# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_053263_cl_200k_a
_database_code_depnum_ccdc_archive 'CCDC 2152460'
loop_
_audit_author_name
_audit_author_address
'Yu Li'
;Tianjin University
China
;
_audit_update_record             
;
2022-02-16 deposited with the CCDC.	2022-05-10 downloaded from the CCDC.
;
_audit_creation_date             2021-12-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H18 Cl4 N4'
_chemical_formula_sum            'C34 H18 Cl4 N4'
_chemical_formula_weight         624.32
_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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   8.26990(10)
_cell_length_b                   11.0285(2)
_cell_length_c                   31.2819(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.033(2)
_cell_angle_gamma                90
_cell_volume                     2831.59(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6960
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      74.6790
_cell_measurement_theta_min      2.8080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.057
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            8932
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.839
_diffrn_reflns_theta_min         2.847
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00 -23.00   0.50    0.10    --  -45.75 -73.00 -42.00  166
  2  ω    -67.00  24.00   0.50    0.10    --  -45.75  73.00  87.00  182
  3  ω     -9.00  59.00   0.50    0.10    --   45.75 -73.00 -42.00  136
  4  ω    -68.00 -42.00   0.50    0.40    -- -100.00  73.00  87.00   52
  5  ω   -173.00-148.00   0.50    0.40    -- -100.00 -73.00 -42.00   50
  6  ω     44.00 121.00   0.50    0.40    --  101.75 -73.00 -42.00  154
  7  ω     81.00 174.00   0.50    0.40    --  101.75  73.00  87.00  186
  8  ω   -114.00 -77.00   0.50    0.10    --  -45.75-125.00  90.00   74
  9  ω   -119.00 -84.00   0.50    0.40    -- -100.00 -30.00-120.00   70
 10  ω   -112.00 -64.00   0.50    0.40    -- -100.00  61.00 -30.00   96
 11  ω   -147.00-121.00   0.50    0.40    -- -100.00 -30.00-120.00   52
 12  ω   -171.00 -85.00   0.50    0.40    -- -100.00 -45.00   0.00  172
 13  ω     40.00  74.00   0.50    0.40    --  101.75-125.00-180.00   68
 14  ω     81.00 115.00   0.50    0.40    --  101.75-125.00-180.00   68
 15  ω     35.00  95.00   0.50    0.40    --  101.75 -94.00-120.00  120
 16  ω     49.00  87.00   0.50    0.40    --  101.75 -94.00-180.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1060545000
_diffrn_orient_matrix_UB_12      -0.1048254000
_diffrn_orient_matrix_UB_13      -0.0203775000
_diffrn_orient_matrix_UB_21      -0.0296281000
_diffrn_orient_matrix_UB_22      -0.0434246000
_diffrn_orient_matrix_UB_23      0.0451740000
_diffrn_orient_matrix_UB_31      -0.1520507000
_diffrn_orient_matrix_UB_32      0.0815193000
_diffrn_orient_matrix_UB_33      -0.0020677000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2595
_reflns_number_total             2783
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.00078(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0305
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+2.0407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0853
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C1(H1), C2(H2), C4(H4), C5(H5), C17(H17), C16(H16), C13(H13),
 C14(H14)
;
_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
Cl1 Cl 0.31257(4) 0.75597(3) 0.61303(2) 0.03264(13) Uani 1 1 d . . . . .
Cl2 Cl 0.52354(6) 0.14860(6) 0.77984(2) 0.05964(19) Uani 1 1 d . . . . .
N1 N 0.11065(14) 0.22595(10) 0.52989(4) 0.0219(2) Uani 1 1 d . . . . .
N2 N 0.14389(14) 0.02135(10) 0.58476(4) 0.0240(3) Uani 1 1 d . . . . .
C10 C 0.19918(16) 0.12813(12) 0.59782(4) 0.0219(3) Uani 1 1 d . . . . .
C6 C 0.22959(16) 0.35888(12) 0.58393(4) 0.0216(3) Uani 1 1 d . . . . .
C9 C 0.07190(16) 0.01083(12) 0.54288(4) 0.0214(3) Uani 1 1 d . . . . .
C8 C 0.05669(16) 0.11373(12) 0.51505(4) 0.0211(3) Uani 1 1 d . . . . .
C7 C 0.18037(16) 0.23389(12) 0.56977(4) 0.0206(3) Uani 1 1 d . . . . .
C11 C 0.01554(17) -0.10203(12) 0.52750(4) 0.0240(3) Uani 1 1 d . . . . .
H11 H 0.026003 -0.169355 0.545527 0.029 Uiso 1 1 calc R U . . .
C1 C 0.30392(17) 0.43247(13) 0.55575(4) 0.0244(3) Uani 1 1 d . . . . .
H1 H 0.336165 0.399264 0.530803 0.029 Uiso 1 1 calc R U . . .
C2 C 0.33021(17) 0.55465(13) 0.56455(4) 0.0267(3) Uani 1 1 d . . . . .
H2 H 0.378064 0.603968 0.545512 0.032 Uiso 1 1 calc R U . . .
C4 C 0.21487(17) 0.53014(13) 0.63140(4) 0.0257(3) Uani 1 1 d . . . . .
H4 H 0.186489 0.563229 0.656794 0.031 Uiso 1 1 calc R U . . .
C12 C 0.28035(17) 0.13499(12) 0.64294(4) 0.0230(3) Uani 1 1 d . . . . .
C5 C 0.18856(16) 0.40811(12) 0.62226(4) 0.0236(3) Uani 1 1 d . . . . .
H5 H 0.143307 0.358823 0.641792 0.028 Uiso 1 1 calc R U . . .
C3 C 0.28383(16) 0.60182(12) 0.60225(5) 0.0248(3) Uani 1 1 d . . . . .
C17 C 0.42852(18) 0.19400(14) 0.65305(5) 0.0282(3) Uani 1 1 d . . . . .
H17 H 0.477765 0.231288 0.631324 0.034 Uiso 1 1 calc R U . . .
C16 C 0.50387(19) 0.19800(15) 0.69512(5) 0.0329(3) Uani 1 1 d . . . . .
H16 H 0.603538 0.236945 0.701728 0.039 Uiso 1 1 calc R U . . .
C15 C 0.4287(2) 0.14338(16) 0.72688(5) 0.0354(4) Uani 1 1 d . . . . .
C13 C 0.2087(2) 0.07933(16) 0.67562(5) 0.0376(4) Uani 1 1 d . . . . .
H13 H 0.110221 0.038632 0.669156 0.045 Uiso 1 1 calc R U . . .
C14 C 0.2824(2) 0.08379(19) 0.71784(5) 0.0453(4) Uani 1 1 d . . . . .
H14 H 0.233668 0.046989 0.739756 0.054 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
Cl1 C3 1.7438(14) . ?
Cl2 C15 1.7451(15) . ?
N1 C8 1.3769(17) . ?
N1 C7 1.3114(17) . ?
N2 C10 1.3104(17) . ?
N2 C9 1.3759(17) . ?
C10 C7 1.4564(18) . ?
C10 C12 1.4888(18) . ?
C6 C7 1.4893(17) . ?
C6 C1 1.3953(19) . ?
C6 C5 1.3952(19) . ?
C9 C8 1.4264(18) . ?
C9 C11 1.3939(18) . ?
C8 C11 1.3964(19) 5_556 ?
C11 H11 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.3872(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.3876(19) . ?
C4 C3 1.382(2) . ?
C12 C17 1.389(2) . ?
C12 C13 1.386(2) . ?
C5 H5 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.386(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.374(2) . ?
C15 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(2) . ?
C14 H14 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
C7 N1 C8 117.87(11) . . ?
C10 N2 C9 117.80(11) . . ?
N2 C10 C7 121.63(11) . . ?
N2 C10 C12 116.15(12) . . ?
C7 C10 C12 122.21(11) . . ?
C1 C6 C7 118.41(12) . . ?
C1 C6 C5 119.28(12) . . ?
C5 C6 C7 121.97(12) . . ?
N2 C9 C8 120.64(12) . . ?
N2 C9 C11 119.42(12) . . ?
C11 C9 C8 119.93(12) . . ?
N1 C8 C9 120.57(12) . . ?
N1 C8 C11 119.19(12) . 5_556 ?
C11 C8 C9 120.24(12) 5_556 . ?
N1 C7 C10 121.44(12) . . ?
N1 C7 C6 114.66(11) . . ?
C10 C7 C6 123.83(11) . . ?
C9 C11 C8 119.83(12) . 5_556 ?
C9 C11 H11 120.1 . . ?
C8 C11 H11 120.1 5_556 . ?
C6 C1 H1 119.7 . . ?
C2 C1 C6 120.66(13) . . ?
C2 C1 H1 119.7 . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.74(13) . . ?
C3 C2 H2 120.6 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.07(13) . . ?
C17 C12 C10 121.50(12) . . ?
C13 C12 C10 119.52(13) . . ?
C13 C12 C17 118.97(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.40(13) . . ?
C4 C5 H5 119.8 . . ?
C2 C3 Cl1 119.03(11) . . ?
C4 C3 Cl1 119.18(11) . . ?
C4 C3 C2 121.78(13) . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.84(14) . . ?
C16 C17 H17 119.6 . . ?
C17 C16 H16 120.6 . . ?
C15 C16 C17 118.80(14) . . ?
C15 C16 H16 120.6 . . ?
C16 C15 Cl2 118.77(13) . . ?
C16 C15 C14 121.70(14) . . ?
C14 C15 Cl2 119.52(13) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.59(15) . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.08(15) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?

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
Cl2 C15 C14 C13 -179.49(15) . . . . ?
N2 C10 C7 N1 -1.6(2) . . . . ?
N2 C10 C7 C6 175.23(12) . . . . ?
N2 C10 C12 C17 133.42(14) . . . . ?
N2 C10 C12 C13 -45.27(19) . . . . ?
N2 C9 C8 N1 -1.4(2) . . . . ?
N2 C9 C8 C11 179.56(13) . . . 5_556 ?
N2 C9 C11 C8 -179.56(13) . . . 5_556 ?
C10 N2 C9 C8 -0.81(19) . . . . ?
C10 N2 C9 C11 178.31(12) . . . . ?
C10 C12 C17 C16 -178.98(13) . . . . ?
C10 C12 C13 C14 179.59(16) . . . . ?
C6 C1 C2 C3 1.1(2) . . . . ?
C9 N2 C10 C7 2.27(19) . . . . ?
C9 N2 C10 C12 -178.34(12) . . . . ?
C8 N1 C7 C10 -0.61(19) . . . . ?
C8 N1 C7 C6 -177.75(11) . . . . ?
C8 C9 C11 C8 -0.4(2) . . . 5_556 ?
C7 N1 C8 C9 2.04(19) . . . . ?
C7 N1 C8 C11 -178.91(13) . . . 5_556 ?
C7 C10 C12 C17 -47.19(19) . . . . ?
C7 C10 C12 C13 134.11(15) . . . . ?
C7 C6 C1 C2 170.42(13) . . . . ?
C7 C6 C5 C4 -170.39(13) . . . . ?
C11 C9 C8 N1 179.48(12) . . . . ?
C11 C9 C8 C11 0.4(2) . . . 5_556 ?
C1 C6 C7 N1 -43.03(17) . . . . ?
C1 C6 C7 C10 139.90(13) . . . . ?
C1 C6 C5 C4 2.8(2) . . . . ?
C1 C2 C3 Cl1 -178.68(11) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C12 C10 C7 N1 179.00(12) . . . . ?
C12 C10 C7 C6 -4.1(2) . . . . ?
C12 C17 C16 C15 -0.6(2) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C5 C6 C7 N1 130.19(14) . . . . ?
C5 C6 C7 C10 -46.88(19) . . . . ?
C5 C6 C1 C2 -3.0(2) . . . . ?
C5 C4 C3 Cl1 178.48(10) . . . . ?
C5 C4 C3 C2 -1.2(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C17 C12 C13 C14 0.9(3) . . . . ?
C17 C16 C15 Cl2 -179.93(12) . . . . ?
C17 C16 C15 C14 0.9(3) . . . . ?
C16 C15 C14 C13 -0.3(3) . . . . ?
C13 C12 C17 C16 -0.3(2) . . . . ?


_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 1.589
_oxdiff_exptl_absorpt_empirical_full_min 0.770
####################################################################### 
# 
# 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_exp_720
_database_code_depnum_ccdc_archive 'CCDC 2152465'
loop_
_audit_author_name
_audit_author_address
'Li Yu'
;Tianjin University
China
;
_audit_update_record             
;
2022-02-16 deposited with the CCDC.	2022-05-10 downloaded from the CCDC.
;
_audit_creation_date             2021-08-06
_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        4F-PQ
_chemical_formula_moiety         'C34 H18 F4 N4'
_chemical_formula_sum            'C34 H18 F4 N4'
_chemical_formula_weight         558.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H F N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   5.8574(3)
_cell_length_b                   7.9358(5)
_cell_length_c                   14.6368(8)
_cell_angle_alpha                84.831(5)
_cell_angle_beta                 88.443(4)
_cell_angle_gamma                72.261(5)
_cell_volume                     645.37(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1666
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.3450
_cell_measurement_theta_min      6.0600
_shelx_estimated_absorpt_T_max   0.863
_shelx_estimated_absorpt_T_min   0.740
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             286
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3975
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.009
_diffrn_reflns_theta_min         5.876
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  -8.00   1.00    8.10    --  -40.87 -77.00 -60.00   97
  2  ω    -30.00  -3.00   1.00    8.10    --  -40.87 125.00  60.00   27
  3  ω   -107.00 -15.00   1.00    8.10    --  -40.87 -57.00-180.00   92
  4  ω    -92.00 -24.00   1.00    8.10    --  -40.87 125.00  30.00   68
  5  ω    -29.00  11.00   1.00    8.10    --   40.87 -37.00  30.00   40
  6  ω    131.00 158.00   1.00   32.38    --  105.32  77.00 120.00   27
  7  ω     74.00 103.00   1.00   32.38    --  105.32  77.00 120.00   29
  8  ω     76.00 177.00   1.00   32.38    --  105.32  61.00-120.00  101
  9  ω     38.00  66.00   1.00   32.38    --  105.32 -94.00-180.00   28
 10  ω     34.00 127.00   1.00   32.38    --  105.32 -61.00-120.00   93
 11  ω     75.00 106.00   1.00   32.38    --  105.32 -94.00-180.00   31
 12  ω     92.00 170.00   1.00   32.38    --  105.32  61.00   0.00   78
 13  ω    103.00 140.00   1.00   32.38    --  105.32 125.00-180.00   37
 14  ω     74.00 107.00   1.00   32.38    --  105.32-105.00 -53.00   33
 15  ω     91.00 178.00   1.00   32.38    --  105.32  45.00 -60.00   87
 16  ω     77.00 106.00   1.00   32.38    --  105.32-125.00-180.00   29
 17  ω     32.00  82.00   1.00   32.38    --  105.32-125.00-120.00   50
 18  ω     33.00 112.00   1.00   32.38    --  105.32 -77.00  30.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0740067000
_diffrn_orient_matrix_UB_12      -0.0016143000
_diffrn_orient_matrix_UB_13      0.1018056000
_diffrn_orient_matrix_UB_21      -0.0559301000
_diffrn_orient_matrix_UB_22      0.2033097000
_diffrn_orient_matrix_UB_23      -0.0052200000
_diffrn_orient_matrix_UB_31      -0.2600946000
_diffrn_orient_matrix_UB_32      0.0226784000
_diffrn_orient_matrix_UB_33      -0.0278786000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1942
_reflns_number_total             2477
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      1.189
_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)+(0.0461P)²+0.7418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.1888
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C11(H11), C5(H5), C14(H14), C17(H17), C16(H16), C4(H4), C1(H1),
 C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.1401(4) 1.2990(3) 0.27810(16) 0.0685(7) Uani 1 1 d . . . . .
F1 F 1.0093(6) 0.7622(4) -0.08539(16) 0.0961(10) Uani 1 1 d . . . . .
N2 N 1.0574(4) 0.7344(4) 0.44718(18) 0.0430(6) Uani 1 1 d . . . . .
N1 N 1.4011(5) 0.5874(4) 0.31439(18) 0.0454(7) Uani 1 1 d . . . . .
C8 C 1.4517(5) 0.5456(4) 0.4066(2) 0.0406(7) Uani 1 1 d . . . . .
C6 C 1.1357(6) 0.7175(4) 0.1912(2) 0.0464(8) Uani 1 1 d . . . . .
C13 C 0.5845(6) 0.9244(5) 0.3905(2) 0.0451(7) Uani 1 1 d . . . . .
H13 H 0.598213 0.843392 0.441636 0.054 Uiso 1 1 calc R . . . .
C10 C 1.0145(6) 0.7759(4) 0.3593(2) 0.0412(7) Uani 1 1 d . . . . .
C9 C 1.2743(5) 0.6150(4) 0.4733(2) 0.0413(7) Uani 1 1 d . . . . .
C7 C 1.1889(6) 0.6932(4) 0.2909(2) 0.0426(7) Uani 1 1 d . . . . .
C12 C 0.7825(6) 0.9140(4) 0.3346(2) 0.0415(7) Uani 1 1 d . . . . .
C11 C 1.3256(6) 0.5695(5) 0.5661(2) 0.0449(8) Uani 1 1 d . . . . .
H11 H 1.211049 0.616073 0.609847 0.054 Uiso 1 1 calc R . . . .
C5 C 0.9464(6) 0.6712(5) 0.1578(2) 0.0511(8) Uani 1 1 d . . . . .
H5 H 0.846014 0.630666 0.198415 0.061 Uiso 1 1 calc R . . . .
C14 C 0.3679(6) 1.0523(5) 0.3718(2) 0.0477(8) Uani 1 1 d . . . . .
H14 H 0.235042 1.056907 0.408904 0.057 Uiso 1 1 calc R . . . .
C17 C 0.7607(6) 1.0414(5) 0.2602(2) 0.0497(8) Uani 1 1 d . . . . .
H17 H 0.892746 1.038217 0.222846 0.060 Uiso 1 1 calc R . . . .
C16 C 0.5463(6) 1.1716(5) 0.2414(2) 0.0531(9) Uani 1 1 d . . . . .
H16 H 0.532333 1.256752 0.192192 0.064 Uiso 1 1 calc R . . . .
C15 C 0.3535(6) 1.1725(5) 0.2973(2) 0.0490(8) Uani 1 1 d . . . . .
C4 C 0.9053(7) 0.6849(5) 0.0643(3) 0.0603(10) Uani 1 1 d . . . . .
H4 H 0.780625 0.651153 0.041467 0.072 Uiso 1 1 calc R . . . .
C1 C 1.2813(7) 0.7815(6) 0.1299(3) 0.0614(10) Uani 1 1 d . . . . .
H1 H 1.408404 0.813756 0.151652 0.074 Uiso 1 1 calc R . . . .
C3 C 1.0516(8) 0.7489(6) 0.0063(2) 0.0653(11) Uani 1 1 d . . . . .
C2 C 1.2372(8) 0.7972(6) 0.0363(3) 0.0715(12) Uani 1 1 d . . . . .
H2 H 1.333676 0.840284 -0.005071 0.086 Uiso 1 1 calc R . . . .


_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 C15 1.361(4) . ?
F1 C3 1.361(4) . ?
N2 C10 1.311(4) . ?
N2 C9 1.373(4) . ?
N1 C8 1.378(4) . ?
N1 C7 1.305(4) . ?
C8 C9 1.425(4) . ?
C8 C11 1.390(4) 2_866 ?
C6 C7 1.484(4) . ?
C6 C5 1.383(5) . ?
C6 C1 1.389(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.387(5) . ?
C13 C14 1.378(4) . ?
C10 C7 1.460(4) . ?
C10 C12 1.492(4) . ?
C9 C11 1.390(4) . ?
C12 C17 1.398(5) . ?
C11 H11 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.385(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(5) . ?
C17 H17 0.9300 . ?
C17 C16 1.377(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.375(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.364(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.389(5) . ?
C3 C2 1.354(7) . ?
C2 H2 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
C10 N2 C9 118.2(3) . . ?
C7 N1 C8 118.0(3) . . ?
N1 C8 C9 120.3(3) . . ?
N1 C8 C11 119.5(3) . 2_866 ?
C11 C8 C9 120.2(3) 2_866 . ?
C5 C6 C7 120.6(3) . . ?
C5 C6 C1 119.2(3) . . ?
C1 C6 C7 120.1(3) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C14 C13 C12 121.3(3) . . ?
N2 C10 C7 121.0(3) . . ?
N2 C10 C12 116.1(3) . . ?
C7 C10 C12 122.9(3) . . ?
N2 C9 C8 120.6(3) . . ?
N2 C9 C11 119.5(3) . . ?
C11 C9 C8 119.8(3) . . ?
N1 C7 C6 115.5(3) . . ?
N1 C7 C10 121.6(3) . . ?
C10 C7 C6 122.8(3) . . ?
C13 C12 C10 119.1(3) . . ?
C13 C12 C17 118.4(3) . . ?
C17 C12 C10 122.3(3) . . ?
C8 C11 H11 120.0 2_866 . ?
C9 C11 C8 119.9(3) . 2_866 ?
C9 C11 H11 120.0 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.5(4) . . ?
C4 C5 H5 119.8 . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.3(3) . . ?
C15 C14 H14 120.9 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.9(3) . . ?
C16 C17 H17 119.6 . . ?
C17 C16 H16 120.8 . . ?
C15 C16 C17 118.4(3) . . ?
C15 C16 H16 120.8 . . ?
F2 C15 C14 118.7(3) . . ?
F2 C15 C16 118.6(3) . . ?
C14 C15 C16 122.7(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 C5 118.6(4) . . ?
C3 C4 H4 120.7 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 120.1(4) . . ?
C2 C1 H1 120.0 . . ?
F1 C3 C4 118.1(4) . . ?
C2 C3 F1 119.2(4) . . ?
C2 C3 C4 122.7(4) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2 120.5 . . ?

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 C3 C2 C1 -179.2(4) . . . . ?
N2 C10 C7 N1 -6.1(5) . . . . ?
N2 C10 C7 C6 171.6(3) . . . . ?
N2 C10 C12 C13 -32.9(5) . . . . ?
N2 C10 C12 C17 142.8(3) . . . . ?
N2 C9 C11 C8 -177.4(3) . . . 2_866 ?
N1 C8 C9 N2 -4.8(5) . . . . ?
N1 C8 C9 C11 178.8(3) . . . . ?
C8 N1 C7 C6 -173.5(3) . . . . ?
C8 N1 C7 C10 4.3(5) . . . . ?
C8 C9 C11 C8 -1.0(6) . . . 2_866 ?
C6 C5 C4 C3 -1.6(6) . . . . ?
C6 C1 C2 C3 -0.2(6) . . . . ?
C13 C12 C17 C16 -1.6(5) . . . . ?
C13 C14 C15 F2 179.8(3) . . . . ?
C13 C14 C15 C16 -0.8(6) . . . . ?
C10 N2 C9 C8 3.1(5) . . . . ?
C10 N2 C9 C11 179.5(3) . . . . ?
C10 C12 C17 C16 -177.3(3) . . . . ?
C9 N2 C10 C7 2.0(5) . . . . ?
C9 N2 C10 C12 -176.5(3) . . . . ?
C7 N1 C8 C9 0.9(5) . . . . ?
C7 N1 C8 C11 178.8(3) . . . 2_866 ?
C7 C6 C5 C4 -176.4(3) . . . . ?
C7 C6 C1 C2 177.3(4) . . . . ?
C7 C10 C12 C13 148.6(3) . . . . ?
C7 C10 C12 C17 -35.8(5) . . . . ?
C12 C13 C14 C15 -1.4(5) . . . . ?
C12 C10 C7 N1 172.4(3) . . . . ?
C12 C10 C7 C6 -9.9(5) . . . . ?
C12 C17 C16 C15 -0.5(6) . . . . ?
C11 C8 C9 N2 177.4(3) 2_866 . . . ?
C11 C8 C9 C11 1.0(6) 2_866 . . . ?
C5 C6 C7 N1 119.9(4) . . . . ?
C5 C6 C7 C10 -57.9(5) . . . . ?
C5 C6 C1 C2 -0.4(6) . . . . ?
C5 C4 C3 F1 -179.9(3) . . . . ?
C5 C4 C3 C2 1.0(6) . . . . ?
C14 C13 C12 C10 178.4(3) . . . . ?
C14 C13 C12 C17 2.5(5) . . . . ?
C17 C16 C15 F2 -178.9(3) . . . . ?
C17 C16 C15 C14 1.7(6) . . . . ?
C4 C3 C2 C1 -0.1(7) . . . . ?
C1 C6 C7 N1 -57.9(5) . . . . ?
C1 C6 C7 C10 124.3(4) . . . . ?
C1 C6 C5 C4 1.3(5) . . . . ?

_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 1.446
_oxdiff_exptl_absorpt_empirical_full_min 0.585
