# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_PTCDI_Ph_0_1MPa
_database_code_depnum_ccdc_archive 'CCDC 2253183'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PTCDI_Ph_0_1MPa     
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.360 Why?  
RESPONSE: These data come from high-pressure experiment and part of the 
reflection cannot be collected, due to the DAC opening angle and the 
measurement strategy. 
;
_vrf_PLAT026_PTCDI_Ph_0_1MPa     
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        38% Check 
RESPONSE: This low value is due to the the overall poor diffraction quality of 
the crystal.
;
_vrf_PLAT088_PTCDI_Ph_0_1MPa     
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.51 Note  
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber.
;
_vrf_PLAT149_PTCDI_Ph_0_1MPa     
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.06 Degree
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT340_PTCDI_Ph_0_1MPa     
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.012 Ang.   
RESPONSE: These data come from high-pressure experiment and part of the 
reflection cannot be collected, affecting bond precision. In addition, 
despite multiple attempts to grow better diffracting crystals, it was not 
successful.
;
_vrf_PLAT911_PTCDI_Ph_0_1MPa     
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        511 Report 
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2023-03-30

_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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 -0.0011 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0016 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0014 0.0018 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.72(3)
_cell_length_b                   4.0187(8)
_cell_length_c                   18.355(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.55(6)
_cell_angle_gamma                90
_cell_volume                     1220(3)
_cell_formula_units_Z            2
_cell_measurement_pressure       100
_cell_measurement_reflns_used    176
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.7750
_cell_measurement_theta_min      2.5850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.041
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.360
_diffrn_reflns_Laue_measured_fraction_max 0.332
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            2508
_diffrn_reflns_point_group_measured_fraction_full 0.360
_diffrn_reflns_point_group_measured_fraction_max 0.332
_diffrn_reflns_theta_full        14.237
_diffrn_reflns_theta_max         17.020
_diffrn_reflns_theta_min         2.580
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Eiger 9M CdTe'
_diffrn_measured_fraction_theta_full 0.360
_diffrn_measured_fraction_theta_max 0.332
_diffrn_measurement_details      
;
 Data were collected at room conditions (296 K / 0.1 MPa)
;
_diffrn_measurement_device_type  synchrotron
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_suport 'diamond anvil cell'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.40989
_diffrn_source                   'undulator, ID15B, ESRF'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                465
_reflns_number_total             1236
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.074
_refine_diff_density_min         -0.077
_refine_diff_density_rms         0.019
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1236
_refine_ls_number_restraints     312
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      0.861
_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)+(0.0328P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.1027
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C13, C14, C15, C16, C17, C18
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C14 \\sim C13 \\sim C18: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
Uanis(O2) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C10) \\sim
Ueq, Uanis(C7) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C2)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C15) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C3)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C16) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C17) \\sim Ueq, : with sigma
of 0.05 and sigma for terminal atoms of 0.05
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.001
4. Rigid body (RIGU) restrains
 C18, C17, C16, C15, C14, C13
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C11, N1, C1, O1, O2, C2, C12, C10, C9, C8, C7, C6, C5, C4, C3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C15(H15), C4(H4), C3(H3), C14(H14), C16(H16), C18(H18),
 C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8291(6) 0.0505(8) 0.65742(15) 0.071(3) Uani 1 1 d . U . . .
O1 O 0.6857(4) 0.6103(5) 0.81156(9) 0.063(4) Uani 1 1 d . U . . .
N1 N 0.7614(6) 0.3473(8) 0.73529(15) 0.052(3) Uani 1 1 d . U . . .
C10 C 0.7025(7) 0.2612(9) 0.60445(17) 0.049(3) Uani 1 1 d . U . . .
C7 C 0.5748(7) 0.3386(9) 0.48695(18) 0.049(3) Uani 1 1 d . U . . .
C1 C 0.6920(8) 0.5081(10) 0.74901(19) 0.045(3) Uani 1 1 d . U . . .
C8 C 0.6450(8) 0.1872(9) 0.4769(2) 0.056(3) Uani 1 1 d . U . . .
H8 H 0.650153 0.107153 0.430292 0.067 Uiso 1 1 calc R U . . .
C2 C 0.6234(7) 0.5473(9) 0.68810(16) 0.044(3) Uani 1 1 d . U . . .
C9 C 0.7102(6) 0.1466(8) 0.53437(14) 0.056(3) Uani 1 1 d . U . . .
H9 H 0.757754 0.044624 0.525514 0.067 Uiso 1 1 calc R U . . .
C5 C 0.4941(7) 0.6262(9) 0.57263(17) 0.046(3) Uani 1 1 d . U . . .
C11 C 0.7719(8) 0.2109(12) 0.6649(2) 0.056(3) Uani 1 1 d . U . . .
C15 C 0.8880(9) 0.1603(13) 0.9152(3) 0.071(4) Uani 1 1 d . U . . .
H15 H 0.883227 0.061848 0.960187 0.085 Uiso 1 1 calc R U . . .
C4 C 0.4904(5) 0.7485(7) 0.64321(14) 0.046(3) Uani 1 1 d . U . . .
H4 H 0.443818 0.854495 0.653338 0.055 Uiso 1 1 calc R U . . .
C12 C 0.6324(7) 0.4245(9) 0.61650(16) 0.046(3) Uani 1 1 d . U . . .
C3 C 0.5572(7) 0.7111(9) 0.69905(18) 0.043(3) Uani 1 1 d . U . . .
H3 H 0.554935 0.804025 0.745104 0.052 Uiso 1 1 calc R U . . .
C6 C 0.5666(7) 0.4647(9) 0.55930(16) 0.045(3) Uani 1 1 d . U . . .
C13 C 0.8313(9) 0.3232(10) 0.7939(2) 0.053(3) Uani 1 1 d . U . . .
C14 C 0.8215(6) 0.1684(8) 0.85969(15) 0.060(3) Uani 1 1 d . U . . .
H14 H 0.772359 0.073763 0.866402 0.072 Uiso 1 1 calc R U . . .
C16 C 0.9594(9) 0.2941(14) 0.9042(3) 0.078(4) Uani 1 1 d . U . . .
H16 H 1.003845 0.282183 0.941197 0.093 Uiso 1 1 calc R U . . .
C18 C 0.9034(9) 0.4667(12) 0.7834(3) 0.065(4) Uani 1 1 d . U . . .
H18 H 0.908539 0.573846 0.739455 0.078 Uiso 1 1 calc R U . . .
C17 C 0.9665(8) 0.4485(10) 0.8382(2) 0.073(4) Uani 1 1 d . U . . .
H17 H 1.015791 0.541642 0.831476 0.088 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
O2 C11 1.179(14) . ?
O1 C1 1.238(4) . ?
N1 C1 1.385(15) . ?
N1 C11 1.438(5) . ?
N1 C13 1.468(14) . ?
C10 C9 1.390(5) . ?
C10 C11 1.494(13) . ?
C10 C12 1.390(14) . ?
C7 C8 1.358(16) . ?
C7 C5 1.472(11) 3_666 ?
C7 C6 1.447(4) . ?
C1 C2 1.486(12) . ?
C8 H8 0.9300 . ?
C8 C9 1.410(12) . ?
C2 C12 1.432(5) . ?
C2 C3 1.329(13) . ?
C9 H9 0.9300 . ?
C5 C4 1.396(4) . ?
C5 C6 1.428(14) . ?
C15 H15 0.9300 . ?
C15 C14 1.392(14) . ?
C15 C16 1.35(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.408(11) . ?
C12 C6 1.414(11) . ?
C3 H3 0.9300 . ?
C13 C14 1.389(5) . ?
C13 C18 1.38(2) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.382(7) . ?
C18 H18 0.9300 . ?
C18 C17 1.346(15) . ?
C17 H17 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
C1 N1 C11 123.9(8) . . ?
C1 N1 C13 119.7(5) . . ?
C11 N1 C13 116.4(8) . . ?
C9 C10 C11 118.3(8) . . ?
C12 C10 C9 120.0(8) . . ?
C12 C10 C11 121.7(5) . . ?
C8 C7 C5 122.6(5) . 3_666 ?
C8 C7 C6 118.9(8) . . ?
C6 C7 C5 118.5(8) . 3_666 ?
O1 C1 N1 120.8(8) . . ?
O1 C1 C2 120.0(9) . . ?
N1 C1 C2 119.1(5) . . ?
C7 C8 H8 118.7 . . ?
C7 C8 C9 122.6(4) . . ?
C9 C8 H8 118.7 . . ?
C12 C2 C1 118.6(9) . . ?
C3 C2 C1 120.4(5) . . ?
C3 C2 C12 120.9(8) . . ?
C10 C9 C8 119.1(8) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C4 C5 C7 121.2(8) . 3_666 ?
C4 C5 C6 118.4(8) . . ?
C6 C5 C7 120.4(5) . 3_666 ?
O2 C11 N1 121.5(9) . . ?
O2 C11 C10 122.8(6) . . ?
N1 C11 C10 115.5(9) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C16 C15 C14 120.6(6) . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.9(7) . . ?
C3 C4 H4 120.1 . . ?
C10 C12 C2 121.0(8) . . ?
C10 C12 C6 121.2(5) . . ?
C6 C12 C2 117.7(8) . . ?
C2 C3 C4 122.1(4) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C6 C7 121.0(7) . . ?
C12 C6 C7 118.1(7) . . ?
C12 C6 C5 120.8(4) . . ?
C14 C13 N1 118.9(10) . . ?
C18 C13 N1 119.2(5) . . ?
C18 C13 C14 121.8(11) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 C15 117.5(9) . . ?
C13 C14 H14 121.2 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.1(12) . . ?
C17 C16 H16 119.9 . . ?
C13 C18 H18 120.7 . . ?
C17 C18 C13 118.6(7) . . ?
C17 C18 H18 120.7 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.3(12) . . ?
C18 C17 H17 119.4 . . ?

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
O1 C1 C2 C12 -179.6(5) . . . . ?
O1 C1 C2 C3 4.5(9) . . . . ?
N1 C1 C2 C12 -1.6(9) . . . . ?
N1 C1 C2 C3 -177.5(7) . . . . ?
N1 C13 C14 C15 -177.7(5) . . . . ?
N1 C13 C18 C17 178.7(5) . . . . ?
C10 C12 C6 C7 -1.6(8) . . . . ?
C10 C12 C6 C5 178.6(7) . . . . ?
C7 C8 C9 C10 0.9(9) . . . . ?
C7 C5 C4 C3 -180.0(5) 3_666 . . . ?
C7 C5 C6 C7 1.3(9) 3_666 . . . ?
C7 C5 C6 C12 -178.9(5) 3_666 . . . ?
C1 N1 C11 O2 -173.1(9) . . . . ?
C1 N1 C11 C10 1.7(10) . . . . ?
C1 N1 C13 C14 58.5(7) . . . . ?
C1 N1 C13 C18 -118.8(8) . . . . ?
C1 C2 C12 C10 2.3(9) . . . . ?
C1 C2 C12 C6 -179.9(5) . . . . ?
C1 C2 C3 C4 -178.8(5) . . . . ?
C8 C7 C6 C5 179.9(8) . . . . ?
C8 C7 C6 C12 0.1(8) . . . . ?
C2 C12 C6 C7 -179.4(5) . . . . ?
C2 C12 C6 C5 0.8(8) . . . . ?
C9 C10 C11 O2 -7.7(12) . . . . ?
C9 C10 C11 N1 177.5(6) . . . . ?
C9 C10 C12 C2 -179.5(5) . . . . ?
C9 C10 C12 C6 2.8(9) . . . . ?
C5 C7 C8 C9 -178.5(5) 3_666 . . . ?
C5 C7 C6 C5 -1.3(9) 3_666 . . . ?
C5 C7 C6 C12 178.9(5) 3_666 . . . ?
C5 C4 C3 C2 -3.3(9) . . . . ?
C11 N1 C1 O1 177.5(5) . . . . ?
C11 N1 C1 C2 -0.4(10) . . . . ?
C11 N1 C13 C14 -124.3(6) . . . . ?
C11 N1 C13 C18 58.5(8) . . . . ?
C11 C10 C9 C8 179.0(5) . . . . ?
C11 C10 C12 C2 -1.0(10) . . . . ?
C11 C10 C12 C6 -178.7(5) . . . . ?
C15 C16 C17 C18 -0.6(11) . . . . ?
C4 C5 C6 C7 -178.7(4) . . . . ?
C4 C5 C6 C12 1.1(9) . . . . ?
C12 C10 C9 C8 -2.4(9) . . . . ?
C12 C10 C11 O2 173.8(9) . . . . ?
C12 C10 C11 N1 -1.0(9) . . . . ?
C12 C2 C3 C4 5.3(10) . . . . ?
C3 C2 C12 C10 178.2(7) . . . . ?
C3 C2 C12 C6 -4.0(9) . . . . ?
C6 C7 C8 C9 0.3(10) . . . . ?
C6 C5 C4 C3 0.0(8) . . . . ?
C13 N1 C1 O1 -5.4(10) . . . . ?
C13 N1 C1 C2 176.6(5) . . . . ?
C13 N1 C11 O2 9.7(12) . . . . ?
C13 N1 C11 C10 -175.4(6) . . . . ?
C13 C18 C17 C16 -0.9(10) . . . . ?
C14 C15 C16 C17 1.7(13) . . . . ?
C14 C13 C18 C17 1.5(11) . . . . ?
C16 C15 C14 C13 -1.1(11) . . . . ?
C18 C13 C14 C15 -0.5(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_PTCDI_Ph_0_78GPa
_database_code_depnum_ccdc_archive 'CCDC 2253186'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PTCDI_Ph_0_78GPa    
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.393 Why?  
RESPONSE: These data come from high-pressure experiment and part of the 
reflection cannot be collected, due to the DAC opening angle, and the 
measurement strategy. 
;
_vrf_PLAT088_PTCDI_Ph_0_78GPa    
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.84 Note  
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC
chamber.
;
_vrf_PLAT340_PTCDI_Ph_0_78GPa    
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.0113 Ang.  
RESPONSE: These data come from high-pressure experiment and part of the 
reflection cannot be collected, affecting bond precision. In addition, 
despite multiple attempts to grow better diffracting crystals, it was not 
successful.
;
_vrf_PLAT911_PTCDI_Ph_0_78GPa    
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        937 Report
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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 -0.0011 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0016 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0014 0.0018 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.812(17)
_cell_length_b                   3.7391(5)
_cell_length_c                   18.054(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.49(5)
_cell_angle_gamma                90
_cell_volume                     1122.5(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    276
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.6200
_cell_measurement_theta_min      2.6170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.044
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 0.393
_diffrn_reflns_Laue_measured_fraction_max 0.229
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            2604
_diffrn_reflns_point_group_measured_fraction_full 0.393
_diffrn_reflns_point_group_measured_fraction_max 0.229
_diffrn_reflns_theta_full        14.237
_diffrn_reflns_theta_max         21.244
_diffrn_reflns_theta_min         2.622
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_detector_type            'Eiger 9M CdTe'
_diffrn_measured_fraction_theta_full 0.393
_diffrn_measured_fraction_theta_max 0.229
_diffrn_measurement_details      
;
 Data were collected at room temperature and pressure of 0.78(2) GPa
 Pressure was determined by monitoring the shift of 
 the ruby R1-fluorescence line.
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_suport 'diamond anvil cell'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0239101000
_diffrn_orient_matrix_UB_12      -0.0229379000
_diffrn_orient_matrix_UB_13      -0.0067053000
_diffrn_orient_matrix_UB_21      0.0057784000
_diffrn_orient_matrix_UB_22      -0.0527423000
_diffrn_orient_matrix_UB_23      -0.0183528000
_diffrn_orient_matrix_UB_31      0.0026019000
_diffrn_orient_matrix_UB_32      -0.0930575000
_diffrn_orient_matrix_UB_33      0.0120074000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.40989
_diffrn_source                   'undulator, ID15B, ESRF'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                667
_reflns_number_total             1490
_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 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1490
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0667
_refine_ls_restrained_S_all      0.871
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1477P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1927
_refine_ls_wR_factor_ref         0.2408
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C18, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Rigid body (RIGU) restrains
 C18, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, C1, C2, C11, C10, C9, C8, C7, C6, C12, C5, C4, C3, O1, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C14(H14), C8(H8), C18(H18), C3(H3), C15(H15), C9(H9), C17(H17),
 C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.6870(4) 0.6308(8) 0.81424(16) 0.062(3) Uani 1 1 d . . . . .
O2 O 0.8343(5) 0.0674(10) 0.6558(2) 0.071(3) Uani 1 1 d . . . . .
C6 C 0.5686(6) 0.4708(10) 0.5590(2) 0.055(3) Uani 1 1 d . . . . .
N1 N 0.7644(5) 0.3628(9) 0.7365(2) 0.058(3) Uani 1 1 d . . . . .
C7 C 0.5743(6) 0.3456(10) 0.4849(2) 0.055(3) Uani 1 1 d . . . . .
C4 C 0.4925(6) 0.7600(10) 0.6464(2) 0.052(3) Uani 1 1 d . . . . .
H4 H 0.446374 0.872782 0.657506 0.063 Uiso 1 1 calc R U . . .
C14 C 0.8255(7) 0.1848(11) 0.8650(3) 0.060(3) Uani 1 1 d . U . . .
H14 H 0.776393 0.090130 0.873086 0.072 Uiso 1 1 calc R U . . .
C1 C 0.6923(6) 0.5258(10) 0.7509(2) 0.051(3) Uani 1 1 d . . . . .
C10 C 0.7067(6) 0.2802(10) 0.6037(2) 0.055(3) Uani 1 1 d . . . . .
C2 C 0.6276(6) 0.5661(10) 0.6900(2) 0.052(3) Uani 1 1 d . . . . .
C8 C 0.6489(7) 0.2002(11) 0.4743(3) 0.059(3) Uani 1 1 d . . . . .
H8 H 0.655387 0.122036 0.426667 0.071 Uiso 1 1 calc R U . . .
C5 C 0.4924(6) 0.6288(10) 0.5730(2) 0.055(3) Uani 1 1 d . . . . .
C13 C 0.8336(7) 0.3401(11) 0.7958(3) 0.055(3) Uani 1 1 d . U . . .
C12 C 0.6324(6) 0.4393(10) 0.6158(2) 0.054(3) Uani 1 1 d . . . . .
C18 C 0.9054(8) 0.4780(12) 0.7840(3) 0.061(3) Uani 1 1 d . U . . .
H18 H 0.910431 0.585370 0.738413 0.073 Uiso 1 1 calc R U . . .
C3 C 0.5569(6) 0.7295(10) 0.7017(2) 0.054(3) Uani 1 1 d . . . . .
H3 H 0.552937 0.821681 0.748909 0.065 Uiso 1 1 calc R U . . .
C11 C 0.7726(7) 0.2281(12) 0.6641(3) 0.058(3) Uani 1 1 d . . . . .
C15 C 0.8895(8) 0.1732(13) 0.9199(3) 0.066(3) Uani 1 1 d . U . . .
H15 H 0.883546 0.073817 0.965991 0.079 Uiso 1 1 calc R U . . .
C9 C 0.7129(7) 0.1678(11) 0.5311(3) 0.059(3) Uani 1 1 d . . . . .
H9 H 0.760985 0.069639 0.520945 0.071 Uiso 1 1 calc R U . . .
C17 C 0.9717(9) 0.4580(13) 0.8402(3) 0.068(3) Uani 1 1 d . U . . .
H17 H 1.021237 0.546297 0.831782 0.081 Uiso 1 1 calc R U . . .
C16 C 0.9636(8) 0.3067(14) 0.9088(4) 0.073(3) Uani 1 1 d . U . . .
H16 H 1.007339 0.294950 0.946809 0.088 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
O1 C1 1.224(4) . ?
O2 C11 1.227(12) . ?
C6 C7 1.434(4) . ?
C6 C5 1.467(13) . ?
C6 C12 1.375(14) . ?
N1 C1 1.415(12) . ?
N1 C13 1.464(14) . ?
N1 C11 1.426(5) . ?
C7 C8 1.406(13) . ?
C7 C5 1.419(13) 3_666 ?
C4 H4 0.9300 . ?
C4 C5 1.412(5) . ?
C4 C3 1.366(14) . ?
C14 H14 0.9300 . ?
C14 C13 1.402(5) . ?
C14 C15 1.350(17) . ?
C1 C2 1.437(14) . ?
C10 C12 1.429(13) . ?
C10 C11 1.449(15) . ?
C10 C9 1.395(5) . ?
C2 C12 1.434(5) . ?
C2 C3 1.381(12) . ?
C8 H8 0.9300 . ?
C8 C9 1.378(15) . ?
C13 C18 1.359(16) . ?
C18 H18 0.9300 . ?
C18 C17 1.394(18) . ?
C3 H3 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.384(17) . ?
C9 H9 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.386(7) . ?
C16 H16 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 C6 C5 118.3(8) . . ?
C12 C6 C7 121.1(8) . . ?
C12 C6 C5 120.7(4) . . ?
C1 N1 C13 120.0(4) . . ?
C1 N1 C11 121.5(8) . . ?
C11 N1 C13 118.4(8) . . ?
C8 C7 C6 115.9(8) . . ?
C8 C7 C5 123.4(4) . 3_666 ?
C5 C7 C6 120.7(8) 3_666 . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
C3 C4 C5 123.3(7) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C15 C14 C13 119.7(9) . . ?
O1 C1 N1 119.6(8) . . ?
O1 C1 C2 122.0(8) . . ?
N1 C1 C2 118.4(4) . . ?
C12 C10 C11 122.0(4) . . ?
C9 C10 C12 117.3(9) . . ?
C9 C10 C11 120.7(8) . . ?
C12 C2 C1 122.7(8) . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 C12 117.2(8) . . ?
C7 C8 H8 118.4 . . ?
C9 C8 C7 123.2(4) . . ?
C9 C8 H8 118.4 . . ?
C7 C5 C6 121.0(3) 3_666 . ?
C4 C5 C6 115.0(8) . . ?
C4 C5 C7 124.0(7) . 3_666 ?
C14 C13 N1 120.3(9) . . ?
C18 C13 N1 119.5(5) . . ?
C18 C13 C14 120.2(10) . . ?
C6 C12 C10 121.6(4) . . ?
C6 C12 C2 121.6(8) . . ?
C10 C12 C2 116.8(8) . . ?
C13 C18 H18 120.1 . . ?
C13 C18 C17 119.8(5) . . ?
C17 C18 H18 120.1 . . ?
C4 C3 C2 122.1(4) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
O2 C11 N1 118.9(9) . . ?
O2 C11 C10 122.8(4) . . ?
N1 C11 C10 118.4(8) . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.2(5) . . ?
C16 C15 H15 119.4 . . ?
C10 C9 H9 119.6 . . ?
C8 C9 C10 120.9(8) . . ?
C8 C9 H9 119.6 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 120.0(11) . . ?
C16 C17 H17 120.0 . . ?
C15 C16 C17 119.0(11) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 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
O1 C1 C2 C12 -178.9(4) . . . . ?
O1 C1 C2 C3 0.4(7) . . . . ?
C6 C7 C8 C9 1.7(7) . . . . ?
N1 C1 C2 C12 1.8(7) . . . . ?
N1 C1 C2 C3 -178.9(4) . . . . ?
N1 C13 C18 C17 179.9(4) . . . . ?
C7 C6 C5 C7 0.6(7) . . . 3_666 ?
C7 C6 C5 C4 -177.3(4) . . . . ?
C7 C6 C12 C10 -0.2(7) . . . . ?
C7 C6 C12 C2 179.5(4) . . . . ?
C7 C8 C9 C10 0.1(8) . . . . ?
C14 C13 C18 C17 1.3(7) . . . . ?
C14 C15 C16 C17 0.7(8) . . . . ?
C1 N1 C13 C14 54.2(5) . . . . ?
C1 N1 C13 C18 -124.3(5) . . . . ?
C1 N1 C11 O2 -175.0(5) . . . . ?
C1 N1 C11 C10 3.6(7) . . . . ?
C1 C2 C12 C6 177.8(5) . . . . ?
C1 C2 C12 C10 -2.4(7) . . . . ?
C1 C2 C3 C4 -177.1(5) . . . . ?
C5 C6 C7 C8 179.3(4) . . . . ?
C5 C6 C7 C5 -0.6(7) . . . 3_666 ?
C5 C6 C12 C10 178.8(4) . . . . ?
C5 C6 C12 C2 -1.5(7) . . . . ?
C5 C7 C8 C9 -178.4(5) 3_666 . . . ?
C5 C4 C3 C2 0.0(7) . . . . ?
C13 N1 C1 O1 -3.7(7) . . . . ?
C13 N1 C1 C2 175.6(4) . . . . ?
C13 N1 C11 O2 7.0(8) . . . . ?
C13 N1 C11 C10 -174.4(5) . . . . ?
C13 C14 C15 C16 -1.1(8) . . . . ?
C13 C18 C17 C16 -1.8(7) . . . . ?
C12 C6 C7 C8 -1.6(7) . . . . ?
C12 C6 C7 C5 178.5(4) . . . 3_666 ?
C12 C6 C5 C7 -178.5(4) . . . 3_666 ?
C12 C6 C5 C4 3.6(6) . . . . ?
C12 C10 C11 O2 174.2(5) . . . . ?
C12 C10 C11 N1 -4.3(8) . . . . ?
C12 C10 C9 C8 -1.9(7) . . . . ?
C12 C2 C3 C4 2.3(7) . . . . ?
C18 C17 C16 C15 0.7(7) . . . . ?
C3 C4 C5 C6 -2.9(6) . . . . ?
C3 C4 C5 C7 179.2(5) . . . 3_666 ?
C3 C2 C12 C6 -1.5(7) . . . . ?
C3 C2 C12 C10 178.2(4) . . . . ?
C11 N1 C1 O1 178.3(4) . . . . ?
C11 N1 C1 C2 -2.3(7) . . . . ?
C11 N1 C13 C14 -127.8(5) . . . . ?
C11 N1 C13 C18 53.7(6) . . . . ?
C11 C10 C12 C6 -176.5(5) . . . . ?
C11 C10 C12 C2 3.7(7) . . . . ?
C11 C10 C9 C8 176.7(5) . . . . ?
C15 C14 C13 N1 -178.4(5) . . . . ?
C15 C14 C13 C18 0.1(7) . . . . ?
C9 C10 C12 C6 2.0(7) . . . . ?
C9 C10 C12 C2 -177.7(4) . . . . ?
C9 C10 C11 O2 -4.3(9) . . . . ?
C9 C10 C11 N1 177.2(4) . . . . ?

_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
;
####################################################################### 
# 
# 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_PTCDI_Ph_0_495GPa
_database_code_depnum_ccdc_archive 'CCDC 2253185'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PTCDI_Ph_0_495GPa   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.396 Why?  
RESPONSE: These data come from high-pressure experiment and part of the 
reflection cannot be collected, due to the DAC opening angle and the 
measurement strategy.  
;
_vrf_PLAT026_PTCDI_Ph_0_495GPa   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        38% Check  
RESPONSE: This low value is due to the overall poor diffraction quality of the 
crystal.
;
_vrf_PLAT149_PTCDI_Ph_0_495GPa   
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.06 Degree
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT911_PTCDI_Ph_0_495GPa   
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        949 Report
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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 -0.0011 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0016 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0014 0.0018 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.77(2)
_cell_length_b                   3.7945(5)
_cell_length_c                   18.152(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.56(6)
_cell_angle_gamma                90
_cell_volume                     1142.2(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    248
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.8560
_cell_measurement_theta_min      2.6080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.043
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.396
_diffrn_reflns_Laue_measured_fraction_max 0.238
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            2652
_diffrn_reflns_point_group_measured_fraction_full 0.396
_diffrn_reflns_point_group_measured_fraction_max 0.238
_diffrn_reflns_theta_full        14.237
_diffrn_reflns_theta_max         20.976
_diffrn_reflns_theta_min         2.608
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_detector_type            'Eiger 9M CdTe'
_diffrn_measured_fraction_theta_full 0.396
_diffrn_measured_fraction_theta_max 0.238
_diffrn_measurement_details      
;
 Data were collected at room temperature and pressure of 0.49(2) GPa
 Pressure was determined by monitoring the shift of 
 the ruby R1-fluorescence line.
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_suport 'diamond anvil cell'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.40989
_diffrn_source                   'undulator, ID15B, ESRF'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                581
_reflns_number_total             1522
_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 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1522
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      0.834
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1267
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C18, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Rigid body (RIGU) restrains
 C17, C18, C13, C14, C15, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, C11, C10, C12, C6, C5, C4, C3, C2, C9, C8, C7, O1, C1, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C15(H15), C4(H4), C3(H3), C14(H14), C16(H16), C18(H18),
 C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8325(3) 0.0634(7) 0.65581(14) 0.059(3) Uani 1 1 d . . . . .
O1 O 0.6869(3) 0.6261(5) 0.81370(11) 0.049(2) Uani 1 1 d . . . . .
N1 N 0.7646(4) 0.3589(7) 0.73643(17) 0.049(3) Uani 1 1 d . . . . .
C10 C 0.7069(5) 0.2767(8) 0.60426(19) 0.044(2) Uani 1 1 d . . . . .
C7 C 0.5735(4) 0.3431(7) 0.48507(17) 0.044(3) Uani 1 1 d . . . . .
C1 C 0.6924(5) 0.5217(8) 0.7503(2) 0.042(2) Uani 1 1 d . . . . .
C8 C 0.6492(5) 0.1994(8) 0.4755(2) 0.049(2) Uani 1 1 d . . . . .
H8 H 0.656551 0.126155 0.428094 0.059 Uiso 1 1 calc R U . . .
C2 C 0.6274(5) 0.5628(8) 0.68931(19) 0.042(2) Uani 1 1 d . . . . .
C9 C 0.7116(5) 0.1631(8) 0.53200(19) 0.049(3) Uani 1 1 d . . . . .
H9 H 0.759059 0.058894 0.522120 0.059 Uiso 1 1 calc R U . . .
C5 C 0.4923(5) 0.6276(7) 0.57295(19) 0.043(2) Uani 1 1 d . . . . .
C11 C 0.7732(5) 0.2242(9) 0.6649(2) 0.048(2) Uani 1 1 d . . . . .
C15 C 0.8891(6) 0.1708(10) 0.9190(2) 0.065(3) Uani 1 1 d . U . . .
H15 H 0.883333 0.074018 0.964936 0.078 Uiso 1 1 calc R U . . .
C4 C 0.4920(4) 0.7560(8) 0.64575(18) 0.044(2) Uani 1 1 d . . . . .
H4 H 0.445913 0.868040 0.656736 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6318(4) 0.4364(8) 0.61601(18) 0.043(2) Uani 1 1 d . . . . .
C3 C 0.5568(5) 0.7231(8) 0.70111(19) 0.045(2) Uani 1 1 d . . . . .
H3 H 0.552895 0.811964 0.748184 0.054 Uiso 1 1 calc R U . . .
C6 C 0.5688(5) 0.4696(7) 0.55939(18) 0.043(2) Uani 1 1 d . . . . .
C13 C 0.8326(6) 0.3376(8) 0.7954(2) 0.048(3) Uani 1 1 d . U . . .
C14 C 0.8240(5) 0.1799(8) 0.86342(19) 0.056(3) Uani 1 1 d . U . . .
H14 H 0.774904 0.082820 0.870880 0.067 Uiso 1 1 calc R U . . .
C16 C 0.9632(6) 0.3032(10) 0.9078(3) 0.068(3) Uani 1 1 d . U . . .
H16 H 1.007594 0.290125 0.945063 0.082 Uiso 1 1 calc R U . . .
C18 C 0.9066(7) 0.4748(10) 0.7840(3) 0.055(3) Uani 1 1 d . U . . .
H18 H 0.912587 0.578337 0.738734 0.067 Uiso 1 1 calc R U . . .
C17 C 0.9696(6) 0.4562(10) 0.8393(2) 0.062(3) Uani 1 1 d . U . . .
H17 H 1.018967 0.548685 0.831478 0.074 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
O2 C11 1.200(8) . ?
O1 C1 1.234(3) . ?
N1 C1 1.414(9) . ?
N1 C11 1.422(4) . ?
N1 C13 1.446(12) . ?
C10 C9 1.394(4) . ?
C10 C11 1.457(11) . ?
C10 C12 1.441(9) . ?
C7 C8 1.416(10) . ?
C7 C5 1.411(10) 3_666 ?
C7 C6 1.445(3) . ?
C1 C2 1.441(11) . ?
C8 H8 0.9300 . ?
C8 C9 1.359(11) . ?
C2 C12 1.427(4) . ?
C2 C3 1.376(10) . ?
C9 H9 0.9300 . ?
C5 C4 1.409(4) . ?
C5 C6 1.470(10) . ?
C15 H15 0.9300 . ?
C15 C14 1.372(13) . ?
C15 C16 1.383(13) . ?
C4 H4 0.9300 . ?
C4 C3 1.371(10) . ?
C12 C6 1.366(10) . ?
C3 H3 0.9300 . ?
C13 C14 1.398(4) . ?
C13 C18 1.390(13) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.390(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.346(14) . ?
C17 H17 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
C1 N1 C11 121.6(6) . . ?
C1 N1 C13 119.7(3) . . ?
C11 N1 C13 118.7(6) . . ?
C9 C10 C11 121.7(6) . . ?
C9 C10 C12 116.3(6) . . ?
C12 C10 C11 122.0(3) . . ?
C8 C7 C6 114.6(6) . . ?
C5 C7 C8 123.6(3) 3_666 . ?
C5 C7 C6 121.7(6) 3_666 . ?
O1 C1 N1 119.4(6) . . ?
O1 C1 C2 121.9(6) . . ?
N1 C1 C2 118.7(3) . . ?
C7 C8 H8 118.3 . . ?
C9 C8 C7 123.4(3) . . ?
C9 C8 H8 118.3 . . ?
C12 C2 C1 122.7(6) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 C12 117.4(6) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 C10 122.2(6) . . ?
C8 C9 H9 118.9 . . ?
C7 C5 C6 120.8(3) 3_666 . ?
C4 C5 C7 124.2(5) . 3_666 ?
C4 C5 C6 115.0(6) . . ?
O2 C11 N1 120.5(7) . . ?
O2 C11 C10 121.4(3) . . ?
N1 C11 C10 118.1(6) . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.2(4) . . ?
C16 C15 H15 119.4 . . ?
C5 C4 H4 118.6 . . ?
C3 C4 C5 122.9(5) . . ?
C3 C4 H4 118.6 . . ?
C2 C12 C10 116.6(6) . . ?
C6 C12 C10 121.5(3) . . ?
C6 C12 C2 121.9(6) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.2(3) . . ?
C4 C3 H3 118.9 . . ?
C7 C6 C5 117.5(6) . . ?
C12 C6 C7 121.9(6) . . ?
C12 C6 C5 120.6(3) . . ?
C14 C13 N1 120.2(7) . . ?
C18 C13 N1 119.5(4) . . ?
C18 C13 C14 120.3(8) . . ?
C15 C14 C13 118.9(7) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C17 118.3(8) . . ?
C17 C16 H16 120.9 . . ?
C13 C18 H18 120.4 . . ?
C17 C18 C13 119.2(4) . . ?
C17 C18 H18 120.4 . . ?
C16 C17 H17 118.9 . . ?
C18 C17 C16 122.2(8) . . ?
C18 C17 H17 118.9 . . ?

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
O1 C1 C2 C12 -178.4(3) . . . . ?
O1 C1 C2 C3 0.1(6) . . . . ?
N1 C1 C2 C12 2.0(6) . . . . ?
N1 C1 C2 C3 -179.4(3) . . . . ?
N1 C13 C14 C15 -178.5(4) . . . . ?
N1 C13 C18 C17 179.6(4) . . . . ?
C10 C12 C6 C7 0.8(6) . . . . ?
C10 C12 C6 C5 178.9(3) . . . . ?
C7 C8 C9 C10 -2.2(7) . . . . ?
C7 C5 C4 C3 179.8(4) 3_666 . . . ?
C7 C5 C6 C7 -0.7(5) 3_666 . . . ?
C7 C5 C6 C12 -178.9(4) 3_666 . . . ?
C1 N1 C11 O2 -174.3(4) . . . . ?
C1 N1 C11 C10 3.6(6) . . . . ?
C1 N1 C13 C14 55.7(4) . . . . ?
C1 N1 C13 C18 -124.3(5) . . . . ?
C1 C2 C12 C10 -2.8(5) . . . . ?
C1 C2 C12 C6 178.3(4) . . . . ?
C1 C2 C3 C4 -177.3(4) . . . . ?
C8 C7 C6 C5 179.0(3) . . . . ?
C8 C7 C6 C12 -2.8(5) . . . . ?
C2 C12 C6 C7 179.7(3) . . . . ?
C2 C12 C6 C5 -2.2(6) . . . . ?
C9 C10 C11 O2 -4.3(7) . . . . ?
C9 C10 C11 N1 177.9(3) . . . . ?
C9 C10 C12 C2 -178.2(3) . . . . ?
C9 C10 C12 C6 0.8(5) . . . . ?
C5 C7 C8 C9 -178.2(4) 3_666 . . . ?
C5 C7 C6 C5 0.7(6) 3_666 . . . ?
C5 C7 C6 C12 178.9(4) 3_666 . . . ?
C5 C4 C3 C2 0.4(6) . . . . ?
C11 N1 C1 O1 178.0(3) . . . . ?
C11 N1 C1 C2 -2.4(5) . . . . ?
C11 N1 C13 C14 -126.2(4) . . . . ?
C11 N1 C13 C18 53.7(5) . . . . ?
C11 C10 C9 C8 177.7(4) . . . . ?
C11 C10 C12 C2 4.1(5) . . . . ?
C11 C10 C12 C6 -177.0(4) . . . . ?
C15 C16 C17 C18 -0.8(6) . . . . ?
C4 C5 C6 C7 -178.1(3) . . . . ?
C4 C5 C6 C12 3.7(5) . . . . ?
C12 C10 C9 C8 -0.1(6) . . . . ?
C12 C10 C11 O2 173.3(4) . . . . ?
C12 C10 C11 N1 -4.5(6) . . . . ?
C12 C2 C3 C4 1.3(6) . . . . ?
C3 C2 C12 C10 178.6(3) . . . . ?
C3 C2 C12 C6 -0.3(5) . . . . ?
C6 C7 C8 C9 3.6(5) . . . . ?
C6 C5 C4 C3 -2.8(5) . . . . ?
C13 N1 C1 O1 -4.0(5) . . . . ?
C13 N1 C1 C2 175.6(4) . . . . ?
C13 N1 C11 O2 7.7(6) . . . . ?
C13 N1 C11 C10 -174.4(4) . . . . ?
C13 C18 C17 C16 0.1(7) . . . . ?
C14 C15 C16 C17 1.9(6) . . . . ?
C14 C13 C18 C17 -0.4(6) . . . . ?
C16 C15 C14 C13 -2.3(6) . . . . ?
C18 C13 C14 C15 1.5(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
;
####################################################################### 
# 
# 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_PTCDI_Ph_1_10GPa
_database_code_depnum_ccdc_archive 'CCDC 2253187'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PTCDI_Ph_1_10GPa    
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.393 Why?  
RESPONSE: These data come from high-pressure experiment and part of the 
reflection cannot be collected, due to the DAC opening angle and the 
measurement strategy.  
;
_vrf_PLAT088_PTCDI_Ph_1_10GPa    
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.67 Note  
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber.
;
_vrf_PLAT911_PTCDI_Ph_1_10GPa    
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        922 Report	
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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 -0.0011 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0016 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0014 0.0018 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.759(15)
_cell_length_b                   3.6939(4)
_cell_length_c                   17.998(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.49(4)
_cell_angle_gamma                90
_cell_volume                     1102.0(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    243
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.8180
_cell_measurement_theta_min      2.6370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.045
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.393
_diffrn_reflns_Laue_measured_fraction_max 0.228
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            2540
_diffrn_reflns_point_group_measured_fraction_full 0.393
_diffrn_reflns_point_group_measured_fraction_max 0.228
_diffrn_reflns_theta_full        14.237
_diffrn_reflns_theta_max         21.238
_diffrn_reflns_theta_min         2.630
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_detector_type            'Eiger 9M CdTe'
_diffrn_measured_fraction_theta_full 0.393
_diffrn_measured_fraction_theta_max 0.228
_diffrn_measurement_details      
;
 Data were collected at room temperature and pressure of 1.10(2) GPa
 Pressure was determined by monitoring the shift of 
 the ruby R1-fluorescence line.
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  synchrotron
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_suport 'diamond anvil cell'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.40989
_diffrn_source                   'undulator, ID15B, ESRF'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                764
_reflns_number_total             1458
_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 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1458
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      0.931
_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)+(0.0835P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1574
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C18, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Rigid body (RIGU) restrains
 C18, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, C11, C10, C9, C8, C7, C6, C12, C5, C4, C3, C2, C1, O1, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C14(H14), C8(H8), C18(H18), C3(H3), C15(H15), C9(H9), C17(H17),
 C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.6875(3) 0.6374(6) 0.81483(12) 0.043(2) Uani 1 1 d . . . . .
O2 O 0.8350(4) 0.0691(7) 0.65520(15) 0.053(2) Uani 1 1 d . . . . .
C6 C 0.5685(4) 0.4744(6) 0.55895(17) 0.0319(19) Uani 1 1 d . . . . .
N1 N 0.7660(4) 0.3674(7) 0.73693(15) 0.037(2) Uani 1 1 d . . . . .
C7 C 0.5748(4) 0.3445(7) 0.48458(17) 0.036(2) Uani 1 1 d . . . . .
C4 C 0.4920(4) 0.7643(7) 0.64657(16) 0.034(2) Uani 1 1 d . . . . .
H4 H 0.445541 0.876965 0.657659 0.041 Uiso 1 1 calc R U . . .
C14 C 0.8258(5) 0.1892(8) 0.86573(19) 0.044(2) Uani 1 1 d . U . . .
H14 H 0.776330 0.095442 0.874026 0.052 Uiso 1 1 calc R U . . .
C1 C 0.6930(4) 0.5308(7) 0.75112(18) 0.035(2) Uani 1 1 d . . . . .
C10 C 0.7079(4) 0.2856(7) 0.60361(18) 0.0338(19) Uani 1 1 d . . . . .
C2 C 0.6281(4) 0.5710(7) 0.69001(18) 0.0344(19) Uani 1 1 d . . . . .
C8 C 0.6504(5) 0.2033(8) 0.47371(19) 0.041(2) Uani 1 1 d . . . . .
H8 H 0.657538 0.128606 0.425787 0.049 Uiso 1 1 calc R U . . .
C5 C 0.4921(4) 0.6296(7) 0.57333(17) 0.035(2) Uani 1 1 d . . . . .
C13 C 0.8335(5) 0.3434(8) 0.7963(2) 0.034(2) Uani 1 1 d . U . . .
C12 C 0.6329(4) 0.4446(7) 0.61593(17) 0.0330(19) Uani 1 1 d . . . . .
C18 C 0.9082(5) 0.4806(8) 0.7847(2) 0.039(2) Uani 1 1 d . U . . .
H18 H 0.914113 0.586389 0.738940 0.047 Uiso 1 1 calc R U . . .
C3 C 0.5568(4) 0.7374(7) 0.70208(18) 0.036(2) Uani 1 1 d . . . . .
H3 H 0.553099 0.833271 0.749233 0.043 Uiso 1 1 calc R U . . .
C11 C 0.7744(5) 0.2321(8) 0.66426(19) 0.036(2) Uani 1 1 d . . . . .
C15 C 0.8899(6) 0.1759(9) 0.9210(2) 0.051(2) Uani 1 1 d . U . . .
H15 H 0.883949 0.077334 0.967382 0.061 Uiso 1 1 calc R U . . .
C9 C 0.7135(5) 0.1717(8) 0.53067(18) 0.039(2) Uani 1 1 d . . . . .
H9 H 0.761627 0.071189 0.520560 0.046 Uiso 1 1 calc R U . . .
C17 C 0.9721(6) 0.4597(9) 0.8403(2) 0.047(2) Uani 1 1 d . U . . .
H17 H 1.021928 0.548858 0.832015 0.056 Uiso 1 1 calc R U . . .
C16 C 0.9643(6) 0.3074(9) 0.9092(2) 0.052(3) Uani 1 1 d . U . . .
H16 H 1.008495 0.293761 0.946996 0.062 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
O1 C1 1.229(3) . ?
O2 C11 1.212(8) . ?
C6 C7 1.440(3) . ?
C6 C5 1.460(9) . ?
C6 C12 1.379(9) . ?
N1 C1 1.420(9) . ?
N1 C13 1.440(10) . ?
N1 C11 1.427(3) . ?
C7 C8 1.410(9) . ?
C7 C5 1.417(9) 3_666 ?
C4 H4 0.9300 . ?
C4 C5 1.409(3) . ?
C4 C3 1.367(9) . ?
C14 H14 0.9300 . ?
C14 C13 1.397(4) . ?
C14 C15 1.354(12) . ?
C1 C2 1.437(10) . ?
C10 C12 1.434(9) . ?
C10 C11 1.454(10) . ?
C10 C9 1.395(3) . ?
C2 C12 1.426(3) . ?
C2 C3 1.388(9) . ?
C8 H8 0.9300 . ?
C8 C9 1.365(10) . ?
C13 C18 1.394(11) . ?
C18 H18 0.9300 . ?
C18 C17 1.356(12) . ?
C3 H3 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.383(12) . ?
C9 H9 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.386(5) . ?
C16 H16 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 C6 C5 118.8(6) . . ?
C12 C6 C7 120.5(5) . . ?
C12 C6 C5 120.7(2) . . ?
C1 N1 C13 119.7(3) . . ?
C1 N1 C11 121.2(6) . . ?
C11 N1 C13 119.0(5) . . ?
C8 C7 C6 116.3(6) . . ?
C8 C7 C5 123.5(3) . 3_666 ?
C5 C7 C6 120.2(5) 3_666 . ?
C5 C4 H4 118.4 . . ?
C3 C4 H4 118.4 . . ?
C3 C4 C5 123.2(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C15 C14 C13 120.2(7) . . ?
O1 C1 N1 119.3(6) . . ?
O1 C1 C2 121.9(5) . . ?
N1 C1 C2 118.8(3) . . ?
C12 C10 C11 122.1(3) . . ?
C9 C10 C12 116.8(6) . . ?
C9 C10 C11 121.0(6) . . ?
C12 C2 C1 122.7(5) . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 C12 117.4(5) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 C7 122.7(3) . . ?
C9 C8 H8 118.7 . . ?
C7 C5 C6 121.0(3) 3_666 . ?
C4 C5 C6 115.3(5) . . ?
C4 C5 C7 123.6(5) . 3_666 ?
C14 C13 N1 121.5(6) . . ?
C18 C13 N1 119.4(3) . . ?
C18 C13 C14 119.1(7) . . ?
C6 C12 C10 121.7(3) . . ?
C6 C12 C2 121.5(5) . . ?
C2 C12 C10 116.8(6) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 C13 119.9(4) . . ?
C17 C18 H18 120.1 . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
O2 C11 N1 119.7(6) . . ?
O2 C11 C10 122.1(3) . . ?
N1 C11 C10 118.2(5) . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.7(4) . . ?
C16 C15 H15 119.6 . . ?
C10 C9 H9 119.0 . . ?
C8 C9 C10 121.9(6) . . ?
C8 C9 H9 119.0 . . ?
C18 C17 H17 119.5 . . ?
C18 C17 C16 121.0(8) . . ?
C16 C17 H17 119.5 . . ?
C15 C16 C17 119.1(7) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 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
O1 C1 C2 C12 -179.1(3) . . . . ?
O1 C1 C2 C3 0.6(5) . . . . ?
C6 C7 C8 C9 3.3(5) . . . . ?
N1 C1 C2 C12 1.7(5) . . . . ?
N1 C1 C2 C3 -178.5(3) . . . . ?
N1 C13 C18 C17 179.9(3) . . . . ?
C7 C6 C5 C7 -0.4(5) . . . 3_666 ?
C7 C6 C5 C4 -177.4(2) . . . . ?
C7 C6 C12 C10 0.1(5) . . . . ?
C7 C6 C12 C2 -179.9(3) . . . . ?
C7 C8 C9 C10 -1.5(6) . . . . ?
C14 C13 C18 C17 0.7(5) . . . . ?
C14 C15 C16 C17 1.2(5) . . . . ?
C1 N1 C13 C14 53.2(4) . . . . ?
C1 N1 C13 C18 -126.0(4) . . . . ?
C1 N1 C11 O2 -174.3(3) . . . . ?
C1 N1 C11 C10 3.7(5) . . . . ?
C1 C2 C12 C6 177.5(3) . . . . ?
C1 C2 C12 C10 -2.6(5) . . . . ?
C1 C2 C3 C4 -176.5(3) . . . . ?
C5 C6 C7 C8 178.9(3) . . . . ?
C5 C6 C7 C5 0.4(5) . . . 3_666 ?
C5 C6 C12 C10 178.6(3) . . . . ?
C5 C6 C12 C2 -1.5(5) . . . . ?
C5 C7 C8 C9 -178.2(3) 3_666 . . . ?
C5 C4 C3 C2 -0.4(5) . . . . ?
C13 N1 C1 O1 -2.8(5) . . . . ?
C13 N1 C1 C2 176.4(3) . . . . ?
C13 N1 C11 O2 7.0(6) . . . . ?
C13 N1 C11 C10 -175.0(3) . . . . ?
C13 C14 C15 C16 -1.3(5) . . . . ?
C13 C18 C17 C16 -0.8(5) . . . . ?
C12 C6 C7 C8 -2.6(5) . . . . ?
C12 C6 C7 C5 178.9(3) . . . 3_666 ?
C12 C6 C5 C7 -178.9(3) . . . 3_666 ?
C12 C6 C5 C4 4.1(4) . . . . ?
C12 C10 C11 O2 173.3(3) . . . . ?
C12 C10 C11 N1 -4.6(6) . . . . ?
C12 C10 C9 C8 -1.1(5) . . . . ?
C12 C2 C3 C4 3.2(5) . . . . ?
C18 C17 C16 C15 -0.1(5) . . . . ?
C3 C4 C5 C6 -3.2(4) . . . . ?
C3 C4 C5 C7 179.9(3) . . . 3_666 ?
C3 C2 C12 C6 -2.2(5) . . . . ?
C3 C2 C12 C10 177.7(3) . . . . ?
C11 N1 C1 O1 178.5(3) . . . . ?
C11 N1 C1 C2 -2.3(5) . . . . ?
C11 N1 C13 C14 -128.0(4) . . . . ?
C11 N1 C13 C18 52.8(4) . . . . ?
C11 C10 C12 C6 -176.0(3) . . . . ?
C11 C10 C12 C2 4.0(5) . . . . ?
C11 C10 C9 C8 176.7(4) . . . . ?
C15 C14 C13 N1 -178.8(3) . . . . ?
C15 C14 C13 C18 0.4(5) . . . . ?
C9 C10 C12 C6 1.8(5) . . . . ?
C9 C10 C12 C2 -178.2(3) . . . . ?
C9 C10 C11 O2 -4.4(6) . . . . ?
C9 C10 C11 N1 177.7(3) . . . . ?

_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
;
####################################################################### 
# 
# 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_PTCDI_Ph_1_47GPa
_database_code_depnum_ccdc_archive 'CCDC 2253188'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PTCDI_Ph_1_47GPa    
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.393 Why?  
RESPONSE: These data come from high-pressure experiment and part of the 
reflection cannot be collected, due to the DAC opening angle, and the 
measurement strategy. 
;
_vrf_PLAT088_PTCDI_Ph_1_47GPa    
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.55 Note    
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber.
;
_vrf_PLAT911_PTCDI_Ph_1_47GPa    
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        907 Report
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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 -0.0011 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0016 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0014 0.0018 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.751(10)
_cell_length_b                   3.6491(3)
_cell_length_c                   17.9271(19)
_cell_angle_alpha                90
_cell_angle_beta                 98.37(3)
_cell_angle_gamma                90
_cell_volume                     1084.2(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    303
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.6770
_cell_measurement_theta_min      2.6480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.393
_diffrn_reflns_Laue_measured_fraction_max 0.221
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            2502
_diffrn_reflns_point_group_measured_fraction_full 0.393
_diffrn_reflns_point_group_measured_fraction_max 0.221
_diffrn_reflns_theta_full        14.237
_diffrn_reflns_theta_max         21.478
_diffrn_reflns_theta_min         2.641
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_detector_type            'Eiger 9M CdTe'
_diffrn_measured_fraction_theta_full 0.393
_diffrn_measured_fraction_theta_max 0.221
_diffrn_measurement_details      
;
 Data were collected at room temperature and pressure of 1.47(2) GPa
 Pressure was determined by monitoring the shift of 
 the ruby R1-fluorescence line.
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_suport 'diamond anvil cell'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.40989
_diffrn_source                   'undulator, ID15B, ESRF'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                795
_reflns_number_total             1435
_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 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1435
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      0.946
_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)+(0.1159P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1974
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C18, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Rigid body (RIGU) restrains
 C17, C18, C13, C14, C15, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, C11, C10, C12, C2, C1, C9, C8, C7, C6, C5, C4, C3, O2, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C15(H15), C4(H4), C3(H3), C14(H14), C16(H16), C18(H18),
 C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8353(4) 0.0728(8) 0.65482(17) 0.055(2) Uani 1 1 d . . . . .
O1 O 0.6875(3) 0.6454(7) 0.81548(14) 0.045(3) Uani 1 1 d . . . . .
N1 N 0.7659(4) 0.3712(7) 0.73704(18) 0.045(2) Uani 1 1 d . . . . .
C10 C 0.7090(5) 0.2912(8) 0.6033(2) 0.038(2) Uani 1 1 d . . . . .
C7 C 0.5741(5) 0.3470(8) 0.48404(19) 0.041(2) Uani 1 1 d . . . . .
C1 C 0.6938(5) 0.5381(8) 0.7516(2) 0.044(2) Uani 1 1 d . . . . .
C8 C 0.6512(5) 0.2053(8) 0.4732(2) 0.046(2) Uani 1 1 d . . . . .
H8 H 0.658551 0.130335 0.425090 0.056 Uiso 1 1 calc R U . . .
C2 C 0.6287(5) 0.5777(8) 0.6901(2) 0.043(2) Uani 1 1 d . . . . .
C9 C 0.7141(5) 0.1753(9) 0.5300(2) 0.046(3) Uani 1 1 d . . . . .
H9 H 0.762248 0.073908 0.519690 0.056 Uiso 1 1 calc R U . . .
C5 C 0.4914(5) 0.6330(8) 0.5733(2) 0.039(2) Uani 1 1 d . . . . .
C11 C 0.7741(5) 0.2374(9) 0.6637(2) 0.042(2) Uani 1 1 d . . . . .
C15 C 0.8907(6) 0.1792(11) 0.9220(3) 0.058(3) Uani 1 1 d . U . . .
H15 H 0.884607 0.079907 0.968598 0.069 Uiso 1 1 calc R U . . .
C4 C 0.4934(5) 0.7691(8) 0.64744(19) 0.044(2) Uani 1 1 d . . . . .
H4 H 0.447321 0.885685 0.658889 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6334(5) 0.4497(8) 0.6157(2) 0.039(2) Uani 1 1 d . . . . .
C3 C 0.5567(5) 0.7430(8) 0.7026(2) 0.045(2) Uani 1 1 d . . . . .
H3 H 0.552421 0.836871 0.750063 0.054 Uiso 1 1 calc R U . . .
C6 C 0.5696(5) 0.4777(7) 0.5592(2) 0.038(2) Uani 1 1 d . . . . .
C13 C 0.8335(6) 0.3500(9) 0.7963(2) 0.044(2) Uani 1 1 d . U . . .
C14 C 0.8258(5) 0.1937(9) 0.8664(2) 0.051(3) Uani 1 1 d . U . . .
H14 H 0.776370 0.099689 0.875017 0.062 Uiso 1 1 calc R U . . .
C16 C 0.9659(6) 0.3104(10) 0.9102(3) 0.059(3) Uani 1 1 d . U . . .
H16 H 1.009856 0.296446 0.948252 0.071 Uiso 1 1 calc R U . . .
C18 C 0.9077(6) 0.4849(9) 0.7841(3) 0.051(2) Uani 1 1 d . U . . .
H18 H 0.913385 0.591038 0.737995 0.061 Uiso 1 1 calc R U . . .
C17 C 0.9742(7) 0.4622(10) 0.8409(3) 0.056(3) Uani 1 1 d . U . . .
H17 H 1.024194 0.549248 0.832134 0.067 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
O2 C11 1.219(9) . ?
O1 C1 1.229(3) . ?
N1 C1 1.410(10) . ?
N1 C11 1.429(4) . ?
N1 C13 1.438(11) . ?
C10 C9 1.395(4) . ?
C10 C11 1.433(12) . ?
C10 C12 1.438(10) . ?
C7 C8 1.429(10) . ?
C7 C5 1.392(10) 3_666 ?
C7 C6 1.442(4) . ?
C1 C2 1.441(12) . ?
C8 H8 0.9300 . ?
C8 C9 1.360(11) . ?
C2 C12 1.426(4) . ?
C2 C3 1.396(10) . ?
C9 H9 0.9300 . ?
C5 C4 1.415(4) . ?
C5 C6 1.481(10) . ?
C15 H15 0.9300 . ?
C15 C14 1.364(13) . ?
C15 C16 1.392(13) . ?
C4 H4 0.9300 . ?
C4 C3 1.344(11) . ?
C12 C6 1.365(11) . ?
C3 H3 0.9300 . ?
C13 C14 1.403(4) . ?
C13 C18 1.383(12) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.386(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.397(14) . ?
C17 H17 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
C1 N1 C11 121.2(6) . . ?
C1 N1 C13 119.3(3) . . ?
C11 N1 C13 119.4(6) . . ?
C9 C10 C11 121.7(6) . . ?
C9 C10 C12 116.3(7) . . ?
C11 C10 C12 121.9(3) . . ?
C8 C7 C6 114.7(7) . . ?
C5 C7 C8 123.3(3) 3_666 . ?
C5 C7 C6 121.9(6) 3_666 . ?
O1 C1 N1 120.2(7) . . ?
O1 C1 C2 121.6(6) . . ?
N1 C1 C2 118.3(3) . . ?
C7 C8 H8 118.5 . . ?
C9 C8 C7 123.0(3) . . ?
C9 C8 H8 118.5 . . ?
C12 C2 C1 123.0(6) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 C12 117.3(6) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 C10 122.3(6) . . ?
C8 C9 H9 118.9 . . ?
C7 C5 C4 125.6(6) 3_666 . ?
C7 C5 C6 121.0(3) 3_666 . ?
C4 C5 C6 113.2(6) . . ?
O2 C11 N1 118.9(7) . . ?
O2 C11 C10 122.1(3) . . ?
N1 C11 C10 118.9(6) . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.2(4) . . ?
C16 C15 H15 119.4 . . ?
C5 C4 H4 117.5 . . ?
C3 C4 C5 125.0(6) . . ?
C3 C4 H4 117.5 . . ?
C2 C12 C10 116.4(7) . . ?
C6 C12 C10 121.8(3) . . ?
C6 C12 C2 121.7(6) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 H3 119.3 . . ?
C7 C6 C5 117.0(7) . . ?
C12 C6 C7 121.8(6) . . ?
C12 C6 C5 121.2(3) . . ?
C14 C13 N1 121.2(7) . . ?
C18 C13 N1 119.6(3) . . ?
C18 C13 C14 119.2(8) . . ?
C15 C14 C13 120.1(7) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(8) . . ?
C17 C16 H16 120.5 . . ?
C13 C18 H18 119.9 . . ?
C13 C18 C17 120.2(4) . . ?
C17 C18 H18 119.9 . . ?
C16 C17 C18 120.2(8) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?

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
O1 C1 C2 C12 -178.7(3) . . . . ?
O1 C1 C2 C3 0.3(6) . . . . ?
N1 C1 C2 C12 1.2(6) . . . . ?
N1 C1 C2 C3 -179.8(3) . . . . ?
N1 C13 C14 C15 -179.5(4) . . . . ?
N1 C13 C18 C17 -179.3(3) . . . . ?
C10 C12 C6 C7 0.5(6) . . . . ?
C10 C12 C6 C5 178.4(3) . . . . ?
C7 C8 C9 C10 -1.9(6) . . . . ?
C7 C5 C4 C3 178.9(4) 3_666 . . . ?
C7 C5 C6 C7 -0.5(6) 3_666 . . . ?
C7 C5 C6 C12 -178.4(3) 3_666 . . . ?
C1 N1 C11 O2 -175.0(4) . . . . ?
C1 N1 C11 C10 3.1(6) . . . . ?
C1 N1 C13 C14 54.1(4) . . . . ?
C1 N1 C13 C18 -126.1(4) . . . . ?
C1 C2 C12 C10 -3.0(5) . . . . ?
C1 C2 C12 C6 177.3(4) . . . . ?
C1 C2 C3 C4 -176.8(4) . . . . ?
C8 C7 C6 C5 179.1(3) . . . . ?
C8 C7 C6 C12 -3.0(5) . . . . ?
C2 C12 C6 C7 -179.7(3) . . . . ?
C2 C12 C6 C5 -1.9(6) . . . . ?
C9 C10 C11 O2 -3.6(7) . . . . ?
C9 C10 C11 N1 178.3(3) . . . . ?
C9 C10 C12 C2 -178.3(3) . . . . ?
C9 C10 C12 C6 1.4(6) . . . . ?
C5 C7 C8 C9 -177.7(4) 3_666 . . . ?
C5 C7 C6 C5 0.5(6) 3_666 . . . ?
C5 C7 C6 C12 178.4(3) 3_666 . . . ?
C5 C4 C3 C2 1.0(6) . . . . ?
C11 N1 C1 O1 178.7(3) . . . . ?
C11 N1 C1 C2 -1.2(6) . . . . ?
C11 N1 C13 C14 -128.6(4) . . . . ?
C11 N1 C13 C18 51.2(5) . . . . ?
C11 C10 C9 C8 176.1(4) . . . . ?
C11 C10 C12 C2 4.8(6) . . . . ?
C11 C10 C12 C6 -175.4(4) . . . . ?
C15 C16 C17 C18 0.5(6) . . . . ?
C4 C5 C6 C7 -177.4(3) . . . . ?
C4 C5 C6 C12 4.7(5) . . . . ?
C12 C10 C9 C8 -0.7(6) . . . . ?
C12 C10 C11 O2 173.1(4) . . . . ?
C12 C10 C11 N1 -5.0(6) . . . . ?
C12 C2 C3 C4 2.2(6) . . . . ?
C3 C2 C12 C10 178.0(3) . . . . ?
C3 C2 C12 C6 -1.7(5) . . . . ?
C6 C7 C8 C9 3.7(6) . . . . ?
C6 C5 C4 C3 -4.4(5) . . . . ?
C13 N1 C1 O1 -4.1(6) . . . . ?
C13 N1 C1 C2 176.0(3) . . . . ?
C13 N1 C11 O2 7.7(6) . . . . ?
C13 N1 C11 C10 -174.1(4) . . . . ?
C13 C18 C17 C16 -1.2(6) . . . . ?
C14 C15 C16 C17 0.8(6) . . . . ?
C14 C13 C18 C17 0.6(5) . . . . ?
C16 C15 C14 C13 -1.4(6) . . . . ?
C18 C13 C14 C15 0.7(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
;
####################################################################### 
# 
# 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_PTCDI_Ph_0_348GPa
_database_code_depnum_ccdc_archive 'CCDC 2253184'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PTCDI_Ph_0_348GPa   
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.396 Why?  
RESPONSE: These data come from high-pressure experiment and part of the 
reflection cannot be collected, due to the DAC opening angle and the 
measurement strategy. 
;
_vrf_PLAT026_PTCDI_Ph_0_348GPa   
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        37% Check 
RESPONSE: This low value is due to the overall poor diffraction quality of the 
crystal.
;
_vrf_PLAT149_PTCDI_Ph_0_348GPa   
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.06 Degree
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT340_PTCDI_Ph_0_348GPa   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01145 Ang.   
RESPONSE: These data come from high-pressure experiment and part of the 
reflection cannot be collected, affecting bond precision. In addition, 
despite multiple attempts to grow better diffracting crystals, it was not 
successful.
;
_vrf_PLAT911_PTCDI_Ph_0_348GPa   
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        958 Report
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2023-03-30

_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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 -0.0011 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0016 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0014 0.0018 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.773(19)
_cell_length_b                   3.8482(6)
_cell_length_c                   18.186(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.63(6)
_cell_angle_gamma                90
_cell_volume                     1160.5(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    257
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.2270
_cell_measurement_theta_min      2.6000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.043
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.396
_diffrn_reflns_Laue_measured_fraction_max 0.246
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            2678
_diffrn_reflns_point_group_measured_fraction_full 0.396
_diffrn_reflns_point_group_measured_fraction_max 0.246
_diffrn_reflns_theta_full        14.237
_diffrn_reflns_theta_max         20.721
_diffrn_reflns_theta_min         2.603
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_detector_type            'Eiger 9M CdTe'
_diffrn_measured_fraction_theta_full 0.396
_diffrn_measured_fraction_theta_max 0.246
_diffrn_measurement_details      
;
 Data were collected at room temperature and pressure of 0.35(2) GPa
 Pressure was determined by monitoring the shift of 
 the ruby R1-fluorescence line.
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_suport 'diamond anvil cell'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.40989
_diffrn_source                   'undulator, ID15B, ESRF'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                568
_reflns_number_total             1537
_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 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1537
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.1516
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      0.823
_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)+(0.1223P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.2150
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C13, C14, C15, C16, C17, C18
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Rigid body (RIGU) restrains
 C13, C18, C17, C16, C15, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, C11, O2, C1, O1, C2, C12, C10, C9, C8, C7, C6, C5, C4, C3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C8(H3), C9(H4), C15(H6), C4(H2), C3(H1), C14(H5), C16(H7), C18(H9), C17(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8324(5) 0.0623(10) 0.6567(2) 0.068(3) Uani 1 1 d . . . . .
O1 O 0.6862(4) 0.6223(8) 0.81306(16) 0.060(4) Uani 1 1 d . . . . .
N1 N 0.7637(6) 0.3560(9) 0.7359(2) 0.049(3) Uani 1 1 d . . . . .
C10 C 0.7058(6) 0.2726(11) 0.6042(2) 0.044(3) Uani 1 1 d . . . . .
C7 C 0.5751(6) 0.3415(10) 0.4861(2) 0.042(3) Uani 1 1 d . . . . .
C1 C 0.6920(6) 0.5146(11) 0.7502(3) 0.044(3) Uani 1 1 d . . . . .
C8 C 0.6469(7) 0.1954(12) 0.4754(3) 0.048(3) Uani 1 1 d . . . . .
H3 H 0.652788 0.117218 0.428108 0.057 Uiso 1 1 calc R U . . .
C2 C 0.6261(6) 0.5584(10) 0.6890(2) 0.041(3) Uani 1 1 d . . . . .
C9 C 0.7111(7) 0.1598(11) 0.5327(3) 0.047(3) Uani 1 1 d . . . . .
H4 H 0.758733 0.058199 0.522844 0.056 Uiso 1 1 calc R U . . .
C5 C 0.4932(6) 0.6255(10) 0.5728(2) 0.043(3) Uani 1 1 d . . . . .
C11 C 0.7709(7) 0.2165(12) 0.6647(3) 0.048(3) Uani 1 1 d . . . . .
C15 C 0.8894(9) 0.1674(14) 0.9185(3) 0.067(4) Uani 1 1 d . U . . .
H6 H 0.884259 0.069394 0.964328 0.080 Uiso 1 1 calc R U . . .
C4 C 0.4919(6) 0.7534(11) 0.6451(2) 0.047(3) Uani 1 1 d . . . . .
H2 H 0.445601 0.863713 0.655721 0.056 Uiso 1 1 calc R U . . .
C12 C 0.6310(6) 0.4319(11) 0.6160(2) 0.045(2) Uani 1 1 d . . . . .
C3 C 0.5574(6) 0.7200(11) 0.7011(2) 0.047(3) Uani 1 1 d . . . . .
H1 H 0.554142 0.810530 0.747951 0.056 Uiso 1 1 calc R U . . .
C6 C 0.5682(6) 0.4673(10) 0.5590(2) 0.043(3) Uani 1 1 d . . . . .
C13 C 0.8326(8) 0.3361(12) 0.7950(3) 0.046(4) Uani 1 1 d . U . . .
C14 C 0.8250(7) 0.1764(11) 0.8630(3) 0.056(4) Uani 1 1 d . U . . .
H5 H 0.776202 0.077044 0.870193 0.067 Uiso 1 1 calc R U . . .
C16 C 0.9613(8) 0.3030(14) 0.9064(3) 0.067(4) Uani 1 1 d . U . . .
H7 H 1.005468 0.293902 0.944039 0.080 Uiso 1 1 calc R U . . .
C18 C 0.9062(9) 0.4699(13) 0.7842(4) 0.052(3) Uani 1 1 d . U . . .
H9 H 0.912251 0.571773 0.738987 0.063 Uiso 1 1 calc R U . . .
C17 C 0.9695(9) 0.4522(14) 0.8397(3) 0.064(4) Uani 1 1 d . U . . .
H8 H 1.019108 0.542622 0.832427 0.076 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
O2 C11 1.217(12) . ?
O1 C1 1.234(4) . ?
N1 C1 1.408(13) . ?
N1 C11 1.424(5) . ?
N1 C13 1.456(16) . ?
C10 C9 1.388(5) . ?
C10 C11 1.445(15) . ?
C10 C12 1.440(13) . ?
C7 C8 1.369(13) . ?
C7 C5 1.452(13) 3_666 ?
C7 C6 1.432(4) . ?
C1 C2 1.456(14) . ?
C8 H3 0.9300 . ?
C8 C9 1.389(15) . ?
C2 C12 1.427(5) . ?
C2 C3 1.357(12) . ?
C9 H4 0.9300 . ?
C5 C4 1.408(5) . ?
C5 C6 1.453(12) . ?
C15 H6 0.9300 . ?
C15 C14 1.364(17) . ?
C15 C16 1.362(17) . ?
C4 H2 0.9300 . ?
C4 C3 1.387(13) . ?
C12 C6 1.370(13) . ?
C3 H1 0.9300 . ?
C13 C14 1.405(6) . ?
C13 C18 1.377(18) . ?
C14 H5 0.9300 . ?
C16 H7 0.9300 . ?
C16 C17 1.368(7) . ?
C18 H9 0.9300 . ?
C18 C17 1.353(19) . ?
C17 H8 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
C1 N1 C11 121.5(8) . . ?
C1 N1 C13 119.5(4) . . ?
C11 N1 C13 119.0(8) . . ?
C9 C10 C11 121.3(8) . . ?
C9 C10 C12 116.9(8) . . ?
C12 C10 C11 121.7(4) . . ?
C8 C7 C5 122.9(4) . 3_666 ?
C8 C7 C6 117.8(8) . . ?
C6 C7 C5 119.3(8) . 3_666 ?
O1 C1 N1 120.3(8) . . ?
O1 C1 C2 120.9(8) . . ?
N1 C1 C2 118.8(4) . . ?
C7 C8 H3 118.9 . . ?
C7 C8 C9 122.2(4) . . ?
C9 C8 H3 118.9 . . ?
C12 C2 C1 121.9(8) . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 C12 118.5(8) . . ?
C10 C9 C8 121.4(8) . . ?
C10 C9 H4 119.3 . . ?
C8 C9 H4 119.3 . . ?
C7 C5 C6 121.1(4) 3_666 . ?
C4 C5 C7 122.5(7) . 3_666 ?
C4 C5 C6 116.3(8) . . ?
O2 C11 N1 118.7(9) . . ?
O2 C11 C10 122.7(5) . . ?
N1 C11 C10 118.6(8) . . ?
C14 C15 H6 120.2 . . ?
C16 C15 H6 120.2 . . ?
C16 C15 C14 119.5(5) . . ?
C5 C4 H2 119.0 . . ?
C3 C4 C5 122.1(7) . . ?
C3 C4 H2 119.0 . . ?
C2 C12 C10 117.2(8) . . ?
C6 C12 C10 121.2(4) . . ?
C6 C12 C2 121.6(8) . . ?
C2 C3 C4 121.5(4) . . ?
C2 C3 H1 119.3 . . ?
C4 C3 H1 119.3 . . ?
C7 C6 C5 119.6(8) . . ?
C12 C6 C7 120.4(8) . . ?
C12 C6 C5 119.9(4) . . ?
C14 C13 N1 120.3(9) . . ?
C18 C13 N1 120.2(5) . . ?
C18 C13 C14 119.4(10) . . ?
C15 C14 C13 119.8(10) . . ?
C15 C14 H5 120.1 . . ?
C13 C14 H5 120.1 . . ?
C15 C16 H7 119.6 . . ?
C15 C16 C17 120.9(11) . . ?
C17 C16 H7 119.6 . . ?
C13 C18 H9 120.2 . . ?
C17 C18 C13 119.6(6) . . ?
C17 C18 H9 120.2 . . ?
C16 C17 H8 119.6 . . ?
C18 C17 C16 120.8(12) . . ?
C18 C17 H8 119.6 . . ?

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
O1 C1 C2 C12 -179.1(4) . . . . ?
O1 C1 C2 C3 0.1(8) . . . . ?
N1 C1 C2 C12 2.8(8) . . . . ?
N1 C1 C2 C3 -178.0(5) . . . . ?
N1 C13 C14 C15 -178.3(5) . . . . ?
N1 C13 C18 C17 179.5(5) . . . . ?
C10 C12 C6 C7 0.9(8) . . . . ?
C10 C12 C6 C5 179.3(4) . . . . ?
C7 C8 C9 C10 -0.2(9) . . . . ?
C7 C5 C4 C3 179.9(5) 3_666 . . . ?
C7 C5 C6 C7 0.0(8) 3_666 . . . ?
C7 C5 C6 C12 -178.4(5) 3_666 . . . ?
C1 N1 C11 O2 -175.3(5) . . . . ?
C1 N1 C11 C10 6.5(8) . . . . ?
C1 N1 C13 C14 56.5(6) . . . . ?
C1 N1 C13 C18 -124.4(6) . . . . ?
C1 C2 C12 C10 -3.0(7) . . . . ?
C1 C2 C12 C6 178.6(5) . . . . ?
C1 C2 C3 C4 -177.1(5) . . . . ?
C8 C7 C6 C5 179.8(4) . . . . ?
C8 C7 C6 C12 -1.8(7) . . . . ?
C2 C12 C6 C7 179.3(4) . . . . ?
C2 C12 C6 C5 -2.3(8) . . . . ?
C9 C10 C11 O2 -1.7(9) . . . . ?
C9 C10 C11 N1 176.4(5) . . . . ?
C9 C10 C12 C2 -178.1(4) . . . . ?
C9 C10 C12 C6 0.4(7) . . . . ?
C5 C7 C8 C9 -178.8(5) 3_666 . . . ?
C5 C7 C6 C5 0.0(8) 3_666 . . . ?
C5 C7 C6 C12 178.4(5) 3_666 . . . ?
C5 C4 C3 C2 -0.7(8) . . . . ?
C11 N1 C1 O1 177.4(4) . . . . ?
C11 N1 C1 C2 -4.5(7) . . . . ?
C11 N1 C13 C14 -124.1(6) . . . . ?
C11 N1 C13 C18 55.0(7) . . . . ?
C11 C10 C9 C8 176.2(6) . . . . ?
C11 C10 C12 C2 5.0(7) . . . . ?
C11 C10 C12 C6 -176.6(5) . . . . ?
C15 C16 C17 C18 0.2(9) . . . . ?
C4 C5 C6 C7 -177.9(4) . . . . ?
C4 C5 C6 C12 3.6(7) . . . . ?
C12 C10 C9 C8 -0.8(8) . . . . ?
C12 C10 C11 O2 175.1(6) . . . . ?
C12 C10 C11 N1 -6.7(8) . . . . ?
C12 C2 C3 C4 2.1(8) . . . . ?
C3 C2 C12 C10 177.8(5) . . . . ?
C3 C2 C12 C6 -0.6(7) . . . . ?
C6 C7 C8 C9 1.5(8) . . . . ?
C6 C5 C4 C3 -2.2(7) . . . . ?
C13 N1 C1 O1 -3.2(8) . . . . ?
C13 N1 C1 C2 174.9(5) . . . . ?
C13 N1 C11 O2 5.3(8) . . . . ?
C13 N1 C11 C10 -173.0(5) . . . . ?
C13 C18 C17 C16 0.0(9) . . . . ?
C14 C15 C16 C17 0.9(9) . . . . ?
C14 C13 C18 C17 -1.4(8) . . . . ?
C16 C15 C14 C13 -2.3(9) . . . . ?
C18 C13 C14 C15 2.5(8) . . . . ?

_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
;
####################################################################### 
# 
# 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_PTCDI_Ph_1_75GPa
_database_code_depnum_ccdc_archive 'CCDC 2253189'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PTCDI_Ph_1_75GPa    
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.394 Why?  
RESPONSE: These data come from high-pressure experiment and part of the 
reflection cannot be collected, due to the DAC opening angle, and the 
measurement strategy. 
;
_vrf_PLAT088_PTCDI_Ph_1_75GPa    
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.44 Note  
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber.
;
_vrf_PLAT911_PTCDI_Ph_1_75GPa    
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        896 Report
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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 -0.0011 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0016 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0014 0.0018 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.703(10)
_cell_length_b                   3.6174(3)
_cell_length_c                   17.8589(18)
_cell_angle_alpha                90
_cell_angle_beta                 98.33(3)
_cell_angle_gamma                90
_cell_volume                     1067.7(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.2810
_cell_measurement_theta_min      2.6510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.394
_diffrn_reflns_Laue_measured_fraction_max 0.222
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            2475
_diffrn_reflns_point_group_measured_fraction_full 0.394
_diffrn_reflns_point_group_measured_fraction_max 0.222
_diffrn_reflns_theta_full        14.237
_diffrn_reflns_theta_max         21.441
_diffrn_reflns_theta_min         2.651
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'Eiger 9M CdTe'
_diffrn_measurement_specimen_suport 'diamond anvil cell'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.394
_diffrn_measured_fraction_theta_max 0.222
_diffrn_measurement_details      
;
 Data were collected at room temperature and pressure of 1.75(2) GPa
 Pressure was determined by monitoring the shift of 
 the ruby R1-fluorescence line.
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0239602000
_diffrn_orient_matrix_UB_12      -0.0245012000
_diffrn_orient_matrix_UB_13      -0.0066348000
_diffrn_orient_matrix_UB_21      0.0058152000
_diffrn_orient_matrix_UB_22      -0.0543274000
_diffrn_orient_matrix_UB_23      -0.0186310000
_diffrn_orient_matrix_UB_31      0.0028099000
_diffrn_orient_matrix_UB_32      -0.0962870000
_diffrn_orient_matrix_UB_33      0.0121403000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.40989
_diffrn_source                   'undulator, ID15B, ESRF'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                788
_reflns_number_total             1414
_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 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1414
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      0.934
_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)+(0.0976P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1701
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C18, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Rigid body (RIGU) restrains
 C18, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, C11, C10, C12, C2, C1, C9, C8, C7, C6, C5, C4, C3, O2, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C14(H14), C8(H8), C18(H18), C3(H3), C15(H15), C9(H9), C17(H17),
 C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.6876(3) 0.6502(6) 0.81566(12) 0.042(2) Uani 1 1 d . . . . .
O2 O 0.8363(4) 0.0749(7) 0.65458(15) 0.052(2) Uani 1 1 d . . . . .
C6 C 0.5691(4) 0.4794(7) 0.55903(18) 0.034(2) Uani 1 1 d . . . . .
N1 N 0.7666(4) 0.3750(7) 0.73714(16) 0.042(2) Uani 1 1 d . . . . .
C7 C 0.5748(4) 0.3461(7) 0.48391(18) 0.040(2) Uani 1 1 d . . . . .
C4 C 0.4932(4) 0.7723(8) 0.64753(17) 0.038(2) Uani 1 1 d . . . . .
H4 H 0.446661 0.887765 0.658898 0.046 Uiso 1 1 calc R U . . .
C14 C 0.8265(5) 0.1961(8) 0.8672(2) 0.044(2) Uani 1 1 d . U . . .
H14 H 0.776869 0.102041 0.875900 0.053 Uiso 1 1 calc R U . . .
C1 C 0.6936(5) 0.5422(7) 0.75155(19) 0.037(2) Uani 1 1 d . . . . .
C10 C 0.7091(4) 0.2943(7) 0.60297(18) 0.036(2) Uani 1 1 d . . . . .
C2 C 0.6293(4) 0.5822(7) 0.69022(18) 0.037(2) Uani 1 1 d . . . . .
C8 C 0.6513(5) 0.2077(8) 0.47264(19) 0.044(2) Uani 1 1 d . . . . .
H8 H 0.658626 0.133785 0.424221 0.053 Uiso 1 1 calc R U . . .
C5 C 0.4921(4) 0.6344(7) 0.57357(18) 0.038(2) Uani 1 1 d . . . . .
C13 C 0.8339(5) 0.3511(8) 0.7965(2) 0.041(2) Uani 1 1 d . U . . .
C12 C 0.6338(4) 0.4534(7) 0.61581(17) 0.036(2) Uani 1 1 d . . . . .
C18 C 0.9094(5) 0.4876(9) 0.7848(2) 0.048(2) Uani 1 1 d . U . . .
H18 H 0.915735 0.592711 0.738468 0.058 Uiso 1 1 calc R U . . .
C3 C 0.5566(4) 0.7485(8) 0.70252(18) 0.039(2) Uani 1 1 d . . . . .
H3 H 0.552275 0.844812 0.750051 0.047 Uiso 1 1 calc R U . . .
C11 C 0.7738(5) 0.2411(8) 0.6633(2) 0.039(2) Uani 1 1 d . . . . .
C15 C 0.8900(5) 0.1816(10) 0.9224(2) 0.050(2) Uani 1 1 d . U . . .
H15 H 0.883459 0.084587 0.969366 0.060 Uiso 1 1 calc R U . . .
C9 C 0.7145(5) 0.1779(8) 0.52935(19) 0.042(2) Uani 1 1 d . . . . .
H9 H 0.762867 0.076830 0.518835 0.050 Uiso 1 1 calc R U . . .
C17 C 0.9730(6) 0.4674(9) 0.8403(2) 0.052(2) Uani 1 1 d . U . . .
H17 H 1.022793 0.560479 0.831709 0.062 Uiso 1 1 calc R U . . .
C16 C 0.9663(6) 0.3114(10) 0.9102(2) 0.053(2) Uani 1 1 d . U . . .
H16 H 1.010970 0.293310 0.947696 0.064 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
O1 C1 1.227(3) . ?
O2 C11 1.233(8) . ?
C6 C7 1.442(3) . ?
C6 C5 1.460(9) . ?
C6 C12 1.373(10) . ?
N1 C1 1.417(9) . ?
N1 C13 1.432(10) . ?
N1 C11 1.426(3) . ?
C7 C8 1.413(10) . ?
C7 C5 1.406(9) 3_666 ?
C4 H4 0.9300 . ?
C4 C5 1.410(4) . ?
C4 C3 1.339(10) . ?
C14 H14 0.9300 . ?
C14 C13 1.404(4) . ?
C14 C15 1.340(12) . ?
C1 C2 1.426(10) . ?
C10 C12 1.432(9) . ?
C10 C11 1.425(11) . ?
C10 C9 1.396(3) . ?
C2 C12 1.421(3) . ?
C2 C3 1.400(9) . ?
C8 H8 0.9300 . ?
C8 C9 1.358(10) . ?
C13 C18 1.398(11) . ?
C18 H18 0.9300 . ?
C18 C17 1.347(12) . ?
C3 H3 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.405(12) . ?
C9 H9 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.388(5) . ?
C16 H16 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 C6 C5 118.2(6) . . ?
C12 C6 C7 120.9(6) . . ?
C12 C6 C5 120.9(3) . . ?
C1 N1 C13 119.7(3) . . ?
C1 N1 C11 120.2(6) . . ?
C11 N1 C13 120.0(5) . . ?
C8 C7 C6 115.7(6) . . ?
C5 C7 C6 120.7(6) 3_666 . ?
C5 C7 C8 123.6(3) 3_666 . ?
C5 C4 H4 117.8 . . ?
C3 C4 H4 117.8 . . ?
C3 C4 C5 124.4(5) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C15 C14 C13 120.9(7) . . ?
O1 C1 N1 119.6(6) . . ?
O1 C1 C2 122.0(6) . . ?
N1 C1 C2 118.4(3) . . ?
C11 C10 C12 121.4(3) . . ?
C9 C10 C12 116.7(6) . . ?
C9 C10 C11 121.8(6) . . ?
C12 C2 C1 123.3(5) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 C12 116.9(6) . . ?
C7 C8 H8 118.5 . . ?
C9 C8 C7 122.9(3) . . ?
C9 C8 H8 118.5 . . ?
C7 C5 C6 121.2(3) 3_666 . ?
C7 C5 C4 124.5(5) 3_666 . ?
C4 C5 C6 114.3(6) . . ?
C14 C13 N1 121.9(6) . . ?
C18 C13 N1 119.8(3) . . ?
C18 C13 C14 118.3(7) . . ?
C6 C12 C10 121.6(3) . . ?
C6 C12 C2 121.7(5) . . ?
C2 C12 C10 116.7(6) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
O2 C11 N1 118.0(6) . . ?
O2 C11 C10 122.2(3) . . ?
C10 C11 N1 119.8(5) . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
C10 C9 H9 119.0 . . ?
C8 C9 C10 122.0(6) . . ?
C8 C9 H9 119.0 . . ?
C18 C17 H17 119.1 . . ?
C18 C17 C16 121.8(7) . . ?
C16 C17 H17 119.1 . . ?
C15 C16 H16 121.0 . . ?
C17 C16 C15 118.0(7) . . ?
C17 C16 H16 121.0 . . ?

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
O1 C1 C2 C12 -178.7(3) . . . . ?
O1 C1 C2 C3 -0.1(6) . . . . ?
C6 C7 C8 C9 4.1(5) . . . . ?
N1 C1 C2 C12 1.9(5) . . . . ?
N1 C1 C2 C3 -179.6(3) . . . . ?
N1 C13 C18 C17 179.8(3) . . . . ?
C7 C6 C5 C7 0.0(5) . . . 3_666 ?
C7 C6 C5 C4 -177.4(2) . . . . ?
C7 C6 C12 C10 0.1(5) . . . . ?
C7 C6 C12 C2 -179.8(3) . . . . ?
C7 C8 C9 C10 -2.2(6) . . . . ?
C14 C13 C18 C17 0.3(5) . . . . ?
C14 C15 C16 C17 2.5(5) . . . . ?
C1 N1 C13 C14 52.9(4) . . . . ?
C1 N1 C13 C18 -126.5(4) . . . . ?
C1 N1 C11 O2 -175.1(3) . . . . ?
C1 N1 C11 C10 3.5(5) . . . . ?
C1 C2 C12 C6 176.6(3) . . . . ?
C1 C2 C12 C10 -3.3(5) . . . . ?
C1 C2 C3 C4 -176.1(3) . . . . ?
C5 C6 C7 C8 178.5(2) . . . . ?
C5 C6 C7 C5 0.0(5) . . . 3_666 ?
C5 C6 C12 C10 178.5(3) . . . . ?
C5 C6 C12 C2 -1.4(5) . . . . ?
C5 C7 C8 C9 -177.5(3) 3_666 . . . ?
C5 C4 C3 C2 0.6(5) . . . . ?
C13 N1 C1 O1 -3.2(5) . . . . ?
C13 N1 C1 C2 176.2(3) . . . . ?
C13 N1 C11 O2 6.8(5) . . . . ?
C13 N1 C11 C10 -174.6(3) . . . . ?
C13 C14 C15 C16 -1.9(5) . . . . ?
C13 C18 C17 C16 0.3(5) . . . . ?
C12 C6 C7 C8 -3.0(5) . . . . ?
C12 C6 C7 C5 178.5(3) . . . 3_666 ?
C12 C6 C5 C7 -178.5(3) . . . 3_666 ?
C12 C6 C5 C4 4.2(4) . . . . ?
C12 C10 C11 O2 173.4(3) . . . . ?
C12 C10 C11 N1 -5.2(6) . . . . ?
C12 C10 C9 C8 -1.0(5) . . . . ?
C12 C2 C3 C4 2.5(5) . . . . ?
C18 C17 C16 C15 -1.6(5) . . . . ?
C3 C4 C5 C6 -3.8(5) . . . . ?
C3 C4 C5 C7 178.9(4) . . . 3_666 ?
C3 C2 C12 C6 -2.1(5) . . . . ?
C3 C2 C12 C10 178.0(3) . . . . ?
C11 N1 C1 O1 178.7(3) . . . . ?
C11 N1 C1 C2 -1.9(5) . . . . ?
C11 N1 C13 C14 -128.9(4) . . . . ?
C11 N1 C13 C18 51.6(4) . . . . ?
C11 C10 C12 C6 -174.9(3) . . . . ?
C11 C10 C12 C2 5.0(5) . . . . ?
C11 C10 C9 C8 175.9(4) . . . . ?
C15 C14 C13 N1 -178.9(3) . . . . ?
C15 C14 C13 C18 0.5(5) . . . . ?
C9 C10 C12 C6 2.0(5) . . . . ?
C9 C10 C12 C2 -178.1(3) . . . . ?
C9 C10 C11 O2 -3.4(6) . . . . ?
C9 C10 C11 N1 178.0(3) . . . . ?

_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
;
####################################################################### 
# 
# 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_PTCDI_Ph_2_15GPa
_database_code_depnum_ccdc_archive 'CCDC 2253190'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PTCDI_Ph_2_15GPa    
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.385 Why?   
RESPONSE: These data come from high-pressure experiment and part of the 
reflection cannot be collected, due to the DAC opening angle, and the 
measurement strategy. 
;
_vrf_PLAT088_PTCDI_Ph_2_15GPa    
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.31 Note    
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber.
;
_vrf_PLAT340_PTCDI_Ph_2_15GPa    
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.011 Ang.  
RESPONSE: These data comes from high-pressure experiment and part of the reflection 
cannot be collected, affecting bond precision. In addition, despite multiple attempts 
to grow better diffracting crystals, it was not successful.
;
_vrf_PLAT911_PTCDI_Ph_2_15GPa    
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        897 Report
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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 -0.0011 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0016 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0014 0.0018 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.688(10)
_cell_length_b                   3.5812(3)
_cell_length_c                   17.802(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.25(3)
_cell_angle_gamma                90
_cell_volume                     1052.9(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    369
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.8600
_cell_measurement_theta_min      2.6620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.047
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.385
_diffrn_reflns_Laue_measured_fraction_max 0.249
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            2381
_diffrn_reflns_point_group_measured_fraction_full 0.385
_diffrn_reflns_point_group_measured_fraction_max 0.249
_diffrn_reflns_theta_full        14.237
_diffrn_reflns_theta_max         20.611
_diffrn_reflns_theta_min         2.660
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_detector_type            'Eiger 9M CdTe'
_diffrn_measured_fraction_theta_full 0.385
_diffrn_measured_fraction_theta_max 0.249
_diffrn_measurement_details      
;
 Data were collected at room temperature and pressure of 2.15(2) GPa
 Pressure was determined by monitoring the shift of 
 the ruby R1-fluorescence line.
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_suport 'diamond anvil cell'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.40989
_diffrn_source                   'undulator, ID15B, ESRF'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                686
_reflns_number_total             1389
_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 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1389
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.0680
_refine_ls_restrained_S_all      0.947
_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)+(0.1534P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2031
_refine_ls_wR_factor_ref         0.2522
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C13, C14, C15, C16, C17, C18
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Rigid body (RIGU) restrains
 C13, C18, C17, C16, C15, C14
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, C1, C2, C12, C10, C11, C3, C4, C5, C6, C7, C8, C9, O2, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C15(H15), C4(H4), C3(H3), C14(H14), C16(H16), C18(H18),
 C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8363(5) 0.0769(10) 0.6537(2) 0.059(3) Uani 1 1 d . . . . .
O1 O 0.6883(4) 0.6575(9) 0.81654(17) 0.046(3) Uani 1 1 d . . . . .
N1 N 0.7677(5) 0.3807(10) 0.7373(2) 0.047(3) Uani 1 1 d . . . . .
C10 C 0.7086(6) 0.3028(11) 0.6020(3) 0.045(2) Uani 1 1 d . . . . .
C7 C 0.5751(6) 0.3474(10) 0.4840(3) 0.051(3) Uani 1 1 d . . . . .
C1 C 0.6945(6) 0.5486(10) 0.7522(3) 0.043(3) Uani 1 1 d . . . . .
C8 C 0.6526(6) 0.2074(11) 0.4726(3) 0.051(3) Uani 1 1 d . . . . .
H8 H 0.659859 0.130477 0.424101 0.061 Uiso 1 1 calc R U . . .
C2 C 0.6296(6) 0.5881(11) 0.6906(3) 0.042(2) Uani 1 1 d . . . . .
C9 C 0.7163(7) 0.1815(12) 0.5292(3) 0.054(3) Uani 1 1 d . . . . .
H9 H 0.765231 0.082323 0.519291 0.065 Uiso 1 1 calc R U . . .
C5 C 0.4922(6) 0.6353(10) 0.5739(2) 0.046(3) Uani 1 1 d . . . . .
C11 C 0.7741(6) 0.2475(11) 0.6629(3) 0.046(2) Uani 1 1 d . . . . .
C15 C 0.8917(8) 0.1877(14) 0.9236(3) 0.055(3) Uani 1 1 d . U . . .
H15 H 0.885064 0.092874 0.970959 0.066 Uiso 1 1 calc R U . . .
C4 C 0.4939(6) 0.7794(10) 0.6484(2) 0.042(3) Uani 1 1 d . . . . .
H4 H 0.447688 0.899276 0.659748 0.051 Uiso 1 1 calc R U . . .
C12 C 0.6347(6) 0.4568(10) 0.6158(2) 0.041(2) Uani 1 1 d . . . . .
C3 C 0.5567(6) 0.7551(11) 0.7030(3) 0.044(3) Uani 1 1 d . . . . .
H3 H 0.552279 0.851488 0.750695 0.053 Uiso 1 1 calc R U . . .
C6 C 0.5691(6) 0.4839(9) 0.5586(2) 0.040(2) Uani 1 1 d . . . . .
C13 C 0.8339(7) 0.3546(12) 0.7967(3) 0.053(3) Uani 1 1 d . U . . .
C14 C 0.8279(7) 0.1993(11) 0.8686(3) 0.049(3) Uani 1 1 d . U . . .
H14 H 0.778508 0.102979 0.877967 0.059 Uiso 1 1 calc R U . . .
C16 C 0.9680(7) 0.3149(14) 0.9114(3) 0.058(3) Uani 1 1 d . U . . .
H16 H 1.013015 0.295027 0.948621 0.070 Uiso 1 1 calc R U . . .
C18 C 0.9116(7) 0.4892(12) 0.7851(3) 0.060(3) Uani 1 1 d . U . . .
H18 H 0.918899 0.588695 0.738285 0.072 Uiso 1 1 calc R U . . .
C17 C 0.9732(8) 0.4733(13) 0.8405(3) 0.064(3) Uani 1 1 d . U . . .
H17 H 1.022622 0.572476 0.831972 0.076 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
O2 C11 1.236(11) . ?
O1 C1 1.229(4) . ?
N1 C1 1.421(11) . ?
N1 C11 1.427(5) . ?
N1 C13 1.417(13) . ?
C10 C9 1.390(5) . ?
C10 C11 1.438(14) . ?
C10 C12 1.403(13) . ?
C7 C8 1.428(14) . ?
C7 C5 1.412(14) 3_666 ?
C7 C6 1.433(4) . ?
C1 C2 1.432(14) . ?
C8 H8 0.9300 . ?
C8 C9 1.360(14) . ?
C2 C12 1.426(5) . ?
C2 C3 1.402(12) . ?
C9 H9 0.9300 . ?
C5 C4 1.420(5) . ?
C5 C6 1.455(12) . ?
C15 H15 0.9300 . ?
C15 C14 1.340(17) . ?
C15 C16 1.399(15) . ?
C4 H4 0.9300 . ?
C4 C3 1.325(13) . ?
C12 C6 1.387(13) . ?
C3 H3 0.9300 . ?
C13 C14 1.413(5) . ?
C13 C18 1.426(15) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.398(7) . ?
C18 H18 0.9300 . ?
C18 C17 1.321(17) . ?
C17 H17 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
C1 N1 C11 119.7(8) . . ?
C13 N1 C1 119.3(4) . . ?
C13 N1 C11 121.1(7) . . ?
C9 C10 C11 119.8(8) . . ?
C9 C10 C12 119.2(9) . . ?
C12 C10 C11 120.9(4) . . ?
C8 C7 C6 115.9(9) . . ?
C5 C7 C8 123.6(4) 3_666 . ?
C5 C7 C6 120.5(8) 3_666 . ?
O1 C1 N1 119.8(8) . . ?
O1 C1 C2 121.8(8) . . ?
N1 C1 C2 118.3(4) . . ?
C7 C8 H8 118.5 . . ?
C9 C8 C7 123.1(4) . . ?
C9 C8 H8 118.5 . . ?
C12 C2 C1 122.9(7) . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 C12 117.2(8) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.2(8) . . ?
C8 C9 H9 119.9 . . ?
C7 C5 C4 124.9(7) 3_666 . ?
C7 C5 C6 120.7(3) 3_666 . ?
C4 C5 C6 114.2(8) . . ?
O2 C11 N1 117.7(8) . . ?
O2 C11 C10 122.0(4) . . ?
N1 C11 C10 120.3(7) . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.5(5) . . ?
C16 C15 H15 119.2 . . ?
C5 C4 H4 117.7 . . ?
C3 C4 C5 124.6(7) . . ?
C3 C4 H4 117.7 . . ?
C10 C12 C2 117.6(8) . . ?
C6 C12 C10 121.3(4) . . ?
C6 C12 C2 121.0(7) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.7(4) . . ?
C4 C3 H3 119.1 . . ?
C7 C6 C5 118.8(8) . . ?
C12 C6 C7 120.2(7) . . ?
C12 C6 C5 120.9(3) . . ?
N1 C13 C18 119.9(4) . . ?
C14 C13 N1 123.5(9) . . ?
C14 C13 C18 116.7(10) . . ?
C15 C14 C13 121.5(9) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C15 C16 H16 121.7 . . ?
C17 C16 C15 116.6(10) . . ?
C17 C16 H16 121.7 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.3(5) . . ?
C17 C18 H18 119.9 . . ?
C16 C17 H17 118.3 . . ?
C18 C17 C16 123.3(10) . . ?
C18 C17 H17 118.3 . . ?

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
O1 C1 C2 C12 -178.6(4) . . . . ?
O1 C1 C2 C3 0.1(8) . . . . ?
N1 C1 C2 C12 1.8(7) . . . . ?
N1 C1 C2 C3 -179.5(4) . . . . ?
N1 C13 C14 C15 -178.5(5) . . . . ?
N1 C13 C18 C17 178.6(4) . . . . ?
C10 C12 C6 C7 1.2(7) . . . . ?
C10 C12 C6 C5 178.4(4) . . . . ?
C7 C8 C9 C10 -1.7(8) . . . . ?
C7 C5 C4 C3 178.5(5) 3_666 . . . ?
C7 C5 C6 C7 -0.9(7) 3_666 . . . ?
C7 C5 C6 C12 -178.2(4) 3_666 . . . ?
C1 N1 C11 O2 -174.4(5) . . . . ?
C1 N1 C11 C10 3.7(7) . . . . ?
C1 N1 C13 C14 52.1(6) . . . . ?
C1 N1 C13 C18 -127.9(5) . . . . ?
C1 C2 C12 C10 -3.8(7) . . . . ?
C1 C2 C12 C6 176.8(5) . . . . ?
C1 C2 C3 C4 -176.5(4) . . . . ?
C8 C7 C6 C5 179.1(3) . . . . ?
C8 C7 C6 C12 -3.5(7) . . . . ?
C2 C12 C6 C7 -179.4(4) . . . . ?
C2 C12 C6 C5 -2.2(7) . . . . ?
C9 C10 C11 O2 -3.8(9) . . . . ?
C9 C10 C11 N1 178.1(4) . . . . ?
C9 C10 C12 C2 -178.2(4) . . . . ?
C9 C10 C12 C6 1.2(7) . . . . ?
C5 C7 C8 C9 -177.9(4) 3_666 . . . ?
C5 C7 C6 C5 0.9(7) 3_666 . . . ?
C5 C7 C6 C12 178.2(4) 3_666 . . . ?
C5 C4 C3 C2 1.7(7) . . . . ?
C11 N1 C1 O1 178.7(4) . . . . ?
C11 N1 C1 C2 -1.8(7) . . . . ?
C11 N1 C13 C14 -129.1(5) . . . . ?
C11 N1 C13 C18 50.9(6) . . . . ?
C11 C10 C9 C8 175.1(5) . . . . ?
C11 C10 C12 C2 5.7(7) . . . . ?
C11 C10 C12 C6 -174.8(4) . . . . ?
C15 C16 C17 C18 -3.5(8) . . . . ?
C4 C5 C6 C7 -177.1(3) . . . . ?
C4 C5 C6 C12 5.6(6) . . . . ?
C12 C10 C9 C8 -0.9(7) . . . . ?
C12 C10 C11 O2 172.2(5) . . . . ?
C12 C10 C11 N1 -5.9(8) . . . . ?
C12 C2 C3 C4 2.3(7) . . . . ?
C3 C2 C12 C10 177.5(4) . . . . ?
C3 C2 C12 C6 -1.9(7) . . . . ?
C6 C7 C8 C9 3.9(7) . . . . ?
C6 C5 C4 C3 -5.5(6) . . . . ?
C13 N1 C1 O1 -2.5(7) . . . . ?
C13 N1 C1 C2 177.1(4) . . . . ?
C13 N1 C11 O2 6.8(8) . . . . ?
C13 N1 C11 C10 -175.1(5) . . . . ?
C13 C18 C17 C16 2.6(8) . . . . ?
C14 C15 C16 C17 3.5(8) . . . . ?
C14 C13 C18 C17 -1.5(7) . . . . ?
C16 C15 C14 C13 -2.6(8) . . . . ?
C18 C13 C14 C15 1.5(7) . . . . ?

_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
;
####################################################################### 
# 
# 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_PTCDI_Ph_2_50GPa
_database_code_depnum_ccdc_archive 'CCDC 2253191'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PTCDI_Ph_2_50GPa    
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.349 Why?    
RESPONSE: These data come from high-pressure experiment and part of the 
reflection cannot be collected, due to the DAC opening angle, and the 
measurement strategy. 
;
_vrf_PLAT088_PTCDI_Ph_2_50GPa    
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.71 Note  
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber.
;
_vrf_PLAT340_PTCDI_Ph_2_50GPa    
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01315 Ang.    
RESPONSE: These data comes from high-pressure experiment and part of the reflection 
cannot be collected, affecting bond precision. In addition, despite multiple attempts 
to grow better diffracting crystals, it was not successful.
;
_vrf_PLAT911_PTCDI_Ph_2_50GPa    
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600       1021 Report
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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 -0.0011 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0016 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0014 0.0018 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.664(12)
_cell_length_b                   3.5410(2)
_cell_length_c                   17.695(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.11(4)
_cell_angle_gamma                90
_cell_volume                     1033.7(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    360
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.9350
_cell_measurement_theta_min      2.6720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.048
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_Laue_measured_fraction_full 0.349
_diffrn_reflns_Laue_measured_fraction_max 0.205
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            2187
_diffrn_reflns_point_group_measured_fraction_full 0.349
_diffrn_reflns_point_group_measured_fraction_max 0.205
_diffrn_reflns_theta_full        14.237
_diffrn_reflns_theta_max         21.525
_diffrn_reflns_theta_min         2.676
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_detector_type            'Eiger 9M CdTe'
_diffrn_measured_fraction_theta_full 0.349
_diffrn_measured_fraction_theta_max 0.205
_diffrn_measurement_details      
;
 Data were collected at room temperature and pressure of 2.50(2) GPa
 Pressure was determined by monitoring the shift of 
 the ruby R1-fluorescence line.
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_suport 'diamond anvil cell'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.40989
_diffrn_source                   'undulator, ID15B, ESRF'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                603
_reflns_number_total             1274
_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 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1274
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.1328
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      0.886
_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)+(0.1291P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1802
_refine_ls_wR_factor_ref         0.2314
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C14, C13, C18, C17, C16, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Rigid body (RIGU) restrains
 C14, C13, C18, C17, C16, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, C1, C2, C12, C10, C11, O2, O1, C3, C4, C5, C6, C7, C8, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C15(H15), C4(H4), C3(H3), C14(H14), C16(H16), C18(H18),
 C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8379(6) 0.0800(10) 0.6536(3) 0.055(4) Uani 1 1 d . . . . .
O1 O 0.6877(5) 0.6629(8) 0.8168(2) 0.037(4) Uani 1 1 d . . . . .
N1 N 0.7688(6) 0.3845(10) 0.7381(3) 0.036(3) Uani 1 1 d . . . . .
C10 C 0.7101(7) 0.3051(11) 0.6022(3) 0.039(3) Uani 1 1 d . . . . .
C7 C 0.5745(7) 0.3492(10) 0.4829(3) 0.039(4) Uani 1 1 d . . . . .
C1 C 0.6936(7) 0.5545(10) 0.7521(3) 0.032(3) Uani 1 1 d . . . . .
C8 C 0.6528(8) 0.2102(12) 0.4715(4) 0.040(3) Uani 1 1 d . . . . .
H8 H 0.660259 0.132692 0.422751 0.049 Uiso 1 1 calc R U . . .
C2 C 0.6318(7) 0.5944(10) 0.6914(3) 0.031(3) Uani 1 1 d . . . . .
C9 C 0.7162(8) 0.1865(11) 0.5280(4) 0.040(4) Uani 1 1 d . . . . .
H9 H 0.765104 0.088643 0.517203 0.047 Uiso 1 1 calc R U . . .
C5 C 0.4925(7) 0.6369(10) 0.5744(3) 0.034(3) Uani 1 1 d . . . . .
C11 C 0.7739(7) 0.2505(11) 0.6622(4) 0.039(3) Uani 1 1 d . . . . .
C15 C 0.8907(9) 0.1891(13) 0.9238(4) 0.043(4) Uani 1 1 d . U . . .
H15 H 0.883796 0.090940 0.971196 0.052 Uiso 1 1 calc R U . . .
C4 C 0.4932(7) 0.7829(11) 0.6482(3) 0.032(3) Uani 1 1 d . . . . .
H4 H 0.446369 0.899671 0.659523 0.038 Uiso 1 1 calc R U . . .
C12 C 0.6343(7) 0.4627(10) 0.6153(3) 0.034(3) Uani 1 1 d . . . . .
C3 C 0.5562(7) 0.7656(10) 0.7030(3) 0.030(3) Uani 1 1 d . . . . .
H3 H 0.551407 0.867844 0.750530 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5698(7) 0.4863(10) 0.5588(3) 0.033(3) Uani 1 1 d . . . . .
C13 C 0.8363(8) 0.3579(11) 0.7977(4) 0.037(4) Uani 1 1 d . U . . .
C14 C 0.8284(8) 0.2051(12) 0.8694(4) 0.041(4) Uani 1 1 d . U . . .
H14 H 0.778328 0.113708 0.878507 0.049 Uiso 1 1 calc R U . . .
C16 C 0.9680(8) 0.3186(14) 0.9114(4) 0.050(4) Uani 1 1 d . U . . .
H16 H 1.012337 0.300814 0.949617 0.060 Uiso 1 1 calc R U . . .
C18 C 0.9099(9) 0.4942(12) 0.7846(4) 0.041(4) Uani 1 1 d . U . . .
H18 H 0.915267 0.601610 0.737649 0.049 Uiso 1 1 calc R U . . .
C17 C 0.9760(9) 0.4731(13) 0.8408(4) 0.045(4) Uani 1 1 d . U . . .
H17 H 1.026106 0.562464 0.831302 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
O2 C11 1.252(12) . ?
O1 C1 1.225(5) . ?
N1 C1 1.441(13) . ?
N1 C11 1.440(6) . ?
N1 C13 1.432(18) . ?
C10 C9 1.395(6) . ?
C10 C11 1.406(18) . ?
C10 C12 1.430(14) . ?
C7 C8 1.435(16) . ?
C7 C5 1.400(18) 3_666 ?
C7 C6 1.439(5) . ?
C1 C2 1.387(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.35(2) . ?
C2 C12 1.432(5) . ?
C2 C3 1.437(14) . ?
C9 H9 0.9300 . ?
C5 C4 1.403(6) . ?
C5 C6 1.457(14) . ?
C15 H15 0.9300 . ?
C15 C14 1.31(2) . ?
C15 C16 1.414(18) . ?
C4 H4 0.9300 . ?
C4 C3 1.326(17) . ?
C12 C6 1.363(18) . ?
C3 H3 0.9300 . ?
C13 C14 1.402(6) . ?
C13 C18 1.367(18) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.389(7) . ?
C18 H18 0.9300 . ?
C18 C17 1.38(2) . ?
C17 H17 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
C11 N1 C1 117.8(10) . . ?
C13 N1 C1 120.8(4) . . ?
C13 N1 C11 121.4(9) . . ?
C9 C10 C11 121.4(9) . . ?
C9 C10 C12 116.9(10) . . ?
C11 C10 C12 121.5(4) . . ?
C8 C7 C6 114.7(11) . . ?
C5 C7 C8 123.9(4) 3_666 . ?
C5 C7 C6 121.4(9) 3_666 . ?
O1 C1 N1 118.6(9) . . ?
O1 C1 C2 122.8(9) . . ?
C2 C1 N1 118.6(4) . . ?
C7 C8 H8 118.4 . . ?
C9 C8 C7 123.2(4) . . ?
C9 C8 H8 118.4 . . ?
C1 C2 C12 125.3(8) . . ?
C1 C2 C3 120.2(4) . . ?
C12 C2 C3 114.4(9) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 C10 121.6(10) . . ?
C8 C9 H9 119.2 . . ?
C7 C5 C4 124.3(9) 3_666 . ?
C7 C5 C6 120.7(4) 3_666 . ?
C4 C5 C6 114.8(10) . . ?
O2 C11 N1 115.9(10) . . ?
O2 C11 C10 122.7(4) . . ?
C10 C11 N1 121.4(9) . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 121.1(5) . . ?
C16 C15 H15 119.5 . . ?
C5 C4 H4 117.8 . . ?
C3 C4 C5 124.4(9) . . ?
C3 C4 H4 117.8 . . ?
C10 C12 C2 115.0(9) . . ?
C6 C12 C10 121.9(4) . . ?
C6 C12 C2 123.1(8) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.3(4) . . ?
C4 C3 H3 118.8 . . ?
C7 C6 C5 117.9(10) . . ?
C12 C6 C7 121.5(9) . . ?
C12 C6 C5 120.6(4) . . ?
C14 C13 N1 121.7(11) . . ?
C18 C13 N1 118.9(5) . . ?
C18 C13 C14 119.4(12) . . ?
C15 C14 C13 120.9(12) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C15 C16 H16 120.9 . . ?
C17 C16 C15 118.2(12) . . ?
C17 C16 H16 120.9 . . ?
C13 C18 H18 119.9 . . ?
C13 C18 C17 120.3(5) . . ?
C17 C18 H18 119.9 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.1(12) . . ?
C18 C17 H17 119.9 . . ?

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
O1 C1 C2 C12 -177.9(4) . . . . ?
O1 C1 C2 C3 -0.6(8) . . . . ?
N1 C1 C2 C12 3.3(8) . . . . ?
N1 C1 C2 C3 -179.5(4) . . . . ?
N1 C13 C14 C15 -178.8(5) . . . . ?
N1 C13 C18 C17 180.0(4) . . . . ?
C10 C12 C6 C7 0.7(7) . . . . ?
C10 C12 C6 C5 178.0(4) . . . . ?
C7 C8 C9 C10 -1.4(8) . . . . ?
C7 C5 C4 C3 179.0(5) 3_666 . . . ?
C7 C5 C6 C7 -0.7(7) 3_666 . . . ?
C7 C5 C6 C12 -178.0(5) 3_666 . . . ?
C1 N1 C11 O2 -175.0(4) . . . . ?
C1 N1 C11 C10 4.1(8) . . . . ?
C1 N1 C13 C14 51.1(6) . . . . ?
C1 N1 C13 C18 -127.2(5) . . . . ?
C1 C2 C12 C10 -5.0(7) . . . . ?
C1 C2 C12 C6 175.5(5) . . . . ?
C1 C2 C3 C4 -174.5(5) . . . . ?
C8 C7 C6 C5 179.2(3) . . . . ?
C8 C7 C6 C12 -3.5(6) . . . . ?
C2 C12 C6 C7 -179.7(4) . . . . ?
C2 C12 C6 C5 -2.5(7) . . . . ?
C9 C10 C11 O2 -3.1(9) . . . . ?
C9 C10 C11 N1 177.8(5) . . . . ?
C9 C10 C12 C2 -177.6(4) . . . . ?
C9 C10 C12 C6 2.0(7) . . . . ?
C5 C7 C8 C9 -177.7(5) 3_666 . . . ?
C5 C7 C6 C5 0.7(7) 3_666 . . . ?
C5 C7 C6 C12 178.0(5) 3_666 . . . ?
C5 C4 C3 C2 0.5(8) . . . . ?
C11 N1 C1 O1 178.5(4) . . . . ?
C11 N1 C1 C2 -2.6(7) . . . . ?
C11 N1 C13 C14 -130.3(5) . . . . ?
C11 N1 C13 C18 51.4(6) . . . . ?
C11 C10 C9 C8 174.5(6) . . . . ?
C11 C10 C12 C2 6.2(7) . . . . ?
C11 C10 C12 C6 -174.2(5) . . . . ?
C15 C16 C17 C18 -0.6(7) . . . . ?
C4 C5 C6 C7 -176.9(3) . . . . ?
C4 C5 C6 C12 5.7(6) . . . . ?
C12 C10 C9 C8 -1.6(8) . . . . ?
C12 C10 C11 O2 172.8(5) . . . . ?
C12 C10 C11 N1 -6.2(8) . . . . ?
C12 C2 C3 C4 3.0(7) . . . . ?
C3 C2 C12 C10 177.7(4) . . . . ?
C3 C2 C12 C6 -1.9(7) . . . . ?
C6 C7 C8 C9 3.9(7) . . . . ?
C6 C5 C4 C3 -4.9(7) . . . . ?
C13 N1 C1 O1 -2.8(7) . . . . ?
C13 N1 C1 C2 176.1(5) . . . . ?
C13 N1 C11 O2 6.4(8) . . . . ?
C13 N1 C11 C10 -174.6(5) . . . . ?
C13 C18 C17 C16 -1.0(8) . . . . ?
C14 C15 C16 C17 1.7(7) . . . . ?
C14 C13 C18 C17 1.6(7) . . . . ?
C16 C15 C14 C13 -1.2(8) . . . . ?
C18 C13 C14 C15 -0.4(7) . . . . ?

_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
;
####################################################################### 
# 
# 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_PTCDI_Ph_2_85GPa
_database_code_depnum_ccdc_archive 'CCDC 2253192'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PTCDI_Ph_2_85GPa    
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.354 Why?  
RESPONSE: These data come from high-pressure experiment and part of the 
reflection cannot be collected, due to the DAC opening angle, and the 
measurement strategy. 
;
_vrf_PLAT088_PTCDI_Ph_2_85GPa    
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.74 Note  
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber.
;
_vrf_PLAT340_PTCDI_Ph_2_85GPa    
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.01375 Ang.   
RESPONSE: These data comes from high-pressure experiment and part of the reflection 
cannot be collected, affecting bond precision. In addition, despite multiple attempts 
to grow better diffracting crystals, it was not successful.
;
_vrf_PLAT911_PTCDI_Ph_2_85GPa    
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        996 Report
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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 -0.0011 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N -0.0016 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0014 0.0018 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.644(13)
_cell_length_b                   3.5187(2)
_cell_length_c                   17.670(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.14(4)
_cell_angle_gamma                90
_cell_volume                     1024.5(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    385
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.8260
_cell_measurement_theta_min      2.6830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.048
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.95a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 0.354
_diffrn_reflns_Laue_measured_fraction_max 0.242
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            2258
_diffrn_reflns_point_group_measured_fraction_full 0.354
_diffrn_reflns_point_group_measured_fraction_max 0.242
_diffrn_reflns_theta_full        14.237
_diffrn_reflns_theta_max         20.474
_diffrn_reflns_theta_min         2.680
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_detector_type            'Eiger 9M CdTe'
_diffrn_measured_fraction_theta_full 0.354
_diffrn_measured_fraction_theta_max 0.242
_diffrn_measurement_details      
;
 Data were collected at room temperature and pressure of 2.85(2) GPa
 Pressure was determined by monitoring the shift of 
 the ruby R1-fluorescence line.
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'esperanto-CrysAlisPro-abstract goniometer imported esperanto images'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_suport 'diamond anvil cell'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.40989
_diffrn_source                   'undulator, ID15B, ESRF'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                544
_reflns_number_total             1280
_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 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.95a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1280
_refine_ls_number_restraints     222
_refine_ls_R_factor_all          0.1360
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      0.882
_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)+(0.1296P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.2324
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C14, C13, C18, C17, C16, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(N1) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C8) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(C7) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C15) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C14, C13, C18, C17, C16, C15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N1, C1, C2, C12, C10, C11, O2, O1, C3, C4, C5, C6, C7, C8, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C15(H15), C4(H4), C3(H3), C14(H14), C16(H16), C18(H18),
 C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8398(6) 0.0843(10) 0.6535(3) 0.053(3) Uani 1 1 d . . . . .
O1 O 0.6877(5) 0.6710(8) 0.8173(2) 0.043(4) Uani 1 1 d . . . . .
N1 N 0.7683(7) 0.3878(11) 0.7378(3) 0.040(3) Uani 1 1 d . U . . .
C10 C 0.7112(7) 0.3093(11) 0.6021(3) 0.034(2) Uani 1 1 d . U . . .
C7 C 0.5745(8) 0.3508(11) 0.4825(3) 0.035(3) Uani 1 1 d . U . . .
C1 C 0.6937(8) 0.5604(11) 0.7523(4) 0.034(3) Uani 1 1 d . . . . .
C8 C 0.6522(8) 0.2123(12) 0.4704(4) 0.039(2) Uani 1 1 d . U . . .
H8 H 0.659544 0.134316 0.421599 0.046 Uiso 1 1 calc R U . . .
C2 C 0.6323(7) 0.5986(11) 0.6914(3) 0.034(3) Uani 1 1 d . . . . .
C9 C 0.7153(8) 0.1899(11) 0.5270(3) 0.037(2) Uani 1 1 d . U . . .
H9 H 0.764007 0.090251 0.515773 0.044 Uiso 1 1 calc R U . . .
C5 C 0.4940(8) 0.6428(11) 0.5750(3) 0.033(3) Uani 1 1 d . . . . .
C11 C 0.7742(8) 0.2530(13) 0.6622(3) 0.039(3) Uani 1 1 d . . . . .
C15 C 0.8915(9) 0.1889(14) 0.9247(4) 0.047(3) Uani 1 1 d . U . . .
H15 H 0.885306 0.089258 0.972279 0.056 Uiso 1 1 calc R U . . .
C4 C 0.4937(8) 0.7888(11) 0.6487(3) 0.035(3) Uani 1 1 d . . . . .
H4 H 0.446503 0.904223 0.659916 0.042 Uiso 1 1 calc R U . . .
C12 C 0.6348(8) 0.4676(11) 0.6152(3) 0.035(2) Uani 1 1 d . . . . .
C3 C 0.5565(8) 0.7716(11) 0.7028(4) 0.035(2) Uani 1 1 d . U . . .
H3 H 0.551791 0.875263 0.750339 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5696(8) 0.4883(11) 0.5583(3) 0.035(2) Uani 1 1 d . U . . .
C13 C 0.8359(9) 0.3639(12) 0.7977(4) 0.035(4) Uani 1 1 d . U . . .
C14 C 0.8278(9) 0.2073(12) 0.8696(4) 0.040(3) Uani 1 1 d . U . . .
H14 H 0.777682 0.115866 0.878733 0.048 Uiso 1 1 calc R U . . .
C16 C 0.9672(8) 0.3184(13) 0.9111(4) 0.049(3) Uani 1 1 d . U . . .
H16 H 1.011993 0.299264 0.948884 0.059 Uiso 1 1 calc R U . . .
C18 C 0.9087(10) 0.4985(13) 0.7839(4) 0.040(4) Uani 1 1 d . U . . .
H18 H 0.913935 0.605012 0.736716 0.048 Uiso 1 1 calc R U . . .
C17 C 0.9752(10) 0.4766(13) 0.8405(4) 0.044(4) Uani 1 1 d . U . . .
H17 H 1.025284 0.568089 0.831251 0.052 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
O2 C11 1.271(13) . ?
O1 C1 1.231(5) . ?
N1 C1 1.438(15) . ?
N1 C11 1.433(6) . ?
N1 C13 1.435(19) . ?
C10 C9 1.402(6) . ?
C10 C11 1.397(17) . ?
C10 C12 1.437(15) . ?
C7 C8 1.426(17) . ?
C7 C5 1.415(18) 3_666 ?
C7 C6 1.437(5) . ?
C1 C2 1.381(18) . ?
C8 H8 0.9300 . ?
C8 C9 1.346(18) . ?
C2 C12 1.429(6) . ?
C2 C3 1.441(16) . ?
C9 H9 0.9300 . ?
C5 C4 1.400(6) . ?
C5 C6 1.440(16) . ?
C15 H15 0.9300 . ?
C15 C14 1.34(2) . ?
C15 C16 1.392(18) . ?
C4 H4 0.9300 . ?
C4 C3 1.314(18) . ?
C12 C6 1.373(18) . ?
C3 H3 0.9300 . ?
C13 C14 1.407(6) . ?
C13 C18 1.35(2) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.389(7) . ?
C18 H18 0.9300 . ?
C18 C17 1.38(2) . ?
C17 H17 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
C11 N1 C1 118.7(10) . . ?
C11 N1 C13 121.2(9) . . ?
C13 N1 C1 120.0(5) . . ?
C9 C10 C12 115.6(10) . . ?
C11 C10 C9 123.1(9) . . ?
C11 C10 C12 121.2(5) . . ?
C8 C7 C6 115.2(11) . . ?
C5 C7 C8 123.6(5) 3_666 . ?
C5 C7 C6 121.1(11) 3_666 . ?
O1 C1 N1 119.1(11) . . ?
O1 C1 C2 123.3(10) . . ?
C2 C1 N1 117.7(4) . . ?
C7 C8 H8 118.7 . . ?
C9 C8 C7 122.6(5) . . ?
C9 C8 H8 118.7 . . ?
C1 C2 C12 125.8(9) . . ?
C1 C2 C3 119.9(5) . . ?
C12 C2 C3 114.2(10) . . ?
C10 C9 H9 118.4 . . ?
C8 C9 C10 123.2(10) . . ?
C8 C9 H9 118.4 . . ?
C7 C5 C6 119.9(5) 3_666 . ?
C4 C5 C7 123.5(10) . 3_666 ?
C4 C5 C6 116.6(11) . . ?
O2 C11 N1 116.1(10) . . ?
O2 C11 C10 122.6(5) . . ?
C10 C11 N1 121.3(9) . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.1(5) . . ?
C16 C15 H15 119.9 . . ?
C5 C4 H4 118.3 . . ?
C3 C4 C5 123.5(10) . . ?
C3 C4 H4 118.3 . . ?
C2 C12 C10 114.9(10) . . ?
C6 C12 C10 121.9(5) . . ?
C6 C12 C2 123.2(9) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 C2 122.7(5) . . ?
C4 C3 H3 118.6 . . ?
C7 C6 C5 119.0(12) . . ?
C12 C6 C7 121.5(10) . . ?
C12 C6 C5 119.6(5) . . ?
C14 C13 N1 121.6(12) . . ?
C18 C13 N1 118.3(5) . . ?
C18 C13 C14 120.1(13) . . ?
C15 C14 C13 120.6(12) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.3(12) . . ?
C17 C16 H16 120.3 . . ?
C13 C18 H18 120.2 . . ?
C13 C18 C17 119.6(6) . . ?
C17 C18 H18 120.2 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.2(12) . . ?
C18 C17 H17 119.9 . . ?

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
O1 C1 C2 C12 -178.3(5) . . . . ?
O1 C1 C2 C3 -0.7(9) . . . . ?
N1 C1 C2 C12 2.7(8) . . . . ?
N1 C1 C2 C3 -179.7(5) . . . . ?
N1 C13 C14 C15 -179.8(5) . . . . ?
N1 C13 C18 C17 -179.5(5) . . . . ?
C10 C12 C6 C7 0.2(8) . . . . ?
C10 C12 C6 C5 178.8(4) . . . . ?
C7 C8 C9 C10 -1.8(8) . . . . ?
C7 C5 C4 C3 177.7(5) 3_666 . . . ?
C7 C5 C6 C7 1.4(7) 3_666 . . . ?
C7 C5 C6 C12 -177.2(5) 3_666 . . . ?
C1 N1 C11 O2 -176.3(5) . . . . ?
C1 N1 C11 C10 4.3(8) . . . . ?
C1 N1 C13 C14 52.2(6) . . . . ?
C1 N1 C13 C18 -127.5(6) . . . . ?
C1 C2 C12 C10 -4.9(8) . . . . ?
C1 C2 C12 C6 174.9(6) . . . . ?
C1 C2 C3 C4 -174.5(6) . . . . ?
C8 C7 C6 C5 178.4(4) . . . . ?
C8 C7 C6 C12 -3.0(7) . . . . ?
C2 C12 C6 C7 -179.6(4) . . . . ?
C2 C12 C6 C5 -1.0(8) . . . . ?
C9 C10 C11 O2 -0.9(9) . . . . ?
C9 C10 C11 N1 178.5(5) . . . . ?
C9 C10 C12 C2 -178.2(4) . . . . ?
C9 C10 C12 C6 2.0(7) . . . . ?
C5 C7 C8 C9 -176.3(5) 3_666 . . . ?
C5 C7 C6 C5 -1.5(7) 3_666 . . . ?
C5 C7 C6 C12 177.1(5) 3_666 . . . ?
C5 C4 C3 C2 -0.1(9) . . . . ?
C11 N1 C1 O1 178.8(5) . . . . ?
C11 N1 C1 C2 -2.2(7) . . . . ?
C11 N1 C13 C14 -129.8(6) . . . . ?
C11 N1 C13 C18 50.5(6) . . . . ?
C11 C10 C9 C8 173.7(6) . . . . ?
C11 C10 C12 C2 6.7(7) . . . . ?
C11 C10 C12 C6 -173.1(6) . . . . ?
C15 C16 C17 C18 -1.2(7) . . . . ?
C4 C5 C6 C7 -177.1(4) . . . . ?
C4 C5 C6 C12 4.3(7) . . . . ?
C12 C10 C9 C8 -1.3(7) . . . . ?
C12 C10 C11 O2 173.9(5) . . . . ?
C12 C10 C11 N1 -6.8(9) . . . . ?
C12 C2 C3 C4 3.4(7) . . . . ?
C3 C2 C12 C10 177.4(4) . . . . ?
C3 C2 C12 C6 -2.8(8) . . . . ?
C6 C7 C8 C9 3.8(7) . . . . ?
C6 C5 C4 C3 -3.8(8) . . . . ?
C13 N1 C1 O1 -3.2(7) . . . . ?
C13 N1 C1 C2 175.8(6) . . . . ?
C13 N1 C11 O2 5.7(8) . . . . ?
C13 N1 C11 C10 -173.7(6) . . . . ?
C13 C18 C17 C16 -0.2(8) . . . . ?
C14 C15 C16 C17 1.8(7) . . . . ?
C14 C13 C18 C17 0.8(7) . . . . ?
C16 C15 C14 C13 -1.2(8) . . . . ?
C18 C13 C14 C15 -0.1(7) . . . . ?

_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
;
####################################################################### 
# 
# 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_PTCDI_Ph_130K
_database_code_depnum_ccdc_archive 'CCDC 2253193'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PTCDI_Ph_130K       
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      55.00 Degree
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_RINTA01_PTCDI_Ph_130K       
;
PROBLEM: The value of Rint is greater than 0.18
            Rint given   0.194
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_PLAT020_PTCDI_Ph_130K       
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.194 Report
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_PLAT026_PTCDI_Ph_130K       
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        35% Check 
RESPONSE: This low value comes from the overall poor diffraction quality of the 
crystal.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-03-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.755(5)
_cell_length_b                   3.9243(13)
_cell_length_c                   18.288(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.69(2)
_cell_angle_gamma                90
_cell_volume                     1188.7(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    391
_cell_measurement_temperature    129.8(3)
_cell_measurement_theta_max      63.9430
_cell_measurement_theta_min      2.6540
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.878
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -3 -1 0.0543
0 0 12 0.0089
0 0 -12 0.0287
11 0 -1 0.0708
-1 2 -2 0.0708
-11 0 1 0.0208

_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1939
_diffrn_reflns_av_unetI/netI     0.2231
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4469
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        55.000
_diffrn_reflns_theta_max         73.904
_diffrn_reflns_theta_min         2.668
_diffrn_ambient_temperature      130.15
_diffrn_detector_area_resol_mean 10.5384
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
 Data were collected at temperature of 130 K
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                800
_reflns_number_total             2316
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2235
_refine_ls_R_factor_gt           0.0901
_refine_ls_restrained_S_all      0.948
_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)+(0.0274P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1656
_refine_ls_wR_factor_ref         0.2472
_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:
 C8(H3), C9(H4), C15(H6), C4(H2), C3(H1), C14(H5), C16(H7), C18(H9), C17(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8306(3) 0.0508(13) 0.6565(2) 0.0393(13) Uani 1 1 d . . . . .
O1 O 0.6853(2) 0.6116(12) 0.8123(2) 0.0360(12) Uani 1 1 d . . . . .
N1 N 0.7615(3) 0.3451(14) 0.7346(2) 0.0280(13) Uani 1 1 d . . . . .
C10 C 0.7035(4) 0.2659(17) 0.6041(3) 0.0299(16) Uani 1 1 d . . . . .
C7 C 0.5750(3) 0.3389(17) 0.4865(3) 0.0279(15) Uani 1 1 d . . . . .
C1 C 0.6918(3) 0.5084(18) 0.7502(3) 0.0313(17) Uani 1 1 d . . . . .
C8 C 0.6470(3) 0.1936(17) 0.4762(3) 0.0319(16) Uani 1 1 d . . . . .
H3 H 0.653464 0.117918 0.428132 0.038 Uiso 1 1 calc R U . . .
C2 C 0.6249(3) 0.5492(17) 0.6883(3) 0.0262(15) Uani 1 1 d . . . . .
C9 C 0.7107(4) 0.1532(17) 0.5337(3) 0.0309(16) Uani 1 1 d . . . . .
H4 H 0.759307 0.047909 0.524694 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4939(3) 0.6277(17) 0.5734(3) 0.0284(16) Uani 1 1 d . . . . .
C11 C 0.7703(4) 0.2113(18) 0.6649(3) 0.0306(16) Uani 1 1 d . . . . .
C15 C 0.8872(4) 0.161(2) 0.9162(4) 0.044(2) Uani 1 1 d . . . . .
H6 H 0.882047 0.059071 0.962364 0.053 Uiso 1 1 calc R U . . .
C4 C 0.4904(4) 0.7480(16) 0.6434(3) 0.0302(16) Uani 1 1 d . . . . .
H2 H 0.442736 0.857666 0.653544 0.036 Uiso 1 1 calc R U . . .
C12 C 0.6326(3) 0.4228(17) 0.6168(3) 0.0273(15) Uani 1 1 d . . . . .
C3 C 0.5558(4) 0.7115(18) 0.6999(3) 0.0335(17) Uani 1 1 d . . . . .
H1 H 0.552187 0.801567 0.747458 0.040 Uiso 1 1 calc R U . . .
C6 C 0.5652(3) 0.4606(16) 0.5583(3) 0.0253(15) Uani 1 1 d . . . . .
C13 C 0.8307(4) 0.3214(19) 0.7939(3) 0.0351(17) Uani 1 1 d . . . . .
C14 C 0.8213(4) 0.1687(18) 0.8609(3) 0.0359(17) Uani 1 1 d . . . . .
H5 H 0.771095 0.072664 0.868225 0.043 Uiso 1 1 calc R U . . .
C16 C 0.9607(4) 0.3000(19) 0.9056(4) 0.0401(19) Uani 1 1 d . . . . .
H7 H 1.005348 0.292187 0.944324 0.048 Uiso 1 1 calc R U . . .
C18 C 0.9028(4) 0.4652(18) 0.7828(3) 0.0358(17) Uani 1 1 d . . . . .
H9 H 0.907279 0.574257 0.737186 0.043 Uiso 1 1 calc R U . . .
C17 C 0.9692(4) 0.4502(18) 0.8385(3) 0.0401(18) Uani 1 1 d . . . . .
H8 H 1.019676 0.541965 0.830787 0.048 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
O2 C11 1.219(7) . ?
O1 C1 1.225(6) . ?
N1 C1 1.400(7) . ?
N1 C11 1.407(7) . ?
N1 C13 1.465(7) . ?
C10 C9 1.382(7) . ?
C10 C11 1.470(8) . ?
C10 C12 1.390(8) . ?
C7 C8 1.373(8) . ?
C7 C5 1.471(8) 3_666 ?
C7 C6 1.429(7) . ?
C1 C2 1.477(8) . ?
C8 H3 0.9500 . ?
C8 C9 1.390(8) . ?
C2 C12 1.421(7) . ?
C2 C3 1.365(8) . ?
C9 H4 0.9500 . ?
C5 C4 1.375(7) . ?
C5 C6 1.426(8) . ?
C15 H6 0.9500 . ?
C15 C14 1.380(8) . ?
C15 C16 1.387(9) . ?
C4 H2 0.9500 . ?
C4 C3 1.394(8) . ?
C12 C6 1.441(8) . ?
C3 H1 0.9500 . ?
C13 C14 1.394(8) . ?
C13 C18 1.376(9) . ?
C14 H5 0.9500 . ?
C16 H7 0.9500 . ?
C16 C17 1.387(9) . ?
C18 H9 0.9500 . ?
C18 C17 1.392(8) . ?
C17 H8 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 124.1(5) . . ?
C1 N1 C13 118.1(5) . . ?
C11 N1 C13 117.8(5) . . ?
C9 C10 C11 119.6(5) . . ?
C9 C10 C12 119.6(6) . . ?
C12 C10 C11 120.7(5) . . ?
C8 C7 C5 122.8(6) . 3_666 ?
C8 C7 C6 119.3(5) . . ?
C6 C7 C5 117.9(5) . 3_666 ?
O1 C1 N1 122.2(5) . . ?
O1 C1 C2 120.8(6) . . ?
N1 C1 C2 117.0(5) . . ?
C7 C8 H3 118.9 . . ?
C7 C8 C9 122.3(6) . . ?
C9 C8 H3 118.9 . . ?
C12 C2 C1 120.2(5) . . ?
C3 C2 C1 119.6(5) . . ?
C3 C2 C12 120.2(5) . . ?
C10 C9 C8 120.2(6) . . ?
C10 C9 H4 119.9 . . ?
C8 C9 H4 119.9 . . ?
C4 C5 C7 121.7(6) . 3_666 ?
C4 C5 C6 119.5(6) . . ?
C6 C5 C7 118.8(5) . 3_666 ?
O2 C11 N1 120.6(5) . . ?
O2 C11 C10 122.0(6) . . ?
N1 C11 C10 117.4(5) . . ?
C14 C15 H6 119.4 . . ?
C14 C15 C16 121.2(7) . . ?
C16 C15 H6 119.4 . . ?
C5 C4 H2 119.5 . . ?
C5 C4 C3 121.0(6) . . ?
C3 C4 H2 119.5 . . ?
C10 C12 C2 120.5(5) . . ?
C10 C12 C6 121.0(5) . . ?
C2 C12 C6 118.5(5) . . ?
C2 C3 C4 121.5(6) . . ?
C2 C3 H1 119.2 . . ?
C4 C3 H1 119.2 . . ?
C7 C6 C12 117.6(5) . . ?
C5 C6 C7 123.1(5) . . ?
C5 C6 C12 119.3(5) . . ?
C14 C13 N1 119.7(6) . . ?
C18 C13 N1 118.6(6) . . ?
C18 C13 C14 121.6(6) . . ?
C15 C14 C13 118.0(6) . . ?
C15 C14 H5 121.0 . . ?
C13 C14 H5 121.0 . . ?
C15 C16 H7 119.9 . . ?
C17 C16 C15 120.1(6) . . ?
C17 C16 H7 119.9 . . ?
C13 C18 H9 120.1 . . ?
C13 C18 C17 119.8(6) . . ?
C17 C18 H9 120.1 . . ?
C16 C17 C18 119.3(7) . . ?
C16 C17 H8 120.4 . . ?
C18 C17 H8 120.4 . . ?

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
O1 C1 C2 C12 -178.8(6) . . . . ?
O1 C1 C2 C3 1.7(10) . . . . ?
N1 C1 C2 C12 0.5(9) . . . . ?
N1 C1 C2 C3 -179.0(6) . . . . ?
N1 C13 C14 C15 -177.9(6) . . . . ?
N1 C13 C18 C17 179.1(6) . . . . ?
C10 C12 C6 C7 -1.6(9) . . . . ?
C10 C12 C6 C5 -179.1(6) . . . . ?
C7 C8 C9 C10 -1.1(10) . . . . ?
C7 C5 C4 C3 179.3(6) 3_666 . . . ?
C7 C5 C6 C7 3.5(11) 3_666 . . . ?
C7 C5 C6 C12 -179.2(6) 3_666 . . . ?
C1 N1 C11 O2 -174.7(7) . . . . ?
C1 N1 C11 C10 3.7(10) . . . . ?
C1 N1 C13 C14 56.4(9) . . . . ?
C1 N1 C13 C18 -120.7(7) . . . . ?
C1 C2 C12 C10 -1.3(10) . . . . ?
C1 C2 C12 C6 178.6(6) . . . . ?
C1 C2 C3 C4 -178.4(6) . . . . ?
C8 C7 C6 C5 177.3(6) . . . . ?
C8 C7 C6 C12 -0.1(9) . . . . ?
C2 C12 C6 C7 178.5(6) . . . . ?
C2 C12 C6 C5 1.1(9) . . . . ?
C9 C10 C11 O2 -4.5(11) . . . . ?
C9 C10 C11 N1 177.1(6) . . . . ?
C9 C10 C12 C2 -178.2(6) . . . . ?
C9 C10 C12 C6 2.0(10) . . . . ?
C5 C7 C8 C9 -177.8(6) 3_666 . . . ?
C5 C7 C6 C5 -3.4(11) 3_666 . . . ?
C5 C7 C6 C12 179.2(6) 3_666 . . . ?
C5 C4 C3 C2 -1.4(10) . . . . ?
C11 N1 C1 O1 177.5(6) . . . . ?
C11 N1 C1 C2 -1.9(9) . . . . ?
C11 N1 C13 C14 -125.5(7) . . . . ?
C11 N1 C13 C18 57.3(9) . . . . ?
C11 C10 C9 C8 178.0(6) . . . . ?
C11 C10 C12 C2 3.2(10) . . . . ?
C11 C10 C12 C6 -176.6(6) . . . . ?
C15 C16 C17 C18 1.1(11) . . . . ?
C4 C5 C6 C7 -177.7(6) . . . . ?
C4 C5 C6 C12 -0.4(9) . . . . ?
C12 C10 C9 C8 -0.6(10) . . . . ?
C12 C10 C11 O2 174.1(7) . . . . ?
C12 C10 C11 N1 -4.3(10) . . . . ?
C12 C2 C3 C4 2.1(10) . . . . ?
C3 C2 C12 C10 178.2(7) . . . . ?
C3 C2 C12 C6 -2.0(10) . . . . ?
C6 C7 C8 C9 1.4(10) . . . . ?
C6 C5 C4 C3 0.5(10) . . . . ?
C13 N1 C1 O1 -4.6(10) . . . . ?
C13 N1 C1 C2 176.0(6) . . . . ?
C13 N1 C11 O2 7.4(10) . . . . ?
C13 N1 C11 C10 -174.2(6) . . . . ?
C13 C18 C17 C16 -2.1(11) . . . . ?
C14 C15 C16 C17 0.1(11) . . . . ?
C14 C13 C18 C17 2.0(11) . . . . ?
C16 C15 C14 C13 -0.2(11) . . . . ?
C18 C13 C14 C15 -0.8(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
####################################################################### 
# 
# 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_PTCDI_Ph_150K
_database_code_depnum_ccdc_archive 'CCDC 2253194'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PTCDI_Ph_150K       
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      55.00 Degree
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_RINTA01_PTCDI_Ph_150K       
;
PROBLEM: The value of Rint is greater than 0.18
            Rint given   0.195
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_PLAT020_PTCDI_Ph_150K       
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.195 Report
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_PLAT026_PTCDI_Ph_150K       
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        32% Check 
RESPONSE: This low value comes from the overall poor diffraction quality of the 
crystal.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-03-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.749(4)
_cell_length_b                   3.9271(12)
_cell_length_c                   18.296(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.74(2)
_cell_angle_gamma                90
_cell_volume                     1189.4(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    397
_cell_measurement_temperature    149.9(3)
_cell_measurement_theta_max      66.8370
_cell_measurement_theta_min      2.6480
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -3 -1 0.0543
0 0 12 0.0089
0 0 -12 0.0287
11 0 -1 0.0708
-1 2 -2 0.0708
-11 0 1 0.0208

_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1946
_diffrn_reflns_av_unetI/netI     0.2206
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4510
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        55.000
_diffrn_reflns_theta_max         73.595
_diffrn_reflns_theta_min         2.669
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.5384
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
 Data were collected at temperature of 150 K
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                749
_reflns_number_total             2320
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2152
_refine_ls_R_factor_gt           0.0804
_refine_ls_restrained_S_all      0.917
_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)+(0.0150P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.2344
_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:
 C8(H3), C9(H4), C15(H6), C4(H2), C3(H1), C14(H5), C16(H7), C18(H9), C17(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8307(2) 0.0529(13) 0.6564(2) 0.0442(13) Uani 1 1 d . . . . .
O1 O 0.6851(2) 0.6084(12) 0.8121(2) 0.0375(11) Uani 1 1 d . . . . .
N1 N 0.7613(3) 0.3455(15) 0.7350(2) 0.0334(13) Uani 1 1 d . . . . .
C10 C 0.7031(3) 0.2659(17) 0.6041(3) 0.0308(16) Uani 1 1 d . . . . .
C7 C 0.5755(3) 0.3411(17) 0.4866(3) 0.0313(15) Uani 1 1 d . . . . .
C1 C 0.6924(3) 0.5077(16) 0.7503(3) 0.0307(15) Uani 1 1 d . . . . .
C8 C 0.6465(3) 0.1928(17) 0.4766(3) 0.0351(17) Uani 1 1 d . . . . .
H3 H 0.652500 0.113484 0.428675 0.042 Uiso 1 1 calc R U . . .
C2 C 0.6246(3) 0.5483(16) 0.6881(3) 0.0277(14) Uani 1 1 d . . . . .
C9 C 0.7105(4) 0.1530(17) 0.5341(3) 0.0355(16) Uani 1 1 d . . . . .
H4 H 0.759259 0.048391 0.525090 0.043 Uiso 1 1 calc R U . . .
C5 C 0.4943(3) 0.6245(16) 0.5729(3) 0.0282(14) Uani 1 1 d . . . . .
C11 C 0.7707(3) 0.2116(17) 0.6650(3) 0.0327(16) Uani 1 1 d . . . . .
C15 C 0.8876(4) 0.1610(19) 0.9161(3) 0.0453(19) Uani 1 1 d . . . . .
H6 H 0.882327 0.059505 0.962206 0.054 Uiso 1 1 calc R U . . .
C4 C 0.4908(3) 0.7474(17) 0.6434(3) 0.0338(16) Uani 1 1 d . . . . .
H2 H 0.443207 0.858846 0.653239 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6322(3) 0.4244(17) 0.6162(3) 0.0302(15) Uani 1 1 d . . . . .
C3 C 0.5559(3) 0.7103(18) 0.7002(3) 0.0336(16) Uani 1 1 d . . . . .
H1 H 0.552254 0.798950 0.747937 0.040 Uiso 1 1 calc R U . . .
C6 C 0.5659(3) 0.4616(17) 0.5578(3) 0.0307(16) Uani 1 1 d . . . . .
C13 C 0.8306(3) 0.3243(18) 0.7936(3) 0.0327(16) Uani 1 1 d . . . . .
C14 C 0.8217(4) 0.1682(18) 0.8596(3) 0.0402(17) Uani 1 1 d . . . . .
H5 H 0.771746 0.067902 0.866309 0.048 Uiso 1 1 calc R U . . .
C16 C 0.9603(4) 0.3000(19) 0.9053(4) 0.0464(19) Uani 1 1 d . . . . .
H7 H 1.004975 0.293376 0.944127 0.056 Uiso 1 1 calc R U . . .
C18 C 0.9032(4) 0.4641(18) 0.7827(3) 0.0388(17) Uani 1 1 d . . . . .
H9 H 0.908270 0.570315 0.736953 0.047 Uiso 1 1 calc R U . . .
C17 C 0.9689(4) 0.4487(19) 0.8389(4) 0.0451(19) Uani 1 1 d . . . . .
H8 H 1.019556 0.540336 0.831469 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
O2 C11 1.212(7) . ?
O1 C1 1.222(6) . ?
N1 C1 1.384(7) . ?
N1 C11 1.416(7) . ?
N1 C13 1.458(7) . ?
C10 C9 1.380(7) . ?
C10 C11 1.478(8) . ?
C10 C12 1.388(8) . ?
C7 C8 1.360(8) . ?
C7 C5 1.478(7) 3_666 ?
C7 C6 1.418(7) . ?
C1 C2 1.489(8) . ?
C8 H3 0.9500 . ?
C8 C9 1.393(8) . ?
C2 C12 1.426(7) . ?
C2 C3 1.363(8) . ?
C9 H4 0.9500 . ?
C5 C4 1.387(7) . ?
C5 C6 1.424(8) . ?
C15 H6 0.9500 . ?
C15 C14 1.392(8) . ?
C15 C16 1.376(9) . ?
C4 H2 0.9500 . ?
C4 C3 1.395(7) . ?
C12 C6 1.426(7) . ?
C3 H1 0.9500 . ?
C13 C14 1.381(8) . ?
C13 C18 1.376(8) . ?
C14 H5 0.9500 . ?
C16 H7 0.9500 . ?
C16 C17 1.376(9) . ?
C18 H9 0.9500 . ?
C18 C17 1.389(8) . ?
C17 H8 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 124.4(5) . . ?
C1 N1 C13 118.2(5) . . ?
C11 N1 C13 117.4(5) . . ?
C9 C10 C11 119.1(5) . . ?
C9 C10 C12 119.5(6) . . ?
C12 C10 C11 121.4(5) . . ?
C8 C7 C5 123.3(5) . 3_666 ?
C8 C7 C6 119.3(5) . . ?
C6 C7 C5 117.3(5) . 3_666 ?
O1 C1 N1 122.7(5) . . ?
O1 C1 C2 120.1(6) . . ?
N1 C1 C2 117.2(5) . . ?
C7 C8 H3 118.8 . . ?
C7 C8 C9 122.4(6) . . ?
C9 C8 H3 118.8 . . ?
C12 C2 C1 120.3(5) . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 C12 120.3(5) . . ?
C10 C9 C8 119.8(6) . . ?
C10 C9 H4 120.1 . . ?
C8 C9 H4 120.1 . . ?
C4 C5 C7 120.9(5) . 3_666 ?
C4 C5 C6 119.5(5) . . ?
C6 C5 C7 119.6(5) . 3_666 ?
O2 C11 N1 121.1(5) . . ?
O2 C11 C10 122.1(6) . . ?
N1 C11 C10 116.8(5) . . ?
C14 C15 H6 119.8 . . ?
C16 C15 H6 119.8 . . ?
C16 C15 C14 120.3(6) . . ?
C5 C4 H2 119.4 . . ?
C5 C4 C3 121.2(6) . . ?
C3 C4 H2 119.4 . . ?
C10 C12 C2 119.9(5) . . ?
C10 C12 C6 120.9(5) . . ?
C2 C12 C6 119.2(5) . . ?
C2 C3 C4 120.8(5) . . ?
C2 C3 H1 119.6 . . ?
C4 C3 H1 119.6 . . ?
C7 C6 C5 123.0(5) . . ?
C7 C6 C12 118.1(5) . . ?
C5 C6 C12 118.9(5) . . ?
C14 C13 N1 119.3(5) . . ?
C18 C13 N1 119.4(6) . . ?
C18 C13 C14 121.3(6) . . ?
C15 C14 H5 120.7 . . ?
C13 C14 C15 118.6(6) . . ?
C13 C14 H5 120.7 . . ?
C15 C16 H7 119.7 . . ?
C15 C16 C17 120.5(6) . . ?
C17 C16 H7 119.7 . . ?
C13 C18 H9 120.2 . . ?
C13 C18 C17 119.5(6) . . ?
C17 C18 H9 120.2 . . ?
C16 C17 C18 119.7(6) . . ?
C16 C17 H8 120.2 . . ?
C18 C17 H8 120.2 . . ?

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
O1 C1 C2 C12 -178.6(6) . . . . ?
O1 C1 C2 C3 2.6(10) . . . . ?
N1 C1 C2 C12 -0.3(9) . . . . ?
N1 C1 C2 C3 -179.2(6) . . . . ?
N1 C13 C14 C15 -177.7(6) . . . . ?
N1 C13 C18 C17 179.0(6) . . . . ?
C10 C12 C6 C7 -1.8(10) . . . . ?
C10 C12 C6 C5 179.7(6) . . . . ?
C7 C8 C9 C10 0.1(11) . . . . ?
C7 C5 C4 C3 178.8(6) 3_666 . . . ?
C7 C5 C6 C7 2.9(11) 3_666 . . . ?
C7 C5 C6 C12 -178.8(6) 3_666 . . . ?
C1 N1 C11 O2 -175.2(6) . . . . ?
C1 N1 C11 C10 3.0(9) . . . . ?
C1 N1 C13 C14 58.0(9) . . . . ?
C1 N1 C13 C18 -121.1(7) . . . . ?
C1 C2 C12 C10 -0.1(9) . . . . ?
C1 C2 C12 C6 179.0(6) . . . . ?
C1 C2 C3 C4 -178.9(6) . . . . ?
C8 C7 C6 C5 179.0(6) . . . . ?
C8 C7 C6 C12 0.6(9) . . . . ?
C2 C12 C6 C7 179.0(6) . . . . ?
C2 C12 C6 C5 0.5(9) . . . . ?
C9 C10 C11 O2 -4.5(10) . . . . ?
C9 C10 C11 N1 177.3(6) . . . . ?
C9 C10 C12 C2 -178.7(6) . . . . ?
C9 C10 C12 C6 2.2(10) . . . . ?
C5 C7 C8 C9 -177.8(6) 3_666 . . . ?
C5 C7 C6 C5 -2.8(10) 3_666 . . . ?
C5 C7 C6 C12 178.8(6) 3_666 . . . ?
C5 C4 C3 C2 -0.7(10) . . . . ?
C11 N1 C1 O1 177.0(6) . . . . ?
C11 N1 C1 C2 -1.2(9) . . . . ?
C11 N1 C13 C14 -124.8(7) . . . . ?
C11 N1 C13 C18 56.1(9) . . . . ?
C11 C10 C9 C8 178.0(6) . . . . ?
C11 C10 C12 C2 2.0(10) . . . . ?
C11 C10 C12 C6 -177.1(6) . . . . ?
C15 C16 C17 C18 1.2(11) . . . . ?
C4 C5 C6 C7 -177.5(6) . . . . ?
C4 C5 C6 C12 0.9(9) . . . . ?
C12 C10 C9 C8 -1.3(10) . . . . ?
C12 C10 C11 O2 174.8(7) . . . . ?
C12 C10 C11 N1 -3.4(9) . . . . ?
C12 C2 C3 C4 2.2(10) . . . . ?
C3 C2 C12 C10 178.7(6) . . . . ?
C3 C2 C12 C6 -2.1(9) . . . . ?
C6 C7 C8 C9 0.2(10) . . . . ?
C6 C5 C4 C3 -0.9(10) . . . . ?
C13 N1 C1 O1 -6.1(10) . . . . ?
C13 N1 C1 C2 175.7(6) . . . . ?
C13 N1 C11 O2 7.9(10) . . . . ?
C13 N1 C11 C10 -174.0(6) . . . . ?
C13 C18 C17 C16 -1.3(11) . . . . ?
C14 C15 C16 C17 0.2(11) . . . . ?
C14 C13 C18 C17 -0.1(11) . . . . ?
C16 C15 C14 C13 -1.5(11) . . . . ?
C18 C13 C14 C15 1.4(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_PTCDI_Ph_170K
_database_code_depnum_ccdc_archive 'CCDC 2253195'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PTCDI_Ph_170K       
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      55.00 Degree
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_RINTA01_PTCDI_Ph_170K       
;
PROBLEM: The value of Rint is greater than 0.18
            Rint given   0.192
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_PLAT020_PTCDI_Ph_170K       
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.192 Report
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_PLAT026_PTCDI_Ph_170K       
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        31% Check 
RESPONSE: This low value comes from the overall poor diffraction quality of the 
crystal.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-03-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.755(2)
_cell_length_b                   3.9289(7)
_cell_length_c                   18.307(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.707(13)
_cell_angle_gamma                90
_cell_volume                     1191.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    388
_cell_measurement_temperature    169.8(4)
_cell_measurement_theta_max      66.7530
_cell_measurement_theta_min      2.6480
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -3 -1 0.0543
0 0 12 0.0089
0 0 -12 0.0287
11 0 -1 0.0708
-1 2 -2 0.0708
-11 0 1 0.0208

_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1922
_diffrn_reflns_av_unetI/netI     0.2283
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4514
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        55.000
_diffrn_reflns_theta_max         73.901
_diffrn_reflns_theta_min         2.668
_diffrn_ambient_temperature      170.15
_diffrn_detector_area_resol_mean 10.5384
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
 Data were collected at temperature of 170 K
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                718
_reflns_number_total             2323
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2255
_refine_ls_R_factor_gt           0.0856
_refine_ls_restrained_S_all      0.918
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.2366
_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:
 C3(H1), C9(H4), C8(H3), C4(H2), C14(H5), C15(H6), C16(H7), C17(H8), C18(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.6855(2) 0.6085(12) 0.8116(2) 0.0394(12) Uani 1 1 d . . . . .
O2 O 0.8306(3) 0.0535(14) 0.6564(2) 0.0471(14) Uani 1 1 d . . . . .
N1 N 0.7615(3) 0.3459(15) 0.7354(3) 0.0363(14) Uani 1 1 d . . . . .
C1 C 0.6924(3) 0.5027(17) 0.7500(3) 0.0329(16) Uani 1 1 d . . . . .
C2 C 0.6243(3) 0.5452(17) 0.6880(3) 0.0295(15) Uani 1 1 d . . . . .
C3 C 0.5555(3) 0.7055(18) 0.6996(3) 0.0332(16) Uani 1 1 d . . . . .
H1 H 0.551712 0.791900 0.747420 0.040 Uiso 1 1 calc R U . . .
C9 C 0.7117(4) 0.1494(18) 0.5342(3) 0.0373(17) Uani 1 1 d . . . . .
H4 H 0.760259 0.041788 0.525807 0.045 Uiso 1 1 calc R U . . .
C5 C 0.4936(4) 0.6256(16) 0.5730(3) 0.0284(14) Uani 1 1 d . . . . .
C6 C 0.5659(3) 0.4629(17) 0.5586(3) 0.0311(15) Uani 1 1 d . . . . .
C7 C 0.5751(3) 0.3368(16) 0.4871(3) 0.0268(14) Uani 1 1 d . . . . .
C8 C 0.6469(3) 0.1956(17) 0.4765(3) 0.0353(16) Uani 1 1 d . . . . .
H3 H 0.653480 0.125491 0.428096 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4901(3) 0.7469(17) 0.6433(3) 0.0333(16) Uani 1 1 d . . . . .
H2 H 0.442788 0.859467 0.653411 0.040 Uiso 1 1 calc R U . . .
C10 C 0.7022(3) 0.2663(17) 0.6036(3) 0.0310(16) Uani 1 1 d . . . . .
C11 C 0.7708(4) 0.2122(18) 0.6652(3) 0.0348(16) Uani 1 1 d . . . . .
C12 C 0.6323(3) 0.4200(18) 0.6168(3) 0.0316(16) Uani 1 1 d . . . . .
C13 C 0.8308(3) 0.3248(18) 0.7940(3) 0.0349(16) Uani 1 1 d . . . . .
C14 C 0.8218(4) 0.1716(19) 0.8600(3) 0.0441(19) Uani 1 1 d . . . . .
H5 H 0.771304 0.077183 0.866952 0.053 Uiso 1 1 calc R U . . .
C15 C 0.8877(4) 0.157(2) 0.9162(4) 0.051(2) Uani 1 1 d . . . . .
H6 H 0.882829 0.051526 0.962004 0.061 Uiso 1 1 calc R U . . .
C16 C 0.9600(4) 0.297(2) 0.9046(4) 0.051(2) Uani 1 1 d . . . . .
H7 H 1.004610 0.289949 0.943363 0.061 Uiso 1 1 calc R U . . .
C17 C 0.9699(4) 0.447(2) 0.8389(4) 0.050(2) Uani 1 1 d . . . . .
H8 H 1.020758 0.536876 0.831774 0.060 Uiso 1 1 calc R U . . .
C18 C 0.9031(4) 0.4655(18) 0.7824(3) 0.0396(17) Uani 1 1 d . . . . .
H9 H 0.907807 0.573658 0.736858 0.048 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
O1 C1 1.224(7) . ?
O2 C11 1.210(7) . ?
N1 C1 1.373(7) . ?
N1 C11 1.419(7) . ?
N1 C13 1.460(7) . ?
C1 C2 1.491(8) . ?
C2 C3 1.359(8) . ?
C2 C12 1.420(8) . ?
C3 H1 0.9500 . ?
C3 C4 1.394(7) . ?
C9 H4 0.9500 . ?
C9 C8 1.407(8) . ?
C9 C10 1.383(8) . ?
C5 C6 1.429(8) . ?
C5 C7 1.475(8) 3_666 ?
C5 C4 1.382(8) . ?
C6 C7 1.430(7) . ?
C6 C12 1.428(8) . ?
C7 C8 1.366(8) . ?
C8 H3 0.9500 . ?
C4 H2 0.9500 . ?
C10 C11 1.499(8) . ?
C10 C12 1.371(8) . ?
C13 C14 1.378(8) . ?
C13 C18 1.376(8) . ?
C14 H5 0.9500 . ?
C14 C15 1.392(8) . ?
C15 H6 0.9500 . ?
C15 C16 1.377(10) . ?
C16 H7 0.9500 . ?
C16 C17 1.370(10) . ?
C17 H8 0.9500 . ?
C17 C18 1.406(8) . ?
C18 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 123.7(5) . . ?
C1 N1 C13 118.9(5) . . ?
C11 N1 C13 117.4(5) . . ?
O1 C1 N1 122.1(5) . . ?
O1 C1 C2 119.7(6) . . ?
N1 C1 C2 118.2(5) . . ?
C3 C2 C1 120.2(5) . . ?
C3 C2 C12 120.3(5) . . ?
C12 C2 C1 119.5(5) . . ?
C2 C3 H1 119.0 . . ?
C2 C3 C4 122.0(6) . . ?
C4 C3 H1 119.0 . . ?
C8 C9 H4 121.2 . . ?
C10 C9 H4 121.2 . . ?
C10 C9 C8 117.7(6) . . ?
C6 C5 C7 119.6(5) . 3_666 ?
C4 C5 C6 118.9(5) . . ?
C4 C5 C7 121.5(5) . 3_666 ?
C5 C6 C7 122.4(5) . . ?
C12 C6 C5 120.1(6) . . ?
C12 C6 C7 117.5(5) . . ?
C6 C7 C5 118.0(5) . 3_666 ?
C8 C7 C5 122.7(5) . 3_666 ?
C8 C7 C6 119.3(5) . . ?
C9 C8 H3 118.6 . . ?
C7 C8 C9 122.8(6) . . ?
C7 C8 H3 118.6 . . ?
C3 C4 H2 119.7 . . ?
C5 C4 C3 120.6(6) . . ?
C5 C4 H2 119.7 . . ?
C9 C10 C11 117.5(5) . . ?
C12 C10 C9 121.9(5) . . ?
C12 C10 C11 120.6(5) . . ?
O2 C11 N1 121.2(5) . . ?
O2 C11 C10 121.9(6) . . ?
N1 C11 C10 116.8(5) . . ?
C2 C12 C6 118.2(5) . . ?
C10 C12 C2 121.0(5) . . ?
C10 C12 C6 120.7(6) . . ?
C14 C13 N1 119.2(6) . . ?
C18 C13 N1 119.0(6) . . ?
C18 C13 C14 121.8(6) . . ?
C13 C14 H5 120.5 . . ?
C13 C14 C15 119.1(7) . . ?
C15 C14 H5 120.5 . . ?
C14 C15 H6 120.4 . . ?
C16 C15 C14 119.2(7) . . ?
C16 C15 H6 120.4 . . ?
C15 C16 H7 118.9 . . ?
C17 C16 C15 122.2(7) . . ?
C17 C16 H7 118.9 . . ?
C16 C17 H8 120.7 . . ?
C16 C17 C18 118.7(7) . . ?
C18 C17 H8 120.7 . . ?
C13 C18 C17 119.1(6) . . ?
C13 C18 H9 120.4 . . ?
C17 C18 H9 120.4 . . ?

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
O1 C1 C2 C3 1.1(10) . . . . ?
O1 C1 C2 C12 -179.5(6) . . . . ?
N1 C1 C2 C3 -178.6(6) . . . . ?
N1 C1 C2 C12 0.8(9) . . . . ?
N1 C13 C14 C15 -178.9(7) . . . . ?
N1 C13 C18 C17 179.7(6) . . . . ?
C1 N1 C11 O2 -174.3(7) . . . . ?
C1 N1 C11 C10 3.5(10) . . . . ?
C1 N1 C13 C14 56.8(9) . . . . ?
C1 N1 C13 C18 -121.8(7) . . . . ?
C1 C2 C3 C4 -179.3(6) . . . . ?
C1 C2 C12 C6 179.7(6) . . . . ?
C1 C2 C12 C10 -1.2(10) . . . . ?
C2 C3 C4 C5 -0.3(10) . . . . ?
C3 C2 C12 C6 -1.0(10) . . . . ?
C3 C2 C12 C10 178.2(7) . . . . ?
C9 C10 C11 O2 -4.7(10) . . . . ?
C9 C10 C11 N1 177.5(6) . . . . ?
C9 C10 C12 C2 -178.6(6) . . . . ?
C9 C10 C12 C6 0.5(10) . . . . ?
C5 C6 C7 C5 -0.8(10) . . . 3_666 ?
C5 C6 C7 C8 177.5(6) . . . . ?
C5 C6 C12 C2 -0.5(9) . . . . ?
C5 C6 C12 C10 -179.6(6) . . . . ?
C5 C7 C8 C9 -177.9(6) 3_666 . . . ?
C6 C5 C4 C3 -1.2(9) . . . . ?
C6 C7 C8 C9 3.8(10) . . . . ?
C7 C5 C6 C7 0.8(10) 3_666 . . . ?
C7 C5 C6 C12 -179.0(6) 3_666 . . . ?
C7 C5 C4 C3 179.3(6) 3_666 . . . ?
C7 C6 C12 C2 179.7(6) . . . . ?
C7 C6 C12 C10 0.6(9) . . . . ?
C8 C9 C10 C11 179.1(6) . . . . ?
C8 C9 C10 C12 0.4(11) . . . . ?
C4 C5 C6 C7 -178.7(6) . . . . ?
C4 C5 C6 C12 1.6(9) . . . . ?
C10 C9 C8 C7 -2.7(11) . . . . ?
C11 N1 C1 O1 178.3(6) . . . . ?
C11 N1 C1 C2 -2.1(10) . . . . ?
C11 N1 C13 C14 -125.4(7) . . . . ?
C11 N1 C13 C18 56.0(9) . . . . ?
C11 C10 C12 C2 2.8(10) . . . . ?
C11 C10 C12 C6 -178.2(6) . . . . ?
C12 C2 C3 C4 1.4(10) . . . . ?
C12 C6 C7 C5 179.0(6) . . . 3_666 ?
C12 C6 C7 C8 -2.7(9) . . . . ?
C12 C10 C11 O2 174.0(7) . . . . ?
C12 C10 C11 N1 -3.8(10) . . . . ?
C13 N1 C1 O1 -4.1(10) . . . . ?
C13 N1 C1 C2 175.5(6) . . . . ?
C13 N1 C11 O2 8.0(10) . . . . ?
C13 N1 C11 C10 -174.1(6) . . . . ?
C13 C14 C15 C16 0.3(12) . . . . ?
C14 C13 C18 C17 1.1(11) . . . . ?
C14 C15 C16 C17 -1.0(12) . . . . ?
C15 C16 C17 C18 1.7(12) . . . . ?
C16 C17 C18 C13 -1.7(11) . . . . ?
C18 C13 C14 C15 -0.4(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_PTCDI_Ph_200K
_database_code_depnum_ccdc_archive 'CCDC 2253196'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PTCDI_Ph_200K       
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      60.00 Degree
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_RINTA01_PTCDI_Ph_200K       
;
PROBLEM: The value of Rint is greater than 0.18
            Rint given   0.205
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_PLAT020_PTCDI_Ph_200K       
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.205 Report
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_PLAT026_PTCDI_Ph_200K       
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        31% Check 
RESPONSE: This low value comes from the overall poor diffraction quality of the 
crystal.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-03-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.7559(14)
_cell_length_b                   3.9338(3)
_cell_length_c                   18.3169(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.673(7)
_cell_angle_gamma                90
_cell_volume                     1193.53(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    429
_cell_measurement_temperature    200.1(3)
_cell_measurement_theta_max      66.1610
_cell_measurement_theta_min      4.8640
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.806
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -3 -1 0.0543
0 0 12 0.0089
1 0 -12 0.0287
11 0 -1 0.0708
0 3 -2 0.0708
-11 0 1 0.0138

_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2048
_diffrn_reflns_av_unetI/netI     0.2320
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4589
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        60.000
_diffrn_reflns_theta_max         73.660
_diffrn_reflns_theta_min         2.668
_diffrn_ambient_temperature      200.15
_diffrn_detector_area_resol_mean 10.5384
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
 Data were collected at temperature of 200 K
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                731
_reflns_number_total             2331
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2232
_refine_ls_R_factor_gt           0.0878
_refine_ls_restrained_S_all      0.904
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.2205
_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:
 C8(H8), C9(H9), C15(H15), C4(H4), C3(H3), C14(H14), C16(H16), C18(H18),
 C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8303(2) 0.0536(13) 0.6566(2) 0.0486(13) Uani 1 1 d . . . . .
O1 O 0.6848(2) 0.6080(12) 0.8118(2) 0.0429(12) Uani 1 1 d . . . . .
N1 N 0.7611(3) 0.3470(14) 0.7352(2) 0.0317(13) Uani 1 1 d . . . . .
C10 C 0.7027(3) 0.2662(17) 0.6034(3) 0.0319(15) Uani 1 1 d . . . . .
C7 C 0.5750(3) 0.3423(16) 0.4865(3) 0.0293(14) Uani 1 1 d . . . . .
C1 C 0.6924(3) 0.5050(17) 0.7500(3) 0.0345(16) Uani 1 1 d . . . . .
C8 C 0.6457(3) 0.1925(17) 0.4769(3) 0.0375(16) Uani 1 1 d . . . . .
H8 H 0.651364 0.112238 0.429019 0.045 Uiso 1 1 calc R U . . .
C2 C 0.6246(3) 0.5500(17) 0.6876(3) 0.0323(15) Uani 1 1 d . . . . .
C9 C 0.7110(3) 0.1500(18) 0.5343(3) 0.0418(18) Uani 1 1 d . . . . .
H9 H 0.759553 0.043785 0.525383 0.050 Uiso 1 1 calc R U . . .
C5 C 0.4943(3) 0.6249(16) 0.5724(3) 0.0280(14) Uani 1 1 d . . . . .
C11 C 0.7711(3) 0.2134(18) 0.6655(3) 0.0348(16) Uani 1 1 d . . . . .
C15 C 0.8880(4) 0.161(2) 0.9158(3) 0.050(2) Uani 1 1 d . . . . .
H15 H 0.882803 0.060552 0.962020 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4901(3) 0.7502(17) 0.6432(3) 0.0340(15) Uani 1 1 d . . . . .
H4 H 0.442901 0.864541 0.652846 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6325(3) 0.4238(16) 0.6163(3) 0.0302(14) Uani 1 1 d . . . . .
C3 C 0.5556(3) 0.7073(18) 0.7000(3) 0.0363(16) Uani 1 1 d . . . . .
H3 H 0.551624 0.789725 0.748051 0.044 Uiso 1 1 calc R U . . .
C6 C 0.5656(3) 0.4622(16) 0.5585(3) 0.0281(14) Uani 1 1 d . . . . .
C13 C 0.8309(3) 0.3264(17) 0.7936(3) 0.0353(16) Uani 1 1 d . . . . .
C14 C 0.8218(4) 0.1671(18) 0.8597(3) 0.0431(17) Uani 1 1 d . . . . .
H14 H 0.771991 0.065392 0.866353 0.052 Uiso 1 1 calc R U . . .
C16 C 0.9592(4) 0.297(2) 0.9052(4) 0.054(2) Uani 1 1 d . . . . .
H16 H 1.003376 0.289614 0.944308 0.065 Uiso 1 1 calc R U . . .
C18 C 0.9029(3) 0.4689(18) 0.7824(3) 0.0406(17) Uani 1 1 d . . . . .
H18 H 0.907631 0.581589 0.737429 0.049 Uiso 1 1 calc R U . . .
C17 C 0.9697(4) 0.4444(19) 0.8394(4) 0.0495(19) Uani 1 1 d . . . . .
H17 H 1.021112 0.528769 0.832255 0.059 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
O2 C11 1.206(7) . ?
O1 C1 1.227(6) . ?
N1 C1 1.371(7) . ?
N1 C11 1.413(7) . ?
N1 C13 1.464(7) . ?
C10 C9 1.373(8) . ?
C10 C11 1.504(7) . ?
C10 C12 1.380(8) . ?
C7 C8 1.358(8) . ?
C7 C5 1.466(7) 3_666 ?
C7 C6 1.432(7) . ?
C1 C2 1.495(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.409(8) . ?
C2 C12 1.421(8) . ?
C2 C3 1.361(8) . ?
C9 H9 0.9500 . ?
C5 C4 1.399(7) . ?
C5 C6 1.412(7) . ?
C15 H15 0.9500 . ?
C15 C14 1.394(8) . ?
C15 C16 1.348(9) . ?
C4 H4 0.9500 . ?
C4 C3 1.403(7) . ?
C12 C6 1.429(7) . ?
C3 H3 0.9500 . ?
C13 C14 1.391(8) . ?
C13 C18 1.373(8) . ?
C14 H14 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.373(9) . ?
C18 H18 0.9500 . ?
C18 C17 1.415(8) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 124.4(5) . . ?
C1 N1 C13 118.9(5) . . ?
C11 N1 C13 116.7(5) . . ?
C9 C10 C11 118.7(5) . . ?
C9 C10 C12 121.0(5) . . ?
C12 C10 C11 120.3(5) . . ?
C8 C7 C5 123.6(6) . 3_666 ?
C8 C7 C6 118.7(5) . . ?
C6 C7 C5 117.7(5) . 3_666 ?
O1 C1 N1 122.6(5) . . ?
O1 C1 C2 119.6(6) . . ?
N1 C1 C2 117.8(5) . . ?
C7 C8 H8 118.3 . . ?
C7 C8 C9 123.4(6) . . ?
C9 C8 H8 118.3 . . ?
C12 C2 C1 119.7(5) . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 C12 120.7(5) . . ?
C10 C9 C8 118.2(6) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C4 C5 C7 120.4(5) . 3_666 ?
C4 C5 C6 119.3(5) . . ?
C6 C5 C7 120.3(5) . 3_666 ?
O2 C11 N1 121.8(5) . . ?
O2 C11 C10 121.3(6) . . ?
N1 C11 C10 116.8(5) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C16 C15 C14 120.7(7) . . ?
C5 C4 H4 119.9 . . ?
C5 C4 C3 120.1(6) . . ?
C3 C4 H4 119.9 . . ?
C10 C12 C2 120.9(5) . . ?
C10 C12 C6 120.9(5) . . ?
C2 C12 C6 118.2(5) . . ?
C2 C3 C4 121.3(6) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C6 C7 121.9(5) . . ?
C5 C6 C12 120.3(5) . . ?
C12 C6 C7 117.7(5) . . ?
C14 C13 N1 118.7(5) . . ?
C18 C13 N1 119.4(6) . . ?
C18 C13 C14 121.8(5) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 C15 118.0(6) . . ?
C13 C14 H14 121.0 . . ?
C15 C16 H16 119.1 . . ?
C15 C16 C17 121.9(6) . . ?
C17 C16 H16 119.1 . . ?
C13 C18 H18 120.7 . . ?
C13 C18 C17 118.5(6) . . ?
C17 C18 H18 120.7 . . ?
C16 C17 C18 118.9(6) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 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
O1 C1 C2 C12 -178.5(6) . . . . ?
O1 C1 C2 C3 0.5(10) . . . . ?
N1 C1 C2 C12 1.3(9) . . . . ?
N1 C1 C2 C3 -179.6(6) . . . . ?
N1 C13 C14 C15 -177.6(6) . . . . ?
N1 C13 C18 C17 -179.6(6) . . . . ?
C10 C12 C6 C7 -2.0(9) . . . . ?
C10 C12 C6 C5 -179.8(6) . . . . ?
C7 C8 C9 C10 0.0(11) . . . . ?
C7 C5 C4 C3 177.7(6) 3_666 . . . ?
C7 C5 C6 C7 3.7(10) 3_666 . . . ?
C7 C5 C6 C12 -178.7(6) 3_666 . . . ?
C1 N1 C11 O2 -174.2(6) . . . . ?
C1 N1 C11 C10 3.2(9) . . . . ?
C1 N1 C13 C14 58.2(9) . . . . ?
C1 N1 C13 C18 -120.8(7) . . . . ?
C1 C2 C12 C10 -1.4(10) . . . . ?
C1 C2 C12 C6 178.1(6) . . . . ?
C1 C2 C3 C4 -179.1(6) . . . . ?
C8 C7 C6 C5 179.1(6) . . . . ?
C8 C7 C6 C12 1.4(9) . . . . ?
C2 C12 C6 C7 178.4(6) . . . . ?
C2 C12 C6 C5 0.7(9) . . . . ?
C9 C10 C11 O2 -4.7(10) . . . . ?
C9 C10 C11 N1 177.9(6) . . . . ?
C9 C10 C12 C2 -178.7(6) . . . . ?
C9 C10 C12 C6 1.7(10) . . . . ?
C5 C7 C8 C9 -177.5(6) 3_666 . . . ?
C5 C7 C6 C5 -3.6(10) 3_666 . . . ?
C5 C7 C6 C12 178.7(6) 3_666 . . . ?
C5 C4 C3 C2 1.2(10) . . . . ?
C11 N1 C1 O1 177.5(6) . . . . ?
C11 N1 C1 C2 -2.3(9) . . . . ?
C11 N1 C13 C14 -124.6(6) . . . . ?
C11 N1 C13 C18 56.5(9) . . . . ?
C11 C10 C9 C8 178.3(6) . . . . ?
C11 C10 C12 C2 2.3(10) . . . . ?
C11 C10 C12 C6 -177.2(6) . . . . ?
C15 C16 C17 C18 3.0(12) . . . . ?
C4 C5 C6 C7 -177.2(6) . . . . ?
C4 C5 C6 C12 0.5(9) . . . . ?
C12 C10 C9 C8 -0.7(10) . . . . ?
C12 C10 C11 O2 174.3(7) . . . . ?
C12 C10 C11 N1 -3.1(9) . . . . ?
C12 C2 C3 C4 0.0(10) . . . . ?
C3 C2 C12 C10 179.5(6) . . . . ?
C3 C2 C12 C6 -0.9(9) . . . . ?
C6 C7 C8 C9 -0.4(10) . . . . ?
C6 C5 C4 C3 -1.4(9) . . . . ?
C13 N1 C1 O1 -5.5(10) . . . . ?
C13 N1 C1 C2 174.7(6) . . . . ?
C13 N1 C11 O2 8.8(10) . . . . ?
C13 N1 C11 C10 -173.9(6) . . . . ?
C13 C18 C17 C16 -3.7(11) . . . . ?
C14 C15 C16 C17 -0.1(12) . . . . ?
C14 C13 C18 C17 1.5(11) . . . . ?
C16 C15 C14 C13 -2.1(11) . . . . ?
C18 C13 C14 C15 1.3(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_PTCDI_Ph_250K
_database_code_depnum_ccdc_archive 'CCDC 2253198'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_PTCDI_Ph_250K       
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        28% Check 
RESPONSE: This low value comes from the overall poor diffraction quality of 
the crystal.
;
_vrf_PLAT027_PTCDI_Ph_250K       
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      60.00 Degree
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_RINTA01_PTCDI_Ph_250K       
;
PROBLEM: The value of Rint is greater than 0.18
            Rint given   0.198
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_PLAT020_PTCDI_Ph_250K       
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.198 Report
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-02-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.7456(12)
_cell_length_b                   3.9671(3)
_cell_length_c                   18.3012(12)
_cell_angle_alpha                90
_cell_angle_beta                 98.605(6)
_cell_angle_gamma                90
_cell_volume                     1202.09(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    390
_cell_measurement_temperature    250.2(3)
_cell_measurement_theta_max      65.3120
_cell_measurement_theta_min      2.6500
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -3 -1 0.0543
0 0 12 0.0089
1 0 -12 0.0287
11 0 -1 0.0708
0 3 -2 0.0708
-11 0 1 0.0658

_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1982
_diffrn_reflns_av_unetI/netI     0.2353
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4607
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        60.000
_diffrn_reflns_theta_max         73.660
_diffrn_reflns_theta_min         2.669
_diffrn_ambient_temperature      250.15
_diffrn_detector_area_resol_mean 10.5384
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
 Data were collected at temperature of 250 K
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                660
_reflns_number_total             2339
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0007(2)
_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   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2493
_refine_ls_R_factor_gt           0.0943
_refine_ls_restrained_S_all      0.959
_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)+(0.0251P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1848
_refine_ls_wR_factor_ref         0.2849
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C8(H3), C9(H4), C15(H6), C4(H2), C3(H1), C14(H5), C16(H7), C18(H9), C17(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8305(3) 0.0554(16) 0.6567(3) 0.0614(18) Uani 1 1 d . . . . .
O1 O 0.6851(3) 0.6084(15) 0.8114(3) 0.0532(16) Uani 1 1 d . . . . .
N1 N 0.7620(3) 0.3465(16) 0.7351(3) 0.0405(16) Uani 1 1 d . . . . .
C10 C 0.7029(4) 0.2673(19) 0.6039(4) 0.0418(18) Uani 1 1 d . . . . .
C7 C 0.5747(4) 0.3441(17) 0.4875(4) 0.0343(16) Uani 1 1 d . . . . .
C1 C 0.6917(4) 0.5010(19) 0.7494(3) 0.0376(17) Uani 1 1 d . . . . .
C8 C 0.6454(4) 0.1898(18) 0.4772(4) 0.0405(18) Uani 1 1 d . . . . .
H3 H 0.650485 0.106861 0.430030 0.049 Uiso 1 1 calc R U . . .
C2 C 0.6240(4) 0.5506(19) 0.6876(3) 0.0364(17) Uani 1 1 d . . . . .
C9 C 0.7105(4) 0.151(2) 0.5345(4) 0.045(2) Uani 1 1 d . . . . .
H4 H 0.758588 0.046873 0.525600 0.054 Uiso 1 1 calc R U . . .
C5 C 0.4950(4) 0.623(2) 0.5721(3) 0.0400(18) Uani 1 1 d . . . . .
C11 C 0.7717(4) 0.213(2) 0.6648(3) 0.042(2) Uani 1 1 d . . . . .
C15 C 0.8874(5) 0.159(2) 0.9150(4) 0.063(3) Uani 1 1 d . . . . .
H6 H 0.882589 0.054235 0.960269 0.075 Uiso 1 1 calc R U . . .
C4 C 0.4907(4) 0.749(2) 0.6431(4) 0.045(2) Uani 1 1 d . . . . .
H2 H 0.443757 0.860386 0.652620 0.054 Uiso 1 1 calc R U . . .
C12 C 0.6317(4) 0.4224(18) 0.6165(3) 0.0352(16) Uani 1 1 d . . . . .
C3 C 0.5563(4) 0.709(2) 0.7000(4) 0.0416(19) Uani 1 1 d . . . . .
H1 H 0.552794 0.793393 0.747427 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5648(4) 0.4626(18) 0.5592(4) 0.0342(16) Uani 1 1 d . . . . .
C13 C 0.8311(4) 0.326(2) 0.7944(4) 0.0430(18) Uani 1 1 d . . . . .
C14 C 0.8210(4) 0.170(2) 0.8607(4) 0.057(2) Uani 1 1 d . . . . .
H5 H 0.771188 0.076987 0.867905 0.069 Uiso 1 1 calc R U . . .
C16 C 0.9591(5) 0.293(2) 0.9054(5) 0.063(3) Uani 1 1 d . . . . .
H7 H 1.002973 0.280376 0.943880 0.075 Uiso 1 1 calc R U . . .
C18 C 0.9017(4) 0.462(2) 0.7828(4) 0.052(2) Uani 1 1 d . . . . .
H9 H 0.906103 0.565544 0.737314 0.062 Uiso 1 1 calc R U . . .
C17 C 0.9691(4) 0.450(2) 0.8392(5) 0.060(2) Uani 1 1 d . . . . .
H8 H 1.018996 0.544158 0.832414 0.072 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
O2 C11 1.196(8) . ?
O1 C1 1.232(7) . ?
N1 C1 1.387(8) . ?
N1 C11 1.422(8) . ?
N1 C13 1.467(7) . ?
C10 C9 1.375(9) . ?
C10 C11 1.494(9) . ?
C10 C12 1.390(9) . ?
C7 C8 1.370(9) . ?
C7 C5 1.480(8) 3_666 ?
C7 C6 1.427(9) . ?
C1 C2 1.490(8) . ?
C8 H3 0.9400 . ?
C8 C9 1.404(8) . ?
C2 C12 1.421(8) . ?
C2 C3 1.345(9) . ?
C9 H4 0.9400 . ?
C5 C4 1.403(9) . ?
C5 C6 1.383(9) . ?
C15 H6 0.9400 . ?
C15 C14 1.377(9) . ?
C15 C16 1.349(11) . ?
C4 H2 0.9400 . ?
C4 C3 1.406(8) . ?
C12 C6 1.424(8) . ?
C3 H1 0.9400 . ?
C13 C14 1.393(10) . ?
C13 C18 1.346(9) . ?
C14 H5 0.9400 . ?
C16 H7 0.9400 . ?
C16 C17 1.394(11) . ?
C18 H9 0.9400 . ?
C18 C17 1.413(9) . ?
C17 H8 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 123.4(5) . . ?
C1 N1 C13 118.8(5) . . ?
C11 N1 C13 117.7(5) . . ?
C9 C10 C11 118.2(6) . . ?
C12 C10 C9 120.2(6) . . ?
C12 C10 C11 121.6(7) . . ?
C8 C7 C5 122.7(6) . 3_666 ?
C8 C7 C6 119.7(6) . . ?
C6 C7 C5 117.5(6) . 3_666 ?
O1 C1 N1 121.5(6) . . ?
O1 C1 C2 119.4(6) . . ?
N1 C1 C2 119.0(6) . . ?
C7 C8 H3 118.7 . . ?
C7 C8 C9 122.5(7) . . ?
C9 C8 H3 118.7 . . ?
C12 C2 C1 119.0(6) . . ?
C3 C2 C1 119.8(6) . . ?
C3 C2 C12 121.1(6) . . ?
C10 C9 C8 118.9(6) . . ?
C10 C9 H4 120.5 . . ?
C8 C9 H4 120.5 . . ?
C4 C5 C7 120.5(6) . 3_666 ?
C4 C5 C6 119.0(6) . . ?
C6 C5 C7 120.6(6) . 3_666 ?
O2 C11 N1 121.0(6) . . ?
O2 C11 C10 122.7(7) . . ?
N1 C11 C10 116.2(6) . . ?
C14 C15 H6 119.0 . . ?
C16 C15 H6 119.0 . . ?
C16 C15 C14 122.0(8) . . ?
C5 C4 H2 119.9 . . ?
C5 C4 C3 120.2(7) . . ?
C3 C4 H2 119.9 . . ?
C10 C12 C2 120.5(6) . . ?
C10 C12 C6 121.8(6) . . ?
C6 C12 C2 117.7(6) . . ?
C2 C3 C4 120.9(7) . . ?
C2 C3 H1 119.6 . . ?
C4 C3 H1 119.6 . . ?
C5 C6 C7 121.8(6) . . ?
C12 C6 C7 117.0(6) . . ?
C12 C6 C5 121.2(6) . . ?
C14 C13 N1 119.0(6) . . ?
C18 C13 N1 118.4(7) . . ?
C18 C13 C14 122.7(6) . . ?
C15 C14 H5 121.5 . . ?
C13 C14 C15 117.0(8) . . ?
C13 C14 H5 121.5 . . ?
C15 C16 H7 119.5 . . ?
C15 C16 C17 121.0(8) . . ?
C17 C16 H7 119.5 . . ?
C13 C18 H9 120.2 . . ?
C17 C18 C13 119.7(7) . . ?
C17 C18 H9 120.2 . . ?
C16 C17 H8 121.2 . . ?
C18 C17 C16 117.6(7) . . ?
C18 C17 H8 121.2 . . ?

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
O1 C1 C2 C12 -179.3(7) . . . . ?
O1 C1 C2 C3 -0.6(11) . . . . ?
N1 C1 C2 C12 3.3(10) . . . . ?
N1 C1 C2 C3 -178.0(7) . . . . ?
N1 C13 C14 C15 -179.6(7) . . . . ?
N1 C13 C18 C17 179.3(7) . . . . ?
C10 C12 C6 C7 -1.6(10) . . . . ?
C10 C12 C6 C5 -178.7(7) . . . . ?
C7 C8 C9 C10 1.0(12) . . . . ?
C7 C5 C4 C3 178.1(7) 3_666 . . . ?
C7 C5 C6 C7 4.6(12) 3_666 . . . ?
C7 C5 C6 C12 -178.5(6) 3_666 . . . ?
C1 N1 C11 O2 -173.1(7) . . . . ?
C1 N1 C11 C10 3.8(11) . . . . ?
C1 N1 C13 C14 56.8(10) . . . . ?
C1 N1 C13 C18 -122.5(8) . . . . ?
C1 C2 C12 C10 -3.0(11) . . . . ?
C1 C2 C12 C6 177.7(6) . . . . ?
C1 C2 C3 C4 -178.0(7) . . . . ?
C8 C7 C6 C5 179.2(7) . . . . ?
C8 C7 C6 C12 2.2(10) . . . . ?
C2 C12 C6 C7 177.7(6) . . . . ?
C2 C12 C6 C5 0.6(10) . . . . ?
C9 C10 C11 O2 -4.9(12) . . . . ?
C9 C10 C11 N1 178.2(7) . . . . ?
C9 C10 C12 C2 -178.5(7) . . . . ?
C9 C10 C12 C6 0.7(11) . . . . ?
C5 C7 C8 C9 -178.1(7) 3_666 . . . ?
C5 C7 C6 C5 -4.4(11) 3_666 . . . ?
C5 C7 C6 C12 178.5(6) 3_666 . . . ?
C5 C4 C3 C2 0.1(11) . . . . ?
C11 N1 C1 O1 178.8(7) . . . . ?
C11 N1 C1 C2 -3.8(11) . . . . ?
C11 N1 C13 C14 -124.8(8) . . . . ?
C11 N1 C13 C18 55.9(10) . . . . ?
C11 C10 C9 C8 178.0(7) . . . . ?
C11 C10 C12 C2 3.2(11) . . . . ?
C11 C10 C12 C6 -177.5(7) . . . . ?
C15 C16 C17 C18 -0.2(14) . . . . ?
C4 C5 C6 C7 -176.8(6) . . . . ?
C4 C5 C6 C12 0.1(11) . . . . ?
C12 C10 C9 C8 -0.4(12) . . . . ?
C12 C10 C11 O2 173.4(8) . . . . ?
C12 C10 C11 N1 -3.5(11) . . . . ?
C12 C2 C3 C4 0.7(11) . . . . ?
C3 C2 C12 C10 178.3(7) . . . . ?
C3 C2 C12 C6 -1.0(10) . . . . ?
C6 C7 C8 C9 -1.9(11) . . . . ?
C6 C5 C4 C3 -0.5(11) . . . . ?
C13 N1 C1 O1 -2.9(11) . . . . ?
C13 N1 C1 C2 174.5(6) . . . . ?
C13 N1 C11 O2 8.6(11) . . . . ?
C13 N1 C11 C10 -174.5(7) . . . . ?
C13 C18 C17 C16 0.2(12) . . . . ?
C14 C15 C16 C17 -0.1(15) . . . . ?
C14 C13 C18 C17 0.0(13) . . . . ?
C16 C15 C14 C13 0.3(14) . . . . ?
C18 C13 C14 C15 -0.3(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_PTCDI_Ph_220K
_database_code_depnum_ccdc_archive 'CCDC 2253197'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PTCDI_Ph_220K       
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      55.00 Degree
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_RINTA01_PTCDI_Ph_220K       
;
PROBLEM: The value of Rint is greater than 0.18
            Rint given   0.183	
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_PLAT020_PTCDI_Ph_220K       
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.183 Report
RESPONSE: The investigated single crystal was small, brittle and poorly 
diffractive. Multiple data sets were collected on single crystals from 
different batches, one of which of the highest quality is presented in 
this paper. Attempts to collect higher quality data at low temperatures
were unsuccessful.
;
_vrf_PLAT026_PTCDI_Ph_220K       
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        32% Check 
RESPONSE: This low value comes from the overall poor diffraction quality of the 
crystal.
;
# end Validation Reply Form

loop_
_audit_creation_date
2022-11-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.7581(13)
_cell_length_b                   3.9442(4)
_cell_length_c                   18.3139(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.635(7)
_cell_angle_gamma                90
_cell_volume                     1196.78(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    450
_cell_measurement_temperature    219.9(3)
_cell_measurement_theta_max      67.7910
_cell_measurement_theta_min      2.6550
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -3 -1 0.0543
0 0 12 0.0089
1 0 -12 0.0287
11 0 -1 0.0708
0 3 -2 0.0708
-11 0 1 0.0208

_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1827
_diffrn_reflns_av_unetI/netI     0.2097
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4605
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        55.000
_diffrn_reflns_theta_max         73.381
_diffrn_reflns_theta_min         2.667
_diffrn_ambient_temperature      220.15
_diffrn_detector_area_resol_mean 10.5384
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
 Data were collected at temperature of 220 K
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                747
_reflns_number_total             2333
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.00053(16)
_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   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2166
_refine_ls_R_factor_gt           0.0857
_refine_ls_restrained_S_all      0.934
_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)+(0.0117P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.2340
_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:
 C8(H3), C9(H4), C15(H6), C4(H2), C3(H1), C14(H5), C16(H7), C18(H9), C17(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8303(2) 0.0525(13) 0.6567(2) 0.0538(14) Uani 1 1 d . . . . .
O1 O 0.6852(2) 0.6086(12) 0.8117(2) 0.0478(13) Uani 1 1 d . . . . .
N1 N 0.7611(3) 0.3485(14) 0.7347(3) 0.0366(14) Uani 1 1 d . . . . .
C10 C 0.7023(3) 0.2663(17) 0.6043(3) 0.0359(15) Uani 1 1 d . . . . .
C7 C 0.5742(3) 0.3403(16) 0.4869(3) 0.0357(15) Uani 1 1 d . . . . .
C1 C 0.6928(3) 0.5034(18) 0.7499(3) 0.0416(17) Uani 1 1 d . . . . .
C8 C 0.6455(3) 0.1925(16) 0.4769(3) 0.0402(16) Uani 1 1 d . . . . .
H3 H 0.651452 0.117739 0.429264 0.048 Uiso 1 1 calc R U . . .
C2 C 0.6245(3) 0.5472(16) 0.6874(3) 0.0336(14) Uani 1 1 d . . . . .
C9 C 0.7105(3) 0.1468(17) 0.5346(3) 0.0423(17) Uani 1 1 d . . . . .
H4 H 0.758200 0.038301 0.526005 0.051 Uiso 1 1 calc R U . . .
C5 C 0.4948(3) 0.6236(16) 0.5723(3) 0.0324(14) Uani 1 1 d . . . . .
C11 C 0.7709(3) 0.2102(18) 0.6650(3) 0.0395(16) Uani 1 1 d . . . . .
C15 C 0.8876(4) 0.161(2) 0.9156(4) 0.055(2) Uani 1 1 d . . . . .
H6 H 0.882790 0.058241 0.961080 0.066 Uiso 1 1 calc R U . . .
C4 C 0.4904(3) 0.7477(17) 0.6430(3) 0.0388(16) Uani 1 1 d . . . . .
H2 H 0.443238 0.856801 0.652799 0.047 Uiso 1 1 calc R U . . .
C12 C 0.6315(3) 0.4234(16) 0.6168(3) 0.0320(14) Uani 1 1 d . . . . .
C3 C 0.5565(3) 0.7093(17) 0.6997(3) 0.0395(16) Uani 1 1 d . . . . .
H1 H 0.553378 0.797624 0.746864 0.047 Uiso 1 1 calc R U . . .
C6 C 0.5653(3) 0.4632(16) 0.5585(3) 0.0317(14) Uani 1 1 d . . . . .
C13 C 0.8313(3) 0.3270(18) 0.7941(3) 0.0383(16) Uani 1 1 d . . . . .
C14 C 0.8210(4) 0.1700(19) 0.8603(4) 0.0495(19) Uani 1 1 d . . . . .
H5 H 0.771258 0.074928 0.867269 0.059 Uiso 1 1 calc R U . . .
C16 C 0.9599(4) 0.297(2) 0.9049(4) 0.054(2) Uani 1 1 d . . . . .
H7 H 1.003928 0.288063 0.943232 0.065 Uiso 1 1 calc R U . . .
C18 C 0.9027(4) 0.4626(18) 0.7831(4) 0.0466(18) Uani 1 1 d . . . . .
H9 H 0.907527 0.566550 0.737752 0.056 Uiso 1 1 calc R U . . .
C17 C 0.9692(4) 0.4486(19) 0.8389(4) 0.056(2) Uani 1 1 d . . . . .
H8 H 1.019216 0.540153 0.831636 0.067 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
O2 C11 1.203(7) . ?
O1 C1 1.229(7) . ?
N1 C1 1.363(7) . ?
N1 C11 1.421(7) . ?
N1 C13 1.479(7) . ?
C10 C9 1.386(8) . ?
C10 C11 1.491(8) . ?
C10 C12 1.388(8) . ?
C7 C8 1.366(8) . ?
C7 C5 1.469(7) 3_666 ?
C7 C6 1.427(8) . ?
C1 C2 1.502(8) . ?
C8 H3 0.9400 . ?
C8 C9 1.412(8) . ?
C2 C12 1.403(8) . ?
C2 C3 1.355(8) . ?
C9 H4 0.9400 . ?
C5 C4 1.397(7) . ?
C5 C6 1.395(7) . ?
C15 H6 0.9400 . ?
C15 C14 1.389(8) . ?
C15 C16 1.367(9) . ?
C4 H2 0.9400 . ?
C4 C3 1.408(7) . ?
C12 C6 1.428(7) . ?
C3 H1 0.9400 . ?
C13 C14 1.396(8) . ?
C13 C18 1.353(8) . ?
C14 H5 0.9400 . ?
C16 H7 0.9400 . ?
C16 C17 1.378(9) . ?
C18 H9 0.9400 . ?
C18 C17 1.396(8) . ?
C17 H8 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 124.7(5) . . ?
C1 N1 C13 118.4(5) . . ?
C11 N1 C13 116.9(5) . . ?
C9 C10 C11 117.6(5) . . ?
C9 C10 C12 120.7(5) . . ?
C12 C10 C11 121.7(5) . . ?
C8 C7 C5 123.3(6) . 3_666 ?
C8 C7 C6 118.9(5) . . ?
C6 C7 C5 117.8(5) . 3_666 ?
O1 C1 N1 123.0(6) . . ?
O1 C1 C2 119.4(6) . . ?
N1 C1 C2 117.6(5) . . ?
C7 C8 H3 118.4 . . ?
C7 C8 C9 123.1(6) . . ?
C9 C8 H3 118.4 . . ?
C12 C2 C1 120.2(5) . . ?
C3 C2 C1 119.4(6) . . ?
C3 C2 C12 120.4(5) . . ?
C10 C9 C8 118.2(6) . . ?
C10 C9 H4 120.9 . . ?
C8 C9 H4 120.9 . . ?
C4 C5 C7 120.3(5) . 3_666 ?
C6 C5 C7 120.3(5) . 3_666 ?
C6 C5 C4 119.4(5) . . ?
O2 C11 N1 121.4(6) . . ?
O2 C11 C10 122.9(6) . . ?
N1 C11 C10 115.7(5) . . ?
C14 C15 H6 119.4 . . ?
C16 C15 H6 119.4 . . ?
C16 C15 C14 121.1(7) . . ?
C5 C4 H2 120.0 . . ?
C5 C4 C3 120.0(6) . . ?
C3 C4 H2 120.0 . . ?
C10 C12 C2 120.0(5) . . ?
C10 C12 C6 120.9(5) . . ?
C2 C12 C6 119.2(5) . . ?
C2 C3 C4 121.1(6) . . ?
C2 C3 H1 119.4 . . ?
C4 C3 H1 119.4 . . ?
C7 C6 C12 118.2(5) . . ?
C5 C6 C7 121.9(5) . . ?
C5 C6 C12 119.9(5) . . ?
C14 C13 N1 118.4(5) . . ?
C18 C13 N1 119.5(6) . . ?
C18 C13 C14 122.2(6) . . ?
C15 C14 C13 117.0(7) . . ?
C15 C14 H5 121.5 . . ?
C13 C14 H5 121.5 . . ?
C15 C16 H7 119.5 . . ?
C15 C16 C17 121.1(6) . . ?
C17 C16 H7 119.5 . . ?
C13 C18 H9 119.9 . . ?
C13 C18 C17 120.1(7) . . ?
C17 C18 H9 119.9 . . ?
C16 C17 C18 118.4(7) . . ?
C16 C17 H8 120.8 . . ?
C18 C17 H8 120.8 . . ?

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
O1 C1 C2 C12 -178.9(6) . . . . ?
O1 C1 C2 C3 1.6(10) . . . . ?
N1 C1 C2 C12 1.6(9) . . . . ?
N1 C1 C2 C3 -178.0(6) . . . . ?
N1 C13 C14 C15 -178.6(6) . . . . ?
N1 C13 C18 C17 179.1(6) . . . . ?
C10 C12 C6 C7 -0.6(9) . . . . ?
C10 C12 C6 C5 -179.7(6) . . . . ?
C7 C8 C9 C10 -1.8(10) . . . . ?
C7 C5 C4 C3 179.4(6) 3_666 . . . ?
C7 C5 C6 C7 2.2(10) 3_666 . . . ?
C7 C5 C6 C12 -178.8(6) 3_666 . . . ?
C1 N1 C11 O2 -173.9(6) . . . . ?
C1 N1 C11 C10 4.6(9) . . . . ?
C1 N1 C13 C14 56.9(9) . . . . ?
C1 N1 C13 C18 -122.2(7) . . . . ?
C1 C2 C12 C10 -1.4(9) . . . . ?
C1 C2 C12 C6 179.0(6) . . . . ?
C1 C2 C3 C4 -178.3(6) . . . . ?
C8 C7 C6 C5 178.5(6) . . . . ?
C8 C7 C6 C12 -0.5(9) . . . . ?
C2 C12 C6 C7 179.0(6) . . . . ?
C2 C12 C6 C5 0.0(9) . . . . ?
C9 C10 C11 O2 -3.9(10) . . . . ?
C9 C10 C11 N1 177.6(6) . . . . ?
C9 C10 C12 C2 -179.1(6) . . . . ?
C9 C10 C12 C6 0.5(10) . . . . ?
C5 C7 C8 C9 -177.5(6) 3_666 . . . ?
C5 C7 C6 C5 -2.1(10) 3_666 . . . ?
C5 C7 C6 C12 178.8(6) 3_666 . . . ?
C5 C4 C3 C2 -1.3(10) . . . . ?
C11 N1 C1 O1 177.1(6) . . . . ?
C11 N1 C1 C2 -3.4(10) . . . . ?
C11 N1 C13 C14 -124.3(7) . . . . ?
C11 N1 C13 C18 56.6(9) . . . . ?
C11 C10 C9 C8 178.8(6) . . . . ?
C11 C10 C12 C2 2.8(10) . . . . ?
C11 C10 C12 C6 -177.6(6) . . . . ?
C15 C16 C17 C18 0.7(12) . . . . ?
C4 C5 C6 C7 -178.2(6) . . . . ?
C4 C5 C6 C12 0.9(9) . . . . ?
C12 C10 C9 C8 0.6(10) . . . . ?
C12 C10 C11 O2 174.3(7) . . . . ?
C12 C10 C11 N1 -4.2(9) . . . . ?
C12 C2 C3 C4 2.1(10) . . . . ?
C3 C2 C12 C10 178.2(6) . . . . ?
C3 C2 C12 C6 -1.5(9) . . . . ?
C6 C7 C8 C9 1.7(10) . . . . ?
C6 C5 C4 C3 -0.2(9) . . . . ?
C13 N1 C1 O1 -4.3(10) . . . . ?
C13 N1 C1 C2 175.2(6) . . . . ?
C13 N1 C11 O2 7.4(10) . . . . ?
C13 N1 C11 C10 -174.0(6) . . . . ?
C13 C18 C17 C16 -0.6(11) . . . . ?
C14 C15 C16 C17 -0.2(12) . . . . ?
C14 C13 C18 C17 0.0(11) . . . . ?
C16 C15 C14 C13 -0.4(12) . . . . ?
C18 C13 C14 C15 0.5(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_PTCDI_Ph_350K
_database_code_depnum_ccdc_archive 'CCDC 2253199'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_PTCDI_Ph_350K       
;
PROBLEM: The value of Rint is greater than 0.25
            Rint given   0.336
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
_vrf_PLAT020_PTCDI_Ph_350K       
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.336 Report
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
_vrf_PLAT026_PTCDI_Ph_350K       
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         9% Check 
RESPONSE: This low value comes from the overall poor diffraction quality of 
the crystal.
;
_vrf_PLAT027_PTCDI_Ph_350K       
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      50.00 Degree
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
_vrf_PLAT340_PTCDI_Ph_350K       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01775 Ang.  
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-03-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.706(3)
_cell_length_b                   4.0610(6)
_cell_length_c                   18.291(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.37(2)
_cell_angle_gamma                90
_cell_volume                     1227.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    112
_cell_measurement_temperature    623.15
_cell_measurement_theta_max      54.3560
_cell_measurement_theta_min      2.6410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.3358
_diffrn_reflns_av_unetI/netI     0.9179
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3987
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        50.000
_diffrn_reflns_theta_max         70.989
_diffrn_reflns_theta_min         2.673
_diffrn_ambient_temperature      623.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
 Data were collected at temperature of 350 K
;
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                205
_reflns_number_total             2218
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.794
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2218
_refine_ls_number_restraints     255
_refine_ls_R_factor_all          0.5648
_refine_ls_R_factor_gt           0.1400
_refine_ls_restrained_S_all      0.769
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.2552
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C9-C10 \\sim C9-C8 \\sim C8-C7 \\sim C6-C12 \\sim C7-C6 \\sim C12-C10 \\sim
C2-C12 \\sim C3-C2 \\sim C4-C3 ~
 C5-C4 \\sim C6-C5 \\sim C2-C1 \\sim C11-C10
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C16, O2, C11, N1, C10, C1, C13, C9, C12, O1, C2, C14, C18, C8, C6, C3, C15,
 C17, C7, C5, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C10, C11, C12, N1, C2, C1, C7, C9, C8, C6, C5, C4, C3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C18, C14, C15, C17, C13, C16
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O2, C11, N1, C1, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C4(H4), C3(H3), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
4.b Fitted hexagon refined as free rotating group:
 C11(C10,C12,C2,C1,N1), C13(C14,C15,C16,C17,C18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8297(6) 0.048(3) 0.6591(5) 0.120(5) Uani 1 1 d . . . . .
O1 O 0.6861(5) 0.611(3) 0.8123(5) 0.097(4) Uani 1 1 d . . . . .
C7 C 0.5741(10) 0.344(4) 0.4890(9) 0.076(5) Uani 1 1 d D . . . .
C8 C 0.6446(8) 0.184(4) 0.4771(8) 0.094(7) Uani 1 1 d D . . . .
H8 H 0.650155 0.105868 0.430355 0.113 Uiso 1 1 calc R U . . .
C9 C 0.7072(9) 0.143(4) 0.5360(6) 0.094(6) Uani 1 1 d D . . . .
H9 H 0.753228 0.031830 0.526602 0.113 Uiso 1 1 calc R U . . .
C5 C 0.4957(11) 0.611(4) 0.5719(8) 0.076(5) Uani 1 1 d D . . . .
C11 C 0.7684(6) 0.219(2) 0.6661(8) 0.089(7) Uani 1 1 d DG . . . .
C10 C 0.7058(9) 0.257(3) 0.6077(5) 0.090(6) Uani 1 1 d DG . . . .
C12 C 0.6354(7) 0.420(3) 0.6187(6) 0.092(6) Uani 1 1 d DG . . . .
C2 C 0.6276(5) 0.545(2) 0.6881(8) 0.099(7) Uani 1 1 d DG . . . .
C1 C 0.6903(8) 0.507(3) 0.7464(5) 0.106(8) Uani 1 1 d DG . . . .
N1 N 0.7606(6) 0.344(3) 0.7354(6) 0.082(4) Uani 1 1 d G . . . .
C4 C 0.4914(8) 0.741(4) 0.6421(7) 0.095(7) Uani 1 1 d D . . . .
H4 H 0.444411 0.845647 0.651675 0.114 Uiso 1 1 calc R U . . .
C3 C 0.5580(7) 0.714(3) 0.6980(8) 0.080(6) Uani 1 1 d D . . . .
H3 H 0.555371 0.813005 0.743447 0.095 Uiso 1 1 calc R U . . .
C6 C 0.5713(8) 0.474(4) 0.5609(7) 0.067(5) Uani 1 1 d D . . . .
C13 C 0.8310(6) 0.331(3) 0.7915(6) 0.088(6) Uani 1 1 d G . . . .
C14 C 0.8213(5) 0.174(2) 0.8572(7) 0.098(6) Uani 1 1 d G . . . .
H14 H 0.771744 0.080454 0.862819 0.117 Uiso 1 1 calc R U . . .
C15 C 0.8857(8) 0.157(2) 0.9145(5) 0.122(8) Uani 1 1 d G . . . .
H15 H 0.879178 0.051941 0.958485 0.147 Uiso 1 1 calc R U . . .
C16 C 0.9598(6) 0.297(3) 0.9062(6) 0.117(8) Uani 1 1 d G . . . .
H16 H 1.002820 0.285195 0.944519 0.140 Uiso 1 1 calc R U . . .
C17 C 0.9695(5) 0.453(2) 0.8405(8) 0.130(8) Uani 1 1 d G . . . .
H17 H 1.019027 0.546960 0.834886 0.156 Uiso 1 1 calc R U . . .
C18 C 0.9051(8) 0.471(2) 0.7832(5) 0.092(6) Uani 1 1 d G . . . .
H18 H 0.911594 0.575477 0.739219 0.110 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
O2 C11 1.258(11) . ?
O1 C1 1.287(11) . ?
C7 C8 1.388(11) . ?
C7 C5 1.503(14) 3_666 ?
C7 C6 1.424(11) . ?
C8 H8 0.9300 . ?
C8 C9 1.397(10) . ?
C9 H9 0.9300 . ?
C9 C10 1.394(10) . ?
C5 C4 1.400(11) . ?
C5 C6 1.422(11) . ?
C11 C10 1.3900 . ?
C11 N1 1.3900 . ?
C10 C12 1.3900 . ?
C12 C2 1.3900 . ?
C12 C6 1.408(10) . ?
C2 C1 1.3900 . ?
C2 C3 1.385(11) . ?
C1 N1 1.3900 . ?
N1 C13 1.445(8) . ?
C4 H4 0.9300 . ?
C4 C3 1.402(10) . ?
C3 H3 0.9300 . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C14 H14 0.9300 . ?
C14 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C16 1.3900 . ?
C16 H16 0.9300 . ?
C16 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C18 1.3900 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C7 C5 121.6(17) . 3_666 ?
C8 C7 C6 117.4(18) . . ?
C6 C7 C5 120.9(13) . 3_666 ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.4(16) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 117.5 . . ?
C10 C9 C8 125.0(15) . . ?
C10 C9 H9 117.5 . . ?
C4 C5 C7 119.8(17) . 3_666 ?
C4 C5 C6 116.4(17) . . ?
C6 C5 C7 123.5(12) . 3_666 ?
O2 C11 C10 121.1(13) . . ?
O2 C11 N1 118.7(13) . . ?
C10 C11 N1 120.0 . . ?
C11 C10 C9 124.9(14) . . ?
C12 C10 C9 115.1(14) . . ?
C12 C10 C11 120.0 . . ?
C10 C12 C6 122.1(14) . . ?
C2 C12 C10 120.0 . . ?
C2 C12 C6 117.8(14) . . ?
C12 C2 C1 120.0 . . ?
C3 C2 C12 119.5(14) . . ?
C3 C2 C1 120.5(14) . . ?
O1 C1 C2 123.0(13) . . ?
O1 C1 N1 117.0(13) . . ?
C2 C1 N1 120.0 . . ?
C11 N1 C13 117.4(12) . . ?
C1 N1 C11 120.0 . . ?
C1 N1 C13 122.2(12) . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.8(15) . . ?
C3 C4 H4 120.1 . . ?
C2 C3 C4 122.5(14) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C6 C7 115.2(12) . . ?
C12 C6 C7 120.8(17) . . ?
C12 C6 C5 123.2(17) . . ?
C14 C13 N1 116.4(12) . . ?
C14 C13 C18 120.0 . . ?
C18 C13 N1 123.5(12) . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 H18 120.0 . . ?

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
O2 C11 C10 C9 -6.4(15) . . . . ?
O2 C11 C10 C12 173.9(12) . . . . ?
O2 C11 N1 C1 -174.0(12) . . . . ?
O2 C11 N1 C13 13.1(13) . . . . ?
O1 C1 N1 C11 178.6(12) . . . . ?
O1 C1 N1 C13 -8.8(12) . . . . ?
C7 C8 C9 C10 -1(3) . . . . ?
C7 C5 C4 C3 -176.8(15) 3_666 . . . ?
C7 C5 C6 C7 -7(3) 3_666 . . . ?
C7 C5 C6 C12 -177.5(12) 3_666 . . . ?
C8 C7 C6 C5 -175.3(14) . . . . ?
C8 C7 C6 C12 -5(3) . . . . ?
C8 C9 C10 C11 -179.4(12) . . . . ?
C8 C9 C10 C12 0(2) . . . . ?
C9 C10 C12 C2 -179.7(12) . . . . ?
C9 C10 C12 C6 -1.6(13) . . . . ?
C5 C7 C8 C9 -178.8(15) 3_666 . . . ?
C5 C7 C6 C5 7(3) 3_666 . . . ?
C5 C7 C6 C12 177.5(11) 3_666 . . . ?
C5 C4 C3 C2 -4(3) . . . . ?
C11 C10 C12 C2 0.0 . . . . ?
C11 C10 C12 C6 178.1(12) . . . . ?
C11 N1 C13 C14 -124.9(6) . . . . ?
C11 N1 C13 C18 56.4(10) . . . . ?
C10 C11 N1 C1 0.0 . . . . ?
C10 C11 N1 C13 -172.9(10) . . . . ?
C10 C12 C2 C1 0.0 . . . . ?
C10 C12 C2 C3 178.5(12) . . . . ?
C10 C12 C6 C7 4(2) . . . . ?
C10 C12 C6 C5 173.7(12) . . . . ?
C12 C2 C1 O1 -178.5(12) . . . . ?
C12 C2 C1 N1 0.0 . . . . ?
C12 C2 C3 C4 6(2) . . . . ?
C2 C12 C6 C7 -178.0(12) . . . . ?
C2 C12 C6 C5 -8.1(19) . . . . ?
C2 C1 N1 C11 0.0 . . . . ?
C2 C1 N1 C13 172.6(10) . . . . ?
C1 C2 C3 C4 -176.0(13) . . . . ?
C1 N1 C13 C14 62.4(9) . . . . ?
C1 N1 C13 C18 -116.3(8) . . . . ?
N1 C11 C10 C9 179.7(14) . . . . ?
N1 C11 C10 C12 0.0 . . . . ?
N1 C13 C14 C15 -178.7(10) . . . . ?
N1 C13 C18 C17 178.6(10) . . . . ?
C4 C5 C6 C7 -179.9(14) . . . . ?
C4 C5 C6 C12 10(2) . . . . ?
C3 C2 C1 O1 3.0(13) . . . . ?
C3 C2 C1 N1 -178.5(12) . . . . ?
C6 C7 C8 C9 3(3) . . . . ?
C6 C5 C4 C3 -4(3) . . . . ?
C6 C12 C2 C1 -178.2(11) . . . . ?
C6 C12 C2 C3 0.3(13) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C13 0.0 . . . . ?
C18 C13 C14 C15 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_PTCDI_Ph_490K
_database_code_depnum_ccdc_archive 'CCDC 2253201'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_ATOM007_PTCDI_Ph_490K       
;
PROBLEM: _atom_site_aniso_label is missing
            Unique label identifying the atom site.
RESPONSE: The structure was refined isotropically because of the overall 
poor diffraction quality of the crystal. Furthermore, these data come from 
high-temperature studies and the poor quality of the data is related to the 
progressive build-up of thermal motions.
;
_vrf_RINTA01_PTCDI_Ph_490K       
;
PROBLEM: The value of Rint is greater than 0.25
            Rint given   0.534
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
_vrf_THETM01_PTCDI_Ph_490K       
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.4987
RESPONSE: Because of the weak diffraction produced by these crystals,
data was truncated to include only the part where reflections were 
observed. 
;
_vrf_PLAT020_PTCDI_Ph_490K       
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.534 Report
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
_vrf_PLAT026_PTCDI_Ph_490K       
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         6% Check  
RESPONSE: This low value comes from the overall poor diffraction quality of 
the crystal.
;
_vrf_PLAT027_PTCDI_Ph_490K       
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      50.00 Degree
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
_vrf_PLAT029_PTCDI_Ph_490K       
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.873 Why?  
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
_vrf_PLAT201_PTCDI_Ph_490K       
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         21 Report
              O1        O2        N1        C1        C2                  etc.  
RESPONSE: The structure was refined isotropically because of the overall 
poor diffraction quality of the crystal. Furthermore, these data come from 
high-temperature studies and the poor quality of the data is related to the 
progressive build-up of thermal motions.
;
_vrf_PLAT149_PTCDI_Ph_490K       
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.19 Degree
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
_vrf_PLAT340_PTCDI_Ph_490K       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.0345 Ang.   
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
_vrf_PLAT245_PTCDI_Ph_490K       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.499        168 Report
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-03-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.52(3)
_cell_length_b                   4.344(4)
_cell_length_c                   17.92(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.10(19)
_cell_angle_gamma                90
_cell_volume                     1276(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    92
_cell_measurement_temperature    491(10)
_cell_measurement_theta_max      46.0720
_cell_measurement_theta_min      2.7170
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.834
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -12 0.0011
0 0 12 0.0238
0 -3 1 0.1043
-11 0 1 0.0154
0 3 -1 0.1446
11 0 -1 0.0098

_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.5343
_diffrn_reflns_av_unetI/netI     1.0868
_diffrn_reflns_Laue_measured_fraction_full 0.873
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2854
_diffrn_reflns_point_group_measured_fraction_full 0.873
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        50.000
_diffrn_reflns_theta_max         50.256
_diffrn_reflns_theta_min         2.695
_diffrn_ambient_temperature      491.15
_diffrn_detector_area_resol_mean 8.0296
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.873
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_details      
;
 Data were collected at temperature of 490 K
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                64
_reflns_number_total             1154
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.086
_refine_diff_density_min         -0.107
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.649
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     63
_refine_ls_number_reflns         1154
_refine_ls_number_restraints     103
_refine_ls_R_factor_all          0.6602
_refine_ls_R_factor_gt           0.0885
_refine_ls_restrained_S_all      0.639
_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)+(0.0010P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.2868
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N1-C13
 1.4 with sigma of 0.05
 C13-C1 \\sim C13-C11
 with sigma of 0.02
 C11-C10 \\sim C12-C10 \\sim C9-C10 \\sim C9-C8 \\sim C8-C7 \\sim C7-C6 \\sim
C6-C12 \\sim C6-C5 \\sim C5-C4 ~
 C4-C3 \\sim C3-C2 \\sim C2-C12 \\sim C2-C1
 with sigma of 0.02
 C18-C11 \\sim C14-C1
 with sigma of 0.02
 N1-C12 \\sim C7-C10 \\sim C5-C2
 with sigma of 0.02
 C11-C10 \\sim C9-C10 \\sim C9-C8 \\sim C8-C7 \\sim C7-C6 \\sim C6-C12 \\sim
C12-C10 \\sim C2-C1 \\sim C2-C12
 \\sim C3-C2 \\sim C4-C3 \\sim C6-C5 \\sim C5-C4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
C7 \\sim C6 \\sim C5 \\sim C4 \\sim C3 \\sim C2 \\sim C12 \\sim C10 \\sim C9
\\sim C8 \\sim C11 \\sim C1: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
4.b Fitted hexagon refined as free rotating group:
 C1(N1,C11,C10,C12,C2), C14(C15,C16,C17,C18,C13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8307(14) 0.044(4) 0.6595(11) 0.248(12) Uiso 1 1 d . . . . .
O1 O 0.6869(12) 0.625(4) 0.8090(14) 0.224(11) Uiso 1 1 d . . . . .
C1 C 0.6910(9) 0.518(4) 0.7430(14) 0.265(19) Uiso 1 1 d DG U . . .
N1 N 0.7601(8) 0.348(4) 0.7331(9) 0.256(14) Uiso 1 1 d DG . . . .
C11 C 0.7671(11) 0.212(4) 0.6640(9) 0.249(18) Uiso 1 1 d DG U . . .
C10 C 0.7050(16) 0.246(6) 0.6048(10) 0.252(14) Uiso 1 1 d DG U . . .
C12 C 0.6359(13) 0.417(6) 0.6147(16) 0.271(16) Uiso 1 1 d DG U . . .
C2 C 0.6289(8) 0.553(5) 0.6838(19) 0.232(14) Uiso 1 1 d DG U . . .
C7 C 0.5730(15) 0.328(8) 0.492(2) 0.188(13) Uiso 1 1 d D U . . .
C8 C 0.641(2) 0.167(7) 0.4770(16) 0.206(13) Uiso 1 1 d D U . . .
H8 H 0.644974 0.095969 0.428607 0.247 Uiso 1 1 calc R U . . .
C9 C 0.704(2) 0.110(6) 0.5348(17) 0.254(16) Uiso 1 1 d D U . . .
H9 H 0.745492 -0.023183 0.526136 0.304 Uiso 1 1 calc R U . . .
C6 C 0.5648(17) 0.452(9) 0.5630(19) 0.238(15) Uiso 1 1 d D U . . .
C5 C 0.498(2) 0.648(9) 0.5698(14) 0.241(15) Uiso 1 1 d D U . . .
C3 C 0.5610(18) 0.731(6) 0.6980(16) 0.213(15) Uiso 1 1 d D U . . .
H3 H 0.560729 0.828918 0.744129 0.256 Uiso 1 1 calc R U . . .
C4 C 0.4933(18) 0.761(6) 0.6419(17) 0.194(14) Uiso 1 1 d D U . . .
H4 H 0.445723 0.855048 0.652960 0.232 Uiso 1 1 calc R U . . .
C14 C 0.8185(9) 0.179(4) 0.8560(10) 0.300(16) Uiso 1 1 d DG U . . .
H14 H 0.768443 0.089017 0.861312 0.360 Uiso 1 1 calc R U . . .
C15 C 0.8833(12) 0.150(4) 0.9129(8) 0.288(16) Uiso 1 1 d G U . . .
H15 H 0.876545 0.040344 0.956330 0.346 Uiso 1 1 calc R U . . .
C16 C 0.9581(10) 0.284(4) 0.9049(10) 0.299(16) Uiso 1 1 d G U . . .
H16 H 1.001473 0.264002 0.942999 0.358 Uiso 1 1 calc R U . . .
C17 C 0.9682(8) 0.447(4) 0.8400(12) 0.257(15) Uiso 1 1 d G U . . .
H17 H 1.018300 0.536336 0.834650 0.309 Uiso 1 1 calc R U . . .
C18 C 0.9035(10) 0.476(3) 0.7831(9) 0.212(13) Uiso 1 1 d DG U . . .
H18 H 0.910200 0.585012 0.739631 0.255 Uiso 1 1 calc R U . . .
C13 C 0.8286(8) 0.342(4) 0.7911(9) 0.238(14) Uiso 1 1 d DG 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
O2 C11 1.29(3) . ?
O1 C1 1.28(3) . ?
C1 N1 1.3900 . ?
C1 C2 1.3900 . ?
N1 C11 1.3900 . ?
N1 C13 1.438(14) . ?
C11 C10 1.3900 . ?
C10 C12 1.3900 . ?
C10 C9 1.387(14) . ?
C12 C2 1.3900 . ?
C12 C6 1.411(14) . ?
C2 C3 1.412(14) . ?
C7 C8 1.377(14) . ?
C7 C6 1.406(14) . ?
C7 C5 1.52(3) 3_666 ?
C8 H8 0.9300 . ?
C8 C9 1.392(14) . ?
C9 H9 0.9300 . ?
C6 C5 1.405(14) . ?
C5 C4 1.395(14) . ?
C3 H3 0.9300 . ?
C3 C4 1.414(14) . ?
C4 H4 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.3900 . ?
C14 C13 1.3900 . ?
C15 H15 0.9300 . ?
C15 C16 1.3900 . ?
C16 H16 0.9300 . ?
C16 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C13 1.3900 . ?

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
O1 C1 N1 116.7(15) . . ?
O1 C1 C2 123.3(15) . . ?
N1 C1 C2 120.0 . . ?
C1 N1 C13 120.2(8) . . ?
C11 N1 C1 120.0 . . ?
C11 N1 C13 119.4(8) . . ?
O2 C11 N1 117.1(14) . . ?
O2 C11 C10 122.8(13) . . ?
C10 C11 N1 120.0 . . ?
C11 C10 C12 120.0 . . ?
C9 C10 C11 125(3) . . ?
C9 C10 C12 115(3) . . ?
C10 C12 C6 127(4) . . ?
C2 C12 C10 120.0 . . ?
C2 C12 C6 113(4) . . ?
C1 C2 C3 117(3) . . ?
C12 C2 C1 120.0 . . ?
C12 C2 C3 123(3) . . ?
C8 C7 C6 123(3) . . ?
C8 C7 C5 118(5) . 3_666 ?
C6 C7 C5 119(3) . 3_666 ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 120(3) . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 122(3) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C7 C6 C12 113(4) . . ?
C5 C6 C12 127(4) . . ?
C5 C6 C7 118(2) . . ?
C6 C5 C7 122(3) . 3_666 ?
C4 C5 C7 121(5) . 3_666 ?
C4 C5 C6 116(3) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 120(2) . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C15 C14 H14 120.0 . . ?
C15 C14 C13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C13 120.0 . . ?
C13 C18 H18 120.0 . . ?
C14 C13 N1 116.6(12) . . ?
C18 C13 N1 123.3(12) . . ?
C18 C13 C14 120.0 . . ?

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
O2 C11 C10 C12 176(2) . . . . ?
O2 C11 C10 C9 0(3) . . . . ?
O1 C1 N1 C11 177(2) . . . . ?
O1 C1 N1 C13 -11(2) . . . . ?
O1 C1 C2 C12 -177(2) . . . . ?
O1 C1 C2 C3 4(2) . . . . ?
C1 N1 C11 O2 -177(2) . . . . ?
C1 N1 C11 C10 0.0 . . . . ?
C1 N1 C13 C14 71.4(15) . . . . ?
C1 N1 C13 C18 -111.8(11) . . . . ?
C1 C2 C3 C4 -176(2) . . . . ?
N1 C1 C2 C12 0.0 . . . . ?
N1 C1 C2 C3 -180(2) . . . . ?
N1 C11 C10 C12 0.0 . . . . ?
N1 C11 C10 C9 -177(3) . . . . ?
C11 N1 C13 C14 -116.0(11) . . . . ?
C11 N1 C13 C18 60.8(17) . . . . ?
C11 C10 C12 C2 0.0 . . . . ?
C11 C10 C12 C6 -174(3) . . . . ?
C11 C10 C9 C8 -177(2) . . . . ?
C10 C12 C2 C1 0.0 . . . . ?
C10 C12 C2 C3 180(2) . . . . ?
C10 C12 C6 C7 -9(5) . . . . ?
C10 C12 C6 C5 -173(4) . . . . ?
C12 C10 C9 C8 6(4) . . . . ?
C12 C2 C3 C4 4(4) . . . . ?
C12 C6 C5 C7 177(3) . . . 3_666 ?
C12 C6 C5 C4 -17(8) . . . . ?
C2 C1 N1 C11 0.0 . . . . ?
C2 C1 N1 C13 172.6(17) . . . . ?
C2 C12 C6 C7 177(3) . . . . ?
C2 C12 C6 C5 12(6) . . . . ?
C2 C3 C4 C5 -8(5) . . . . ?
C7 C8 C9 C10 -9(6) . . . . ?
C7 C6 C5 C7 14(9) . . . 3_666 ?
C7 C6 C5 C4 180(3) . . . . ?
C7 C5 C4 C3 179(3) 3_666 . . . ?
C8 C7 C6 C12 5(7) . . . . ?
C8 C7 C6 C5 171(3) . . . . ?
C9 C10 C12 C2 177(2) . . . . ?
C9 C10 C12 C6 3(3) . . . . ?
C6 C12 C2 C1 175(2) . . . . ?
C6 C12 C2 C3 -6(3) . . . . ?
C6 C7 C8 C9 3(7) . . . . ?
C6 C5 C4 C3 14(7) . . . . ?
C5 C7 C8 C9 -173(3) 3_666 . . . ?
C5 C7 C6 C12 -179(2) 3_666 . . . ?
C5 C7 C6 C5 -13(9) 3_666 . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C14 C13 N1 176.8(13) . . . . ?
C15 C14 C13 C18 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C13 0.0 . . . . ?
C17 C18 C13 N1 -176.6(15) . . . . ?
C17 C18 C13 C14 0.0 . . . . ?
C13 N1 C11 O2 11(2) . . . . ?
C13 N1 C11 C10 -172.6(16) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;

####################################################################### 
# 
# 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_PTCDI_Ph_400K
_database_code_depnum_ccdc_archive 'CCDC 2253200'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_PTCDI_Ph_400K       
;
PROBLEM: The value of Rint is greater than 0.25
            Rint given   0.275
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
_vrf_PLAT020_PTCDI_Ph_400K       
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.275 Report
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
_vrf_PLAT026_PTCDI_Ph_400K       
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..         8% Check  
RESPONSE: This low value comes from the overall poor diffraction quality of 
the crystal.
;
_vrf_PLAT027_PTCDI_Ph_400K       
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      50.00 Degree
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
_vrf_PLAT084_PTCDI_Ph_400K       
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.38 Report    
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
_vrf_PLAT340_PTCDI_Ph_400K       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............      0.0305 Ang.    
RESPONSE: These data come from high-temperature studies and the 
poor quality of the data is related to the progressive build-up of thermal 
motions. Furthermore, the investigated single crystal was small, brittle 
and poorly diffractive. Attempts to collect higher quality data at high 
temperatures were unsuccessful.
;
# end Validation Reply Form

loop_
_audit_creation_date
2023-03-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            PTCDI-Ph
_chemical_name_systematic        N,N-Diphenyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H18 N2 O4'
_chemical_formula_sum            'C36 H18 N2 O4'
_chemical_formula_weight         542.52
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.680(10)
_cell_length_b                   4.1044(13)
_cell_length_c                   18.246(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.28(5)
_cell_angle_gamma                90
_cell_volume                     1236.1(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    109
_cell_measurement_temperature    673.15
_cell_measurement_theta_max      50.2370
_cell_measurement_theta_min      2.6600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.778
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2750
_diffrn_reflns_av_unetI/netI     0.9318
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3912
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        50.000
_diffrn_reflns_theta_max         71.151
_diffrn_reflns_theta_min         2.677
_diffrn_ambient_temperature      673.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
 Data were collected at temperature of 400 K
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                188
_reflns_number_total             2216
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.830
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2216
_refine_ls_number_restraints     255
_refine_ls_R_factor_all          0.5818
_refine_ls_R_factor_gt           0.1293
_refine_ls_restrained_S_all      0.797
_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)+(0.0445P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2195
_refine_ls_wR_factor_ref         0.3763
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C9-C10 \\sim C9-C8 \\sim C8-C7 \\sim C7-C6 \\sim C6-C12 \\sim C12-C10 \\sim
C2-C12 \\sim C3-C2 \\sim C4-C3 ~
 C5-C4 \\sim C6-C5 \\sim C2-C1 \\sim C11-C10
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C4(H4), C3(H3), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
4.b Fitted hexagon refined as free rotating group:
 C12(C2,C1,N1,C11,C10), C13(C14,C15,C16,C17,C18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 0.8303(7) 0.061(3) 0.6578(6) 0.126(6) Uani 1 1 d . . . . .
O1 O 0.6856(6) 0.603(3) 0.8123(6) 0.105(5) Uani 1 1 d . . . . .
C7 C 0.5753(12) 0.335(5) 0.4886(12) 0.100(7) Uani 1 1 d D . . . .
C8 C 0.6464(9) 0.181(4) 0.4748(9) 0.094(7) Uani 1 1 d D . . . .
H8 H 0.652955 0.103742 0.428186 0.113 Uiso 1 1 calc R U . . .
C9 C 0.7073(10) 0.152(4) 0.5362(7) 0.091(6) Uani 1 1 d D . . . .
H9 H 0.755742 0.056795 0.527819 0.109 Uiso 1 1 calc R U . . .
C5 C 0.4972(12) 0.615(4) 0.5706(10) 0.073(6) Uani 1 1 d D . . . .
C4 C 0.4903(9) 0.746(4) 0.6406(8) 0.072(6) Uani 1 1 d D . . . .
H4 H 0.442988 0.850340 0.648948 0.087 Uiso 1 1 calc R U . . .
C12 C 0.6324(8) 0.417(3) 0.6199(8) 0.092(7) Uani 1 1 d DG . . . .
C2 C 0.6268(7) 0.550(3) 0.6889(11) 0.108(8) Uani 1 1 d DG . . . .
C1 C 0.6910(11) 0.519(3) 0.7462(6) 0.094(6) Uani 1 1 d DG . . . .
N1 N 0.7608(7) 0.354(3) 0.7344(8) 0.100(5) Uani 1 1 d G . . . .
C11 C 0.7665(7) 0.221(3) 0.6653(10) 0.121(9) Uani 1 1 d DG . . . .
C10 C 0.7023(12) 0.252(3) 0.6080(6) 0.114(8) Uani 1 1 d DG . . . .
C3 C 0.5558(8) 0.717(4) 0.6975(9) 0.099(7) Uani 1 1 d D . . . .
H3 H 0.551796 0.813381 0.743034 0.118 Uiso 1 1 calc R U . . .
C6 C 0.5710(9) 0.469(4) 0.5594(9) 0.070(5) Uani 1 1 d D . . . .
C13 C 0.8297(7) 0.321(3) 0.7946(8) 0.109(7) Uani 1 1 d G . . . .
C14 C 0.8226(6) 0.174(3) 0.8620(10) 0.120(8) Uani 1 1 d G . . . .
H14 H 0.773623 0.080789 0.869678 0.144 Uiso 1 1 calc R U . . .
C15 C 0.8886(11) 0.166(3) 0.9179(6) 0.146(10) Uani 1 1 d G . . . .
H15 H 0.883842 0.067785 0.963028 0.175 Uiso 1 1 calc R U . . .
C16 C 0.9618(7) 0.305(3) 0.9065(7) 0.131(9) Uani 1 1 d G . . . .
H16 H 1.005937 0.299909 0.943874 0.157 Uiso 1 1 calc R U . . .
C17 C 0.9689(6) 0.452(3) 0.8390(10) 0.125(9) Uani 1 1 d G . . . .
H17 H 1.017812 0.545038 0.831369 0.150 Uiso 1 1 calc R U . . .
C18 C 0.9028(10) 0.460(3) 0.7831(6) 0.117(8) Uani 1 1 d G . . . .
H18 H 0.907593 0.558044 0.738018 0.140 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
O2 C11 1.274(13) . ?
O1 C1 1.268(13) . ?
C7 C8 1.398(12) . ?
C7 C5 1.516(16) 3_666 ?
C7 C6 1.413(12) . ?
C8 H8 0.9300 . ?
C8 C9 1.404(11) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(11) . ?
C5 C4 1.405(11) . ?
C5 C6 1.411(12) . ?
C4 H4 0.9300 . ?
C4 C3 1.399(11) . ?
C12 C2 1.3900 . ?
C12 C10 1.3900 . ?
C12 C6 1.411(11) . ?
C2 C1 1.3900 . ?
C2 C3 1.397(11) . ?
C1 N1 1.3900 . ?
N1 C11 1.3900 . ?
N1 C13 1.477(10) . ?
C11 C10 1.3900 . ?
C3 H3 0.9300 . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C14 H14 0.9300 . ?
C14 C15 1.3900 . ?
C15 H15 0.9300 . ?
C15 C16 1.3900 . ?
C16 H16 0.9300 . ?
C16 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C18 1.3900 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C7 C5 123(2) . 3_666 ?
C8 C7 C6 120(2) . . ?
C6 C7 C5 117.3(14) . 3_666 ?
C7 C8 H8 122.3 . . ?
C7 C8 C9 115.5(19) . . ?
C9 C8 H8 122.3 . . ?
C8 C9 H9 116.8 . . ?
C10 C9 C8 126.4(17) . . ?
C10 C9 H9 116.8 . . ?
C4 C5 C7 115.9(19) . 3_666 ?
C4 C5 C6 119(2) . . ?
C6 C5 C7 125.2(14) . 3_666 ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.1(18) . . ?
C3 C4 H4 120.5 . . ?
C2 C12 C10 120.0 . . ?
C2 C12 C6 120.9(19) . . ?
C10 C12 C6 118.9(19) . . ?
C12 C2 C1 120.0 . . ?
C12 C2 C3 117.7(18) . . ?
C1 C2 C3 122.3(18) . . ?
O1 C1 C2 122.5(17) . . ?
O1 C1 N1 117.0(17) . . ?
N1 C1 C2 120.0 . . ?
C1 N1 C11 120.0 . . ?
C1 N1 C13 120.6(16) . . ?
C11 N1 C13 119.4(16) . . ?
O2 C11 N1 117.9(17) . . ?
O2 C11 C10 122.1(17) . . ?
C10 C11 N1 120.0 . . ?
C9 C10 C12 117.1(18) . . ?
C9 C10 C11 122.6(18) . . ?
C11 C10 C12 120.0 . . ?
C4 C3 H3 118.6 . . ?
C2 C3 C4 122.8(17) . . ?
C2 C3 H3 118.6 . . ?
C5 C6 C7 117.3(14) . . ?
C12 C6 C7 122(2) . . ?
C12 C6 C5 120(2) . . ?
C14 C13 N1 122.8(15) . . ?
C14 C13 C18 120.0 . . ?
C18 C13 N1 117.1(15) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 H18 120.0 . . ?

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
O2 C11 C10 C9 -9.3(15) . . . . ?
O2 C11 C10 C12 177.2(15) . . . . ?
O1 C1 N1 C11 172.2(13) . . . . ?
O1 C1 N1 C13 -8.1(14) . . . . ?
C7 C8 C9 C10 2(3) . . . . ?
C7 C5 C4 C3 -178.3(16) 3_666 . . . ?
C7 C5 C6 C7 -5(3) 3_666 . . . ?
C7 C5 C6 C12 -175.9(14) 3_666 . . . ?
C8 C7 C6 C5 -178.7(18) . . . . ?
C8 C7 C6 C12 -8(3) . . . . ?
C8 C9 C10 C12 -5(3) . . . . ?
C8 C9 C10 C11 -178.4(15) . . . . ?
C5 C7 C8 C9 -179.3(17) 3_666 . . . ?
C5 C7 C6 C5 5(3) 3_666 . . . ?
C5 C7 C6 C12 175.3(12) 3_666 . . . ?
C5 C4 C3 C2 -3(3) . . . . ?
C4 C5 C6 C7 179.1(16) . . . . ?
C4 C5 C6 C12 8(3) . . . . ?
C12 C2 C1 O1 -171.7(14) . . . . ?
C12 C2 C1 N1 0.0 . . . . ?
C12 C2 C3 C4 2(2) . . . . ?
C2 C12 C10 C9 -173.9(14) . . . . ?
C2 C12 C10 C11 0.0 . . . . ?
C2 C12 C6 C7 -179.9(14) . . . . ?
C2 C12 C6 C5 -10(2) . . . . ?
C2 C1 N1 C11 0.0 . . . . ?
C2 C1 N1 C13 179.7(12) . . . . ?
C1 C2 C3 C4 -179.1(13) . . . . ?
C1 N1 C11 O2 -177.3(14) . . . . ?
C1 N1 C11 C10 0.0 . . . . ?
C1 N1 C13 C14 58.0(12) . . . . ?
C1 N1 C13 C18 -118.5(9) . . . . ?
N1 C11 C10 C9 173.6(15) . . . . ?
N1 C11 C10 C12 0.0 . . . . ?
N1 C13 C14 C15 -176.4(13) . . . . ?
N1 C13 C18 C17 176.6(12) . . . . ?
C11 N1 C13 C14 -122.3(9) . . . . ?
C11 N1 C13 C18 61.2(11) . . . . ?
C10 C12 C2 C1 0.0 . . . . ?
C10 C12 C2 C3 179.0(14) . . . . ?
C10 C12 C6 C7 5(2) . . . . ?
C10 C12 C6 C5 175.7(13) . . . . ?
C3 C2 C1 O1 9.3(15) . . . . ?
C3 C2 C1 N1 -179.0(15) . . . . ?
C6 C7 C8 C9 4(3) . . . . ?
C6 C5 C4 C3 -2(3) . . . . ?
C6 C12 C2 C1 -174.6(12) . . . . ?
C6 C12 C2 C3 4.4(16) . . . . ?
C6 C12 C10 C9 0.8(14) . . . . ?
C6 C12 C10 C11 174.7(12) . . . . ?
C13 N1 C11 O2 3.0(15) . . . . ?
C13 N1 C11 C10 -179.7(11) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C13 0.0 . . . . ?
C18 C13 C14 C15 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
