# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2201747'
loop_
_audit_author_name
_audit_author_address
'Iryna Andrusenko'
;IIT (Pontedera)
Italy
;
_audit_update_record             
;
2022-08-16 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        triphenylene-TCNQ
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H16 N4'
_chemical_formula_weight         432.49

_atom_type_scat_source           
;Doyle & Turner (1968)
;

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   6.8(1)
_cell_length_b                   11.2(2)
_cell_length_c                   17.7(4)
_cell_angle_alpha                78.4(5)
_cell_angle_beta                 83.9(5)
_cell_angle_gamma                72.9(5)
_cell_volume                     1261(44)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       nanocrystal
_exptl_crystal_colour            scarlet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_F_000             182
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.000
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.0335
_diffrn_radiation_type           electron
_diffrn_source                   '120 kV electron microscope'
_diffrn_source_type              'LaB6 gun'
_diffrn_measurement_device       'transmission electron microscope'
_diffrn_measurement_device_type  'Zeiss Libra 120'
_diffrn_detector                 'single-electron detector MEDIPIX'
_diffrn_detector_type            'ASI Timepix'
_diffrn_measurement_method       
'stepwise precession-assisted 3D electron diffration'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3423
_diffrn_reflns_av_unetI/netI     0.2264
_diffrn_reflns_av_R_equivalents  0.2117
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         0.091
_diffrn_reflns_theta_max         0.960
_diffrn_reflns_theta_full        0.960
_diffrn_measured_fraction_theta_max 0.662
_diffrn_measured_fraction_theta_full 0.662
_diffrn_reflns_Laue_measured_fraction_max 0.662
_diffrn_reflns_Laue_measured_fraction_full 0.662
_diffrn_reflns_point_group_measured_fraction_max 0.662
_diffrn_reflns_point_group_measured_fraction_full 0.662
_reflns_number_total             1747
_reflns_number_gt                712
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1747
_refine_ls_number_parameters     93
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.5020
_refine_ls_R_factor_gt           0.4104
_refine_ls_wR_factor_ref         0.7287
_refine_ls_wR_factor_gt          0.6773
_refine_ls_goodness_of_fit_ref   2.925
_refine_ls_restrained_S_all      2.896
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.006

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
H24 H 0.38(2) 0.732(6) 0.203(3) 0.05(5) Uiso 1 1 d D . . . .
C1 C -0.180(3) 0.671(2) 0.3776(14) 0.074(13) Uiso 1 1 d G U . . .
H1 H -0.208444 0.701261 0.423924 0.089 Uiso 1 1 calc R U . . .
C2 C -0.099(4) 0.541(2) 0.3782(15) 0.098(15) Uiso 1 1 d G U . . .
H2 H -0.073254 0.485166 0.424806 0.118 Uiso 1 1 calc R U . . .
C3 C -0.057(4) 0.4958(14) 0.3090(18) 0.078(13) Uiso 1 1 d G U . . .
H3 H -0.002388 0.409167 0.309345 0.093 Uiso 1 1 calc R U . . .
C4 C -0.095(4) 0.580(2) 0.2393(15) 0.061(11) Uiso 1 1 d G U . . .
H4 H -0.066712 0.549261 0.193001 0.074 Uiso 1 1 calc R U . . .
C5 C -0.176(4) 0.7092(19) 0.2388(14) 0.113(16) Uiso 1 1 d DG U . . .
C6 C -0.219(4) 0.7547(14) 0.3079(17) 0.052(10) Uiso 1 1 d DG U . . .
C7 C -0.277(3) 0.8833(13) 0.3124(12) 0.026(8) Uiso 1 1 d DG U . . .
C8 C -0.306(3) 0.9738(17) 0.2451(10) 0.031(8) Uiso 1 1 d DG U . . .
C9 C -0.369(3) 1.1022(16) 0.2493(11) 0.039(9) Uiso 1 1 d G U . . .
H9 H -0.388610 1.162794 0.204303 0.047 Uiso 1 1 calc R U . . .
C10 C -0.402(3) 1.1401(13) 0.3208(13) 0.054(10) Uiso 1 1 d G U . . .
H10 H -0.443650 1.226039 0.323654 0.065 Uiso 1 1 calc R U . . .
C11 C -0.372(3) 1.0496(18) 0.3881(10) 0.032(8) Uiso 1 1 d G U . . .
H11 H -0.394168 1.074936 0.435949 0.038 Uiso 1 1 calc R U . . .
C12 C -0.309(3) 0.9212(16) 0.3839(10) 0.047(9) Uiso 1 1 d G U . . .
H12 H -0.289645 0.860589 0.428892 0.056 Uiso 1 1 calc R U . . .
C13 C -0.263(4) 0.933(3) 0.1742(12) 0.103(15) Uiso 1 1 d DG U . . .
C14 C -0.294(5) 1.019(2) 0.1047(17) 0.105(16) Uiso 1 1 d G U . . .
H14 H -0.348444 1.105063 0.104667 0.127 Uiso 1 1 calc R U . . .
C15 C -0.242(6) 0.974(4) 0.0352(12) 0.21(3) Uiso 1 1 d G U . . .
H15 H -0.262627 1.031294 -0.011327 0.249 Uiso 1 1 calc R U . . .
C16 C -0.160(6) 0.845(4) 0.0352(14) 0.22(3) Uiso 1 1 d G U . . .
H16 H -0.125815 0.815529 -0.011267 0.260 Uiso 1 1 calc R U . . .
C17 C -0.130(6) 0.760(2) 0.105(2) 0.17(2) Uiso 1 1 d G U . . .
H17 H -0.074818 0.673532 0.104787 0.201 Uiso 1 1 calc R U . . .
C18 C -0.181(6) 0.804(2) 0.1743(14) 0.138(18) Uiso 1 1 d DG U . . .
C19 C 0.332(3) 0.6831(14) 0.3171(13) 0.023(8) Uiso 1 1 d DG U . . .
C20 C 0.283(3) 0.7337(17) 0.3845(11) 0.070(12) Uiso 1 1 d DG U . . .
H20 H 0.298071 0.680115 0.432286 0.083 Uiso 1 1 calc R U . . .
C21 C 0.212(3) 0.8645(18) 0.3804(12) 0.030(8) Uiso 1 1 d DG U . . .
H21 H 0.178733 0.898327 0.425502 0.036 Uiso 1 1 calc R U . . .
C22 C 0.189(3) 0.9446(14) 0.3090(13) 0.033(8) Uiso 1 1 d DG U . . .
C23 C 0.239(3) 0.8939(16) 0.2416(11) 0.042(10) Uiso 1 1 d DG U . . .
H23 H 0.223816 0.947532 0.193751 0.051 Uiso 1 1 calc R U . . .
C24 C 0.310(3) 0.7632(17) 0.2456(11) 0.027(8) Uiso 1 1 d DG U . . .
C25 C 0.383(5) 0.550(2) 0.3204(18) 0.041(9) Uiso 1 1 d D U . . .
C26 C 0.414(4) 0.457(3) 0.390(2) 0.049(10) Uiso 1 1 d D U . . .
C27 C 0.453(5) 0.499(3) 0.254(2) 0.038(9) Uiso 1 1 d D U . . .
C28 C 0.113(5) 1.078(2) 0.3109(19) 0.042(9) Uiso 1 1 d D U . . .
C29 C 0.063(5) 1.145(4) 0.372(2) 0.048(10) Uiso 1 1 d D U . . .
C30 C 0.084(4) 1.172(3) 0.242(2) 0.055(11) Uiso 1 1 d D U . . .
N31 N 0.426(4) 0.404(3) 0.450(2) 0.042(9) Uiso 1 1 d D U . . .
N32 N 0.503(5) 0.446(4) 0.205(2) 0.052(10) Uiso 1 1 d D U . . .
N33 N 0.043(6) 1.165(5) 0.431(3) 0.088(14) Uiso 1 1 d D U . . .
N34 N 0.070(6) 1.230(4) 0.183(2) 0.089(15) Uiso 1 1 d D 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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 C18 1.39(2) . ?
C6 C7 1.39(3) . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 C9 1.3900 . ?
C8 C13 1.39(3) . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C19 C20 1.3900 . ?
C19 C24 1.3900 . ?
C19 C25 1.42(4) . ?
C20 C21 1.3900 . ?
C21 C22 1.3900 . ?
C22 C23 1.3900 . ?
C22 C28 1.44(4) . ?
C23 C24 1.3900 . ?
C25 C26 1.44(4) . ?
C25 C27 1.39(4) . ?
C26 N31 1.10(4) . ?
C27 N32 1.12(3) . ?
C28 C30 1.43(4) . ?
C28 C29 1.39(4) . ?
C29 N33 1.10(4) . ?
C30 N34 1.10(4) . ?

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
C2 C1 C6 120.0 . . ?
C3 C2 C1 120.0 . . ?
C4 C3 C2 120.0 . . ?
C3 C4 C5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C18 113(2) . . ?
C4 C5 C18 125(2) . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 123.6(18) . . ?
C1 C6 C7 116(2) . . ?
C8 C7 C12 120.0 . . ?
C8 C7 C6 119.8(18) . . ?
C12 C7 C6 120.2(15) . . ?
C9 C8 C7 120.0 . . ?
C9 C8 C13 121.1(16) . . ?
C7 C8 C13 119(2) . . ?
C8 C9 C10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C12 C11 C10 120.0 . . ?
C11 C12 C7 120.0 . . ?
C14 C13 C18 120.0 . . ?
C14 C13 C8 122(3) . . ?
C18 C13 C8 118(2) . . ?
C15 C14 C13 120.0 . . ?
C14 C15 C16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C18 C17 C16 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 C5 114(3) . . ?
C13 C18 C5 125(2) . . ?
C20 C19 C24 120.0 . . ?
C20 C19 C25 120.3(17) . . ?
C24 C19 C25 119.3(18) . . ?
C21 C20 C19 120.0 . . ?
C20 C21 C22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C21 C22 C28 115.7(19) . . ?
C23 C22 C28 124.3(17) . . ?
C22 C23 C24 120.0 . . ?
C23 C24 C19 120.0 . . ?
C26 C25 C27 113(3) . . ?
C26 C25 C19 125(2) . . ?
C27 C25 C19 120(3) . . ?
N31 C26 C25 168(3) . . ?
N32 C27 C25 172(4) . . ?
C30 C28 C22 122(3) . . ?
C30 C28 C29 106(3) . . ?
C22 C28 C29 132(3) . . ?
N33 C29 C28 160(5) . . ?
N34 C30 C28 170(4) . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.091



# start Validation Reply Form
_vrf_ATOM007_shelx               
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: All atoms were refined assuming isotropic thermal parameters.
;
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: All avealiable data were used.
;
_vrf_RINTA01_shelx               
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: High residual values are expected for electron diffraction.
;
_vrf_GOODF01_shelx               
;
PROBLEM: The least squares goodness of fit parameter lies
RESPONSE: High GOOF values are expected for electron diffraction.
;
_vrf_PLAT082_shelx               
;
PROBLEM: High R1 Value .................................. 0.41 Report
RESPONSE: High residual values are expected for electron diffraction.
;
_vrf_PLAT084_shelx               
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.73 Report
RESPONSE: High residual values are expected for electron diffraction.
;
_vrf_PLAT183_shelx               
;
PROBLEM: Missing _cell_measurement_reflns_used Value .... Please Do !
RESPONSE: Cell parameters were determined by PETS2, which does not 
report these parameters.
;
_vrf_PLAT184_shelx               
;
PROBLEM: Missing _cell_measurement_theta_min Value ...... Please Do !
RESPONSE: Cell parameters were determined by PETS2, which does not 
report these parameters.
;
_vrf_PLAT185_shelx               
;
PROBLEM: Missing _cell_measurement_theta_max Value ...... Please Do !
RESPONSE: Cell parameters were determined by PETS2, which does not 
report these parameters.
;
_vrf_PLAT201_shelx               
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) ....... 18 Report
RESPONSE: All atoms were refined assuming isotropic thermal parameters.
;
_vrf_PLAT410_shelx               
;
PROBLEM: Short Intra H...H Contact H1 ..H12 . 1.72 Ang.
RESPONSE: Lower precision is expected for refinements based on 
electron diffraction.
;
_vrf_PLAT020_shelx               
;
PROBLEM: The Value of Rint is Greater Than 0.12 ......... 0.212 Report
RESPONSE: High Rint values are expected for electron diffraction. 
;
_vrf_PLAT149_shelx               
;
PROBLEM: s.u. on the alpha Angle is Too Large ....... 0.50 Degree
RESPONSE: High errors in cell parameter determination are expected 
for electron diffraction. 
;
_vrf_PLAT242_shelx               
;
PROBLEM: Low MainMol Ueq as Compared to Neighbors of C14 Check
RESPONSE: High values deviations are expected for electron diffraction.
;
_vrf_PLAT340_shelx               
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.04606 Ang.
RESPONSE: Lower precision is expected for refinements based on 
electron diffraction.
;
_vrf_PLAT601_shelx               
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of . 184 Ang**3
RESPONSE: ...
;
_vrf_PLAT085_shelx               
;
PROBLEM: SHELXL Default Weighting Scheme is not Optimized Please Check
RESPONSE: We used the standard Weighting Scheme.
;
_vrf_PLAT087_shelx               
;
PROBLEM: Unsatisfactory S value (Too High) .............. 2.92 Check
RESPONSE: High S value is expected for refinements based on 
electron diffraction.
;
_vrf_PLAT148_shelx               
;
PROBLEM: s.u. on the a - Axis is (Too) Large .... 0.100 Ang.
RESPONSE: Lower precision is expected for refinements based on 
electron diffraction.
;
_vrf_PLAT202_shelx               
;
PROBLEM: Isotropic non-H Atoms in Anion/Solvent ......... 16 Check
RESPONSE: All atoms were refined assuming isotropic thermal parameters.
;
_vrf_PLAT241_shelx               
;
PROBLEM: High MainMol Ueq as Compared to Neighbors of C2 Check
RESPONSE: High values deviations are expected for electron diffraction.
;
_vrf_PLAT790_shelx               
;
PROBLEM: Centre of Gravity not Within Unit Cell: Resd. 1 Note
RESPONSE: ...
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2201748'
loop_
_audit_author_name
_audit_author_address
'Iryna Andrusenko'
;IIT (Pontedera)
Italy
;
_audit_update_record             
;
2022-12-23 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'7,7,8,8-tetracyanoquinodimethane, 9,10-Benzophenanthrene Isochrysene Benzo[l]phenanthrene'
_chemical_name_common            'TCNQF2, Triphenylene'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H2 F2 N4, C18 H12'
_chemical_formula_sum            'C30 H14 F2 N4'
_chemical_formula_weight         468.46

_atom_type_scat_source           
;Doyle & Turner (1968)
;

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4(2)
_cell_length_b                   7.18(5)
_cell_length_c                   32.2(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.4(5)
_cell_angle_gamma                90
_cell_volume                     2156(50)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4250
_cell_measurement_theta_min      0.060
_cell_measurement_theta_max      0.970

_exptl_crystal_description       nanocrystal
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_F_000             375
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.014
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.0335
_diffrn_radiation_type           electron
_diffrn_source                   '120 kV electron microscope'
_diffrn_source_type              'LaB6 gun'
_diffrn_measurement_device       'transmission electron microscope'
_diffrn_measurement_device_type  'Zeiss Libra 120'
_diffrn_detector                 'single-electron detector MEDIPIX'
_diffrn_detector_type            'ASI Timepix'
_diffrn_measurement_method       
'stepwise precession-assisted 3D electron diffraction'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4250
_diffrn_reflns_av_unetI/netI     0.1746
_diffrn_reflns_av_R_equivalents  0.2382
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         0.060
_diffrn_reflns_theta_max         0.970
_diffrn_reflns_theta_full        0.970
_diffrn_measured_fraction_theta_max 0.702
_diffrn_measured_fraction_theta_full 0.702
_diffrn_reflns_Laue_measured_fraction_max 0.702
_diffrn_reflns_Laue_measured_fraction_full 0.702
_diffrn_reflns_point_group_measured_fraction_max 0.702
_diffrn_reflns_point_group_measured_fraction_full 0.702
_reflns_number_total             1641
_reflns_number_gt                955
_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       Pets
_computing_data_reduction        Pets
_computing_structure_solution    SIR2014
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    Mercury
_computing_publication_material  Shelxle
_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)+(0.4158P)²+6.7800P] 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         1641
_refine_ls_number_parameters     145
_refine_ls_number_restraints     165
_refine_ls_R_factor_all          0.3730
_refine_ls_R_factor_gt           0.3066
_refine_ls_wR_factor_ref         0.7159
_refine_ls_wR_factor_gt          0.6648
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.111
_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
C1_1 C 0.676(2) -0.142(3) 0.0359(5) 0.039(7) Uiso 1 1 d D U . . .
H1_1 H 0.581272 -0.149963 0.023147 0.047 Uiso 1 1 calc R U . . .
C2_1 C 0.783(2) -0.195(3) 0.0144(5) 0.042(7) Uiso 1 1 d D U . . .
H2_1 H 0.760344 -0.238984 -0.012928 0.050 Uiso 1 1 calc R U . . .
C3_1 C 0.924(2) -0.185(3) 0.0320(6) 0.060(8) Uiso 1 1 d D U . . .
H3_1 H 0.995113 -0.222085 0.016569 0.072 Uiso 1 1 calc R U . . .
C4_1 C 0.961(2) -0.120(4) 0.0720(6) 0.072(8) Uiso 1 1 d D U . . .
H4_1 H 1.057559 -0.112586 0.083479 0.086 Uiso 1 1 calc R U . . .
C5_1 C 0.855(2) -0.063(2) 0.0962(5) 0.049(7) Uiso 1 1 d D U . . .
C6_1 C 0.7074(19) -0.074(2) 0.0774(5) 0.046(7) Uiso 1 1 d D U . . .
C7_1 C 0.8925(19) 0.002(2) 0.1393(5) 0.052(7) Uiso 1 1 d D U . . .
C8_1 C 1.035(2) 0.011(3) 0.1594(6) 0.059(8) Uiso 1 1 d D U . . .
H8_1 H 1.108265 -0.022240 0.144496 0.071 Uiso 1 1 calc R U . . .
C9_1 C 1.068(2) 0.068(3) 0.2002(6) 0.059(8) Uiso 1 1 d D U . . .
H9_1 H 1.163536 0.073773 0.212657 0.071 Uiso 1 1 calc R U . . .
C10_1 C 0.960(2) 0.117(3) 0.2228(6) 0.046(7) Uiso 1 1 d D U . . .
H10_1 H 0.983714 0.154907 0.250604 0.055 Uiso 1 1 calc R U . . .
C11_1 C 0.821(2) 0.109(3) 0.2051(5) 0.043(7) Uiso 1 1 d D U . . .
H11_1 H 0.749893 0.139199 0.221317 0.052 Uiso 1 1 calc R U . . .
C12_1 C 0.7796(18) 0.057(2) 0.1627(5) 0.045(7) Uiso 1 1 d D U . . .
C13_1 C 0.6325(17) 0.052(2) 0.1430(5) 0.041(6) Uiso 1 1 d D U . . .
C14_1 C 0.519(2) 0.109(3) 0.1641(6) 0.051(7) Uiso 1 1 d D U . . .
H14_1 H 0.540221 0.148655 0.191828 0.061 Uiso 1 1 calc R U . . .
C15_1 C 0.381(2) 0.109(3) 0.1452(6) 0.053(8) Uiso 1 1 d D U . . .
H15_1 H 0.308300 0.146775 0.160170 0.064 Uiso 1 1 calc R U . . .
C16_1 C 0.3465(19) 0.053(3) 0.1038(6) 0.048(7) Uiso 1 1 d D U . . .
H16_1 H 0.251919 0.058865 0.090743 0.057 Uiso 1 1 calc R U . . .
C17_1 C 0.4505(19) -0.011(3) 0.0819(6) 0.034(6) Uiso 1 1 d D U . . .
H17_1 H 0.424986 -0.053857 0.054591 0.041 Uiso 1 1 calc R U . . .
C18_1 C 0.5954(18) -0.013(2) 0.1001(5) 0.042(6) Uiso 1 1 d D U . . .
C1_2 C 0.322(2) 0.619(3) 0.1697(7) 0.021(6) Uiso 1 1 d D U . . .
C2_2 C 0.527(3) 0.704(3) 0.2188(6) 0.050(8) Uiso 1 1 d D U . . .
C3_2 C 0.474(2) 0.625(2) 0.1788(5) 0.033(6) Uiso 1 1 d D U . . .
C4_2 C 0.5617(19) 0.569(2) 0.1505(5) 0.051(7) Uiso 1 1 d D U . . .
C5_2 C 0.4998(19) 0.508(3) 0.1097(5) 0.045(7) Uiso 1 1 d D U . . .
H5_2 H 0.400736 0.507642 0.102154 0.054 Uiso 1 1 calc R U . . .
C6_2 C 0.5855(18) 0.452(2) 0.0822(5) 0.049(7) Uiso 1 1 d D U . . .
C7_2 C 0.7385(18) 0.448(2) 0.0913(5) 0.040(6) Uiso 1 1 d D U . . .
C8_2 C 0.8005(19) 0.507(3) 0.1319(5) 0.040(7) Uiso 1 1 d D U . . .
H8_2 H 0.899456 0.506587 0.139521 0.048 Uiso 1 1 calc R U . . .
C9_2 C 0.7148(19) 0.565(3) 0.1594(5) 0.047(7) Uiso 1 1 d D U . . .
C10_2 C 0.8261(19) 0.392(2) 0.0631(5) 0.032(6) Uiso 1 1 d D U . . .
C11_2 C 0.769(3) 0.340(3) 0.0211(6) 0.037(7) Uiso 1 1 d D U . . .
C12_2 C 0.977(2) 0.379(3) 0.0741(8) 0.042(7) Uiso 1 1 d D U . . .
F1_2 F 0.525(3) 0.401(4) 0.0435(5) 0.066(8) Uiso 1 1 d D U . . .
F2_2 F 0.776(3) 0.616(5) 0.1981(6) 0.093(11) Uiso 1 1 d D U . . .
N1_2 N 0.200(2) 0.611(4) 0.1643(9) 0.055(8) Uiso 1 1 d D U . . .
N2_2 N 0.571(4) 0.772(4) 0.2503(7) 0.074(10) Uiso 1 1 d D U . . .
N3_2 N 0.721(4) 0.299(4) -0.0125(7) 0.065(9) Uiso 1 1 d D U . . .
N4_2 N 1.097(2) 0.362(4) 0.0832(9) 0.052(8) Uiso 1 1 d D 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
C1_1 C2_1 1.36(2) . ?
C1_1 C6_1 1.411(15) . ?
C2_1 C3_1 1.37(3) . ?
C3_1 C4_1 1.367(13) . ?
C4_1 C5_1 1.41(2) . ?
C5_1 C6_1 1.44(3) . ?
C5_1 C7_1 1.457(17) . ?
C6_1 C18_1 1.44(2) . ?
C7_1 C8_1 1.40(3) . ?
C7_1 C12_1 1.45(2) . ?
C8_1 C9_1 1.368(14) . ?
C9_1 C10_1 1.38(2) . ?
C10_1 C11_1 1.36(3) . ?
C11_1 C12_1 1.413(15) . ?
C12_1 C13_1 1.44(3) . ?
C13_1 C14_1 1.41(2) . ?
C13_1 C18_1 1.449(18) . ?
C14_1 C15_1 1.36(3) . ?
C15_1 C16_1 1.384(15) . ?
C16_1 C17_1 1.37(2) . ?
C17_1 C18_1 1.41(3) . ?
C1_2 N1_2 1.14(3) . ?
C1_2 C3_2 1.42(3) . ?
C2_2 N2_2 1.149(14) . ?
C2_2 C3_2 1.426(15) . ?
C3_2 C4_2 1.38(2) . ?
C4_2 C5_2 1.426(18) . ?
C4_2 C9_2 1.43(3) . ?
C5_2 C6_2 1.344(15) . ?
C6_2 F1_2 1.345(13) . ?
C6_2 C7_2 1.43(3) . ?
C7_2 C10_2 1.37(2) . ?
C7_2 C8_2 1.417(18) . ?
C8_2 C9_2 1.346(15) . ?
C9_2 F2_2 1.347(13) . ?
C10_2 C12_2 1.42(3) . ?
C10_2 C11_2 1.430(15) . ?
C11_2 N3_2 1.146(15) . ?
C12_2 N4_2 1.13(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
C2_1 C1_1 C6_1 120.7(15) . . ?
C1_1 C2_1 C3_1 121.5(16) . . ?
C2_1 C3_1 C4_1 120.6(13) . . ?
C3_1 C4_1 C5_1 120.8(16) . . ?
C4_1 C5_1 C6_1 118.2(15) . . ?
C4_1 C5_1 C7_1 121.7(16) . . ?
C6_1 C5_1 C7_1 120.1(13) . . ?
C1_1 C6_1 C18_1 121.3(16) . . ?
C1_1 C6_1 C5_1 118.2(12) . . ?
C18_1 C6_1 C5_1 120.5(16) . . ?
C8_1 C7_1 C12_1 118.3(16) . . ?
C8_1 C7_1 C5_1 122.3(14) . . ?
C12_1 C7_1 C5_1 119.3(15) . . ?
C9_1 C8_1 C7_1 121.9(14) . . ?
C8_1 C9_1 C10_1 119.9(15) . . ?
C11_1 C10_1 C9_1 120.8(16) . . ?
C10_1 C11_1 C12_1 121.8(14) . . ?
C11_1 C12_1 C13_1 122.9(14) . . ?
C11_1 C12_1 C7_1 117.2(15) . . ?
C13_1 C12_1 C7_1 119.9(16) . . ?
C14_1 C13_1 C12_1 121.9(17) . . ?
C14_1 C13_1 C18_1 117.3(14) . . ?
C12_1 C13_1 C18_1 120.8(13) . . ?
C15_1 C14_1 C13_1 122.2(16) . . ?
C14_1 C15_1 C16_1 120.2(13) . . ?
C17_1 C16_1 C15_1 120.7(15) . . ?
C16_1 C17_1 C18_1 121.0(16) . . ?
C17_1 C18_1 C6_1 122.1(16) . . ?
C17_1 C18_1 C13_1 118.6(12) . . ?
C6_1 C18_1 C13_1 119.3(15) . . ?
N1_2 C1_2 C3_2 177(2) . . ?
N2_2 C2_2 C3_2 178(3) . . ?
C4_2 C3_2 C1_2 122.6(17) . . ?
C4_2 C3_2 C2_2 123(2) . . ?
C1_2 C3_2 C2_2 114.2(17) . . ?
C3_2 C4_2 C5_2 119.6(17) . . ?
C3_2 C4_2 C9_2 124.1(15) . . ?
C5_2 C4_2 C9_2 116.3(11) . . ?
C6_2 C5_2 C4_2 119.5(16) . . ?
C5_2 C6_2 F1_2 118.5(17) . . ?
C5_2 C6_2 C7_2 124.0(13) . . ?
F1_2 C6_2 C7_2 117.5(13) . . ?
C10_2 C7_2 C8_2 119.4(16) . . ?
C10_2 C7_2 C6_2 123.9(15) . . ?
C8_2 C7_2 C6_2 116.7(11) . . ?
C9_2 C8_2 C7_2 119.5(16) . . ?
C8_2 C9_2 F2_2 118.3(17) . . ?
C8_2 C9_2 C4_2 124.1(13) . . ?
F2_2 C9_2 C4_2 117.6(14) . . ?
C7_2 C10_2 C12_2 122.1(18) . . ?
C7_2 C10_2 C11_2 121.2(19) . . ?
C12_2 C10_2 C11_2 116.6(18) . . ?
N3_2 C11_2 C10_2 179(3) . . ?
N4_2 C12_2 C10_2 177(2) . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.060



# start Validation Reply Form
_vrf_ATOM007_shelx               
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: All atoms were refined assuming isotropic thermal parameters.
;
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: All avealiable data were used.
;
_vrf_RINTA01_shelx               
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: High residual values are expected for electron diffraction.
;
_vrf_PLAT082_shelx               
;
PROBLEM: High R1 Value .................................. 0.31 Report
RESPONSE: High residual values are expected for electron diffraction.
;
_vrf_PLAT084_shelx               
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.72 Report
RESPONSE: High residual values are expected for electron diffraction.
;
_vrf_PLAT201_shelx               
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) ....... 36 Report
RESPONSE: All atoms were refined assuming isotropic thermal parameters.
;
_vrf_PLAT020_shelx               
;
PROBLEM: The Value of Rint is Greater Than 0.12 ......... 0.238 Report
RESPONSE: High residual values are expected for electron diffraction.
;
_vrf_PLAT149_shelx               
;
PROBLEM: s.u. on the beta Angle is Too Large ....... 0.50 Degree
RESPONSE: High errors in cell parameter determination are expected 
for electron diffraction. 
;
_vrf_PLAT340_shelx               
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.04 Ang. 
RESPONSE: Lower precision is expected for refinements based on 
electron diffraction.
;
_vrf_PLAT148_shelx               
;
PROBLEM: s.u. on the a - Axis is (Too) Large .... 0.200 Ang. 
RESPONSE: High errors in cell parameter determination are expected 
for electron diffraction.
;
_vrf_PLAT241_shelx               
;
PROBLEM: High MainMol Ueq as Compared to Neighbors of C4_1 Check 
RESPONSE: High values deviations are expected for electron diffraction.
;
_vrf_PLAT242_shelx               
;
PROBLEM: Low MainMol Ueq as Compared to Neighbors of C1_2 Check 
RESPONSE: High values deviations are expected for electron diffraction.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2201749'
loop_
_audit_author_name
_audit_author_address
'Iryna Andrusenko'
;IIT (Pontedera)
Italy
;
_audit_update_record             
;
2022-12-23 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Triphenylene-TCNQF4
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H12 F4 N4'
_chemical_formula_weight         504.45

_atom_type_scat_source           
;Doyle & Turner (1968)
;

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.8(4)
_cell_length_b                   17.4(3)
_cell_length_c                   9.20(18)
_cell_angle_alpha                90
_cell_angle_beta                 130.3(5)
_cell_angle_gamma                90
_cell_volume                     2173(76)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       nanocrystal
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             386
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.000
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.0335
_diffrn_radiation_type           electron
_diffrn_source                   '120 kV electron microscope'
_diffrn_source_type              'LaB6 gun'
_diffrn_measurement_device       'transmission electron microscope'
_diffrn_measurement_device_type  'Zeiss Libra 120'
_diffrn_detector                 'single-electron detector MEDIPIX'
_diffrn_detector_type            'ASI Timepix'
_diffrn_measurement_method       
'stepwise precession-assisted 3D electron diffration'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2606
_diffrn_reflns_av_unetI/netI     0.2036
_diffrn_reflns_av_R_equivalents  0.3314
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         0.090
_diffrn_reflns_theta_max         0.960
_diffrn_reflns_theta_full        0.960
_diffrn_measured_fraction_theta_max 0.731
_diffrn_measured_fraction_theta_full 0.731
_diffrn_reflns_Laue_measured_fraction_max 0.731
_diffrn_reflns_Laue_measured_fraction_full 0.731
_diffrn_reflns_point_group_measured_fraction_max 0.731
_diffrn_reflns_point_group_measured_fraction_full 0.731
_reflns_number_total             839
_reflns_number_gt                477
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)²] 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         839
_refine_ls_number_parameters     65
_refine_ls_number_restraints     86
_refine_ls_R_factor_all          0.4199
_refine_ls_R_factor_gt           0.3533
_refine_ls_wR_factor_ref         0.6369
_refine_ls_wR_factor_gt          0.5815
_refine_ls_goodness_of_fit_ref   2.461
_refine_ls_restrained_S_all      2.357
_refine_ls_shift/su_max          0.110
_refine_ls_shift/su_mean         0.009

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
C1 C 0.4222(7) 0.2658(9) 0.3796(10) 0.032(7) Uiso 1 1 d G . . . .
H1 H 0.410080 0.218275 0.321784 0.039 Uiso 1 1 calc R U . . .
C2 C 0.4004(6) 0.3330(9) 0.2770(7) 0.070(10) Uiso 1 1 d G . . . .
H2 H 0.373702 0.330365 0.150691 0.083 Uiso 1 1 calc R U . . .
C3 C 0.4184(6) 0.4040(9) 0.3634(9) 0.065(10) Uiso 1 1 d G . . . .
H3 H 0.403851 0.448941 0.294805 0.077 Uiso 1 1 calc R U . . .
C4 C 0.4583(4) 0.4079(9) 0.5522(9) 0.035(7) Uiso 1 1 d G . . . .
H4 H 0.470379 0.455429 0.610014 0.042 Uiso 1 1 calc R U . . .
C5 C 0.4801(4) 0.3407(9) 0.6548(6) 0.033(7) Uiso 1 1 d DG . . . .
C6 C 0.4620(7) 0.2697(9) 0.5684(9) 0.081(11) Uiso 1 1 d DG . . . .
C7 C 0.4801(5) 0.1984(9) 0.6550(7) 0.042(7) Uiso 1 1 d D . . . .
C11 C 0.4802(5) 0.0591(16) 0.6551(7) 0.075(11) Uiso 1 1 d D . . . .
H11 H 0.467016 0.012800 0.591833 0.090 Uiso 1 1 calc R U . . .
C12 C 0.4603(10) 0.1287(11) 0.560(3) 0.051(8) Uiso 1 1 d D . . . .
H12 H 0.433919 0.128677 0.434086 0.061 Uiso 1 1 calc R U . . .
C19 C 0.2247(7) 0.3092(13) 0.385(2) 0.031(7) Uiso 1 1 d D . . . .
C20 C 0.2050(10) 0.2360(10) 0.297(2) 0.008(5) Uiso 1 1 d D . . . .
C24 C 0.2671(9) 0.3260(17) 0.576(2) 0.037(7) Uiso 1 1 d D . . . .
C25 C 0.1982(11) 0.3721(13) 0.264(2) 0.016(5) Uiso 1 1 d D . . . .
C26 C 0.1554(10) 0.3739(16) 0.074(3) 0.023(6) Uiso 1 1 d D . . . .
C27 C 0.2200(13) 0.445(2) 0.332(4) 0.047(9) Uiso 1 1 d D . . . .
N31 N 0.1185(15) 0.360(2) -0.083(3) 0.056(8) Uiso 1 1 d D . . . .
N32 N 0.236(2) 0.508(2) 0.376(5) 0.098(13) Uiso 1 1 d D . . . .
F35 F 0.165(2) 0.226(2) 0.132(4) 0.075(9) Uiso 1 1 d . . . . .
F38 F 0.2855(18) 0.385(2) 0.649(4) 0.059(8) Uiso 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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C5 1.40(3) 2_656 ?
C5 C6 1.3900 . ?
C6 C7 1.40(2) . ?
C7 C7 1.40(3) 2_656 ?
C7 C12 1.40(2) . ?
C11 C11 1.40(3) 2_656 ?
C11 C12 1.40(2) . ?
C19 C25 1.41(3) . ?
C19 C20 1.42(3) . ?
C19 C24 1.42(4) . ?
C20 F35 1.20(4) . ?
C20 C24 1.43(3) 7_556 ?
C24 F38 1.15(4) . ?
C25 C27 1.35(4) . ?
C25 C26 1.38(4) . ?
C26 N31 1.17(4) . ?
C27 N32 1.15(4) . ?

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
C2 C1 C6 120.0 . . ?
C3 C2 C1 120.0 . . ?
C2 C3 C4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C5 C5 C6 117.2 2_656 . ?
C5 C5 C4 122.8 2_656 . ?
C6 C5 C4 120.0 . . ?
C7 C6 C5 125.6(15) . . ?
C7 C6 C1 114.4(9) . . ?
C5 C6 C1 120.0 . . ?
C7 C7 C6 117.2(8) 2_656 . ?
C7 C7 C12 119.9(13) 2_656 . ?
C6 C7 C12 122.9(19) . . ?
C11 C11 C12 119.9(14) 2_656 . ?
C11 C12 C7 120(3) . . ?
C25 C19 C20 114(2) . . ?
C25 C19 C24 117(2) . . ?
C20 C19 C24 128.6(18) . . ?
F35 C20 C19 125(2) . . ?
F35 C20 C24 123(3) . 7_556 ?
C19 C20 C24 113(2) . 7_556 ?
F38 C24 C20 112(3) . 7_556 ?
F38 C24 C19 129(2) . . ?
C20 C24 C19 119(2) 7_556 . ?
C27 C25 C26 109(2) . . ?
C27 C25 C19 121(2) . . ?
C26 C25 C19 130(2) . . ?
N31 C26 C25 166(3) . . ?
N32 C27 C25 175(3) . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.103



# start Validation Reply Form
_vrf_ATOM007_shelx               
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: All atoms were refined assuming isotropic thermal parameters.
;
_vrf_RINTA01_shelx               
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: High residual values are expected for electron diffraction.
;
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: All avealiable data were used.
;
_vrf_SHFSU01_shelx               
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.10
RESPONSE: Additional refinement circles do not improve this value.
;
_vrf_GOODF01_shelx               
;
PROBLEM: The least squares goodness of fit parameter lies
RESPONSE: High GOOF values are expected for electron diffraction.
;
_vrf_PLAT020_shelx               
;
PROBLEM: The Value of Rint is Greater Than 0.12 ......... 0.331 Report
RESPONSE: High residual values are expected for electron diffraction.
;
_vrf_PLAT082_shelx               
;
PROBLEM: High R1 Value .................................. 0.35 Report
RESPONSE: High residual values are expected for electron diffraction.
;
_vrf_PLAT084_shelx               
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.64 Report
RESPONSE: High residual values are expected for electron diffraction.
;
_vrf_PLAT183_shelx               
;
PROBLEM: Missing _cell_measurement_reflns_used Value .... Please Do ! 
RESPONSE: Cell parameters were determined by PETS2, which does not 
report these parameters.
;
_vrf_PLAT184_shelx               
;
PROBLEM: Missing _cell_measurement_theta_min Value ...... Please Do ! 
RESPONSE: Cell parameters were determined by PETS2, which does not 
report these parameters.
;
_vrf_PLAT185_shelx               
;
PROBLEM: Missing _cell_measurement_theta_max Value ...... Please Do ! 
RESPONSE: Cell parameters were determined by PETS2, which does not 
report these parameters.
;
_vrf_PLAT410_shelx               
;
PROBLEM: Short Intra H...H Contact H1 ..H12 . 1.76 Ang. 
RESPONSE: High values deviations are expected for electron diffraction.
;
_vrf_PLAT080_shelx               
;
PROBLEM: Maximum Shift/Error ............................ 0.11 Why ? 
RESPONSE: High values deviations are expected for electron diffraction.
;
_vrf_PLAT149_shelx               
;
PROBLEM: s.u. on the beta Angle is Too Large ....... 0.50 Degree
RESPONSE: High values deviations are expected for electron diffraction.
;
_vrf_PLAT201_shelx               
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) ....... 10 Report
RESPONSE: All atoms were refined assuming isotropic thermal parameters.
;
_vrf_PLAT340_shelx               
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.03778 Ang. 
RESPONSE: High values deviations are expected for electron diffraction.
;
_vrf_PLAT085_shelx               
;
PROBLEM: SHELXL Default Weighting Scheme is not Optimized Please Check 
RESPONSE: We used the default weighting scheme.
;
_vrf_PLAT087_shelx               
;
PROBLEM: Unsatisfactory S value (Too High) .............. 2.46 Check 
RESPONSE: High residual values are expected for electron diffraction.
;
_vrf_PLAT148_shelx               
;
PROBLEM: s.u. on the a - Axis is (Too) Large .... 0.400 Ang. 
RESPONSE: High values deviations are expected for electron diffraction.
;
_vrf_PLAT202_shelx               
;
PROBLEM: Isotropic non-H Atoms in Anion/Solvent ......... 9 Check 
RESPONSE: All atoms were refined assuming isotropic thermal parameters.
;
_vrf_PLAT241_shelx               
;
PROBLEM: High MainMol Ueq as Compared to Neighbors of C2 Check 
RESPONSE: High values deviations are expected for electron diffraction.
;
_vrf_PLAT242_shelx               
;
PROBLEM: Low MainMol Ueq as Compared to Neighbors of C20 Check 
RESPONSE: High values deviations are expected for electron diffraction.
;
# end Validation Reply Form
