00615(15) 0.0256(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.394(2) ?
C1 N1 . 1.406(2) ?
C1 C6 . 1.421(2) ?
C2 C3 . 1.385(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.395(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.384(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.394(2) ?
C5 H5 . 0.95 ?
C6 C7 . 1.445(2) ?
C7 C8 . 1.397(2) ?
C7 C12 . 1.406(2) ?
C8 C9 . 1.381(3) ?
C8 H8 . 0.95 ?
C9 C10 . 1.407(2) ?
C9 H9 . 0.95 ?
C10 C11 . 1.394(2) ?
C10 H10 . 0.95 ?
C11 C12 . 1.386(2) ?
C11 C13 . 1.524(2) ?
C12 N1 . 1.3909(19) ?
C13 C15 . 1.530(2) ?
C13 C16 . 1.538(2) ?
C13 C14 . 1.547(2) ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 C18 2_666 1.387(2) ?
C16 C17 . 1.399(2) ?
C17 C18 . 1.395(2) ?
C17 N1 . 1.4100(19) ?
C18 H18 . 0.95 ?
C19 F1 . 1.3346(17) ?
C19 C20 . 1.346(2) ?
C19 C21 2_667 1.436(2) ?
C20 F2 . 1.3363(16) ?
C20 C21 . 1.438(2) ?
C21 C22 . 1.383(2) ?
C22 C24 . 1.437(2) ?
C22 C23 . 1.437(2) ?
C23 N2 . 1.146(2) ?
C24 N3 . 1.147(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 N1 . . 131.59(14) ?
C2 C1 C6 . . 120.06(14) ?
N1 C1 C6 . . 108.30(13) ?
C3 C2 C1 . . 118.12(15) ?
C3 C2 H2 . . 120.9 ?
C1 C2 H2 . . 120.9 ?
C2 C3 C4 . . 122.31(16) ?
C2 C3 H3 . . 118.8 ?
C4 C3 H3 . . 118.8 ?
C5 C4 C3 . . 119.90(16) ?
C5 C4 H4 . . 120.1 ?
C3 C4 H4 . . 120.1 ?
C4 C5 C6 . . 119.17(15) ?
C4 C5 H5 . . 120.4 ?
C6 C5 H5 . . 120.4 ?
C5 C6 C1 . . 120.40(15) ?
C5 C6 C7 . . 132.15(15) ?
C1 C6 C7 . . 107.45(14) ?
C8 C7 C12 . . 118.97(15) ?
C8 C7 C6 . . 134.98(15) ?
C12 C7 C6 . . 106.05(13) ?
C9 C8 C7 . . 117.85(15) ?
C9 C8 H8 . . 121.1 ?
C7 C8 H8 . . 121.1 ?
C8 C9 C10 . . 121.79(15) ?
C8 C9 H9 . . 119.1 ?
C10 C9 H9 . . 119.1 ?
C11 C10 C9 . . 121.77(16) ?
C11 C10 H10 . . 119.1 ?
C9 C10 H10 . . 119.1 ?
C12 C11 C10 . . 115.06(14) ?
C12 C11 C13 . . 119.25(13) ?
C10 C11 C13 . . 125.34(14) ?
C11 C12 N1 . . 125.16(14) ?
C11 C12 C7 . . 124.48(14) ?
N1 C12 C7 . . 110.36(14) ?
C11 C13 C15 . . 110.88(13) ?
C11 C13 C16 . . 109.77(12) ?
C15 C13 C16 . . 111.15(13) ?
C11 C13 C14 . . 107.83(13) ?
C15 C13 C14 . . 108.96(13) ?
C16 C13 C14 . . 108.14(12) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C18 C16 C17 2_666 . 117.26(13) ?
C18 C16 C13 2_666 . 118.53(13) ?
C17 C16 C13 . . 124.16(13) ?
C18 C17 C16 . . 119.83(14) ?
C18 C17 N1 . . 121.30(14) ?
C16 C17 N1 . . 118.85(13) ?
C16 C18 C17 2_666 . 122.88(14) ?
C16 C18 H18 2_666 . 118.6 ?
C17 C18 H18 . . 118.6 ?
F1 C19 C20 . . 118.39(13) ?
F1 C19 C21 . 2_667 118.47(13) ?
C20 C19 C21 . 2_667 123.12(14) ?
F2 C20 C19 . . 118.17(13) ?
F2 C20 C21 . . 118.75(13) ?
C19 C20 C21 . . 123.08(13) ?
C22 C21 C19 . 2_667 123.02(14) ?
C22 C21 C20 . . 123.19(14) ?
C19 C21 C20 2_667 . 113.77(13) ?
C21 C22 C24 . . 124.32(14) ?
C21 C22 C23 . . 122.39(14) ?
C24 C22 C23 . . 113.18(14) ?
N2 C23 C22 . . 176.64(18) ?
N3 C24 C22 . . 175.21(17) ?
C12 N1 C1 . . 107.84(12) ?
C12 N1 C17 . . 118.95(13) ?
C1 N1 C17 . . 132.68(13) ?

