# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_PDI_C5_0_1MPa
_database_code_depnum_ccdc_archive 'CCDC 2493894'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PDI_C5_0_1MPa       
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      15.00 Degree
RESPONSE: Due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell limiting the access of 
the X-ray radiation to the measured sample. A full set of data was collected.
;
_vrf_PLAT029_PDI_C5_0_1MPa       
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.343 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C5_0_1MPa       
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.91 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C5_0_1MPa       
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.04278 Ang. 
RESPONSE: The data come from high-pressure experiment, and part of the 
reflection can not be collected, affecting the bond precision.
;
_vrf_PLAT911_PDI_C5_0_1MPa       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        447 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-02-28

_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C5
_chemical_name_systematic        N,N-Dipentyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C34 H30 N2 O4'
_chemical_formula_sum            'C34 H30 N2 O4'
_chemical_formula_weight         530.60
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.727(3)
_cell_length_b                   8.493(3)
_cell_length_c                   16.308(9)
_cell_angle_alpha                86.78(8)
_cell_angle_beta                 83.27(10)
_cell_angle_gamma                84.12(4)
_cell_volume                     646.1(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    657
_cell_measurement_temperature    297.10(10)
_cell_measurement_theta_max      24.3880
_cell_measurement_theta_min      4.3400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.451
_exptl_absorpt_correction_T_min  0.292
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.79a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 11 1 0.1114
0 0 -23 0.0213
0 0 23 0.0213
-7 -2 -4 0.0596
-6 -5 -4 0.0663
1 -11 -1 0.1283
6 4 4 0.0669
7 2 4 0.0551

_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.043
_exptl_oxdiff_absorpt_process_details 
;
Gaussian integration over a grid
of 16 x 16 x 16 points =  4096 total grid points
  Based upon method of Burnham (1966)

 Data corrected for diamond-anvil cell absorption
 Note that exptl_absorpt_correction_tmin and _tmax
 the total correction factors applied to the intensities
 The individual factors are: 
         range of dac transmission factors (min-max)      0.404     0.453
         range of gasket transmission (min-max)           0.692     1.000
         range of P media transmission (min-max)          1.000     1.000

 thickness of diamond anvil 1: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 1:  0.000 mm, mu =  0.0000 mm-1

 thickness of diamond anvil 2: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 2:  0.000 mm, mu =  0.0000 mm-1

    Gasket shadowing corrections were made based upon
    Gasket thickness = 300.0 microns, radius = 200.0 microns
    Gasket absorption coeff =        21.00 mm-1
    REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF 
 FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00

    Non-absorbing pressure medium
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1391
_diffrn_reflns_av_unetI/netI     0.1278
_diffrn_reflns_Laue_measured_fraction_full 0.343
_diffrn_reflns_Laue_measured_fraction_max 0.192
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4469
_diffrn_reflns_point_group_measured_fraction_full 0.343
_diffrn_reflns_point_group_measured_fraction_max 0.192
_diffrn_reflns_theta_full        15.000
_diffrn_reflns_theta_max         26.878
_diffrn_reflns_theta_min         4.402
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.343
_diffrn_measured_fraction_theta_max 0.192
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.25  19.00   0.75    7.50    --    0.10  19.00-180.00   83
  2  ω     14.00  70.25   0.75    7.50    --    0.10-114.00  45.00   75
  3  ω    -57.00 -21.00   0.75   17.50    --  -31.98  77.00 -30.00   48
  4  ω    -40.00   6.50   0.75   17.50    --  -31.98  26.00  -7.00   62
  5  ω    -31.00   0.50   0.75   17.50    --  -31.98   0.00   0.00   42
  6  ω    -14.00  20.50   0.75   17.50    --  -31.98 -53.00  17.00   46
  7  ω      4.00  28.00   0.75   17.50    --  -31.98 -97.00  35.00   32
  8  ω    -44.00  19.00   0.75   17.50    --  -31.98  39.00 167.00   84
  9  ω     14.00  38.00   0.75   17.50    --  -31.98-114.00-135.00   32
 10  ω    -88.00 -40.75   0.75   17.50    --  -31.98 135.00 -57.00   63
 11  ω    -19.00  26.00   0.75   17.50    --  -31.98 -39.00-167.00   60
 12  ω    -67.00 -20.50   0.75   17.50    --  -31.98  97.00 143.00   62
 13  ω    -19.00  44.00   0.75   17.50    --  -31.98 -39.00  12.00   84
 14  ω    -30.00   0.00   0.75   17.50    --   32.17   0.00-150.00   40
 15  ω     21.00  56.25   0.75   17.50    --   32.17 -77.00  30.00   47
 16  ω    -24.25  23.00   0.75   17.50    --   32.17  26.00  -7.00   63
 17  ω     20.00  56.00   0.75   17.50    --   32.17 -77.00-150.00   48
 18  ω    -38.00 -14.00   0.75   17.50    --   32.17 114.00 -45.00   32
 19  ω    -30.00   0.00   0.75   17.50    --   32.17   0.00  30.00   40
 20  ω    -53.00 -26.00   0.75    7.50    --    0.10  37.00  30.00   36
 21  ω    -47.00   7.00   0.75    7.50    --    0.10  67.00 157.00   72
 22  ω     26.75  83.00   0.75    7.50    --    0.10-135.00-123.00   75
 23  ω    -19.00  44.00   0.75   17.50    --  -31.98 -39.00  12.00   84
 24  ω    -22.25  40.00   0.75   17.50    --  -31.98 -26.00   7.00   83
 25  ω    -18.00  17.25   0.75   17.50    --  -31.98 -57.00-150.00   47
 26  ω    -35.25  27.00   0.75   17.50    --  -31.98  13.00 176.00   83
 27  ω     -3.00  21.00   0.75   17.50    --  -31.98 -81.00-151.00   32
 28  ω    -27.00  36.00   0.75   17.50    --  -31.98 -13.00   3.00   84
 29  ω    -40.00  23.00   0.75   17.50    --  -31.98  26.00 172.00   84
 30  ω    -30.00  15.00   0.75   17.50    --  -31.98   0.00-180.00   60
 31  ω    -43.25  19.00   0.75   17.50    --  -31.98  19.00-180.00   83
 32  ω    -20.00  13.00   0.75   17.50    --   32.17  53.00 -17.00   44
 33  ω      6.00  41.25   0.75   17.50    --   32.17 -57.00  30.00   47
 34  ω     31.00  76.00   0.75   17.50    --   32.17-114.00-135.00   60
 35  ω    -24.00   0.00   0.75   17.50    --   32.17   0.00   0.00   32
 36  ω    -21.00   3.00   0.75   17.50    --   32.17  81.00 151.00   32
 37  ω    -10.50  36.00   0.75   17.50    --   32.17 -13.00-176.00   62
 38  ω    -43.25  19.00   0.75    7.50    --    0.10  19.00-180.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          
;
 Data were collected at room conditions (296 K / 0.1 MPa)
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                218
_reflns_number_total             530
_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 1.171.40.79a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.79a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.79a (Rigaku OD, 2020)'
_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         0.185
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         530
_refine_ls_number_restraints     539
_refine_ls_R_factor_all          0.2323
_refine_ls_R_factor_gt           0.1091
_refine_ls_restrained_S_all      0.718
_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)+(0.0843P)²+4.7546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2308
_refine_ls_wR_factor_ref         0.3152
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-N1
 1.38 with sigma of 0.01
 C14-C13 \\sim C15-C14 \\sim C16-C15 \\sim C17-C16
 with sigma of 0.02
 C5-C1 \\sim C3-C2 \\sim C4-C3 \\sim C5-C4 \\sim C6-C5 \\sim C6-C7 \\sim C7-C8
\\sim C9-C8 \\sim C4-C9 \\sim C10-
 C9 \\sim C11-C10 \\sim C12-C11 \\sim C3-C12
 with sigma of 0.02
 O2-C2 \\sim O1-C1
 with sigma of 0.02
 N1-C2 \\sim N1-C1
 with sigma of 0.02
3. Rigid bond restraints
 O1, O2, N1, C8, C9, C10, C11, C12, C3, C4, C5, C6, C7, C1, C2, C13, C14, C15,
 C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N1 \\sim O1 \\sim C1 \\sim C5 \\sim C2 \\sim C13 \\sim C4 \\sim C6 \\sim O2
\\sim C3 \\sim C14 \\sim C9 \\sim C7 \\sim C12 \\sim C15 \\sim C8 \\sim C10
\\sim C11 \\sim C16 \\sim C17: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2)
\\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq,
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 O1, N1, C8, C9, C10, C11, C12, C3, C4, C5, C6, C7, C1, C2, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Secondary CH2 refined with riding coordinates:
 C13(H6,H5), C14(H7,H8), C15(H9,H10), C16(H11,H12)
6.b Aromatic/amide H refined with riding coordinates:
 C11(H3), C12(H4), C6(H1), C7(H2)
6.c Idealised Me refined as rotating group:
 C17(H13,H14,H15)
;
_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 -1.038(3) 0.4485(13) 0.130(3) 0.057(8) Uani 1 1 d D U . . .
O2 O -0.799(4) 0.0732(14) 0.322(2) 0.064(7) Uani 1 1 d D U . . .
N1 N -0.915(4) 0.2596(14) 0.227(2) 0.047(6) Uani 1 1 d D U . . .
C8 C -0.184(4) 0.1318(19) -0.030(3) 0.036(7) Uani 1 1 d D U . . .
C9 C -0.224(5) 0.067(2) 0.052(2) 0.044(8) Uani 1 1 d D U . . .
C10 C -0.046(5) -0.0658(17) 0.081(3) 0.043(9) Uani 1 1 d D U . . .
C11 C -0.109(5) -0.134(2) 0.162(3) 0.053(10) Uani 1 1 d D U . . .
H3 H 0.002919 -0.224577 0.177438 0.064 Uiso 1 1 calc R U . . .
C12 C -0.334(4) -0.0715(16) 0.221(3) 0.058(9) Uani 1 1 d D U . . .
H4 H -0.364331 -0.115819 0.274415 0.070 Uiso 1 1 calc R U . . .
C3 C -0.509(4) 0.0628(18) 0.193(2) 0.046(7) Uani 1 1 d D U . . .
C4 C -0.448(4) 0.1304(17) 0.111(2) 0.036(7) Uani 1 1 d D U . . .
C5 C -0.646(4) 0.261(2) 0.092(2) 0.043(7) Uani 1 1 d D U . . .
C6 C -0.602(4) 0.319(2) 0.008(2) 0.042(7) Uani 1 1 d D U . . .
H1 H -0.732872 0.399341 -0.008741 0.050 Uiso 1 1 calc R U . . .
C7 C -0.375(3) 0.2641(15) -0.052(3) 0.032(6) Uani 1 1 d D U . . .
H2 H -0.352994 0.313570 -0.104773 0.039 Uiso 1 1 calc R U . . .
C1 C -0.876(4) 0.331(2) 0.148(2) 0.044(7) Uani 1 1 d D U . . .
C2 C -0.732(5) 0.131(2) 0.252(2) 0.053(8) Uani 1 1 d D U . . .
C13 C -1.140(4) 0.340(2) 0.290(4) 0.054(8) Uani 1 1 d D U . . .
H6 H -1.191945 0.267305 0.336131 0.064 Uiso 1 1 calc R U . . .
H5 H -1.310921 0.379897 0.264952 0.064 Uiso 1 1 calc R U . . .
C14 C -0.990(5) 0.476(2) 0.318(4) 0.075(11) Uani 1 1 d D U . . .
H7 H -0.915651 0.538986 0.270582 0.090 Uiso 1 1 calc R U . . .
H8 H -0.832237 0.434109 0.348458 0.090 Uiso 1 1 calc R U . . .
C15 C -1.214(5) 0.577(2) 0.374(3) 0.072(11) Uani 1 1 d D U . . .
H9 H -1.359495 0.626156 0.340696 0.087 Uiso 1 1 calc R U . . .
H10 H -1.305367 0.508665 0.416105 0.087 Uiso 1 1 calc R U . . .
C16 C -1.085(5) 0.705(2) 0.415(4) 0.078(8) Uani 1 1 d D U . . .
H11 H -0.979059 0.767873 0.372168 0.094 Uiso 1 1 calc R U . . .
H12 H -0.950173 0.655519 0.450899 0.094 Uiso 1 1 calc R U . . .
C17 C -1.308(5) 0.816(3) 0.464(4) 0.090(11) Uani 1 1 d D U . . .
H13 H -1.442843 0.865492 0.428989 0.134 Uiso 1 1 calc R U . . .
H14 H -1.214640 0.895810 0.487259 0.134 Uiso 1 1 calc R U . . .
H15 H -1.406782 0.755913 0.508433 0.134 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 1.24(2) . ?
O2 C2 1.25(3) . ?
N1 C1 1.39(2) . ?
N1 C2 1.392(11) . ?
N1 C13 1.53(6) . ?
C8 C9 1.425(19) . ?
C8 C10 1.37(5) 2 ?
C8 C7 1.425(15) . ?
C9 C10 1.426(16) . ?
C9 C4 1.428(17) . ?
C10 C11 1.429(19) . ?
C11 H3 0.9300 . ?
C11 C12 1.428(19) . ?
C12 H4 0.9300 . ?
C12 C3 1.423(16) . ?
C3 C4 1.432(18) . ?
C3 C2 1.434(17) . ?
C4 C5 1.423(16) . ?
C5 C6 1.428(19) . ?
C5 C1 1.433(18) . ?
C6 H1 0.9300 . ?
C6 C7 1.428(18) . ?
C7 H2 0.9300 . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.53(2) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C15 1.53(2) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.52(2) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C17 1.53(2) . ?
C17 H13 0.9600 . ?
C17 H14 0.9600 . ?
C17 H15 0.9600 . ?

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 C13 118(2) . . ?
C2 N1 C1 122(3) . . ?
C2 N1 C13 120(3) . . ?
C9 C8 C7 117(2) . . ?
C10 C8 C9 117(2) 2 . ?
C10 C8 C7 126(3) 2 . ?
C8 C9 C10 122(3) . . ?
C8 C9 C4 121.9(18) . . ?
C10 C9 C4 116(3) . . ?
C8 C10 C9 121(3) 2 . ?
C8 C10 C11 119(2) 2 . ?
C9 C10 C11 120(3) . . ?
C10 C11 H3 117.9 . . ?
C12 C11 C10 124(2) . . ?
C12 C11 H3 117.9 . . ?
C11 C12 H4 122.1 . . ?
C3 C12 C11 116(3) . . ?
C3 C12 H4 122.1 . . ?
C12 C3 C4 120(2) . . ?
C12 C3 C2 117(2) . . ?
C4 C3 C2 122.4(17) . . ?
C9 C4 C3 123.8(17) . . ?
C5 C4 C9 123(2) . . ?
C5 C4 C3 113(2) . . ?
C4 C5 C6 113(2) . . ?
C4 C5 C1 126(2) . . ?
C6 C5 C1 121(2) . . ?
C5 C6 H1 116.7 . . ?
C7 C6 C5 126.5(19) . . ?
C7 C6 H1 116.7 . . ?
C8 C7 C6 118(2) . . ?
C8 C7 H2 120.9 . . ?
C6 C7 H2 120.9 . . ?
O1 C1 N1 119(3) . . ?
O1 C1 C5 124(3) . . ?
N1 C1 C5 116(2) . . ?
O2 C2 N1 115(3) . . ?
O2 C2 C3 124.6(18) . . ?
N1 C2 C3 120(2) . . ?
N1 C13 H6 111.1 . . ?
N1 C13 H5 111.1 . . ?
N1 C13 C14 103(2) . . ?
H6 C13 H5 109.1 . . ?
C14 C13 H6 111.1 . . ?
C14 C13 H5 111.1 . . ?
C13 C14 H7 110.3 . . ?
C13 C14 H8 110.3 . . ?
C13 C14 C15 107(2) . . ?
H7 C14 H8 108.5 . . ?
C15 C14 H7 110.3 . . ?
C15 C14 H8 110.3 . . ?
C14 C15 H9 109.0 . . ?
C14 C15 H10 109.0 . . ?
H9 C15 H10 107.8 . . ?
C16 C15 C14 113(2) . . ?
C16 C15 H9 109.0 . . ?
C16 C15 H10 109.0 . . ?
C15 C16 H11 108.9 . . ?
C15 C16 H12 108.9 . . ?
C15 C16 C17 113(2) . . ?
H11 C16 H12 107.7 . . ?
C17 C16 H11 108.9 . . ?
C17 C16 H12 108.9 . . ?
C16 C17 H13 109.5 . . ?
C16 C17 H14 109.5 . . ?
C16 C17 H15 109.5 . . ?
H13 C17 H14 109.5 . . ?
H13 C17 H15 109.5 . . ?
H14 C17 H15 109.5 . . ?

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
N1 C13 C14 C15 173(3) . . . . ?
C8 C9 C10 C8 4(4) . . . 2 ?
C8 C9 C10 C11 -175(2) . . . . ?
C8 C9 C4 C3 175(2) . . . . ?
C8 C9 C4 C5 0(3) . . . . ?
C8 C10 C11 C12 177(2) 2 . . . ?
C9 C8 C7 C6 -3(3) . . . . ?
C9 C10 C11 C12 -4(3) . . . . ?
C9 C4 C5 C6 2(3) . . . . ?
C9 C4 C5 C1 -180(2) . . . . ?
C10 C8 C9 C10 -4(4) 2 . . . ?
C10 C8 C9 C4 177.3(19) 2 . . . ?
C10 C8 C7 C6 -179(2) 2 . . . ?
C10 C9 C4 C3 -3(3) . . . . ?
C10 C9 C4 C5 -179(2) . . . . ?
C10 C11 C12 C3 3(3) . . . . ?
C11 C12 C3 C4 -2(3) . . . . ?
C11 C12 C3 C2 -178(2) . . . . ?
C12 C3 C4 C9 3(3) . . . . ?
C12 C3 C4 C5 178.5(18) . . . . ?
C12 C3 C2 O2 -7(4) . . . . ?
C12 C3 C2 N1 -178.1(19) . . . . ?
C3 C4 C5 C6 -174(2) . . . . ?
C3 C4 C5 C1 4(3) . . . . ?
C4 C9 C10 C8 -177.0(19) . . . 2 ?
C4 C9 C10 C11 4(3) . . . . ?
C4 C3 C2 O2 177(2) . . . . ?
C4 C3 C2 N1 6(4) . . . . ?
C4 C5 C6 C7 -4(4) . . . . ?
C4 C5 C1 O1 177(2) . . . . ?
C4 C5 C1 N1 -3(3) . . . . ?
C5 C6 C7 C8 5(3) . . . . ?
C6 C5 C1 O1 -4(4) . . . . ?
C6 C5 C1 N1 176(2) . . . . ?
C7 C8 C9 C10 179.5(17) . . . . ?
C7 C8 C9 C4 1(4) . . . . ?
C1 N1 C2 O2 -176(2) . . . . ?
C1 N1 C2 C3 -4(3) . . . . ?
C1 N1 C13 C14 -78(3) . . . . ?
C1 C5 C6 C7 177.3(16) . . . . ?
C2 N1 C1 O1 -178(2) . . . . ?
C2 N1 C1 C5 3(3) . . . . ?
C2 N1 C13 C14 94(3) . . . . ?
C2 C3 C4 C9 179(2) . . . . ?
C2 C3 C4 C5 -5(3) . . . . ?
C13 N1 C1 O1 -6(3) . . . . ?
C13 N1 C1 C5 174.6(17) . . . . ?
C13 N1 C2 O2 12(3) . . . . ?
C13 N1 C2 C3 -176(2) . . . . ?
C13 C14 C15 C16 173(3) . . . . ?
C14 C15 C16 C17 175(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
####################################################################### 
# 
# 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_PDI_C5_0_66GPa
_database_code_depnum_ccdc_archive 'CCDC 2493895'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PDI_C5_0_66GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      16.00 Degree
RESPONSE: Due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell limiting the access of 
the X-ray radiation to the measured sample. A full set of data was collected.
;
_vrf_PLAT029_PDI_C5_0_66GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.343 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C5_0_66GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.75 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C5_0_66GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.04167 Ang. 
RESPONSE: The data come from high-pressure experiment, and part of the 
reflection can not be collected, affecting the bond precision.
;
_vrf_PLAT911_PDI_C5_0_66GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        605 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-02-25

_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C5
_chemical_name_systematic        N,N-Dipentyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C34 H30 N2 O4'
_chemical_formula_sum            'C34 H30 N2 O4'
_chemical_formula_weight         530.60
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.6276(7)
_cell_length_b                   8.4373(8)
_cell_length_c                   15.934(8)
_cell_angle_alpha                85.82(2)
_cell_angle_beta                 82.97(3)
_cell_angle_gamma                85.077(10)
_cell_volume                     613.9(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    471
_cell_measurement_temperature    297.10(10)
_cell_measurement_theta_max      22.6930
_cell_measurement_theta_min      4.4630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.451
_exptl_absorpt_correction_T_min  0.399
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.79a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 11 1 0.1114
6 4 5 0.0669
1 -11 -1 0.1283
-6 -4 -5 0.0663
-6 -2 -4 0.0596
0 0 22 0.0213
6 2 4 0.0551
0 0 -22 0.0213

_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.042
_exptl_oxdiff_absorpt_process_details 
;
Gaussian integration over a grid
of 16 x 16 x 16 points =  4096 total grid points
  Based upon method of Burnham (1966)

 Data corrected for diamond-anvil cell absorption
 Note that exptl_absorpt_correction_tmin and _tmax
 the total correction factors applied to the intensities
 The individual factors are: 
         range of dac transmission factors (min-max)      0.401     0.453
         range of gasket transmission (min-max)           1.000     1.000
         range of P media transmission (min-max)          1.000     1.000

 thickness of diamond anvil 1: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 1:  0.000 mm, mu =  0.0000 mm-1

 thickness of diamond anvil 2: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 2:  0.000 mm, mu =  0.0000 mm-1

    Gasket shadowing corrections were made based upon
    Gasket thickness = 280.0 microns, radius = 300.0 microns
    Gasket absorption coeff =        21.00 mm-1
    REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF 
 FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00

    Non-absorbing pressure medium
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 0.316
_diffrn_reflns_Laue_measured_fraction_max 0.197
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2905
_diffrn_reflns_point_group_measured_fraction_full 0.316
_diffrn_reflns_point_group_measured_fraction_max 0.197
_diffrn_reflns_theta_full        16.000
_diffrn_reflns_theta_max         26.472
_diffrn_reflns_theta_min         4.451
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.316
_diffrn_measured_fraction_theta_max 0.197
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      4.00  31.00   0.75   20.00    --  -29.94 -97.00  35.00   36
  2  ω    -51.00 -21.00   0.75   20.00    --  -29.94  77.00 -30.00   40
  3  ω    -27.00   5.25   0.75   20.00    --  -29.94   0.00-180.00   43
  4  ω    -55.00 -20.50   0.75   20.00    --  -29.94  77.00 150.00   46
  5  ω    -18.25  14.00   0.75   20.00    --  -29.94 -19.00   0.00   43
  6  ω      8.00  32.00   0.75   20.00    --  -29.94 -99.00-150.00   32
  7  ω     25.00  56.50   0.75   20.00    --   30.41 -77.00  30.00   42
  8  ω    -49.00 -25.00   0.75   20.00    --   30.41  37.00-150.00   32
  9  ω    -17.00  13.00   0.75   20.00    --   30.41  53.00 -17.00   40
 10  ω    -75.00 -28.50   0.75   20.00    --  -29.94 125.00 120.00   62
 11  ω     -7.00  30.50   0.75   20.00    --  -29.94 -37.00-180.00   50
 12  ω    -75.00 -28.50   0.75   20.00    --  -29.94 125.00 120.00   62
 13  ω    -63.00 -21.00   0.75   20.00    --  -29.94  57.00-180.00   56
 14  ω     18.00  62.25   0.75   20.00    --   30.41 -57.00-180.00   59
 15  ω     12.00  53.25   0.75   20.00    --   30.41 -37.00-180.00   55
 16  ω    -44.00  -6.50   0.75   20.00    --  -29.94  39.00 167.00   50
 17  ω    -88.00 -50.50   0.75   20.00    --  -29.94 135.00 -57.00   50
 18  ω    -50.00 -14.00   0.75   20.00    --  -29.94  37.00-180.00   48
 19  ω    -16.00  20.00   0.75   20.00    --  -29.94 -57.00-150.00   48
 20  ω     53.75  89.00   0.75   20.00    --   30.41-135.00  57.00   47
 21  ω      6.00  41.25   0.75   20.00    --   30.41 -57.00  30.00   47
 22  ω    -20.00  15.25   0.75   20.00    --  -29.94 -26.00   7.00   47
 23  ω    -26.00  10.00   0.75   20.00    --  -29.94 -13.00   3.00   48
 24  ω    -56.00 -20.75   0.75   20.00    --  -29.94  81.00 -29.00   47
 25  ω    -74.00 -38.75   0.75   20.00    --  -29.94 114.00 -45.00   47
 26  ω    -13.00  12.50   0.75   20.00    --  -29.94 -53.00-162.00   34
 27  ω    -17.00  19.00   0.75   20.00    --  -29.94 -39.00  12.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 0.66(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                240
_reflns_number_total             500
_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 1.171.40.79a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.79a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.79a (Rigaku OD, 2020)'
_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         0.152
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         500
_refine_ls_number_restraints     361
_refine_ls_R_factor_all          0.2017
_refine_ls_R_factor_gt           0.0999
_refine_ls_restrained_S_all      0.795
_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)+6.6616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1503
_refine_ls_wR_factor_ref         0.2048
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O2-C2 \\sim O1-C1
 with sigma of 0.02
 C5-C4 \\sim C4-C3 \\sim C4-C9 \\sim C3-C12 \\sim C12-C11 \\sim C11-C10 \\sim
C10-C9 \\sim C9-C8 \\sim C7-C8 ~
 C6-C7 \\sim C6-C5
 with sigma of 0.02
 N1-C1 \\sim N1-C2
 with sigma of 0.02
 C5-C1 \\sim C3-C2
 with sigma of 0.02
 C14-C13 \\sim C15-C14 \\sim C16-C15 \\sim C17-C16
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(O1) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 O1, O2, N1, C8, C9, C10, C11, C12, C3, C4, C5, C6, C7, C1, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C13(H6,H5), C14(H7,H8), C15(H9,H10), C16(H12,H11)
4.b Aromatic/amide H refined with riding coordinates:
 C11(H3), C12(H4), C6(H1), C7(H2)
4.c Idealised Me refined as rotating group:
 C17(H13,H14,H15)
;
_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 -1.042(4) 0.4493(14) 0.126(4) 0.048(8) Uani 1 1 d D U . . .
O2 O -0.820(5) 0.070(2) 0.335(3) 0.063(9) Uani 1 1 d D U . . .
N1 N -0.935(4) 0.2568(17) 0.233(3) 0.033(7) Uani 1 1 d D U . . .
C8 C -0.190(5) 0.1333(18) -0.025(3) 0.028(8) Uani 1 1 d D U . . .
C9 C -0.238(4) 0.0634(18) 0.059(2) 0.023(8) Uani 1 1 d D U . . .
C10 C -0.059(5) -0.0718(19) 0.083(3) 0.030(10) Uani 1 1 d D U . . .
C11 C -0.112(4) -0.138(2) 0.167(3) 0.033(11) Uani 1 1 d D U . . .
H3 H 0.010241 -0.224105 0.184978 0.040 Uiso 1 1 calc R U . . .
C12 C -0.344(4) -0.0776(17) 0.225(3) 0.037(10) Uani 1 1 d D U . . .
H4 H -0.380157 -0.126074 0.278687 0.044 Uiso 1 1 calc R U . . .
C3 C -0.522(4) 0.0569(19) 0.199(2) 0.025(8) Uani 1 1 d D U . . .
C4 C -0.472(4) 0.1247(19) 0.116(2) 0.030(8) Uani 1 1 d D U . . .
C5 C -0.657(4) 0.2573(19) 0.090(2) 0.024(6) Uani 1 1 d D U . . .
C6 C -0.597(3) 0.3226(19) 0.007(2) 0.019(6) Uani 1 1 d D U . . .
H1 H -0.717307 0.410340 -0.010132 0.023 Uiso 1 1 calc R U . . .
C7 C -0.371(3) 0.2661(16) -0.054(3) 0.024(7) Uani 1 1 d D U . . .
H2 H -0.341281 0.312226 -0.108536 0.029 Uiso 1 1 calc R U . . .
C1 C -0.879(4) 0.328(2) 0.148(3) 0.032(7) Uani 1 1 d D U . . .
C2 C -0.753(6) 0.117(3) 0.258(3) 0.033(8) Uani 1 1 d D U . . .
C13 C -1.157(5) 0.334(2) 0.295(4) 0.047(14) Uani 1 1 d D U . . .
H6 H -1.225587 0.256238 0.339215 0.057 Uiso 1 1 calc R U . . .
H5 H -1.322731 0.379735 0.267194 0.057 Uiso 1 1 calc R U . . .
C14 C -1.016(5) 0.464(2) 0.333(4) 0.058(16) Uani 1 1 d D U . . .
H7 H -0.918184 0.529760 0.287717 0.070 Uiso 1 1 calc R U . . .
H8 H -0.869801 0.415140 0.367520 0.070 Uiso 1 1 calc R U . . .
C15 C -1.235(4) 0.571(2) 0.388(3) 0.060(16) Uani 1 1 d D U . . .
H9 H -1.381939 0.618692 0.353294 0.072 Uiso 1 1 calc R U . . .
H10 H -1.332014 0.504774 0.433152 0.072 Uiso 1 1 calc R U . . .
C16 C -1.099(5) 0.702(2) 0.426(4) 0.063(15) Uani 1 1 d D U . . .
H12 H -0.962185 0.653664 0.463651 0.076 Uiso 1 1 calc R U . . .
H11 H -0.988741 0.762738 0.380786 0.076 Uiso 1 1 calc R U . . .
C17 C -1.315(5) 0.817(2) 0.475(4) 0.057(11) Uani 1 1 d D U . . .
H13 H -1.406232 0.891571 0.436179 0.086 Uiso 1 1 calc R U . . .
H14 H -1.214246 0.873276 0.511348 0.086 Uiso 1 1 calc R U . . .
H15 H -1.461323 0.758274 0.508844 0.086 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 1.27(3) . ?
O2 C2 1.27(3) . ?
N1 C1 1.44(3) . ?
N1 C2 1.45(3) . ?
N1 C13 1.48(6) . ?
C8 C9 1.412(19) . ?
C8 C10 1.48(5) 2 ?
C8 C7 1.424(16) . ?
C9 C10 1.410(16) . ?
C9 C4 1.412(18) . ?
C10 C11 1.41(2) . ?
C11 H3 0.9300 . ?
C11 C12 1.41(2) . ?
C12 H4 0.9300 . ?
C12 C3 1.407(16) . ?
C3 C4 1.411(19) . ?
C3 C2 1.42(4) . ?
C4 C5 1.415(17) . ?
C5 C6 1.41(2) . ?
C5 C1 1.42(4) . ?
C6 H1 0.9300 . ?
C6 C7 1.41(2) . ?
C7 H2 0.9300 . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.52(2) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C15 1.52(2) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.52(2) . ?
C16 H12 0.9700 . ?
C16 H11 0.9700 . ?
C16 C17 1.52(2) . ?
C17 H13 0.9600 . ?
C17 H14 0.9600 . ?
C17 H15 0.9600 . ?

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 C2 119(3) . . ?
C1 N1 C13 120(2) . . ?
C2 N1 C13 121(4) . . ?
C9 C8 C10 119.8(18) . 2 ?
C9 C8 C7 122(2) . . ?
C7 C8 C10 118(3) . 2 ?
C10 C9 C8 120(2) . . ?
C10 C9 C4 120(3) . . ?
C4 C9 C8 119.9(19) . . ?
C9 C10 C8 120(3) . 2 ?
C9 C10 C11 118(3) . . ?
C11 C10 C8 121.2(19) . 2 ?
C10 C11 H3 119.1 . . ?
C12 C11 C10 122(2) . . ?
C12 C11 H3 119.1 . . ?
C11 C12 H4 120.3 . . ?
C3 C12 C11 119(3) . . ?
C3 C12 H4 120.3 . . ?
C12 C3 C4 119(2) . . ?
C12 C3 C2 119(3) . . ?
C4 C3 C2 121.8(19) . . ?
C9 C4 C5 121(2) . . ?
C3 C4 C9 120.7(19) . . ?
C3 C4 C5 119(2) . . ?
C4 C5 C1 121(3) . . ?
C6 C5 C4 117(2) . . ?
C6 C5 C1 121(2) . . ?
C5 C6 H1 117.3 . . ?
C5 C6 C7 125(2) . . ?
C7 C6 H1 117.3 . . ?
C8 C7 H2 122.4 . . ?
C6 C7 C8 115(2) . . ?
C6 C7 H2 122.4 . . ?
O1 C1 N1 118(3) . . ?
O1 C1 C5 122(4) . . ?
C5 C1 N1 120(2) . . ?
O2 C2 N1 112(3) . . ?
O2 C2 C3 128(3) . . ?
C3 C2 N1 119(3) . . ?
N1 C13 H6 110.1 . . ?
N1 C13 H5 110.1 . . ?
N1 C13 C14 108(2) . . ?
H6 C13 H5 108.4 . . ?
C14 C13 H6 110.1 . . ?
C14 C13 H5 110.1 . . ?
C13 C14 H7 108.9 . . ?
C13 C14 H8 108.9 . . ?
C13 C14 C15 113(2) . . ?
H7 C14 H8 107.7 . . ?
C15 C14 H7 108.9 . . ?
C15 C14 H8 108.9 . . ?
C14 C15 H9 108.7 . . ?
C14 C15 H10 108.7 . . ?
H9 C15 H10 107.6 . . ?
C16 C15 C14 114(2) . . ?
C16 C15 H9 108.7 . . ?
C16 C15 H10 108.7 . . ?
C15 C16 H12 108.5 . . ?
C15 C16 H11 108.5 . . ?
H12 C16 H11 107.5 . . ?
C17 C16 C15 115(2) . . ?
C17 C16 H12 108.5 . . ?
C17 C16 H11 108.5 . . ?
C16 C17 H13 109.5 . . ?
C16 C17 H14 109.5 . . ?
C16 C17 H15 109.5 . . ?
H13 C17 H14 109.5 . . ?
H13 C17 H15 109.5 . . ?
H14 C17 H15 109.5 . . ?

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
N1 C13 C14 C15 171(3) . . . . ?
C8 C9 C10 C8 5(3) . . . 2 ?
C8 C9 C10 C11 180(2) . . . . ?
C8 C9 C4 C3 -180(2) . . . . ?
C8 C9 C4 C5 -1(3) . . . . ?
C8 C10 C11 C12 178.1(17) 2 . . . ?
C9 C8 C7 C6 0(3) . . . . ?
C9 C10 C11 C12 3(4) . . . . ?
C9 C4 C5 C6 1(3) . . . . ?
C9 C4 C5 C1 -175.2(19) . . . . ?
C10 C8 C9 C10 -5(3) 2 . . . ?
C10 C8 C9 C4 178.3(18) 2 . . . ?
C10 C8 C7 C6 -177.5(18) 2 . . . ?
C10 C9 C4 C3 3(3) . . . . ?
C10 C9 C4 C5 -178.0(18) . . . . ?
C10 C11 C12 C3 -3(3) . . . . ?
C11 C12 C3 C4 3(3) . . . . ?
C11 C12 C3 C2 -179(2) . . . . ?
C12 C3 C4 C9 -3(3) . . . . ?
C12 C3 C4 C5 178.4(16) . . . . ?
C12 C3 C2 O2 3(5) . . . . ?
C12 C3 C2 N1 179.3(19) . . . . ?
C3 C4 C5 C6 179(2) . . . . ?
C3 C4 C5 C1 4(3) . . . . ?
C4 C9 C10 C8 -178.3(19) . . . 2 ?
C4 C9 C10 C11 -3(3) . . . . ?
C4 C3 C2 O2 -179(3) . . . . ?
C4 C3 C2 N1 -3(4) . . . . ?
C4 C5 C6 C7 0(3) . . . . ?
C4 C5 C1 O1 178.4(18) . . . . ?
C4 C5 C1 N1 -5(3) . . . . ?
C5 C6 C7 C8 -1(3) . . . . ?
C6 C5 C1 O1 3(3) . . . . ?
C6 C5 C1 N1 179.4(18) . . . . ?
C7 C8 C9 C10 177.6(17) . . . . ?
C7 C8 C9 C4 0(3) . . . . ?
C1 N1 C2 O2 178(3) . . . . ?
C1 N1 C2 C3 1(3) . . . . ?
C1 N1 C13 C14 -82(3) . . . . ?
C1 C5 C6 C7 176.2(16) . . . . ?
C2 N1 C1 O1 179(2) . . . . ?
C2 N1 C1 C5 3(3) . . . . ?
C2 N1 C13 C14 92(3) . . . . ?
C2 C3 C4 C9 179.2(19) . . . . ?
C2 C3 C4 C5 0(4) . . . . ?
C13 N1 C1 O1 -6(3) . . . . ?
C13 N1 C1 C5 177.1(17) . . . . ?
C13 N1 C2 O2 4(4) . . . . ?
C13 N1 C2 C3 -173(2) . . . . ?
C13 C14 C15 C16 -180(4) . . . . ?
C14 C15 C16 C17 176(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_PDI_C8_1_50GPa
_database_code_depnum_ccdc_archive 'CCDC 2493921'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C8_1_50GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.234 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C8_1_50GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.91 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT910_PDI_C8_1_50GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         167 Note   
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT340_PDI_C8_1_50GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01607 Ang.   
RESPONSE: These data come from high-pressure experiment and part of the 
reflections can not be collected, affecting bond precision. In addition, 
despite multiple attempts to grow better diffracting crystals, it was not 
successful.
;
_vrf_PLAT911_PDI_C8_1_50GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        2413 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-02-17

_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C8
_chemical_name_systematic        N,N-Dioctyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C40 H42 N2 O4'
_chemical_formula_sum            'C40 H42 N2 O4'
_chemical_formula_weight         614.75
_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 -0.0004 0.0007 '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 -0.0003 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0008 0.0027 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.51620(10)
_cell_length_b                   16.9424(5)
_cell_length_c                   19.020(2)
_cell_angle_alpha                76.517(5)
_cell_angle_beta                 89.121(5)
_cell_angle_gamma                83.351(2)
_cell_volume                     1405.60(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1120
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.1930
_cell_measurement_theta_min      5.5470
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.997
_exptl_absorpt_coefficient_mu    0.049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.064
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.013
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0122
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.234
_diffrn_reflns_Laue_measured_fraction_max 0.208
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3480
_diffrn_reflns_point_group_measured_fraction_full 0.234
_diffrn_reflns_point_group_measured_fraction_max 0.208
_diffrn_reflns_theta_full        17.159
_diffrn_reflns_theta_max         17.977
_diffrn_reflns_theta_min         5.401
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.234
_diffrn_measured_fraction_theta_max 0.208
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     19.00  96.00   0.25    0.50  57.05   0.00-134.76    --   308
  2  φ     19.00  96.00   0.25    0.50  57.05   0.00-134.76    --   308
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.4917
_diffrn_source                   synchrotron
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 1.50(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                943
_reflns_number_total             1213
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.170
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.292
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         1213
_refine_ls_number_restraints     240
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0835
_refine_ls_restrained_S_all      1.185
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2255
_refine_ls_wR_factor_ref         0.2509
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C4)
\\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C3) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C10)
\\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C23) \\sim Ueq,
Uanis(C33) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C21)
\\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C9) \\sim Ueq,
Uanis(C28) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C35)
\\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C26) \\sim Ueq,
Uanis(C29) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C19) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C39)
\\sim Ueq, Uanis(C32) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C34(H28,H29), C36(H33,H32), C35(H31,H30), C17(H13,H14), C15(H10,H9), C14(H8,
 H7), C33(H27,H26), C13(H6,H5), C16(H11,H12), C37(H35,H34), C19(H17,H18),
 C18(H15,H16), C38(H37,H36), C39(H38,H39)
3.b Aromatic/amide H refined with riding coordinates:
 C27(H23), C7(H2), C26(H22), C6(H1), C11(H3), C31(H24), C12(H4), C32(H25)
3.c Idealised Me refined as rotating group:
 C40(H40,H41,H42), C20(H19,H20,H21)
;
_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
N1 N 1.3628(10) 0.6662(3) 0.3113(8) 0.039(7) Uani 1 1 d . . . . .
C5 C 0.9501(12) 0.7591(4) 0.3427(9) 0.030(4) Uani 1 1 d . U . . .
C4 C 0.9212(12) 0.7086(4) 0.4053(10) 0.034(4) Uani 1 1 d . U . . .
O4 O -0.2669(9) 0.7104(3) 0.7794(8) 0.076(8) Uani 1 1 d . . . . .
N2 N -0.4004(9) 0.8318(4) 0.6974(8) 0.047(7) Uani 1 1 d . . . . .
O2 O 1.5107(8) 0.5474(2) 0.3919(6) 0.082(7) Uani 1 1 d . . . . .
C24 C 0.0390(12) 0.7880(4) 0.6053(9) 0.029(4) Uani 1 1 d . U . . .
C3 C 1.1168(11) 0.6351(4) 0.4271(9) 0.031(4) Uani 1 1 d . U . . .
C8 C 0.5120(11) 0.8017(4) 0.4349(9) 0.036(4) Uani 1 1 d . U . . .
C27 C 0.0856(11) 0.8953(3) 0.4665(8) 0.033(4) Uani 1 1 d . U . . .
H23 H 0.097697 0.930085 0.421112 0.040 Uiso 1 1 calc R U . . .
C23 C 0.0040(12) 0.7356(4) 0.6692(9) 0.032(4) Uani 1 1 d . U . . .
C1 C 1.1766(14) 0.7395(5) 0.2879(11) 0.039(5) Uani 1 1 d . U . . .
C21 C -0.3841(13) 0.8865(4) 0.6328(10) 0.035(4) Uani 1 1 d . U . . .
C25 C -0.1534(12) 0.8643(4) 0.5806(10) 0.033(4) Uani 1 1 d . U . . .
O3 O -0.5515(8) 0.9497(2) 0.6179(6) 0.080(7) Uani 1 1 d . . . . .
C28 C 0.2857(12) 0.8216(4) 0.4869(9) 0.029(4) Uani 1 1 d . U . . .
C7 C 0.5483(13) 0.8520(5) 0.3688(10) 0.041(4) Uani 1 1 d . U . . .
H2 H 0.425879 0.901274 0.355804 0.050 Uiso 1 1 calc R U . . .
C2 C 1.3441(12) 0.6126(4) 0.3756(9) 0.033(4) Uani 1 1 d . U . . .
C26 C -0.1300(12) 0.9144(4) 0.5162(9) 0.033(4) Uani 1 1 d . U . . .
H22 H -0.257708 0.962823 0.503729 0.039 Uiso 1 1 calc R U . . .
O1 O 1.1995(11) 0.7818(3) 0.2262(9) 0.059(9) Uani 1 1 d . . . . .
C6 C 0.7653(11) 0.8321(4) 0.3191(8) 0.041(4) Uani 1 1 d . U . . .
H1 H 0.783385 0.865873 0.273474 0.050 Uiso 1 1 calc R U . . .
C11 C 0.8839(11) 0.6028(3) 0.5446(7) 0.036(4) Uani 1 1 d . U . . .
H3 H 0.872371 0.568234 0.590082 0.044 Uiso 1 1 calc R U . . .
C31 C 0.4071(12) 0.6448(4) 0.6395(10) 0.041(4) Uani 1 1 d . U . . .
H24 H 0.527077 0.595022 0.651431 0.050 Uiso 1 1 calc R U . . .
C12 C 1.1016(12) 0.5847(4) 0.4957(10) 0.036(4) Uani 1 1 d . U . . .
H4 H 1.238098 0.538238 0.509379 0.044 Uiso 1 1 calc R U . . .
C30 C 0.4495(11) 0.6952(3) 0.5765(8) 0.030(4) Uani 1 1 d . U . . .
C32 C 0.1881(12) 0.6626(4) 0.6899(8) 0.043(4) Uani 1 1 d . U . . .
H25 H 0.169451 0.626973 0.734583 0.052 Uiso 1 1 calc R U . . .
C22 C -0.2263(13) 0.7555(5) 0.7216(10) 0.040(4) Uani 1 1 d . U . . .
C9 C 0.7031(11) 0.7279(4) 0.4582(9) 0.027(4) Uani 1 1 d . U . . .
C10 C 0.6780(12) 0.6759(4) 0.5231(10) 0.030(4) Uani 1 1 d . U . . .
C34 C -0.4903(13) 0.8896(4) 0.8099(9) 0.052(4) Uani 1 1 d . U . . .
H28 H -0.641869 0.897999 0.844918 0.062 Uiso 1 1 calc R U . . .
H29 H -0.330389 0.850696 0.835296 0.062 Uiso 1 1 calc R U . . .
C36 C -0.2427(12) 1.0064(4) 0.8356(9) 0.047(4) Uani 1 1 d . U . . .
H33 H -0.123846 0.963096 0.869476 0.057 Uiso 1 1 calc R U . . .
H32 H -0.110131 1.045590 0.812388 0.057 Uiso 1 1 calc R U . . .
C35 C -0.3686(12) 0.9701(4) 0.7783(8) 0.052(4) Uani 1 1 d . U . . .
H31 H -0.213097 0.961511 0.744261 0.062 Uiso 1 1 calc R U . . .
H30 H -0.527025 1.008716 0.751990 0.062 Uiso 1 1 calc R U . . .
C17 C 1.7331(12) 0.4377(4) 0.0976(9) 0.056(4) Uani 1 1 d . U . . .
H13 H 1.851541 0.474406 0.065126 0.067 Uiso 1 1 calc R U . . .
H14 H 1.867536 0.399904 0.132288 0.067 Uiso 1 1 calc R U . . .
C15 C 1.6556(11) 0.5453(4) 0.1736(8) 0.052(4) Uani 1 1 d . U . . .
H10 H 1.813150 0.514440 0.206257 0.063 Uiso 1 1 calc R U . . .
H9 H 1.745387 0.584950 0.136851 0.063 Uiso 1 1 calc R U . . .
C14 C 1.4373(11) 0.5896(4) 0.2150(8) 0.041(4) Uani 1 1 d . U . . .
H8 H 1.329378 0.549963 0.247423 0.049 Uiso 1 1 calc R U . . .
H7 H 1.293797 0.625466 0.181318 0.049 Uiso 1 1 calc R U . . .
C29 C 0.2599(11) 0.7690(4) 0.5529(9) 0.031(4) Uani 1 1 d . U . . .
C33 C -0.6253(12) 0.8529(4) 0.7530(9) 0.045(4) Uani 1 1 d . U . . .
H27 H -0.709494 0.803732 0.777365 0.054 Uiso 1 1 calc R U . . .
H26 H -0.786663 0.891517 0.727988 0.054 Uiso 1 1 calc R U . . .
C13 C 1.5780(12) 0.6400(4) 0.2591(8) 0.041(4) Uani 1 1 d . U . . .
H6 H 1.751037 0.607773 0.285144 0.050 Uiso 1 1 calc R U . . .
H5 H 1.644201 0.687766 0.226824 0.050 Uiso 1 1 calc R U . . .
C16 C 1.5152(11) 0.4873(4) 0.1376(8) 0.046(4) Uani 1 1 d . U . . .
H11 H 1.363602 0.518873 0.103596 0.055 Uiso 1 1 calc R U . . .
H12 H 1.416480 0.449727 0.174305 0.055 Uiso 1 1 calc R U . . .
C40 C -0.6663(14) 1.2174(4) 0.9134(10) 0.072(7) Uani 1 1 d . U . . .
H40 H -0.743858 1.202611 0.872158 0.108 Uiso 1 1 calc R U . . .
H41 H -0.506001 1.250015 0.898637 0.108 Uiso 1 1 calc R U . . .
H42 H -0.821524 1.248218 0.934108 0.108 Uiso 1 1 calc R U . . .
C37 C -0.4700(12) 1.0484(4) 0.8776(9) 0.056(4) Uani 1 1 d . U . . .
H35 H -0.602036 1.009380 0.901434 0.067 Uiso 1 1 calc R U . . .
H34 H -0.589552 1.091900 0.844039 0.067 Uiso 1 1 calc R U . . .
C19 C 1.7824(14) 0.3363(4) 0.0154(9) 0.058(4) Uani 1 1 d . U . . .
H17 H 1.670967 0.319669 -0.020754 0.070 Uiso 1 1 calc R U . . .
H18 H 1.937475 0.367282 -0.008865 0.070 Uiso 1 1 calc R U . . .
C20 C 1.9236(18) 0.2607(4) 0.0702(9) 0.056(7) Uani 1 1 d . U . . .
H19 H 2.048297 0.226413 0.045329 0.084 Uiso 1 1 calc R U . . .
H20 H 1.769521 0.230942 0.094975 0.084 Uiso 1 1 calc R U . . .
H21 H 2.041685 0.277299 0.104527 0.084 Uiso 1 1 calc R U . . .
C18 C 1.5730(12) 0.3901(4) 0.0543(9) 0.055(4) Uani 1 1 d . U . . .
H15 H 1.444304 0.428493 0.018530 0.066 Uiso 1 1 calc R U . . .
H16 H 1.447241 0.355667 0.086626 0.066 Uiso 1 1 calc R U . . .
C38 C -0.3318(13) 1.0845(4) 0.9347(9) 0.056(4) Uani 1 1 d . U . . .
H37 H -0.239727 1.039889 0.972277 0.067 Uiso 1 1 calc R U . . .
H36 H -0.175028 1.115994 0.912083 0.067 Uiso 1 1 calc R U . . .
C39 C -0.5498(14) 1.1394(4) 0.9701(9) 0.058(4) Uani 1 1 d . U . . .
H38 H -0.449845 1.154081 1.009172 0.070 Uiso 1 1 calc R U . . .
H39 H -0.715636 1.110231 0.990124 0.070 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
N1 C1 1.400(11) . ?
N1 C2 1.350(19) . ?
N1 C13 1.485(15) . ?
C5 C4 1.31(2) . ?
C5 C1 1.52(2) . ?
C5 C6 1.394(10) . ?
C4 C3 1.421(11) . ?
C4 C9 1.461(18) . ?
O4 C22 1.21(2) . ?
N2 C21 1.36(2) . ?
N2 C22 1.414(11) . ?
N2 C33 1.530(16) . ?
O2 C2 1.240(8) . ?
C24 C23 1.35(2) . ?
C24 C25 1.455(11) . ?
C24 C29 1.461(18) . ?
C3 C2 1.487(17) . ?
C3 C12 1.39(2) . ?
C8 C28 1.477(17) . ?
C8 C7 1.36(2) . ?
C8 C9 1.417(11) . ?
C27 H23 0.9300 . ?
C27 C28 1.432(9) . ?
C27 C26 1.410(16) . ?
C23 C32 1.385(10) . ?
C23 C22 1.493(18) . ?
C1 O1 1.23(2) . ?
C21 C25 1.505(17) . ?
C21 O3 1.215(8) . ?
C25 C26 1.33(2) . ?
C28 C29 1.37(2) . ?
C7 H2 0.9300 . ?
C7 C6 1.418(16) . ?
C26 H22 0.9300 . ?
C6 H1 0.9300 . ?
C11 H3 0.9300 . ?
C11 C12 1.400(15) . ?
C11 C10 1.440(10) . ?
C31 H24 0.9300 . ?
C31 C30 1.32(2) . ?
C31 C32 1.423(17) . ?
C12 H4 0.9300 . ?
C30 C10 1.499(17) . ?
C30 C29 1.414(10) . ?
C32 H25 0.9300 . ?
C9 C10 1.35(2) . ?
C34 H28 0.9700 . ?
C34 H29 0.9700 . ?
C34 C35 1.518(13) . ?
C34 C33 1.532(17) . ?
C36 H33 0.9700 . ?
C36 H32 0.9700 . ?
C36 C35 1.517(16) . ?
C36 C37 1.505(15) . ?
C35 H31 0.9700 . ?
C35 H30 0.9700 . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C16 1.529(13) . ?
C17 C18 1.521(12) . ?
C15 H10 0.9700 . ?
C15 H9 0.9700 . ?
C15 C14 1.496(13) . ?
C15 C16 1.518(11) . ?
C14 H8 0.9700 . ?
C14 H7 0.9700 . ?
C14 C13 1.520(13) . ?
C33 H27 0.9700 . ?
C33 H26 0.9700 . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C40 H40 0.9600 . ?
C40 H41 0.9600 . ?
C40 H42 0.9600 . ?
C40 C39 1.541(17) . ?
C37 H35 0.9700 . ?
C37 H34 0.9700 . ?
C37 C38 1.538(15) . ?
C19 H17 0.9700 . ?
C19 H18 0.9700 . ?
C19 C20 1.530(16) . ?
C19 C18 1.538(14) . ?
C20 H19 0.9600 . ?
C20 H20 0.9600 . ?
C20 H21 0.9600 . ?
C18 H15 0.9700 . ?
C18 H16 0.9700 . ?
C38 H37 0.9700 . ?
C38 H36 0.9700 . ?
C38 C39 1.532(13) . ?
C39 H38 0.9700 . ?
C39 H39 0.9700 . ?

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 C13 118.1(13) . . ?
C2 N1 C1 125.3(10) . . ?
C2 N1 C13 116.3(6) . . ?
C4 C5 C1 122.0(7) . . ?
C4 C5 C6 123.3(10) . . ?
C6 C5 C1 114.5(13) . . ?
C5 C4 C3 121.2(11) . . ?
C5 C4 C9 121.9(7) . . ?
C3 C4 C9 116.8(14) . . ?
C21 N2 C22 127.6(10) . . ?
C21 N2 C33 118.8(6) . . ?
C22 N2 C33 113.6(12) . . ?
C23 C24 C25 122.9(10) . . ?
C23 C24 C29 122.1(7) . . ?
C25 C24 C29 114.9(13) . . ?
C4 C3 C2 119.1(14) . . ?
C12 C3 C4 121.2(11) . . ?
C12 C3 C2 119.7(7) . . ?
C7 C8 C28 123.0(7) . . ?
C7 C8 C9 120.5(11) . . ?
C9 C8 C28 116.5(14) . . ?
C28 C27 H23 120.4 . . ?
C26 C27 H23 120.4 . . ?
C26 C27 C28 119.1(12) . . ?
C24 C23 C32 121.1(10) . . ?
C24 C23 C22 121.3(7) . . ?
C32 C23 C22 117.6(13) . . ?
N1 C1 C5 114.8(15) . . ?
O1 C1 N1 120.4(12) . . ?
O1 C1 C5 124.9(8) . . ?
N2 C21 C25 117.0(7) . . ?
O3 C21 N2 121.3(11) . . ?
O3 C21 C25 121.7(13) . . ?
C24 C25 C21 116.8(13) . . ?
C26 C25 C24 123.4(11) . . ?
C26 C25 C21 119.8(7) . . ?
C27 C28 C8 119.1(13) . . ?
C29 C28 C8 120.6(7) . . ?
C29 C28 C27 120.3(10) . . ?
C8 C7 H2 118.7 . . ?
C8 C7 C6 122.6(7) . . ?
C6 C7 H2 118.7 . . ?
N1 C2 C3 117.4(7) . . ?
O2 C2 N1 121.8(10) . . ?
O2 C2 C3 120.7(12) . . ?
C27 C26 H22 119.5 . . ?
C25 C26 C27 120.9(7) . . ?
C25 C26 H22 119.5 . . ?
C5 C6 C7 116.1(12) . . ?
C5 C6 H1 122.0 . . ?
C7 C6 H1 122.0 . . ?
C12 C11 H3 120.6 . . ?
C12 C11 C10 118.9(12) . . ?
C10 C11 H3 120.6 . . ?
C30 C31 H24 118.2 . . ?
C30 C31 C32 123.6(6) . . ?
C32 C31 H24 118.2 . . ?
C3 C12 C11 121.0(7) . . ?
C3 C12 H4 119.5 . . ?
C11 C12 H4 119.5 . . ?
C31 C30 C10 123.5(6) . . ?
C31 C30 C29 120.9(10) . . ?
C29 C30 C10 115.4(13) . . ?
C23 C32 C31 116.9(12) . . ?
C23 C32 H25 121.6 . . ?
C31 C32 H25 121.6 . . ?
O4 C22 N2 122.0(10) . . ?
O4 C22 C23 123.7(7) . . ?
N2 C22 C23 114.3(13) . . ?
C8 C9 C4 115.5(14) . . ?
C10 C9 C4 121.5(7) . . ?
C10 C9 C8 123.0(11) . . ?
C11 C10 C30 118.2(12) . . ?
C9 C10 C11 120.4(10) . . ?
C9 C10 C30 121.2(7) . . ?
H28 C34 H29 107.7 . . ?
C35 C34 H28 108.9 . . ?
C35 C34 H29 108.9 . . ?
C35 C34 C33 113.6(11) . . ?
C33 C34 H28 108.9 . . ?
C33 C34 H29 108.9 . . ?
H33 C36 H32 107.5 . . ?
C35 C36 H33 108.4 . . ?
C35 C36 H32 108.4 . . ?
C37 C36 H33 108.4 . . ?
C37 C36 H32 108.4 . . ?
C37 C36 C35 115.4(5) . . ?
C34 C35 H31 109.0 . . ?
C34 C35 H30 109.0 . . ?
C36 C35 C34 112.8(11) . . ?
C36 C35 H31 109.0 . . ?
C36 C35 H30 109.0 . . ?
H31 C35 H30 107.8 . . ?
H13 C17 H14 107.9 . . ?
C16 C17 H13 109.2 . . ?
C16 C17 H14 109.2 . . ?
C18 C17 H13 109.2 . . ?
C18 C17 H14 109.2 . . ?
C18 C17 C16 112.1(4) . . ?
H10 C15 H9 107.8 . . ?
C14 C15 H10 109.0 . . ?
C14 C15 H9 109.0 . . ?
C14 C15 C16 113.1(4) . . ?
C16 C15 H10 109.0 . . ?
C16 C15 H9 109.0 . . ?
C15 C14 H8 108.7 . . ?
C15 C14 H7 108.7 . . ?
C15 C14 C13 114.2(4) . . ?
H8 C14 H7 107.6 . . ?
C13 C14 H8 108.7 . . ?
C13 C14 H7 108.7 . . ?
C28 C29 C24 121.4(7) . . ?
C28 C29 C30 123.3(11) . . ?
C30 C29 C24 115.3(14) . . ?
N2 C33 C34 113.5(5) . . ?
N2 C33 H27 108.9 . . ?
N2 C33 H26 108.9 . . ?
C34 C33 H27 108.9 . . ?
C34 C33 H26 108.9 . . ?
H27 C33 H26 107.7 . . ?
N1 C13 C14 111.1(5) . . ?
N1 C13 H6 109.4 . . ?
N1 C13 H5 109.4 . . ?
C14 C13 H6 109.4 . . ?
C14 C13 H5 109.4 . . ?
H6 C13 H5 108.0 . . ?
C17 C16 H11 108.5 . . ?
C17 C16 H12 108.5 . . ?
C15 C16 C17 114.9(4) . . ?
C15 C16 H11 108.5 . . ?
C15 C16 H12 108.5 . . ?
H11 C16 H12 107.5 . . ?
H40 C40 H41 109.5 . . ?
H40 C40 H42 109.5 . . ?
H41 C40 H42 109.5 . . ?
C39 C40 H40 109.5 . . ?
C39 C40 H41 109.5 . . ?
C39 C40 H42 109.5 . . ?
C36 C37 H35 108.9 . . ?
C36 C37 H34 108.9 . . ?
C36 C37 C38 113.5(5) . . ?
H35 C37 H34 107.7 . . ?
C38 C37 H35 108.9 . . ?
C38 C37 H34 108.9 . . ?
H17 C19 H18 108.2 . . ?
C20 C19 H17 109.7 . . ?
C20 C19 H18 109.7 . . ?
C20 C19 C18 109.9(12) . . ?
C18 C19 H17 109.7 . . ?
C18 C19 H18 109.7 . . ?
C19 C20 H19 109.5 . . ?
C19 C20 H20 109.5 . . ?
C19 C20 H21 109.5 . . ?
H19 C20 H20 109.5 . . ?
H19 C20 H21 109.5 . . ?
H20 C20 H21 109.5 . . ?
C17 C18 C19 114.2(5) . . ?
C17 C18 H15 108.7 . . ?
C17 C18 H16 108.7 . . ?
C19 C18 H15 108.7 . . ?
C19 C18 H16 108.7 . . ?
H15 C18 H16 107.6 . . ?
C37 C38 H37 108.5 . . ?
C37 C38 H36 108.5 . . ?
H37 C38 H36 107.5 . . ?
C39 C38 C37 115.3(6) . . ?
C39 C38 H37 108.5 . . ?
C39 C38 H36 108.5 . . ?
C40 C39 H38 109.7 . . ?
C40 C39 H39 109.7 . . ?
C38 C39 C40 109.8(12) . . ?
C38 C39 H38 109.7 . . ?
C38 C39 H39 109.7 . . ?
H38 C39 H39 108.2 . . ?

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
C5 C4 C3 C2 -4.4(15) . . . . ?
C5 C4 C3 C12 174.8(10) . . . . ?
C5 C4 C9 C8 4.5(15) . . . . ?
C5 C4 C9 C10 -179.0(9) . . . . ?
C4 C5 C1 N1 -3.9(15) . . . . ?
C4 C5 C1 O1 174.5(12) . . . . ?
C4 C5 C6 C7 3.2(14) . . . . ?
C4 C3 C2 N1 3.4(12) . . . . ?
C4 C3 C2 O2 -177.3(6) . . . . ?
C4 C3 C12 C11 2.9(15) . . . . ?
C4 C9 C10 C11 5.3(16) . . . . ?
C4 C9 C10 C30 -178.7(5) . . . . ?
N2 C21 C25 C24 -2.4(12) . . . . ?
N2 C21 C25 C26 178.8(9) . . . . ?
C24 C23 C32 C31 -2.1(13) . . . . ?
C24 C23 C22 O4 179.7(11) . . . . ?
C24 C23 C22 N2 0.8(14) . . . . ?
C24 C25 C26 C27 0.9(16) . . . . ?
C3 C4 C9 C8 179.8(6) . . . . ?
C3 C4 C9 C10 -3.6(14) . . . . ?
C8 C28 C29 C24 179.5(5) . . . . ?
C8 C28 C29 C30 2.3(16) . . . . ?
C8 C7 C6 C5 -2.5(13) . . . . ?
C8 C9 C10 C11 -178.4(6) . . . . ?
C8 C9 C10 C30 -2.3(16) . . . . ?
C27 C28 C29 C24 -2.8(16) . . . . ?
C27 C28 C29 C30 180.0(6) . . . . ?
C23 C24 C25 C21 4.7(14) . . . . ?
C23 C24 C25 C26 -176.6(10) . . . . ?
C23 C24 C29 C28 177.6(9) . . . . ?
C23 C24 C29 C30 -5.0(15) . . . . ?
C1 N1 C2 O2 177.6(7) . . . . ?
C1 N1 C2 C3 -3.1(14) . . . . ?
C1 N1 C13 C14 -88.0(8) . . . . ?
C1 C5 C4 C3 4.7(17) . . . . ?
C1 C5 C4 C9 179.8(7) . . . . ?
C1 C5 C6 C7 179.3(7) . . . . ?
C21 N2 C22 O4 -177.5(11) . . . . ?
C21 N2 C22 C23 1.4(14) . . . . ?
C21 N2 C33 C34 -96.5(11) . . . . ?
C21 C25 C26 C27 179.6(5) . . . . ?
C25 C24 C23 C32 178.5(6) . . . . ?
C25 C24 C23 C22 -3.9(16) . . . . ?
C25 C24 C29 C28 2.2(14) . . . . ?
C25 C24 C29 C30 179.5(6) . . . . ?
O3 C21 C25 C24 178.5(7) . . . . ?
O3 C21 C25 C26 -0.2(13) . . . . ?
C28 C8 C7 C6 -179.7(5) . . . . ?
C28 C8 C9 C4 178.8(6) . . . . ?
C28 C8 C9 C10 2.3(15) . . . . ?
C28 C27 C26 C25 -1.5(13) . . . . ?
C7 C8 C28 C27 2.7(14) . . . . ?
C7 C8 C28 C29 -179.6(10) . . . . ?
C7 C8 C9 C4 -3.7(15) . . . . ?
C7 C8 C9 C10 179.8(10) . . . . ?
C2 N1 C1 C5 3.2(14) . . . . ?
C2 N1 C1 O1 -175.4(11) . . . . ?
C2 N1 C13 C14 85.7(11) . . . . ?
C2 C3 C12 C11 -177.9(5) . . . . ?
C26 C27 C28 C8 -179.8(6) . . . . ?
C26 C27 C28 C29 2.4(13) . . . . ?
C6 C5 C4 C3 -179.6(6) . . . . ?
C6 C5 C4 C9 -4.4(17) . . . . ?
C6 C5 C1 N1 180.0(7) . . . . ?
C6 C5 C1 O1 -1.6(16) . . . . ?
C31 C30 C10 C11 -7.0(14) . . . . ?
C31 C30 C10 C9 176.9(9) . . . . ?
C31 C30 C29 C24 5.6(15) . . . . ?
C31 C30 C29 C28 -177.1(10) . . . . ?
C12 C3 C2 N1 -175.8(9) . . . . ?
C12 C3 C2 O2 3.5(12) . . . . ?
C12 C11 C10 C30 -179.0(6) . . . . ?
C12 C11 C10 C9 -2.8(12) . . . . ?
C30 C31 C32 C23 2.8(14) . . . . ?
C32 C23 C22 O4 -2.6(16) . . . . ?
C32 C23 C22 N2 178.5(6) . . . . ?
C32 C31 C30 C10 -179.3(6) . . . . ?
C32 C31 C30 C29 -4.8(17) . . . . ?
C22 N2 C21 C25 -0.5(14) . . . . ?
C22 N2 C21 O3 178.6(6) . . . . ?
C22 N2 C33 C34 82.3(8) . . . . ?
C22 C23 C32 C31 -179.7(6) . . . . ?
C9 C4 C3 C2 -179.7(6) . . . . ?
C9 C4 C3 C12 -0.6(13) . . . . ?
C9 C8 C28 C27 -179.9(6) . . . . ?
C9 C8 C28 C29 -2.2(14) . . . . ?
C9 C8 C7 C6 3.0(17) . . . . ?
C10 C11 C12 C3 -1.3(12) . . . . ?
C10 C30 C29 C24 -179.5(6) . . . . ?
C10 C30 C29 C28 -2.2(15) . . . . ?
C36 C37 C38 C39 170.5(11) . . . . ?
C35 C34 C33 N2 62.2(8) . . . . ?
C35 C36 C37 C38 -179.7(8) . . . . ?
C15 C14 C13 N1 -166.8(9) . . . . ?
C14 C15 C16 C17 -177.3(9) . . . . ?
C29 C24 C23 C32 3.5(16) . . . . ?
C29 C24 C23 C22 -179.0(6) . . . . ?
C29 C24 C25 C21 -179.9(6) . . . . ?
C29 C24 C25 C26 -1.2(14) . . . . ?
C29 C30 C10 C11 178.3(6) . . . . ?
C29 C30 C10 C9 2.2(14) . . . . ?
C33 N2 C21 C25 178.2(5) . . . . ?
C33 N2 C21 O3 -2.8(13) . . . . ?
C33 N2 C22 O4 3.7(14) . . . . ?
C33 N2 C22 C23 -177.4(6) . . . . ?
C33 C34 C35 C36 178.6(4) . . . . ?
C13 N1 C1 C5 176.2(6) . . . . ?
C13 N1 C1 O1 -2.3(15) . . . . ?
C13 N1 C2 O2 4.5(12) . . . . ?
C13 N1 C2 C3 -176.2(5) . . . . ?
C16 C17 C18 C19 -177.6(11) . . . . ?
C16 C15 C14 C13 172.9(9) . . . . ?
C37 C36 C35 C34 -77.9(9) . . . . ?
C37 C38 C39 C40 -66.3(8) . . . . ?
C20 C19 C18 C17 74.6(9) . . . . ?
C18 C17 C16 C15 -172.0(9) . . . . ?

_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_PDI_C5_1_73GPa
_database_code_depnum_ccdc_archive 'CCDC 2493898'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PDI_C5_1_73GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      15.00 Degree
RESPONSE: Due to the specificity of the applied measuring technique and use 
of a diamond-anvil cell limiting the access of the X-ray radiation to the 
measured sample. A full set of data was collected.
;
_vrf_PLAT029_PDI_C5_1_73GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.338 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C5_1_73GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.34 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C5_1_73GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.04333 Ang. 
RESPONSE: The data come from high-pressure experiment, and part of the 
reflection can not be collected, affecting the bond precision.
;
_vrf_PLAT911_PDI_C5_1_73GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        477 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-08-05

_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C5
_chemical_name_systematic        N,N-Dipentyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C34 H30 N2 O4'
_chemical_formula_sum            'C34 H30 N2 O4'
_chemical_formula_weight         530.60
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.4671(8)
_cell_length_b                   8.3465(11)
_cell_length_c                   15.502(7)
_cell_angle_alpha                85.32(3)
_cell_angle_beta                 83.75(3)
_cell_angle_gamma                86.216(13)
_cell_volume                     571.7(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    811
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2450
_cell_measurement_theta_min      4.5790
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.451
_exptl_absorpt_correction_T_min  0.374
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 11 1 0.1114
0 0 -21 0.0213
0 0 21 0.0213
-6 -2 -4 0.0596
-6 -4 -4 0.0663
1 -11 -1 0.1283
6 4 4 0.0669
6 2 4 0.0551

_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.042
_exptl_oxdiff_absorpt_process_details 
;
Gaussian integration over a grid
of 16 x 16 x 16 points =  4096 total grid points
  Based upon method of Burnham (1966)

 Data corrected for diamond-anvil cell absorption
 Note that exptl_absorpt_correction_tmin and _tmax
 the total correction factors applied to the intensities
 The individual factors are: 
         range of dac transmission factors (min-max)      0.404     0.453
         range of gasket transmission (min-max)           0.911     1.000
         range of P media transmission (min-max)          1.000     1.000

 thickness of diamond anvil 1: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 1:  0.000 mm, mu =  0.0000 mm-1

 thickness of diamond anvil 2: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 2:  0.000 mm, mu =  0.0000 mm-1

    Gasket shadowing corrections were made based upon
    Gasket thickness = 170.0 microns, radius = 180.0 microns
    Gasket absorption coeff =        21.00 mm-1
    REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF 
 FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00

    Non-absorbing pressure medium
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_Laue_measured_fraction_full 0.338
_diffrn_reflns_Laue_measured_fraction_max 0.172
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            1738
_diffrn_reflns_point_group_measured_fraction_full 0.338
_diffrn_reflns_point_group_measured_fraction_max 0.172
_diffrn_reflns_theta_full        15.000
_diffrn_reflns_theta_max         26.847
_diffrn_reflns_theta_min         4.651
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.338
_diffrn_measured_fraction_theta_max 0.172
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.25  49.00   0.75    7.50    --    0.16 -53.00  17.00   83
  2  ω    -13.25  49.00   0.75    7.50    --    0.16 -53.00-162.00   83
  3  ω    -22.25  40.00   0.75   20.00    --  -30.73 -26.00   7.00   83
  4  ω    -66.25  -4.00   0.75   20.00    --  -30.73  97.00 -35.00   83
  5  ω    -35.25  27.00   0.75   20.00    --  -30.73  13.00 176.00   83
  6  ω     13.75  40.00   0.75   20.00    --  -30.73-114.00-135.00   35
  7  ω    -54.25   8.00   0.75   20.00    --  -30.73  67.00 157.00   83
  8  ω    -13.25  22.00   0.75   20.00    --  -30.73 -53.00-162.00   47
  9  ω    -13.25  22.00   0.75   20.00    --  -30.73 -53.00  17.00   47
 10  ω      5.00  29.00   0.75   20.00    --  -30.73 -97.00  35.00   32
 11  ω    -43.25 -11.00   0.75   20.00    --  -30.73  19.00   0.00   43
 12  ω     38.00  89.00   0.75   20.00    --   31.04-135.00-123.00   68
 13  ω     21.00  56.25   0.75   20.00    --   31.04 -77.00-150.00   47
 14  ω    -39.25 -13.00   0.75   20.00    --   31.04 114.00 -45.00   35
 15  ω    -14.25  36.00   0.75   20.00    --   31.04 -13.00   3.00   67
 16  ω     21.00  56.25   0.75   20.00    --   31.04 -77.00  30.00   47
 17  ω    -21.25  14.00   0.75   20.00    --   31.04  53.00 -17.00   47
 18  ω    -30.00   0.00   0.75   20.00    --   31.04   0.00-150.00   40
 19  ω    -70.00 -13.75   0.75    7.50    --    0.16 114.00 135.00   75
 20  ω    -53.00 -26.00   0.75    7.50    --    0.16  37.00   0.00   36
 21  ω    -53.00 -26.00   0.75   20.00    --  -30.73  37.00   0.00   36
 22  ω    -18.25  44.00   0.75   20.00    --  -30.73 -39.00-167.00   83
 23  ω     -9.25  44.00   0.75   20.00    --   31.04 -19.00-180.00   71
 24  ω    -21.25  14.00   0.75   20.00    --   31.04  53.00 162.00   47
 25  ω     -5.00  19.00   0.75   20.00    --   31.04  57.00 -30.00   32
 26  ω     25.00  76.00   0.75   20.00    --   31.04-114.00  45.00   68
 27  ω    -31.00  23.00   0.75   20.00    --   31.04  26.00  -7.00   72
 28  ω    -39.25 -13.00   0.75   20.00    --   31.04 114.00 135.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 1.73(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                204
_reflns_number_total             425
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.160
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         425
_refine_ls_number_restraints     357
_refine_ls_R_factor_all          0.1860
_refine_ls_R_factor_gt           0.0967
_refine_ls_restrained_S_all      0.718
_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)+(0.0001P)²+9.9485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.2119
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C4-C9 \\sim C10-C9 \\sim C11-C10 \\sim C12-C11 \\sim C3-C12 \\sim C4-C3 \\sim
C3-C2 \\sim C5-C4 \\sim C5-C1 ~
 C6-C5 \\sim C6-C7 \\sim C7-C8 \\sim C9-C8
 with sigma of 0.02
 O2-C2 \\sim O1-C1
 with sigma of 0.02
 N1-C13 \\sim C14-C13 \\sim C15-C14 \\sim C16-C15 \\sim C17-C16
 with sigma of 0.02
 N1-C1 \\sim N1-C2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(N1) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C4)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C9) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(O1) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C6) \\sim Ueq,
Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 O1, N1, C8, C9, C10, C11, C12, C3, C4, C5, C6, C7, C1, C2, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C13(H6,H5), C14(H8,H7), C15(H9,H10), C16(H11,H12)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H3), C12(H4), C6(H1), C7(H2)
5.c Idealised Me refined as rotating group:
 C17(H15,H14,H13)
;
_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 -1.051(4) 0.4520(16) 0.126(3) 0.041(9) Uani 1 1 d D U . . .
O2 O -0.829(5) 0.0596(19) 0.336(3) 0.040(7) Uani 1 1 d D U . . .
N1 N -0.944(5) 0.250(2) 0.232(2) 0.031(7) Uani 1 1 d D U . . .
C8 C -0.191(6) 0.136(2) -0.024(3) 0.024(8) Uani 1 1 d D U . . .
C9 C -0.231(5) 0.064(2) 0.062(3) 0.022(8) Uani 1 1 d D U . . .
C10 C -0.061(6) -0.077(2) 0.089(3) 0.027(11) Uani 1 1 d D U . . .
C11 C -0.124(7) -0.145(3) 0.174(3) 0.040(11) Uani 1 1 d D U . . .
H3 H -0.003562 -0.234141 0.192549 0.048 Uiso 1 1 calc R U . . .
C12 C -0.360(5) -0.087(2) 0.234(3) 0.031(11) Uani 1 1 d D U . . .
H4 H -0.401628 -0.136160 0.289661 0.037 Uiso 1 1 calc R U . . .
C3 C -0.527(5) 0.050(2) 0.203(2) 0.026(7) Uani 1 1 d D U . . .
C4 C -0.478(5) 0.125(2) 0.117(2) 0.022(7) Uani 1 1 d D U . . .
C5 C -0.658(5) 0.263(2) 0.093(2) 0.029(7) Uani 1 1 d D U . . .
C6 C -0.600(5) 0.329(3) 0.007(3) 0.027(7) Uani 1 1 d D U . . .
H1 H -0.725633 0.414933 -0.012109 0.033 Uiso 1 1 calc R U . . .
C7 C -0.366(4) 0.272(2) -0.054(3) 0.030(8) Uani 1 1 d D U . . .
H2 H -0.328957 0.320960 -0.109363 0.036 Uiso 1 1 calc R U . . .
C1 C -0.899(6) 0.327(3) 0.148(3) 0.029(7) Uani 1 1 d D U . . .
C2 C -0.767(6) 0.114(3) 0.259(3) 0.027(7) Uani 1 1 d D U . . .
C13 C -1.165(5) 0.329(3) 0.300(3) 0.039(8) Uani 1 1 d D U . . .
H6 H -1.235341 0.247164 0.344192 0.047 Uiso 1 1 calc R U . . .
H5 H -1.338265 0.376894 0.272764 0.047 Uiso 1 1 calc R U . . .
C14 C -1.022(5) 0.459(2) 0.343(3) 0.038(7) Uani 1 1 d D U . . .
H8 H -0.879569 0.407201 0.381397 0.046 Uiso 1 1 calc R U . . .
H7 H -0.908581 0.525464 0.298655 0.046 Uiso 1 1 calc R U . . .
C15 C -1.245(5) 0.569(2) 0.397(4) 0.038(7) Uani 1 1 d D U . . .
H9 H -1.405026 0.610922 0.361923 0.046 Uiso 1 1 calc R U . . .
H10 H -1.336097 0.507687 0.447660 0.046 Uiso 1 1 calc R U . . .
C16 C -1.081(5) 0.707(2) 0.424(4) 0.040(7) Uani 1 1 d D U . . .
H11 H -0.984150 0.765986 0.373542 0.048 Uiso 1 1 calc R U . . .
H12 H -0.926851 0.665424 0.461083 0.048 Uiso 1 1 calc R U . . .
C17 C -1.310(5) 0.820(3) 0.475(4) 0.061(11) Uani 1 1 d D U . . .
H15 H -1.358155 0.772635 0.532655 0.091 Uiso 1 1 calc R U . . .
H14 H -1.490190 0.834977 0.445610 0.091 Uiso 1 1 calc R U . . .
H13 H -1.225085 0.921681 0.476935 0.091 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 1.24(3) . ?
O2 C2 1.25(4) . ?
N1 C1 1.40(4) . ?
N1 C2 1.41(3) . ?
N1 C13 1.53(2) . ?
C8 C9 1.41(2) . ?
C8 C10 1.51(6) 2 ?
C8 C7 1.410(17) . ?
C9 C10 1.411(18) . ?
C9 C4 1.416(19) . ?
C10 C11 1.41(2) . ?
C11 H3 0.9300 . ?
C11 C12 1.41(2) . ?
C12 H4 0.9300 . ?
C12 C3 1.408(18) . ?
C3 C4 1.42(2) . ?
C3 C2 1.415(19) . ?
C4 C5 1.415(18) . ?
C5 C6 1.41(2) . ?
C5 C1 1.40(2) . ?
C6 H1 0.9300 . ?
C6 C7 1.41(2) . ?
C7 H2 0.9300 . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.532(18) . ?
C14 H8 0.9700 . ?
C14 H7 0.9700 . ?
C14 C15 1.53(2) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.523(17) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C17 1.53(2) . ?
C17 H15 0.9600 . ?
C17 H14 0.9600 . ?
C17 H13 0.9600 . ?

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 C2 123(3) . . ?
C1 N1 C13 119(2) . . ?
C2 N1 C13 117(3) . . ?
C9 C8 C10 121(2) . 2 ?
C7 C8 C9 124(3) . . ?
C7 C8 C10 115(3) . 2 ?
C8 C9 C4 117(2) . . ?
C10 C9 C8 122(3) . . ?
C10 C9 C4 120(3) . . ?
C9 C10 C8 116(3) . 2 ?
C11 C10 C8 125(3) . 2 ?
C11 C10 C9 119(3) . . ?
C10 C11 H3 118.1 . . ?
C10 C11 C12 124(3) . . ?
C12 C11 H3 118.1 . . ?
C11 C12 H4 122.5 . . ?
C3 C12 C11 115(3) . . ?
C3 C12 H4 122.5 . . ?
C12 C3 C4 124(3) . . ?
C12 C3 C2 118(3) . . ?
C2 C3 C4 118(2) . . ?
C9 C4 C3 118(2) . . ?
C5 C4 C9 122(3) . . ?
C5 C4 C3 120(3) . . ?
C6 C5 C4 116(3) . . ?
C1 C5 C4 123(3) . . ?
C1 C5 C6 120(3) . . ?
C5 C6 H1 117.8 . . ?
C7 C6 C5 124(3) . . ?
C7 C6 H1 117.8 . . ?
C8 C7 H2 122.1 . . ?
C6 C7 C8 116(3) . . ?
C6 C7 H2 122.1 . . ?
O1 C1 N1 121(3) . . ?
O1 C1 C5 123(4) . . ?
C5 C1 N1 116(3) . . ?
O2 C2 N1 116(3) . . ?
O2 C2 C3 123(3) . . ?
N1 C2 C3 120(3) . . ?
N1 C13 H6 109.2 . . ?
N1 C13 H5 109.2 . . ?
N1 C13 C14 112(2) . . ?
H6 C13 H5 107.9 . . ?
C14 C13 H6 109.2 . . ?
C14 C13 H5 109.2 . . ?
C13 C14 H8 108.6 . . ?
C13 C14 H7 108.6 . . ?
H8 C14 H7 107.5 . . ?
C15 C14 C13 114.8(19) . . ?
C15 C14 H8 108.6 . . ?
C15 C14 H7 108.6 . . ?
C14 C15 H9 109.8 . . ?
C14 C15 H10 109.8 . . ?
H9 C15 H10 108.2 . . ?
C16 C15 C14 109(2) . . ?
C16 C15 H9 109.8 . . ?
C16 C15 H10 109.8 . . ?
C15 C16 H11 109.9 . . ?
C15 C16 H12 109.9 . . ?
C15 C16 C17 109(2) . . ?
H11 C16 H12 108.3 . . ?
C17 C16 H11 109.9 . . ?
C17 C16 H12 109.9 . . ?
C16 C17 H15 109.5 . . ?
C16 C17 H14 109.5 . . ?
C16 C17 H13 109.5 . . ?
H15 C17 H14 109.5 . . ?
H15 C17 H13 109.5 . . ?
H14 C17 H13 109.5 . . ?

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
N1 C13 C14 C15 167(2) . . . . ?
C8 C9 C10 C8 7(4) . . . 2 ?
C8 C9 C10 C11 -177(3) . . . . ?
C8 C9 C4 C3 178(2) . . . . ?
C8 C9 C4 C5 -8(3) . . . . ?
C8 C10 C11 C12 179(2) 2 . . . ?
C9 C8 C7 C6 -4(3) . . . . ?
C9 C10 C11 C12 4(4) . . . . ?
C9 C4 C5 C6 7(3) . . . . ?
C9 C4 C5 C1 -179(2) . . . . ?
C10 C8 C9 C10 -7(4) 2 . . . ?
C10 C8 C9 C4 -178.3(18) 2 . . . ?
C10 C8 C7 C6 -179.6(19) 2 . . . ?
C10 C9 C4 C3 7(3) . . . . ?
C10 C9 C4 C5 -179(2) . . . . ?
C10 C11 C12 C3 -2(4) . . . . ?
C11 C12 C3 C4 3(3) . . . . ?
C11 C12 C3 C2 180(2) . . . . ?
C12 C3 C4 C9 -5(3) . . . . ?
C12 C3 C4 C5 -179.6(19) . . . . ?
C12 C3 C2 O2 4(4) . . . . ?
C12 C3 C2 N1 -179(2) . . . . ?
C3 C4 C5 C6 -179(2) . . . . ?
C3 C4 C5 C1 -4(3) . . . . ?
C4 C9 C10 C8 177.7(19) . . . 2 ?
C4 C9 C10 C11 -6(3) . . . . ?
C4 C3 C2 O2 -179(3) . . . . ?
C4 C3 C2 N1 -2(3) . . . . ?
C4 C5 C6 C7 -5(4) . . . . ?
C4 C5 C1 O1 178(2) . . . . ?
C4 C5 C1 N1 4(3) . . . . ?
C5 C6 C7 C8 3(3) . . . . ?
C6 C5 C1 O1 -8(4) . . . . ?
C6 C5 C1 N1 178(2) . . . . ?
C7 C8 C9 C10 176.9(18) . . . . ?
C7 C8 C9 C4 6(3) . . . . ?
C1 N1 C2 O2 179(3) . . . . ?
C1 N1 C2 C3 2(3) . . . . ?
C1 N1 C13 C14 -82(3) . . . . ?
C1 C5 C6 C7 -179.3(19) . . . . ?
C2 N1 C1 O1 -177(2) . . . . ?
C2 N1 C1 C5 -2(3) . . . . ?
C2 N1 C13 C14 90(3) . . . . ?
C2 C3 C4 C9 177.9(19) . . . . ?
C2 C3 C4 C5 3(3) . . . . ?
C13 N1 C1 O1 -5(3) . . . . ?
C13 N1 C1 C5 169.5(18) . . . . ?
C13 N1 C2 O2 7(3) . . . . ?
C13 N1 C2 C3 -170(2) . . . . ?
C13 C14 C15 C16 -171(4) . . . . ?
C14 C15 C16 C17 178(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
- Detector area 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_PDI_C5_2_70GPa
_database_code_depnum_ccdc_archive 'CCDC 2493900'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PDI_C5_2_70GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      15.00 Degree
RESPONSE: Due to the specificity of the applied measuring technique and use 
of a diamond-anvil cell limiting the access of the X-ray radiation to the 
measured sample. A full set of data was collected.
;
_vrf_PLAT029_PDI_C5_2_70GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.348 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C5_2_70GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.48 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C5_2_70GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.05222 Ang.  
RESPONSE: The data come from high-pressure experiment, and part of the 
reflection can not be collected, affecting the bond precision.
;
_vrf_PLAT411_PDI_C5_2_70GPa      
;
PROBLEM: Short Inter H...H Contact  H1       ..H1       .       1.97 Ang.  
                                               -2-x,-1-y,-z  =      2_345 Check 
RESPONSE: These data come from high-pressure studies, and the short distance 
is likely a result of poor data quality.
;
_vrf_PLAT413_PDI_C5_2_70GPa      
;
PROBLEM: Short Inter XH3 .. XHn     H14      ..H14      .       1.94 Ang.  
                                              1-x,-2-y,-1-z  =      2_634 Check   
RESPONSE: These data come from high-pressure studies, and the short distance 
is likely a result of poor data quality.
;
_vrf_PLAT910_PDI_C5_2_70GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note  
RESPONSE:The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT911_PDI_C5_2_70GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        447 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-02-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C5
_chemical_name_systematic        N,N-Dipentyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C34 H30 N2 O4'
_chemical_formula_sum            'C34 H30 N2 O4'
_chemical_formula_weight         530.60
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.7203(3)
_cell_length_b                   8.5616(7)
_cell_length_c                   17.928(7)
_cell_angle_alpha                87.10(2)
_cell_angle_beta                 74.75(2)
_cell_angle_gamma                101.539(7)
_cell_volume                     536.6(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    452
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.250
_cell_measurement_theta_min      4.890
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.108
_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    1.642
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.041
_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.348
_diffrn_reflns_Laue_measured_fraction_max 0.189
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2487
_diffrn_reflns_point_group_measured_fraction_full 0.348
_diffrn_reflns_point_group_measured_fraction_max 0.189
_diffrn_reflns_theta_full        15.000
_diffrn_reflns_theta_max         27.250
_diffrn_reflns_theta_min         4.890
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.348
_diffrn_measured_fraction_theta_max 0.189
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 2.70(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                237
_reflns_number_total             452
_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         0.176
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         452
_refine_ls_number_restraints     318
_refine_ls_R_factor_all          0.1542
_refine_ls_R_factor_gt           0.0790
_refine_ls_restrained_S_all      0.795
_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)+(0.1069P)²+4.9602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2115
_refine_ls_wR_factor_ref         0.2788
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C4-C3 \\sim C3-C2 \\sim C5-C1 \\sim C5-C4 \\sim C4-C9 \\sim C9-C8 \\sim C7-C8
\\sim C6-C7 \\sim C6-C5 \\sim C10-
 C8 \\sim C11-C10 \\sim C12-C11
 with sigma of 0.02
 O2-C2 \\sim O1-C1
 with sigma of 0.02
 C14-C13 \\sim C15-C14 \\sim C16-C15 \\sim C17-C16
 with sigma of 0.02
 N1-C1 \\sim N1-C2
 with sigma of 0.02
3. Rigid bond restraints
 C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O2, O1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
O2 \\sim O1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
Uanis(C13) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.04
Uanis(O1) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(C4) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim
Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of
0.04
5. Rigid body (RIGU) restrains
 C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12, C11, C10, C8, C9, C7, C6, C5, C4, C3, C2, N1, C1, O1, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Secondary CH2 refined with riding coordinates:
 C13(H6,H5), C14(H8,H7), C15(H10,H9), C16(H11,H12)
6.b Aromatic/amide H refined with riding coordinates:
 C11(H3), C12(H4), C6(H1), C7(H2)
6.c Idealised Me refined as rotating group:
 C17(H13,H14,H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.681(3) -0.5008(11) -0.1849(19) 0.024(11) Uani 1 1 d D U . . .
O2 O 0.289(5) -0.1107(15) -0.345(3) 0.039(7) Uani 1 1 d D . . . .
N1 N -0.186(5) -0.3098(16) -0.263(3) 0.028(5) Uani 1 1 d D U . . .
C8 C -0.272(5) -0.1477(18) 0.005(3) 0.021(6) Uani 1 1 d D U . . .
C9 C -0.043(5) -0.0789(19) -0.070(3) 0.017(6) Uani 1 1 d D U . . .
C10 C -0.220(6) -0.070(2) 0.070(3) 0.024(7) Uani 1 1 d D . . . .
C11 C -0.423(6) -0.135(3) 0.147(3) 0.027(8) Uani 1 1 d D . . . .
H3 H -0.587280 -0.235168 0.154015 0.032 Uiso 1 1 calc R U . . .
C12 C -0.394(6) -0.0575(19) 0.213(3) 0.027(8) Uani 1 1 d D . . . .
H4 H -0.559702 -0.105380 0.260707 0.033 Uiso 1 1 calc R U . . .
C3 C 0.131(5) -0.088(2) -0.213(3) 0.016(6) Uani 1 1 d D . . . .
C4 C -0.090(5) -0.1521(18) -0.137(3) 0.021(6) Uani 1 1 d D U . . .
C5 C -0.362(5) -0.2969(18) -0.126(3) 0.022(5) Uani 1 1 d D . . . .
C6 C -0.589(5) -0.358(2) -0.050(3) 0.024(6) Uani 1 1 d D U . . .
H1 H -0.779911 -0.449445 -0.044410 0.029 Uiso 1 1 calc R U . . .
C7 C -0.549(5) -0.2898(18) 0.018(3) 0.030(6) Uani 1 1 d D U . . .
H2 H -0.696123 -0.336014 0.067515 0.036 Uiso 1 1 calc R U . . .
C1 C -0.426(5) -0.378(2) -0.190(3) 0.021(5) Uani 1 1 d D U . . .
C2 C 0.080(6) -0.163(2) -0.278(3) 0.021(6) Uani 1 1 d D . . . .
C13 C -0.219(6) -0.3937(17) -0.329(4) 0.022(6) Uani 1 1 d D U . . .
H6 H -0.025738 -0.333646 -0.374627 0.026 Uiso 1 1 calc R U . . .
H5 H -0.465564 -0.390659 -0.337233 0.026 Uiso 1 1 calc R U . . .
C14 C -0.180(5) -0.5702(15) -0.328(3) 0.021(5) Uani 1 1 d D U . . .
H8 H -0.026564 -0.588575 -0.293359 0.025 Uiso 1 1 calc R U . . .
H7 H -0.430699 -0.640355 -0.307307 0.025 Uiso 1 1 calc R U . . .
C15 C 0.008(5) -0.6117(17) -0.410(3) 0.024(5) Uani 1 1 d D U . . .
H10 H 0.258340 -0.540667 -0.430238 0.029 Uiso 1 1 calc R U . . .
H9 H -0.145772 -0.593689 -0.443925 0.029 Uiso 1 1 calc R U . . .
C16 C 0.053(5) -0.7878(17) -0.409(3) 0.022(6) Uani 1 1 d D U . . .
H11 H 0.192645 -0.808566 -0.372455 0.027 Uiso 1 1 calc R U . . .
H12 H -0.197706 -0.859565 -0.392528 0.027 Uiso 1 1 calc R U . . .
C17 C 0.268(5) -0.8205(19) -0.491(3) 0.033(7) Uani 1 1 d D U . . .
H13 H 0.101643 -0.827594 -0.524324 0.050 Uiso 1 1 calc R U . . .
H14 H 0.349105 -0.919608 -0.487620 0.050 Uiso 1 1 calc R U . . .
H15 H 0.487695 -0.734540 -0.512690 0.050 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 1.249(18) . ?
O2 C2 1.24(3) . ?
N1 C1 1.39(3) . ?
N1 C2 1.40(2) . ?
N1 C13 1.45(6) . ?
C8 C9 1.413(18) . ?
C8 C10 1.411(18) . ?
C8 C7 1.394(15) . ?
C9 C10 1.44(3) 2 ?
C9 C4 1.411(18) . ?
C10 C11 1.406(19) . ?
C11 H3 0.9300 . ?
C11 C12 1.408(19) . ?
C12 H4 0.9300 . ?
C12 C3 1.42(2) 2 ?
C3 C4 1.409(18) . ?
C3 C2 1.405(18) . ?
C4 C5 1.404(16) . ?
C5 C6 1.408(19) . ?
C5 C1 1.418(19) . ?
C6 H1 0.9300 . ?
C6 C7 1.405(19) . ?
C7 H2 0.9300 . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.546(17) . ?
C14 H8 0.9700 . ?
C14 H7 0.9700 . ?
C14 C15 1.54(3) . ?
C15 H10 0.9700 . ?
C15 H9 0.9700 . ?
C15 C16 1.549(17) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C17 1.55(3) . ?
C17 H13 0.9600 . ?
C17 H14 0.9600 . ?
C17 H15 0.9600 . ?

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 C2 126(3) . . ?
C1 N1 C13 118.1(19) . . ?
C2 N1 C13 116(3) . . ?
C10 C8 C9 118.9(15) . . ?
C7 C8 C9 123(3) . . ?
C7 C8 C10 118(3) . . ?
C8 C9 C10 114(3) . 2 ?
C4 C9 C8 120.7(15) . . ?
C4 C9 C10 126(4) . 2 ?
C8 C10 C9 127(4) . 2 ?
C11 C10 C8 122.2(17) . . ?
C11 C10 C9 110(4) . 2 ?
C10 C11 H3 118.0 . . ?
C10 C11 C12 124.1(19) . . ?
C12 C11 H3 118.0 . . ?
C11 C12 H4 117.5 . . ?
C11 C12 C3 125(3) . 2 ?
C3 C12 H4 117.5 2 . ?
C4 C3 C12 112(3) . 2 ?
C2 C3 C12 126(4) . 2 ?
C2 C3 C4 122.0(16) . . ?
C3 C4 C9 122.9(14) . . ?
C5 C4 C9 118(3) . . ?
C5 C4 C3 119(3) . . ?
C4 C5 C6 119(3) . . ?
C4 C5 C1 121(3) . . ?
C6 C5 C1 119.7(15) . . ?
C5 C6 H1 117.5 . . ?
C7 C6 C5 125.1(16) . . ?
C7 C6 H1 117.5 . . ?
C8 C7 C6 114(3) . . ?
C8 C7 H2 122.8 . . ?
C6 C7 H2 122.8 . . ?
O1 C1 N1 119(3) . . ?
O1 C1 C5 125(3) . . ?
N1 C1 C5 115.7(17) . . ?
O2 C2 N1 122(3) . . ?
O2 C2 C3 121.5(19) . . ?
N1 C2 C3 116(3) . . ?
N1 C13 H6 107.7 . . ?
N1 C13 H5 107.7 . . ?
N1 C13 C14 118(4) . . ?
H6 C13 H5 107.1 . . ?
C14 C13 H6 107.7 . . ?
C14 C13 H5 107.7 . . ?
C13 C14 H8 109.3 . . ?
C13 C14 H7 109.3 . . ?
H8 C14 H7 108.0 . . ?
C15 C14 C13 112(3) . . ?
C15 C14 H8 109.3 . . ?
C15 C14 H7 109.3 . . ?
C14 C15 H10 109.1 . . ?
C14 C15 H9 109.1 . . ?
C14 C15 C16 112(3) . . ?
H10 C15 H9 107.9 . . ?
C16 C15 H10 109.1 . . ?
C16 C15 H9 109.1 . . ?
C15 C16 H11 109.5 . . ?
C15 C16 H12 109.5 . . ?
H11 C16 H12 108.1 . . ?
C17 C16 C15 111(3) . . ?
C17 C16 H11 109.5 . . ?
C17 C16 H12 109.5 . . ?
C16 C17 H13 109.5 . . ?
C16 C17 H14 109.5 . . ?
C16 C17 H15 109.5 . . ?
H13 C17 H14 109.5 . . ?
H13 C17 H15 109.5 . . ?
H14 C17 H15 109.5 . . ?

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
N1 C13 C14 C15 -147(2) . . . . ?
C8 C9 C4 C3 179.9(16) . . . . ?
C8 C9 C4 C5 -2(2) . . . . ?
C8 C10 C11 C12 -176.9(16) . . . . ?
C9 C8 C10 C9 1(3) . . . 2 ?
C9 C8 C10 C11 -177(2) . . . . ?
C9 C8 C7 C6 -1(2) . . . . ?
C9 C10 C11 C12 5(3) 2 . . . ?
C9 C4 C5 C6 3(3) . . . . ?
C9 C4 C5 C1 -180.0(16) . . . . ?
C10 C8 C9 C10 -1(3) . . . 2 ?
C10 C8 C9 C4 -179.1(17) . . . . ?
C10 C8 C7 C6 178.4(17) . . . . ?
C10 C9 C4 C3 2(3) 2 . . . ?
C10 C9 C4 C5 -179.7(16) 2 . . . ?
C10 C11 C12 C3 -7(3) . . . 2 ?
C12 C3 C4 C9 -1(2) 2 . . . ?
C12 C3 C4 C5 -179.4(14) 2 . . . ?
C12 C3 C2 O2 5(3) 2 . . . ?
C12 C3 C2 N1 177.3(15) 2 . . . ?
C3 C4 C5 C6 -178.1(17) . . . . ?
C3 C4 C5 C1 -2(3) . . . . ?
C4 C3 C2 O2 -176(2) . . . . ?
C4 C3 C2 N1 -4(2) . . . . ?
C4 C5 C6 C7 -4(3) . . . . ?
C4 C5 C1 O1 -174.8(16) . . . . ?
C4 C5 C1 N1 4(2) . . . . ?
C5 C6 C7 C8 3(3) . . . . ?
C6 C5 C1 O1 2(3) . . . . ?
C6 C5 C1 N1 -179.6(17) . . . . ?
C7 C8 C9 C10 178.9(15) . . . 2 ?
C7 C8 C9 C4 1(3) . . . . ?
C7 C8 C10 C9 -178.8(16) . . . 2 ?
C7 C8 C10 C11 4(3) . . . . ?
C1 N1 C2 O2 179.0(19) . . . . ?
C1 N1 C2 C3 7(3) . . . . ?
C1 N1 C13 C14 -55(3) . . . . ?
C1 C5 C6 C7 178.9(16) . . . . ?
C2 N1 C1 O1 172.0(15) . . . . ?
C2 N1 C1 C5 -7(2) . . . . ?
C2 N1 C13 C14 127(2) . . . . ?
C2 C3 C4 C9 179.9(16) . . . . ?
C2 C3 C4 C5 1(3) . . . . ?
C13 N1 C1 O1 -6(2) . . . . ?
C13 N1 C1 C5 175.4(16) . . . . ?
C13 N1 C2 O2 -3(3) . . . . ?
C13 N1 C2 C3 -175.4(16) . . . . ?
C13 C14 C15 C16 179.6(16) . . . . ?
C14 C15 C16 C17 -175.9(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_PDI_C5_2_17GPa
_database_code_depnum_ccdc_archive 'CCDC 2493899'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PDI_C5_2_17GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      15.00 Degree
RESPONSE: Due to the specificity of the applied measuring technique and use 
of a diamond-anvil cell limiting the access of the X-ray radiation to the 
measured sample.  A full set of data was collected.
;
_vrf_PLAT029_PDI_C5_2_17GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.354 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C5_2_17GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.53 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C5_2_17GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.05111 Ang. 
RESPONSE: The data come from high-pressure experiment, and part of the 
reflection can not be collected, affecting the bond precision.
;
_vrf_PLAT910_PDI_C5_2_17GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note   
RESPONSE: The unit cell is reasonable large and these low angle 
reflections are probably missing due to the beamstop.
;
_vrf_PLAT911_PDI_C5_2_17GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        413 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-12-04

_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C5
_chemical_name_systematic        N,N-Dipentyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C34 H30 N2 O4'
_chemical_formula_sum            'C34 H30 N2 O4'
_chemical_formula_weight         530.60
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.7606(6)
_cell_length_b                   8.5729(5)
_cell_length_c                   18.044(6)
_cell_angle_alpha                87.221(17)
_cell_angle_beta                 74.48(3)
_cell_angle_gamma                101.631(8)
_cell_volume                     545.8(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    934
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2990
_cell_measurement_theta_min      4.8770
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.452
_exptl_absorpt_correction_T_min  0.344
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 5 -4 0.0701
-2 -10 -4 0.1348
5 -6 4 0.0729
2 10 4 0.1186
-5 1 -7 0.0917
0 0 1 0.0174
5 -1 5 0.0959
-1 0 -25 0.0148

_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.041
_exptl_oxdiff_absorpt_process_details 
;
Gaussian integration over a grid
of 16 x 16 x 16 points =  4096 total grid points
  Based upon method of Burnham (1966)

 Data corrected for diamond-anvil cell absorption
 Note that exptl_absorpt_correction_tmin and _tmax
 the total correction factors applied to the intensities
 The individual factors are: 
         range of dac transmission factors (min-max)      0.404     0.453
         range of gasket transmission (min-max)           0.846     1.000
         range of P media transmission (min-max)          1.000     1.000

 thickness of diamond anvil 1: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 1:  0.000 mm, mu =  0.0000 mm-1

 thickness of diamond anvil 2: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 2:  0.000 mm, mu =  0.0000 mm-1

    Gasket shadowing corrections were made based upon
    Gasket thickness = 190.0 microns, radius = 195.0 microns
    Gasket absorption coeff =        21.00 mm-1
    REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF 
 FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00

    Non-absorbing pressure medium
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.354
_diffrn_reflns_Laue_measured_fraction_max 0.196
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2859
_diffrn_reflns_point_group_measured_fraction_full 0.354
_diffrn_reflns_point_group_measured_fraction_max 0.196
_diffrn_reflns_theta_full        15.000
_diffrn_reflns_theta_max         26.917
_diffrn_reflns_theta_min         4.884
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.354
_diffrn_measured_fraction_theta_max 0.196
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.25  49.00   0.75    7.50    --    0.16 -53.00  17.00   83
  2  ω    -13.25  49.00   0.75    7.50    --    0.16 -53.00-162.00   83
  3  ω    -22.25  40.00   0.75   20.00    --  -30.73 -26.00   7.00   83
  4  ω    -66.25  -4.00   0.75   20.00    --  -30.73  97.00 -35.00   83
  5  ω    -35.25  27.00   0.75   20.00    --  -30.73  13.00 176.00   83
  6  ω     13.75  40.00   0.75   20.00    --  -30.73-114.00-135.00   35
  7  ω    -54.25   8.00   0.75   20.00    --  -30.73  67.00 157.00   83
  8  ω    -13.25  22.00   0.75   20.00    --  -30.73 -53.00-162.00   47
  9  ω    -13.25  22.00   0.75   20.00    --  -30.73 -53.00  17.00   47
 10  ω      5.00  29.00   0.75   20.00    --  -30.73 -97.00  35.00   32
 11  ω    -43.25 -11.00   0.75   20.00    --  -30.73  19.00   0.00   43
 12  ω     38.00  89.00   0.75   20.00    --   31.04-135.00-123.00   68
 13  ω     21.00  56.25   0.75   20.00    --   31.04 -77.00-150.00   47
 14  ω    -39.25 -13.00   0.75   20.00    --   31.04 114.00 -45.00   35
 15  ω    -14.25  36.00   0.75   20.00    --   31.04 -13.00   3.00   67
 16  ω     21.00  56.25   0.75   20.00    --   31.04 -77.00  30.00   47
 17  ω    -21.25  14.00   0.75   20.00    --   31.04  53.00 -17.00   47
 18  ω    -30.00   0.00   0.75   20.00    --   31.04   0.00-150.00   40
 19  ω    -70.00 -13.75   0.75    7.50    --    0.16 114.00 135.00   75
 20  ω    -53.00 -26.00   0.75    7.50    --    0.16  37.00   0.00   36
 21  ω    -53.00 -26.00   0.75   20.00    --  -30.73  37.00   0.00   36
 22  ω    -18.25  44.00   0.75   20.00    --  -30.73 -39.00-167.00   83
 23  ω     -9.25  44.00   0.75   20.00    --   31.04 -19.00-180.00   71
 24  ω    -21.25  14.00   0.75   20.00    --   31.04  53.00 162.00   47
 25  ω     -5.00  19.00   0.75   20.00    --   31.04  57.00 -30.00   32
 26  ω     25.00  76.00   0.75   20.00    --   31.04-114.00  45.00   68
 27  ω    -31.00  23.00   0.75   20.00    --   31.04  26.00  -7.00   72
 28  ω    -39.25 -13.00   0.75   20.00    --   31.04 114.00 135.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 2.17(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                264
_reflns_number_total             460
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.200
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         460
_refine_ls_number_restraints     352
_refine_ls_R_factor_all          0.1491
_refine_ls_R_factor_gt           0.0898
_refine_ls_restrained_S_all      0.786
_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)+(0.0615P)²+6.9914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2091
_refine_ls_wR_factor_ref         0.2502
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O1-C1 \\sim O2-C2
 with sigma of 0.02
 N1-C2 \\sim N1-C1
 with sigma of 0.02
 C3-C2 \\sim C4-C3 \\sim C5-C4 \\sim C5-C1 \\sim C6-C5 \\sim C4-C9 \\sim C6-C7
\\sim C7-C8 \\sim C9-C8 \\sim C10-
 C8 \\sim C11-C10 \\sim C12-C11
 with sigma of 0.02
 C14-C13 \\sim C15-C14 \\sim C16-C15 \\sim C17-C16
 with sigma of 0.02
2. Rigid bond restraints
 O2, C2, O1, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C2, N1, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O2 \\sim O1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
C2 \\sim C3 \\sim C4 \\sim C5 \\sim C1 \\sim C6 \\sim C8 \\sim C9 \\sim C7
\\sim C10 \\sim C11 \\sim C12: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17: 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: with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms
of 0.2
Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq: with sigma of
0.02 and sigma for terminal atoms of 0.04
Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C2) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C10) \\sim Ueq: with sigma of
0.02 and sigma for terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 C2, C3, C1, N1, C5, C4, C9, C8, C10, C11, C12, C7, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C17, C16, C15, C14, C13
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Secondary CH2 refined with riding coordinates:
 C13(H6,H5), C14(H8,H7), C15(H9,H10), C16(H12,H11)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H3), C12(H4), C6(H1), C7(H2)
5.c Idealised Me refined as rotating group:
 C17(H14,H13,H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.676(3) -0.4970(12) -0.185(2) 0.04(3) Uani 1 1 d D U . . .
O2 O 0.297(5) -0.1113(15) -0.342(2) 0.042(11) Uani 1 1 d D U . . .
N1 N -0.171(5) -0.3099(16) -0.265(3) 0.027(9) Uani 1 1 d D U . . .
C8 C -0.278(5) -0.1466(18) 0.009(3) 0.020(7) Uani 1 1 d D U . . .
C9 C -0.051(6) -0.0771(18) -0.066(3) 0.018(7) Uani 1 1 d D U . . .
C10 C -0.223(6) -0.069(2) 0.074(3) 0.019(8) Uani 1 1 d D U . . .
C11 C -0.429(6) -0.133(2) 0.150(3) 0.025(8) Uani 1 1 d D U . . .
H3 H -0.596379 -0.232302 0.157050 0.030 Uiso 1 1 calc R U . . .
C12 C -0.398(6) -0.0592(19) 0.217(3) 0.031(8) Uani 1 1 d D U . . .
H4 H -0.552463 -0.105200 0.265647 0.037 Uiso 1 1 calc R U . . .
C3 C 0.129(5) -0.086(2) -0.209(2) 0.015(7) Uani 1 1 d D U . . .
C4 C -0.090(6) -0.1507(18) -0.133(3) 0.021(7) Uani 1 1 d D U . . .
C5 C -0.357(6) -0.2954(17) -0.127(3) 0.018(9) Uani 1 1 d D U . . .
C6 C -0.588(6) -0.359(2) -0.053(3) 0.024(9) Uani 1 1 d D U . . .
H1 H -0.776315 -0.450858 -0.047484 0.029 Uiso 1 1 calc R U . . .
C7 C -0.548(5) -0.2904(17) 0.015(3) 0.023(9) Uani 1 1 d D U . . .
H2 H -0.700097 -0.339641 0.063200 0.028 Uiso 1 1 calc R U . . .
C1 C -0.413(6) -0.374(2) -0.192(3) 0.019(9) Uani 1 1 d D U . . .
C2 C 0.090(6) -0.163(2) -0.274(3) 0.016(7) Uani 1 1 d D U . . .
C13 C -0.212(7) -0.3922(18) -0.328(4) 0.026(9) Uani 1 1 d D U . . .
H6 H -0.026390 -0.332985 -0.373615 0.032 Uiso 1 1 calc R U . . .
H5 H -0.460191 -0.390666 -0.333563 0.032 Uiso 1 1 calc R U . . .
C14 C -0.171(5) -0.5682(15) -0.325(3) 0.021(7) Uani 1 1 d D U . . .
H8 H -0.418826 -0.639066 -0.304786 0.025 Uiso 1 1 calc R U . . .
H7 H -0.018418 -0.585274 -0.291369 0.025 Uiso 1 1 calc R U . . .
C15 C 0.017(5) -0.6089(17) -0.407(3) 0.023(7) Uani 1 1 d D U . . .
H9 H -0.131836 -0.587608 -0.441429 0.027 Uiso 1 1 calc R U . . .
H10 H 0.266769 -0.538724 -0.427116 0.027 Uiso 1 1 calc R U . . .
C16 C 0.058(5) -0.7849(17) -0.410(3) 0.021(6) Uani 1 1 d D U . . .
H12 H -0.192502 -0.855328 -0.394795 0.025 Uiso 1 1 calc R U . . .
H11 H 0.187834 -0.809569 -0.372449 0.025 Uiso 1 1 calc R U . . .
C17 C 0.279(5) -0.8169(19) -0.491(3) 0.027(7) Uani 1 1 d D U . . .
H14 H 0.127305 -0.813595 -0.525993 0.041 Uiso 1 1 calc R U . . .
H13 H 0.337364 -0.920625 -0.487982 0.041 Uiso 1 1 calc R U . . .
H15 H 0.509765 -0.736443 -0.509563 0.041 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 1.27(2) . ?
O2 C2 1.26(3) . ?
N1 C1 1.40(3) . ?
N1 C2 1.40(2) . ?
N1 C13 1.39(6) . ?
C8 C9 1.418(18) . ?
C8 C10 1.414(18) . ?
C8 C7 1.410(15) . ?
C9 C10 1.43(2) 2 ?
C9 C4 1.416(18) . ?
C10 C11 1.412(18) . ?
C11 H3 0.9300 . ?
C11 C12 1.411(19) . ?
C12 H4 0.9300 . ?
C12 C3 1.41(2) 2 ?
C3 C4 1.411(18) . ?
C3 C2 1.410(18) . ?
C4 C5 1.409(15) . ?
C5 C6 1.408(19) . ?
C5 C1 1.413(19) . ?
C6 H1 0.9300 . ?
C6 C7 1.407(19) . ?
C7 H2 0.9300 . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.547(17) . ?
C14 H8 0.9700 . ?
C14 H7 0.9700 . ?
C14 C15 1.55(3) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.548(17) . ?
C16 H12 0.9700 . ?
C16 H11 0.9700 . ?
C16 C17 1.55(2) . ?
C17 H14 0.9600 . ?
C17 H13 0.9600 . ?
C17 H15 0.9600 . ?

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 C2 120(3) . . ?
C13 N1 C1 118(2) . . ?
C13 N1 C2 122(4) . . ?
C10 C8 C9 118.7(14) . . ?
C7 C8 C9 118(3) . . ?
C7 C8 C10 123(3) . . ?
C8 C9 C10 119(4) . 2 ?
C4 C9 C8 121.2(15) . . ?
C4 C9 C10 120(4) . 2 ?
C8 C10 C9 122(4) . 2 ?
C11 C10 C8 122.0(16) . . ?
C11 C10 C9 116(4) . 2 ?
C10 C11 H3 117.6 . . ?
C12 C11 C10 124.9(18) . . ?
C12 C11 H3 117.6 . . ?
C11 C12 H4 120.6 . . ?
C3 C12 C11 119(4) 2 . ?
C3 C12 H4 120.6 2 . ?
C12 C3 C4 118(3) 2 . ?
C2 C3 C12 120(4) . 2 ?
C2 C3 C4 122.2(17) . . ?
C3 C4 C9 123.2(15) . . ?
C5 C4 C9 121(3) . . ?
C5 C4 C3 116(3) . . ?
C4 C5 C1 124(3) . . ?
C6 C5 C4 117(3) . . ?
C6 C5 C1 119.3(16) . . ?
C5 C6 H1 118.3 . . ?
C7 C6 C5 123.3(17) . . ?
C7 C6 H1 118.3 . . ?
C8 C7 H2 120.1 . . ?
C6 C7 C8 120(3) . . ?
C6 C7 H2 120.1 . . ?
O1 C1 N1 120(3) . . ?
O1 C1 C5 122(3) . . ?
N1 C1 C5 117.8(19) . . ?
O2 C2 N1 117(3) . . ?
O2 C2 C3 123.0(19) . . ?
N1 C2 C3 120(3) . . ?
N1 C13 H6 107.8 . . ?
N1 C13 H5 107.8 . . ?
N1 C13 C14 118(4) . . ?
H6 C13 H5 107.2 . . ?
C14 C13 H6 107.8 . . ?
C14 C13 H5 107.8 . . ?
C13 C14 H8 109.4 . . ?
C13 C14 H7 109.4 . . ?
C13 C14 C15 111(4) . . ?
H8 C14 H7 108.0 . . ?
C15 C14 H8 109.4 . . ?
C15 C14 H7 109.4 . . ?
C14 C15 H9 108.8 . . ?
C14 C15 H10 108.8 . . ?
H9 C15 H10 107.7 . . ?
C16 C15 C14 114(3) . . ?
C16 C15 H9 108.8 . . ?
C16 C15 H10 108.8 . . ?
C15 C16 H12 109.2 . . ?
C15 C16 H11 109.2 . . ?
C15 C16 C17 112(3) . . ?
H12 C16 H11 107.9 . . ?
C17 C16 H12 109.2 . . ?
C17 C16 H11 109.2 . . ?
C16 C17 H14 109.5 . . ?
C16 C17 H13 109.5 . . ?
C16 C17 H15 109.5 . . ?
H14 C17 H13 109.5 . . ?
H14 C17 H15 109.5 . . ?
H13 C17 H15 109.5 . . ?

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
N1 C13 C14 C15 -145(3) . . . . ?
C8 C9 C4 C3 -179.9(17) . . . . ?
C8 C9 C4 C5 0(3) . . . . ?
C8 C10 C11 C12 -177.5(16) . . . . ?
C9 C8 C10 C9 0(3) . . . 2 ?
C9 C8 C10 C11 -178(2) . . . . ?
C9 C8 C7 C6 -1(2) . . . . ?
C9 C10 C11 C12 5(3) 2 . . . ?
C9 C4 C5 C6 2(3) . . . . ?
C9 C4 C5 C1 179.3(17) . . . . ?
C10 C8 C9 C10 0(3) . . . 2 ?
C10 C8 C9 C4 179.2(16) . . . . ?
C10 C8 C7 C6 179.2(17) . . . . ?
C10 C9 C4 C3 -1(3) 2 . . . ?
C10 C9 C4 C5 179.6(16) 2 . . . ?
C10 C11 C12 C3 -4(3) . . . 2 ?
C12 C3 C4 C9 0(3) 2 . . . ?
C12 C3 C4 C5 179.5(14) 2 . . . ?
C12 C3 C2 O2 3(3) 2 . . . ?
C12 C3 C2 N1 178.3(16) 2 . . . ?
C3 C4 C5 C6 -177.8(17) . . . . ?
C3 C4 C5 C1 0(3) . . . . ?
C4 C3 C2 O2 -176.3(19) . . . . ?
C4 C3 C2 N1 -1(3) . . . . ?
C4 C5 C6 C7 -4(3) . . . . ?
C4 C5 C1 O1 -174.1(16) . . . . ?
C4 C5 C1 N1 4(3) . . . . ?
C5 C6 C7 C8 3(3) . . . . ?
C6 C5 C1 O1 3(3) . . . . ?
C6 C5 C1 N1 -178.4(18) . . . . ?
C7 C8 C9 C10 179.7(14) . . . 2 ?
C7 C8 C9 C4 -1(2) . . . . ?
C7 C8 C10 C9 -179.7(15) . . . 2 ?
C7 C8 C10 C11 2(3) . . . . ?
C1 N1 C2 O2 -179.4(19) . . . . ?
C1 N1 C2 C3 5(3) . . . . ?
C1 N1 C13 C14 -58(3) . . . . ?
C1 C5 C6 C7 178.8(16) . . . . ?
C2 N1 C1 O1 172.1(15) . . . . ?
C2 N1 C1 C5 -6(3) . . . . ?
C2 N1 C13 C14 125(3) . . . . ?
C2 C3 C4 C9 178.9(16) . . . . ?
C2 C3 C4 C5 -1(3) . . . . ?
C13 N1 C1 O1 -5(3) . . . . ?
C13 N1 C1 C5 176.5(17) . . . . ?
C13 N1 C2 O2 -2(3) . . . . ?
C13 N1 C2 C3 -178.1(18) . . . . ?
C13 C14 C15 C16 -178.4(17) . . . . ?
C14 C15 C16 C17 -174.8(14) . . . . ?

_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
- Detector area 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_PDI_C7_0_1MPa
_database_code_depnum_ccdc_archive 'CCDC 2493902'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C7_0_1MPa       
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.310 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C7_0_1MPa       
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.01 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT910_PDI_C7_0_1MPa       
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         82 Note  
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT911_PDI_C7_0_1MPa       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        1814 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-06-09

_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        N,N-Diheptyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_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 -0.0004 0.0007 '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 -0.0003 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0008 0.0027 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8301(2)
_cell_length_b                   8.3661(4)
_cell_length_c                   19.3233(7)
_cell_angle_alpha                79.542(4)
_cell_angle_beta                 88.704(3)
_cell_angle_gamma                81.683(4)
_cell_volume                     759.79(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    670
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.7300
_cell_measurement_theta_min      5.6150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.044
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.099
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.019
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.310
_diffrn_reflns_Laue_measured_fraction_max 0.217
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            1468
_diffrn_reflns_point_group_measured_fraction_full 0.310
_diffrn_reflns_point_group_measured_fraction_max 0.217
_diffrn_reflns_theta_full        17.166
_diffrn_reflns_theta_max         23.028
_diffrn_reflns_theta_min         5.268
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.310
_diffrn_measured_fraction_theta_max 0.217
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     22.00  59.75   0.25    1.00  57.05   0.00-134.76    --   151
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.4919
_diffrn_source                   synchrotron
_diffrn_special_details          
;
 Data were collected at room conditions (296 K / 0.1 MPa)
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1178
_reflns_number_total             1395
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.101
_refine_diff_density_min         -0.103
_refine_diff_density_rms         0.022
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1395
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.096
_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)+(0.1490P)²+0.0238P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2016
_refine_ls_wR_factor_ref         0.2087
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C18-C19B \\sim C18-C19A
 with sigma of 0.02
2. Others
 Sof(H18A)=Sof(H18B)=Sof(C19B)=Sof(H19D)=Sof(H19E)=Sof(H19F)=1-FVAR(1)
 Sof(H18C)=Sof(H18D)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C18(H18C,H18D)
3.b Me refined with riding coordinates:
 C19A(H19A,H19B,H19C), C19B(H19D,H19E,H19F)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C6(H6), C11(H11), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 1.0088(4) 0.0903(3) 0.38836(7) 0.0603(11) Uani 1 1 d . . . . .
O1 O 0.6709(4) 0.5366(3) 0.22679(7) 0.0751(13) Uani 1 1 d . . . . .
N1 N 0.8414(4) 0.3133(3) 0.30759(8) 0.0494(11) Uani 1 1 d . . . . .
C5 C 0.4370(4) 0.5038(3) 0.33592(8) 0.0430(10) Uani 1 1 d . . . . .
C4 C 0.4235(4) 0.4083(3) 0.40400(8) 0.0384(9) Uani 1 1 d . . . . .
C10 C 0.2047(4) 0.3559(3) 0.52052(7) 0.0370(9) Uani 1 1 d . . . . .
C3 C 0.6244(4) 0.2660(3) 0.42387(9) 0.0420(9) Uani 1 1 d . . . . .
C8 C 0.0126(4) 0.5974(3) 0.43045(8) 0.0385(9) Uani 1 1 d . . . . .
C13 C 1.0464(5) 0.2577(4) 0.25549(10) 0.0549(13) Uani 1 1 d . . . . .
H6 H 1.216565 0.201291 0.279607 0.066 Uiso 1 1 calc R U . . .
H5 H 1.093238 0.352326 0.222787 0.066 Uiso 1 1 calc R U . . .
C9 C 0.2117(4) 0.4533(3) 0.45175(8) 0.0368(9) Uani 1 1 d . . . . .
C14 C 0.9276(6) 0.1429(5) 0.21511(11) 0.0611(15) Uani 1 1 d . . . . .
H7 H 0.771846 0.204178 0.186391 0.073 Uiso 1 1 calc R U . . .
H8 H 0.856234 0.057214 0.248397 0.073 Uiso 1 1 calc R U . . .
C12 C 0.6171(4) 0.1764(3) 0.49112(9) 0.0433(9) Uani 1 1 d . . . . .
H4 H 0.752372 0.085774 0.505126 0.052 Uiso 1 1 calc R U . . .
C6 C 0.2449(5) 0.6446(3) 0.31694(8) 0.0501(10) Uani 1 1 d . . . . .
H1 H 0.255844 0.709446 0.272739 0.060 Uiso 1 1 calc R U . . .
C11 C 0.4103(4) 0.2199(3) 0.53820(8) 0.0428(9) Uani 1 1 d . . . . .
H3 H 0.408964 0.156169 0.582943 0.051 Uiso 1 1 calc R U . . .
C2 C 0.8382(5) 0.2153(4) 0.37398(9) 0.0447(10) Uani 1 1 d . . . . .
C7 C 0.0365(4) 0.6896(3) 0.36331(8) 0.0484(10) Uani 1 1 d . . . . .
H2 H -0.090870 0.783959 0.349184 0.058 Uiso 1 1 calc R U . . .
C15 C 1.1419(7) 0.0638(5) 0.16798(12) 0.0645(17) Uani 1 1 d . . . . .
H9 H 1.204578 0.149561 0.132966 0.077 Uiso 1 1 calc R U . . .
H10 H 1.302932 0.008860 0.196334 0.077 Uiso 1 1 calc R U . . .
C1 C 0.6532(5) 0.4569(4) 0.28568(8) 0.0504(11) Uani 1 1 d . . . . .
C16 C 1.0333(7) -0.0592(5) 0.13060(12) 0.0683(18) Uani 1 1 d . . . . .
H12 H 0.959683 -0.140878 0.165536 0.082 Uiso 1 1 calc R U . . .
H11 H 0.879340 -0.002487 0.100138 0.082 Uiso 1 1 calc R U . . .
C17 C 1.2464(12) -0.1457(9) 0.08735(19) 0.094(3) Uani 1 1 d . . . . .
H13 H 1.328839 -0.061907 0.055559 0.112 Uiso 1 1 calc R U . . .
H14 H 1.393862 -0.205805 0.119117 0.112 Uiso 1 1 calc R U . . .
C18 C 1.1655(17) -0.2593(11) 0.0455(3) 0.098(4) Uani 1 1 d D . . . .
H15A H 0.987414 -0.214669 0.022477 0.117 Uiso 0.404(14) 1 calc R U P A 1
H16A H 1.304568 -0.275496 0.009421 0.117 Uiso 0.404(14) 1 calc R U P A 1
H16B H 1.007516 -0.302901 0.069906 0.117 Uiso 0.596(14) 1 calc R U P A 2
H15B H 1.090838 -0.190984 0.002021 0.117 Uiso 0.596(14) 1 calc R U P A 2
C19A C 1.145(3) -0.4009(17) 0.0871(3) 0.126(8) Uani 0.596(14) 1 d D . P A 1
H18A H 1.091477 -0.476717 0.059857 0.189 Uiso 0.596(14) 1 calc R U P A 1
H19A H 1.322168 -0.444775 0.109422 0.189 Uiso 0.596(14) 1 calc R U P A 1
H17A H 1.005996 -0.384136 0.122437 0.189 Uiso 0.596(14) 1 calc R U P A 1
C19B C 1.326(5) -0.391(4) 0.0254(10) 0.16(2) Uani 0.404(14) 1 d D . P A 2
H18B H 1.215628 -0.442921 -0.002030 0.245 Uiso 0.404(14) 1 calc R U P A 2
H17B H 1.480737 -0.354633 -0.002235 0.245 Uiso 0.404(14) 1 calc R U P A 2
H19B H 1.396398 -0.467917 0.066480 0.245 Uiso 0.404(14) 1 calc R U P A 2


_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 C2 1.227(2) . ?
O1 C1 1.218(2) . ?
N1 C13 1.484(2) . ?
N1 C2 1.392(2) . ?
N1 C1 1.402(2) . ?
C5 C4 1.415(2) . ?
C5 C6 1.387(2) . ?
C5 C1 1.470(2) . ?
C4 C3 1.422(2) . ?
C4 C9 1.419(2) . ?
C10 C8 1.457(2) 2_566 ?
C10 C9 1.430(2) . ?
C10 C11 1.395(2) . ?
C3 C12 1.380(2) . ?
C3 C2 1.467(2) . ?
C8 C9 1.431(2) . ?
C8 C7 1.396(2) . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.520(6) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C15 1.522(3) . ?
C12 H4 0.9300 . ?
C12 C11 1.390(2) . ?
C6 H1 0.9300 . ?
C6 C7 1.389(2) . ?
C11 H3 0.9300 . ?
C7 H2 0.9300 . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.517(7) . ?
C16 H12 0.9700 . ?
C16 H11 0.9700 . ?
C16 C17 1.499(4) . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C18 1.453(13) . ?
C18 H15A 0.9700 . ?
C18 H16A 0.9700 . ?
C18 H16B 0.9700 . ?
C18 H15B 0.9700 . ?
C18 C19A 1.322(14) . ?
C18 C19B 1.364(14) . ?
C19A H18A 0.9600 . ?
C19A H19A 0.9600 . ?
C19A H17A 0.9600 . ?
C19B H18B 0.9600 . ?
C19B H17B 0.9600 . ?
C19B H19B 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C13 118.05(16) . . ?
C2 N1 C1 124.03(17) . . ?
C1 N1 C13 117.84(16) . . ?
C4 C5 C1 120.92(15) . . ?
C6 C5 C4 119.26(16) . . ?
C6 C5 C1 119.81(16) . . ?
C5 C4 C3 119.16(16) . . ?
C5 C4 C9 120.48(15) . . ?
C9 C4 C3 120.36(16) . . ?
C9 C10 C8 119.28(14) . 2_566 ?
C11 C10 C8 122.54(14) . 2_566 ?
C11 C10 C9 118.17(15) . . ?
C4 C3 C2 120.70(16) . . ?
C12 C3 C4 119.07(16) . . ?
C12 C3 C2 120.23(14) . . ?
C9 C8 C10 119.30(15) . 2_566 ?
C7 C8 C10 122.25(15) . 2_566 ?
C7 C8 C9 118.44(16) . . ?
N1 C13 H6 109.5 . . ?
N1 C13 H5 109.5 . . ?
N1 C13 C14 110.8(3) . . ?
H6 C13 H5 108.1 . . ?
C14 C13 H6 109.5 . . ?
C14 C13 H5 109.5 . . ?
C4 C9 C10 119.37(14) . . ?
C4 C9 C8 119.20(16) . . ?
C10 C9 C8 121.41(16) . . ?
C13 C14 H7 109.0 . . ?
C13 C14 H8 109.0 . . ?
C13 C14 C15 113.1(3) . . ?
H7 C14 H8 107.8 . . ?
C15 C14 H7 109.0 . . ?
C15 C14 H8 109.0 . . ?
C3 C12 H4 119.6 . . ?
C3 C12 C11 120.84(13) . . ?
C11 C12 H4 119.6 . . ?
C5 C6 H1 119.7 . . ?
C5 C6 C7 120.67(15) . . ?
C7 C6 H1 119.7 . . ?
C10 C11 H3 118.9 . . ?
C12 C11 C10 122.13(14) . . ?
C12 C11 H3 118.9 . . ?
O2 C2 N1 119.64(18) . . ?
O2 C2 C3 122.58(17) . . ?
N1 C2 C3 117.77(15) . . ?
C8 C7 H2 119.0 . . ?
C6 C7 C8 121.92(15) . . ?
C6 C7 H2 119.0 . . ?
C14 C15 H9 108.7 . . ?
C14 C15 H10 108.7 . . ?
H9 C15 H10 107.6 . . ?
C16 C15 C14 114.1(4) . . ?
C16 C15 H9 108.7 . . ?
C16 C15 H10 108.7 . . ?
O1 C1 N1 120.07(18) . . ?
O1 C1 C5 122.54(17) . . ?
N1 C1 C5 117.38(16) . . ?
C15 C16 H12 108.6 . . ?
C15 C16 H11 108.6 . . ?
H12 C16 H11 107.5 . . ?
C17 C16 C15 114.8(5) . . ?
C17 C16 H12 108.6 . . ?
C17 C16 H11 108.6 . . ?
C16 C17 H13 107.2 . . ?
C16 C17 H14 107.2 . . ?
H13 C17 H14 106.9 . . ?
C18 C17 C16 120.3(7) . . ?
C18 C17 H13 107.2 . . ?
C18 C17 H14 107.2 . . ?
C17 C18 H15A 109.9 . . ?
C17 C18 H16A 109.9 . . ?
C17 C18 H16B 105.2 . . ?
C17 C18 H15B 105.2 . . ?
H15A C18 H16A 108.3 . . ?
H16B C18 H15B 105.9 . . ?
C19A C18 C17 108.9(5) . . ?
C19A C18 H15A 109.9 . . ?
C19A C18 H16A 109.9 . . ?
C19B C18 C17 128.3(13) . . ?
C19B C18 H16B 105.2 . . ?
C19B C18 H15B 105.2 . . ?
C18 C19A H18A 109.5 . . ?
C18 C19A H19A 109.5 . . ?
C18 C19A H17A 109.5 . . ?
H18A C19A H19A 109.5 . . ?
H18A C19A H17A 109.5 . . ?
H19A C19A H17A 109.5 . . ?
C18 C19B H18B 109.5 . . ?
C18 C19B H17B 109.5 . . ?
C18 C19B H19B 109.5 . . ?
H18B C19B H17B 109.5 . . ?
H18B C19B H19B 109.5 . . ?
H17B C19B H19B 109.5 . . ?

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
N1 C13 C14 C15 -172.24(18) . . . . ?
C5 C4 C3 C12 177.7(3) . . . . ?
C5 C4 C3 C2 -1.8(5) . . . . ?
C5 C4 C9 C10 -179.3(2) . . . . ?
C5 C4 C9 C8 -0.5(5) . . . . ?
C5 C6 C7 C8 0.6(6) . . . . ?
C4 C5 C6 C7 -1.7(6) . . . . ?
C4 C5 C1 O1 -179.8(3) . . . . ?
C4 C5 C1 N1 0.9(6) . . . . ?
C4 C3 C12 C11 2.6(5) . . . . ?
C4 C3 C2 O2 -177.4(3) . . . . ?
C4 C3 C2 N1 1.5(5) . . . . ?
C10 C8 C9 C4 -179.8(2) 2_566 . . . ?
C10 C8 C9 C10 -1.0(5) 2_566 . . . ?
C10 C8 C7 C6 179.7(3) 2_566 . . . ?
C3 C4 C9 C10 1.1(5) . . . . ?
C3 C4 C9 C8 179.9(3) . . . . ?
C3 C12 C11 C10 -1.0(5) . . . . ?
C8 C10 C9 C4 179.8(2) 2_566 . . . ?
C8 C10 C9 C8 1.0(5) 2_566 . . . ?
C8 C10 C11 C12 -179.9(3) 2_566 . . . ?
C13 N1 C2 O2 2.4(5) . . . . ?
C13 N1 C2 C3 -176.5(3) . . . . ?
C13 N1 C1 O1 -3.9(6) . . . . ?
C13 N1 C1 C5 175.4(3) . . . . ?
C13 C14 C15 C16 176.4(2) . . . . ?
C9 C4 C3 C12 -2.7(5) . . . . ?
C9 C4 C3 C2 177.9(3) . . . . ?
C9 C10 C11 C12 -0.6(5) . . . . ?
C9 C8 C7 C6 0.6(5) . . . . ?
C14 C15 C16 C17 -176.5(3) . . . . ?
C12 C3 C2 O2 3.1(5) . . . . ?
C12 C3 C2 N1 -177.9(3) . . . . ?
C6 C5 C4 C3 -178.7(3) . . . . ?
C6 C5 C4 C9 1.7(6) . . . . ?
C6 C5 C1 O1 -0.6(6) . . . . ?
C6 C5 C1 N1 -179.9(3) . . . . ?
C11 C10 C9 C4 0.5(5) . . . . ?
C11 C10 C9 C8 -178.2(2) . . . . ?
C2 N1 C13 C14 86.9(3) . . . . ?
C2 N1 C1 O1 179.5(3) . . . . ?
C2 N1 C1 C5 -1.2(6) . . . . ?
C2 C3 C12 C11 -177.9(3) . . . . ?
C7 C8 C9 C4 -0.7(5) . . . . ?
C7 C8 C9 C10 178.1(2) . . . . ?
C15 C16 C17 C18 -176.2(4) . . . . ?
C1 N1 C13 C14 -89.9(4) . . . . ?
C1 N1 C2 O2 179.0(3) . . . . ?
C1 N1 C2 C3 0.1(6) . . . . ?
C1 C5 C4 C3 0.6(5) . . . . ?
C1 C5 C4 C9 -179.1(3) . . . . ?
C1 C5 C6 C7 179.0(3) . . . . ?
C16 C17 C18 C19A -78.8(7) . . . . ?
C16 C17 C18 C19B -152.6(16) . . . . ?

_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_PDI_C7_320K
_database_code_depnum_ccdc_archive 'CCDC 2493910'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
_vrf_PLAT088_PDI_C7_320K         
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.64 Note
RESPONSE: These data come from high-temperature studies, and the 
poor data quality is related to the progressive increase in thermal 
motions and low symmetry. 
;
# start Validation Reply Form
_vrf_THETM01_PDI_C7_320K         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.4717
RESPONSE: Due to the low symmetry some of the data can not be collected.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-03-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        'N,N Diheptyl 3,4,9,10 perylenedicarboximide'
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8258(9)
_cell_length_b                   8.3561(13)
_cell_length_c                   19.307(4)
_cell_angle_alpha                79.577(10)
_cell_angle_beta                 88.648(11)
_cell_angle_gamma                81.636(10)
_cell_volume                     757.6(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2198
_cell_measurement_temperature    320
_cell_measurement_theta_max      20.933
_cell_measurement_theta_min      2.505
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.4876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1540 before and 0.1087 after correction.
The Ratio of minimum to maximum transmission is 0.6548.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1345
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22724
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        21.257
_diffrn_reflns_theta_max         21.257
_diffrn_reflns_theta_min         2.145
_diffrn_ambient_temperature      320
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          
;
 Data were collected at high temperature of 320 K.
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1048
_reflns_number_total             1654
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.165
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1654
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.042
_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)+(0.0754P)²+0.2631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1652
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C19A-C18 \\sim C18-C19B
 with sigma of 0.02
2. Rigid body (RIGU) restrains
 C19A, C18, C19B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(H15B)=Sof(H16B)=Sof(C19B)=Sof(H18B)=Sof(H19B)=Sof(H17B)=1-FVAR(1)
 Sof(H16A)=Sof(H15A)=Sof(C19A)=Sof(H17A)=Sof(H18A)=Sof(H19A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C13(H5,H6), C14(H7,H8), C15(H9,H10), C16(H11,H12), C17(H13,H14), C18(H16A,
 H15A), C18(H15B,H16B)
4.b Me refined with riding coordinates:
 C19A(H17A,H18A,H19A), C19B(H18B,H19B,H17B)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H2), C6(H1), C12(H4), C11(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0076(5) 0.5907(3) 0.38828(12) 0.0697(8) Uani 1 1 d . . . . .
O2 O 0.6705(5) 1.0365(3) 0.22728(14) 0.0831(9) Uani 1 1 d . . . . .
N1 N 0.8414(5) 0.8138(3) 0.30751(15) 0.0537(8) Uani 1 1 d . . . . .
C8 C 0.2064(6) 0.8556(3) 0.52033(17) 0.0417(8) Uani 1 1 d . . . . .
C9 C 0.2128(6) 0.9542(3) 0.45151(16) 0.0408(8) Uani 1 1 d . . . . .
C5 C 0.6239(6) 0.7672(4) 0.42375(17) 0.0440(8) Uani 1 1 d . . . . .
C10 C 0.0132(6) 1.0975(3) 0.43039(16) 0.0426(8) Uani 1 1 d . . . . .
C4 C 0.4236(6) 0.9083(3) 0.40336(17) 0.0419(8) Uani 1 1 d . . . . .
C7 C 0.4089(6) 0.7202(4) 0.53786(17) 0.0483(9) Uani 1 1 d . . . . .
H2 H 0.407024 0.656045 0.582530 0.058 Uiso 1 1 calc R U . . .
C6 C 0.6155(6) 0.6772(4) 0.49043(19) 0.0504(9) Uani 1 1 d . . . . .
H1 H 0.750262 0.585999 0.504157 0.060 Uiso 1 1 calc R U . . .
C1 C 0.8378(7) 0.7158(4) 0.37365(19) 0.0541(9) Uani 1 1 d . . . . .
C3 C 0.4363(6) 1.0048(4) 0.33624(17) 0.0467(9) Uani 1 1 d . . . . .
C12 C 0.2444(7) 1.1429(4) 0.31747(17) 0.0566(9) Uani 1 1 d . . . . .
H4 H 0.253349 1.207042 0.273008 0.068 Uiso 1 1 calc R U . . .
C11 C 0.0371(6) 1.1881(4) 0.36385(18) 0.0546(9) Uani 1 1 d . . . . .
H3 H -0.090179 1.282666 0.349711 0.066 Uiso 1 1 calc R U . . .
C2 C 0.6535(7) 0.9564(4) 0.2860(2) 0.0572(9) Uani 1 1 d . . . . .
C13 C 1.0441(7) 0.7572(4) 0.25605(18) 0.0629(10) Uani 1 1 d . . . . .
H5 H 1.213618 0.700485 0.280495 0.075 Uiso 1 1 calc R U . . .
H6 H 1.092829 0.851753 0.223533 0.075 Uiso 1 1 calc R U . . .
C14 C 0.9301(7) 0.6430(4) 0.21495(18) 0.0712(11) Uani 1 1 d . . . . .
H7 H 0.859200 0.556344 0.247912 0.085 Uiso 1 1 calc R U . . .
H8 H 0.773764 0.704173 0.186352 0.085 Uiso 1 1 calc R U . . .
C15 C 1.1419(7) 0.5657(4) 0.16786(19) 0.0752(11) Uani 1 1 d . . . . .
H9 H 1.304404 0.511399 0.195868 0.090 Uiso 1 1 calc R U . . .
H10 H 1.202393 0.651914 0.132647 0.090 Uiso 1 1 calc R U . . .
C16 C 1.0332(8) 0.4415(5) 0.1307(2) 0.0818(12) Uani 1 1 d . . . . .
H11 H 0.963324 0.358509 0.165808 0.098 Uiso 1 1 calc R U . . .
H12 H 0.877039 0.497158 0.100714 0.098 Uiso 1 1 calc R U . . .
C17 C 1.2487(9) 0.3581(5) 0.0868(2) 0.1043(15) Uani 1 1 d . . . . .
H13 H 1.404694 0.303116 0.117043 0.125 Uiso 1 1 calc R U . . .
H14 H 1.318666 0.441654 0.052047 0.125 Uiso 1 1 calc R U . . .
C18 C 1.1487(13) 0.2339(7) 0.0491(3) 0.136(2) Uani 1 1 d D . . . .
H16A H 0.960733 0.275663 0.031365 0.163 Uiso 0.524(11) 1 calc R U P A 1
H15A H 1.269197 0.220950 0.008935 0.163 Uiso 0.524(11) 1 calc R U P A 1
H15B H 1.020352 0.177136 0.080504 0.163 Uiso 0.476(11) 1 calc R U P A 2
H16B H 1.039418 0.295334 0.008849 0.163 Uiso 0.476(11) 1 calc R U P A 2
C19A C 1.147(2) 0.0914(13) 0.0888(5) 0.111(4) Uani 0.524(11) 1 d D . P A 1
H17A H 1.081936 0.017811 0.062109 0.167 Uiso 0.524(11) 1 calc R U P A 1
H18A H 1.333372 0.048064 0.105663 0.167 Uiso 0.524(11) 1 calc R U P A 1
H19A H 1.024787 0.102799 0.128101 0.167 Uiso 0.524(11) 1 calc R U P A 1
C19B C 1.334(3) 0.1158(19) 0.0249(10) 0.197(10) Uani 0.476(11) 1 d D . P A 2
H18B H 1.232405 0.048461 0.002488 0.296 Uiso 0.476(11) 1 calc R U P A 2
H19B H 1.458813 0.167529 -0.008346 0.296 Uiso 0.476(11) 1 calc R U P A 2
H17B H 1.439615 0.048513 0.063805 0.296 Uiso 0.476(11) 1 calc R U P A 2


_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 C2 1.216(4) . ?
N1 C1 1.388(4) . ?
N1 C2 1.393(4) . ?
N1 C13 1.469(4) . ?
C8 C9 1.433(4) . ?
C8 C10 1.466(4) 2_576 ?
C8 C7 1.380(4) . ?
C9 C10 1.426(4) . ?
C9 C4 1.420(4) . ?
C5 C4 1.414(4) . ?
C5 C6 1.371(4) . ?
C5 C1 1.470(4) . ?
C10 C11 1.380(4) . ?
C4 C3 1.402(4) . ?
C7 H2 0.9300 . ?
C7 C6 1.391(4) . ?
C6 H1 0.9300 . ?
C3 C12 1.369(4) . ?
C3 C2 1.474(4) . ?
C12 H4 0.9300 . ?
C12 C11 1.384(4) . ?
C11 H3 0.9300 . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C13 C14 1.514(4) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C15 1.505(4) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.521(5) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C17 1.499(5) . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C18 1.509(6) . ?
C18 H16A 0.9700 . ?
C18 H15A 0.9700 . ?
C18 H15B 0.9700 . ?
C18 H16B 0.9700 . ?
C18 C19A 1.296(8) . ?
C18 C19B 1.371(10) . ?
C19A H17A 0.9600 . ?
C19A H18A 0.9600 . ?
C19A H19A 0.9600 . ?
C19B H18B 0.9600 . ?
C19B H19B 0.9600 . ?
C19B H17B 0.9600 . ?

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 C2 123.8(3) . . ?
C1 N1 C13 117.6(3) . . ?
C2 N1 C13 118.4(3) . . ?
C9 C8 C10 119.0(3) . 2_576 ?
C7 C8 C9 118.6(3) . . ?
C7 C8 C10 122.4(3) . 2_576 ?
C10 C9 C8 121.6(3) . . ?
C4 C9 C8 119.2(3) . . ?
C4 C9 C10 119.3(3) . . ?
C4 C5 C1 120.4(3) . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 C1 120.1(3) . . ?
C9 C10 C8 119.5(3) . 2_576 ?
C11 C10 C8 122.4(3) . 2_576 ?
C11 C10 C9 118.1(3) . . ?
C5 C4 C9 119.9(3) . . ?
C3 C4 C9 120.0(3) . . ?
C3 C4 C5 120.1(3) . . ?
C8 C7 H2 119.2 . . ?
C8 C7 C6 121.7(3) . . ?
C6 C7 H2 119.2 . . ?
C5 C6 C7 121.1(3) . . ?
C5 C6 H1 119.5 . . ?
C7 C6 H1 119.5 . . ?
O1 C1 N1 120.0(3) . . ?
O1 C1 C5 122.4(3) . . ?
N1 C1 C5 117.7(3) . . ?
C4 C3 C2 120.0(3) . . ?
C12 C3 C4 119.6(3) . . ?
C12 C3 C2 120.4(3) . . ?
C3 C12 H4 119.6 . . ?
C3 C12 C11 120.8(3) . . ?
C11 C12 H4 119.6 . . ?
C10 C11 C12 122.1(3) . . ?
C10 C11 H3 118.9 . . ?
C12 C11 H3 118.9 . . ?
O2 C2 N1 120.0(3) . . ?
O2 C2 C3 121.9(3) . . ?
N1 C2 C3 118.0(3) . . ?
N1 C13 H5 109.2 . . ?
N1 C13 H6 109.2 . . ?
N1 C13 C14 112.1(3) . . ?
H5 C13 H6 107.9 . . ?
C14 C13 H5 109.2 . . ?
C14 C13 H6 109.2 . . ?
C13 C14 H7 108.7 . . ?
C13 C14 H8 108.7 . . ?
H7 C14 H8 107.6 . . ?
C15 C14 C13 114.0(3) . . ?
C15 C14 H7 108.7 . . ?
C15 C14 H8 108.7 . . ?
C14 C15 H9 108.8 . . ?
C14 C15 H10 108.8 . . ?
C14 C15 C16 114.0(3) . . ?
H9 C15 H10 107.7 . . ?
C16 C15 H9 108.8 . . ?
C16 C15 H10 108.8 . . ?
C15 C16 H11 108.8 . . ?
C15 C16 H12 108.8 . . ?
H11 C16 H12 107.7 . . ?
C17 C16 C15 113.9(3) . . ?
C17 C16 H11 108.8 . . ?
C17 C16 H12 108.8 . . ?
C16 C17 H13 108.4 . . ?
C16 C17 H14 108.4 . . ?
C16 C17 C18 115.5(4) . . ?
H13 C17 H14 107.5 . . ?
C18 C17 H13 108.4 . . ?
C18 C17 H14 108.4 . . ?
C17 C18 H16A 108.9 . . ?
C17 C18 H15A 108.9 . . ?
C17 C18 H15B 107.0 . . ?
C17 C18 H16B 107.0 . . ?
H16A C18 H15A 107.8 . . ?
H15B C18 H16B 106.7 . . ?
C19A C18 C17 113.2(7) . . ?
C19A C18 H16A 108.9 . . ?
C19A C18 H15A 108.9 . . ?
C19B C18 C17 121.3(7) . . ?
C19B C18 H15B 107.0 . . ?
C19B C18 H16B 107.0 . . ?
C18 C19A H17A 109.5 . . ?
C18 C19A H18A 109.5 . . ?
C18 C19A H19A 109.5 . . ?
H17A C19A H18A 109.5 . . ?
H17A C19A H19A 109.5 . . ?
H18A C19A H19A 109.5 . . ?
C18 C19B H18B 109.5 . . ?
C18 C19B H19B 109.5 . . ?
C18 C19B H17B 109.5 . . ?
H18B C19B H19B 109.5 . . ?
H18B C19B H17B 109.5 . . ?
H19B C19B H17B 109.5 . . ?

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
N1 C13 C14 C15 -173.0(3) . . . . ?
C8 C9 C10 C8 -0.8(4) . . . 2_576 ?
C8 C9 C10 C11 178.5(2) . . . . ?
C8 C9 C4 C5 -0.2(4) . . . . ?
C8 C9 C4 C3 -178.9(2) . . . . ?
C8 C10 C11 C12 -179.8(3) 2_576 . . . ?
C8 C7 C6 C5 -0.8(4) . . . . ?
C9 C8 C7 C6 -0.5(4) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C9 C4 C3 C12 -0.1(4) . . . . ?
C9 C4 C3 C2 -179.4(2) . . . . ?
C5 C4 C3 C12 -178.8(3) . . . . ?
C5 C4 C3 C2 1.9(4) . . . . ?
C10 C8 C9 C10 0.8(4) 2_576 . . . ?
C10 C8 C9 C4 -179.4(2) 2_576 . . . ?
C10 C8 C7 C6 179.9(2) 2_576 . . . ?
C10 C9 C4 C5 179.6(2) . . . . ?
C10 C9 C4 C3 0.9(4) . . . . ?
C4 C9 C10 C8 179.4(2) . . . 2_576 ?
C4 C9 C10 C11 -1.2(4) . . . . ?
C4 C5 C6 C7 1.6(4) . . . . ?
C4 C5 C1 O1 -176.9(3) . . . . ?
C4 C5 C1 N1 2.5(4) . . . . ?
C4 C3 C12 C11 -0.3(5) . . . . ?
C4 C3 C2 O2 179.7(3) . . . . ?
C4 C3 C2 N1 0.1(4) . . . . ?
C7 C8 C9 C10 -178.8(2) . . . . ?
C7 C8 C9 C4 0.9(4) . . . . ?
C6 C5 C4 C9 -1.1(4) . . . . ?
C6 C5 C4 C3 177.6(2) . . . . ?
C6 C5 C1 O1 2.3(4) . . . . ?
C6 C5 C1 N1 -178.3(2) . . . . ?
C1 N1 C2 O2 179.6(3) . . . . ?
C1 N1 C2 C3 -0.8(4) . . . . ?
C1 N1 C13 C14 86.9(3) . . . . ?
C1 C5 C4 C9 178.1(2) . . . . ?
C1 C5 C4 C3 -3.1(4) . . . . ?
C1 C5 C6 C7 -177.6(2) . . . . ?
C3 C12 C11 C10 -0.2(5) . . . . ?
C12 C3 C2 O2 0.4(5) . . . . ?
C12 C3 C2 N1 -179.2(3) . . . . ?
C2 N1 C1 O1 178.9(3) . . . . ?
C2 N1 C1 C5 -0.5(4) . . . . ?
C2 N1 C13 C14 -89.3(3) . . . . ?
C2 C3 C12 C11 179.1(3) . . . . ?
C13 N1 C1 O1 3.0(4) . . . . ?
C13 N1 C1 C5 -176.4(2) . . . . ?
C13 N1 C2 O2 -4.4(4) . . . . ?
C13 N1 C2 C3 175.2(2) . . . . ?
C13 C14 C15 C16 175.8(3) . . . . ?
C14 C15 C16 C17 -176.9(3) . . . . ?
C15 C16 C17 C18 -180.0(4) . . . . ?
C16 C17 C18 C19A -81.7(8) . . . . ?
C16 C17 C18 C19B -160.4(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_PDI_C5_3_84GPa
_database_code_depnum_ccdc_archive 'CCDC 2493901'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_PDI_C5_3_84GPa      
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        25% Check 
RESPONSE: Due to the overall poor diffraction quality
of the needle-shaped crystal and low symmetry.
;
_vrf_PLAT027_PDI_C5_3_84GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      15.00 Degree
RESPONSE: Due to the specificity of the applied measuring technique and use 
of a diamond-anvil cell limiting the access of the X-ray radiation to the 
measured sample. A full set of data was collected.
;
_vrf_PLAT029_PDI_C5_3_84GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.308 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C5_3_84GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.22 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C5_3_84GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.09667 Ang.  
RESPONSE: The data come from high-pressure experiment, and part of the 
reflection can not be collected, affecting the bond precision.
;
_vrf_RINTA01_PDI_C5_3_84GPa      
;
PROBLEM: The value of Rint is greater than 0.18
            Rint given   0.221
RESPONSE:  The investigated needle-shaped single crystal was poorly 
diffractive and has low symmetry. 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 high-pressure were unsuccessful.
;
_vrf_PLAT020_PDI_C5_3_84GPa      
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.221 Report  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle. The investigated needle-shaped single crystal was poorly 
diffractive and has low symmetry. 
;
_vrf_PLAT410_PDI_C5_3_84GPa      
;
PROBLEM: Short Intra H...H Contact  H2       ..H3       .       1.82 Ang.  
                                                      x,y,z  =      1_555 Check 
RESPONSE: These data come from high-pressure studies, and the short distance 
is likely a result of poor data quality.
;
_vrf_PLAT411_PDI_C5_3_84GPa      
;
PROBLEM:Short Inter H...H Contact  H1       ..H1       .       1.97 Ang.  
                                               -2-x,-1-y,-z  =      2_345 Check 
RESPONSE: These data come from high-pressure studies, and the short distance 
is likely a result of poor data quality.
;
_vrf_PLAT413_PDI_C5_3_84GPa      
;
PROBLEM: Short Inter XH3 .. XHn     H14      ..H14      .       1.93 Ang.  
                                              1-x,-2-y,-1-z  =      2_634 Check 
RESPONSE: These data come from high-pressure studies, and the short distance 
is likely a result of poor data quality.
;
_vrf_PLAT910_PDI_C5_3_84GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note  
RESPONSE:The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT911_PDI_C5_3_84GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        447 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-02-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C5
_chemical_name_systematic        N,N-Dipentyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C34 H30 N2 O4'
_chemical_formula_sum            'C34 H30 N2 O4'
_chemical_formula_weight         530.60
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.639(3)
_cell_length_b                   8.536(7)
_cell_length_c                   17.49(3)
_cell_angle_alpha                87.48(16)
_cell_angle_beta                 76.36(15)
_cell_angle_gamma                101.09(7)
_cell_volume                     515.8(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    377
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.662
_cell_measurement_theta_min      4.889
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.112
_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            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2206
_diffrn_reflns_av_unetI/netI     0.3177
_diffrn_reflns_Laue_measured_fraction_full 0.308
_diffrn_reflns_Laue_measured_fraction_max 0.191
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1824
_diffrn_reflns_point_group_measured_fraction_full 0.308
_diffrn_reflns_point_group_measured_fraction_max 0.191
_diffrn_reflns_theta_full        15.000
_diffrn_reflns_theta_max         25.662
_diffrn_reflns_theta_min         4.889
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.308
_diffrn_measured_fraction_theta_max 0.191
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 3.84(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                96
_reflns_number_total             377
_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    ?
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         377
_refine_ls_number_restraints     291
_refine_ls_R_factor_all          0.3610
_refine_ls_R_factor_gt           0.1383
_refine_ls_restrained_S_all      0.764
_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)+17.7803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.3363
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C1
 1.3 with sigma of 0.02
 C5-C1 \\sim C5-C4 \\sim C3-C4 \\sim C3-C2 \\sim C9-C4 \\sim C9-C8 \\sim C7-C8
\\sim C5-C6 \\sim C7-C6 \\sim C10-
 C8 \\sim C10-C11 \\sim C12-C11
 with sigma of 0.02
 O2-C2 \\sim O1-C1
 with sigma of 0.02
 C12-C11 \\sim C10-C11 \\sim C10-C8 \\sim C7-C8 \\sim C7-C6 \\sim C5-C6 \\sim
C5-C4 \\sim C9-C4 \\sim C9-C8 ~
 C5-C1 \\sim C3-C2 \\sim C3-C4
 with sigma of 0.02
 N1-C1 \\sim N1-C2
 with sigma of 0.02
 C1-C2 \\sim C3-C5
 with sigma of 0.02
 C14-C13 \\sim C15-C14 \\sim C16-C15 \\sim C17-C16
 with sigma of 0.02
 C9-C7 \\sim C6-C4 \\sim C5-C3 \\sim C1-C2
 with sigma of 0.02
3. Rigid bond restraints
 C14, C13, N1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C17, C16, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C2 \\sim N1 \\sim C1 \\sim C3 \\sim C5: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
Uanis(C4) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C10) \\sim
Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(O2) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(O1) \\sim
Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C4) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C5) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C2, C3, C4, C9, C8, C10, C11, C12, C7, C6, C5, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C17, C16, C15, C14, C13
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Secondary CH2 refined with riding coordinates:
 C13(H5,H6), C14(H7,H8), C15(H9,H10), C16(H11,H12)
6.b Aromatic/amide H refined with riding coordinates:
 C6(H1), C7(H2), C11(H3), C12(H4)
6.c Fitted hexagon refined as free rotating group:
 C4(C5,C6,C7,C8,C9)
6.d Idealised Me refined as rotating group:
 C17(H13,H14,H15)
;
_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
C3 C 0.116(15) -0.096(6) -0.212(4) 0.056(16) Uani 1 1 d D U . . .
C13 C -0.237(18) -0.401(7) -0.335(11) 0.07(3) Uani 1 1 d D U . . .
H5 H -0.487838 -0.396770 -0.344439 0.078 Uiso 1 1 calc R U . . .
H6 H -0.039877 -0.343506 -0.380449 0.078 Uiso 1 1 calc R U . . .
C14 C -0.20(2) -0.578(8) -0.327(8) 0.07(3) Uani 1 1 d D U . . .
H7 H -0.446808 -0.647973 -0.304586 0.083 Uiso 1 1 calc R U . . .
H8 H -0.027922 -0.590702 -0.292215 0.083 Uiso 1 1 calc R U . . .
N1 N -0.193(13) -0.316(6) -0.258(5) 0.061(17) Uani 1 1 d D U . . .
C15 C -0.019(19) -0.617(8) -0.412(8) 0.06(3) Uani 1 1 d D U . . .
H9 H -0.188061 -0.602151 -0.445437 0.077 Uiso 1 1 calc R U . . .
H10 H 0.229511 -0.544947 -0.433126 0.077 Uiso 1 1 calc R U . . .
C2 C 0.065(17) -0.180(6) -0.276(4) 0.046(14) Uani 1 1 d D U . . .
C1 C -0.427(14) -0.384(6) -0.191(4) 0.042(14) Uani 1 1 d D U . . .
C16 C 0.03(2) -0.793(8) -0.409(9) 0.07(3) Uani 1 1 d D U . . .
H11 H -0.216798 -0.865866 -0.394507 0.079 Uiso 1 1 calc R U . . .
H12 H 0.174746 -0.811753 -0.369978 0.079 Uiso 1 1 calc R U . . .
O2 O 0.262(13) -0.113(5) -0.344(6) 0.09(3) Uani 1 1 d D U . . .
O1 O -0.705(12) -0.507(6) -0.175(8) 0.08(3) Uani 1 1 d D U . . .
C17 C 0.26(2) -0.819(8) -0.493(8) 0.07(4) Uani 1 1 d D U . . .
H13 H 0.089256 -0.836312 -0.526688 0.106 Uiso 1 1 calc R U . . .
H14 H 0.376648 -0.910178 -0.489350 0.106 Uiso 1 1 calc R U . . .
H15 H 0.461349 -0.725267 -0.513525 0.106 Uiso 1 1 calc R U . . .
C4 C -0.103(10) -0.156(4) -0.136(4) 0.031(10) Uani 1 1 d DG U . . .
C5 C -0.378(11) -0.297(4) -0.127(4) 0.039(12) Uani 1 1 d DG U . . .
C6 C -0.596(10) -0.363(3) -0.052(4) 0.055(17) Uani 1 1 d DG . . . .
H1 H -0.779870 -0.457176 -0.045609 0.066 Uiso 1 1 calc R U . . .
C7 C -0.537(10) -0.286(4) 0.014(4) 0.044(14) Uani 1 1 d DG . . . .
H2 H -0.682660 -0.329820 0.064634 0.053 Uiso 1 1 calc R U . . .
C8 C -0.262(10) -0.145(4) 0.006(4) 0.035(11) Uani 1 1 d DG U . . .
C9 C -0.044(9) -0.080(3) -0.069(4) 0.047(13) Uani 1 1 d DG U . . .
C10 C -0.220(15) -0.062(6) 0.071(4) 0.035(13) Uani 1 1 d D U . . .
C11 C -0.42(2) -0.134(10) 0.146(5) 0.08(3) Uani 1 1 d D . . . .
H3 H -0.583829 -0.235020 0.150918 0.092 Uiso 1 1 calc R U . . .
C12 C -0.386(17) -0.059(7) 0.213(7) 0.053(19) Uani 1 1 d D . . . .
H4 H -0.539899 -0.107415 0.262061 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
C3 C2 1.39(2) . ?
C3 C4 1.40(2) . ?
C3 C12 1.48(7) 2 ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C13 C14 1.55(8) . ?
C13 N1 1.59(16) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C15 1.55(8) . ?
N1 C2 1.32(3) . ?
N1 C1 1.31(2) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.55(8) . ?
C2 O2 1.28(6) . ?
C1 O1 1.28(5) . ?
C1 C5 1.39(2) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C17 1.55(8) . ?
C17 H13 0.9600 . ?
C17 H14 0.9600 . ?
C17 H15 0.9600 . ?
C4 C5 1.3900 . ?
C4 C9 1.3900 . ?
C5 C6 1.3900 . ?
C6 H1 0.9300 . ?
C6 C7 1.3900 . ?
C7 H2 0.9300 . ?
C7 C8 1.3900 . ?
C8 C9 1.3900 . ?
C8 C10 1.39(2) . ?
C9 C10 1.39(5) 2 ?
C10 C11 1.39(2) . ?
C11 H3 0.9300 . ?
C11 C12 1.39(2) . ?
C12 H4 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
C2 C3 C4 120(4) . . ?
C2 C3 C12 127(6) . 2 ?
C4 C3 C12 113(6) . 2 ?
H5 C13 H6 108.1 . . ?
C14 C13 H5 109.3 . . ?
C14 C13 H6 109.8 . . ?
C14 C13 N1 111(10) . . ?
N1 C13 H5 109.5 . . ?
N1 C13 H6 109.6 . . ?
C13 C14 H7 110.9 . . ?
C13 C14 H8 110.6 . . ?
C13 C14 C15 105(10) . . ?
H7 C14 H8 108.8 . . ?
C15 C14 H7 110.9 . . ?
C15 C14 H8 110.4 . . ?
C2 N1 C13 111(6) . . ?
C1 N1 C13 117(5) . . ?
C1 N1 C2 132(5) . . ?
C14 C15 H9 109.6 . . ?
C14 C15 H10 110.1 . . ?
H9 C15 H10 108.3 . . ?
C16 C15 C14 109(10) . . ?
C16 C15 H9 109.8 . . ?
C16 C15 H10 109.8 . . ?
N1 C2 C3 115(4) . . ?
O2 C2 C3 116(6) . . ?
O2 C2 N1 129(5) . . ?
N1 C1 C5 113(4) . . ?
O1 C1 N1 131(7) . . ?
O1 C1 C5 116(6) . . ?
C15 C16 H11 110.3 . . ?
C15 C16 H12 110.2 . . ?
C15 C16 C17 107(10) . . ?
H11 C16 H12 108.6 . . ?
C17 C16 H11 110.3 . . ?
C17 C16 H12 110.3 . . ?
C16 C17 H13 109.5 . . ?
C16 C17 H14 109.5 . . ?
C16 C17 H15 109.4 . . ?
H13 C17 H14 109.5 . . ?
H13 C17 H15 109.5 . . ?
H14 C17 H15 109.5 . . ?
C5 C4 C3 118(2) . . ?
C5 C4 C9 120.0 . . ?
C9 C4 C3 122(2) . . ?
C4 C5 C1 122(3) . . ?
C6 C5 C1 118(3) . . ?
C6 C5 C4 120.0 . . ?
C5 C6 H1 120.0 . . ?
C5 C6 C7 120.0 . . ?
C7 C6 H1 120.0 . . ?
C6 C7 H2 120.0 . . ?
C6 C7 C8 120.0 . . ?
C8 C7 H2 120.0 . . ?
C7 C8 C10 120(3) . . ?
C9 C8 C7 120.0 . . ?
C9 C8 C10 120(3) . . ?
C8 C9 C4 120.0 . . ?
C10 C9 C4 125(5) 2 . ?
C10 C9 C8 115(5) 2 . ?
C9 C10 C8 125(6) 2 . ?
C9 C10 C11 115(7) 2 . ?
C11 C10 C8 119(6) . . ?
C10 C11 H3 119.5 . . ?
C12 C11 C10 121(8) . . ?
C12 C11 H3 119.5 . . ?
C3 C12 H4 118.3 2 . ?
C11 C12 C3 123(9) . 2 ?
C11 C12 H4 118.4 . . ?

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
C3 C4 C5 C1 3(5) . . . . ?
C3 C4 C5 C6 179(5) . . . . ?
C3 C4 C9 C8 -179(5) . . . . ?
C3 C4 C9 C10 2(5) . . . 2 ?
C13 C14 C15 C16 180(5) . . . . ?
C13 N1 C2 C3 178(6) . . . . ?
C13 N1 C2 O2 1(10) . . . . ?
C13 N1 C1 O1 -3(10) . . . . ?
C13 N1 C1 C5 -177(5) . . . . ?
C14 C13 N1 C2 129(7) . . . . ?
C14 C13 N1 C1 -56(8) . . . . ?
C14 C15 C16 C17 -172(6) . . . . ?
N1 C13 C14 C15 -149(7) . . . . ?
N1 C1 C5 C4 -1(6) . . . . ?
N1 C1 C5 C6 -176(4) . . . . ?
C2 C3 C4 C5 -2(8) . . . . ?
C2 C3 C4 C9 176(4) . . . . ?
C2 N1 C1 O1 171(6) . . . . ?
C2 N1 C1 C5 -3(9) . . . . ?
C1 N1 C2 C3 4(10) . . . . ?
C1 N1 C2 O2 -173(8) . . . . ?
C1 C5 C6 C7 176(4) . . . . ?
O1 C1 C5 C4 -176(4) . . . . ?
O1 C1 C5 C6 8(6) . . . . ?
C4 C3 C2 N1 -1(9) . . . . ?
C4 C3 C2 O2 177(6) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C4 C9 C8 0.0 . . . . ?
C5 C4 C9 C10 -180(4) . . . 2 ?
C5 C6 C7 C8 0.0 . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C6 C7 C8 C10 176(4) . . . . ?
C7 C8 C9 C4 0.0 . . . . ?
C7 C8 C9 C10 180(4) . . . 2 ?
C7 C8 C10 C9 180(6) . . . 2 ?
C7 C8 C10 C11 8(8) . . . . ?
C8 C10 C11 C12 179(5) . . . . ?
C9 C4 C5 C1 -175(4) . . . . ?
C9 C4 C5 C6 0.0 . . . . ?
C9 C8 C10 C9 -4(6) . . . 2 ?
C9 C8 C10 C11 -176(6) . . . . ?
C9 C10 C11 C12 7(12) 2 . . . ?
C10 C8 C9 C4 -176(4) . . . . ?
C10 C8 C9 C10 4(6) . . . 2 ?
C10 C11 C12 C3 -4(13) . . . 2 ?
C12 C3 C2 N1 179(6) 2 . . . ?
C12 C3 C2 O2 -3(10) 2 . . . ?
C12 C3 C4 C5 178(3) 2 . . . ?
C12 C3 C4 C9 -4(6) 2 . . . ?

_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_PDI_C5_0_98GPa
_database_code_depnum_ccdc_archive 'CCDC 2493896'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PDI_C5_0_98GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      15.00 Degree
RESPONSE: Due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell limiting the access of 
the X-ray radiation to the measured sample. A full set of data was collected.
;
_vrf_PLAT029_PDI_C5_0_98GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.351 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C5_0_98GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.87 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C5_0_98GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.04 Ang. 
RESPONSE: The data come from high-pressure experiment, and part of the 
reflection can not be collected, affecting the bond precision.
;
_vrf_PLAT911_PDI_C5_0_98GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        573 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-02-25

_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C5
_chemical_name_systematic        N,N-Dipentyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C34 H30 N2 O4'
_chemical_formula_sum            'C34 H30 N2 O4'
_chemical_formula_weight         530.60
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.5635(9)
_cell_length_b                   8.3918(9)
_cell_length_c                   15.696(8)
_cell_angle_alpha                85.64(3)
_cell_angle_beta                 83.32(3)
_cell_angle_gamma                85.608(13)
_cell_volume                     593.9(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    563
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.1050
_cell_measurement_theta_min      4.5000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.451
_exptl_absorpt_correction_T_min  0.349
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.79a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 11 1 0.1114
0 0 -22 0.0213
0 0 22 0.0213
-6 -2 -4 0.0596
-6 -4 -5 0.0663
1 -11 -1 0.1283
6 4 5 0.0669
6 2 4 0.0551

_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.042
_exptl_oxdiff_absorpt_process_details 
;
Gaussian integration over a grid
of 16 x 16 x 16 points =  4096 total grid points
  Based upon method of Burnham (1966)

 Data corrected for diamond-anvil cell absorption
 Note that exptl_absorpt_correction_tmin and _tmax
 the total correction factors applied to the intensities
 The individual factors are: 
         range of dac transmission factors (min-max)      0.401     0.453
         range of gasket transmission (min-max)           0.841     1.000
         range of P media transmission (min-max)          1.000     1.000

 thickness of diamond anvil 1: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 1:  0.000 mm, mu =  0.0000 mm-1

 thickness of diamond anvil 2: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 2:  0.000 mm, mu =  0.0000 mm-1

    Gasket shadowing corrections were made based upon
    Gasket thickness = 200.0 microns, radius = 185.0 microns
    Gasket absorption coeff =        21.00 mm-1
    REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF 
 FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00

    Non-absorbing pressure medium
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_Laue_measured_fraction_full 0.351
_diffrn_reflns_Laue_measured_fraction_max 0.206
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3430
_diffrn_reflns_point_group_measured_fraction_full 0.351
_diffrn_reflns_point_group_measured_fraction_max 0.206
_diffrn_reflns_theta_full        15.000
_diffrn_reflns_theta_max         26.787
_diffrn_reflns_theta_min         4.552
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.351
_diffrn_measured_fraction_theta_max 0.206
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.25  49.00   0.75    7.50    --    0.16 -53.00  17.00   83
  2  ω    -13.25  49.00   0.75    7.50    --    0.16 -53.00-162.00   83
  3  ω    -22.25  40.00   0.75   20.00    --  -30.73 -26.00   7.00   83
  4  ω    -66.25  -4.00   0.75   20.00    --  -30.73  97.00 -35.00   83
  5  ω    -35.25  27.00   0.75   20.00    --  -30.73  13.00 176.00   83
  6  ω     13.75  40.00   0.75   20.00    --  -30.73-114.00-135.00   35
  7  ω    -54.25   8.00   0.75   20.00    --  -30.73  67.00 157.00   83
  8  ω    -13.25  22.00   0.75   20.00    --  -30.73 -53.00-162.00   47
  9  ω    -13.25  22.00   0.75   20.00    --  -30.73 -53.00  17.00   47
 10  ω      5.00  29.00   0.75   20.00    --  -30.73 -97.00  35.00   32
 11  ω    -43.25 -11.00   0.75   20.00    --  -30.73  19.00   0.00   43
 12  ω     38.00  89.00   0.75   20.00    --   31.04-135.00-123.00   68
 13  ω     21.00  56.25   0.75   20.00    --   31.04 -77.00-150.00   47
 14  ω    -39.25 -13.00   0.75   20.00    --   31.04 114.00 -45.00   35
 15  ω    -14.25  36.00   0.75   20.00    --   31.04 -13.00   3.00   67
 16  ω     21.00  56.25   0.75   20.00    --   31.04 -77.00  30.00   47
 17  ω    -21.25  14.00   0.75   20.00    --   31.04  53.00 -17.00   47
 18  ω    -30.00   0.00   0.75   20.00    --   31.04   0.00-150.00   40
 19  ω    -70.00 -13.75   0.75    7.50    --    0.16 114.00 135.00   75
 20  ω    -53.00 -26.00   0.75    7.50    --    0.16  37.00   0.00   36
 21  ω    -53.00 -26.00   0.75   20.00    --  -30.73  37.00   0.00   36
 22  ω    -18.25  44.00   0.75   20.00    --  -30.73 -39.00-167.00   83
 23  ω     -9.25  44.00   0.75   20.00    --   31.04 -19.00-180.00   71
 24  ω    -21.25  14.00   0.75   20.00    --   31.04  53.00 162.00   47
 25  ω     -5.00  19.00   0.75   20.00    --   31.04  57.00 -30.00   32
 26  ω     25.00  76.00   0.75   20.00    --   31.04-114.00  45.00   68
 27  ω    -31.00  23.00   0.75   20.00    --   31.04  26.00  -7.00   72
 28  ω    -39.25 -13.00   0.75   20.00    --   31.04 114.00 135.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          
;
 Data were collected at room temperature and pressure of 0.98(2) GPa
 Pressure was determined by monitoring the shift of 
 the ruby R1-fluorescence line.
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                256
_reflns_number_total             523
_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 1.171.40.79a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.79a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.79a (Rigaku OD, 2020)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         523
_refine_ls_number_restraints     291
_refine_ls_R_factor_all          0.1956
_refine_ls_R_factor_gt           0.1037
_refine_ls_restrained_S_all      0.812
_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)+11.0969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.2416
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H3(0.044) H4(0.036) H1(0.026) H2(0.03) H6(0.05) H5(0.05)
 H8(0.049) H7(0.049) H10(0.048) H9(0.048) H12(0.055) H11(0.055) H13(0.078)
 H14(0.078) H15(0.078)
 Fixed X: H3(0.005457) H4(-0.396063) H1(-0.734391) H2(-0.33265) H6(-1.230951)
 H5(-1.333667) H8(-0.877835) H7(-0.913554) H10(-1.340336) H9(-1.391979) H12(-
 0.953108) H11(-0.984644) H13(-1.447346) H14(-1.209183) H15(-1.423149)
 Fixed Y: H3(-0.224242) H4(-0.134855) H1(0.407063) H2(0.320654) H6(0.250771)
 H5(0.378306) H8(0.410282) H7(0.526275) H10(0.505222) H9(0.615116) H12(0.65638)
 H11(0.761733) H13(0.869146) H14(0.898795) H15(0.761036)
 Fixed Z: H3(0.18859) H4(0.283276) H1(-0.014693) H2(-0.111651) H6(0.34407)
 H5(0.273) H8(0.377299) H7(0.295523) H10(0.441317) H9(0.358234) H12(0.466898)
 H11(0.381164) H13(0.438557) H14(0.498921) H15(0.523741)
;
_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 -1.047(3) 0.4494(13) 0.127(3) 0.037(8) Uani 1 1 d D U . . .
O2 O -0.825(5) 0.0638(18) 0.338(3) 0.053(8) Uani 1 1 d D U . . .
N1 N -0.938(4) 0.2554(17) 0.233(2) 0.028(7) Uani 1 1 d D U . . .
C8 C -0.184(4) 0.1354(17) -0.027(3) 0.026(8) Uani 1 1 d D . . . .
C9 C -0.232(4) 0.0637(18) 0.058(2) 0.025(8) Uani 1 1 d D . . . .
C10 C -0.053(5) -0.076(2) 0.083(3) 0.031(11) Uani 1 1 d D . . . .
C11 C -0.118(5) -0.139(2) 0.170(3) 0.037(11) Uani 1 1 d D . . . .
H3 H 0.005457 -0.224242 0.188590 0.044 Uiso 1 1 calc R U . . .
C12 C -0.356(4) -0.0832(17) 0.229(3) 0.030(11) Uani 1 1 d D . . . .
H4 H -0.396063 -0.134855 0.283276 0.036 Uiso 1 1 calc R U . . .
C3 C -0.532(4) 0.0558(19) 0.2019(19) 0.029(8) Uani 1 1 d D . . . .
C4 C -0.470(4) 0.1232(18) 0.1162(19) 0.027(8) Uani 1 1 d D . . . .
C5 C -0.657(5) 0.2605(19) 0.090(2) 0.029(7) Uani 1 1 d D . . . .
C6 C -0.604(4) 0.324(2) 0.004(2) 0.022(7) Uani 1 1 d D . . . .
H1 H -0.734391 0.407063 -0.014693 0.026 Uiso 1 1 calc R U . . .
C7 C -0.367(3) 0.2711(17) -0.057(3) 0.025(6) Uani 1 1 d D U . . .
H2 H -0.332650 0.320654 -0.111651 0.030 Uiso 1 1 calc R U . . .
C1 C -0.890(4) 0.327(2) 0.148(2) 0.031(7) Uani 1 1 d D . . . .
C2 C -0.765(5) 0.116(3) 0.262(2) 0.029(7) Uani 1 1 d D . . . .
C13 C -1.164(4) 0.332(2) 0.300(2) 0.042(7) Uani 1 1 d D U . . .
H6 H -1.230951 0.250771 0.344070 0.050 Uiso 1 1 calc R U . . .
H5 H -1.333667 0.378306 0.273000 0.050 Uiso 1 1 calc R U . . .
C14 C -1.020(4) 0.461(2) 0.341(3) 0.041(6) Uani 1 1 d D U . . .
H8 H -0.877835 0.410282 0.377299 0.049 Uiso 1 1 calc R U . . .
H7 H -0.913554 0.526275 0.295523 0.049 Uiso 1 1 calc R U . . .
C15 C -1.243(4) 0.569(2) 0.394(3) 0.040(6) Uani 1 1 d D U . . .
H10 H -1.340336 0.505222 0.441317 0.048 Uiso 1 1 calc R U . . .
H9 H -1.391979 0.615116 0.358234 0.048 Uiso 1 1 calc R U . . .
C16 C -1.094(5) 0.703(2) 0.429(4) 0.046(7) Uani 1 1 d D U . . .
H12 H -0.953108 0.656380 0.466898 0.055 Uiso 1 1 calc R U . . .
H11 H -0.984644 0.761733 0.381164 0.055 Uiso 1 1 calc R U . . .
C17 C -1.314(5) 0.819(3) 0.477(4) 0.052(10) Uani 1 1 d D U . . .
H13 H -1.447346 0.869146 0.438557 0.078 Uiso 1 1 calc R U . . .
H14 H -1.209183 0.898795 0.498921 0.078 Uiso 1 1 calc R U . . .
H15 H -1.423149 0.761036 0.523741 0.078 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 1.25(3) . ?
O2 C2 1.25(3) . ?
N1 C1 1.43(3) . ?
N1 C2 1.43(3) . ?
N1 C13 1.52(2) . ?
C8 C9 1.423(19) . ?
C8 C10 1.40(5) 2 ?
C8 C7 1.438(15) . ?
C9 C10 1.431(16) . ?
C9 C4 1.424(17) . ?
C10 C11 1.424(19) . ?
C11 H3 0.9300 . ?
C11 C12 1.424(19) . ?
C12 H4 0.9300 . ?
C12 C3 1.430(16) . ?
C3 C4 1.424(18) . ?
C3 C2 1.424(18) . ?
C4 C5 1.441(16) . ?
C5 C6 1.421(19) . ?
C5 C1 1.423(19) . ?
C6 H1 0.9300 . ?
C6 C7 1.422(18) . ?
C7 H2 0.9300 . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.525(17) . ?
C14 H8 0.9700 . ?
C14 H7 0.9700 . ?
C14 C15 1.523(19) . ?
C15 H10 0.9700 . ?
C15 H9 0.9700 . ?
C15 C16 1.525(17) . ?
C16 H12 0.9700 . ?
C16 H11 0.9700 . ?
C16 C17 1.52(2) . ?
C17 H13 0.9600 . ?
C17 H14 0.9600 . ?
C17 H15 0.9600 . ?

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 C2 122(2) . . ?
C1 N1 C13 120.9(17) . . ?
C2 N1 C13 117(2) . . ?
C9 C8 C7 122(2) . . ?
C10 C8 C9 119.0(19) 2 . ?
C10 C8 C7 119(3) 2 . ?
C8 C9 C10 120(2) . . ?
C8 C9 C4 120.1(17) . . ?
C4 C9 C10 120(3) . . ?
C8 C10 C9 121(3) 2 . ?
C8 C10 C11 123(2) 2 . ?
C11 C10 C9 116(3) . . ?
C10 C11 H3 117.2 . . ?
C12 C11 C10 126(2) . . ?
C12 C11 H3 117.2 . . ?
C11 C12 H4 121.5 . . ?
C11 C12 C3 117(3) . . ?
C3 C12 H4 121.5 . . ?
C4 C3 C12 119(2) . . ?
C4 C3 C2 123.6(18) . . ?
C2 C3 C12 118(2) . . ?
C9 C4 C5 120(2) . . ?
C3 C4 C9 122.9(17) . . ?
C3 C4 C5 117(2) . . ?
C6 C5 C4 117(2) . . ?
C6 C5 C1 121(2) . . ?
C1 C5 C4 121(2) . . ?
C5 C6 H1 117.6 . . ?
C5 C6 C7 124.8(19) . . ?
C7 C6 H1 117.6 . . ?
C8 C7 H2 122.2 . . ?
C6 C7 C8 116(2) . . ?
C6 C7 H2 122.2 . . ?
O1 C1 N1 119(3) . . ?
O1 C1 C5 122(3) . . ?
C5 C1 N1 119(2) . . ?
O2 C2 N1 117(3) . . ?
O2 C2 C3 126(2) . . ?
C3 C2 N1 117(2) . . ?
N1 C13 H6 109.9 . . ?
N1 C13 H5 109.9 . . ?
N1 C13 C14 109(2) . . ?
H6 C13 H5 108.3 . . ?
C14 C13 H6 109.9 . . ?
C14 C13 H5 109.9 . . ?
C13 C14 H8 109.0 . . ?
C13 C14 H7 109.0 . . ?
H8 C14 H7 107.8 . . ?
C15 C14 C13 113.1(18) . . ?
C15 C14 H8 109.0 . . ?
C15 C14 H7 109.0 . . ?
C14 C15 H10 109.3 . . ?
C14 C15 H9 109.3 . . ?
C14 C15 C16 111.6(18) . . ?
H10 C15 H9 108.0 . . ?
C16 C15 H10 109.3 . . ?
C16 C15 H9 109.3 . . ?
C15 C16 H12 109.1 . . ?
C15 C16 H11 109.1 . . ?
H12 C16 H11 107.8 . . ?
C17 C16 C15 112.6(19) . . ?
C17 C16 H12 109.1 . . ?
C17 C16 H11 109.1 . . ?
C16 C17 H13 109.5 . . ?
C16 C17 H14 109.5 . . ?
C16 C17 H15 109.5 . . ?
H13 C17 H14 109.5 . . ?
H13 C17 H15 109.5 . . ?
H14 C17 H15 109.5 . . ?

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
N1 C13 C14 C15 167(2) . . . . ?
C8 C9 C10 C8 5(3) . . . 2 ?
C8 C9 C10 C11 -180(2) . . . . ?
C8 C9 C4 C3 179(2) . . . . ?
C8 C9 C4 C5 -3(3) . . . . ?
C8 C10 C11 C12 -179.9(19) 2 . . . ?
C9 C8 C7 C6 -2(2) . . . . ?
C9 C10 C11 C12 5(4) . . . . ?
C9 C4 C5 C6 4(3) . . . . ?
C9 C4 C5 C1 -178(2) . . . . ?
C10 C8 C9 C10 -5(3) 2 . . . ?
C10 C8 C9 C4 179.5(18) 2 . . . ?
C10 C8 C7 C6 179.8(19) 2 . . . ?
C10 C9 C4 C3 4(3) . . . . ?
C10 C9 C4 C5 -178.1(19) . . . . ?
C10 C11 C12 C3 -5(4) . . . . ?
C11 C12 C3 C4 4(3) . . . . ?
C11 C12 C3 C2 -178(2) . . . . ?
C12 C3 C4 C9 -4(3) . . . . ?
C12 C3 C4 C5 178.3(17) . . . . ?
C12 C3 C2 O2 3(4) . . . . ?
C12 C3 C2 N1 -179.9(18) . . . . ?
C3 C4 C5 C6 -178(2) . . . . ?
C3 C4 C5 C1 1(3) . . . . ?
C4 C9 C10 C8 -179.4(19) . . . 2 ?
C4 C9 C10 C11 -4(3) . . . . ?
C4 C3 C2 O2 -179(3) . . . . ?
C4 C3 C2 N1 -2(3) . . . . ?
C4 C5 C6 C7 -5(3) . . . . ?
C4 C5 C1 O1 177.3(19) . . . . ?
C4 C5 C1 N1 0(3) . . . . ?
C5 C6 C7 C8 4(3) . . . . ?
C6 C5 C1 O1 -5(4) . . . . ?
C6 C5 C1 N1 178(2) . . . . ?
C7 C8 C9 C10 177.2(17) . . . . ?
C7 C8 C9 C4 2(3) . . . . ?
C1 N1 C2 O2 -180(3) . . . . ?
C1 N1 C2 C3 3(3) . . . . ?
C1 N1 C13 C14 -84(2) . . . . ?
C1 C5 C6 C7 176.5(17) . . . . ?
C2 N1 C1 O1 -179.1(18) . . . . ?
C2 N1 C1 C5 -2(3) . . . . ?
C2 N1 C13 C14 92(2) . . . . ?
C2 C3 C4 C9 178.3(18) . . . . ?
C2 C3 C4 C5 0(3) . . . . ?
C13 N1 C1 O1 -3(3) . . . . ?
C13 N1 C1 C5 173.8(16) . . . . ?
C13 N1 C2 O2 4(3) . . . . ?
C13 N1 C2 C3 -173.3(18) . . . . ?
C13 C14 C15 C16 -176(3) . . . . ?
C14 C15 C16 C17 176(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_PDI_C7_1_24GPa
_database_code_depnum_ccdc_archive 'CCDC 2493907'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C7_1_24GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.312 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C7_1_24GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.57 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT910_PDI_C7_1_24GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         74 Note  
                1  0  0,  -1  1  0,   0  1  0,   1  1  0,  -1  2  0,   0  2  0, 
                1  2  0,   0  3  0,  -1 -2  1,   0 -2  1,   1 -2  1,  -1 -1  1, 
                0 -1  1,   1 -1  1,  -1  0  1,   0  0  1,   1  0  1,  -1  1  1, 
                0  1  1,   1  1  1,  -1  2  1,   0  2  1,   1  2  1,   0  3  1, 
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT340_PDI_C7_1_24GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01115 Ang.  
RESPONSE: These data come from high-pressure experiment and part of the 
reflections can not be collected, affecting bond precision. In addition, 
despite multiple attempts to grow better diffracting crystals, it was not 
successful.
;
_vrf_PLAT911_PDI_C7_1_24GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        1814 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-02-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        N,N-Diheptyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_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 -0.0004 0.0007 '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 -0.0003 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0008 0.0027 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.6043(3)
_cell_length_b                   8.2991(5)
_cell_length_c                   18.274(5)
_cell_angle_alpha                78.666(12)
_cell_angle_beta                 86.695(11)
_cell_angle_gamma                84.238(5)
_cell_volume                     680.7(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    625
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.9650
_cell_measurement_theta_min      5.2780
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.995
_exptl_absorpt_coefficient_mu    0.049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.312
_diffrn_reflns_Laue_measured_fraction_max 0.187
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3008
_diffrn_reflns_point_group_measured_fraction_full 0.312
_diffrn_reflns_point_group_measured_fraction_max 0.187
_diffrn_reflns_theta_full        17.166
_diffrn_reflns_theta_max         23.328
_diffrn_reflns_theta_min         5.273
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.312
_diffrn_measured_fraction_theta_max 0.187
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     20.00  94.00   0.25    1.00  57.05   0.00-134.76    --   296
  2  φ     20.00  94.00   0.25    1.00  57.05   0.00-134.76    --   296
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.4919
_diffrn_source                   synchrotron
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 1.24(2) GPa.
Pressure was determined by monitoring the shift of 
the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                694
_reflns_number_total             1114
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1114
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0855
_refine_ls_restrained_S_all      1.016
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2339
_refine_ls_wR_factor_ref         0.2650
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C2) \\sim Ueq,
Uanis(N1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O2) \\sim
Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq,
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.04
3.a Secondary CH2 refined with riding coordinates:
 C15(H9,H10), C18(H15,H16), C13(H6,H5), C17(H13,H14), C16(H11,H12), C14(H7,H8)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H3), C6(H1), C12(H4), C7(H2)
3.c Idealised Me refined as rotating group:
 C19(H17,H18,H19)
;
_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 1.0013(5) 0.4885(4) 0.6168(4) 0.082(4) Uani 1 1 d . U . . .
O2 O 0.6624(8) 0.7937(7) 0.7884(8) 0.078(6) Uani 1 1 d . U . . .
C5 C 0.6197(7) 0.6965(6) 0.5780(7) 0.044(3) Uani 1 1 d . U . . .
C9 C 0.2100(6) 0.9095(5) 0.5488(6) 0.037(3) Uani 1 1 d . U . . .
C8 C 0.2026(7) 0.8724(6) 0.4781(6) 0.039(3) Uani 1 1 d . U . . .
C1 C 0.8328(7) 0.6045(6) 0.6310(7) 0.048(3) Uani 1 1 d . U . . .
N1 N 0.8383(6) 0.6444(5) 0.7014(6) 0.048(3) Uani 1 1 d . U . . .
C11 C 0.0406(7) 1.0717(6) 0.6463(7) 0.048(3) Uani 1 1 d . U . . .
H3 H -0.085570 1.154415 0.661673 0.058 Uiso 1 1 calc R U . . .
C6 C 0.6141(7) 0.6664(6) 0.5079(7) 0.047(3) Uani 1 1 d . U . . .
H1 H 0.751360 0.587673 0.493174 0.056 Uiso 1 1 calc R U . . .
C3 C 0.4351(7) 0.8590(6) 0.6713(7) 0.046(3) Uani 1 1 d . U . . .
C4 C 0.4193(7) 0.8227(6) 0.6008(7) 0.045(3) Uani 1 1 d . U . . .
C10 C 0.0144(7) 1.0391(5) 0.5739(6) 0.043(3) Uani 1 1 d . U . . .
C15 C 1.1134(8) 0.2651(6) 0.8443(7) 0.058(3) Uani 1 1 d . U . . .
H9 H 1.287594 0.244432 0.813864 0.070 Uiso 1 1 calc R U . . .
H10 H 1.170715 0.309031 0.886193 0.070 Uiso 1 1 calc R U . . .
C12 C 0.2468(8) 0.9852(6) 0.6951(7) 0.054(3) Uani 1 1 d . U . . .
H4 H 0.260581 1.009622 0.742244 0.065 Uiso 1 1 calc R U . . .
C7 C 0.4063(7) 0.7505(5) 0.4563(6) 0.046(3) Uani 1 1 d . U . . .
H2 H 0.404187 0.725831 0.408863 0.055 Uiso 1 1 calc R U . . .
C18 C 1.0694(9) -0.1971(6) 0.9334(7) 0.063(4) Uani 1 1 d . U . . .
H15 H 0.989323 -0.221836 0.889374 0.075 Uiso 1 1 calc R U . . .
H16 H 0.910156 -0.188646 0.970033 0.075 Uiso 1 1 calc R U . . .
C13 C 1.0391(7) 0.5425(6) 0.7567(6) 0.044(3) Uani 1 1 d . U . . .
H6 H 1.087945 0.607708 0.792050 0.053 Uiso 1 1 calc R U . . .
H5 H 1.218507 0.508170 0.731162 0.053 Uiso 1 1 calc R U . . .
C17 C 1.1996(8) -0.0339(5) 0.9129(7) 0.054(3) Uani 1 1 d . U . . .
H13 H 1.371279 -0.045438 0.880396 0.065 Uiso 1 1 calc R U . . .
H14 H 1.260921 -0.003423 0.957870 0.065 Uiso 1 1 calc R U . . .
C16 C 0.9797(8) 0.1056(5) 0.8730(7) 0.058(3) Uani 1 1 d . U . . .
H11 H 0.901519 0.069196 0.831400 0.070 Uiso 1 1 calc R U . . .
H12 H 0.818183 0.124887 0.907590 0.070 Uiso 1 1 calc R U . . .
C14 C 0.8990(8) 0.3926(6) 0.7977(7) 0.056(3) Uani 1 1 d . U . . .
H7 H 0.814219 0.340909 0.761831 0.067 Uiso 1 1 calc R U . . .
H8 H 0.741648 0.427219 0.830482 0.067 Uiso 1 1 calc R U . . .
C19 C 1.2933(11) -0.3381(6) 0.9653(9) 0.104(8) Uani 1 1 d . U . . .
H17 H 1.450737 -0.347557 0.929182 0.156 Uiso 1 1 calc R U . . .
H18 H 1.201647 -0.439486 0.976938 0.156 Uiso 1 1 calc R U . . .
H19 H 1.368412 -0.316015 1.009940 0.156 Uiso 1 1 calc R U . . .
C2 C 0.6493(9) 0.7683(8) 0.7272(8) 0.044(4) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.233(5) . ?
O2 C2 1.184(18) . ?
C5 C1 1.467(12) . ?
C5 C6 1.356(16) . ?
C5 C4 1.433(6) . ?
C9 C8 1.389(14) . ?
C9 C4 1.430(11) . ?
C9 C10 1.459(6) . ?
C8 C10 1.460(12) 2_576 ?
C8 C7 1.410(6) . ?
C1 N1 1.391(15) . ?
N1 C13 1.485(11) . ?
N1 C2 1.415(7) . ?
C11 H3 0.9300 . ?
C11 C10 1.414(16) . ?
C11 C12 1.387(12) . ?
C6 H1 0.9300 . ?
C6 C7 1.415(12) . ?
C3 C4 1.387(16) . ?
C3 C12 1.411(7) . ?
C3 C2 1.500(14) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.503(7) . ?
C15 C14 1.533(10) . ?
C12 H4 0.9300 . ?
C7 H2 0.9300 . ?
C18 H15 0.9700 . ?
C18 H16 0.9700 . ?
C18 C17 1.507(7) . ?
C18 C19 1.527(9) . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.505(9) . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C16 1.554(9) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C19 H17 0.9600 . ?
C19 H18 0.9600 . ?
C19 H19 0.9600 . ?

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
C6 C5 C1 121.1(5) . . ?
C6 C5 C4 119.8(8) . . ?
C4 C5 C1 119.0(9) . . ?
C8 C9 C4 120.6(4) . . ?
C8 C9 C10 123.0(7) . . ?
C4 C9 C10 116.4(8) . . ?
C9 C8 C10 120.0(4) . 2_576 ?
C9 C8 C7 120.1(7) . . ?
C7 C8 C10 119.9(8) . 2_576 ?
O1 C1 C5 122.6(10) . . ?
O1 C1 N1 118.3(9) . . ?
N1 C1 C5 119.1(5) . . ?
C1 N1 C13 118.7(4) . . ?
C1 N1 C2 124.9(8) . . ?
C2 N1 C13 116.2(9) . . ?
C10 C11 H3 118.7 . . ?
C12 C11 H3 118.7 . . ?
C12 C11 C10 122.6(4) . . ?
C5 C6 H1 118.9 . . ?
C5 C6 C7 122.2(5) . . ?
C7 C6 H1 118.9 . . ?
C4 C3 C12 121.5(8) . . ?
C4 C3 C2 123.0(5) . . ?
C12 C3 C2 115.4(9) . . ?
C9 C4 C5 118.3(9) . . ?
C3 C4 C5 119.7(8) . . ?
C3 C4 C9 121.9(4) . . ?
C9 C10 C8 117.0(8) . 2_576 ?
C11 C10 C9 119.5(7) . . ?
C11 C10 C8 123.5(4) . 2_576 ?
H9 C15 H10 108.0 . . ?
C16 C15 H9 109.3 . . ?
C16 C15 H10 109.3 . . ?
C16 C15 C14 111.4(4) . . ?
C14 C15 H9 109.3 . . ?
C14 C15 H10 109.3 . . ?
C11 C12 C3 118.1(9) . . ?
C11 C12 H4 120.9 . . ?
C3 C12 H4 120.9 . . ?
C8 C7 C6 118.8(8) . . ?
C8 C7 H2 120.6 . . ?
C6 C7 H2 120.6 . . ?
H15 C18 H16 107.9 . . ?
C17 C18 H15 109.1 . . ?
C17 C18 H16 109.1 . . ?
C17 C18 C19 112.4(4) . . ?
C19 C18 H15 109.1 . . ?
C19 C18 H16 109.1 . . ?
N1 C13 H6 109.5 . . ?
N1 C13 H5 109.5 . . ?
N1 C13 C14 110.6(4) . . ?
H6 C13 H5 108.1 . . ?
C14 C13 H6 109.5 . . ?
C14 C13 H5 109.5 . . ?
C18 C17 H13 109.2 . . ?
C18 C17 H14 109.2 . . ?
C18 C17 C16 112.2(4) . . ?
H13 C17 H14 107.9 . . ?
C16 C17 H13 109.2 . . ?
C16 C17 H14 109.2 . . ?
C15 C16 C17 113.3(4) . . ?
C15 C16 H11 108.9 . . ?
C15 C16 H12 108.9 . . ?
C17 C16 H11 108.9 . . ?
C17 C16 H12 108.9 . . ?
H11 C16 H12 107.7 . . ?
C15 C14 H7 108.9 . . ?
C15 C14 H8 108.9 . . ?
C13 C14 C15 113.2(4) . . ?
C13 C14 H7 108.9 . . ?
C13 C14 H8 108.9 . . ?
H7 C14 H8 107.7 . . ?
C18 C19 H17 109.5 . . ?
C18 C19 H18 109.5 . . ?
C18 C19 H19 109.5 . . ?
H17 C19 H18 109.5 . . ?
H17 C19 H19 109.5 . . ?
H18 C19 H19 109.5 . . ?
O2 C2 N1 121.3(10) . . ?
O2 C2 C3 124.5(6) . . ?
N1 C2 C3 114.2(10) . . ?

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 N1 C13 -1.9(9) . . . . ?
O1 C1 N1 C2 -176.7(5) . . . . ?
C5 C1 N1 C13 175.4(4) . . . . ?
C5 C1 N1 C2 0.7(10) . . . . ?
C5 C6 C7 C8 1.5(8) . . . . ?
C9 C8 C7 C6 0.7(8) . . . . ?
C8 C9 C4 C5 -0.2(8) . . . . ?
C8 C9 C4 C3 178.9(7) . . . . ?
C8 C9 C10 C8 2.1(9) . . . 2_576 ?
C8 C9 C10 C11 -178.6(6) . . . . ?
C1 C5 C6 C7 178.4(4) . . . . ?
C1 C5 C4 C9 -179.1(4) . . . . ?
C1 C5 C4 C3 1.9(9) . . . . ?
C1 N1 C13 C14 -84.9(8) . . . . ?
C1 N1 C2 O2 178.5(8) . . . . ?
C1 N1 C2 C3 -0.6(10) . . . . ?
N1 C13 C14 C15 168.7(7) . . . . ?
C6 C5 C1 O1 -5.4(9) . . . . ?
C6 C5 C1 N1 177.4(7) . . . . ?
C6 C5 C4 C9 2.3(9) . . . . ?
C6 C5 C4 C3 -176.8(6) . . . . ?
C4 C5 C1 O1 176.0(6) . . . . ?
C4 C5 C1 N1 -1.2(8) . . . . ?
C4 C5 C6 C7 -3.0(10) . . . . ?
C4 C9 C8 C10 179.3(4) . . . 2_576 ?
C4 C9 C8 C7 -1.3(8) . . . . ?
C4 C9 C10 C8 -179.3(4) . . . 2_576 ?
C4 C9 C10 C11 0.0(8) . . . . ?
C4 C3 C12 C11 0.8(10) . . . . ?
C4 C3 C2 O2 -177.9(9) . . . . ?
C4 C3 C2 N1 1.3(9) . . . . ?
C10 C9 C8 C10 -2.2(9) . . . 2_576 ?
C10 C9 C8 C7 177.2(4) . . . . ?
C10 C9 C4 C5 -178.8(5) . . . . ?
C10 C9 C4 C3 0.2(8) . . . . ?
C10 C8 C7 C6 -179.9(5) 2_576 . . . ?
C10 C11 C12 C3 -0.5(9) . . . . ?
C12 C11 C10 C9 0.1(10) . . . . ?
C12 C11 C10 C8 179.4(5) . . . 2_576 ?
C12 C3 C4 C5 178.4(4) . . . . ?
C12 C3 C4 C9 -0.7(10) . . . . ?
C12 C3 C2 O2 1.9(11) . . . . ?
C12 C3 C2 N1 -179.0(5) . . . . ?
C18 C17 C16 C15 -173.6(8) . . . . ?
C13 N1 C2 O2 3.7(11) . . . . ?
C13 N1 C2 C3 -175.5(4) . . . . ?
C16 C15 C14 C13 -169.7(8) . . . . ?
C14 C15 C16 C17 173.5(8) . . . . ?
C19 C18 C17 C16 174.0(10) . . . . ?
C2 N1 C13 C14 90.3(6) . . . . ?
C2 C3 C4 C5 -1.9(10) . . . . ?
C2 C3 C4 C9 179.1(4) . . . . ?
C2 C3 C12 C11 -178.9(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_PDI_C7_0_35GPa
_database_code_depnum_ccdc_archive 'CCDC 2493904'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT020_PDI_C7_0_35GPa      
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.257 Report
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle. The investigated needle-shaped single crystal was poorly 
diffractive and has low symmetry. 
;
_vrf_PLAT026_PDI_C7_0_35GPa      
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        34% Check 
RESPONSE: Due to the overall poor diffraction quality
of the needle-shaped crystal and low symmetry.
;
_vrf_PLAT029_PDI_C7_0_35GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.234 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C7_0_35GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       3.22 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C7_0_35GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02889 Ang. 
RESPONSE: The data come from high-pressure experiment, and part of the 
reflection can not be collected, affecting the bond precision.
;
_vrf_PLAT911_PDI_C7_0_35GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        467 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# start Validation Reply Form
_vrf_RINTA01_PDI_C7_0_35GPa      
;
PROBLEM: The value of Rint is greater than 0.25
            Rint given   0.257
RESPONSE: The investigated needle-shaped single crystal was poorly 
diffractive and has low symmetry. 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 high-pressure were unsuccessful.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-06-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        N,N-Diheptyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C38 H38 N2 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.744(2)
_cell_length_b                   8.250(4)
_cell_length_c                   19.015(16)
_cell_angle_alpha                78.90(9)
_cell_angle_beta                 89.92(11)
_cell_angle_gamma                82.32(4)
_cell_volume                     723.5(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    322
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.9860
_cell_measurement_theta_min      2.4770
_cell_oxdiff_angle_alpha         78.62(10)
_cell_oxdiff_angle_beta          89.45(11)
_cell_oxdiff_angle_gamma         82.37(4)
_cell_oxdiff_length_a            4.747(2)
_cell_oxdiff_length_b            8.247(4)
_cell_oxdiff_length_c            19.042(17)
_cell_oxdiff_measurement_reflns_used 334
_cell_oxdiff_volume              724.2(8)
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
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)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -8 -37 0.1000
8 1 -18 0.1000
8 1 20 0.1000
0 -8 25 0.1000
-5 -14 -11 0.1000
0 8 -25 0.1000
5 14 11 0.1000
0 8 37 0.1000
-8 -1 18 0.1000
-8 -1 -20 0.1000
5 -12 -9 0.1000
-5 12 9 0.1000

_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.054
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.1433 -8.0003 -37.2475 1.3406 0.3627 -0.4384
8.1014 1.0077 -18.0341 0.6935 -0.9159 -0.7781
7.9451 1.0125 20.2473 -0.7551 -0.8248 -0.8822
-0.1117 -7.9925 25.2117 -1.0229 0.5114 -0.6082
-4.9867 -14.0004 -11.0991 0.2979 1.2738 -0.3551
0.1117 7.9925 -25.2117 1.0229 -0.5114 0.6082
4.9867 14.0004 11.0991 -0.2979 -1.2738 0.3551
-0.1433 8.0003 37.2475 -1.3406 -0.3627 0.4384
-8.1014 -1.0077 18.0341 -0.6935 0.9159 0.7781
-7.9451 -1.0125 -20.2473 0.7551 0.8248 0.8822
5.0401 -11.9881 -8.9627 0.2373 0.1453 -1.3443
-5.0401 11.9881 8.9627 -0.2373 -0.1453 1.3443

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2574
_diffrn_reflns_av_unetI/netI     0.2993
_diffrn_reflns_Laue_measured_fraction_full 0.234
_diffrn_reflns_Laue_measured_fraction_max 0.217
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2080
_diffrn_reflns_point_group_measured_fraction_full 0.234
_diffrn_reflns_point_group_measured_fraction_max 0.217
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.562
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.234
_diffrn_measured_fraction_theta_max 0.217
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  30.00   0.50   12.00    --  -30.00   0.00   0.00  120
  2  ω    -30.00  30.00   0.50   12.00    --  -30.00   0.00 180.00  120
  3  ω    -30.00  30.00   0.50   12.00    --   30.00   0.00 180.00  120
  4  ω    -30.00  30.00   0.50   12.00    --   30.00   0.00   0.00  120
  5  ω    -15.49  17.01   0.50   12.00    --   30.00  39.49 -12.99   65
  6  ω    -15.49  17.01   0.50   12.00    --   30.00  39.49 167.01   65
  7  ω    -42.99  17.01   0.50   12.00    --  -30.00  39.49 -12.99  120
  8  ω    -42.99  17.01   0.50   12.00    --  -30.00  39.49 167.01  120
  9  ω    -58.98   1.02   0.50   12.00    --  -30.00  81.49 151.02  120
 10  ω    -58.98   1.02   0.50   12.00    --  -30.00  81.49 -28.98  120
 11  ω    -21.48   1.02   0.50   12.00    --   30.00  81.49 -28.98   45
 12  ω    -21.48   1.02   0.50   12.00    --   30.00  81.49 151.02   45
 13  ω    -52.05 -27.05   0.50   12.00    --   30.00 134.76 122.95   50
 14  ω    -52.05 -27.05   0.50   12.00    --   30.00 134.76 -57.05   50
 15  ω    -87.05 -27.05   0.50   12.00    --  -30.00 134.76 -57.05  120
 16  ω    -87.05 -27.05   0.50   12.00    --  -30.00 134.76 122.95  120
 17  φ    -30.00  30.00   0.50   12.00   0.00 -30.00   0.00    --   120
 18  φ    -30.00  30.00   0.50   12.00   0.00  30.00   0.00    --   120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_axis[1]    matrixX
_diffrn_orient_matrix_axis[2]    matrixY
_diffrn_orient_matrix_axis[3]    matrixZ
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0002949000
_diffrn_orient_matrix_UB_12      0.0086177000
_diffrn_orient_matrix_UB_13      -0.0378409000
_diffrn_orient_matrix_UB_21      -0.1016550000
_diffrn_orient_matrix_UB_22      -0.0563373000
_diffrn_orient_matrix_UB_23      0.0019726000
_diffrn_orient_matrix_UB_31      -0.1115416000
_diffrn_orient_matrix_UB_32      0.0676193000
_diffrn_orient_matrix_UB_33      -0.0031829000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_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.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                220
_reflns_number_total             641
_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 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       
'PROGRAM:BIS 8.5.1.2 Release/2023-09-07 && APEX6 2024.9-0                        '
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_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         0.120
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         641
_refine_ls_number_restraints     550
_refine_ls_R_factor_all          0.2604
_refine_ls_R_factor_gt           0.1019
_refine_ls_restrained_S_all      0.707
_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)+(0.0001P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1865
_refine_ls_wR_factor_ref         0.2600
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C11-C10 \\sim C9-C8 \\sim C7-C6 \\sim C5-C4 \\sim C3-C12
 with sigma of 0.02
 C18-C19B \\sim C18-C19A
 with sigma of 0.02
 O2-C2 \\sim O1-C1
 with sigma of 0.02
 C5-C4 \\sim C8-C9 \\sim C3-C2 \\sim C4-C3 \\sim C12-C3 \\sim C11-C12 \\sim
C10-C11 \\sim C4-C9 \\sim C5-C6 ~
 C6-C7 \\sim C7-C8 \\sim C10-C9
 with sigma of 0.02
2. Restrained planarity
 O2, O1, N1, C5, C4, C3, C12, C6, C2, C1, C10, C8, C9, C11, C7
 with sigma of 0.1
3. Rigid bond restraints
 C14, O2, C2, N1, C3, C13, C1, C4, C12, O1, C5, C9, C11, C15, C6, C8, C10, C16,
  C7, C17, C18, C19B, C19A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N1 \\sim O2 \\sim C2 \\sim C3 \\sim C13 \\sim C1 \\sim C4 \\sim C12 \\sim C14
\\sim O1 \\sim C5 \\sim C9 \\sim C11 \\sim C15 \\sim C6 \\sim C8 \\sim C10
\\sim C16 \\sim C7 \\sim C17 \\sim C18 \\sim C19B \\sim C19A: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(O2) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C8) \\sim
Ueq, Uanis(C9) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C3)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C2) \\sim Ueq,
Uanis(O1) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C1) \\sim
Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C10) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19B)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C4) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 O2, C5, C4, C10, C3, C8, C9, C12, C11, C2, O1, C6, C7, C1, N1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C18, C17, C16, C15, C14, C13
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H15A)=Sof(H16A)=Sof(C19A)=Sof(H17A)=Sof(H19A)=Sof(H18A)=1-FVAR(1)
 Sof(H16B)=Sof(H15B)=Sof(C19B)=Sof(H19B)=Sof(H18B)=Sof(H17B)=FVAR(1)
7.a Secondary CH2 refined with riding coordinates:
 C13(H6,H5), C14(H7,H8), C15(H9,H10), C16(H11,H12), C17(H14,H13), C18(H16B,
 H15B), C18(H15A,H16A)
7.b Aromatic/amide H refined with riding coordinates:
 C6(H1), C7(H2), C12(H4), C11(H3)
7.c Fitted hexagon refined as free rotating group:
 C5(C6,C7,C8,C9,C4)
7.d Idealised Me refined as rotating group:
 C19B(H19B,H18B,H17B), C19A(H17A,H19A,H18A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 1.0129(18) 0.0846(13) 0.394(2) 0.064(8) Uani 1 1 d D U . . .
O1 O 0.673(3) 0.5415(18) 0.2222(17) 0.077(6) Uani 1 1 d D U . . .
N1 N 0.841(3) 0.3211(16) 0.3036(16) 0.054(6) Uani 1 1 d . U . . .
C5 C 0.4341(16) 0.5078(13) 0.3362(10) 0.036(5) Uani 1 1 d DG U . . .
C6 C 0.238(2) 0.6501(12) 0.3156(10) 0.050(7) Uani 1 1 d DG U . . .
H1 H 0.245131 0.715775 0.270157 0.060 Uiso 1 1 calc R U . . .
C7 C 0.0309(16) 0.6944(9) 0.3628(12) 0.046(8) Uani 1 1 d DG U . . .
H2 H -0.100382 0.789709 0.348971 0.056 Uiso 1 1 calc R U . . .
C8 C 0.0201(17) 0.5963(13) 0.4307(11) 0.046(8) Uani 1 1 d DG U . . .
C9 C 0.216(2) 0.4540(13) 0.4513(10) 0.033(4) Uani 1 1 d DG U . . .
C4 C 0.4233(16) 0.4097(10) 0.4041(10) 0.038(3) Uani 1 1 d DG U . . .
C10 C 0.202(3) 0.3573(15) 0.5198(12) 0.031(4) Uani 1 1 d D U . . .
C3 C 0.625(3) 0.2684(15) 0.4188(16) 0.035(6) Uani 1 1 d D U . . .
C13 C 1.034(3) 0.260(2) 0.256(3) 0.055(8) Uani 1 1 d . U . . .
H6 H 1.208120 0.207366 0.282143 0.065 Uiso 1 1 calc R U . . .
H5 H 1.081636 0.353608 0.220431 0.065 Uiso 1 1 calc R U . . .
C14 C 0.927(3) 0.144(2) 0.220(3) 0.062(10) Uani 1 1 d . U . . .
H7 H 0.749405 0.196687 0.195681 0.075 Uiso 1 1 calc R U . . .
H8 H 0.884540 0.050291 0.255896 0.075 Uiso 1 1 calc R U . . .
C12 C 0.620(3) 0.1763(19) 0.4882(16) 0.044(6) Uani 1 1 d D U . . .
H4 H 0.757261 0.084197 0.502957 0.053 Uiso 1 1 calc R U . . .
C11 C 0.414(2) 0.2196(15) 0.5360(18) 0.037(6) Uani 1 1 d D U . . .
H3 H 0.416924 0.152848 0.581412 0.045 Uiso 1 1 calc R U . . .
C2 C 0.838(3) 0.218(2) 0.374(2) 0.043(6) Uani 1 1 d D U . . .
C15 C 1.140(3) 0.0698(19) 0.160(2) 0.076(11) Uani 1 1 d . U . . .
H9 H 1.175966 0.162084 0.122879 0.091 Uiso 1 1 calc R U . . .
H10 H 1.320938 0.020139 0.183841 0.091 Uiso 1 1 calc R U . . .
C1 C 0.645(4) 0.468(3) 0.287(2) 0.048(6) Uani 1 1 d D U . . .
C16 C 1.022(3) -0.0575(19) 0.127(2) 0.089(11) Uani 1 1 d . U . . .
H11 H 0.860462 -0.003515 0.095596 0.106 Uiso 1 1 calc R U . . .
H12 H 0.955257 -0.140480 0.163746 0.106 Uiso 1 1 calc R U . . .
C17 C 1.244(3) -0.144(2) 0.083(3) 0.081(11) Uani 1 1 d . U . . .
H14 H 1.400417 -0.201184 0.114621 0.097 Uiso 1 1 calc R U . . .
H13 H 1.319077 -0.058717 0.047977 0.097 Uiso 1 1 calc R U . . .
C18 C 1.138(3) -0.274(3) 0.041(3) 0.079(7) Uani 1 1 d D U . . .
H16B H 1.017481 -0.340075 0.072191 0.095 Uiso 0.40(4) 1 calc R U P A 1
H15B H 1.021916 -0.212355 -0.000040 0.095 Uiso 0.40(4) 1 calc R U P A 1
H15A H 0.942237 -0.237321 0.024626 0.095 Uiso 0.60(4) 1 calc R U P A 2
H16A H 1.253937 -0.281931 -0.000707 0.095 Uiso 0.60(4) 1 calc R U P A 2
C19B C 1.347(9) -0.379(8) 0.017(8) 0.081(16) Uani 0.40(4) 1 d D U P A 1
H19B H 1.364415 -0.486316 0.048214 0.122 Uiso 0.40(4) 1 calc R U P A 1
H18B H 1.524269 -0.334754 0.016968 0.122 Uiso 0.40(4) 1 calc R U P A 1
H17B H 1.299033 -0.389635 -0.030683 0.122 Uiso 0.40(4) 1 calc R U P A 1
C19A C 1.160(9) -0.423(4) 0.086(4) 0.10(2) Uani 0.60(4) 1 d D U P A 2
H17A H 1.020918 -0.419110 0.122423 0.153 Uiso 0.60(4) 1 calc R U P A 2
H19A H 1.346806 -0.450269 0.107483 0.153 Uiso 0.60(4) 1 calc R U P A 2
H18A H 1.126147 -0.507345 0.059294 0.153 Uiso 0.60(4) 1 calc R U P A 2


_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 C2 1.28(2) . ?
O1 C1 1.28(3) . ?
N1 C13 1.40(4) . ?
N1 C2 1.44(4) . ?
N1 C1 1.41(2) . ?
C5 C6 1.3900 . ?
C5 C4 1.3900 . ?
C5 C1 1.42(3) . ?
C6 H1 0.9300 . ?
C6 C7 1.3900 . ?
C7 H2 0.9300 . ?
C7 C8 1.3900 . ?
C8 C9 1.3900 . ?
C8 C10 1.47(2) 2_566 ?
C9 C4 1.3900 . ?
C9 C10 1.396(17) . ?
C4 C3 1.390(12) . ?
C10 C11 1.399(12) . ?
C3 C12 1.392(17) . ?
C3 C2 1.398(16) . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.43(4) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C15 1.67(5) . ?
C12 H4 0.9300 . ?
C12 C11 1.393(15) . ?
C11 H3 0.9300 . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.50(3) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C17 1.53(3) . ?
C17 H14 0.9700 . ?
C17 H13 0.9700 . ?
C17 C18 1.58(4) . ?
C18 H16B 0.9700 . ?
C18 H15B 0.9700 . ?
C18 H15A 0.9700 . ?
C18 H16A 0.9700 . ?
C18 C19B 1.36(4) . ?
C18 C19A 1.35(4) . ?
C19B H19B 0.9600 . ?
C19B H18B 0.9600 . ?
C19B H17B 0.9600 . ?
C19A H17A 0.9600 . ?
C19A H19A 0.9600 . ?
C19A H18A 0.9600 . ?

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
C13 N1 C2 116(2) . . ?
C13 N1 C1 125(3) . . ?
C1 N1 C2 119(2) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C1 118.2(14) . . ?
C4 C5 C1 121.8(15) . . ?
C5 C6 H1 120.0 . . ?
C5 C6 C7 120.0 . . ?
C7 C6 H1 120.0 . . ?
C6 C7 H2 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 H2 120.0 . . ?
C7 C8 C10 119.8(13) . 2_566 ?
C9 C8 C7 120.0 . . ?
C9 C8 C10 120.2(13) . 2_566 ?
C8 C9 C4 120.0 . . ?
C8 C9 C10 119.1(12) . . ?
C4 C9 C10 120.9(12) . . ?
C5 C4 C3 115.4(15) . . ?
C9 C4 C5 120.0 . . ?
C9 C4 C3 124.6(15) . . ?
C9 C10 C8 120.7(13) . 2_566 ?
C9 C10 C11 114.6(18) . . ?
C11 C10 C8 125(2) . 2_566 ?
C4 C3 C12 115(2) . . ?
C4 C3 C2 127(2) . . ?
C12 C3 C2 118.2(18) . . ?
N1 C13 H6 109.0 . . ?
N1 C13 H5 109.0 . . ?
N1 C13 C14 113.0(15) . . ?
H6 C13 H5 107.8 . . ?
C14 C13 H6 109.0 . . ?
C14 C13 H5 109.0 . . ?
C13 C14 H7 108.2 . . ?
C13 C14 H8 108.2 . . ?
C13 C14 C15 116.2(16) . . ?
H7 C14 H8 107.4 . . ?
C15 C14 H7 108.2 . . ?
C15 C14 H8 108.2 . . ?
C3 C12 H4 119.4 . . ?
C3 C12 C11 121.2(19) . . ?
C11 C12 H4 119.4 . . ?
C10 C11 H3 118.0 . . ?
C12 C11 C10 124(2) . . ?
C12 C11 H3 118.0 . . ?
O2 C2 N1 123(3) . . ?
O2 C2 C3 121(3) . . ?
C3 C2 N1 116(2) . . ?
C14 C15 H9 108.8 . . ?
C14 C15 H10 108.8 . . ?
H9 C15 H10 107.7 . . ?
C16 C15 C14 113.9(14) . . ?
C16 C15 H9 108.8 . . ?
C16 C15 H10 108.8 . . ?
O1 C1 N1 110(3) . . ?
O1 C1 C5 129(2) . . ?
N1 C1 C5 121(3) . . ?
C15 C16 H11 109.2 . . ?
C15 C16 H12 109.2 . . ?
C15 C16 C17 112.0(13) . . ?
H11 C16 H12 107.9 . . ?
C17 C16 H11 109.2 . . ?
C17 C16 H12 109.2 . . ?
C16 C17 H14 108.2 . . ?
C16 C17 H13 108.2 . . ?
C16 C17 C18 116.3(13) . . ?
H14 C17 H13 107.4 . . ?
C18 C17 H14 108.2 . . ?
C18 C17 H13 108.2 . . ?
C17 C18 H16B 108.4 . . ?
C17 C18 H15B 108.4 . . ?
C17 C18 H15A 110.0 . . ?
C17 C18 H16A 110.0 . . ?
H16B C18 H15B 107.4 . . ?
H15A C18 H16A 108.4 . . ?
C19B C18 C17 116(3) . . ?
C19B C18 H16B 108.4 . . ?
C19B C18 H15B 108.4 . . ?
C19A C18 C17 108(4) . . ?
C19A C18 H15A 110.0 . . ?
C19A C18 H16A 110.0 . . ?
C18 C19B H19B 109.5 . . ?
C18 C19B H18B 109.5 . . ?
C18 C19B H17B 109.5 . . ?
H19B C19B H18B 109.5 . . ?
H19B C19B H17B 109.5 . . ?
H18B C19B H17B 109.5 . . ?
C18 C19A H17A 109.5 . . ?
C18 C19A H19A 109.5 . . ?
C18 C19A H18A 109.5 . . ?
H17A C19A H19A 109.5 . . ?
H17A C19A H18A 109.5 . . ?
H19A C19A H18A 109.5 . . ?

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
N1 C13 C14 C15 178(3) . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C5 C4 C3 C12 177.0(10) . . . . ?
C5 C4 C3 C2 1.5(16) . . . . ?
C6 C5 C4 C9 0.0 . . . . ?
C6 C5 C4 C3 178.7(10) . . . . ?
C6 C5 C1 O1 -5(3) . . . . ?
C6 C5 C1 N1 -176.9(14) . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C6 C7 C8 C10 -179.2(10) . . . 2_566 ?
C7 C8 C9 C4 0.0 . . . . ?
C7 C8 C9 C10 179.9(9) . . . . ?
C8 C9 C4 C5 0.0 . . . . ?
C8 C9 C4 C3 -178.6(11) . . . . ?
C8 C9 C10 C8 0.9(13) . . . 2_566 ?
C8 C9 C10 C11 -178.2(9) . . . . ?
C8 C10 C11 C12 179.2(14) 2_566 . . . ?
C9 C4 C3 C12 -4.4(17) . . . . ?
C9 C4 C3 C2 -179.8(11) . . . . ?
C9 C10 C11 C12 -1.7(19) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C4 C5 C1 O1 176(2) . . . . ?
C4 C5 C1 N1 4(2) . . . . ?
C4 C9 C10 C8 -179.2(12) . . . 2_566 ?
C4 C9 C10 C11 1.7(14) . . . . ?
C4 C3 C12 C11 4(2) . . . . ?
C4 C3 C2 O2 179.7(19) . . . . ?
C4 C3 C2 N1 -2(2) . . . . ?
C10 C8 C9 C4 179.2(10) 2_566 . . . ?
C10 C8 C9 C10 -0.9(14) 2_566 . . . ?
C10 C9 C4 C5 -179.9(10) . . . . ?
C10 C9 C4 C3 1.5(12) . . . . ?
C3 C12 C11 C10 -1(2) . . . . ?
C13 N1 C2 O2 5(3) . . . . ?
C13 N1 C2 C3 -173.4(15) . . . . ?
C13 N1 C1 O1 -2(3) . . . . ?
C13 N1 C1 C5 172.1(18) . . . . ?
C13 C14 C15 C16 178(3) . . . . ?
C14 C15 C16 C17 -170(3) . . . . ?
C12 C3 C2 O2 4(2) . . . . ?
C12 C3 C2 N1 -177.6(15) . . . . ?
C2 N1 C13 C14 84(4) . . . . ?
C2 N1 C1 O1 -178.4(16) . . . . ?
C2 N1 C1 C5 -5(2) . . . . ?
C2 C3 C12 C11 -179.9(12) . . . . ?
C15 C16 C17 C18 -177(3) . . . . ?
C1 N1 C13 C14 -93(3) . . . . ?
C1 N1 C2 O2 -178(2) . . . . ?
C1 N1 C2 C3 4(2) . . . . ?
C1 C5 C6 C7 -179.0(13) . . . . ?
C1 C5 C4 C9 179.0(13) . . . . ?
C1 C5 C4 C3 -2.3(14) . . . . ?
C16 C17 C18 C19B -164(7) . . . . ?
C16 C17 C18 C19A -86(4) . . . . ?

loop_
_axis.id
_axis.system
_axis.type
_axis.equipment
_axis.parity
_axis.depends_on
_axis.zero
_axis.vector[1]
_axis.vector[2]
_axis.vector[3]
source abstract . source . . . 0.99999999 0.00000000 -0.00015680
omega abstract rotation goniometer -1 . -0.21346534 0.00000000 0.00000000
1.00000000
kappa abstract rotation goniometer -1 omega 0.00000000 -0.76667378 0.00000000
0.64203684
phi abstract rotation goniometer -1 kappa . 0.00000000 0.00000000 1.00000000
theta abstract rotation goniometer -1 . -0.32229000 0.00000000 0.00000000
1.00000000
matrixX abstract general general . phi . 1.00000000 0.00000000 0.00000000
matrixY abstract general general . phi . 0.00000000 1.00000000 0.00000000
matrixZ abstract general general . phi . 0.00000000 0.00000000 1.00000000
dacX abstract translation general . phi . 0.00000000 1.00000000 0.00000000
dacY abstract translation general . phi . -1.00000000 0.00000000 0.00000000
dacZ abstract translation general . phi . 0.00000000 0.00000000 1.00000000

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.165
_oxdiff_exptl_absorpt_empirical_full_min 0.423
####################################################################### 
# 
# 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_PDI_C7_0_50GPa
_database_code_depnum_ccdc_archive 'CCDC 2493905'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PDI_C7_0_50GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      15.00 Degree
RESPONSE: Due to the specificity of the applied measuring technique and use
of a diamond-anvil cell limiting the access of the X-ray radiation to the
measured sample. A full set of data was collected.
;
_vrf_PLAT029_PDI_C7_0_50GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.391 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C7_0_50GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       3.80 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C7_0_50GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.019 Ang.  
RESPONSE: The data come from high-pressure experiment, and part of the 
reflection can not be collected, affecting the bond precision.
;
_vrf_PLAT911_PDI_C7_0_50GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        734 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
_vrf_RINTA01_PDI_C7_0_50GPa      
;
PROBLEM: The value of Rint is greater than 0.18
            Rint given   0.184
RESPONSE: The investigated needle-shaped single crystal was poorly 
diffractive and has low symmetry. 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 high-pressure were unsuccessful.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-06-09

_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        N,N-Diheptyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         C38H36N2O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.6610(6)
_cell_length_b                   8.3844(14)
_cell_length_c                   18.520(7)
_cell_angle_alpha                78.29(3)
_cell_angle_beta                 87.11(3)
_cell_angle_gamma                83.681(14)
_cell_volume                     704.1(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1011
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.6210
_cell_measurement_theta_min      2.4620
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.452
_exptl_absorpt_correction_T_min  0.371
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 8 32 0.1000
7 1 19 0.1000
7 1 -18 0.1000
0 8 -28 0.1000
-5 13 2 0.1000
0 -8 28 0.1000
5 -13 -2 0.1000
0 -8 -32 0.1000
-7 -1 -19 0.1000
-7 -1 18 0.1000
5 14 3 0.1887
-5 -14 -3 0.1887

_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_oxdiff_absorpt_process_details 
;
Gaussian integration over a grid
of 16 x 16 x 16 points =  4096 total grid points
  Based upon method of Burnham (1966)

 Data corrected for diamond-anvil cell absorption
 Note that exptl_absorpt_correction_tmin and _tmax
 the total correction factors applied to the intensities
 The individual factors are: 
         range of dac transmission factors (min-max)      0.399     0.454
         range of gasket transmission (min-max)           0.914     1.000
         range of P media transmission (min-max)          1.000     1.000

 thickness of diamond anvil 1: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 1:  0.000 mm, mu =  0.0000 mm-1

 thickness of diamond anvil 2: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 2:  0.000 mm, mu =  0.0000 mm-1

    Gasket shadowing corrections were made based upon
    Gasket thickness = 300.0 microns, radius = 300.0 microns
    Gasket absorption coeff =        21.00 mm-1
    REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF 
 FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00

    Absorption coeff of pressure medium =   0.00 mm-1
;
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0351 8.0099 31.9360 1.0818 -0.3148 0.6570
6.9804 1.0059 19.0132 0.6920 0.9622 0.4569
7.0266 0.9893 -17.9139 -0.7515 0.9902 0.4005
0.0399 7.9829 -27.9459 -1.2590 -0.2695 0.5654
-4.9970 12.9950 1.9582 -0.1724 -1.1973 0.7399
-0.0399 -7.9829 27.9459 1.2590 0.2695 -0.5654
4.9970 -12.9950 -1.9582 0.1724 1.1973 -0.7399
0.0351 -8.0099 -31.9360 -1.0818 0.3148 -0.6570
-6.9804 -1.0059 -19.0132 -0.6920 -0.9622 -0.4569
-7.0266 -0.9893 17.9139 0.7515 -0.9902 -0.4005
5.0073 13.9920 3.0286 -0.1949 0.2126 1.3202
-5.0073 -13.9920 -3.0286 0.1949 -0.2126 -1.3202

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1845
_diffrn_reflns_av_unetI/netI     0.1025
_diffrn_reflns_Laue_measured_fraction_full 0.391
_diffrn_reflns_Laue_measured_fraction_max 0.218
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4109
_diffrn_reflns_point_group_measured_fraction_full 0.391
_diffrn_reflns_point_group_measured_fraction_max 0.218
_diffrn_reflns_theta_full        15.000
_diffrn_reflns_theta_max         28.231
_diffrn_reflns_theta_min         2.494
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.391
_diffrn_measured_fraction_theta_max 0.218
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  30.00   0.50    8.00    --  -30.00   0.00   0.00  120
  2  ω    -30.00  30.00   0.50    8.00    --  -30.00   0.00 180.00  120
  3  ω    -30.00  30.00   0.50    8.00    --   30.00   0.00 180.00  120
  4  ω    -30.00  30.00   0.50    8.00    --   30.00   0.00   0.00  120
  5  ω    -15.49  17.01   0.50    8.00    --   30.00  39.49 -12.99   65
  6  ω    -15.49  17.01   0.50    8.00    --   30.00  39.49 167.01   65
  7  ω    -42.99  17.01   0.50    8.00    --  -30.00  39.49 -12.99  120
  8  ω    -42.99  17.01   0.50    8.00    --  -30.00  39.49 167.01  120
  9  ω    -58.98   1.02   0.50    8.00    --  -30.00  81.49 151.02  120
 10  ω    -58.98   1.02   0.50    8.00    --  -30.00  81.49 -28.98  120
 11  ω    -36.48   1.02   0.50    8.00    --   15.00  81.49 -28.98   75
 12  ω    -36.48   1.02   0.50    8.00    --   15.00  81.49 151.02   75
 13  ω    -67.05 -27.05   0.50    8.00    --   15.00 134.76 122.95   80
 14  ω    -67.05 -27.05   0.50    8.00    --   15.00 134.76 -57.05   80
 15  ω    -87.05 -27.05   0.50    8.00    --  -30.00 134.76 -57.05  120
 16  ω    -87.05 -27.05   0.50    8.00    --  -30.00 134.76 122.95  120
 17  φ    -30.00  30.00   0.50    8.00   0.00 -30.00   0.00    --   120
 18  φ    -30.00  25.50   0.50    8.00   0.00  30.00   0.00    --   111
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_axis[1]    matrixX
_diffrn_orient_matrix_axis[2]    matrixY
_diffrn_orient_matrix_axis[3]    matrixZ
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0043519000
_diffrn_orient_matrix_UB_12      -0.0208346000
_diffrn_orient_matrix_UB_13      0.0390936000
_diffrn_orient_matrix_UB_21      0.1446249000
_diffrn_orient_matrix_UB_22      -0.0364397000
_diffrn_orient_matrix_UB_23      -0.0005593000
_diffrn_orient_matrix_UB_31      0.0502592000
_diffrn_orient_matrix_UB_32      0.0760314000
_diffrn_orient_matrix_UB_33      0.0015571000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 0.50(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                408
_reflns_number_total             759
_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 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_collection       
'PROGRAM:BIS 8.5.1.2 Release/2023-09-07 && APEX6 2024.9-0                        '
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_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         0.171
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.050
_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     200
_refine_ls_number_reflns         759
_refine_ls_number_restraints     261
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.0694
_refine_ls_restrained_S_all      0.852
_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)+(0.0957P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1826
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C1) \\sim
Ueq, Uanis(N1) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C3)
\\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C12) \\sim Ueq,
Uanis(C7) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O1) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
2. Rigid body (RIGU) restrains
 O1, O2, C5, C9, C8, C1, N1, C11, C6, C3, C4, C10, C16, C12, C7, C19, C14, C18,
  C17, C15, C20, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Secondary CH2 refined with riding coordinates:
 C16(H9,H10), C19(H15,H16), C14(H6,H5), C18(H13,H14), C17(H11,H12), C15(H8,H7)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H3), C6(H1), C12(H4), C7(H2)
3.c Idealised Me refined as rotating group:
 C20(H17,H18,H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.9964(7) 0.4912(6) 0.6128(8) 0.048(6) Uani 1 1 d . U . . .
O2 O 0.6655(13) 0.7864(10) 0.7857(10) 0.061(4) Uani 1 1 d . U . . .
C5 C 0.6171(12) 0.6974(9) 0.5779(12) 0.030(3) Uani 1 1 d . U . . .
C9 C 0.2126(11) 0.9091(9) 0.5497(12) 0.029(3) Uani 1 1 d . U . . .
C8 C 0.2004(11) 0.8746(9) 0.4790(11) 0.026(3) Uani 1 1 d . U . . .
C1 C 0.8285(12) 0.6029(9) 0.6307(12) 0.034(3) Uani 1 1 d . U . . .
N1 N 0.8386(10) 0.6419(8) 0.6985(9) 0.038(3) Uani 1 1 d . U . . .
C11 C 0.0422(13) 1.0677(10) 0.6405(12) 0.036(3) Uani 1 1 d . U . . .
H3 H -0.078655 1.153328 0.654044 0.043 Uiso 1 1 calc R U . . .
C6 C 0.6074(12) 0.6671(10) 0.5100(12) 0.032(3) Uani 1 1 d . U . . .
H1 H 0.739772 0.586889 0.495933 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4351(12) 0.8547(9) 0.6706(12) 0.032(3) Uani 1 1 d . U . . .
C4 C 0.4206(12) 0.8229(9) 0.5983(11) 0.029(3) Uani 1 1 d . U . . .
C10 C 0.0160(12) 1.0341(9) 0.5752(12) 0.031(3) Uani 1 1 d . U . . .
C15 C 1.1133(10) 0.2624(8) 0.8397(10) 0.051(9) Uani 1 1 d . . . . .
H9 H 1.280204 0.239507 0.808538 0.061 Uiso 1 1 calc R U . . .
H10 H 1.178684 0.306570 0.879767 0.061 Uiso 1 1 calc R U . . .
C12 C 0.2483(10) 0.9784(8) 0.6914(10) 0.040(3) Uani 1 1 d . U . . .
H4 H 0.257357 1.002678 0.737994 0.048 Uiso 1 1 calc R U . . .
C7 C 0.4012(8) 0.7538(7) 0.4588(9) 0.033(3) Uani 1 1 d . U . . .
H2 H 0.399647 0.730372 0.411837 0.040 Uiso 1 1 calc R U . . .
C18 C 1.0730(11) -0.1931(8) 0.9347(11) 0.074(15) Uani 1 1 d . . . . .
H15 H 0.986149 -0.220404 0.892875 0.088 Uiso 1 1 calc R U . . .
H16 H 0.920463 -0.179627 0.971269 0.088 Uiso 1 1 calc R U . . .
C13 C 1.0375(11) 0.5395(8) 0.7515(10) 0.044(5) Uani 1 1 d . . . . .
H6 H 1.092868 0.603646 0.785650 0.052 Uiso 1 1 calc R U . . .
H5 H 1.210865 0.503655 0.725499 0.052 Uiso 1 1 calc R U . . .
C17 C 1.1997(11) -0.0335(8) 0.9099(11) 0.051(11) Uani 1 1 d . . . . .
H13 H 1.362854 -0.049006 0.876547 0.061 Uiso 1 1 calc R U . . .
H14 H 1.271319 -0.001027 0.952517 0.061 Uiso 1 1 calc R U . . .
C16 C 0.9833(10) 0.1049(8) 0.8710(10) 0.050(12) Uani 1 1 d . . . . .
H11 H 0.898498 0.068127 0.831280 0.060 Uiso 1 1 calc R U . . .
H12 H 0.828942 0.126740 0.905898 0.060 Uiso 1 1 calc R U . . .
C14 C 0.8999(10) 0.3888(8) 0.7949(12) 0.051(8) Uani 1 1 d . . . . .
H8 H 0.749438 0.424642 0.827948 0.061 Uiso 1 1 calc R U . . .
H7 H 0.809779 0.337865 0.760564 0.061 Uiso 1 1 calc R U . . .
C19 C 1.2902(12) -0.3348(9) 0.9675(13) 0.089(16) Uani 1 1 d . . . . .
H17 H 1.430982 -0.356726 0.930180 0.134 Uiso 1 1 calc R U . . .
H18 H 1.191833 -0.430368 0.985643 0.134 Uiso 1 1 calc R U . . .
H19 H 1.384889 -0.306702 1.007356 0.134 Uiso 1 1 calc R U . . .
C2 C 0.6471(18) 0.7628(13) 0.7236(15) 0.040(3) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.240(9) . ?
O2 C2 1.21(3) . ?
C5 C1 1.47(2) . ?
C5 C6 1.34(3) . ?
C5 C4 1.415(10) . ?
C9 C8 1.40(3) . ?
C9 C4 1.395(19) . ?
C9 C10 1.452(11) . ?
C8 C10 1.49(2) 2_576 ?
C8 C7 1.397(9) . ?
C1 N1 1.36(2) . ?
N1 C13 1.461(15) . ?
N1 C2 1.412(12) . ?
C11 H3 0.9300 . ?
C11 C10 1.31(3) . ?
C11 C12 1.421(18) . ?
C6 H1 0.9300 . ?
C6 C7 1.418(17) . ?
C3 C4 1.42(3) . ?
C3 C12 1.382(10) . ?
C3 C2 1.47(2) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.509(12) . ?
C15 C14 1.515(14) . ?
C12 H4 0.9300 . ?
C7 H2 0.9300 . ?
C18 H15 0.9700 . ?
C18 H16 0.9700 . ?
C18 C17 1.499(12) . ?
C18 C19 1.520(12) . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.539(17) . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C16 1.537(12) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C14 H8 0.9700 . ?
C14 H7 0.9700 . ?
C19 H17 0.9600 . ?
C19 H18 0.9600 . ?
C19 H19 0.9600 . ?

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
C6 C5 C1 120.9(9) . . ?
C6 C5 C4 118.8(14) . . ?
C4 C5 C1 120.4(16) . . ?
C8 C9 C10 122.5(13) . . ?
C4 C9 C8 120.1(8) . . ?
C4 C9 C10 117.4(16) . . ?
C9 C8 C10 121.8(8) . 2_576 ?
C7 C8 C9 118.6(12) . . ?
C7 C8 C10 119.6(15) . 2_576 ?
O1 C1 C5 119.9(16) . . ?
O1 C1 N1 121.1(13) . . ?
N1 C1 C5 119.0(8) . . ?
C1 N1 C13 117.9(7) . . ?
C1 N1 C2 124.2(13) . . ?
C2 N1 C13 117.5(15) . . ?
C10 C11 H3 118.8 . . ?
C10 C11 C12 122.5(7) . . ?
C12 C11 H3 118.8 . . ?
C5 C6 H1 119.0 . . ?
C5 C6 C7 121.9(7) . . ?
C7 C6 H1 119.0 . . ?
C4 C3 C2 122.1(9) . . ?
C12 C3 C4 119.2(13) . . ?
C12 C3 C2 118.6(16) . . ?
C5 C4 C3 118.2(13) . . ?
C9 C4 C5 120.8(17) . . ?
C9 C4 C3 121.0(8) . . ?
C9 C10 C8 115.7(16) . 2_576 ?
C11 C10 C9 120.7(13) . . ?
C11 C10 C8 123.5(8) . 2_576 ?
H9 C15 H10 107.9 . . ?
C16 C15 H9 109.2 . . ?
C16 C15 H10 109.2 . . ?
C16 C15 C14 112.1(5) . . ?
C14 C15 H9 109.2 . . ?
C14 C15 H10 109.2 . . ?
C11 C12 H4 120.5 . . ?
C3 C12 C11 119.0(15) . . ?
C3 C12 H4 120.5 . . ?
C8 C7 C6 119.8(14) . . ?
C8 C7 H2 120.1 . . ?
C6 C7 H2 120.1 . . ?
H15 C18 H16 107.6 . . ?
C17 C18 H15 108.7 . . ?
C17 C18 H16 108.7 . . ?
C17 C18 C19 114.0(5) . . ?
C19 C18 H15 108.7 . . ?
C19 C18 H16 108.7 . . ?
N1 C13 H6 109.3 . . ?
N1 C13 H5 109.3 . . ?
N1 C13 C14 111.5(6) . . ?
H6 C13 H5 108.0 . . ?
C14 C13 H6 109.3 . . ?
C14 C13 H5 109.3 . . ?
C18 C17 H13 108.9 . . ?
C18 C17 H14 108.9 . . ?
C18 C17 C16 113.3(5) . . ?
H13 C17 H14 107.7 . . ?
C16 C17 H13 108.9 . . ?
C16 C17 H14 108.9 . . ?
C15 C16 C17 114.1(5) . . ?
C15 C16 H11 108.7 . . ?
C15 C16 H12 108.7 . . ?
C17 C16 H11 108.7 . . ?
C17 C16 H12 108.7 . . ?
H11 C16 H12 107.6 . . ?
C15 C14 C13 113.6(5) . . ?
C15 C14 H8 108.9 . . ?
C15 C14 H7 108.9 . . ?
C13 C14 H8 108.9 . . ?
C13 C14 H7 108.9 . . ?
H8 C14 H7 107.7 . . ?
C18 C19 H17 109.5 . . ?
C18 C19 H18 109.5 . . ?
C18 C19 H19 109.5 . . ?
H17 C19 H18 109.5 . . ?
H17 C19 H19 109.5 . . ?
H18 C19 H19 109.5 . . ?
O2 C2 N1 119.9(15) . . ?
O2 C2 C3 124.0(10) . . ?
N1 C2 C3 116.1(18) . . ?

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 N1 C13 -4.8(16) . . . . ?
O1 C1 N1 C2 -177.3(9) . . . . ?
C5 C1 N1 C13 176.1(7) . . . . ?
C5 C1 N1 C2 3.7(18) . . . . ?
C5 C6 C7 C8 -0.1(15) . . . . ?
C9 C8 C7 C6 1.2(14) . . . . ?
C8 C9 C4 C5 -1.5(16) . . . . ?
C8 C9 C4 C3 -179.4(12) . . . . ?
C8 C9 C10 C8 -0.4(17) . . . 2_576 ?
C8 C9 C10 C11 -177.0(13) . . . . ?
C1 C5 C6 C7 178.5(7) . . . . ?
C1 C5 C4 C9 -177.7(8) . . . . ?
C1 C5 C4 C3 0.3(16) . . . . ?
C1 N1 C13 C14 -85.6(14) . . . . ?
C1 N1 C2 O2 177.7(14) . . . . ?
C1 N1 C2 C3 -2.9(18) . . . . ?
N1 C13 C14 C15 168.8(10) . . . . ?
C6 C5 C1 O1 -1.6(15) . . . . ?
C6 C5 C1 N1 177.5(12) . . . . ?
C6 C5 C4 C9 2.6(17) . . . . ?
C6 C5 C4 C3 -179.4(11) . . . . ?
C4 C5 C1 O1 178.7(10) . . . . ?
C4 C5 C1 N1 -2.3(14) . . . . ?
C4 C5 C6 C7 -1.8(18) . . . . ?
C4 C9 C8 C10 -179.0(7) . . . 2_576 ?
C4 C9 C8 C7 -0.4(17) . . . . ?
C4 C9 C10 C8 179.1(7) . . . 2_576 ?
C4 C9 C10 C11 2.5(18) . . . . ?
C4 C3 C12 C11 1.5(16) . . . . ?
C4 C3 C2 O2 -179.9(16) . . . . ?
C4 C3 C2 N1 0.7(18) . . . . ?
C10 C9 C8 C10 0.4(18) . . . 2_576 ?
C10 C9 C8 C7 179.0(7) . . . . ?
C10 C9 C4 C5 179.0(10) . . . . ?
C10 C9 C4 C3 1.1(15) . . . . ?
C10 C8 C7 C6 179.9(7) 2_576 . . . ?
C10 C11 C12 C3 2.2(17) . . . . ?
C12 C11 C10 C9 -4(2) . . . . ?
C12 C11 C10 C8 179.5(7) . . . 2_576 ?
C12 C3 C4 C5 179.0(7) . . . . ?
C12 C3 C4 C9 -3.0(17) . . . . ?
C12 C3 C2 O2 1(2) . . . . ?
C12 C3 C2 N1 -177.9(10) . . . . ?
C18 C17 C16 C15 -174.8(13) . . . . ?
C13 N1 C2 O2 5(2) . . . . ?
C13 N1 C2 C3 -175.4(8) . . . . ?
C16 C15 C14 C13 -170.3(13) . . . . ?
C14 C15 C16 C17 173.9(11) . . . . ?
C19 C18 C17 C16 175.1(12) . . . . ?
C2 N1 C13 C14 87.3(11) . . . . ?
C2 C3 C4 C5 0.4(19) . . . . ?
C2 C3 C4 C9 178.4(9) . . . . ?
C2 C3 C12 C11 -179.9(9) . . . . ?

############################
loop_
_axis.id
_axis.system
_axis.type
_axis.equipment
_axis.parity
_axis.depends_on
_axis.zero
_axis.vector[1]
_axis.vector[2]
_axis.vector[3]
source abstract . source . . . 0.99999978 0.00000000 -0.00066794
omega abstract rotation goniometer -1 . -0.04791000 0.00000000 0.00000000
1.00000000
kappa abstract rotation goniometer -1 omega 0.06246000 -0.76736014 0.00000000
0.64121636
phi abstract rotation goniometer -1 kappa . 0.00007138 0.00000000 1.00000000
theta abstract rotation goniometer -1 . -0.37066000 0.00000000 0.00000000
1.00000000
matrixX abstract general general . phi . 1.00000000 0.00000000 0.00000000
matrixY abstract general general . phi . 0.00000000 1.00000000 0.00000000
matrixZ abstract general general . phi . 0.00000000 0.00000000 1.00000000
dacX abstract translation general . phi . 0.00000000 1.00000000 0.00000000
dacY abstract translation general . phi . -1.00000000 0.00000000 0.00000000
dacZ abstract translation general . phi . 0.00000000 0.00000000 1.00000000


_hp_anvil_anvil_thickness        1.95
_hp_anvil_material               diamond
_hp_cell_type                    'Diamond anvil cell'
_hp_open_angle                   40.00
_ins_header                      
;
TITL d in P-1 
REM P-1 (#2 in standard setting)
CELL 0.71073   4.661026   8.384427  18.520303  78.2915  87.1117  83.6807
ZERR    1.00   0.000606   0.001396   0.006852   0.0265   0.0313   0.0136
LATT  1
SFAC C H N O
UNIT 38.00 36.00 2.00 4.00
SIZE 0.20 0.23 0.37
TREF
HKLF 4
END
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.421
_oxdiff_exptl_absorpt_empirical_full_min 0.318
####################################################################### 
# 
# 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_PDI_C5_1_40GPa
_database_code_depnum_ccdc_archive 'CCDC 2493897'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PDI_C5_1_40GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      15.00 Degree
RESPONSE: Due to the specificity of the applied 
measuring technique and use of a diamond-anvil cell limiting the access of 
the X-ray radiation to the measured sample. A full set of data was collected.
;
_vrf_PLAT029_PDI_C5_1_40GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.347 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C5_1_40GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.78 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C5_1_40GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03889 Ang. 
RESPONSE: The data come from high-pressure experiment, and part of the 
reflection can not be collected, affecting the bond precision.
;
_vrf_PLAT911_PDI_C5_1_40GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        580 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-02-28

_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C5
_chemical_name_systematic        N,N-Dipentyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C34 H30 N2 O4'
_chemical_formula_sum            'C34 H30 N2 O4'
_chemical_formula_weight         530.60
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.5189(16)
_cell_length_b                   8.3710(17)
_cell_length_c                   15.611(8)
_cell_angle_alpha                85.46(5)
_cell_angle_beta                 83.42(6)
_cell_angle_gamma                85.97(2)
_cell_volume                     583.7(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    796
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.1970
_cell_measurement_theta_min      4.5380
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.451
_exptl_absorpt_correction_T_min  0.372
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model (Absorb Angel (2004) J. Appl. Cryst. 37:486-492)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 11 1 0.1114
0 0 -22 0.0213
0 0 22 0.0213
-6 -2 -4 0.0596
-6 -4 -5 0.0663
1 -11 -1 0.1283
6 4 5 0.0669
6 2 4 0.0551

_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_oxdiff_absorpt_process_details 
;
Gaussian integration over a grid
of 16 x 16 x 16 points =  4096 total grid points
  Based upon method of Burnham (1966)

 Data corrected for diamond-anvil cell absorption
 Note that exptl_absorpt_correction_tmin and _tmax
 the total correction factors applied to the intensities
 The individual factors are: 
         range of dac transmission factors (min-max)      0.404     0.453
         range of gasket transmission (min-max)           0.916     1.000
         range of P media transmission (min-max)          1.000     1.000

 thickness of diamond anvil 1: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 1:  0.000 mm, mu =  0.0000 mm-1

 thickness of diamond anvil 2: 19.500 mm, mu =  0.0202 mm-1
       thickness of platten 2:  0.000 mm, mu =  0.0000 mm-1

    Gasket shadowing corrections were made based upon
    Gasket thickness = 190.0 microns, radius = 194.0 microns
    Gasket absorption coeff =        21.00 mm-1
    REFLECTION WAS CONSIDERED TOTALLY OBSCURED IF 
 FRACTION CRYSTAL ILLUMINATED WAS LESS THAN 0.00

    Non-absorbing pressure medium
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_unetI/netI     0.0977
_diffrn_reflns_Laue_measured_fraction_full 0.347
_diffrn_reflns_Laue_measured_fraction_max 0.199
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2888
_diffrn_reflns_point_group_measured_fraction_full 0.347
_diffrn_reflns_point_group_measured_fraction_max 0.199
_diffrn_reflns_theta_full        15.000
_diffrn_reflns_theta_max         27.025
_diffrn_reflns_theta_min         4.595
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.347
_diffrn_measured_fraction_theta_max 0.199
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.25  49.00   0.75    7.50    --    0.16 -53.00  17.00   83
  2  ω    -13.25  49.00   0.75    7.50    --    0.16 -53.00-162.00   83
  3  ω    -22.25  40.00   0.75   20.00    --  -30.73 -26.00   7.00   83
  4  ω    -66.25  -4.00   0.75   20.00    --  -30.73  97.00 -35.00   83
  5  ω    -35.25  27.00   0.75   20.00    --  -30.73  13.00 176.00   83
  6  ω     13.75  40.00   0.75   20.00    --  -30.73-114.00-135.00   35
  7  ω    -54.25   8.00   0.75   20.00    --  -30.73  67.00 157.00   83
  8  ω    -13.25  22.00   0.75   20.00    --  -30.73 -53.00-162.00   47
  9  ω    -13.25  22.00   0.75   20.00    --  -30.73 -53.00  17.00   47
 10  ω      5.00  29.00   0.75   20.00    --  -30.73 -97.00  35.00   32
 11  ω    -43.25 -11.00   0.75   20.00    --  -30.73  19.00   0.00   43
 12  ω     38.00  89.00   0.75   20.00    --   31.04-135.00-123.00   68
 13  ω     21.00  56.25   0.75   20.00    --   31.04 -77.00-150.00   47
 14  ω    -39.25 -13.00   0.75   20.00    --   31.04 114.00 -45.00   35
 15  ω    -14.25  36.00   0.75   20.00    --   31.04 -13.00   3.00   67
 16  ω     21.00  56.25   0.75   20.00    --   31.04 -77.00  30.00   47
 17  ω    -21.25  14.00   0.75   20.00    --   31.04  53.00 -17.00   47
 18  ω    -30.00   0.00   0.75   20.00    --   31.04   0.00-150.00   40
 19  ω    -70.00 -13.75   0.75    7.50    --    0.16 114.00 135.00   75
 20  ω    -53.00 -26.00   0.75    7.50    --    0.16  37.00   0.00   36
 21  ω    -53.00 -26.00   0.75   20.00    --  -30.73  37.00   0.00   36
 22  ω    -18.25  44.00   0.75   20.00    --  -30.73 -39.00-167.00   83
 23  ω     -9.25  44.00   0.75   20.00    --   31.04 -19.00-180.00   71
 24  ω    -21.25  14.00   0.75   20.00    --   31.04  53.00 162.00   47
 25  ω     -5.00  19.00   0.75   20.00    --   31.04  57.00 -30.00   32
 26  ω     25.00  76.00   0.75   20.00    --   31.04-114.00  45.00   68
 27  ω    -31.00  23.00   0.75   20.00    --   31.04  26.00  -7.00   72
 28  ω    -39.25 -13.00   0.75   20.00    --   31.04 114.00 135.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 1.40(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                253
_reflns_number_total             509
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.232
_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   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         509
_refine_ls_number_restraints     460
_refine_ls_R_factor_all          0.2010
_refine_ls_R_factor_gt           0.1019
_refine_ls_restrained_S_all      0.725
_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)+9.9915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.2291
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5-C4 \\sim C4-C3 \\sim C3-C2 \\sim C5-C1 \\sim C6-C5 \\sim C6-C7 \\sim C7-C8
\\sim C9-C8 \\sim C4-C9 \\sim C10-
 C9 \\sim C11-C10 \\sim C12-C11 \\sim C3-C12
 with sigma of 0.02
 N1-C1 \\sim N1-C2
 with sigma of 0.02
 N1-C13 \\sim C14-C13 \\sim C15-C14 \\sim C16-C15 \\sim C17-C16
 with sigma of 0.02
 O2-C2 \\sim O1-C1
 with sigma of 0.02
3. Rigid bond restraints
 O2, N1, C8, C9, C10, C11, C12, C3, C4, C5, C6, C7, C1, C2, O1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
O1 \\sim O2 \\sim N1 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C3
\\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C1 \\sim C2: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16)
\\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms
of 0.2
Uanis(C4) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C15) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(O1) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1, N1, C8, C9, C10, C11, C12, C3, C4, C5, C6, C7, C1, C2, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Secondary CH2 refined with riding coordinates:
 C13(H6,H5), C14(H8,H7), C15(H9,H10), C16(H11,H12)
6.b Aromatic/amide H refined with riding coordinates:
 C11(H3), C12(H4), C6(H1), C7(H2)
6.c Idealised Me refined as rotating group:
 C17(H13,H14,H15)
;
_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 -1.048(3) 0.4493(13) 0.129(3) 0.033(8) Uani 1 1 d D U . . .
O2 O -0.821(5) 0.0620(18) 0.336(3) 0.040(6) Uani 1 1 d D U . . .
N1 N -0.945(3) 0.2529(16) 0.231(2) 0.020(5) Uani 1 1 d D U . . .
C8 C -0.194(5) 0.1352(19) -0.024(3) 0.026(7) Uani 1 1 d D U . . .
C9 C -0.228(4) 0.0640(19) 0.061(2) 0.022(6) Uani 1 1 d D U . . .
C10 C -0.050(5) -0.0749(19) 0.084(3) 0.022(8) Uani 1 1 d D U . . .
C11 C -0.128(5) -0.141(2) 0.168(3) 0.029(9) Uani 1 1 d D U . . .
H3 H -0.013942 -0.231827 0.186425 0.035 Uiso 1 1 calc R U . . .
C12 C -0.360(4) -0.0840(17) 0.228(3) 0.025(8) Uani 1 1 d D U . . .
H4 H -0.397877 -0.135269 0.282488 0.030 Uiso 1 1 calc R U . . .
C3 C -0.535(4) 0.0536(17) 0.2015(19) 0.015(6) Uani 1 1 d D U . . .
C4 C -0.471(4) 0.1254(17) 0.1169(18) 0.017(5) Uani 1 1 d D U . . .
C5 C -0.650(4) 0.262(2) 0.091(2) 0.025(6) Uani 1 1 d D U . . .
C6 C -0.605(4) 0.326(2) 0.005(2) 0.023(6) Uani 1 1 d D U . . .
H1 H -0.736461 0.408489 -0.013498 0.027 Uiso 1 1 calc R U . . .
C7 C -0.369(3) 0.2707(17) -0.054(3) 0.025(7) Uani 1 1 d D U . . .
H2 H -0.329903 0.319701 -0.109569 0.030 Uiso 1 1 calc R U . . .
C1 C -0.888(4) 0.325(2) 0.147(2) 0.024(6) Uani 1 1 d D U . . .
C2 C -0.771(5) 0.115(3) 0.259(2) 0.022(6) Uani 1 1 d D U . . .
C13 C -1.160(4) 0.331(2) 0.299(2) 0.034(7) Uani 1 1 d D U . . .
H6 H -1.228108 0.248664 0.342891 0.040 Uiso 1 1 calc R U . . .
H5 H -1.332430 0.377814 0.272625 0.040 Uiso 1 1 calc R U . . .
C14 C -1.026(4) 0.460(2) 0.343(3) 0.037(9) Uani 1 1 d D U . . .
H8 H -0.887663 0.408288 0.380992 0.044 Uiso 1 1 calc R U . . .
H7 H -0.911649 0.525499 0.298639 0.044 Uiso 1 1 calc R U . . .
C15 C -1.247(4) 0.570(2) 0.395(3) 0.033(6) Uani 1 1 d D U . . .
H9 H -1.337732 0.510353 0.445526 0.040 Uiso 1 1 calc R U . . .
H10 H -1.403102 0.612104 0.359960 0.040 Uiso 1 1 calc R U . . .
C16 C -1.083(5) 0.707(2) 0.422(4) 0.041(13) Uani 1 1 d D U . . .
H11 H -0.985255 0.764260 0.370860 0.049 Uiso 1 1 calc R U . . .
H12 H -0.932771 0.665594 0.458428 0.049 Uiso 1 1 calc R U . . .
C17 C -1.310(5) 0.820(3) 0.470(4) 0.060(18) Uani 1 1 d D U . . .
H13 H -1.471456 0.849217 0.435761 0.090 Uiso 1 1 calc R U . . .
H14 H -1.215736 0.914261 0.480662 0.090 Uiso 1 1 calc R U . . .
H15 H -1.385653 0.766537 0.523926 0.090 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 1.25(2) . ?
O2 C2 1.26(3) . ?
N1 C1 1.40(3) . ?
N1 C2 1.41(3) . ?
N1 C13 1.510(19) . ?
C8 C9 1.410(19) . ?
C8 C10 1.45(5) 2 ?
C8 C7 1.417(16) . ?
C9 C10 1.411(16) . ?
C9 C4 1.410(17) . ?
C10 C11 1.406(19) . ?
C11 H3 0.9300 . ?
C11 C12 1.404(19) . ?
C12 H4 0.9300 . ?
C12 C3 1.410(15) . ?
C3 C4 1.414(18) . ?
C3 C2 1.410(18) . ?
C4 C5 1.414(16) . ?
C5 C6 1.407(19) . ?
C5 C1 1.405(19) . ?
C6 H1 0.9300 . ?
C6 C7 1.408(18) . ?
C7 H2 0.9300 . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.517(17) . ?
C14 H8 0.9700 . ?
C14 H7 0.9700 . ?
C14 C15 1.517(19) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.517(16) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C17 1.52(2) . ?
C17 H13 0.9600 . ?
C17 H14 0.9600 . ?
C17 H15 0.9600 . ?

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 C2 121(2) . . ?
C1 N1 C13 121.8(17) . . ?
C2 N1 C13 117(2) . . ?
C9 C8 C10 118.5(18) . 2 ?
C9 C8 C7 125(2) . . ?
C7 C8 C10 117(3) . 2 ?
C8 C9 C10 120(2) . . ?
C8 C9 C4 116.5(19) . . ?
C4 C9 C10 123(3) . . ?
C9 C10 C8 121(3) . 2 ?
C11 C10 C8 125(2) . 2 ?
C11 C10 C9 114(3) . . ?
C10 C11 H3 116.8 . . ?
C12 C11 C10 126(2) . . ?
C12 C11 H3 116.8 . . ?
C11 C12 H4 121.1 . . ?
C11 C12 C3 118(3) . . ?
C3 C12 H4 121.1 . . ?
C12 C3 C4 119(2) . . ?
C12 C3 C2 120(2) . . ?
C2 C3 C4 121.4(18) . . ?
C9 C4 C3 120.4(18) . . ?
C9 C4 C5 122(2) . . ?
C3 C4 C5 118(2) . . ?
C6 C5 C4 118(2) . . ?
C1 C5 C4 122(2) . . ?
C1 C5 C6 120(2) . . ?
C5 C6 H1 118.6 . . ?
C5 C6 C7 123(2) . . ?
C7 C6 H1 118.6 . . ?
C8 C7 H2 122.3 . . ?
C6 C7 C8 115(2) . . ?
C6 C7 H2 122.3 . . ?
O1 C1 N1 116(3) . . ?
O1 C1 C5 125(3) . . ?
N1 C1 C5 119(2) . . ?
O2 C2 N1 118(3) . . ?
O2 C2 C3 123(3) . . ?
C3 C2 N1 119(2) . . ?
N1 C13 H6 108.8 . . ?
N1 C13 H5 108.8 . . ?
N1 C13 C14 113.7(19) . . ?
H6 C13 H5 107.7 . . ?
C14 C13 H6 108.8 . . ?
C14 C13 H5 108.8 . . ?
C13 C14 H8 108.3 . . ?
C13 C14 H7 108.3 . . ?
H8 C14 H7 107.4 . . ?
C15 C14 C13 115.9(17) . . ?
C15 C14 H8 108.3 . . ?
C15 C14 H7 108.3 . . ?
C14 C15 H9 109.9 . . ?
C14 C15 H10 109.9 . . ?
C14 C15 C16 109.1(19) . . ?
H9 C15 H10 108.3 . . ?
C16 C15 H9 109.9 . . ?
C16 C15 H10 109.9 . . ?
C15 C16 H11 110.0 . . ?
C15 C16 H12 110.0 . . ?
C15 C16 C17 108(2) . . ?
H11 C16 H12 108.4 . . ?
C17 C16 H11 110.0 . . ?
C17 C16 H12 110.0 . . ?
C16 C17 H13 109.5 . . ?
C16 C17 H14 109.5 . . ?
C16 C17 H15 109.5 . . ?
H13 C17 H14 109.5 . . ?
H13 C17 H15 109.5 . . ?
H14 C17 H15 109.5 . . ?

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
N1 C13 C14 C15 165(2) . . . . ?
C8 C9 C10 C8 8(3) . . . 2 ?
C8 C9 C10 C11 -174(2) . . . . ?
C8 C9 C4 C3 175.4(19) . . . . ?
C8 C9 C4 C5 -7(3) . . . . ?
C8 C10 C11 C12 179(2) 2 . . . ?
C9 C8 C7 C6 -5(3) . . . . ?
C9 C10 C11 C12 1(3) . . . . ?
C9 C4 C5 C6 8(3) . . . . ?
C9 C4 C5 C1 -179(2) . . . . ?
C10 C8 C9 C10 -8(3) 2 . . . ?
C10 C8 C9 C4 -179.4(17) 2 . . . ?
C10 C8 C7 C6 179.8(19) 2 . . . ?
C10 C9 C4 C3 4(3) . . . . ?
C10 C9 C4 C5 -178.2(19) . . . . ?
C10 C11 C12 C3 0(3) . . . . ?
C11 C12 C3 C4 1(3) . . . . ?
C11 C12 C3 C2 180(2) . . . . ?
C12 C3 C4 C9 -3(3) . . . . ?
C12 C3 C4 C5 179.4(16) . . . . ?
C12 C3 C2 O2 6(4) . . . . ?
C12 C3 C2 N1 -179.5(18) . . . . ?
C3 C4 C5 C6 -175(2) . . . . ?
C3 C4 C5 C1 -1(3) . . . . ?
C4 C9 C10 C8 179.0(19) . . . 2 ?
C4 C9 C10 C11 -3(3) . . . . ?
C4 C3 C2 O2 -175(3) . . . . ?
C4 C3 C2 N1 -1(3) . . . . ?
C4 C5 C6 C7 -7(3) . . . . ?
C4 C5 C1 O1 177(2) . . . . ?
C4 C5 C1 N1 2(3) . . . . ?
C5 C6 C7 C8 6(3) . . . . ?
C6 C5 C1 O1 -9(4) . . . . ?
C6 C5 C1 N1 175(2) . . . . ?
C7 C8 C9 C10 177.5(16) . . . . ?
C7 C8 C9 C4 6(3) . . . . ?
C1 N1 C2 O2 176(3) . . . . ?
C1 N1 C2 C3 1(3) . . . . ?
C1 N1 C13 C14 -81(2) . . . . ?
C1 C5 C6 C7 179.3(16) . . . . ?
C2 N1 C1 O1 -177.7(19) . . . . ?
C2 N1 C1 C5 -2(3) . . . . ?
C2 N1 C13 C14 90(2) . . . . ?
C2 C3 C4 C9 178.4(18) . . . . ?
C2 C3 C4 C5 0(3) . . . . ?
C13 N1 C1 O1 -7(3) . . . . ?
C13 N1 C1 C5 168.8(17) . . . . ?
C13 N1 C2 O2 5(3) . . . . ?
C13 N1 C2 C3 -169.9(18) . . . . ?
C13 C14 C15 C16 -171(3) . . . . ?
C14 C15 C16 C17 178(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
- Detector area scaling
- B-factor correction
;
####################################################################### 
# 
# 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_PDI_C7_0_95GPa
_database_code_depnum_ccdc_archive 'CCDC 2493906'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C7_0_95GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.324 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C7_0_95GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.97 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT911_PDI_C7_0_95GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        1205 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-06-09

_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        N,N-Diheptyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_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 -0.0004 0.0007 '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 -0.0003 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0008 0.0027 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.64199(18)
_cell_length_b                   8.2981(3)
_cell_length_c                   18.553(3)
_cell_angle_alpha                78.624(7)
_cell_angle_beta                 87.207(6)
_cell_angle_gamma                83.704(3)
_cell_volume                     696.12(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    756
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.3720
_cell_measurement_theta_min      3.0370
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.995
_exptl_absorpt_coefficient_mu    0.048
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.096
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.325
_diffrn_reflns_Laue_measured_fraction_max 0.205
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3290
_diffrn_reflns_point_group_measured_fraction_full 0.325
_diffrn_reflns_point_group_measured_fraction_max 0.205
_diffrn_reflns_theta_full        17.166
_diffrn_reflns_theta_max         22.933
_diffrn_reflns_theta_min         3.057
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.325
_diffrn_measured_fraction_theta_max 0.205
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     20.00  94.00   0.25    1.00  57.05   0.00-134.76    --   296
  2  φ     20.00  94.00   0.25    1.00  57.05   0.00-134.76    --   296
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.4919
_diffrn_source                   synchrotron
_diffrn_special_details          
;
 Data were collected at room conditions (296 K / 0.95 GPa)
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                796
_reflns_number_total             1193
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.228
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1193
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0829
_refine_ls_restrained_S_all      1.064
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2345
_refine_ls_wR_factor_ref         0.2612
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq,
Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C1) \\sim
Ueq, Uanis(N1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O1)
\\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq,
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.04
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C18(H18A,H18B), C13(H13A,H13B), C17(H17A,H17B), C16(H16A,
 H16B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C6(H6), C12(H12), C7(H7)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 0.9965(5) 0.4897(4) 0.6142(4) 0.084(4) Uani 1 1 d . U . . .
O2 O 0.6625(7) 0.7861(6) 0.7864(6) 0.074(5) Uani 1 1 d . U . . .
C5 C 0.6169(6) 0.6978(5) 0.5771(6) 0.048(3) Uani 1 1 d . U . . .
C9 C 0.2102(6) 0.9103(5) 0.5488(5) 0.041(3) Uani 1 1 d . U . . .
C8 C 0.2022(6) 0.8737(4) 0.4789(5) 0.044(3) Uani 1 1 d . U . . .
C1 C 0.8298(7) 0.6021(5) 0.6305(6) 0.050(3) Uani 1 1 d . U . . .
N1 N 0.8351(5) 0.6412(5) 0.6987(5) 0.052(3) Uani 1 1 d . U . . .
C11 C 0.0403(7) 1.0670(6) 0.6429(6) 0.049(3) Uani 1 1 d . U . . .
H3 H -0.086230 1.149672 0.657993 0.059 Uiso 1 1 calc R U . . .
C6 C 0.6100(6) 0.6690(5) 0.5081(6) 0.051(3) Uani 1 1 d . U . . .
H1 H 0.747062 0.590242 0.493651 0.061 Uiso 1 1 calc R U . . .
C3 C 0.4341(7) 0.8560(5) 0.6681(6) 0.048(3) Uani 1 1 d . U . . .
C4 C 0.4202(6) 0.8222(5) 0.5994(5) 0.042(3) Uani 1 1 d . U . . .
C10 C 0.0178(6) 1.0362(5) 0.5741(5) 0.044(3) Uani 1 1 d . U . . .
C15 C 1.1127(7) 0.2613(5) 0.8395(6) 0.059(3) Uani 1 1 d . U . . .
H9 H 1.280589 0.237451 0.808724 0.071 Uiso 1 1 calc R U . . .
H10 H 1.177981 0.306369 0.879603 0.071 Uiso 1 1 calc R U . . .
C12 C 0.2470(7) 0.9787(5) 0.6913(6) 0.054(3) Uani 1 1 d . U . . .
H4 H 0.259311 1.001346 0.738154 0.065 Uiso 1 1 calc R U . . .
C7 C 0.4017(6) 0.7542(4) 0.4567(5) 0.043(3) Uani 1 1 d . U . . .
H2 H 0.398850 0.730892 0.409725 0.052 Uiso 1 1 calc R U . . .
C18 C 1.0734(8) -0.1939(5) 0.9348(6) 0.069(4) Uani 1 1 d . U . . .
H16 H 0.923957 -0.180132 0.972128 0.083 Uiso 1 1 calc R U . . .
H15 H 0.981845 -0.221489 0.893536 0.083 Uiso 1 1 calc R U . . .
C13 C 1.0369(6) 0.5382(5) 0.7536(6) 0.055(3) Uani 1 1 d . U . . .
H6 H 1.086869 0.603710 0.788136 0.066 Uiso 1 1 calc R U . . .
H5 H 1.214023 0.502722 0.728583 0.066 Uiso 1 1 calc R U . . .
C17 C 1.2020(7) -0.0335(5) 0.9097(6) 0.059(3) Uani 1 1 d . U . . .
H13 H 1.365909 -0.050332 0.876573 0.071 Uiso 1 1 calc R U . . .
H14 H 1.273444 0.000753 0.951978 0.071 Uiso 1 1 calc R U . . .
C16 C 0.9835(7) 0.1054(5) 0.8702(6) 0.058(3) Uani 1 1 d . U . . .
H11 H 0.899882 0.067072 0.830486 0.069 Uiso 1 1 calc R U . . .
H12 H 0.827481 0.127988 0.904641 0.069 Uiso 1 1 calc R U . . .
C14 C 0.9006(7) 0.3887(5) 0.7947(6) 0.058(3) Uani 1 1 d . U . . .
H7 H 0.812720 0.337582 0.759700 0.069 Uiso 1 1 calc R U . . .
H8 H 0.747327 0.424331 0.827294 0.069 Uiso 1 1 calc R U . . .
C2 C 0.6496(8) 0.7648(7) 0.7229(8) 0.051(4) Uani 1 1 d . U . . .
C19 C 1.2908(10) -0.3337(6) 0.9654(8) 0.124(9) Uani 1 1 d . . . . .
H17 H 1.423152 -0.358921 0.926830 0.186 Uiso 1 1 calc R U . . .
H18 H 1.192920 -0.429068 0.986042 0.186 Uiso 1 1 calc R U . . .
H19 H 1.396095 -0.303047 1.003025 0.186 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 1.221(5) . ?
O2 C2 1.232(16) . ?
C5 C1 1.484(11) . ?
C5 C6 1.350(14) . ?
C5 C4 1.413(6) . ?
C9 C8 1.393(13) . ?
C9 C4 1.424(10) . ?
C9 C10 1.434(6) . ?
C8 C10 1.486(10) 2_576 ?
C8 C7 1.390(5) . ?
C1 N1 1.369(13) . ?
N1 C13 1.489(9) . ?
N1 C2 1.395(7) . ?
C11 H3 0.9300 . ?
C11 C10 1.362(13) . ?
C11 C12 1.391(10) . ?
C6 H1 0.9300 . ?
C6 C7 1.421(10) . ?
C3 C4 1.363(14) . ?
C3 C12 1.386(6) . ?
C3 C2 1.495(13) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.485(7) . ?
C15 C14 1.511(8) . ?
C12 H4 0.9300 . ?
C7 H2 0.9300 . ?
C18 H16 0.9700 . ?
C18 H15 0.9700 . ?
C18 C17 1.499(7) . ?
C18 C19 1.492(8) . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.508(8) . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C16 1.542(8) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C19 H17 0.9600 . ?
C19 H18 0.9600 . ?
C19 H19 0.9600 . ?

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
C6 C5 C1 121.3(4) . . ?
C6 C5 C4 119.9(7) . . ?
C4 C5 C1 118.7(9) . . ?
C8 C9 C4 120.1(4) . . ?
C8 C9 C10 123.6(7) . . ?
C4 C9 C10 116.3(8) . . ?
C9 C8 C10 120.5(4) . 2_576 ?
C7 C8 C9 120.9(6) . . ?
C7 C8 C10 118.6(8) . 2_576 ?
O1 C1 C5 120.7(9) . . ?
O1 C1 N1 120.4(8) . . ?
N1 C1 C5 118.9(4) . . ?
C1 N1 C13 118.6(4) . . ?
C1 N1 C2 124.6(8) . . ?
C2 N1 C13 116.7(9) . . ?
C10 C11 H3 119.0 . . ?
C10 C11 C12 122.0(4) . . ?
C12 C11 H3 119.0 . . ?
C5 C6 H1 118.7 . . ?
C5 C6 C7 122.6(4) . . ?
C7 C6 H1 118.7 . . ?
C4 C3 C12 121.5(7) . . ?
C4 C3 C2 122.8(4) . . ?
C12 C3 C2 115.7(9) . . ?
C5 C4 C9 118.6(9) . . ?
C3 C4 C5 120.0(7) . . ?
C3 C4 C9 121.3(4) . . ?
C9 C10 C8 115.8(8) . 2_576 ?
C11 C10 C9 120.6(6) . . ?
C11 C10 C8 123.6(4) . 2_576 ?
H9 C15 H10 107.9 . . ?
C16 C15 H9 109.1 . . ?
C16 C15 H10 109.1 . . ?
C16 C15 C14 112.3(4) . . ?
C14 C15 H9 109.1 . . ?
C14 C15 H10 109.1 . . ?
C11 C12 H4 120.8 . . ?
C3 C12 C11 118.3(9) . . ?
C3 C12 H4 120.8 . . ?
C8 C7 C6 117.8(8) . . ?
C8 C7 H2 121.1 . . ?
C6 C7 H2 121.1 . . ?
H16 C18 H15 107.7 . . ?
C17 C18 H16 108.9 . . ?
C17 C18 H15 108.9 . . ?
C19 C18 H16 108.9 . . ?
C19 C18 H15 108.9 . . ?
C19 C18 C17 113.3(4) . . ?
N1 C13 H6 109.5 . . ?
N1 C13 H5 109.5 . . ?
N1 C13 C14 110.9(4) . . ?
H6 C13 H5 108.0 . . ?
C14 C13 H6 109.5 . . ?
C14 C13 H5 109.5 . . ?
C18 C17 H13 109.0 . . ?
C18 C17 H14 109.0 . . ?
C18 C17 C16 112.9(4) . . ?
H13 C17 H14 107.8 . . ?
C16 C17 H13 109.0 . . ?
C16 C17 H14 109.0 . . ?
C15 C16 C17 113.8(3) . . ?
C15 C16 H11 108.8 . . ?
C15 C16 H12 108.8 . . ?
C17 C16 H11 108.8 . . ?
C17 C16 H12 108.8 . . ?
H11 C16 H12 107.7 . . ?
C15 C14 H7 108.9 . . ?
C15 C14 H8 108.9 . . ?
C13 C14 C15 113.6(3) . . ?
C13 C14 H7 108.9 . . ?
C13 C14 H8 108.9 . . ?
H7 C14 H8 107.7 . . ?
O2 C2 N1 119.8(9) . . ?
O2 C2 C3 125.1(5) . . ?
N1 C2 C3 115.0(10) . . ?
C18 C19 H17 109.5 . . ?
C18 C19 H18 109.5 . . ?
C18 C19 H19 109.5 . . ?
H17 C19 H18 109.5 . . ?
H17 C19 H19 109.5 . . ?
H18 C19 H19 109.5 . . ?

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 N1 C13 -3.2(8) . . . . ?
O1 C1 N1 C2 -178.5(5) . . . . ?
C5 C1 N1 C13 176.4(4) . . . . ?
C5 C1 N1 C2 1.0(9) . . . . ?
C5 C6 C7 C8 1.2(7) . . . . ?
C9 C8 C7 C6 1.1(7) . . . . ?
C8 C9 C4 C5 -0.2(7) . . . . ?
C8 C9 C4 C3 179.7(6) . . . . ?
C8 C9 C10 C8 1.4(8) . . . 2_576 ?
C8 C9 C10 C11 -179.1(5) . . . . ?
C1 C5 C6 C7 177.5(4) . . . . ?
C1 C5 C4 C9 -178.0(4) . . . . ?
C1 C5 C4 C3 2.0(8) . . . . ?
C1 N1 C13 C14 -85.6(7) . . . . ?
C1 N1 C2 O2 176.8(6) . . . . ?
C1 N1 C2 C3 0.3(9) . . . . ?
N1 C13 C14 C15 168.0(6) . . . . ?
C6 C5 C1 O1 -3.1(8) . . . . ?
C6 C5 C1 N1 177.3(6) . . . . ?
C6 C5 C4 C9 2.5(8) . . . . ?
C6 C5 C4 C3 -177.4(5) . . . . ?
C4 C5 C1 O1 177.4(5) . . . . ?
C4 C5 C1 N1 -2.2(7) . . . . ?
C4 C5 C6 C7 -3.0(8) . . . . ?
C4 C9 C8 C10 179.4(4) . . . 2_576 ?
C4 C9 C8 C7 -1.5(7) . . . . ?
C4 C9 C10 C8 -179.5(4) . . . 2_576 ?
C4 C9 C10 C11 0.1(8) . . . . ?
C4 C3 C12 C11 0.5(8) . . . . ?
C4 C3 C2 O2 -176.8(8) . . . . ?
C4 C3 C2 N1 -0.5(8) . . . . ?
C10 C9 C8 C10 -1.4(8) . . . 2_576 ?
C10 C9 C8 C7 177.6(4) . . . . ?
C10 C9 C4 C5 -179.5(5) . . . . ?
C10 C9 C4 C3 0.5(7) . . . . ?
C10 C8 C7 C6 -179.9(4) 2_576 . . . ?
C10 C11 C12 C3 0.0(8) . . . . ?
C12 C11 C10 C9 -0.3(9) . . . . ?
C12 C11 C10 C8 179.2(4) . . . 2_576 ?
C12 C3 C4 C5 179.1(4) . . . . ?
C12 C3 C4 C9 -0.8(9) . . . . ?
C12 C3 C2 O2 3.4(9) . . . . ?
C12 C3 C2 N1 179.7(5) . . . . ?
C18 C17 C16 C15 -175.3(8) . . . . ?
C13 N1 C2 O2 1.4(9) . . . . ?
C13 N1 C2 C3 -175.1(4) . . . . ?
C16 C15 C14 C13 -171.3(8) . . . . ?
C14 C15 C16 C17 174.2(7) . . . . ?
C2 N1 C13 C14 90.1(6) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . . ?
C2 C3 C4 C9 179.3(4) . . . . ?
C2 C3 C12 C11 -179.6(4) . . . . ?
C19 C18 C17 C16 173.5(9) . . . . ?

_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_PDI_C7_0_16GPa
_database_code_depnum_ccdc_archive 'CCDC 2493903'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PDI_C7_0_16GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      22.50 Degree
RESPONSE: Due to the specificity of the applied measuring technique and use
of a diamond-anvil cell limiting the access of the X-ray radiation to the
measured sample. A full set of data was collected.
;
_vrf_PLAT029_PDI_C7_0_16GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.24 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C7_0_16GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.62 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C7_0_16GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03947 Ang.  
RESPONSE: The data come from high-pressure experiment, and part of the 
reflection can not be collected, affecting the bond precision.
;
_vrf_PLAT911_PDI_C7_0_16GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        733 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-06-09

_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        N,N-Diheptyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7703(5)
_cell_length_b                   8.2802(12)
_cell_length_c                   19.028(10)
_cell_angle_alpha                79.32(3)
_cell_angle_beta                 89.42(3)
_cell_angle_gamma                82.010(11)
_cell_volume                     731.3(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2980
_cell_measurement_theta_min      2.5120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.94764
_exptl_absorpt_correction_T_min  0.94764
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.024
_exptl_crystal_size_rad          0.400
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_Laue_measured_fraction_full 0.240
_diffrn_reflns_Laue_measured_fraction_max 0.125
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1413
_diffrn_reflns_point_group_measured_fraction_full 0.240
_diffrn_reflns_point_group_measured_fraction_max 0.125
_diffrn_reflns_theta_full        22.500
_diffrn_reflns_theta_max         30.383
_diffrn_reflns_theta_min         2.528
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.240
_diffrn_measured_fraction_theta_max 0.125
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  30.00   0.50    6.00    --  -30.00   0.00   0.00  120
  2  ω    -30.00  30.00   0.50    6.00    --  -30.00   0.00 180.00  120
  3  ω    -30.00  30.00   0.50    6.00    --   30.00   0.00 180.00  120
  4  ω    -30.00  30.00   0.50    6.00    --   30.00   0.00   0.00  120
  5  ω    -15.49  17.01   0.50    6.00    --   30.00  39.49 -12.99   65
  6  ω    -15.49  17.01   0.50    6.00    --   30.00  39.49 167.01   65
  7  ω    -42.99  17.01   0.50    6.00    --  -30.00  39.49 -12.99  120
  8  ω    -42.99  17.01   0.50    6.00    --  -30.00  39.49 167.01  120
  9  ω    -58.98   1.02   0.50    6.00    --  -30.00  81.49 151.02  120
 10  ω    -58.98   1.02   0.50    6.00    --  -30.00  81.49 -28.98  120
 11  ω    -36.48   1.02   0.50    6.00    --   15.00  81.49 -28.98   75
 12  ω    -36.48   1.02   0.50    6.00    --   15.00  81.49 151.02   75
 13  ω    -67.05 -27.05   0.50    6.00    --   15.00 134.76 122.95   80
 14  ω    -67.05 -27.05   0.50    6.00    --   15.00 134.76 -57.05   80
 15  ω    -87.05 -27.05   0.50    6.00    --  -30.00 134.76 -57.05  120
 16  ω    -87.05 -27.05   0.50    6.00    --  -30.00 134.76 122.95  120
 17  φ    -30.00  30.00   0.50    6.00   0.00 -30.00   0.00    --   120
 18  φ    -30.00  30.00   0.50    6.00   0.00  30.00   0.00    --   120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 0.16(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                287
_reflns_number_total             550
_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 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'PROGRAM:BIS 8.5.1.2 Release/2023-09-07 && APEX6 2024.9-0                        '
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_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         0.186
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.06(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   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         550
_refine_ls_number_restraints     506
_refine_ls_R_factor_all          0.1579
_refine_ls_R_factor_gt           0.0852
_refine_ls_restrained_S_all      0.741
_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)+(0.1609P)²+0.7480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2083
_refine_ls_wR_factor_ref         0.2874
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C18-C19A \\sim C19B-C18 \\sim C18-C17
 with sigma of 0.02
 C6-C7 \\sim C7-C8 \\sim C8-C9 \\sim C4-C9 \\sim C5-C4 \\sim C5-C6
 with sigma of 0.02
2. Rigid bond restraints
 C12, O2, C2, N1, C3, C13, C1, C4, C14, O1, C5, C9, C11, C15, C6, C10, C8, C16,
  C7, C17, C18, C19B, C19A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C12 \\sim O2 \\sim C2 \\sim N1 \\sim C3 \\sim C13 \\sim C1 \\sim C4 \\sim C14
\\sim O1 \\sim C5 \\sim C9 \\sim C11 \\sim C15 \\sim C6 \\sim C10 \\sim C8
\\sim C16 \\sim C7 \\sim C17 \\sim C18 \\sim C19B \\sim C19A: 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(C5) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C2)
\\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C1) \\sim Ueq: with
sigma of 0.1 and sigma for terminal atoms of 0.2
4. Rigid body (RIGU) restrains
 C12, O2, C2, N1, C3, C13, C1, C4, C14, O1, C5, C9, C11, C15, C6, C10, C8, C16,
  C7, C17, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H18C)=Sof(H18D)=Sof(C19B)=Sof(H19D)=Sof(H19E)=Sof(H19F)=1-FVAR(1)
 Sof(H18A)=Sof(H18B)=Sof(C19A)=Sof(H19A)=Sof(H19B)=Sof(H19C)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C18(H18C,H18D)
6.b Me refined with riding coordinates:
 C19A(H19A,H19B,H19C), C19B(H19D,H19E,H19F)
6.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C6(H6), C11(H11), C7(H7)
;
_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 1.0120(15) 0.0927(11) 0.3845(16) 0.074(13) Uani 1 1 d . U . . .
O1 O 0.668(3) 0.5445(18) 0.224(3) 0.080(10) Uani 1 1 d . U . . .
N1 N 0.840(3) 0.3165(19) 0.301(3) 0.065(9) Uani 1 1 d . U . . .
C5 C 0.437(3) 0.5070(18) 0.3312(18) 0.052(9) Uani 1 1 d D U . . .
C4 C 0.424(3) 0.414(2) 0.4005(16) 0.046(9) Uani 1 1 d D U . . .
C10 C 0.210(2) 0.3564(17) 0.519(3) 0.040(9) Uani 1 1 d . U . . .
C3 C 0.625(3) 0.269(2) 0.418(3) 0.060(9) Uani 1 1 d . U . . .
C8 C 0.018(3) 0.6005(18) 0.4315(18) 0.050(10) Uani 1 1 d D U . . .
C13 C 1.042(3) 0.259(2) 0.252(3) 0.069(10) Uani 1 1 d . U . . .
H6 H 1.214919 0.205196 0.277194 0.083 Uiso 1 1 calc R U . . .
H5 H 1.087646 0.352907 0.216796 0.083 Uiso 1 1 calc R U . . .
C9 C 0.212(3) 0.4551(19) 0.449(2) 0.046(9) Uani 1 1 d D U . . .
C14 C 0.922(3) 0.142(2) 0.215(3) 0.078(12) Uani 1 1 d . U . . .
H7 H 0.756149 0.199170 0.187432 0.094 Uiso 1 1 calc R U . . .
H8 H 0.861473 0.054003 0.250816 0.094 Uiso 1 1 calc R U . . .
C12 C 0.617(3) 0.1781(19) 0.494(3) 0.051(9) Uani 1 1 d . U . . .
H4 H 0.759333 0.090813 0.510833 0.061 Uiso 1 1 calc R U . . .
C6 C 0.245(2) 0.6520(17) 0.312(2) 0.062(10) Uani 1 1 d D U . . .
H1 H 0.257942 0.722921 0.268306 0.074 Uiso 1 1 calc R U . . .
C11 C 0.4146(19) 0.2190(15) 0.537(2) 0.049(9) Uani 1 1 d . U . . .
H3 H 0.407701 0.153045 0.582416 0.059 Uiso 1 1 calc R U . . .
C2 C 0.836(3) 0.223(2) 0.372(3) 0.059(9) Uani 1 1 d . U . . .
C7 C 0.029(3) 0.688(2) 0.3609(16) 0.048(10) Uani 1 1 d D U . . .
H2 H -0.114850 0.774407 0.345305 0.057 Uiso 1 1 calc R U . . .
C15 C 1.139(3) 0.063(2) 0.165(3) 0.079(12) Uani 1 1 d . U . . .
H9 H 1.191344 0.150051 0.127380 0.095 Uiso 1 1 calc R U . . .
H10 H 1.308865 0.010706 0.191803 0.095 Uiso 1 1 calc R U . . .
C1 C 0.651(5) 0.468(3) 0.275(3) 0.054(9) Uani 1 1 d . U . . .
C16 C 1.026(3) -0.0604(19) 0.131(2) 0.063(13) Uani 1 1 d . U . . .
H11 H 0.867325 -0.005994 0.100244 0.075 Uiso 1 1 calc R U . . .
H12 H 0.956509 -0.141714 0.168245 0.075 Uiso 1 1 calc R U . . .
C17 C 1.243(3) -0.148(2) 0.088(3) 0.076(15) Uani 1 1 d D U . . .
H13 H 1.306496 -0.066898 0.050139 0.091 Uiso 1 1 calc R U . . .
H14 H 1.406005 -0.197295 0.118872 0.091 Uiso 1 1 calc R U . . .
C18 C 1.146(4) -0.277(3) 0.057(3) 0.102(18) Uani 1 1 d D U . . .
H15A H 0.952847 -0.242169 0.039417 0.123 Uiso 0.51(5) 1 calc R U P A 1
H16A H 1.263424 -0.296720 0.016251 0.123 Uiso 0.51(5) 1 calc R U P A 1
H16B H 1.036432 -0.336077 0.093521 0.123 Uiso 0.49(5) 1 calc R U P A 2
H15B H 1.011546 -0.219272 0.019549 0.123 Uiso 0.49(5) 1 calc R U P A 2
C19A C 1.161(12) -0.427(5) 0.109(4) 0.13(3) Uani 0.51(5) 1 d D U P A 1
H18A H 1.095792 -0.512150 0.087106 0.189 Uiso 0.51(5) 1 calc R U P A 1
H19A H 1.352715 -0.462754 0.125062 0.189 Uiso 0.51(5) 1 calc R U P A 1
H17A H 1.042792 -0.408318 0.148179 0.189 Uiso 0.51(5) 1 calc R U P A 1
C19B C 1.311(13) -0.405(7) 0.026(8) 0.16(3) Uani 0.49(5) 1 d D U P A 2
H18B H 1.186568 -0.472002 0.009145 0.242 Uiso 0.49(5) 1 calc R U P A 2
H17B H 1.414905 -0.354185 -0.013896 0.242 Uiso 0.49(5) 1 calc R U P A 2
H19B H 1.440101 -0.472446 0.060998 0.242 Uiso 0.49(5) 1 calc R U P A 2


_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 C2 1.26(2) . ?
O1 C1 1.07(7) . ?
N1 C13 1.43(4) . ?
N1 C2 1.43(7) . ?
N1 C1 1.45(3) . ?
C5 C4 1.40(2) . ?
C5 C6 1.397(17) . ?
C5 C1 1.52(5) . ?
C4 C3 1.42(3) . ?
C4 C9 1.41(2) . ?
C10 C8 1.49(4) 2_566 ?
C10 C9 1.42(6) . ?
C10 C11 1.385(19) . ?
C3 C12 1.50(7) . ?
C3 C2 1.40(4) . ?
C8 C9 1.403(17) . ?
C8 C7 1.41(2) . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.48(3) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C15 1.57(4) . ?
C12 H4 0.9300 . ?
C12 C11 1.31(4) . ?
C6 H1 0.9300 . ?
C6 C7 1.42(2) . ?
C11 H3 0.9300 . ?
C7 H2 0.9300 . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.46(3) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C17 1.51(3) . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C18 1.45(3) . ?
C18 H15A 0.9700 . ?
C18 H16A 0.9700 . ?
C18 H16B 0.9700 . ?
C18 H15B 0.9700 . ?
C18 C19A 1.43(4) . ?
C18 C19B 1.44(4) . ?
C19A H18A 0.9600 . ?
C19A H19A 0.9600 . ?
C19A H17A 0.9600 . ?
C19B H18B 0.9600 . ?
C19B H17B 0.9600 . ?
C19B H19B 0.9600 . ?

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
C13 N1 C2 119(2) . . ?
C13 N1 C1 117(3) . . ?
C2 N1 C1 124(3) . . ?
C4 C5 C1 126(2) . . ?
C6 C5 C4 118(2) . . ?
C6 C5 C1 116(2) . . ?
C5 C4 C3 117(2) . . ?
C5 C4 C9 122(2) . . ?
C9 C4 C3 121(3) . . ?
C9 C10 C8 119.0(16) . 2_566 ?
C11 C10 C8 122(3) . 2_566 ?
C11 C10 C9 119(3) . . ?
C4 C3 C12 115(3) . . ?
C2 C3 C4 123(4) . . ?
C2 C3 C12 121(2) . . ?
C9 C8 C10 121(2) . 2_566 ?
C9 C8 C7 116(2) . . ?
C7 C8 C10 122.7(19) . 2_566 ?
N1 C13 H6 109.8 . . ?
N1 C13 H5 109.8 . . ?
N1 C13 C14 109.2(15) . . ?
H6 C13 H5 108.3 . . ?
C14 C13 H6 109.8 . . ?
C14 C13 H5 109.8 . . ?
C4 C9 C10 119.8(18) . . ?
C8 C9 C4 120(2) . . ?
C8 C9 C10 120(2) . . ?
C13 C14 H7 109.1 . . ?
C13 C14 H8 109.1 . . ?
C13 C14 C15 112.4(13) . . ?
H7 C14 H8 107.9 . . ?
C15 C14 H7 109.1 . . ?
C15 C14 H8 109.1 . . ?
C3 C12 H4 119.3 . . ?
C11 C12 C3 121.4(19) . . ?
C11 C12 H4 119.3 . . ?
C5 C6 H1 121.1 . . ?
C5 C6 C7 118(2) . . ?
C7 C6 H1 121.1 . . ?
C10 C11 H3 118.7 . . ?
C12 C11 C10 123(3) . . ?
C12 C11 H3 118.7 . . ?
O2 C2 N1 115(3) . . ?
O2 C2 C3 125(4) . . ?
C3 C2 N1 119(2) . . ?
C8 C7 C6 125(2) . . ?
C8 C7 H2 117.7 . . ?
C6 C7 H2 117.7 . . ?
C14 C15 H9 109.1 . . ?
C14 C15 H10 109.1 . . ?
H9 C15 H10 107.8 . . ?
C16 C15 C14 112.6(14) . . ?
C16 C15 H9 109.1 . . ?
C16 C15 H10 109.1 . . ?
O1 C1 N1 124(4) . . ?
O1 C1 C5 125(3) . . ?
N1 C1 C5 111(4) . . ?
C15 C16 H11 109.0 . . ?
C15 C16 H12 109.0 . . ?
C15 C16 C17 112.8(12) . . ?
H11 C16 H12 107.8 . . ?
C17 C16 H11 109.0 . . ?
C17 C16 H12 109.0 . . ?
C16 C17 H13 108.5 . . ?
C16 C17 H14 108.5 . . ?
H13 C17 H14 107.5 . . ?
C18 C17 C16 115.1(16) . . ?
C18 C17 H13 108.5 . . ?
C18 C17 H14 108.5 . . ?
C17 C18 H15A 109.6 . . ?
C17 C18 H16A 109.6 . . ?
C17 C18 H16B 105.1 . . ?
C17 C18 H15B 105.1 . . ?
H15A C18 H16A 108.1 . . ?
H16B C18 H15B 105.9 . . ?
C19A C18 C17 110(4) . . ?
C19A C18 H15A 109.6 . . ?
C19A C18 H16A 109.6 . . ?
C19B C18 C17 129(3) . . ?
C19B C18 H16B 105.1 . . ?
C19B C18 H15B 105.1 . . ?
C18 C19A H18A 109.5 . . ?
C18 C19A H19A 109.5 . . ?
C18 C19A H17A 109.5 . . ?
H18A C19A H19A 109.5 . . ?
H18A C19A H17A 109.5 . . ?
H19A C19A H17A 109.5 . . ?
C18 C19B H18B 109.5 . . ?
C18 C19B H17B 109.5 . . ?
C18 C19B H19B 109.5 . . ?
H18B C19B H17B 109.5 . . ?
H18B C19B H19B 109.5 . . ?
H17B C19B H19B 109.5 . . ?

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
N1 C13 C14 C15 -176(3) . . . . ?
C5 C4 C3 C12 176(2) . . . . ?
C5 C4 C3 C2 3(3) . . . . ?
C5 C4 C9 C10 -180(2) . . . . ?
C5 C4 C9 C8 -5(3) . . . . ?
C5 C6 C7 C8 9(3) . . . . ?
C4 C5 C6 C7 -6(2) . . . . ?
C4 C5 C1 O1 -176(4) . . . . ?
C4 C5 C1 N1 2(4) . . . . ?
C4 C3 C12 C11 8(4) . . . . ?
C4 C3 C2 O2 -177(3) . . . . ?
C4 C3 C2 N1 -5(4) . . . . ?
C10 C8 C9 C4 178.5(15) 2_566 . . . ?
C10 C8 C9 C10 -7(4) 2_566 . . . ?
C10 C8 C7 C6 179.2(14) 2_566 . . . ?
C3 C4 C9 C10 4(3) . . . . ?
C3 C4 C9 C8 179(2) . . . . ?
C3 C12 C11 C10 -6(4) . . . . ?
C8 C10 C9 C4 -178.6(13) 2_566 . . . ?
C8 C10 C9 C8 7(4) 2_566 . . . ?
C8 C10 C11 C12 180(2) 2_566 . . . ?
C13 N1 C2 O2 -2(4) . . . . ?
C13 N1 C2 C3 -174.6(18) . . . . ?
C13 N1 C1 O1 -6(6) . . . . ?
C13 N1 C1 C5 176.1(19) . . . . ?
C13 C14 C15 C16 177(3) . . . . ?
C9 C4 C3 C12 -7(4) . . . . ?
C9 C4 C3 C2 179(2) . . . . ?
C9 C10 C11 C12 2(4) . . . . ?
C9 C8 C7 C6 -10(3) . . . . ?
C14 C15 C16 C17 -174(2) . . . . ?
C12 C3 C2 O2 10(4) . . . . ?
C12 C3 C2 N1 -178(3) . . . . ?
C6 C5 C4 C3 -179.0(17) . . . . ?
C6 C5 C4 C9 5(2) . . . . ?
C6 C5 C1 O1 2(6) . . . . ?
C6 C5 C1 N1 180(2) . . . . ?
C11 C10 C9 C4 -1(4) . . . . ?
C11 C10 C9 C8 -175.7(14) . . . . ?
C2 N1 C13 C14 87(3) . . . . ?
C2 N1 C1 O1 174(5) . . . . ?
C2 N1 C1 C5 -4(4) . . . . ?
C2 C3 C12 C11 -178.2(16) . . . . ?
C7 C8 C9 C4 7(3) . . . . ?
C7 C8 C9 C10 -178(2) . . . . ?
C15 C16 C17 C18 177(3) . . . . ?
C1 N1 C13 C14 -93(3) . . . . ?
C1 N1 C2 O2 179(2) . . . . ?
C1 N1 C2 C3 6(5) . . . . ?
C1 C5 C4 C3 -2(3) . . . . ?
C1 C5 C4 C9 -178.0(19) . . . . ?
C1 C5 C6 C7 176.0(19) . . . . ?
C16 C17 C18 C19A -82(4) . . . . ?
C16 C17 C18 C19B -166(6) . . . . ?

_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
- Detector area 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_PDI_C7_1_84GPa
_database_code_depnum_ccdc_archive 'CCDC 2493908'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C7_1_84GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.311 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C7_1_84GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.51 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT910_PDI_C7_1_84GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         74 Note  

RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT340_PDI_C7_1_84GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.0106 Ang.  
RESPONSE: These data come from high-pressure experiment and part of the 
reflections can not be collected, affecting bond precision. In addition, 
despite multiple attempts to grow better diffracting crystals, it was not 
successful.
;
_vrf_PLAT911_PDI_C7_1_84GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        1027 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-02-14

_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        N,N-Diheptyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_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 -0.0004 0.0007 '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 -0.0003 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0008 0.0027 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.5578(2)
_cell_length_b                   8.2194(4)
_cell_length_c                   18.170(4)
_cell_angle_alpha                79.124(9)
_cell_angle_beta                 86.465(8)
_cell_angle_gamma                84.599(4)
_cell_volume                     664.82(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    743
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.0150
_cell_measurement_theta_min      5.2940
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.995
_exptl_absorpt_coefficient_mu    0.050
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.094
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.311
_diffrn_reflns_Laue_measured_fraction_max 0.188
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3177
_diffrn_reflns_point_group_measured_fraction_full 0.311
_diffrn_reflns_point_group_measured_fraction_max 0.188
_diffrn_reflns_theta_full        17.166
_diffrn_reflns_theta_max         23.354
_diffrn_reflns_theta_min         5.287
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.311
_diffrn_measured_fraction_theta_max 0.188
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     15.00 100.00   0.25    1.00  57.05   0.00-134.76    --   340
  2  φ     15.00 100.00   0.25    1.00  57.05   0.00-134.76    --   340
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.4919
_diffrn_source                   synchrotron
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 1.84(2) GPa.
Pressure was determined by monitoring the shift of 
the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                729
_reflns_number_total             1102
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.240
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         1102
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0859
_refine_ls_restrained_S_all      1.094
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2378
_refine_ls_wR_factor_ref         0.2730
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq,
Uanis(N1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O2) \\sim
Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq,
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.04
3.a Secondary CH2 refined with riding coordinates:
 C15(H9,H10), C18(H15,H16), C13(H6,H5), C17(H13,H14), C16(H11,H12), C14(H7,H8)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H3), C6(H1), C12(H4), C7(H2)
3.c Idealised Me refined as rotating group:
 C19(H17,H18,H19)
;
_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 1.0050(6) 0.4876(4) 0.6181(4) 0.073(4) Uani 1 1 d . U . . .
O2 O 0.6636(8) 0.7992(6) 0.7905(7) 0.068(6) Uani 1 1 d . U . . .
C5 C 0.6210(7) 0.6959(5) 0.5790(7) 0.036(3) Uani 1 1 d . U . . .
C9 C 0.2113(7) 0.9113(5) 0.5490(6) 0.036(3) Uani 1 1 d . U . . .
C8 C 0.2033(7) 0.8704(5) 0.4796(6) 0.037(3) Uani 1 1 d . U . . .
C1 C 0.8350(7) 0.6039(5) 0.6334(6) 0.041(3) Uani 1 1 d . U . . .
N1 N 0.8420(6) 0.6475(5) 0.7031(6) 0.045(3) Uani 1 1 d . U . . .
C11 C 0.0386(8) 1.0760(6) 0.6453(7) 0.044(3) Uani 1 1 d . U . . .
H3 H -0.086511 1.161308 0.660054 0.053 Uiso 1 1 calc R U . . .
C6 C 0.6171(7) 0.6640(6) 0.5077(7) 0.043(3) Uani 1 1 d . U . . .
H1 H 0.755293 0.584476 0.492884 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4348(7) 0.8626(6) 0.6723(7) 0.042(3) Uani 1 1 d . U . . .
C4 C 0.4205(7) 0.8233(5) 0.6027(6) 0.037(3) Uani 1 1 d . U . . .
C10 C 0.0120(7) 1.0397(5) 0.5743(6) 0.038(3) Uani 1 1 d . U . . .
C15 C 1.1137(8) 0.2662(6) 0.8469(7) 0.053(3) Uani 1 1 d . U . . .
H9 H 1.290800 0.245884 0.816367 0.064 Uiso 1 1 calc R U . . .
H10 H 1.170304 0.309835 0.889471 0.064 Uiso 1 1 calc R U . . .
C12 C 0.2451(8) 0.9898(5) 0.6954(6) 0.045(3) Uani 1 1 d . U . . .
H4 H 0.256436 1.016012 0.742654 0.054 Uiso 1 1 calc R U . . .
C7 C 0.4097(7) 0.7482(4) 0.4561(6) 0.040(3) Uani 1 1 d . U . . .
H2 H 0.408418 0.724301 0.408109 0.048 Uiso 1 1 calc R U . . .
C18 C 1.0680(9) -0.1980(5) 0.9347(7) 0.053(4) Uani 1 1 d . U . . .
H15 H 0.983611 -0.222232 0.890628 0.064 Uiso 1 1 calc R U . . .
H16 H 0.909628 -0.190332 0.972390 0.064 Uiso 1 1 calc R U . . .
C13 C 1.0408(7) 0.5459(5) 0.7572(6) 0.037(3) Uani 1 1 d . U . . .
H6 H 1.095374 0.612749 0.792003 0.044 Uiso 1 1 calc R U . . .
H5 H 1.219377 0.509789 0.730770 0.044 Uiso 1 1 calc R U . . .
C17 C 1.1988(8) -0.0350(5) 0.9146(7) 0.055(3) Uani 1 1 d . U . . .
H13 H 1.373332 -0.047000 0.882096 0.066 Uiso 1 1 calc R U . . .
H14 H 1.259727 -0.004010 0.959923 0.066 Uiso 1 1 calc R U . . .
C16 C 0.9795(8) 0.1077(5) 0.8741(6) 0.047(3) Uani 1 1 d . U . . .
H11 H 0.902804 0.071449 0.831754 0.057 Uiso 1 1 calc R U . . .
H12 H 0.814330 0.126887 0.908543 0.057 Uiso 1 1 calc R U . . .
C14 C 0.9002(8) 0.3957(6) 0.8004(7) 0.049(4) Uani 1 1 d . U . . .
H7 H 0.809694 0.342506 0.765218 0.059 Uiso 1 1 calc R U . . .
H8 H 0.744411 0.432593 0.833786 0.059 Uiso 1 1 calc R U . . .
C19 C 1.2938(10) -0.3403(6) 0.9647(8) 0.084(7) Uani 1 1 d . U . . .
H17 H 1.452978 -0.347279 0.927938 0.125 Uiso 1 1 calc R U . . .
H18 H 1.201323 -0.442912 0.974904 0.125 Uiso 1 1 calc R U . . .
H19 H 1.369398 -0.320321 1.010026 0.125 Uiso 1 1 calc R U . . .
C2 C 0.6499(8) 0.7728(7) 0.7276(8) 0.038(4) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.235(5) . ?
O2 C2 1.208(17) . ?
C5 C1 1.482(11) . ?
C5 C6 1.371(16) . ?
C5 C4 1.435(6) . ?
C9 C8 1.368(14) . ?
C9 C4 1.449(11) . ?
C9 C10 1.449(6) . ?
C8 C10 1.475(11) 2_576 ?
C8 C7 1.418(6) . ?
C1 N1 1.383(14) . ?
N1 C13 1.463(10) . ?
N1 C2 1.407(7) . ?
C11 H3 0.9300 . ?
C11 C10 1.394(15) . ?
C11 C12 1.397(12) . ?
C6 H1 0.9300 . ?
C6 C7 1.412(11) . ?
C3 C4 1.371(16) . ?
C3 C12 1.402(7) . ?
C3 C2 1.490(13) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.478(7) . ?
C15 C14 1.537(10) . ?
C12 H4 0.9300 . ?
C7 H2 0.9300 . ?
C18 H15 0.9700 . ?
C18 H16 0.9700 . ?
C18 C17 1.491(7) . ?
C18 C19 1.525(8) . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.507(8) . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C16 1.569(9) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C19 H17 0.9600 . ?
C19 H18 0.9600 . ?
C19 H19 0.9600 . ?

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
C6 C5 C1 121.6(5) . . ?
C6 C5 C4 120.5(8) . . ?
C4 C5 C1 117.8(9) . . ?
C8 C9 C4 120.8(4) . . ?
C8 C9 C10 123.2(7) . . ?
C10 C9 C4 116.0(8) . . ?
C9 C8 C10 120.2(4) . 2_576 ?
C9 C8 C7 121.4(7) . . ?
C7 C8 C10 118.3(8) . 2_576 ?
O1 C1 C5 121.3(9) . . ?
O1 C1 N1 119.2(7) . . ?
N1 C1 C5 119.4(5) . . ?
C1 N1 C13 117.7(4) . . ?
C1 N1 C2 124.0(8) . . ?
C2 N1 C13 118.0(9) . . ?
C10 C11 H3 118.6 . . ?
C10 C11 C12 122.8(4) . . ?
C12 C11 H3 118.6 . . ?
C5 C6 H1 119.0 . . ?
C5 C6 C7 122.0(4) . . ?
C7 C6 H1 119.0 . . ?
C4 C3 C12 121.4(8) . . ?
C4 C3 C2 122.2(5) . . ?
C12 C3 C2 116.5(10) . . ?
C5 C4 C9 117.2(9) . . ?
C3 C4 C5 120.8(7) . . ?
C3 C4 C9 122.0(4) . . ?
C9 C10 C8 116.6(8) . 2_576 ?
C11 C10 C9 119.6(7) . . ?
C11 C10 C8 123.8(4) . 2_576 ?
H9 C15 H10 107.9 . . ?
C16 C15 H9 109.3 . . ?
C16 C15 H10 109.3 . . ?
C16 C15 C14 111.7(4) . . ?
C14 C15 H9 109.3 . . ?
C14 C15 H10 109.3 . . ?
C11 C12 C3 118.2(9) . . ?
C11 C12 H4 120.9 . . ?
C3 C12 H4 120.9 . . ?
C8 C7 H2 121.0 . . ?
C6 C7 C8 118.0(8) . . ?
C6 C7 H2 121.0 . . ?
H15 C18 H16 107.8 . . ?
C17 C18 H15 109.1 . . ?
C17 C18 H16 109.1 . . ?
C17 C18 C19 112.6(4) . . ?
C19 C18 H15 109.1 . . ?
C19 C18 H16 109.1 . . ?
N1 C13 H6 109.3 . . ?
N1 C13 H5 109.3 . . ?
N1 C13 C14 111.8(4) . . ?
H6 C13 H5 107.9 . . ?
C14 C13 H6 109.3 . . ?
C14 C13 H5 109.3 . . ?
C18 C17 H13 109.0 . . ?
C18 C17 H14 109.0 . . ?
C18 C17 C16 113.0(4) . . ?
H13 C17 H14 107.8 . . ?
C16 C17 H13 109.0 . . ?
C16 C17 H14 109.0 . . ?
C15 C16 C17 113.8(4) . . ?
C15 C16 H11 108.8 . . ?
C15 C16 H12 108.8 . . ?
C17 C16 H11 108.8 . . ?
C17 C16 H12 108.8 . . ?
H11 C16 H12 107.7 . . ?
C15 C14 H7 108.6 . . ?
C15 C14 H8 108.6 . . ?
C13 C14 C15 114.6(4) . . ?
C13 C14 H7 108.6 . . ?
C13 C14 H8 108.6 . . ?
H7 C14 H8 107.6 . . ?
C18 C19 H17 109.5 . . ?
C18 C19 H18 109.5 . . ?
C18 C19 H19 109.5 . . ?
H17 C19 H18 109.5 . . ?
H17 C19 H19 109.5 . . ?
H18 C19 H19 109.5 . . ?
O2 C2 N1 119.8(9) . . ?
O2 C2 C3 124.5(6) . . ?
N1 C2 C3 115.7(10) . . ?

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 N1 C13 -3.6(9) . . . . ?
O1 C1 N1 C2 -177.1(5) . . . . ?
C5 C1 N1 C13 175.5(4) . . . . ?
C5 C1 N1 C2 2.0(10) . . . . ?
C5 C6 C7 C8 0.8(8) . . . . ?
C9 C8 C7 C6 2.7(8) . . . . ?
C8 C9 C4 C5 1.5(8) . . . . ?
C8 C9 C4 C3 179.5(6) . . . . ?
C8 C9 C10 C8 -1.0(9) . . . 2_576 ?
C8 C9 C10 C11 -178.7(6) . . . . ?
C1 C5 C6 C7 178.5(4) . . . . ?
C1 C5 C4 C9 -179.6(4) . . . . ?
C1 C5 C4 C3 2.5(9) . . . . ?
C1 N1 C13 C14 -85.2(8) . . . . ?
C1 N1 C2 O2 177.4(7) . . . . ?
C1 N1 C2 C3 -1.4(10) . . . . ?
N1 C13 C14 C15 168.8(7) . . . . ?
C6 C5 C1 O1 -4.8(8) . . . . ?
C6 C5 C1 N1 176.1(6) . . . . ?
C6 C5 C4 C9 1.9(9) . . . . ?
C6 C5 C4 C3 -176.1(6) . . . . ?
C4 C5 C1 O1 176.7(5) . . . . ?
C4 C5 C1 N1 -2.4(8) . . . . ?
C4 C5 C6 C7 -3.0(9) . . . . ?
C4 C9 C8 C10 179.6(4) . . . 2_576 ?
C4 C9 C8 C7 -3.9(9) . . . . ?
C4 C9 C10 C8 -179.6(4) . . . 2_576 ?
C4 C9 C10 C11 2.7(8) . . . . ?
C4 C3 C12 C11 0.2(9) . . . . ?
C4 C3 C2 O2 -177.3(8) . . . . ?
C4 C3 C2 N1 1.4(9) . . . . ?
C10 C9 C8 C10 1.1(9) . . . 2_576 ?
C10 C9 C8 C7 177.6(4) . . . . ?
C10 C9 C4 C5 -179.8(5) . . . . ?
C10 C9 C4 C3 -1.9(8) . . . . ?
C10 C8 C7 C6 179.3(4) 2_576 . . . ?
C10 C11 C12 C3 0.7(9) . . . . ?
C12 C11 C10 C9 -2.2(10) . . . . ?
C12 C11 C10 C8 -179.7(4) . . . 2_576 ?
C12 C3 C4 C5 178.3(5) . . . . ?
C12 C3 C4 C9 0.5(10) . . . . ?
C12 C3 C2 O2 2.4(11) . . . . ?
C12 C3 C2 N1 -178.9(5) . . . . ?
C18 C17 C16 C15 -174.2(8) . . . . ?
C13 N1 C2 O2 3.8(10) . . . . ?
C13 N1 C2 C3 -174.9(4) . . . . ?
C16 C15 C14 C13 -167.5(8) . . . . ?
C14 C15 C16 C17 173.9(8) . . . . ?
C19 C18 C17 C16 172.5(10) . . . . ?
C2 N1 C13 C14 88.8(7) . . . . ?
C2 C3 C4 C5 -2.0(10) . . . . ?
C2 C3 C4 C9 -179.9(4) . . . . ?
C2 C3 C12 C11 -179.5(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_PDI_C7_375K
_database_code_depnum_ccdc_archive 'CCDC 2493909'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT088_PDI_C7_375K         
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.64 Note
RESPONSE: These data come from high-temperature studies, and the 
poor data quality is related to the progressive increase in thermal 
motions and low symmetry. 
;
_vrf_THETM01_PDI_C7_375K         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.4717
RESPONSE: Due to the low symmetry some of the data can not be collected.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-03-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        'N,N Diheptyl 3,4,9,10 perylenedicarboximide'
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8295(13)
_cell_length_b                   8.364(2)
_cell_length_c                   19.338(5)
_cell_angle_alpha                79.563(15)
_cell_angle_beta                 88.468(17)
_cell_angle_gamma                81.572(15)
_cell_volume                     759.9(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1430
_cell_measurement_temperature    375
_cell_measurement_theta_max      19.358
_cell_measurement_theta_min      2.502
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7444
_exptl_absorpt_correction_T_min  0.5259
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1639 before and 0.1102 after correction.
The Ratio of minimum to maximum transmission is 0.7065.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1496
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18169
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        19.587
_diffrn_reflns_theta_max         19.587
_diffrn_reflns_theta_min         2.142
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          
;
 Data were collected at high temperature of 375 K.
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                862
_reflns_number_total             1321
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.142
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1321
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.063
_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)+(0.0875P)²+0.0865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1694
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C19A-C18 \\sim C20B-C18
 with sigma of 0.02
2. Rigid body (RIGU) restrains
 C19A, C18, C20B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(H15B)=Sof(H16B)=Sof(C20B)=Sof(H18B)=Sof(H19B)=Sof(H17B)=1-FVAR(1)
 Sof(H16A)=Sof(H15A)=Sof(C19A)=Sof(H17A)=Sof(H18A)=Sof(H19A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C13(H5,H6), C14(H7,H8), C15(H9,H10), C16(H11,H12), C17(H13,H14), C18(H15B,
 H16B), C18(H16A,H15A)
4.b Me refined with riding coordinates:
 C19A(H17A,H18A,H19A), C20B(H18B,H19B,H17B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H1), C12(H4), C7(H2), C11(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0096(6) 0.0909(3) 0.38851(14) 0.0744(9) Uani 1 1 d . . . . .
O2 O 0.6731(6) 0.5356(4) 0.22753(18) 0.0894(11) Uani 1 1 d . . . . .
N1 N 0.8427(6) 0.3138(4) 0.30767(19) 0.0578(9) Uani 1 1 d . . . . .
C3 C 0.4390(7) 0.5035(5) 0.3365(2) 0.0492(10) Uani 1 1 d . . . . .
C4 C 0.4232(7) 0.4089(4) 0.4038(2) 0.0450(10) Uani 1 1 d . . . . .
C8 C 0.2061(7) 0.3560(4) 0.5200(2) 0.0442(10) Uani 1 1 d . . . . .
C5 C 0.6241(7) 0.2681(5) 0.4236(2) 0.0472(10) Uani 1 1 d . . . . .
C10 C 0.0129(7) 0.5975(4) 0.4307(2) 0.0451(10) Uani 1 1 d . . . . .
C13 C 1.0463(8) 0.2569(4) 0.2567(2) 0.0685(12) Uani 1 1 d . . . . .
H5 H 1.214676 0.199699 0.281345 0.082 Uiso 1 1 calc R U . . .
H6 H 1.096519 0.351124 0.224340 0.082 Uiso 1 1 calc R U . . .
C9 C 0.2127(7) 0.4548(4) 0.4514(2) 0.0432(10) Uani 1 1 d . . . . .
C14 C 0.9320(8) 0.1430(5) 0.2155(2) 0.0768(13) Uani 1 1 d . . . . .
H7 H 0.860712 0.056390 0.248337 0.092 Uiso 1 1 calc R U . . .
H8 H 0.776110 0.204448 0.187007 0.092 Uiso 1 1 calc R U . . .
C6 C 0.6146(7) 0.1785(4) 0.4901(3) 0.0547(11) Uani 1 1 d . . . . .
H1 H 0.749440 0.087393 0.503798 0.066 Uiso 1 1 calc R U . . .
C12 C 0.2474(8) 0.6418(5) 0.3180(2) 0.0609(11) Uani 1 1 d . . . . .
H4 H 0.256937 0.706048 0.273664 0.073 Uiso 1 1 calc R U . . .
C7 C 0.4071(8) 0.2209(4) 0.53776(19) 0.0522(11) Uani 1 1 d . . . . .
H2 H 0.404480 0.156732 0.582330 0.063 Uiso 1 1 calc R U . . .
C1 C 0.8385(8) 0.2158(5) 0.3740(3) 0.0603(12) Uani 1 1 d . . . . .
C11 C 0.0398(7) 0.6874(4) 0.3642(2) 0.0579(11) Uani 1 1 d . . . . .
H3 H -0.086300 0.782294 0.349969 0.069 Uiso 1 1 calc R U . . .
C15 C 1.1430(8) 0.0662(5) 0.1686(2) 0.0835(14) Uani 1 1 d . . . . .
H9 H 1.305337 0.012028 0.196485 0.100 Uiso 1 1 calc R U . . .
H10 H 1.203422 0.152427 0.133430 0.100 Uiso 1 1 calc R U . . .
C2 C 0.6529(8) 0.4570(5) 0.2863(3) 0.0628(12) Uani 1 1 d . . . . .
C16 C 1.0353(9) -0.0584(5) 0.1313(2) 0.0872(14) Uani 1 1 d . . . . .
H11 H 0.965253 -0.141345 0.166367 0.105 Uiso 1 1 calc R U . . .
H12 H 0.879423 -0.002827 0.101399 0.105 Uiso 1 1 calc R U . . .
C17 C 1.2506(10) -0.1415(6) 0.0876(3) 0.1130(18) Uani 1 1 d . . . . .
H13 H 1.406016 -0.197041 0.117699 0.136 Uiso 1 1 calc R U . . .
H14 H 1.321195 -0.058185 0.052868 0.136 Uiso 1 1 calc R U . . .
C18 C 1.1482(15) -0.2644(8) 0.0502(4) 0.151(2) Uani 1 1 d D . . . .
H15B H 1.023461 -0.322902 0.082099 0.182 Uiso 0.489(14) 1 calc R U P A 2
H16B H 1.035455 -0.202856 0.010721 0.182 Uiso 0.489(14) 1 calc R U P A 2
H16A H 0.958332 -0.223347 0.033973 0.182 Uiso 0.511(14) 1 calc R U P A 1
H15A H 1.264485 -0.275670 0.009142 0.182 Uiso 0.511(14) 1 calc R U P A 1
C19A C 1.152(3) -0.4066(15) 0.0893(6) 0.121(5) Uani 0.511(14) 1 d D . P A 1
H17A H 1.085180 -0.480015 0.062933 0.181 Uiso 0.511(14) 1 calc R U P A 1
H18A H 1.340367 -0.449152 0.104633 0.181 Uiso 0.511(14) 1 calc R U P A 1
H19A H 1.034161 -0.396820 0.129469 0.181 Uiso 0.511(14) 1 calc R U P A 1
C20B C 1.334(3) -0.379(2) 0.0250(13) 0.222(13) Uani 0.489(14) 1 d D . P A 2
H18B H 1.233504 -0.447222 0.002784 0.332 Uiso 0.489(14) 1 calc R U P A 2
H19B H 1.455141 -0.325427 -0.008646 0.332 Uiso 0.489(14) 1 calc R U P A 2
H17B H 1.443072 -0.446218 0.063176 0.332 Uiso 0.489(14) 1 calc R U P A 2


_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(4) . ?
O2 C2 1.215(4) . ?
N1 C13 1.464(4) . ?
N1 C1 1.392(5) . ?
N1 C2 1.402(5) . ?
C3 C4 1.402(5) . ?
C3 C12 1.370(5) . ?
C3 C2 1.458(5) . ?
C4 C5 1.413(5) . ?
C4 C9 1.411(5) . ?
C8 C10 1.463(5) 2_566 ?
C8 C9 1.433(5) . ?
C8 C7 1.376(4) . ?
C5 C6 1.370(5) . ?
C5 C1 1.466(5) . ?
C10 C9 1.423(5) . ?
C10 C11 1.380(5) . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C13 C14 1.517(5) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C15 1.498(5) . ?
C6 H1 0.9300 . ?
C6 C7 1.394(5) . ?
C12 H4 0.9300 . ?
C12 C11 1.383(5) . ?
C7 H2 0.9300 . ?
C11 H3 0.9300 . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.525(5) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C17 1.495(5) . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C18 1.505(7) . ?
C18 H15B 0.9700 . ?
C18 H16B 0.9700 . ?
C18 H16A 0.9700 . ?
C18 H15A 0.9700 . ?
C18 C19A 1.287(9) . ?
C18 C20B 1.362(11) . ?
C19A H17A 0.9600 . ?
C19A H18A 0.9600 . ?
C19A H19A 0.9600 . ?
C20B H18B 0.9600 . ?
C20B H19B 0.9600 . ?
C20B H17B 0.9600 . ?

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 C13 117.5(3) . . ?
C1 N1 C2 123.5(4) . . ?
C2 N1 C13 118.9(4) . . ?
C4 C3 C2 121.4(4) . . ?
C12 C3 C4 118.7(4) . . ?
C12 C3 C2 119.9(4) . . ?
C3 C4 C5 118.9(4) . . ?
C3 C4 C9 120.6(4) . . ?
C9 C4 C5 120.6(4) . . ?
C9 C8 C10 119.0(3) . 2_566 ?
C7 C8 C10 121.9(4) . 2_566 ?
C7 C8 C9 119.1(4) . . ?
C4 C5 C1 121.2(4) . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 C1 119.9(4) . . ?
C9 C10 C8 119.6(3) . 2_566 ?
C11 C10 C8 123.1(4) . 2_566 ?
C11 C10 C9 117.3(4) . . ?
N1 C13 H5 109.2 . . ?
N1 C13 H6 109.2 . . ?
N1 C13 C14 111.9(3) . . ?
H5 C13 H6 107.9 . . ?
C14 C13 H5 109.2 . . ?
C14 C13 H6 109.2 . . ?
C4 C9 C8 118.8(3) . . ?
C4 C9 C10 119.8(4) . . ?
C10 C9 C8 121.4(3) . . ?
C13 C14 H7 108.8 . . ?
C13 C14 H8 108.8 . . ?
H7 C14 H8 107.7 . . ?
C15 C14 C13 114.0(3) . . ?
C15 C14 H7 108.8 . . ?
C15 C14 H8 108.8 . . ?
C5 C6 H1 119.3 . . ?
C5 C6 C7 121.4(3) . . ?
C7 C6 H1 119.3 . . ?
C3 C12 H4 119.5 . . ?
C3 C12 C11 121.1(4) . . ?
C11 C12 H4 119.5 . . ?
C8 C7 C6 121.2(4) . . ?
C8 C7 H2 119.4 . . ?
C6 C7 H2 119.4 . . ?
O1 C1 N1 119.7(4) . . ?
O1 C1 C5 122.9(4) . . ?
N1 C1 C5 117.4(4) . . ?
C10 C11 C12 122.5(3) . . ?
C10 C11 H3 118.8 . . ?
C12 C11 H3 118.8 . . ?
C14 C15 H9 108.7 . . ?
C14 C15 H10 108.7 . . ?
C14 C15 C16 114.1(3) . . ?
H9 C15 H10 107.6 . . ?
C16 C15 H9 108.7 . . ?
C16 C15 H10 108.7 . . ?
O2 C2 N1 119.1(4) . . ?
O2 C2 C3 123.3(4) . . ?
N1 C2 C3 117.6(4) . . ?
C15 C16 H11 108.7 . . ?
C15 C16 H12 108.7 . . ?
H11 C16 H12 107.6 . . ?
C17 C16 C15 114.0(4) . . ?
C17 C16 H11 108.7 . . ?
C17 C16 H12 108.7 . . ?
C16 C17 H13 108.5 . . ?
C16 C17 H14 108.5 . . ?
C16 C17 C18 114.9(5) . . ?
H13 C17 H14 107.5 . . ?
C18 C17 H13 108.5 . . ?
C18 C17 H14 108.5 . . ?
C17 C18 H15B 107.2 . . ?
C17 C18 H16B 107.2 . . ?
C17 C18 H16A 109.0 . . ?
C17 C18 H15A 109.0 . . ?
H15B C18 H16B 106.9 . . ?
H16A C18 H15A 107.8 . . ?
C19A C18 C17 112.9(8) . . ?
C19A C18 H16A 109.0 . . ?
C19A C18 H15A 109.0 . . ?
C20B C18 C17 120.4(8) . . ?
C20B C18 H15B 107.2 . . ?
C20B C18 H16B 107.2 . . ?
C18 C19A H17A 109.5 . . ?
C18 C19A H18A 109.5 . . ?
C18 C19A H19A 109.5 . . ?
H17A C19A H18A 109.5 . . ?
H17A C19A H19A 109.5 . . ?
H18A C19A H19A 109.5 . . ?
C18 C20B H18B 109.5 . . ?
C18 C20B H19B 109.5 . . ?
C18 C20B H17B 109.5 . . ?
H18B C20B H19B 109.5 . . ?
H18B C20B H17B 109.5 . . ?
H19B C20B H17B 109.5 . . ?

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
N1 C13 C14 C15 -173.4(3) . . . . ?
C3 C4 C5 C6 177.9(3) . . . . ?
C3 C4 C5 C1 -3.0(5) . . . . ?
C3 C4 C9 C8 -179.1(3) . . . . ?
C3 C4 C9 C10 0.7(5) . . . . ?
C3 C12 C11 C10 -0.3(5) . . . . ?
C4 C3 C12 C11 -0.6(5) . . . . ?
C4 C3 C2 O2 179.9(3) . . . . ?
C4 C3 C2 N1 0.0(5) . . . . ?
C4 C5 C6 C7 1.7(5) . . . . ?
C4 C5 C1 O1 -177.2(3) . . . . ?
C4 C5 C1 N1 2.4(5) . . . . ?
C8 C10 C9 C4 179.6(3) 2_566 . . . ?
C8 C10 C9 C8 -0.6(5) 2_566 . . . ?
C8 C10 C11 C12 -179.8(3) 2_566 . . . ?
C5 C4 C9 C8 -0.1(5) . . . . ?
C5 C4 C9 C10 179.7(2) . . . . ?
C5 C6 C7 C8 -0.9(5) . . . . ?
C10 C8 C9 C4 -179.6(2) 2_566 . . . ?
C10 C8 C9 C10 0.6(5) 2_566 . . . ?
C10 C8 C7 C6 -179.9(3) 2_566 . . . ?
C13 N1 C1 O1 3.0(5) . . . . ?
C13 N1 C1 C5 -176.6(3) . . . . ?
C13 N1 C2 O2 -4.5(5) . . . . ?
C13 N1 C2 C3 175.4(3) . . . . ?
C13 C14 C15 C16 175.6(3) . . . . ?
C9 C4 C5 C6 -1.2(5) . . . . ?
C9 C4 C5 C1 178.0(3) . . . . ?
C9 C8 C7 C6 -0.4(5) . . . . ?
C9 C10 C11 C12 1.3(5) . . . . ?
C14 C15 C16 C17 -176.9(4) . . . . ?
C6 C5 C1 O1 2.0(5) . . . . ?
C6 C5 C1 N1 -178.4(3) . . . . ?
C12 C3 C4 C5 -178.7(3) . . . . ?
C12 C3 C4 C9 0.4(5) . . . . ?
C12 C3 C2 O2 0.3(6) . . . . ?
C12 C3 C2 N1 -179.6(3) . . . . ?
C7 C8 C9 C4 0.9(4) . . . . ?
C7 C8 C9 C10 -178.9(3) . . . . ?
C1 N1 C13 C14 87.3(4) . . . . ?
C1 N1 C2 O2 179.5(3) . . . . ?
C1 N1 C2 C3 -0.6(5) . . . . ?
C1 C5 C6 C7 -177.5(3) . . . . ?
C11 C10 C9 C4 -1.5(4) . . . . ?
C11 C10 C9 C8 178.4(3) . . . . ?
C15 C16 C17 C18 -179.8(5) . . . . ?
C2 N1 C13 C14 -88.9(4) . . . . ?
C2 N1 C1 O1 179.1(3) . . . . ?
C2 N1 C1 C5 -0.6(5) . . . . ?
C2 C3 C4 C5 1.7(5) . . . . ?
C2 C3 C4 C9 -179.2(3) . . . . ?
C2 C3 C12 C11 179.0(3) . . . . ?
C16 C17 C18 C19A -83.4(10) . . . . ?
C16 C17 C18 C20B -161.9(14) . . . . ?

_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_PDI_C7_240K
_database_code_depnum_ccdc_archive 'CCDC 2493912'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
_audit_creation_date             2025-03-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        'N,N Diheptyl 3,4,9,10 perylenedicarboximide'
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8161(3)
_cell_length_b                   8.3243(6)
_cell_length_c                   19.1367(13)
_cell_angle_alpha                79.565(4)
_cell_angle_beta                 89.387(4)
_cell_angle_gamma                81.920(4)
_cell_volume                     746.94(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3650
_cell_measurement_temperature    240.00
_cell_measurement_theta_max      79.186
_cell_measurement_theta_min      2.348
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.802
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.5745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1219 before and 0.0604 after correction.
The Ratio of minimum to maximum transmission is 0.7616.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.034
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18928
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.805
_diffrn_reflns_theta_min         4.700
_diffrn_ambient_temperature      240.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 Data were collected at low temperature of 240 K.
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2193
_reflns_number_total             3095
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.360
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.031
_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)+(0.0972P)²+0.2245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1667
_refine_ls_wR_factor_ref         0.1848
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C19A-C18 \\sim C18-C19B
 with sigma of 0.02
2. Rigid body (RIGU) restrains
 C19A, C18, C19B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(H15B)=Sof(H16B)=Sof(C19B)=Sof(H18B)=Sof(H19B)=Sof(H17B)=1-FVAR(1)
 Sof(H16A)=Sof(H15A)=Sof(C19A)=Sof(H17A)=Sof(H18A)=Sof(H19A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C13(H5,H6), C15(H10,H9), C14(H8,H7), C16(H12,H11), C17(H14,H13), C18(H16A,
 H15A), C18(H15B,H16B)
4.b Me refined with riding coordinates:
 C19A(H17A,H18A,H19A), C19B(H18B,H19B,H17B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H1), C7(H2), C11(H3), C12(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0049(3) 0.59048(18) 0.38790(8) 0.0472(4) Uani 1 1 d . . . . .
O2 O 0.6635(3) 1.0396(2) 0.22501(8) 0.0581(5) Uani 1 1 d . . . . .
N1 N 0.8364(3) 0.8151(2) 0.30657(8) 0.0380(4) Uani 1 1 d . . . . .
C10 C 0.0118(3) 1.0980(2) 0.42973(9) 0.0302(4) Uani 1 1 d . . . . .
C5 C 0.6220(3) 0.7668(2) 0.42381(9) 0.0317(4) Uani 1 1 d . . . . .
C9 C 0.2098(3) 0.9542(2) 0.45148(9) 0.0290(4) Uani 1 1 d . . . . .
C8 C 0.2072(3) 0.8550(2) 0.52051(9) 0.0292(4) Uani 1 1 d . . . . .
C4 C 0.4222(3) 0.9087(2) 0.40305(9) 0.0302(4) Uani 1 1 d . . . . .
C6 C 0.6179(3) 0.6756(2) 0.49084(10) 0.0332(4) Uani 1 1 d . . . . .
H1 H 0.754851 0.583404 0.504913 0.040 Uiso 1 1 calc R U . . .
C7 C 0.4105(3) 0.7192(2) 0.53861(10) 0.0325(4) Uani 1 1 d . . . . .
H2 H 0.409559 0.654289 0.584214 0.039 Uiso 1 1 calc R U . . .
C3 C 0.4317(4) 1.0062(2) 0.33511(9) 0.0343(4) Uani 1 1 d . . . . .
C1 C 0.8363(4) 0.7157(2) 0.37305(10) 0.0357(4) Uani 1 1 d . . . . .
C2 C 0.6488(4) 0.9595(3) 0.28403(10) 0.0388(5) Uani 1 1 d . . . . .
C11 C 0.0319(4) 1.1911(2) 0.36252(10) 0.0373(5) Uani 1 1 d . . . . .
H3 H -0.096994 1.287103 0.348230 0.045 Uiso 1 1 calc R U . . .
C12 C 0.2400(4) 1.1451(2) 0.31551(10) 0.0385(5) Uani 1 1 d . . . . .
H4 H 0.248493 1.210002 0.270108 0.046 Uiso 1 1 calc R U . . .
C13 C 1.0392(4) 0.7594(3) 0.25438(10) 0.0417(5) Uani 1 1 d . . . . .
H5 H 1.211956 0.702317 0.279284 0.050 Uiso 1 1 calc R U . . .
H6 H 1.086376 0.855575 0.221180 0.050 Uiso 1 1 calc R U . . .
C15 C 1.1370(4) 0.5663(3) 0.16597(11) 0.0489(5) Uani 1 1 d . . . . .
H10 H 1.198657 0.653672 0.130267 0.059 Uiso 1 1 calc R U . . .
H9 H 1.300926 0.511118 0.195125 0.059 Uiso 1 1 calc R U . . .
C14 C 0.9213(4) 0.6441(3) 0.21308(11) 0.0472(5) Uani 1 1 d . . . . .
H8 H 0.763075 0.705848 0.183440 0.057 Uiso 1 1 calc R U . . .
H7 H 0.849959 0.556358 0.246684 0.057 Uiso 1 1 calc R U . . .
C16 C 1.0258(4) 0.4422(3) 0.12845(12) 0.0519(6) Uani 1 1 d . . . . .
H12 H 0.867846 0.498645 0.097399 0.062 Uiso 1 1 calc R U . . .
H11 H 0.955127 0.357924 0.164024 0.062 Uiso 1 1 calc R U . . .
C17 C 1.2460(6) 0.3579(4) 0.08419(15) 0.0699(8) Uani 1 1 d . . . . .
H14 H 1.314218 0.442542 0.048311 0.084 Uiso 1 1 calc R U . . .
H13 H 1.405327 0.303819 0.115252 0.084 Uiso 1 1 calc R U . . .
C18 C 1.1433(8) 0.2308(5) 0.0469(2) 0.0943(11) Uani 1 1 d D . . . .
H16A H 0.953010 0.273139 0.028431 0.113 Uiso 0.556(6) 1 calc R U P A 1
H15A H 1.263871 0.216815 0.006278 0.113 Uiso 0.556(6) 1 calc R U P A 1
H15B H 1.018563 0.171420 0.079638 0.113 Uiso 0.444(6) 1 calc R U P A 2
H16B H 1.028041 0.291037 0.006058 0.113 Uiso 0.444(6) 1 calc R U P A 2
C19A C 1.1402(11) 0.0851(7) 0.0878(3) 0.0749(17) Uani 0.556(6) 1 d D . P A 1
H17A H 1.072442 0.010814 0.060408 0.112 Uiso 0.556(6) 1 calc R U P A 1
H18A H 1.328565 0.040484 0.105394 0.112 Uiso 0.556(6) 1 calc R U P A 1
H19A H 1.017271 0.096887 0.127578 0.112 Uiso 0.556(6) 1 calc R U P A 1
C19B C 1.3371(16) 0.1124(12) 0.0224(6) 0.125(4) Uani 0.444(6) 1 d D . P A 2
H18B H 1.237749 0.041094 -0.000002 0.187 Uiso 0.444(6) 1 calc R U P A 2
H19B H 1.458669 0.167249 -0.011974 0.187 Uiso 0.444(6) 1 calc R U P A 2
H17B H 1.449136 0.046927 0.062040 0.187 Uiso 0.444(6) 1 calc R U P A 2


_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 1.219(2) . ?
O2 C2 1.210(2) . ?
N1 C1 1.386(2) . ?
N1 C2 1.401(3) . ?
N1 C13 1.479(2) . ?
C10 C9 1.422(3) . ?
C10 C8 1.473(2) 2_576 ?
C10 C11 1.386(2) . ?
C5 C4 1.414(3) . ?
C5 C6 1.368(3) . ?
C5 C1 1.481(2) . ?
C9 C8 1.426(2) . ?
C9 C4 1.431(2) . ?
C8 C7 1.382(2) . ?
C4 C3 1.407(2) . ?
C6 H1 0.9400 . ?
C6 C7 1.401(2) . ?
C7 H2 0.9400 . ?
C3 C2 1.484(2) . ?
C3 C12 1.371(3) . ?
C11 H3 0.9400 . ?
C11 C12 1.400(3) . ?
C12 H4 0.9400 . ?
C13 H5 0.9800 . ?
C13 H6 0.9800 . ?
C13 C14 1.518(3) . ?
C15 H10 0.9800 . ?
C15 H9 0.9800 . ?
C15 C14 1.521(3) . ?
C15 C16 1.517(3) . ?
C14 H8 0.9800 . ?
C14 H7 0.9800 . ?
C16 H12 0.9800 . ?
C16 H11 0.9800 . ?
C16 C17 1.524(3) . ?
C17 H14 0.9800 . ?
C17 H13 0.9800 . ?
C17 C18 1.517(4) . ?
C18 H16A 0.9800 . ?
C18 H15A 0.9800 . ?
C18 H15B 0.9800 . ?
C18 H16B 0.9800 . ?
C18 C19A 1.321(6) . ?
C18 C19B 1.402(7) . ?
C19A H17A 0.9700 . ?
C19A H18A 0.9700 . ?
C19A H19A 0.9700 . ?
C19B H18B 0.9700 . ?
C19B H19B 0.9700 . ?
C19B H17B 0.9700 . ?

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 C2 124.80(15) . . ?
C1 N1 C13 117.45(16) . . ?
C2 N1 C13 117.66(16) . . ?
C9 C10 C8 119.12(16) . 2_576 ?
C11 C10 C9 119.09(16) . . ?
C11 C10 C8 121.78(16) . 2_576 ?
C4 C5 C1 120.17(16) . . ?
C6 C5 C4 120.14(16) . . ?
C6 C5 C1 119.69(16) . . ?
C10 C9 C8 122.26(16) . . ?
C10 C9 C4 119.04(16) . . ?
C8 C9 C4 118.69(16) . . ?
C9 C8 C10 118.60(16) . 2_576 ?
C7 C8 C10 122.30(16) . 2_576 ?
C7 C8 C9 119.09(16) . . ?
C5 C4 C9 119.92(16) . . ?
C3 C4 C5 120.39(16) . . ?
C3 C4 C9 119.70(17) . . ?
C5 C6 H1 119.8 . . ?
C5 C6 C7 120.30(16) . . ?
C7 C6 H1 119.8 . . ?
C8 C7 C6 121.83(17) . . ?
C8 C7 H2 119.1 . . ?
C6 C7 H2 119.1 . . ?
C4 C3 C2 120.29(17) . . ?
C12 C3 C4 120.24(17) . . ?
C12 C3 C2 119.46(17) . . ?
O1 C1 N1 120.47(17) . . ?
O1 C1 C5 122.18(18) . . ?
N1 C1 C5 117.34(16) . . ?
O2 C2 N1 120.67(17) . . ?
O2 C2 C3 122.36(18) . . ?
N1 C2 C3 116.97(16) . . ?
C10 C11 H3 119.3 . . ?
C10 C11 C12 121.37(17) . . ?
C12 C11 H3 119.3 . . ?
C3 C12 C11 120.55(17) . . ?
C3 C12 H4 119.7 . . ?
C11 C12 H4 119.7 . . ?
N1 C13 H5 109.3 . . ?
N1 C13 H6 109.3 . . ?
N1 C13 C14 111.52(15) . . ?
H5 C13 H6 108.0 . . ?
C14 C13 H5 109.3 . . ?
C14 C13 H6 109.3 . . ?
H10 C15 H9 107.8 . . ?
C14 C15 H10 108.9 . . ?
C14 C15 H9 108.9 . . ?
C16 C15 H10 108.9 . . ?
C16 C15 H9 108.9 . . ?
C16 C15 C14 113.17(17) . . ?
C13 C14 C15 112.98(16) . . ?
C13 C14 H8 109.0 . . ?
C13 C14 H7 109.0 . . ?
C15 C14 H8 109.0 . . ?
C15 C14 H7 109.0 . . ?
H8 C14 H7 107.8 . . ?
C15 C16 H12 108.9 . . ?
C15 C16 H11 108.9 . . ?
C15 C16 C17 113.18(18) . . ?
H12 C16 H11 107.8 . . ?
C17 C16 H12 108.9 . . ?
C17 C16 H11 108.9 . . ?
C16 C17 H14 108.6 . . ?
C16 C17 H13 108.6 . . ?
H14 C17 H13 107.6 . . ?
C18 C17 C16 114.6(2) . . ?
C18 C17 H14 108.6 . . ?
C18 C17 H13 108.6 . . ?
C17 C18 H16A 108.7 . . ?
C17 C18 H15A 108.7 . . ?
C17 C18 H15B 107.4 . . ?
C17 C18 H16B 107.4 . . ?
H16A C18 H15A 107.6 . . ?
H15B C18 H16B 106.9 . . ?
C19A C18 C17 114.3(4) . . ?
C19A C18 H16A 108.7 . . ?
C19A C18 H15A 108.7 . . ?
C19B C18 C17 119.9(4) . . ?
C19B C18 H15B 107.4 . . ?
C19B C18 H16B 107.4 . . ?
C18 C19A H17A 109.5 . . ?
C18 C19A H18A 109.5 . . ?
C18 C19A H19A 109.5 . . ?
H17A C19A H18A 109.5 . . ?
H17A C19A H19A 109.5 . . ?
H18A C19A H19A 109.5 . . ?
C18 C19B H18B 109.5 . . ?
C18 C19B H19B 109.5 . . ?
C18 C19B H17B 109.5 . . ?
H18B C19B H19B 109.5 . . ?
H18B C19B H17B 109.5 . . ?
H19B C19B H17B 109.5 . . ?

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
N1 C13 C14 C15 -172.37(17) . . . . ?
C10 C9 C8 C10 1.2(3) . . . 2_576 ?
C10 C9 C8 C7 -178.39(15) . . . . ?
C10 C9 C4 C5 179.60(15) . . . . ?
C10 C9 C4 C3 0.0(3) . . . . ?
C10 C8 C7 C6 -179.99(16) 2_576 . . . ?
C10 C11 C12 C3 -0.4(3) . . . . ?
C5 C4 C3 C2 1.1(3) . . . . ?
C5 C4 C3 C12 -179.06(16) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C9 C8 C7 C6 -0.4(3) . . . . ?
C9 C4 C3 C2 -179.29(15) . . . . ?
C9 C4 C3 C12 0.6(3) . . . . ?
C8 C10 C9 C8 -1.2(3) 2_576 . . . ?
C8 C10 C9 C4 179.95(14) 2_576 . . . ?
C8 C10 C11 C12 -179.75(16) 2_576 . . . ?
C8 C9 C4 C5 0.7(2) . . . . ?
C8 C9 C4 C3 -178.95(15) . . . . ?
C4 C5 C6 C7 2.0(3) . . . . ?
C4 C5 C1 O1 -176.94(16) . . . . ?
C4 C5 C1 N1 2.1(2) . . . . ?
C4 C9 C8 C10 -179.95(14) . . . 2_576 ?
C4 C9 C8 C7 0.5(2) . . . . ?
C4 C3 C2 O2 179.72(18) . . . . ?
C4 C3 C2 N1 0.8(3) . . . . ?
C4 C3 C12 C11 -0.4(3) . . . . ?
C6 C5 C4 C9 -2.0(3) . . . . ?
C6 C5 C4 C3 177.68(16) . . . . ?
C6 C5 C1 O1 2.9(3) . . . . ?
C6 C5 C1 N1 -178.11(15) . . . . ?
C1 N1 C2 O2 179.83(18) . . . . ?
C1 N1 C2 C3 -1.2(3) . . . . ?
C1 N1 C13 C14 86.7(2) . . . . ?
C1 C5 C4 C9 177.84(15) . . . . ?
C1 C5 C4 C3 -2.5(3) . . . . ?
C1 C5 C6 C7 -177.78(15) . . . . ?
C2 N1 C1 O1 178.85(17) . . . . ?
C2 N1 C1 C5 -0.2(3) . . . . ?
C2 N1 C13 C14 -89.9(2) . . . . ?
C2 C3 C12 C11 179.49(17) . . . . ?
C11 C10 C9 C8 178.18(15) . . . . ?
C11 C10 C9 C4 -0.7(3) . . . . ?
C12 C3 C2 O2 -0.2(3) . . . . ?
C12 C3 C2 N1 -179.10(16) . . . . ?
C13 N1 C1 O1 2.5(3) . . . . ?
C13 N1 C1 C5 -176.53(15) . . . . ?
C13 N1 C2 O2 -3.8(3) . . . . ?
C13 N1 C2 C3 175.13(15) . . . . ?
C15 C16 C17 C18 179.0(3) . . . . ?
C14 C15 C16 C17 -177.1(2) . . . . ?
C16 C15 C14 C13 176.09(18) . . . . ?
C16 C17 C18 C19A -81.2(4) . . . . ?
C16 C17 C18 C19B -161.4(6) . . . . ?

_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_PDI_C8_0_61GPa
_database_code_depnum_ccdc_archive 'CCDC 2493919'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
_audit_creation_date             2025-07-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C8
_chemical_name_systematic        'N,N Dioctyl 3,4,9,10 perylenedicarboximide'
_chemical_formula_moiety         'C40 H42 N2 O4'
_chemical_formula_sum            'C40 H42 N2 O4'
_chemical_formula_weight         614.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C40 H42 N2 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.5642(19)
_cell_length_b                   8.442(4)
_cell_length_c                   19.398(12)
_cell_angle_alpha                83.02(8)
_cell_angle_beta                 88.30(9)
_cell_angle_gamma                82.94(3)
_cell_volume                     736.2(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    733
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2100
_cell_measurement_theta_min      4.4620
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.980
_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
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 0 0 0.0822
0 -12 -2 0.0577
-6 3 0 0.0782
0 -1 -27 0.0170
0 0 27 0.0170
1 12 4 0.0600

_exptl_crystal_preparation       'mounted in a diamond-anvil cell'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.3996 0.2253 0.2296 -0.0642 0.8496 0.5234
0.3959 -11.6928 -2.2475 -0.0536 0.6544 -0.7542
-6.0619 2.5853 0.3233 0.0727 -0.9487 -0.3078
-0.1298 -0.5667 -27.2726 -0.9969 -0.0776 -0.0089
-0.1015 -0.0345 27.1228 0.9958 0.0773 -0.0498
0.7500 11.9016 3.6131 0.0902 -0.5067 0.8574

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2214
_diffrn_reflns_av_unetI/netI     0.4715
_diffrn_reflns_Laue_measured_fraction_full 0.323
_diffrn_reflns_Laue_measured_fraction_max 0.203
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2951
_diffrn_reflns_point_group_measured_fraction_full 0.323
_diffrn_reflns_point_group_measured_fraction_max 0.203
_diffrn_reflns_theta_full        12.500
_diffrn_reflns_theta_max         25.660
_diffrn_reflns_theta_min         4.500
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1544
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.323
_diffrn_measured_fraction_theta_max 0.203
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  18.20   0.85   15.00    --   15.70  39.00 -12.00   32
  2  ω    -30.00   0.60   0.85   15.00    --   15.70   0.00-150.00   36
  3  ω    -47.00 -25.75   0.85   15.00    --   15.70 134.00 123.00   25
  4  ω    -16.00  40.10   0.85   15.00    --   15.70 -39.00  12.00   66
  5  ω    -35.00 -13.75   0.85   15.00    --   15.70 114.00 -44.00   25
  6  ω    -18.00  13.45   0.85   15.00    --   15.70 -19.00  30.00   37
  7  ω    -17.00  40.80   0.85   15.00    --   15.70 -39.00-167.00   68
  8  ω    -17.00  42.50   0.85   15.00    --   15.70 -19.00-180.00   70
  9  ω    -29.00  26.25   0.85   15.00    --   15.70  13.00  -3.00   65
 10  ω     -8.00  18.35   0.85   15.00    --   15.70  39.00 167.00   31
 11  ω     13.00  33.40   0.85   15.00    --  -16.49-114.00  44.00   24
 12  ω    -40.00  22.05   0.85   15.00    --  -16.49  26.00  -7.00   73
 13  ω    -79.00 -25.45   0.85   15.00    --  -16.49 134.00 -56.00   63
 14  ω     25.00  46.25   0.85   15.00    --  -16.49-134.00  56.00   25
 15  ω    -35.00  26.20   0.85   15.00    --  -16.49  13.00  -3.00   72
 16  ω    -42.00  18.35   0.85   15.00    --  -16.49  39.00 167.00   71
 17  ω    -19.00  27.75   0.85   15.00    --  -16.49 -19.00-180.00   55
 18  ω    -36.00  -4.55   0.85   15.00    --  -16.49  57.00 150.00   37
 19  ω    -27.00  35.05   0.85   15.00    --  -16.49 -13.00   3.00   73
 20  ω    -23.00  15.25   0.85   15.00    --  -16.49 -26.00-172.00   45
 21  ω    -66.00 -13.30   0.85   15.00    --  -16.49 114.00 -44.00   62
 22  ω     13.00  33.40   0.85   15.00    --  -16.49-114.00-136.00   24
 23  ω    -80.00 -25.60   0.85   15.00    --  -16.49 134.00 123.00   64
 24  ω      4.00  23.55   0.85   15.00    --  -16.49 -97.00  35.00   23
 25  ω      5.00  36.45   0.85   15.00    --   15.70 -57.00-150.00   37
 26  ω    -30.00   0.60   0.85   15.00    --   15.70   0.00  30.00   36
 27  ω    -35.00 -13.75   0.85   15.00    --   15.70 114.00 136.00   25
 28  ω     -5.00  19.65   0.85   15.00    --   15.70  57.00 150.00   29
 29  ω     20.00  45.50   0.85   15.00    --   15.70 -77.00  30.00   30
 30  ω    -14.00   5.55   0.85   15.00    --   15.70  77.00 -30.00   23
 31  ω    -27.00  18.05   0.85   15.00    --   15.70  19.00-180.00   53
 32  ω     -6.00  41.60   0.85   15.00    --   15.70 -37.00-180.00   56
 33  ω    -18.00  13.45   0.85   15.00    --   15.70 -19.00-150.00   37
 34  ω    -47.00 -25.75   0.85   15.00    --   15.70 134.00 -56.00   25
 35  ω    -37.00  -7.25   0.85   15.00    --  -16.49  57.00 -30.00   35
 36  ω    -35.00  26.20   0.85   15.00    --  -16.49  13.00 176.00   72
 37  ω    -46.00 -19.65   0.85   15.00    --  -16.49  77.00 150.00   31
 38  ω    -46.00 -19.65   0.85   15.00    --  -16.49  77.00 -30.00   31
 39  ω    -20.00   4.65   0.85   15.00    --  -16.49 -57.00-150.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_axis[1]    matrixX
_diffrn_orient_matrix_axis[2]    matrixY
_diffrn_orient_matrix_axis[3]    matrixZ
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0112453000
_diffrn_orient_matrix_UB_12      -0.0028425000
_diffrn_orient_matrix_UB_13      0.0366675000
_diffrn_orient_matrix_UB_21      0.1344786000
_diffrn_orient_matrix_UB_22      -0.0520469000
_diffrn_orient_matrix_UB_23      0.0032859000
_diffrn_orient_matrix_UB_31      0.0794694000
_diffrn_orient_matrix_UB_32      0.0674724000
_diffrn_orient_matrix_UB_33      -0.0014525000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 0.61(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                144
_reflns_number_total             569
_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    ?
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         569
_refine_ls_number_restraints     418
_refine_ls_R_factor_all          0.4366
_refine_ls_R_factor_gt           0.1632
_refine_ls_restrained_S_all      0.728
_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)+(0.1708P)²+22.1187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3449
_refine_ls_wR_factor_ref         0.5347
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C14-C13 \\sim C15-C14 \\sim C16-C15 \\sim C17-C16 \\sim C18-C17 \\sim C19-C18
 with sigma of 0.02
 N1-C13 \\sim N1-C1 \\sim N1-C2
 with sigma of 0.02
 C2-C3 \\sim C3-C12 \\sim C12-C11 \\sim C11-C10 \\sim C10-C9 \\sim C9-C4 \\sim
C4-C3 \\sim C9-C8 \\sim C8-C7 ~
 C7-C6 \\sim C6-C5 \\sim C5-C4 \\sim C5-C1
 with sigma of 0.02
 C1-O1 \\sim C2-O2
 with sigma of 0.02
 C19-C20 \\sim C19-C18 \\sim C18-C17 \\sim C17-C16 \\sim C16-C15 \\sim C15-C14
\\sim C14-C13
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(O2) \\sim
Ueq, Uanis(C9) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C4)
\\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq,
Uanis(C3) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C14) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C17)
\\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C20) \\sim Ueq,
Uanis(C13) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 N1, O1, C1, C5, C2, C13, C4, C6, C7, O2, C3, C14, C9, C8, C12, C15, C10, C11,
 C16, C17, C18, C19, C20
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C14, C13, C16, C15, C17, C19, C18, C20
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C14(H8,H7), C13(H5,H6), C16(H12,H11), C15(H10,H9), C17(H14,H13), C19(H18,H17),
  C18(H16,H15)
4.b Aromatic/amide H refined with riding coordinates:
 C6(H1), C7(H2), C12(H4), C11(H3)
4.c Idealised Me refined as rotating group:
 C20(H21,H19,H20)
;
_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 -0.013(6) 0.503(3) 0.398(4) 0.052(11) Uani 1 1 d D U . . .
N1 N 0.133(6) 0.328(4) 0.311(3) 0.042(7) Uani 1 1 d D U . . .
C10 C 0.980(9) -0.040(5) 0.430(4) 0.038(9) Uani 1 1 d D U . . .
C8 C 0.814(8) 0.134(4) 0.519(4) 0.034(9) Uani 1 1 d D U . . .
O2 O 0.299(7) 0.167(4) 0.227(4) 0.056(10) Uani 1 1 d D U . . .
C9 C 0.785(7) 0.084(4) 0.453(3) 0.024(8) Uani 1 1 d D U . . .
C5 C 0.363(8) 0.285(4) 0.424(3) 0.035(8) Uani 1 1 d D U . . .
C2 C 0.359(10) 0.204(5) 0.286(4) 0.035(9) Uani 1 1 d D U . . .
C4 C 0.581(7) 0.166(4) 0.404(2) 0.028(8) Uani 1 1 d D U . . .
C1 C 0.157(9) 0.383(4) 0.380(4) 0.037(8) Uani 1 1 d D U . . .
C6 C 0.392(8) 0.330(4) 0.491(4) 0.031(8) Uani 1 1 d D U . . .
H1 H 0.259181 0.414256 0.503921 0.037 Uiso 1 1 calc R U . . .
C7 C 0.605(6) 0.257(4) 0.540(5) 0.032(8) Uani 1 1 d D U . . .
H2 H 0.607296 0.289369 0.584127 0.039 Uiso 1 1 calc R U . . .
C14 C 0.085(8) 0.560(4) 0.225(5) 0.057(11) Uani 1 1 d D U . . .
H8 H 0.235284 0.516747 0.194305 0.068 Uiso 1 1 calc R U . . .
H7 H 0.181623 0.608205 0.260182 0.068 Uiso 1 1 calc R U . . .
C3 C 0.551(7) 0.118(4) 0.337(3) 0.026(8) Uani 1 1 d D U . . .
C12 C 0.745(7) -0.006(4) 0.312(4) 0.039(9) Uani 1 1 d D U . . .
H4 H 0.743814 -0.031959 0.267183 0.047 Uiso 1 1 calc R U . . .
C11 C 0.941(9) -0.086(5) 0.363(4) 0.035(9) Uani 1 1 d D U . . .
H3 H 1.055423 -0.178621 0.352471 0.042 Uiso 1 1 calc R U . . .
C13 C -0.079(8) 0.426(4) 0.261(5) 0.043(9) Uani 1 1 d D U . . .
H5 H -0.253862 0.469019 0.285004 0.052 Uiso 1 1 calc R U . . .
H6 H -0.137278 0.360271 0.227043 0.052 Uiso 1 1 calc R U . . .
C16 C 0.012(9) 0.834(4) 0.150(6) 0.062(11) Uani 1 1 d D U . . .
H12 H 0.166045 0.796333 0.118230 0.074 Uiso 1 1 calc R U . . .
H11 H 0.105291 0.880818 0.185429 0.074 Uiso 1 1 calc R U . . .
C15 C -0.126(9) 0.689(5) 0.185(5) 0.063(11) Uani 1 1 d D U . . .
H10 H -0.215756 0.640262 0.148988 0.075 Uiso 1 1 calc R U . . .
H9 H -0.282547 0.726313 0.215701 0.075 Uiso 1 1 calc R U . . .
C17 C -0.194(9) 0.966(4) 0.110(5) 0.059(11) Uani 1 1 d D U . . .
H14 H -0.298874 0.918585 0.076287 0.070 Uiso 1 1 calc R U . . .
H13 H -0.339082 1.010436 0.141891 0.070 Uiso 1 1 calc R U . . .
C19 C -0.257(10) 1.239(5) 0.034(6) 0.064(13) Uani 1 1 d D U . . .
H18 H -0.160299 1.292678 -0.005550 0.077 Uiso 1 1 calc R U . . .
H17 H -0.429900 1.197931 0.018627 0.077 Uiso 1 1 calc R U . . .
C18 C -0.047(9) 1.104(4) 0.071(5) 0.066(12) Uani 1 1 d D U . . .
H16 H 0.090934 1.060533 0.037075 0.079 Uiso 1 1 calc R U . . .
H15 H 0.066544 1.148056 0.104005 0.079 Uiso 1 1 calc R U . . .
C20 C -0.341(13) 1.352(7) 0.088(6) 0.12(2) Uani 1 1 d D U . . .
H21 H -0.325736 1.460729 0.068342 0.174 Uiso 1 1 calc R U . . .
H19 H -0.210099 1.324944 0.127009 0.174 Uiso 1 1 calc R U . . .
H20 H -0.540238 1.343090 0.104112 0.174 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 1.27(6) . ?
N1 C2 1.49(4) . ?
N1 C1 1.49(4) . ?
N1 C13 1.49(4) . ?
C10 C8 1.47(8) 2_756 ?
C10 C9 1.40(2) . ?
C10 C11 1.41(3) . ?
C8 C9 1.41(2) . ?
C8 C7 1.41(2) . ?
O2 C2 1.27(6) . ?
C9 C4 1.41(2) . ?
C5 C4 1.41(2) . ?
C5 C1 1.41(3) . ?
C5 C6 1.41(2) . ?
C2 C3 1.41(2) . ?
C4 C3 1.41(2) . ?
C6 H1 0.9300 . ?
C6 C7 1.41(2) . ?
C7 H2 0.9300 . ?
C14 H8 0.9700 . ?
C14 H7 0.9700 . ?
C14 C13 1.52(2) . ?
C14 C15 1.52(2) . ?
C3 C12 1.41(2) . ?
C12 H4 0.9300 . ?
C12 C11 1.41(2) . ?
C11 H3 0.9300 . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C16 H12 0.9700 . ?
C16 H11 0.9700 . ?
C16 C15 1.52(2) . ?
C16 C17 1.52(2) . ?
C15 H10 0.9700 . ?
C15 H9 0.9700 . ?
C17 H14 0.9700 . ?
C17 H13 0.9700 . ?
C17 C18 1.52(2) . ?
C19 H18 0.9700 . ?
C19 H17 0.9700 . ?
C19 C18 1.52(2) . ?
C19 C20 1.52(3) . ?
C18 H16 0.9700 . ?
C18 H15 0.9700 . ?
C20 H21 0.9600 . ?
C20 H19 0.9600 . ?
C20 H20 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 121(4) . . ?
C2 N1 C13 120(5) . . ?
C1 N1 C13 118(4) . . ?
C9 C10 C8 117(5) . 2_756 ?
C9 C10 C11 120(5) . . ?
C11 C10 C8 123(4) . 2_756 ?
C9 C8 C10 121(3) . 2_756 ?
C9 C8 C7 118(4) . . ?
C7 C8 C10 120(5) . 2_756 ?
C10 C9 C8 122(4) . . ?
C10 C9 C4 115(4) . . ?
C8 C9 C4 123(4) . . ?
C1 C5 C4 126(4) . . ?
C6 C5 C4 116(4) . . ?
C6 C5 C1 117(4) . . ?
O2 C2 N1 113(4) . . ?
O2 C2 C3 129(4) . . ?
C3 C2 N1 116(5) . . ?
C5 C4 C9 119(4) . . ?
C5 C4 C3 116(4) . . ?
C3 C4 C9 124(3) . . ?
O1 C1 N1 121(4) . . ?
O1 C1 C5 125(6) . . ?
C5 C1 N1 114(4) . . ?
C5 C6 H1 117.4 . . ?
C5 C6 C7 125(4) . . ?
C7 C6 H1 117.4 . . ?
C8 C7 H2 121.3 . . ?
C6 C7 C8 117(4) . . ?
C6 C7 H2 121.3 . . ?
H8 C14 H7 108.0 . . ?
C13 C14 H8 109.4 . . ?
C13 C14 H7 109.4 . . ?
C13 C14 C15 111(3) . . ?
C15 C14 H8 109.4 . . ?
C15 C14 H7 109.4 . . ?
C2 C3 C4 124(4) . . ?
C12 C3 C2 114(4) . . ?
C12 C3 C4 122(4) . . ?
C3 C12 H4 123.7 . . ?
C11 C12 C3 113(4) . . ?
C11 C12 H4 123.7 . . ?
C10 C11 H3 116.8 . . ?
C12 C11 C10 126(5) . . ?
C12 C11 H3 116.8 . . ?
N1 C13 C14 106(4) . . ?
N1 C13 H5 110.6 . . ?
N1 C13 H6 110.6 . . ?
C14 C13 H5 110.6 . . ?
C14 C13 H6 110.6 . . ?
H5 C13 H6 108.7 . . ?
H12 C16 H11 107.3 . . ?
C15 C16 H12 108.1 . . ?
C15 C16 H11 108.1 . . ?
C15 C16 C17 117(3) . . ?
C17 C16 H12 108.1 . . ?
C17 C16 H11 108.1 . . ?
C14 C15 H10 108.4 . . ?
C14 C15 H9 108.4 . . ?
C16 C15 C14 116(3) . . ?
C16 C15 H10 108.4 . . ?
C16 C15 H9 108.4 . . ?
H10 C15 H9 107.4 . . ?
C16 C17 H14 108.3 . . ?
C16 C17 H13 108.3 . . ?
H14 C17 H13 107.4 . . ?
C18 C17 C16 116(4) . . ?
C18 C17 H14 108.3 . . ?
C18 C17 H13 108.3 . . ?
H18 C19 H17 108.9 . . ?
C18 C19 H18 110.8 . . ?
C18 C19 H17 110.8 . . ?
C20 C19 H18 110.8 . . ?
C20 C19 H17 110.8 . . ?
C20 C19 C18 105(4) . . ?
C17 C18 C19 115(4) . . ?
C17 C18 H16 108.5 . . ?
C17 C18 H15 108.5 . . ?
C19 C18 H16 108.5 . . ?
C19 C18 H15 108.5 . . ?
H16 C18 H15 107.5 . . ?
C19 C20 H21 109.5 . . ?
C19 C20 H19 109.5 . . ?
C19 C20 H20 109.5 . . ?
H21 C20 H19 109.5 . . ?
H21 C20 H20 109.5 . . ?
H19 C20 H20 109.5 . . ?

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
N1 C2 C3 C4 -14(6) . . . . ?
N1 C2 C3 C12 175(3) . . . . ?
C10 C8 C9 C10 -10(7) 2_756 . . . ?
C10 C8 C9 C4 177(4) 2_756 . . . ?
C10 C8 C7 C6 -173(4) 2_756 . . . ?
C10 C9 C4 C5 176(4) . . . . ?
C10 C9 C4 C3 6(5) . . . . ?
C8 C10 C9 C8 10(6) 2_756 . . . ?
C8 C10 C9 C4 -177(4) 2_756 . . . ?
C8 C10 C11 C12 179(4) 2_756 . . . ?
C8 C9 C4 C5 -11(6) . . . . ?
C8 C9 C4 C3 179(4) . . . . ?
O2 C2 C3 C4 -174(5) . . . . ?
O2 C2 C3 C12 15(8) . . . . ?
C9 C10 C11 C12 9(7) . . . . ?
C9 C8 C7 C6 -4(5) . . . . ?
C9 C4 C3 C2 -177(4) . . . . ?
C9 C4 C3 C12 -6(6) . . . . ?
C5 C4 C3 C2 13(6) . . . . ?
C5 C4 C3 C12 -177(4) . . . . ?
C5 C6 C7 C8 3(6) . . . . ?
C2 N1 C1 O1 171(5) . . . . ?
C2 N1 C1 C5 -13(6) . . . . ?
C2 N1 C13 C14 -82(5) . . . . ?
C2 C3 C12 C11 178(4) . . . . ?
C4 C5 C1 O1 -171(4) . . . . ?
C4 C5 C1 N1 14(6) . . . . ?
C4 C5 C6 C7 -5(6) . . . . ?
C4 C3 C12 C11 7(5) . . . . ?
C1 N1 C2 O2 177(5) . . . . ?
C1 N1 C2 C3 14(5) . . . . ?
C1 N1 C13 C14 84(5) . . . . ?
C1 C5 C4 C9 176(4) . . . . ?
C1 C5 C4 C3 -13(6) . . . . ?
C1 C5 C6 C7 -174(4) . . . . ?
C6 C5 C4 C9 9(5) . . . . ?
C6 C5 C4 C3 179(4) . . . . ?
C6 C5 C1 O1 -3(7) . . . . ?
C6 C5 C1 N1 -179(4) . . . . ?
C7 C8 C9 C10 -179(4) . . . . ?
C7 C8 C9 C4 9(6) . . . . ?
C3 C12 C11 C10 -9(6) . . . . ?
C11 C10 C9 C8 180(4) . . . . ?
C11 C10 C9 C4 -7(6) . . . . ?
C13 N1 C2 O2 -17(6) . . . . ?
C13 N1 C2 C3 180(4) . . . . ?
C13 N1 C1 O1 5(6) . . . . ?
C13 N1 C1 C5 -179(4) . . . . ?
C13 C14 C15 C16 177(6) . . . . ?
C16 C17 C18 C19 -177(5) . . . . ?
C15 C14 C13 N1 -168(5) . . . . ?
C15 C16 C17 C18 -176(6) . . . . ?
C17 C16 C15 C14 -179(5) . . . . ?
C20 C19 C18 C17 88(7) . . . . ?

loop_
_axis.id
_axis.type
_axis.equipment
_axis.parity
_axis.depends_on
_axis.zero
_axis.vector[1]
_axis.vector[2]
_axis.vector[3]
source . source . . . 0.99999854 0.00000000 -0.00170745
omega rotation goniometer -1 . -0.38386000 0.00000000 0.00000000 1.00000000
kappa rotation goniometer -1 omega -0.01602000 -0.76833145 0.00000000
0.64005217
phi rotation goniometer -1 kappa . -0.00003875 0.00000000 1.00000000
theta rotation goniometer -1 . -0.36758000 0.00000000 0.00000000 1.00000000
matrixX general general . phi . 1.00000000 0.00000000 0.00000000
matrixY general general . phi . 0.00000000 1.00000000 0.00000000
matrixZ general general . phi . 0.00000000 0.00000000 1.00000000
dacX translation general . phi . 0.00000000 1.00000000 0.00000000
dacY translation general . phi . -1.00000000 0.00000000 0.00000000
dacZ translation general . phi . 0.00000000 0.00000000 1.00000000

_hp_anvil_anvil_thickness        1.95
_hp_anvil_material               diamond
_hp_cell_type                    'Diamond anvil cell'
_hp_open_angle                   40.00
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 4.963
_oxdiff_exptl_absorpt_empirical_full_min 0.461
_vrf_PLAT020_PDI_C8_0_61GPa      
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.221 Report
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle. The investigated needle-shaped single crystal was poorly 
diffractive and has low symmetry. 
;
# start Validation Reply Form
_vrf_PLAT026_PDI_C8_0_61GPa      
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        25% Check 
RESPONSE: Due to the overall poor diffraction quality
of the needle-shaped crystal and low symmetry.
;
_vrf_PLAT027_PDI_C8_0_61GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      12.50 Degree
RESPONSE: Due to the specificity of the applied measuring technique and use 
of a diamond-anvil cell limiting the access of the X-ray radiation to the 
measured sample. A full set of data was collected.
;
_vrf_PLAT029_PDI_C8_0_61GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.323 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT082_PDI_C8_0_61GPa      
;
PROBLEM: High R1 Value ..................................       0.16 Report
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle. The investigated needle-shaped single crystal was poorly 
diffractive and has low symmetry. 
;
_vrf_PLAT084_PDI_C8_0_61GPa      
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.53 Report 
RESPONSE: The high factor results from the weak diffraction. Additionally, due 
to the high-pressure DAC used in this experiment, part of diffraction data 
is omitted. 
;
_vrf_PLAT088_PDI_C8_0_61GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.72 Note  
RESPONSE:  The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C8_0_61GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.07952 Ang.  
RESPONSE:  These data come from high-pressure experiment and part of the 
reflections can not be collected, affecting bond precision. In addition, 
despite multiple attempts to grow better diffracting crystals, it was not 
successful.
;
_vrf_PLAT910_PDI_C8_0_61GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         11 Note  
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT911_PDI_C8_0_61GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        364 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
_vrf_RINTA01_PDI_C8_0_61GPa      
;
PROBLEM: The value of Rint is greater than 0.18
            Rint given   0.221 
RESPONSE: The investigated needle-shaped single crystal was poorly 
diffractive and has low symmetry. 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 high-pressure were unsuccessful.
;
####################################################################### 
# 
# 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_PDI_C7_200K
_database_code_depnum_ccdc_archive 'CCDC 2493913'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
_audit_creation_date             2025-03-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        'N,N Diheptyl 3,4,9,10 perylenedicarboximide'
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8090(3)
_cell_length_b                   8.3005(5)
_cell_length_c                   19.0649(11)
_cell_angle_alpha                79.525(3)
_cell_angle_beta                 89.687(3)
_cell_angle_gamma                82.082(3)
_cell_volume                     741.05(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4924
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      64.904
_cell_measurement_theta_min      2.357
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.800
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.7525
_exptl_absorpt_correction_T_min  0.6320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1293 before and 0.0598 after correction.
The Ratio of minimum to maximum transmission is 0.8399.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.034
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22978
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        64.994
_diffrn_reflns_theta_max         64.994
_diffrn_reflns_theta_min         4.718
_diffrn_ambient_temperature      200.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 Data were collected at low temperature of 200 K.
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1958
_reflns_number_total             2467
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.208
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2467
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.049
_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)+(0.0720P)²+0.2063P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1371
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C18-C19A \\sim C18-C19B
 with sigma of 0.02
2. Rigid body (RIGU) restrains
 C19A, C19B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(H15B)=Sof(H16B)=Sof(C19B)=Sof(H18B)=Sof(H19B)=Sof(H17B)=1-FVAR(1)
 Sof(H16A)=Sof(H15A)=Sof(C19A)=Sof(H17A)=Sof(H18A)=Sof(H19A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C15(H9,H10), C14(H7,H8), C13(H5,H6), C16(H12,H11), C17(H14,H13), C18(H16A,
 H15A), C18(H15B,H16B)
4.b Me refined with riding coordinates:
 C19A(H17A,H18A,H19A), C19B(H18B,H19B,H17B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H1), C7(H2), C11(H3), C12(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0034(2) 0.59029(14) 0.38761(6) 0.0414(3) Uani 1 1 d . . . . .
O2 O 0.6606(3) 1.04128(17) 0.22394(6) 0.0500(4) Uani 1 1 d . . . . .
N1 N 0.8346(3) 0.81635(17) 0.30599(7) 0.0330(3) Uani 1 1 d . . . . .
C8 C 0.2069(3) 0.85503(18) 0.52050(8) 0.0270(4) Uani 1 1 d . . . . .
C10 C 0.0104(3) 1.09922(19) 0.42930(8) 0.0274(4) Uani 1 1 d . . . . .
C9 C 0.2099(3) 0.95418(19) 0.45140(8) 0.0271(4) Uani 1 1 d . . . . .
C5 C 0.6213(3) 0.76694(19) 0.42363(8) 0.0288(4) Uani 1 1 d . . . . .
C6 C 0.6174(3) 0.67574(19) 0.49098(8) 0.0298(4) Uani 1 1 d . . . . .
H1 H 0.756069 0.582349 0.505279 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4204(3) 0.90940(19) 0.40269(8) 0.0271(4) Uani 1 1 d . . . . .
C7 C 0.4114(3) 0.71859(19) 0.53901(8) 0.0299(4) Uani 1 1 d . . . . .
H2 H 0.411502 0.652802 0.585327 0.036 Uiso 1 1 calc R U . . .
C1 C 0.8344(3) 0.7166(2) 0.37270(9) 0.0320(4) Uani 1 1 d . . . . .
C3 C 0.4299(3) 1.0071(2) 0.33462(8) 0.0305(4) Uani 1 1 d . . . . .
C11 C 0.0305(3) 1.1919(2) 0.36201(8) 0.0327(4) Uani 1 1 d . . . . .
H3 H -0.100231 1.288889 0.347401 0.039 Uiso 1 1 calc R U . . .
C12 C 0.2376(3) 1.1469(2) 0.31484(9) 0.0341(4) Uani 1 1 d . . . . .
H4 H 0.245718 1.213198 0.268864 0.041 Uiso 1 1 calc R U . . .
C2 C 0.6459(3) 0.9611(2) 0.28314(9) 0.0343(4) Uani 1 1 d . . . . .
C15 C 1.1337(4) 0.5674(2) 0.16513(10) 0.0425(4) Uani 1 1 d . . . . .
H9 H 1.299811 0.511978 0.194864 0.051 Uiso 1 1 calc R U . . .
H10 H 1.195617 0.655926 0.128856 0.051 Uiso 1 1 calc R U . . .
C14 C 0.9182(3) 0.6452(2) 0.21212(9) 0.0404(4) Uani 1 1 d . . . . .
H7 H 0.846014 0.556359 0.246157 0.048 Uiso 1 1 calc R U . . .
H8 H 0.758214 0.707749 0.181872 0.048 Uiso 1 1 calc R U . . .
C13 C 1.0370(3) 0.7610(2) 0.25366(9) 0.0369(4) Uani 1 1 d . . . . .
H5 H 1.212054 0.703423 0.278975 0.044 Uiso 1 1 calc R U . . .
H6 H 1.084134 0.858681 0.220018 0.044 Uiso 1 1 calc R U . . .
C16 C 1.0224(4) 0.4420(2) 0.12745(10) 0.0449(5) Uani 1 1 d . . . . .
H12 H 0.862063 0.498607 0.095865 0.054 Uiso 1 1 calc R U . . .
H11 H 0.951903 0.356370 0.163569 0.054 Uiso 1 1 calc R U . . .
C17 C 1.2426(4) 0.3583(3) 0.08324(12) 0.0609(6) Uani 1 1 d . . . . .
H14 H 1.308963 0.444003 0.046390 0.073 Uiso 1 1 calc R U . . .
H13 H 1.405318 0.305061 0.114685 0.073 Uiso 1 1 calc R U . . .
C18 C 1.1394(6) 0.2286(4) 0.04668(16) 0.0827(9) Uani 1 1 d D . . . .
H16A H 0.946655 0.270853 0.027766 0.099 Uiso 0.532(5) 1 calc R U P A 1
H15A H 1.260502 0.214112 0.005498 0.099 Uiso 0.532(5) 1 calc R U P A 1
H15B H 1.021069 0.165178 0.080912 0.099 Uiso 0.468(5) 1 calc R U P A 2
H16B H 1.015438 0.287776 0.006145 0.099 Uiso 0.468(5) 1 calc R U P A 2
C19A C 1.1364(9) 0.0820(5) 0.0878(2) 0.0577(13) Uani 0.532(5) 1 d D . P A 1
H17A H 1.067373 0.006849 0.059938 0.087 Uiso 0.532(5) 1 calc R U P A 1
H18A H 1.327052 0.036946 0.105725 0.087 Uiso 0.532(5) 1 calc R U P A 1
H19A H 1.012516 0.093811 0.128042 0.087 Uiso 0.532(5) 1 calc R U P A 1
C19B C 1.3369(12) 0.1138(9) 0.0205(4) 0.101(3) Uani 0.468(5) 1 d D . P A 2
H18B H 1.238632 0.039012 -0.001408 0.152 Uiso 0.468(5) 1 calc R U P A 2
H19B H 1.452066 0.172809 -0.015248 0.152 Uiso 0.468(5) 1 calc R U P A 2
H17B H 1.457727 0.049546 0.059925 0.152 Uiso 0.468(5) 1 calc R U P A 2


_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(2) . ?
O2 C2 1.209(2) . ?
N1 C1 1.386(2) . ?
N1 C2 1.404(2) . ?
N1 C13 1.478(2) . ?
C8 C10 1.471(2) 2_576 ?
C8 C9 1.422(2) . ?
C8 C7 1.388(2) . ?
C10 C9 1.431(2) . ?
C10 C11 1.381(2) . ?
C9 C4 1.427(2) . ?
C5 C6 1.368(2) . ?
C5 C4 1.417(2) . ?
C5 C1 1.479(2) . ?
C6 H1 0.9500 . ?
C6 C7 1.399(2) . ?
C4 C3 1.404(2) . ?
C7 H2 0.9500 . ?
C3 C12 1.376(2) . ?
C3 C2 1.485(2) . ?
C11 H3 0.9500 . ?
C11 C12 1.396(2) . ?
C12 H4 0.9500 . ?
C15 H9 0.9900 . ?
C15 H10 0.9900 . ?
C15 C14 1.520(2) . ?
C15 C16 1.522(2) . ?
C14 H7 0.9900 . ?
C14 H8 0.9900 . ?
C14 C13 1.520(2) . ?
C13 H5 0.9900 . ?
C13 H6 0.9900 . ?
C16 H12 0.9900 . ?
C16 H11 0.9900 . ?
C16 C17 1.522(3) . ?
C17 H14 0.9900 . ?
C17 H13 0.9900 . ?
C17 C18 1.522(3) . ?
C18 H16A 0.9900 . ?
C18 H15A 0.9900 . ?
C18 H15B 0.9900 . ?
C18 H16B 0.9900 . ?
C18 C19A 1.323(5) . ?
C18 C19B 1.406(5) . ?
C19A H17A 0.9800 . ?
C19A H18A 0.9800 . ?
C19A H19A 0.9800 . ?
C19B H18B 0.9800 . ?
C19B H19B 0.9800 . ?
C19B H17B 0.9800 . ?

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 C2 124.71(14) . . ?
C1 N1 C13 117.60(13) . . ?
C2 N1 C13 117.58(13) . . ?
C9 C8 C10 119.22(14) . 2_576 ?
C7 C8 C10 121.77(14) . 2_576 ?
C7 C8 C9 119.01(15) . . ?
C9 C10 C8 118.68(14) . 2_576 ?
C11 C10 C8 122.43(14) . 2_576 ?
C11 C10 C9 118.88(15) . . ?
C8 C9 C10 122.09(15) . . ?
C8 C9 C4 119.16(15) . . ?
C4 C9 C10 118.75(15) . . ?
C6 C5 C4 119.94(14) . . ?
C6 C5 C1 120.00(14) . . ?
C4 C5 C1 120.06(15) . . ?
C5 C6 H1 119.7 . . ?
C5 C6 C7 120.69(14) . . ?
C7 C6 H1 119.7 . . ?
C5 C4 C9 119.71(15) . . ?
C3 C4 C9 120.07(15) . . ?
C3 C4 C5 120.22(14) . . ?
C8 C7 C6 121.47(15) . . ?
C8 C7 H2 119.3 . . ?
C6 C7 H2 119.3 . . ?
O1 C1 N1 120.33(15) . . ?
O1 C1 C5 122.05(15) . . ?
N1 C1 C5 117.60(14) . . ?
C4 C3 C2 120.66(15) . . ?
C12 C3 C4 120.12(15) . . ?
C12 C3 C2 119.22(15) . . ?
C10 C11 H3 119.1 . . ?
C10 C11 C12 121.86(15) . . ?
C12 C11 H3 119.1 . . ?
C3 C12 C11 120.31(15) . . ?
C3 C12 H4 119.8 . . ?
C11 C12 H4 119.8 . . ?
O2 C2 N1 120.52(15) . . ?
O2 C2 C3 122.78(15) . . ?
N1 C2 C3 116.70(14) . . ?
H9 C15 H10 107.7 . . ?
C14 C15 H9 108.9 . . ?
C14 C15 H10 108.9 . . ?
C14 C15 C16 113.26(14) . . ?
C16 C15 H9 108.9 . . ?
C16 C15 H10 108.9 . . ?
C15 C14 H7 109.0 . . ?
C15 C14 H8 109.0 . . ?
C15 C14 C13 112.95(13) . . ?
H7 C14 H8 107.8 . . ?
C13 C14 H7 109.0 . . ?
C13 C14 H8 109.0 . . ?
N1 C13 C14 111.48(13) . . ?
N1 C13 H5 109.3 . . ?
N1 C13 H6 109.3 . . ?
C14 C13 H5 109.3 . . ?
C14 C13 H6 109.3 . . ?
H5 C13 H6 108.0 . . ?
C15 C16 H12 109.0 . . ?
C15 C16 H11 109.0 . . ?
C15 C16 C17 113.14(15) . . ?
H12 C16 H11 107.8 . . ?
C17 C16 H12 109.0 . . ?
C17 C16 H11 109.0 . . ?
C16 C17 H14 108.7 . . ?
C16 C17 H13 108.7 . . ?
H14 C17 H13 107.6 . . ?
C18 C17 C16 114.26(19) . . ?
C18 C17 H14 108.7 . . ?
C18 C17 H13 108.7 . . ?
C17 C18 H16A 108.5 . . ?
C17 C18 H15A 108.5 . . ?
C17 C18 H15B 107.5 . . ?
C17 C18 H16B 107.5 . . ?
H16A C18 H15A 107.5 . . ?
H15B C18 H16B 107.0 . . ?
C19A C18 C17 115.1(3) . . ?
C19A C18 H16A 108.5 . . ?
C19A C18 H15A 108.5 . . ?
C19B C18 C17 119.1(3) . . ?
C19B C18 H15B 107.5 . . ?
C19B C18 H16B 107.5 . . ?
C18 C19A H17A 109.5 . . ?
C18 C19A H18A 109.5 . . ?
C18 C19A H19A 109.5 . . ?
H17A C19A H18A 109.5 . . ?
H17A C19A H19A 109.5 . . ?
H18A C19A H19A 109.5 . . ?
C18 C19B H18B 109.5 . . ?
C18 C19B H19B 109.5 . . ?
C18 C19B H17B 109.5 . . ?
H18B C19B H19B 109.5 . . ?
H18B C19B H17B 109.5 . . ?
H19B C19B H17B 109.5 . . ?

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
C8 C10 C9 C8 -1.0(2) 2_576 . . . ?
C8 C10 C9 C4 179.83(12) 2_576 . . . ?
C8 C10 C11 C12 -179.91(13) 2_576 . . . ?
C8 C9 C4 C5 0.4(2) . . . . ?
C8 C9 C4 C3 -178.95(12) . . . . ?
C10 C8 C9 C10 1.0(2) 2_576 . . . ?
C10 C8 C9 C4 -179.83(12) 2_576 . . . ?
C10 C8 C7 C6 179.97(13) 2_576 . . . ?
C10 C9 C4 C5 179.55(12) . . . . ?
C10 C9 C4 C3 0.2(2) . . . . ?
C10 C11 C12 C3 -0.1(2) . . . . ?
C9 C8 C7 C6 -0.8(2) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C9 C4 C3 C12 0.4(2) . . . . ?
C9 C4 C3 C2 -179.37(12) . . . . ?
C5 C6 C7 C8 -0.7(2) . . . . ?
C5 C4 C3 C12 -178.90(13) . . . . ?
C5 C4 C3 C2 1.3(2) . . . . ?
C6 C5 C4 C9 -1.8(2) . . . . ?
C6 C5 C4 C3 177.52(13) . . . . ?
C6 C5 C1 O1 3.2(2) . . . . ?
C6 C5 C1 N1 -177.94(13) . . . . ?
C4 C5 C6 C7 2.0(2) . . . . ?
C4 C5 C1 O1 -176.63(13) . . . . ?
C4 C5 C1 N1 2.2(2) . . . . ?
C4 C3 C12 C11 -0.5(2) . . . . ?
C4 C3 C2 O2 179.64(15) . . . . ?
C4 C3 C2 N1 0.4(2) . . . . ?
C7 C8 C9 C10 -178.26(13) . . . . ?
C7 C8 C9 C4 0.9(2) . . . . ?
C1 N1 C2 O2 179.94(14) . . . . ?
C1 N1 C2 C3 -0.8(2) . . . . ?
C1 N1 C13 C14 86.54(17) . . . . ?
C1 C5 C6 C7 -177.86(13) . . . . ?
C1 C5 C4 C9 178.01(12) . . . . ?
C1 C5 C4 C3 -2.7(2) . . . . ?
C11 C10 C9 C8 178.36(13) . . . . ?
C11 C10 C9 C4 -0.8(2) . . . . ?
C12 C3 C2 O2 -0.2(3) . . . . ?
C12 C3 C2 N1 -179.36(13) . . . . ?
C2 N1 C1 O1 178.42(14) . . . . ?
C2 N1 C1 C5 -0.5(2) . . . . ?
C2 N1 C13 C14 -89.86(17) . . . . ?
C2 C3 C12 C11 179.29(14) . . . . ?
C15 C14 C13 N1 -172.16(14) . . . . ?
C15 C16 C17 C18 178.32(19) . . . . ?
C14 C15 C16 C17 -177.25(17) . . . . ?
C13 N1 C1 O1 2.3(2) . . . . ?
C13 N1 C1 C5 -176.58(12) . . . . ?
C13 N1 C2 O2 -3.9(2) . . . . ?
C13 N1 C2 C3 175.28(12) . . . . ?
C16 C15 C14 C13 175.88(15) . . . . ?
C16 C17 C18 C19A -80.8(3) . . . . ?
C16 C17 C18 C19B -163.4(4) . . . . ?

_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_PDI_C8_0_08GPa
_database_code_depnum_ccdc_archive 'CCDC 2493917'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C8_0_08GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.306 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT910_PDI_C8_0_08GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         88 Note   
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT088_PDI_C8_0_08GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.29 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C8_0_08GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01019 Ang.   
RESPONSE: These data come from high-pressure experiment and part of the 
reflections can not be collected, affecting bond precision. In addition, 
despite multiple attempts to grow better diffracting crystals, it was not 
successful.
;
_vrf_PLAT911_PDI_C8_0_08GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        812 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-02-14

_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C8
_chemical_name_systematic        N,N-Dioctyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C40 H42 N2 O4'
_chemical_formula_sum            'C40 H42 N2 O4'
_chemical_formula_weight         614.75
_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 -0.0004 0.0007 '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 -0.0003 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0008 0.0027 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.74670(10)
_cell_length_b                   8.5395(3)
_cell_length_c                   20.108(4)
_cell_angle_alpha                85.287(7)
_cell_angle_beta                 89.336(7)
_cell_angle_gamma                82.367(2)
_cell_volume                     805.12(16)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1248
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.9330
_cell_measurement_theta_min      5.3190
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.043
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.067
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.012
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.306
_diffrn_reflns_Laue_measured_fraction_max 0.194
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7240
_diffrn_reflns_point_group_measured_fraction_full 0.306
_diffrn_reflns_point_group_measured_fraction_max 0.194
_diffrn_reflns_theta_full        17.166
_diffrn_reflns_theta_max         22.990
_diffrn_reflns_theta_min         5.284
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.306
_diffrn_measured_fraction_theta_max 0.194
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     21.00  97.00   0.25    1.00  57.05   0.00-134.76    --   304
  2  φ     21.00  97.00   0.25    1.00  57.05   0.00-134.76    --   304
  3  φ     21.00  97.00   0.25    0.25  57.05   0.00-134.76    --   304
  4  φ     21.00  97.00   0.25    0.25  57.05   0.00-134.76    --   304
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.4919
_diffrn_source                   synchrotron
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 0.08(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                819
_reflns_number_total             1315
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.187
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1315
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.1166
_refine_ls_R_factor_gt           0.0882
_refine_ls_restrained_S_all      1.169
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2620
_refine_ls_wR_factor_ref         0.2993
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C10) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C17) \\sim Ueq,
Uanis(C1) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(C9) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C13) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(O1) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.04
3.a Secondary CH2 refined with riding coordinates:
 C16(H11,H12), C15(H9,H10), C17(H14,H13), C13(H5,H6), C14(H7,H8), C18(H16,H15),
  C19(H18,H17)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H3), C7(H2), C12(H4), C6(H1)
3.c Idealised Me refined as rotating group:
 C20(H20,H19,H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8457(6) 0.6919(4) 0.6815(5) 0.072(3) Uani 1 1 d . U . . .
O2 O 1.0036(5) 0.5214(3) 0.6033(4) 0.094(4) Uani 1 1 d . U . . .
C10 C 0.2005(6) 0.8697(3) 0.4810(5) 0.055(3) Uani 1 1 d . U . . .
C8 C 0.0183(6) 1.0528(4) 0.5666(5) 0.059(3) Uani 1 1 d . U . . .
O1 O 0.6776(7) 0.8564(5) 0.7603(6) 0.079(6) Uani 1 1 d . U . . .
C4 C 0.4259(6) 0.8470(4) 0.5905(5) 0.055(3) Uani 1 1 d . U . . .
C1 C 0.6597(8) 0.8192(6) 0.7013(7) 0.066(4) Uani 1 1 d . U . . .
C3 C 0.6227(6) 0.7185(4) 0.5708(5) 0.059(3) Uani 1 1 d . U . . .
C9 C 0.2137(6) 0.9228(3) 0.5443(5) 0.055(3) Uani 1 1 d . U . . .
C11 C 0.4025(6) 0.7441(3) 0.4631(4) 0.059(3) Uani 1 1 d . U . . .
H3 H 0.396604 0.708729 0.420641 0.071 Uiso 1 1 calc R U . . .
C2 C 0.8378(7) 0.6374(4) 0.6176(5) 0.065(3) Uani 1 1 d . U . . .
C5 C 0.4425(7) 0.8976(4) 0.6551(5) 0.061(3) Uani 1 1 d . U . . .
C7 C 0.0452(7) 1.1002(4) 0.6301(6) 0.066(3) Uani 1 1 d . U . . .
H2 H -0.079570 1.184965 0.643793 0.079 Uiso 1 1 calc R U . . .
C12 C 0.6103(6) 0.6723(4) 0.5077(5) 0.060(3) Uani 1 1 d . U . . .
H4 H 0.743784 0.591061 0.494375 0.071 Uiso 1 1 calc R U . . .
C6 C 0.2542(7) 1.0244(4) 0.6743(5) 0.069(3) Uani 1 1 d . U . . .
H1 H 0.267286 1.058927 0.716671 0.083 Uiso 1 1 calc R U . . .
C16 C 1.0030(10) 0.2115(5) 0.8403(6) 0.084(4) Uani 1 1 d . U . . .
H11 H 0.860538 0.250706 0.872007 0.101 Uiso 1 1 calc R U . . .
H12 H 0.906810 0.163104 0.806620 0.101 Uiso 1 1 calc R U . . .
C15 C 1.1319(8) 0.3524(5) 0.8066(6) 0.083(4) Uani 1 1 d . U . . .
H9 H 1.213171 0.407338 0.840521 0.099 Uiso 1 1 calc R U . . .
H10 H 1.284823 0.313430 0.777383 0.099 Uiso 1 1 calc R U . . .
C17 C 1.2127(10) 0.0852(5) 0.8764(6) 0.086(4) Uani 1 1 d . U . . .
H14 H 1.365346 0.052565 0.845943 0.104 Uiso 1 1 calc R U . . .
H13 H 1.295154 0.130325 0.913106 0.104 Uiso 1 1 calc R U . . .
C13 C 1.0484(8) 0.6016(4) 0.7307(6) 0.076(3) Uani 1 1 d . U . . .
H5 H 1.100159 0.671914 0.762706 0.091 Uiso 1 1 calc R U . . .
H6 H 1.219926 0.560019 0.707910 0.091 Uiso 1 1 calc R U . . .
C14 C 0.9208(8) 0.4677(5) 0.7668(6) 0.076(3) Uani 1 1 d . U . . .
H7 H 0.832191 0.411458 0.734438 0.091 Uiso 1 1 calc R U . . .
H8 H 0.773139 0.510731 0.796441 0.091 Uiso 1 1 calc R U . . .
C18 C 1.0842(12) -0.0573(6) 0.9030(7) 0.101(4) Uani 1 1 d . U . . .
H16 H 0.989459 -0.096972 0.866585 0.121 Uiso 1 1 calc R U . . .
H15 H 0.940063 -0.024893 0.935462 0.121 Uiso 1 1 calc R U . . .
C19 C 1.2896(16) -0.1917(7) 0.9354(9) 0.117(4) Uani 1 1 d . U . . .
H18 H 1.434919 -0.223768 0.903112 0.141 Uiso 1 1 calc R U . . .
H17 H 1.382800 -0.152718 0.972185 0.141 Uiso 1 1 calc R U . . .
C20 C 1.159(2) -0.3331(8) 0.9609(12) 0.160(11) Uani 1 1 d . U . . .
H20 H 1.008922 -0.348594 0.931416 0.239 Uiso 1 1 calc R U . . .
H19 H 1.081783 -0.317578 1.004635 0.239 Uiso 1 1 calc R U . . .
H21 H 1.300115 -0.424828 0.963273 0.239 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
N1 C1 1.388(7) . ?
N1 C2 1.405(13) . ?
N1 C13 1.483(11) . ?
O2 C2 1.231(5) . ?
C10 C8 1.473(10) 2_576 ?
C10 C9 1.391(14) . ?
C10 C11 1.408(5) . ?
C8 C9 1.446(6) . ?
C8 C7 1.383(15) . ?
O1 C1 1.258(18) . ?
C4 C3 1.423(6) . ?
C4 C9 1.430(10) . ?
C4 C5 1.409(15) . ?
C1 C5 1.454(13) . ?
C3 C2 1.461(10) . ?
C3 C12 1.363(14) . ?
C11 H3 0.9300 . ?
C11 C12 1.387(10) . ?
C5 C6 1.387(6) . ?
C7 H2 0.9300 . ?
C7 C6 1.395(11) . ?
C12 H4 0.9300 . ?
C6 H1 0.9300 . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C15 1.528(9) . ?
C16 C17 1.512(11) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C14 1.497(10) . ?
C17 H14 0.9700 . ?
C17 H13 0.9700 . ?
C17 C18 1.490(9) . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C13 C14 1.496(9) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C18 H16 0.9700 . ?
C18 H15 0.9700 . ?
C18 C19 1.512(13) . ?
C19 H18 0.9700 . ?
C19 H17 0.9700 . ?
C19 C20 1.483(11) . ?
C20 H20 0.9600 . ?
C20 H19 0.9600 . ?
C20 H21 0.9600 . ?

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 C2 122.7(7) . . ?
C1 N1 C13 119.3(9) . . ?
C2 N1 C13 117.9(4) . . ?
C9 C10 C8 120.0(4) . 2_576 ?
C9 C10 C11 119.0(6) . . ?
C11 C10 C8 121.1(8) . 2_576 ?
C9 C8 C10 117.3(9) . 2_576 ?
C7 C8 C10 123.0(4) . 2_576 ?
C7 C8 C9 119.7(7) . . ?
C3 C4 C9 119.4(9) . . ?
C5 C4 C3 119.6(7) . . ?
C5 C4 C9 121.0(4) . . ?
N1 C1 C5 119.2(10) . . ?
O1 C1 N1 118.1(9) . . ?
O1 C1 C5 122.7(6) . . ?
C4 C3 C2 120.3(9) . . ?
C12 C3 C4 119.4(7) . . ?
C12 C3 C2 120.2(5) . . ?
C10 C9 C8 122.8(7) . . ?
C10 C9 C4 119.8(4) . . ?
C4 C9 C8 117.4(9) . . ?
C10 C11 H3 119.5 . . ?
C12 C11 C10 121.0(8) . . ?
C12 C11 H3 119.5 . . ?
N1 C2 C3 118.0(4) . . ?
O2 C2 N1 119.8(7) . . ?
O2 C2 C3 122.2(9) . . ?
C4 C5 C1 120.2(5) . . ?
C6 C5 C4 120.0(7) . . ?
C6 C5 C1 119.8(9) . . ?
C8 C7 H2 119.1 . . ?
C8 C7 C6 121.8(5) . . ?
C6 C7 H2 119.1 . . ?
C3 C12 C11 121.3(4) . . ?
C3 C12 H4 119.3 . . ?
C11 C12 H4 119.3 . . ?
C5 C6 C7 120.1(9) . . ?
C5 C6 H1 119.9 . . ?
C7 C6 H1 119.9 . . ?
H11 C16 H12 107.5 . . ?
C15 C16 H11 108.5 . . ?
C15 C16 H12 108.5 . . ?
C17 C16 H11 108.5 . . ?
C17 C16 H12 108.5 . . ?
C17 C16 C15 115.1(4) . . ?
C16 C15 H9 108.9 . . ?
C16 C15 H10 108.9 . . ?
H9 C15 H10 107.7 . . ?
C14 C15 C16 113.2(3) . . ?
C14 C15 H9 108.9 . . ?
C14 C15 H10 108.9 . . ?
C16 C17 H14 108.8 . . ?
C16 C17 H13 108.8 . . ?
H14 C17 H13 107.7 . . ?
C18 C17 C16 113.6(4) . . ?
C18 C17 H14 108.8 . . ?
C18 C17 H13 108.8 . . ?
N1 C13 H5 109.4 . . ?
N1 C13 H6 109.4 . . ?
N1 C13 C14 111.0(3) . . ?
H5 C13 H6 108.0 . . ?
C14 C13 H5 109.4 . . ?
C14 C13 H6 109.4 . . ?
C15 C14 H7 108.9 . . ?
C15 C14 H8 108.9 . . ?
C13 C14 C15 113.6(3) . . ?
C13 C14 H7 108.9 . . ?
C13 C14 H8 108.9 . . ?
H7 C14 H8 107.7 . . ?
C17 C18 H16 108.4 . . ?
C17 C18 H15 108.4 . . ?
C17 C18 C19 115.5(4) . . ?
H16 C18 H15 107.5 . . ?
C19 C18 H16 108.4 . . ?
C19 C18 H15 108.4 . . ?
C18 C19 H18 108.6 . . ?
C18 C19 H17 108.6 . . ?
H18 C19 H17 107.5 . . ?
C20 C19 C18 114.8(6) . . ?
C20 C19 H18 108.6 . . ?
C20 C19 H17 108.6 . . ?
C19 C20 H20 109.5 . . ?
C19 C20 H19 109.5 . . ?
C19 C20 H21 109.5 . . ?
H20 C20 H19 109.5 . . ?
H20 C20 H21 109.5 . . ?
H19 C20 H21 109.5 . . ?

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
N1 C1 C5 C4 -1.5(9) . . . . ?
N1 C1 C5 C6 179.7(5) . . . . ?
N1 C13 C14 C15 168.1(7) . . . . ?
C10 C8 C9 C10 -0.4(8) 2_576 . . . ?
C10 C8 C9 C4 -179.9(3) 2_576 . . . ?
C10 C8 C7 C6 179.9(4) 2_576 . . . ?
C10 C11 C12 C3 1.3(7) . . . . ?
C8 C10 C9 C8 0.4(8) 2_576 . . . ?
C8 C10 C9 C4 179.9(3) 2_576 . . . ?
C8 C10 C11 C12 179.3(3) 2_576 . . . ?
C8 C7 C6 C5 -0.1(9) . . . . ?
O1 C1 C5 C4 -177.6(7) . . . . ?
O1 C1 C5 C6 3.5(11) . . . . ?
C4 C3 C2 N1 -1.0(7) . . . . ?
C4 C3 C2 O2 176.8(4) . . . . ?
C4 C3 C12 C11 -2.5(8) . . . . ?
C4 C5 C6 C7 1.1(8) . . . . ?
C1 N1 C2 O2 -178.2(4) . . . . ?
C1 N1 C2 C3 -0.4(8) . . . . ?
C1 N1 C13 C14 89.7(6) . . . . ?
C1 C5 C6 C7 -180.0(5) . . . . ?
C3 C4 C9 C10 0.4(7) . . . . ?
C3 C4 C9 C8 179.9(3) . . . . ?
C3 C4 C5 C1 0.1(9) . . . . ?
C3 C4 C5 C6 179.0(3) . . . . ?
C9 C10 C11 C12 0.8(7) . . . . ?
C9 C8 C7 C6 -1.0(9) . . . . ?
C9 C4 C3 C2 -178.8(3) . . . . ?
C9 C4 C3 C12 1.6(7) . . . . ?
C9 C4 C5 C1 180.0(4) . . . . ?
C9 C4 C5 C6 -1.1(8) . . . . ?
C11 C10 C9 C8 178.9(3) . . . . ?
C11 C10 C9 C4 -1.6(7) . . . . ?
C2 N1 C1 O1 177.9(6) . . . . ?
C2 N1 C1 C5 1.6(9) . . . . ?
C2 N1 C13 C14 -86.0(8) . . . . ?
C2 C3 C12 C11 177.9(3) . . . . ?
C5 C4 C3 C2 1.1(7) . . . . ?
C5 C4 C3 C12 -178.5(5) . . . . ?
C5 C4 C9 C10 -179.4(4) . . . . ?
C5 C4 C9 C8 0.1(7) . . . . ?
C7 C8 C9 C10 -179.5(5) . . . . ?
C7 C8 C9 C4 1.0(8) . . . . ?
C12 C3 C2 N1 178.6(5) . . . . ?
C12 C3 C2 O2 -3.6(7) . . . . ?
C16 C15 C14 C13 -177.0(7) . . . . ?
C16 C17 C18 C19 176.0(10) . . . . ?
C15 C16 C17 C18 -174.4(9) . . . . ?
C17 C16 C15 C14 175.2(9) . . . . ?
C17 C18 C19 C20 -179.4(12) . . . . ?
C13 N1 C1 O1 2.4(9) . . . . ?
C13 N1 C1 C5 -173.9(5) . . . . ?
C13 N1 C2 O2 -2.7(7) . . . . ?
C13 N1 C2 C3 175.2(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_PDI_C8_1_16GPa
_database_code_depnum_ccdc_archive 'CCDC 2493920'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C8_1_16GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.308 Why?
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C8_1_16GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.51 Note 
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT910_PDI_C8_1_16GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         89 Note
RESPONSE: The unit cell is reasonable large and these low angle 
reflections are probably missing due to the beamstop.
;
_vrf_PLAT911_PDI_C8_1_16GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        878 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-08-07

_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            PDI-C8
_chemical_name_systematic        N,N-Dioctyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C40 H42 N2 O4'
_chemical_formula_sum            'C40 H42 N2 O4'
_chemical_formula_weight         614.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N2O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0004 0.0007 '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 -0.0003 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0008 0.0027 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.4866(3)
_cell_length_b                   8.4612(5)
_cell_length_c                   19.429(2)
_cell_angle_alpha                80.771(10)
_cell_angle_beta                 87.690(10)
_cell_angle_gamma                84.078(5)
_cell_volume                     723.92(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1972
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.3910
_cell_measurement_theta_min      5.4730
_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  0.43619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.065
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.013
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.308
_diffrn_reflns_Laue_measured_fraction_max 0.181
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5857
_diffrn_reflns_point_group_measured_fraction_full 0.308
_diffrn_reflns_point_group_measured_fraction_max 0.181
_diffrn_reflns_theta_full        17.166
_diffrn_reflns_theta_max         23.391
_diffrn_reflns_theta_min         5.469
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.308
_diffrn_measured_fraction_theta_max 0.181
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     21.00  97.00   0.25    0.50  57.05   0.00-134.76    --   304
  2  φ     21.00  97.00   0.25    0.50  57.05   0.00-134.76    --   304
  3  φ     21.00  97.00   0.25    1.00  57.05   0.00-134.76    --   304
  4  φ     21.00  97.00   0.25    1.00  57.05   0.00-134.76    --   304
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0018354000
_diffrn_orient_matrix_UB_12      -0.0082838000
_diffrn_orient_matrix_UB_13      0.0256302000
_diffrn_orient_matrix_UB_21      -0.0570907000
_diffrn_orient_matrix_UB_22      -0.0469618000
_diffrn_orient_matrix_UB_23      0.0010165000
_diffrn_orient_matrix_UB_31      0.0943097000
_diffrn_orient_matrix_UB_32      -0.0350521000
_diffrn_orient_matrix_UB_33      -0.0006092000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.4919
_diffrn_source                   synchrotron
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 1.16(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                958
_reflns_number_total             1152
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.271
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1152
_refine_ls_number_restraints     138
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0845
_refine_ls_restrained_S_all      1.257
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2542
_refine_ls_wR_factor_ref         0.2657
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(C10) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C16) \\sim Ueq,
Uanis(C5) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(N1) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C7) \\sim Ueq,
Uanis(C20) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C3)
\\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
2.a Secondary CH2 refined with riding coordinates:
 C14(H7,H8), C13(H5,H6), C16(H11,H12), C15(H9,H10), C17(H13,H14), C19(H18,H17),
  C18(H15,H16)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H1), C7(H2), C12(H4), C11(H3)
2.c Idealised Me refined as rotating group:
 C20(H20,H21,H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0047(4) 0.5121(3) 0.3904(3) 0.067(3) Uani 1 1 d . U . . .
N1 N 0.1463(5) 0.3506(3) 0.3112(4) 0.046(3) Uani 1 1 d . U . . .
C10 C 0.9787(5) -0.0403(3) 0.4309(4) 0.039(3) Uani 1 1 d . U . . .
C8 C 0.7987(5) 0.1288(3) 0.5202(4) 0.042(3) Uani 1 1 d . U . . .
O2 O 0.3031(5) 0.1931(3) 0.2293(4) 0.068(4) Uani 1 1 d . U . . .
C9 C 0.7872(5) 0.0881(3) 0.4528(4) 0.037(3) Uani 1 1 d . U . . .
C5 C 0.3770(5) 0.3017(3) 0.4250(4) 0.039(3) Uani 1 1 d . U . . .
C2 C 0.3294(6) 0.2234(4) 0.2892(5) 0.040(3) Uani 1 1 d . U . . .
C4 C 0.5710(5) 0.1745(3) 0.4044(4) 0.038(3) Uani 1 1 d . U . . .
C1 C 0.1587(6) 0.3955(3) 0.3753(4) 0.048(3) Uani 1 1 d . U . . .
C6 C 0.3857(6) 0.3363(3) 0.4941(4) 0.045(3) Uani 1 1 d . U . . .
H1 H 0.2491 0.4149 0.5089 0.054 Uiso 1 1 calc R U . . .
C7 C 0.5971(5) 0.2528(3) 0.5387(4) 0.043(3) Uani 1 1 d . U . . .
H2 H 0.6065 0.2799 0.5831 0.052 Uiso 1 1 calc R U . . .
C14 C 0.0984(5) 0.5940(3) 0.2220(4) 0.058(3) Uani 1 1 d . U . . .
H7 H 0.2044 0.6393 0.2555 0.070 Uiso 1 1 calc R U . . .
H8 H 0.2458 0.5549 0.1892 0.070 Uiso 1 1 calc R U . . .
C3 C 0.5512(6) 0.1353(3) 0.3373(4) 0.042(3) Uani 1 1 d . U . . .
C12 C 0.7382(6) 0.0084(3) 0.3177(4) 0.045(3) Uani 1 1 d . U . . .
H4 H 0.7208 -0.0196 0.2738 0.054 Uiso 1 1 calc R U . . .
C11 C 0.9500(6) -0.0769(3) 0.3625(5) 0.048(3) Uani 1 1 d . U . . .
H3 H 1.0764 -0.1598 0.3478 0.057 Uiso 1 1 calc R U . . .
C13 C -0.0573(6) 0.4524(3) 0.2602(4) 0.045(3) Uani 1 1 d . U . . .
H5 H -0.2363 0.4920 0.2843 0.053 Uiso 1 1 calc R U . . .
H6 H -0.1174 0.3886 0.2268 0.053 Uiso 1 1 calc R U . . .
C16 C 0.0490(6) 0.8683(3) 0.1489(4) 0.054(3) Uani 1 1 d . U . . .
H11 H 0.1549 0.9069 0.1845 0.065 Uiso 1 1 calc R U . . .
H12 H 0.1970 0.8325 0.1155 0.065 Uiso 1 1 calc R U . . .
C15 C -0.1137(6) 0.7255(3) 0.1828(4) 0.048(3) Uani 1 1 d . U . . .
H9 H -0.2677 0.7614 0.2149 0.057 Uiso 1 1 calc R U . . .
H10 H -0.2110 0.6826 0.1472 0.057 Uiso 1 1 calc R U . . .
C17 C -0.1573(6) 1.0067(3) 0.1119(4) 0.053(3) Uani 1 1 d . U . . .
H13 H -0.2797 1.0566 0.1463 0.064 Uiso 1 1 calc R U . . .
H14 H -0.2902 0.9651 0.0825 0.064 Uiso 1 1 calc R U . . .
C19 C -0.1808(9) 1.2804(4) 0.0325(5) 0.069(3) Uani 1 1 d . U . . .
H18 H -0.0652 1.3419 -0.0036 0.083 Uiso 1 1 calc R U . . .
H17 H -0.3449 1.2436 0.0103 0.083 Uiso 1 1 calc R U . . .
C18 C 0.0182(8) 1.1348(4) 0.0667(5) 0.060(3) Uani 1 1 d . U . . .
H15 H 0.1607 1.1706 0.0957 0.072 Uiso 1 1 calc R U . . .
H16 H 0.1310 1.0858 0.0306 0.072 Uiso 1 1 calc R U . . .
C20 C -0.3092(13) 1.3900(5) 0.0836(6) 0.082(5) Uani 1 1 d . U . . .
H20 H -0.4332 1.4789 0.0591 0.123 Uiso 1 1 calc R U . . .
H21 H -0.1483 1.4296 0.1048 0.123 Uiso 1 1 calc R U . . .
H19 H -0.4271 1.3306 0.1190 0.123 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 1.235(4) . ?
N1 C2 1.397(5) . ?
N1 C1 1.364(11) . ?
N1 C13 1.481(8) . ?
C10 C8 1.468(8) 2_756 ?
C10 C9 1.424(5) . ?
C10 C11 1.425(12) . ?
C8 C10 1.468(8) 2_756 ?
C8 C9 1.410(12) . ?
C8 C7 1.396(5) . ?
O2 C2 1.244(11) . ?
C9 C4 1.438(8) . ?
C5 C4 1.412(5) . ?
C5 C1 1.481(8) . ?
C5 C6 1.421(12) . ?
C2 C3 1.456(9) . ?
C4 C3 1.403(13) . ?
C6 H1 0.9300 . ?
C6 C7 1.371(7) . ?
C7 H2 0.9300 . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C13 1.523(5) . ?
C14 C15 1.513(6) . ?
C3 C12 1.386(5) . ?
C12 H4 0.9300 . ?
C12 C11 1.380(8) . ?
C11 H3 0.9300 . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C15 1.521(5) . ?
C16 C17 1.518(6) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C18 1.543(7) . ?
C19 H18 0.9700 . ?
C19 H17 0.9700 . ?
C19 C18 1.521(7) . ?
C19 C20 1.522(11) . ?
C18 H15 0.9700 . ?
C18 H16 0.9700 . ?
C20 H20 0.9600 . ?
C20 H21 0.9600 . ?
C20 H19 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C13 118.5(7) . . ?
C1 N1 C2 124.1(6) . . ?
C1 N1 C13 117.2(3) . . ?
C9 C10 C8 118.2(7) . 2_756 ?
C11 C10 C8 122.6(4) . 2_756 ?
C11 C10 C9 119.2(5) . . ?
C9 C8 C10 119.5(4) . 2_756 ?
C9 C8 C7 119.0(5) . . ?
C7 C8 C10 121.5(7) . 2_756 ?
C10 C9 C4 117.8(7) . . ?
C8 C9 C10 122.2(5) . . ?
C8 C9 C4 119.9(4) . . ?
C4 C5 C1 119.8(7) . . ?
C6 C5 C4 119.9(6) . . ?
C6 C5 C1 120.2(4) . . ?
N1 C2 C3 117.9(7) . . ?
O2 C2 N1 119.2(6) . . ?
O2 C2 C3 122.8(4) . . ?
C5 C4 C9 118.9(7) . . ?
C3 C4 C9 121.3(4) . . ?
C3 C4 C5 119.8(5) . . ?
O1 C1 N1 120.6(6) . . ?
O1 C1 C5 121.6(7) . . ?
N1 C1 C5 117.8(4) . . ?
C5 C6 H1 120.2 . . ?
C5 C6 C7 119.5(3) . . ?
C7 C6 H1 120.2 . . ?
C8 C7 H2 118.7 . . ?
C6 C7 C8 122.6(6) . . ?
C6 C7 H2 118.7 . . ?
H7 C14 H8 107.7 . . ?
C13 C14 H7 108.8 . . ?
C13 C14 H8 108.8 . . ?
C15 C14 H7 108.8 . . ?
C15 C14 H8 108.8 . . ?
C15 C14 C13 113.7(2) . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 C12 119.6(6) . . ?
C12 C3 C2 119.9(7) . . ?
C3 C12 H4 119.6 . . ?
C3 C12 C11 120.9(7) . . ?
C11 C12 H4 119.6 . . ?
C10 C11 H3 119.4 . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H3 119.4 . . ?
N1 C13 C14 110.4(2) . . ?
N1 C13 H5 109.6 . . ?
N1 C13 H6 109.6 . . ?
C14 C13 H5 109.6 . . ?
C14 C13 H6 109.6 . . ?
H5 C13 H6 108.1 . . ?
H11 C16 H12 107.7 . . ?
C15 C16 H11 108.8 . . ?
C15 C16 H12 108.8 . . ?
C17 C16 H11 108.8 . . ?
C17 C16 H12 108.8 . . ?
C17 C16 C15 113.6(2) . . ?
C14 C15 C16 111.8(2) . . ?
C14 C15 H9 109.3 . . ?
C14 C15 H10 109.3 . . ?
C16 C15 H9 109.3 . . ?
C16 C15 H10 109.3 . . ?
H9 C15 H10 107.9 . . ?
C16 C17 H13 109.2 . . ?
C16 C17 H14 109.2 . . ?
C16 C17 C18 112.2(3) . . ?
H13 C17 H14 107.9 . . ?
C18 C17 H13 109.2 . . ?
C18 C17 H14 109.2 . . ?
H18 C19 H17 107.7 . . ?
C18 C19 H18 108.9 . . ?
C18 C19 H17 108.9 . . ?
C20 C19 H18 108.9 . . ?
C20 C19 H17 108.9 . . ?
C20 C19 C18 113.3(8) . . ?
C17 C18 H15 108.9 . . ?
C17 C18 H16 108.9 . . ?
C19 C18 C17 113.5(3) . . ?
C19 C18 H15 108.9 . . ?
C19 C18 H16 108.9 . . ?
H15 C18 H16 107.7 . . ?
C19 C20 H20 109.5 . . ?
C19 C20 H21 109.5 . . ?
C19 C20 H19 109.5 . . ?
H20 C20 H21 109.5 . . ?
H20 C20 H19 109.5 . . ?
H21 C20 H19 109.5 . . ?

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
N1 C2 C3 C4 2.2(7) . . . . ?
N1 C2 C3 C12 -179.8(3) . . . . ?
C10 C8 C9 C10 2.0(7) 2_756 . . . ?
C10 C8 C9 C4 -179.7(2) 2_756 . . . ?
C10 C8 C7 C6 -179.4(3) 2_756 . . . ?
C10 C9 C4 C5 179.6(3) . . . . ?
C10 C9 C4 C3 -0.8(7) . . . . ?
C8 C10 C9 C8 -2.0(7) 2_756 . . . ?
C8 C10 C9 C4 179.7(2) 2_756 . . . ?
C8 C10 C11 C12 179.9(3) 2_756 . . . ?
C8 C9 C4 C5 1.3(6) . . . . ?
C8 C9 C4 C3 -179.1(3) . . . . ?
O2 C2 C3 C4 180.0(4) . . . . ?
O2 C2 C3 C12 -2.0(7) . . . . ?
C9 C10 C11 C12 -0.8(7) . . . . ?
C9 C8 C7 C6 0.5(6) . . . . ?
C9 C4 C3 C2 179.5(3) . . . . ?
C9 C4 C3 C12 1.6(7) . . . . ?
C5 C4 C3 C2 -0.8(7) . . . . ?
C5 C4 C3 C12 -178.8(2) . . . . ?
C5 C6 C7 C8 -2.9(5) . . . . ?
C2 N1 C1 O1 178.0(3) . . . . ?
C2 N1 C1 C5 -1.0(6) . . . . ?
C2 N1 C13 C14 -90.4(4) . . . . ?
C2 C3 C12 C11 -179.9(3) . . . . ?
C4 C5 C1 O1 -176.6(3) . . . . ?
C4 C5 C1 N1 2.4(6) . . . . ?
C4 C5 C6 C7 4.5(6) . . . . ?
C4 C3 C12 C11 -2.0(6) . . . . ?
C1 N1 C2 O2 -179.2(4) . . . . ?
C1 N1 C2 C3 -1.3(7) . . . . ?
C1 N1 C13 C14 84.7(5) . . . . ?
C1 C5 C4 C9 178.2(3) . . . . ?
C1 C5 C4 C3 -1.5(6) . . . . ?
C1 C5 C6 C7 -177.4(2) . . . . ?
C6 C5 C4 C9 -3.7(6) . . . . ?
C6 C5 C4 C3 176.7(3) . . . . ?
C6 C5 C1 O1 5.2(6) . . . . ?
C6 C5 C1 N1 -175.8(3) . . . . ?
C7 C8 C9 C10 -177.9(2) . . . . ?
C7 C8 C9 C4 0.3(6) . . . . ?
C3 C12 C11 C10 1.6(6) . . . . ?
C11 C10 C9 C8 178.6(3) . . . . ?
C11 C10 C9 C4 0.4(6) . . . . ?
C13 N1 C2 O2 -4.4(6) . . . . ?
C13 N1 C2 C3 173.5(3) . . . . ?
C13 N1 C1 O1 3.2(6) . . . . ?
C13 N1 C1 C5 -175.8(2) . . . . ?
C13 C14 C15 C16 176.8(5) . . . . ?
C16 C17 C18 C19 -176.3(6) . . . . ?
C15 C14 C13 N1 -165.3(5) . . . . ?
C15 C16 C17 C18 -169.2(5) . . . . ?
C17 C16 C15 C14 -177.3(5) . . . . ?
C20 C19 C18 C17 72.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.970
_oxdiff_exptl_absorpt_empirical_full_min 0.166
####################################################################### 
# 
# 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_PDI_C7_270K
_database_code_depnum_ccdc_archive 'CCDC 2493911'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
_audit_creation_date             2025-03-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        'N,N Diheptyl 3,4,9,10 perylenedicarboximide'
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8251(4)
_cell_length_b                   8.3440(7)
_cell_length_c                   19.1997(17)
_cell_angle_alpha                79.494(5)
_cell_angle_beta                 89.114(5)
_cell_angle_gamma                81.836(5)
_cell_volume                     752.29(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3730
_cell_measurement_temperature    270.00
_cell_measurement_theta_max      72.682
_cell_measurement_theta_min      2.340
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.803
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1305 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.8120.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.034
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21576
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.714
_diffrn_reflns_theta_min         4.685
_diffrn_ambient_temperature      270.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 Data were collected at low temperature of 270 K.
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1995
_reflns_number_total             2920
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.210
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.047
_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)+(0.0814P)²+0.1745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1682
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C19A-C18 \\sim C19B-C18
 with sigma of 0.02
2. Rigid body (RIGU) restrains
 C19A, C19B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(H15B)=Sof(H16B)=Sof(C19B)=Sof(H18B)=Sof(H19B)=Sof(H17B)=1-FVAR(1)
 Sof(H16A)=Sof(H15A)=Sof(C19A)=Sof(H17A)=Sof(H18A)=Sof(H19A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C13(H5,H6), C15(H9,H10), C14(H8,H7), C16(H11,H12), C17(H13,H14), C18(H16A,
 H15A), C18(H15B,H16B)
4.b Me refined with riding coordinates:
 C19A(H17A,H18A,H19A), C19B(H18B,H19B,H17B)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H2), C6(H1), C11(H3), C12(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0063(3) 0.59021(18) 0.38821(8) 0.0545(4) Uani 1 1 d . . . . .
O2 O 0.6666(3) 1.0380(2) 0.22587(8) 0.0660(5) Uani 1 1 d . . . . .
N1 N 0.8386(3) 0.8143(2) 0.30713(8) 0.0434(4) Uani 1 1 d . . . . .
C9 C 0.2106(3) 0.9537(2) 0.45169(9) 0.0330(4) Uani 1 1 d . . . . .
C10 C 0.0125(3) 1.0979(2) 0.42991(9) 0.0339(4) Uani 1 1 d . . . . .
C8 C 0.2064(3) 0.8555(2) 0.52036(9) 0.0341(4) Uani 1 1 d . . . . .
C5 C 0.6227(3) 0.7666(2) 0.42390(9) 0.0364(4) Uani 1 1 d . . . . .
C4 C 0.4226(3) 0.9083(2) 0.40331(9) 0.0346(4) Uani 1 1 d . . . . .
C7 C 0.4106(3) 0.7193(2) 0.53841(9) 0.0376(4) Uani 1 1 d . . . . .
H2 H 0.409332 0.655062 0.583381 0.045 Uiso 1 1 calc R U . . .
C6 C 0.6178(3) 0.6762(2) 0.49083(10) 0.0387(4) Uani 1 1 d . . . . .
H1 H 0.753342 0.585365 0.504775 0.046 Uiso 1 1 calc R U . . .
C3 C 0.4332(4) 1.0054(2) 0.33573(9) 0.0396(4) Uani 1 1 d . . . . .
C1 C 0.8373(4) 0.7159(2) 0.37337(10) 0.0415(4) Uani 1 1 d . . . . .
C11 C 0.0336(4) 1.1900(2) 0.36302(10) 0.0427(5) Uani 1 1 d . . . . .
H3 H -0.093853 1.284642 0.348830 0.051 Uiso 1 1 calc R U . . .
C12 C 0.2418(4) 1.1444(2) 0.31621(10) 0.0439(5) Uani 1 1 d . . . . .
H4 H 0.250958 1.208683 0.271472 0.053 Uiso 1 1 calc R U . . .
C2 C 0.6510(4) 0.9585(3) 0.28480(10) 0.0443(5) Uani 1 1 d . . . . .
C13 C 1.0412(4) 0.7585(3) 0.25511(10) 0.0488(5) Uani 1 1 d . . . . .
H5 H 1.211667 0.702037 0.279641 0.059 Uiso 1 1 calc R U . . .
H6 H 1.088267 0.853395 0.222278 0.059 Uiso 1 1 calc R U . . .
C15 C 1.1395(4) 0.5660(3) 0.16682(11) 0.0572(6) Uani 1 1 d . . . . .
H9 H 1.301752 0.511863 0.195408 0.069 Uiso 1 1 calc R U . . .
H10 H 1.199794 0.652464 0.131481 0.069 Uiso 1 1 calc R U . . .
C14 C 0.9241(4) 0.6433(3) 0.21402(11) 0.0545(6) Uani 1 1 d . . . . .
H8 H 0.767660 0.704282 0.184939 0.065 Uiso 1 1 calc R U . . .
H7 H 0.853878 0.556527 0.247248 0.065 Uiso 1 1 calc R U . . .
C16 C 1.0299(5) 0.4411(3) 0.12936(12) 0.0608(6) Uani 1 1 d . . . . .
H11 H 0.961284 0.357423 0.164572 0.073 Uiso 1 1 calc R U . . .
H12 H 0.873229 0.496395 0.098989 0.073 Uiso 1 1 calc R U . . .
C17 C 1.2486(6) 0.3584(4) 0.08512(15) 0.0811(8) Uani 1 1 d . . . . .
H13 H 1.406262 0.304864 0.115520 0.097 Uiso 1 1 calc R U . . .
H14 H 1.315435 0.442358 0.049716 0.097 Uiso 1 1 calc R U . . .
C18 C 1.1460(8) 0.2313(5) 0.0478(2) 0.1108(12) Uani 1 1 d D . . . .
H16A H 0.958077 0.273161 0.029647 0.133 Uiso 0.545(7) 1 calc R U P A 1
H15A H 1.265493 0.217504 0.007602 0.133 Uiso 0.545(7) 1 calc R U P A 1
H15B H 1.021937 0.172813 0.080051 0.133 Uiso 0.455(7) 1 calc R U P A 2
H16B H 1.032860 0.291019 0.007469 0.133 Uiso 0.455(7) 1 calc R U P A 2
C19A C 1.1427(13) 0.0870(8) 0.0882(3) 0.084(2) Uani 0.545(7) 1 d D . P A 1
H17A H 1.076118 0.013690 0.061242 0.127 Uiso 0.545(7) 1 calc R U P A 1
H18A H 1.328739 0.042882 0.105460 0.127 Uiso 0.545(7) 1 calc R U P A 1
H19A H 1.020950 0.098606 0.127532 0.127 Uiso 0.545(7) 1 calc R U P A 1
C19B C 1.3371(18) 0.1140(13) 0.0235(6) 0.156(6) Uani 0.455(7) 1 d D . P A 2
H18B H 1.238760 0.043929 0.001434 0.233 Uiso 0.455(7) 1 calc R U P A 2
H19B H 1.458001 0.167861 -0.010398 0.233 Uiso 0.455(7) 1 calc R U P A 2
H17B H 1.447014 0.048957 0.062612 0.233 Uiso 0.455(7) 1 calc R U P A 2


_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 1.226(2) . ?
O2 C2 1.210(2) . ?
N1 C1 1.383(2) . ?
N1 C2 1.402(3) . ?
N1 C13 1.477(2) . ?
C9 C10 1.428(2) . ?
C9 C8 1.421(2) . ?
C9 C4 1.429(2) . ?
C10 C8 1.472(2) 2_576 ?
C10 C11 1.381(2) . ?
C8 C7 1.390(2) . ?
C5 C4 1.415(2) . ?
C5 C6 1.368(2) . ?
C5 C1 1.479(3) . ?
C4 C3 1.403(2) . ?
C7 H2 0.9300 . ?
C7 C6 1.397(3) . ?
C6 H1 0.9300 . ?
C3 C12 1.374(3) . ?
C3 C2 1.485(3) . ?
C11 H3 0.9300 . ?
C11 C12 1.396(3) . ?
C12 H4 0.9300 . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C13 C14 1.520(3) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C14 1.520(3) . ?
C15 C16 1.524(3) . ?
C14 H8 0.9700 . ?
C14 H7 0.9700 . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C17 1.513(3) . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C18 1.524(4) . ?
C18 H16A 0.9700 . ?
C18 H15A 0.9700 . ?
C18 H15B 0.9700 . ?
C18 H16B 0.9700 . ?
C18 C19A 1.310(6) . ?
C18 C19B 1.387(8) . ?
C19A H17A 0.9600 . ?
C19A H18A 0.9600 . ?
C19A H19A 0.9600 . ?
C19B H18B 0.9600 . ?
C19B H19B 0.9600 . ?
C19B H17B 0.9600 . ?

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 C2 124.47(16) . . ?
C1 N1 C13 117.62(16) . . ?
C2 N1 C13 117.81(16) . . ?
C10 C9 C4 118.94(15) . . ?
C8 C9 C10 122.08(16) . . ?
C8 C9 C4 118.97(16) . . ?
C9 C10 C8 118.96(15) . 2_576 ?
C11 C10 C9 118.96(16) . . ?
C11 C10 C8 122.08(16) . 2_576 ?
C9 C8 C10 118.95(16) . 2_576 ?
C7 C8 C9 118.81(16) . . ?
C7 C8 C10 122.24(16) . 2_576 ?
C4 C5 C1 120.27(16) . . ?
C6 C5 C4 119.89(16) . . ?
C6 C5 C1 119.85(16) . . ?
C5 C4 C9 119.97(16) . . ?
C3 C4 C9 119.81(16) . . ?
C3 C4 C5 120.21(16) . . ?
C8 C7 H2 119.1 . . ?
C8 C7 C6 121.80(17) . . ?
C6 C7 H2 119.1 . . ?
C5 C6 C7 120.52(16) . . ?
C5 C6 H1 119.7 . . ?
C7 C6 H1 119.7 . . ?
C4 C3 C2 120.28(17) . . ?
C12 C3 C4 120.19(17) . . ?
C12 C3 C2 119.54(16) . . ?
O1 C1 N1 120.28(17) . . ?
O1 C1 C5 122.14(18) . . ?
N1 C1 C5 117.57(16) . . ?
C10 C11 H3 119.2 . . ?
C10 C11 C12 121.59(17) . . ?
C12 C11 H3 119.2 . . ?
C3 C12 C11 120.52(17) . . ?
C3 C12 H4 119.7 . . ?
C11 C12 H4 119.7 . . ?
O2 C2 N1 120.38(18) . . ?
O2 C2 C3 122.46(18) . . ?
N1 C2 C3 117.15(16) . . ?
N1 C13 H5 109.3 . . ?
N1 C13 H6 109.3 . . ?
N1 C13 C14 111.61(15) . . ?
H5 C13 H6 108.0 . . ?
C14 C13 H5 109.3 . . ?
C14 C13 H6 109.3 . . ?
H9 C15 H10 107.7 . . ?
C14 C15 H9 108.9 . . ?
C14 C15 H10 108.9 . . ?
C14 C15 C16 113.46(17) . . ?
C16 C15 H9 108.9 . . ?
C16 C15 H10 108.9 . . ?
C13 C14 C15 113.06(16) . . ?
C13 C14 H8 109.0 . . ?
C13 C14 H7 109.0 . . ?
C15 C14 H8 109.0 . . ?
C15 C14 H7 109.0 . . ?
H8 C14 H7 107.8 . . ?
C15 C16 H11 108.9 . . ?
C15 C16 H12 108.9 . . ?
H11 C16 H12 107.7 . . ?
C17 C16 C15 113.37(19) . . ?
C17 C16 H11 108.9 . . ?
C17 C16 H12 108.9 . . ?
C16 C17 H13 108.6 . . ?
C16 C17 H14 108.6 . . ?
C16 C17 C18 114.5(3) . . ?
H13 C17 H14 107.6 . . ?
C18 C17 H13 108.6 . . ?
C18 C17 H14 108.6 . . ?
C17 C18 H16A 108.7 . . ?
C17 C18 H15A 108.7 . . ?
C17 C18 H15B 107.3 . . ?
C17 C18 H16B 107.3 . . ?
H16A C18 H15A 107.6 . . ?
H15B C18 H16B 106.9 . . ?
C19A C18 C17 114.2(4) . . ?
C19A C18 H16A 108.7 . . ?
C19A C18 H15A 108.7 . . ?
C19B C18 C17 120.0(5) . . ?
C19B C18 H15B 107.3 . . ?
C19B C18 H16B 107.3 . . ?
C18 C19A H17A 109.5 . . ?
C18 C19A H18A 109.5 . . ?
C18 C19A H19A 109.5 . . ?
H17A C19A H18A 109.5 . . ?
H17A C19A H19A 109.5 . . ?
H18A C19A H19A 109.5 . . ?
C18 C19B H18B 109.5 . . ?
C18 C19B H19B 109.5 . . ?
C18 C19B H17B 109.5 . . ?
H18B C19B H19B 109.5 . . ?
H18B C19B H17B 109.5 . . ?
H19B C19B H17B 109.5 . . ?

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
N1 C13 C14 C15 -172.59(18) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C9 C8 C7 C6 -0.4(2) . . . . ?
C9 C4 C3 C12 0.4(3) . . . . ?
C9 C4 C3 C2 -179.46(15) . . . . ?
C10 C9 C8 C10 1.3(3) . . . 2_576 ?
C10 C9 C8 C7 -178.31(15) . . . . ?
C10 C9 C4 C5 179.47(14) . . . . ?
C10 C9 C4 C3 0.1(2) . . . . ?
C10 C8 C7 C6 -179.93(15) 2_576 . . . ?
C10 C11 C12 C3 -0.1(3) . . . . ?
C8 C9 C10 C8 -1.3(3) . . . 2_576 ?
C8 C9 C10 C11 178.27(15) . . . . ?
C8 C9 C4 C5 0.5(2) . . . . ?
C8 C9 C4 C3 -178.83(14) . . . . ?
C8 C10 C11 C12 -179.84(16) 2_576 . . . ?
C8 C7 C6 C5 -1.1(3) . . . . ?
C5 C4 C3 C12 -178.89(16) . . . . ?
C5 C4 C3 C2 1.2(3) . . . . ?
C4 C9 C10 C8 179.81(14) . . . 2_576 ?
C4 C9 C10 C11 -0.7(2) . . . . ?
C4 C9 C8 C10 -179.81(14) . . . 2_576 ?
C4 C9 C8 C7 0.6(2) . . . . ?
C4 C5 C6 C7 2.2(3) . . . . ?
C4 C5 C1 O1 -176.77(16) . . . . ?
C4 C5 C1 N1 1.9(2) . . . . ?
C4 C3 C12 C11 -0.5(3) . . . . ?
C4 C3 C2 O2 179.44(18) . . . . ?
C4 C3 C2 N1 0.7(3) . . . . ?
C6 C5 C4 C9 -1.9(2) . . . . ?
C6 C5 C4 C3 177.41(15) . . . . ?
C6 C5 C1 O1 3.2(3) . . . . ?
C6 C5 C1 N1 -178.04(15) . . . . ?
C1 N1 C2 O2 179.88(18) . . . . ?
C1 N1 C2 C3 -1.4(3) . . . . ?
C1 N1 C13 C14 86.7(2) . . . . ?
C1 C5 C4 C9 178.10(14) . . . . ?
C1 C5 C4 C3 -2.6(2) . . . . ?
C1 C5 C6 C7 -177.83(15) . . . . ?
C12 C3 C2 O2 -0.5(3) . . . . ?
C12 C3 C2 N1 -179.16(16) . . . . ?
C2 N1 C1 O1 178.82(17) . . . . ?
C2 N1 C1 C5 0.1(3) . . . . ?
C2 N1 C13 C14 -89.9(2) . . . . ?
C2 C3 C12 C11 179.42(17) . . . . ?
C13 N1 C1 O1 2.5(3) . . . . ?
C13 N1 C1 C5 -176.28(15) . . . . ?
C13 N1 C2 O2 -3.8(3) . . . . ?
C13 N1 C2 C3 174.97(15) . . . . ?
C15 C16 C17 C18 179.3(3) . . . . ?
C14 C15 C16 C17 -177.3(2) . . . . ?
C16 C15 C14 C13 175.94(19) . . . . ?
C16 C17 C18 C19A -81.0(5) . . . . ?
C16 C17 C18 C19B -161.0(7) . . . . ?

_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_PDI_C8_1_57GPa
_database_code_depnum_ccdc_archive 'CCDC 2493922'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C8_1_57GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.307 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C8_1_57GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.39 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT340_PDI_C8_1_57GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01233 Ang.   
RESPONSE: These data come from high-pressure experiment and part of the 
reflections can not be collected, affecting bond precision. In addition, 
despite multiple attempts to grow better diffracting crystals, it was not 
successful.
;
_vrf_PLAT910_PDI_C8_1_57GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         163 Note   
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT911_PDI_C8_1_57GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        2482 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-02-25

_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C8
_chemical_name_systematic        N,N-Dioctyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C40 H42 N2 O4'
_chemical_formula_sum            'C40 H42 N2 O4'
_chemical_formula_weight         614.75
_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 -0.0004 0.0007 '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 -0.0003 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0008 0.0027 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.50300(10)
_cell_length_b                   16.9388(6)
_cell_length_c                   18.982(3)
_cell_angle_alpha                76.548(6)
_cell_angle_beta                 89.101(6)
_cell_angle_gamma                83.403(3)
_cell_volume                     1398.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1293
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.8310
_cell_measurement_theta_min      5.5340
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.997
_exptl_absorpt_coefficient_mu    0.049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.064
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.013
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.307
_diffrn_reflns_Laue_measured_fraction_max 0.187
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6206
_diffrn_reflns_point_group_measured_fraction_full 0.307
_diffrn_reflns_point_group_measured_fraction_max 0.187
_diffrn_reflns_theta_full        17.166
_diffrn_reflns_theta_max         23.178
_diffrn_reflns_theta_min         5.363
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.307
_diffrn_measured_fraction_theta_max 0.187
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     21.00  97.00   0.25    1.00  57.05   0.00-134.76    --   304
  2  φ     21.00  97.00   0.25    1.00  57.05   0.00-134.76    --   304
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.4919
_diffrn_source                   synchrotron
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 1.57(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1444
_reflns_number_total             2247
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.260
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         2247
_refine_ls_number_restraints     241
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0952
_refine_ls_restrained_S_all      1.156
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2582
_refine_ls_wR_factor_ref         0.2950
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid bond restraints
 O4, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
2. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C4)
\\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C3) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C10)
\\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C23) \\sim Ueq,
Uanis(C33) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C21)
\\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C9) \\sim Ueq,
Uanis(C28) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C35)
\\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C26) \\sim Ueq,
Uanis(C29) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C19) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C39)
\\sim Ueq, Uanis(C32) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C34(H28,H29), C36(H32,H33), C35(H31,H30), C17(H13,H14), C15(H9,H10), C14(H7,
 H8), C33(H27,H26), C13(H6,H5), C16(H11,H12), C37(H34,H35), C19(H17,H18),
 C18(H15,H16), C38(H36,H37), C39(H38,H39)
3.b Aromatic/amide H refined with riding coordinates:
 C27(H23), C7(H2), C26(H22), C6(H1), C11(H3), C31(H24), C12(H4), C32(H25)
3.c Idealised Me refined as rotating group:
 C40(H40,H41,H42), C20(H19,H20,H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.3642(7) 0.6663(2) 0.3115(6) 0.046(5) Uani 1 1 d . . . . .
C5 C 0.9522(9) 0.7595(3) 0.3412(7) 0.032(3) Uani 1 1 d . U . . .
C4 C 0.9233(8) 0.7078(3) 0.4065(7) 0.030(3) Uani 1 1 d . U . . .
O4 O -0.2696(7) 0.7100(3) 0.7806(6) 0.064(4) Uani 1 1 d . U . . .
N2 N -0.4027(7) 0.8314(2) 0.6991(6) 0.037(5) Uani 1 1 d . . . . .
O2 O 1.5116(7) 0.5469(2) 0.3923(5) 0.070(6) Uani 1 1 d . . . . .
C24 C 0.0364(8) 0.7894(3) 0.6026(6) 0.033(3) Uani 1 1 d . U . . .
C3 C 1.1194(8) 0.6342(3) 0.4278(7) 0.037(3) Uani 1 1 d . U . . .
C8 C 0.5091(8) 0.8027(3) 0.4347(7) 0.034(3) Uani 1 1 d . U . . .
C27 C 0.0849(8) 0.8953(3) 0.4666(6) 0.034(3) Uani 1 1 d . U . . .
H23 H 0.098788 0.930401 0.421305 0.041 Uiso 1 1 calc R U . . .
C23 C 0.0021(9) 0.7361(3) 0.6693(7) 0.039(3) Uani 1 1 d . U . . .
C1 C 1.1778(9) 0.7396(3) 0.2873(8) 0.036(4) Uani 1 1 d . U . . .
C21 C -0.3856(9) 0.8858(3) 0.6340(7) 0.041(3) Uani 1 1 d . U . . .
C25 C -0.1551(8) 0.8634(3) 0.5830(7) 0.038(3) Uani 1 1 d . U . . .
O3 O -0.5545(7) 0.9504(2) 0.6180(5) 0.074(5) Uani 1 1 d . . . . .
C28 C 0.2825(8) 0.8231(3) 0.4865(6) 0.031(3) Uani 1 1 d . U . . .
C7 C 0.5472(9) 0.8528(3) 0.3686(7) 0.040(4) Uani 1 1 d . U . . .
H2 H 0.425117 0.902158 0.355534 0.049 Uiso 1 1 calc R U . . .
C2 C 1.3447(9) 0.6123(3) 0.3772(7) 0.036(3) Uani 1 1 d . U . . .
C26 C -0.1322(9) 0.9139(3) 0.5153(7) 0.035(3) Uani 1 1 d . U . . .
H22 H -0.264272 0.961327 0.501790 0.042 Uiso 1 1 calc R U . . .
O1 O 1.2026(8) 0.7822(3) 0.2261(7) 0.058(7) Uani 1 1 d . . . . .
C6 C 0.7650(9) 0.8329(3) 0.3190(7) 0.040(4) Uani 1 1 d . U . . .
H1 H 0.782877 0.867177 0.273441 0.048 Uiso 1 1 calc R U . . .
C11 C 0.8830(8) 0.6030(3) 0.5438(6) 0.040(3) Uani 1 1 d . U . . .
H3 H 0.872943 0.567380 0.589001 0.048 Uiso 1 1 calc R U . . .
C31 C 0.4084(10) 0.6427(3) 0.6423(7) 0.037(4) Uani 1 1 d . U . . .
H24 H 0.530839 0.593520 0.656166 0.044 Uiso 1 1 calc R U . . .
C12 C 1.1019(9) 0.5846(3) 0.4944(7) 0.043(4) Uani 1 1 d . U . . .
H4 H 1.236367 0.537584 0.507758 0.052 Uiso 1 1 calc R U . . .
C30 C 0.4506(8) 0.6941(3) 0.5767(6) 0.032(3) Uani 1 1 d . U . . .
C32 C 0.1860(9) 0.6629(3) 0.6886(6) 0.040(3) Uani 1 1 d . U . . .
H25 H 0.160188 0.627044 0.732933 0.048 Uiso 1 1 calc R U . . .
C22 C -0.2287(9) 0.7558(3) 0.7203(8) 0.048(3) Uani 1 1 d . U . . .
C9 C 0.7029(8) 0.7274(3) 0.4572(7) 0.037(3) Uani 1 1 d . U . . .
C10 C 0.6796(8) 0.6743(3) 0.5260(6) 0.030(3) Uani 1 1 d . U . . .
C34 C -0.4914(11) 0.8892(3) 0.8088(7) 0.052(4) Uani 1 1 d . U . . .
H28 H -0.643481 0.896907 0.844116 0.063 Uiso 1 1 calc R U . . .
H29 H -0.330956 0.850136 0.833927 0.063 Uiso 1 1 calc R U . . .
C36 C -0.2400(10) 1.0063(3) 0.8345(7) 0.051(4) Uani 1 1 d . U . . .
H32 H -0.111468 1.046217 0.810343 0.062 Uiso 1 1 calc R U . . .
H33 H -0.115985 0.963430 0.867732 0.062 Uiso 1 1 calc R U . . .
C35 C -0.3699(10) 0.9697(3) 0.7787(7) 0.051(4) Uani 1 1 d . U . . .
H31 H -0.216359 0.961752 0.743803 0.061 Uiso 1 1 calc R U . . .
H30 H -0.529910 1.008458 0.753000 0.061 Uiso 1 1 calc R U . . .
C17 C 1.7333(10) 0.4376(3) 0.0966(7) 0.048(4) Uani 1 1 d . U . . .
H13 H 1.846461 0.474963 0.063165 0.058 Uiso 1 1 calc R U . . .
H14 H 1.873547 0.400621 0.130618 0.058 Uiso 1 1 calc R U . . .
C15 C 1.6603(9) 0.5444(3) 0.1734(7) 0.050(4) Uani 1 1 d . U . . .
H9 H 1.745383 0.584544 0.135974 0.060 Uiso 1 1 calc R U . . .
H10 H 1.822167 0.513679 0.204900 0.060 Uiso 1 1 calc R U . . .
C14 C 1.4369(9) 0.5888(3) 0.2179(7) 0.052(4) Uani 1 1 d . U . . .
H7 H 1.286363 0.623495 0.185274 0.062 Uiso 1 1 calc R U . . .
H8 H 1.336400 0.548376 0.251620 0.062 Uiso 1 1 calc R U . . .
C29 C 0.2589(8) 0.7695(3) 0.5536(6) 0.031(3) Uani 1 1 d . U . . .
C33 C -0.6262(9) 0.8533(3) 0.7515(7) 0.040(3) Uani 1 1 d . U . . .
H27 H -0.716215 0.804858 0.775427 0.048 Uiso 1 1 calc R U . . .
H26 H -0.783376 0.892749 0.725426 0.048 Uiso 1 1 calc R U . . .
C13 C 1.5798(8) 0.6401(3) 0.2596(6) 0.040(3) Uani 1 1 d . U . . .
H6 H 1.754968 0.608739 0.285526 0.048 Uiso 1 1 calc R U . . .
H5 H 1.643151 0.687717 0.226345 0.048 Uiso 1 1 calc R U . . .
C16 C 1.5136(9) 0.4869(3) 0.1386(7) 0.054(4) Uani 1 1 d . U . . .
H11 H 1.358162 0.518316 0.105512 0.065 Uiso 1 1 calc R U . . .
H12 H 1.418747 0.448930 0.176025 0.065 Uiso 1 1 calc R U . . .
C40 C -0.6694(14) 1.2182(3) 0.9127(8) 0.064(6) Uani 1 1 d . U . . .
H40 H -0.775986 1.204117 0.874762 0.096 Uiso 1 1 calc R U . . .
H41 H -0.504752 1.246917 0.892348 0.096 Uiso 1 1 calc R U . . .
H42 H -0.801524 1.252445 0.936120 0.096 Uiso 1 1 calc R U . . .
C37 C -0.4714(9) 1.0478(3) 0.8787(7) 0.051(4) Uani 1 1 d . U . . .
H34 H -0.597085 1.090526 0.845731 0.061 Uiso 1 1 calc R U . . .
H35 H -0.598304 1.007906 0.903756 0.061 Uiso 1 1 calc R U . . .
C19 C 1.7811(12) 0.3364(3) 0.0164(8) 0.057(4) Uani 1 1 d . U . . .
H17 H 1.667161 0.320499 -0.019912 0.068 Uiso 1 1 calc R U . . .
H18 H 1.936260 0.367439 -0.008020 0.068 Uiso 1 1 calc R U . . .
C20 C 1.9211(17) 0.2618(4) 0.0684(9) 0.070(6) Uani 1 1 d . U . . .
H19 H 2.028592 0.225793 0.042084 0.104 Uiso 1 1 calc R U . . .
H20 H 1.768150 0.234331 0.096546 0.104 Uiso 1 1 calc R U . . .
H21 H 2.056567 0.277102 0.100076 0.104 Uiso 1 1 calc R U . . .
C18 C 1.5757(10) 0.3896(3) 0.0555(7) 0.057(4) Uani 1 1 d . U . . .
H15 H 1.442820 0.427207 0.020154 0.069 Uiso 1 1 calc R U . . .
H16 H 1.453258 0.354904 0.088895 0.069 Uiso 1 1 calc R U . . .
C38 C -0.3310(10) 1.0845(3) 0.9333(7) 0.056(4) Uani 1 1 d . U . . .
H36 H -0.174864 1.115789 0.909762 0.067 Uiso 1 1 calc R U . . .
H37 H -0.237562 1.040568 0.971410 0.067 Uiso 1 1 calc R U . . .
C39 C -0.5514(12) 1.1404(3) 0.9680(8) 0.057(4) Uani 1 1 d . U . . .
H38 H -0.717915 1.111099 0.987980 0.068 Uiso 1 1 calc R U . . .
H39 H -0.451918 1.154828 1.007339 0.068 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
N1 C1 1.403(8) . ?
N1 C2 1.372(16) . ?
N1 C13 1.478(11) . ?
C5 C4 1.354(18) . ?
C5 C1 1.497(14) . ?
C5 C6 1.400(8) . ?
C4 C3 1.421(8) . ?
C4 C9 1.438(12) . ?
O4 C22 1.248(17) . ?
N2 C21 1.365(16) . ?
N2 C22 1.398(7) . ?
N2 C33 1.482(11) . ?
O2 C2 1.242(6) . ?
C24 C23 1.391(18) . ?
C24 C25 1.414(7) . ?
C24 C29 1.421(12) . ?
C3 C2 1.464(12) . ?
C3 C12 1.352(18) . ?
C8 C28 1.475(12) . ?
C8 C7 1.362(18) . ?
C8 C9 1.440(8) . ?
C27 H23 0.9300 . ?
C27 C28 1.406(7) . ?
C27 C26 1.395(11) . ?
C23 C32 1.386(7) . ?
C23 C22 1.473(13) . ?
C1 O1 1.228(19) . ?
C21 C25 1.486(12) . ?
C21 O3 1.237(6) . ?
C25 C26 1.377(18) . ?
C28 C29 1.392(17) . ?
C7 H2 0.9300 . ?
C7 C6 1.416(12) . ?
C26 H22 0.9300 . ?
C6 H1 0.9300 . ?
C11 H3 0.9300 . ?
C11 C12 1.409(11) . ?
C11 C10 1.406(6) . ?
C31 H24 0.9300 . ?
C31 C30 1.368(18) . ?
C31 C32 1.388(12) . ?
C12 H4 0.9300 . ?
C30 C10 1.463(12) . ?
C30 C29 1.439(7) . ?
C32 H25 0.9300 . ?
C9 C10 1.412(18) . ?
C34 H28 0.9700 . ?
C34 H29 0.9700 . ?
C34 C35 1.512(9) . ?
C34 C33 1.528(13) . ?
C36 H32 0.9700 . ?
C36 H33 0.9700 . ?
C36 C35 1.502(13) . ?
C36 C37 1.536(11) . ?
C35 H31 0.9700 . ?
C35 H30 0.9700 . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C16 1.552(10) . ?
C17 C18 1.489(10) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C14 1.545(10) . ?
C15 C16 1.510(8) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C13 1.504(9) . ?
C33 H27 0.9700 . ?
C33 H26 0.9700 . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C40 H40 0.9600 . ?
C40 H41 0.9600 . ?
C40 H42 0.9600 . ?
C40 C39 1.528(15) . ?
C37 H34 0.9700 . ?
C37 H35 0.9700 . ?
C37 C38 1.508(11) . ?
C19 H17 0.9700 . ?
C19 H18 0.9700 . ?
C19 C20 1.492(15) . ?
C19 C18 1.522(11) . ?
C20 H19 0.9600 . ?
C20 H20 0.9600 . ?
C20 H21 0.9600 . ?
C18 H15 0.9700 . ?
C18 H16 0.9700 . ?
C38 H36 0.9700 . ?
C38 H37 0.9700 . ?
C38 C39 1.538(10) . ?
C39 H38 0.9700 . ?
C39 H39 0.9700 . ?

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 C13 117.7(10) . . ?
C2 N1 C1 125.5(8) . . ?
C2 N1 C13 116.5(5) . . ?
C4 C5 C1 121.8(5) . . ?
C4 C5 C6 122.1(8) . . ?
C6 C5 C1 116.0(10) . . ?
C5 C4 C3 120.7(8) . . ?
C5 C4 C9 121.1(5) . . ?
C3 C4 C9 118.1(10) . . ?
C21 N2 C22 125.4(8) . . ?
C21 N2 C33 117.7(5) . . ?
C22 N2 C33 116.9(9) . . ?
C23 C24 C25 119.6(8) . . ?
C23 C24 C29 120.7(5) . . ?
C25 C24 C29 119.8(10) . . ?
C4 C3 C2 119.4(10) . . ?
C12 C3 C4 121.0(8) . . ?
C12 C3 C2 119.6(5) . . ?
C7 C8 C28 122.9(5) . . ?
C7 C8 C9 119.6(8) . . ?
C9 C8 C28 117.4(10) . . ?
C28 C27 H23 120.3 . . ?
C26 C27 H23 120.3 . . ?
C26 C27 C28 119.4(9) . . ?
C24 C23 C22 121.2(5) . . ?
C32 C23 C24 120.0(8) . . ?
C32 C23 C22 118.8(10) . . ?
N1 C1 C5 114.7(11) . . ?
O1 C1 N1 120.8(9) . . ?
O1 C1 C5 124.4(6) . . ?
N2 C21 C25 116.8(5) . . ?
O3 C21 N2 121.8(8) . . ?
O3 C21 C25 121.4(10) . . ?
C24 C25 C21 120.5(10) . . ?
C26 C25 C24 119.5(8) . . ?
C26 C25 C21 120.0(6) . . ?
C27 C28 C8 119.5(9) . . ?
C29 C28 C8 119.9(5) . . ?
C29 C28 C27 120.6(7) . . ?
C8 C7 H2 118.6 . . ?
C8 C7 C6 122.8(5) . . ?
C6 C7 H2 118.6 . . ?
N1 C2 C3 117.7(5) . . ?
O2 C2 N1 120.7(8) . . ?
O2 C2 C3 121.6(10) . . ?
C27 C26 H22 119.3 . . ?
C25 C26 C27 121.4(5) . . ?
C25 C26 H22 119.3 . . ?
C5 C6 C7 117.2(10) . . ?
C5 C6 H1 121.4 . . ?
C7 C6 H1 121.4 . . ?
C12 C11 H3 119.5 . . ?
C10 C11 H3 119.5 . . ?
C10 C11 C12 121.1(9) . . ?
C30 C31 H24 119.5 . . ?
C30 C31 C32 121.1(5) . . ?
C32 C31 H24 119.5 . . ?
C3 C12 C11 121.0(5) . . ?
C3 C12 H4 119.5 . . ?
C11 C12 H4 119.5 . . ?
C31 C30 C10 122.6(5) . . ?
C31 C30 C29 120.3(8) . . ?
C29 C30 C10 117.1(9) . . ?
C23 C32 C31 120.4(10) . . ?
C23 C32 H25 119.8 . . ?
C31 C32 H25 119.8 . . ?
O4 C22 N2 119.8(8) . . ?
O4 C22 C23 123.7(6) . . ?
N2 C22 C23 116.5(10) . . ?
C4 C9 C8 117.1(10) . . ?
C10 C9 C4 120.8(5) . . ?
C10 C9 C8 122.1(8) . . ?
C11 C10 C30 121.7(9) . . ?
C11 C10 C9 118.0(7) . . ?
C9 C10 C30 120.3(5) . . ?
H28 C34 H29 107.6 . . ?
C35 C34 H28 108.7 . . ?
C35 C34 H29 108.7 . . ?
C35 C34 C33 114.0(9) . . ?
C33 C34 H28 108.7 . . ?
C33 C34 H29 108.7 . . ?
H32 C36 H33 107.5 . . ?
C35 C36 H32 108.5 . . ?
C35 C36 H33 108.5 . . ?
C35 C36 C37 114.9(4) . . ?
C37 C36 H32 108.5 . . ?
C37 C36 H33 108.5 . . ?
C34 C35 H31 108.6 . . ?
C34 C35 H30 108.6 . . ?
C36 C35 C34 114.6(9) . . ?
C36 C35 H31 108.6 . . ?
C36 C35 H30 108.6 . . ?
H31 C35 H30 107.6 . . ?
H13 C17 H14 107.9 . . ?
C16 C17 H13 109.2 . . ?
C16 C17 H14 109.2 . . ?
C18 C17 H13 109.2 . . ?
C18 C17 H14 109.2 . . ?
C18 C17 C16 112.2(4) . . ?
H9 C15 H10 107.9 . . ?
C14 C15 H9 109.2 . . ?
C14 C15 H10 109.2 . . ?
C16 C15 H9 109.2 . . ?
C16 C15 H10 109.2 . . ?
C16 C15 C14 112.0(4) . . ?
C15 C14 H7 108.8 . . ?
C15 C14 H8 108.8 . . ?
H7 C14 H8 107.7 . . ?
C13 C14 C15 113.8(4) . . ?
C13 C14 H7 108.8 . . ?
C13 C14 H8 108.8 . . ?
C24 C29 C30 117.5(10) . . ?
C28 C29 C24 119.3(5) . . ?
C28 C29 C30 123.2(8) . . ?
N2 C33 C34 112.9(4) . . ?
N2 C33 H27 109.0 . . ?
N2 C33 H26 109.0 . . ?
C34 C33 H27 109.0 . . ?
C34 C33 H26 109.0 . . ?
H27 C33 H26 107.8 . . ?
N1 C13 C14 109.9(4) . . ?
N1 C13 H6 109.7 . . ?
N1 C13 H5 109.7 . . ?
C14 C13 H6 109.7 . . ?
C14 C13 H5 109.7 . . ?
H6 C13 H5 108.2 . . ?
C17 C16 H11 108.8 . . ?
C17 C16 H12 108.8 . . ?
C15 C16 C17 113.8(4) . . ?
C15 C16 H11 108.8 . . ?
C15 C16 H12 108.8 . . ?
H11 C16 H12 107.7 . . ?
H40 C40 H41 109.5 . . ?
H40 C40 H42 109.5 . . ?
H41 C40 H42 109.5 . . ?
C39 C40 H40 109.5 . . ?
C39 C40 H41 109.5 . . ?
C39 C40 H42 109.5 . . ?
C36 C37 H34 109.0 . . ?
C36 C37 H35 109.0 . . ?
H34 C37 H35 107.8 . . ?
C38 C37 C36 113.0(4) . . ?
C38 C37 H34 109.0 . . ?
C38 C37 H35 109.0 . . ?
H17 C19 H18 108.1 . . ?
C20 C19 H17 109.5 . . ?
C20 C19 H18 109.5 . . ?
C20 C19 C18 110.9(11) . . ?
C18 C19 H17 109.5 . . ?
C18 C19 H18 109.5 . . ?
C19 C20 H19 109.5 . . ?
C19 C20 H20 109.5 . . ?
C19 C20 H21 109.5 . . ?
H19 C20 H20 109.5 . . ?
H19 C20 H21 109.5 . . ?
H20 C20 H21 109.5 . . ?
C17 C18 C19 114.6(4) . . ?
C17 C18 H15 108.6 . . ?
C17 C18 H16 108.6 . . ?
C19 C18 H15 108.6 . . ?
C19 C18 H16 108.6 . . ?
H15 C18 H16 107.6 . . ?
C37 C38 H36 108.7 . . ?
C37 C38 H37 108.7 . . ?
C37 C38 C39 114.3(5) . . ?
H36 C38 H37 107.6 . . ?
C39 C38 H36 108.7 . . ?
C39 C38 H37 108.7 . . ?
C40 C39 C38 111.4(10) . . ?
C40 C39 H38 109.3 . . ?
C40 C39 H39 109.3 . . ?
C38 C39 H38 109.3 . . ?
C38 C39 H39 109.3 . . ?
H38 C39 H39 108.0 . . ?

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
C5 C4 C3 C2 -3.2(10) . . . . ?
C5 C4 C3 C12 176.4(6) . . . . ?
C5 C4 C9 C8 2.0(9) . . . . ?
C5 C4 C9 C10 -178.1(6) . . . . ?
C4 C5 C1 N1 -3.4(10) . . . . ?
C4 C5 C1 O1 175.9(8) . . . . ?
C4 C5 C6 C7 2.0(9) . . . . ?
C4 C3 C2 N1 2.7(8) . . . . ?
C4 C3 C2 O2 -176.7(5) . . . . ?
C4 C3 C12 C11 1.9(10) . . . . ?
C4 C9 C10 C11 1.6(9) . . . . ?
C4 C9 C10 C30 -178.8(4) . . . . ?
N2 C21 C25 C24 -0.7(9) . . . . ?
N2 C21 C25 C26 177.6(6) . . . . ?
C24 C23 C32 C31 1.1(9) . . . . ?
C24 C23 C22 O4 179.6(7) . . . . ?
C24 C23 C22 N2 -2.0(10) . . . . ?
C24 C25 C26 C27 -2.8(10) . . . . ?
C3 C4 C9 C8 179.2(5) . . . . ?
C3 C4 C9 C10 -0.9(9) . . . . ?
C8 C28 C29 C24 -179.0(4) . . . . ?
C8 C28 C29 C30 1.2(10) . . . . ?
C8 C7 C6 C5 -2.2(10) . . . . ?
C8 C9 C10 C11 -178.6(4) . . . . ?
C8 C9 C10 C30 1.0(10) . . . . ?
C27 C28 C29 C24 -1.3(9) . . . . ?
C27 C28 C29 C30 178.9(4) . . . . ?
C23 C24 C25 C21 1.9(10) . . . . ?
C23 C24 C25 C26 -176.3(6) . . . . ?
C23 C24 C29 C28 178.3(6) . . . . ?
C23 C24 C29 C30 -1.8(9) . . . . ?
C1 N1 C2 O2 176.6(5) . . . . ?
C1 N1 C2 C3 -2.8(10) . . . . ?
C1 N1 C13 C14 -89.1(6) . . . . ?
C1 C5 C4 C3 3.7(11) . . . . ?
C1 C5 C4 C9 -179.2(5) . . . . ?
C1 C5 C6 C7 179.3(5) . . . . ?
C21 N2 C22 O4 -178.1(7) . . . . ?
C21 N2 C22 C23 3.5(10) . . . . ?
C21 N2 C33 C34 -98.2(9) . . . . ?
C21 C25 C26 C27 178.9(4) . . . . ?
C25 C24 C23 C32 179.2(5) . . . . ?
C25 C24 C23 C22 -0.6(10) . . . . ?
C25 C24 C29 C28 -0.7(9) . . . . ?
C25 C24 C29 C30 179.1(5) . . . . ?
O3 C21 C25 C24 179.8(5) . . . . ?
O3 C21 C25 C26 -2.0(9) . . . . ?
C28 C8 C7 C6 -179.9(4) . . . . ?
C28 C8 C9 C4 180.0(4) . . . . ?
C28 C8 C9 C10 0.1(9) . . . . ?
C28 C27 C26 C25 0.8(9) . . . . ?
C7 C8 C28 C27 3.2(9) . . . . ?
C7 C8 C28 C29 -179.0(6) . . . . ?
C7 C8 C9 C4 -2.1(10) . . . . ?
C7 C8 C9 C10 178.0(6) . . . . ?
C2 N1 C1 C5 3.0(10) . . . . ?
C2 N1 C1 O1 -176.3(7) . . . . ?
C2 N1 C13 C14 84.7(8) . . . . ?
C2 C3 C12 C11 -178.5(4) . . . . ?
C26 C27 C28 C8 179.0(4) . . . . ?
C26 C27 C28 C29 1.3(8) . . . . ?
C6 C5 C4 C3 -179.2(5) . . . . ?
C6 C5 C4 C9 -2.0(11) . . . . ?
C6 C5 C1 N1 179.3(5) . . . . ?
C6 C5 C1 O1 -1.4(11) . . . . ?
C31 C30 C10 C11 -3.9(9) . . . . ?
C31 C30 C10 C9 176.5(6) . . . . ?
C31 C30 C29 C24 2.6(9) . . . . ?
C31 C30 C29 C28 -177.6(6) . . . . ?
C12 C3 C2 N1 -176.9(6) . . . . ?
C12 C3 C2 O2 3.7(9) . . . . ?
C12 C11 C10 C30 179.8(5) . . . . ?
C12 C11 C10 C9 -0.6(8) . . . . ?
C30 C31 C32 C23 -0.3(10) . . . . ?
C32 C23 C22 O4 -0.1(11) . . . . ?
C32 C23 C22 N2 178.3(5) . . . . ?
C32 C31 C30 C10 -179.0(4) . . . . ?
C32 C31 C30 C29 -1.5(11) . . . . ?
C22 N2 C21 C25 -2.2(10) . . . . ?
C22 N2 C21 O3 177.4(5) . . . . ?
C22 N2 C33 C34 82.6(6) . . . . ?
C22 C23 C32 C31 -179.2(5) . . . . ?
C9 C4 C3 C2 179.5(4) . . . . ?
C9 C4 C3 C12 -0.8(9) . . . . ?
C9 C8 C28 C27 -179.0(4) . . . . ?
C9 C8 C28 C29 -1.2(9) . . . . ?
C9 C8 C7 C6 2.3(11) . . . . ?
C10 C11 C12 C3 -1.2(9) . . . . ?
C10 C30 C29 C24 -179.8(4) . . . . ?
C10 C30 C29 C28 0.0(9) . . . . ?
C36 C37 C38 C39 168.9(9) . . . . ?
C35 C34 C33 N2 64.3(7) . . . . ?
C35 C36 C37 C38 -179.3(7) . . . . ?
C15 C14 C13 N1 -168.5(8) . . . . ?
C14 C15 C16 C17 -177.0(8) . . . . ?
C29 C24 C23 C32 0.1(10) . . . . ?
C29 C24 C23 C22 -179.7(5) . . . . ?
C29 C24 C25 C21 -179.0(5) . . . . ?
C29 C24 C25 C26 2.8(9) . . . . ?
C29 C30 C10 C11 178.5(4) . . . . ?
C29 C30 C10 C9 -1.1(9) . . . . ?
C33 N2 C21 C25 178.6(4) . . . . ?
C33 N2 C21 O3 -1.8(9) . . . . ?
C33 N2 C22 O4 1.1(10) . . . . ?
C33 N2 C22 C23 -177.3(5) . . . . ?
C33 C34 C35 C36 179.3(4) . . . . ?
C13 N1 C1 C5 176.3(4) . . . . ?
C13 N1 C1 O1 -3.1(10) . . . . ?
C13 N1 C2 O2 3.3(9) . . . . ?
C13 N1 C2 C3 -176.1(4) . . . . ?
C16 C17 C18 C19 -176.9(9) . . . . ?
C16 C15 C14 C13 174.1(8) . . . . ?
C37 C36 C35 C34 -77.1(8) . . . . ?
C37 C38 C39 C40 -67.6(7) . . . . ?
C20 C19 C18 C17 76.2(8) . . . . ?
C18 C17 C16 C15 -172.8(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_PDI_C8_0_40GPa
_database_code_depnum_ccdc_archive 'CCDC 2493918'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C8_0_40GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.302 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT088_PDI_C8_0_40GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.88 Note
RESPONSE: The data/parameter ratio is affected by the access limits of 
the DAC, particularly disadvantageous for low-symmetry crystals.
;
_vrf_PLAT910_PDI_C8_0_40GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         92 Note   
RESPONSE: The unit cell is reasonable large and these low angle 
reflections are probably missing due to the beamstop.
;
_vrf_PLAT911_PDI_C8_0_40GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        827 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-08-07

_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            PDI-C8
_chemical_name_systematic        N,N-Dioctyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C40 H42 N2 O4'
_chemical_formula_sum            'C40 H42 N2 O4'
_chemical_formula_weight         614.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N1O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0004 0.0007 '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 -0.0003 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0008 0.0027 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.62072(16)
_cell_length_b                   8.6608(3)
_cell_length_c                   19.439(4)
_cell_angle_alpha                84.805(7)
_cell_angle_beta                 87.168(7)
_cell_angle_gamma                82.076(3)
_cell_volume                     766.82(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    813
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.7520
_cell_measurement_theta_min      5.5360
_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  0.82499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.065
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.012
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.302
_diffrn_reflns_Laue_measured_fraction_max 0.196
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3297
_diffrn_reflns_point_group_measured_fraction_full 0.302
_diffrn_reflns_point_group_measured_fraction_max 0.196
_diffrn_reflns_theta_full        17.166
_diffrn_reflns_theta_max         22.749
_diffrn_reflns_theta_min         5.451
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.302
_diffrn_measured_fraction_theta_max 0.196
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     21.00  97.00   0.25    0.25  57.05   0.00-134.76    --   304
  2  φ     21.00  97.00   0.25    0.25  57.05   0.00-134.76    --   304
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0002648000
_diffrn_orient_matrix_UB_12      -0.0038793000
_diffrn_orient_matrix_UB_13      0.0253996000
_diffrn_orient_matrix_UB_21      -0.0592472000
_diffrn_orient_matrix_UB_22      -0.0432430000
_diffrn_orient_matrix_UB_23      0.0010452000
_diffrn_orient_matrix_UB_31      0.0897672000
_diffrn_orient_matrix_UB_32      -0.0377756000
_diffrn_orient_matrix_UB_33      -0.0005256000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.4919
_diffrn_source                   synchrotron
_diffrn_special_details          
;
Data were collected at room temperature and pressure of 0.40(2) GPa.
Pressure was determined by monitoring the shift of the ruby R1-fluorescence line.'
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                829
_reflns_number_total             1229
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0748
_refine_ls_restrained_S_all      1.065
_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)+(0.1680P)²+0.0135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2013
_refine_ls_wR_factor_ref         0.2290
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C16(H11,H12), C15(H9,H10), C17(H13,H14), C13(H5,H6), C14(H7,H8), C18(H15,H16),
  C19(H17,H18)
1.b Aromatic/amide H refined with riding coordinates:
 C11(H3), C7(H2), C12(H4), C6(H1)
1.c Idealised Me refined as rotating group:
 C20(H21,H19,H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.8441(5) 0.6910(3) 0.6863(4) 0.098(4) Uani 1 1 d . . . . .
O2 O 1.0022(5) 0.5165(2) 0.6071(3) 0.108(4) Uani 1 1 d . . . . .
C10 C 0.2027(5) 0.8670(3) 0.4804(4) 0.081(4) Uani 1 1 d . . . . .
C8 C 0.0153(5) 1.0547(3) 0.5684(5) 0.075(4) Uani 1 1 d . . . . .
O1 O 0.6722(6) 0.8600(4) 0.7657(6) 0.123(6) Uani 1 1 d . . . . .
C4 C 0.4226(5) 0.8460(3) 0.5940(4) 0.071(4) Uani 1 1 d . . . . .
C1 C 0.6547(7) 0.8201(4) 0.7071(6) 0.075(6) Uani 1 1 d . . . . .
C3 C 0.6227(5) 0.7153(3) 0.5727(5) 0.076(5) Uani 1 1 d . . . . .
C9 C 0.2135(5) 0.9218(3) 0.5465(4) 0.076(4) Uani 1 1 d . . . . .
C11 C 0.4044(6) 0.7394(3) 0.4620(4) 0.091(5) Uani 1 1 d . . . . .
H3 H 0.4005 0.7034 0.4185 0.110 Uiso 1 1 calc R U . . .
C2 C 0.8351(6) 0.6339(3) 0.6221(5) 0.084(5) Uani 1 1 d . . . . .
C5 C 0.4391(6) 0.8992(3) 0.6588(5) 0.086(5) Uani 1 1 d . . . . .
C7 C 0.0423(6) 1.1036(4) 0.6324(5) 0.083(5) Uani 1 1 d . . . . .
H2 H -0.0813 1.1910 0.6454 0.100 Uiso 1 1 calc R U . . .
C12 C 0.6118(6) 0.6660(3) 0.5090(5) 0.088(5) Uani 1 1 d . . . . .
H4 H 0.7443 0.5819 0.4960 0.106 Uiso 1 1 calc R U . . .
C6 C 0.2480(6) 1.0279(3) 0.6794(5) 0.086(5) Uani 1 1 d . . . . .
H1 H 0.2568 1.0624 0.7230 0.103 Uiso 1 1 calc R U . . .
C16 C 0.9877(7) 0.2102(4) 0.8477(5) 0.102(6) Uani 1 1 d . . . . .
H11 H 0.8420 0.2471 0.8823 0.122 Uiso 1 1 calc R U . . .
H12 H 0.8883 0.1655 0.8131 0.122 Uiso 1 1 calc R U . . .
C15 C 1.1274(6) 0.3500(4) 0.8133(5) 0.103(5) Uani 1 1 d . . . . .
H9 H 1.2136 0.4001 0.8484 0.123 Uiso 1 1 calc R U . . .
H10 H 1.2830 0.3125 0.7811 0.123 Uiso 1 1 calc R U . . .
C17 C 1.2066(7) 0.0840(4) 0.8817(5) 0.085(5) Uani 1 1 d . . . . .
H13 H 1.2852 0.1241 0.9208 0.101 Uiso 1 1 calc R U . . .
H14 H 1.3673 0.0575 0.8490 0.101 Uiso 1 1 calc R U . . .
C13 C 1.0465(6) 0.6024(4) 0.7355(5) 0.082(5) Uani 1 1 d . . . . .
H5 H 1.0998 0.6717 0.7678 0.099 Uiso 1 1 calc R U . . .
H6 H 1.2233 0.5603 0.7108 0.099 Uiso 1 1 calc R U . . .
C14 C 0.9092(6) 0.4687(4) 0.7751(5) 0.110(5) Uani 1 1 d . . . . .
H7 H 0.7624 0.5119 0.8081 0.132 Uiso 1 1 calc R U . . .
H8 H 0.8112 0.4162 0.7429 0.132 Uiso 1 1 calc R U . . .
C18 C 1.0722(7) -0.0638(4) 0.9066(5) 0.105(6) Uani 1 1 d . . . . .
H15 H 0.9177 -0.0377 0.9409 0.126 Uiso 1 1 calc R U . . .
H16 H 0.9840 -0.1001 0.8678 0.126 Uiso 1 1 calc R U . . .
C19 C 1.2890(8) -0.1956(4) 0.9376(6) 0.110(7) Uani 1 1 d . . . . .
H17 H 1.3740 -0.1610 0.9772 0.132 Uiso 1 1 calc R U . . .
H18 H 1.4457 -0.2212 0.9038 0.132 Uiso 1 1 calc R U . . .
C20 C 1.1485(14) -0.3414(5) 0.9602(7) 0.154(9) Uani 1 1 d . . . . .
H21 H 1.1262 -0.3968 0.9206 0.231 Uiso 1 1 calc R U . . .
H19 H 0.9601 -0.3119 0.9818 0.231 Uiso 1 1 calc R U . . .
H20 H 1.2704 -0.4077 0.9925 0.231 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
N1 C1 1.399(6) . ?
N1 C2 1.389(11) . ?
N1 C13 1.461(8) . ?
O2 C2 1.236(5) . ?
C10 C8 1.472(9) 2_576 ?
C10 C9 1.414(12) . ?
C10 C11 1.404(5) . ?
C8 C10 1.472(9) 2_576 ?
C8 C9 1.451(5) . ?
C8 C7 1.366(13) . ?
O1 C1 1.229(14) . ?
C4 C3 1.438(6) . ?
C4 C9 1.422(9) . ?
C4 C5 1.388(13) . ?
C1 C5 1.460(10) . ?
C3 C2 1.469(9) . ?
C3 C12 1.353(13) . ?
C11 H3 0.9300 . ?
C11 C12 1.403(9) . ?
C5 C6 1.399(6) . ?
C7 H2 0.9300 . ?
C7 C6 1.405(9) . ?
C12 H4 0.9300 . ?
C6 H1 0.9300 . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C15 1.535(7) . ?
C16 C17 1.512(7) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C14 1.508(7) . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C18 1.528(6) . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C13 C14 1.527(7) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C18 H15 0.9700 . ?
C18 H16 0.9700 . ?
C18 C19 1.514(7) . ?
C19 H17 0.9700 . ?
C19 H18 0.9700 . ?
C19 C20 1.518(6) . ?
C20 H21 0.9600 . ?
C20 H19 0.9600 . ?
C20 H20 0.9600 . ?

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 C13 119.6(7) . . ?
C2 N1 C1 123.0(6) . . ?
C2 N1 C13 117.2(3) . . ?
C9 C10 C8 119.9(4) . 2_576 ?
C11 C10 C8 120.9(7) . 2_576 ?
C11 C10 C9 119.2(5) . . ?
C9 C8 C10 118.0(8) . 2_576 ?
C7 C8 C10 123.0(4) . 2_576 ?
C7 C8 C9 119.0(6) . . ?
C9 C4 C3 118.4(7) . . ?
C5 C4 C3 120.6(6) . . ?
C5 C4 C9 121.0(4) . . ?
N1 C1 C5 118.5(9) . . ?
O1 C1 N1 118.7(7) . . ?
O1 C1 C5 122.8(5) . . ?
C4 C3 C2 118.8(8) . . ?
C12 C3 C4 120.6(6) . . ?
C12 C3 C2 120.6(4) . . ?
C10 C9 C8 122.1(6) . . ?
C10 C9 C4 120.1(4) . . ?
C4 C9 C8 117.8(7) . . ?
C10 C11 H3 119.8 . . ?
C12 C11 C10 120.4(7) . . ?
C12 C11 H3 119.8 . . ?
N1 C2 C3 118.6(4) . . ?
O2 C2 N1 120.4(6) . . ?
O2 C2 C3 121.0(8) . . ?
C4 C5 C1 120.4(4) . . ?
C4 C5 C6 120.9(6) . . ?
C6 C5 C1 118.8(8) . . ?
C8 C7 H2 118.5 . . ?
C8 C7 C6 123.0(4) . . ?
C6 C7 H2 118.5 . . ?
C3 C12 C11 121.3(4) . . ?
C3 C12 H4 119.4 . . ?
C11 C12 H4 119.4 . . ?
C5 C6 C7 118.3(8) . . ?
C5 C6 H1 120.9 . . ?
C7 C6 H1 120.9 . . ?
H11 C16 H12 107.7 . . ?
C15 C16 H11 108.9 . . ?
C15 C16 H12 108.9 . . ?
C17 C16 H11 108.9 . . ?
C17 C16 H12 108.9 . . ?
C17 C16 C15 113.2(3) . . ?
C16 C15 H9 109.1 . . ?
C16 C15 H10 109.1 . . ?
H9 C15 H10 107.9 . . ?
C14 C15 C16 112.3(3) . . ?
C14 C15 H9 109.1 . . ?
C14 C15 H10 109.1 . . ?
C16 C17 H13 109.1 . . ?
C16 C17 H14 109.1 . . ?
C16 C17 C18 112.5(3) . . ?
H13 C17 H14 107.8 . . ?
C18 C17 H13 109.1 . . ?
C18 C17 H14 109.1 . . ?
N1 C13 H5 109.4 . . ?
N1 C13 H6 109.4 . . ?
N1 C13 C14 111.0(3) . . ?
H5 C13 H6 108.0 . . ?
C14 C13 H5 109.4 . . ?
C14 C13 H6 109.4 . . ?
C15 C14 C13 113.5(3) . . ?
C15 C14 H7 108.9 . . ?
C15 C14 H8 108.9 . . ?
C13 C14 H7 108.9 . . ?
C13 C14 H8 108.9 . . ?
H7 C14 H8 107.7 . . ?
C17 C18 H15 108.8 . . ?
C17 C18 H16 108.8 . . ?
H15 C18 H16 107.7 . . ?
C19 C18 C17 113.9(3) . . ?
C19 C18 H15 108.8 . . ?
C19 C18 H16 108.8 . . ?
C18 C19 H17 109.1 . . ?
C18 C19 H18 109.1 . . ?
C18 C19 C20 112.3(4) . . ?
H17 C19 H18 107.9 . . ?
C20 C19 H17 109.1 . . ?
C20 C19 H18 109.1 . . ?
C19 C20 H21 109.5 . . ?
C19 C20 H19 109.5 . . ?
C19 C20 H20 109.5 . . ?
H21 C20 H19 109.5 . . ?
H21 C20 H20 109.5 . . ?
H19 C20 H20 109.5 . . ?

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
N1 C1 C5 C4 0.4(7) . . . . ?
N1 C1 C5 C6 179.6(4) . . . . ?
N1 C13 C14 C15 165.8(6) . . . . ?
C10 C8 C9 C10 0.2(7) 2_576 . . . ?
C10 C8 C9 C4 -179.7(3) 2_576 . . . ?
C10 C8 C7 C6 179.2(3) 2_576 . . . ?
C10 C11 C12 C3 0.2(6) . . . . ?
C8 C10 C9 C8 -0.2(7) 2_576 . . . ?
C8 C10 C9 C4 179.7(3) 2_576 . . . ?
C8 C10 C11 C12 179.8(3) 2_576 . . . ?
C8 C7 C6 C5 1.9(7) . . . . ?
O1 C1 C5 C4 -177.8(6) . . . . ?
O1 C1 C5 C6 1.4(9) . . . . ?
C4 C3 C2 N1 -3.0(6) . . . . ?
C4 C3 C2 O2 176.7(3) . . . . ?
C4 C3 C12 C11 -0.6(7) . . . . ?
C4 C5 C6 C7 -1.1(7) . . . . ?
C1 N1 C2 O2 -177.9(3) . . . . ?
C1 N1 C2 C3 1.8(7) . . . . ?
C1 N1 C13 C14 90.6(5) . . . . ?
C1 C5 C6 C7 179.7(4) . . . . ?
C3 C4 C9 C10 0.9(6) . . . . ?
C3 C4 C9 C8 -179.3(3) . . . . ?
C3 C4 C5 C1 -1.8(7) . . . . ?
C3 C4 C5 C6 179.0(3) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C9 C8 C7 C6 -2.1(8) . . . . ?
C9 C4 C3 C2 -178.6(3) . . . . ?
C9 C4 C3 C12 0.1(6) . . . . ?
C9 C4 C5 C1 179.9(3) . . . . ?
C9 C4 C5 C6 0.7(7) . . . . ?
C11 C10 C9 C8 178.9(3) . . . . ?
C11 C10 C9 C4 -1.3(6) . . . . ?
C2 N1 C1 O1 177.9(5) . . . . ?
C2 N1 C1 C5 -0.4(7) . . . . ?
C2 N1 C13 C14 -84.5(6) . . . . ?
C2 C3 C12 C11 178.0(3) . . . . ?
C5 C4 C3 C2 3.1(6) . . . . ?
C5 C4 C3 C12 -178.2(4) . . . . ?
C5 C4 C9 C10 179.2(4) . . . . ?
C5 C4 C9 C8 -1.0(7) . . . . ?
C7 C8 C9 C10 -178.5(4) . . . . ?
C7 C8 C9 C4 1.6(7) . . . . ?
C12 C3 C2 N1 178.3(4) . . . . ?
C12 C3 C2 O2 -2.0(6) . . . . ?
C16 C15 C14 C13 -175.3(6) . . . . ?
C16 C17 C18 C19 177.0(7) . . . . ?
C15 C16 C17 C18 -171.7(7) . . . . ?
C17 C16 C15 C14 175.7(6) . . . . ?
C17 C18 C19 C20 -178.8(8) . . . . ?
C13 N1 C1 O1 3.0(8) . . . . ?
C13 N1 C1 C5 -175.3(4) . . . . ?
C13 N1 C2 O2 -3.0(6) . . . . ?
C13 N1 C2 C3 176.7(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.376
_oxdiff_exptl_absorpt_empirical_full_min 0.822
####################################################################### 
# 
# 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_PDI_C7_150K
_database_code_depnum_ccdc_archive 'CCDC 2493914'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
_audit_creation_date             2025-03-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        'N,N Diheptyl 3,4,9,10 perylenedicarboximide'
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.79800(10)
_cell_length_b                   8.2755(2)
_cell_length_c                   18.9953(6)
_cell_angle_alpha                79.460(2)
_cell_angle_beta                 89.925(2)
_cell_angle_gamma                82.325(2)
_cell_volume                     734.65(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5643
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      62.566
_cell_measurement_theta_min      2.366
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.799
_exptl_absorpt_coefficient_mu    0.681
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.6504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1261 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.8647.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.034
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21646
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        62.709
_diffrn_reflns_theta_max         62.709
_diffrn_reflns_theta_min         4.737
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 Data were collected at low temperature of 150 K.
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1996
_reflns_number_total             2352
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.206
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.053
_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)+(0.0649P)²+0.2735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1252
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C19A-C18A \\sim C19B-C18A
 with sigma of 0.02
2. Rigid body (RIGU) restrains
 C19A, C19B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(H15B)=Sof(H16B)=Sof(C19B)=Sof(H18B)=Sof(H19B)=Sof(H17B)=1-FVAR(1)
 Sof(H16A)=Sof(H15A)=Sof(C19A)=Sof(H17A)=Sof(H18A)=Sof(H19A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C14(H7,H8), C15(H9,H10), C13(H5,H6), C16(H11,H12), C17(H13,H14), C18A(H16A,
 H15A), C18A(H15B,H16B)
4.b Me refined with riding coordinates:
 C19A(H17A,H18A,H19A), C19B(H18B,H19B,H17B)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H2), C6(H1), C11(H3), C12(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0018(2) 0.59013(13) 0.38737(6) 0.0300(3) Uani 1 1 d . . . . .
O2 O 0.6575(2) 1.04280(15) 0.22256(6) 0.0370(3) Uani 1 1 d . . . . .
N1 N 0.8329(3) 0.81752(16) 0.30530(7) 0.0242(3) Uani 1 1 d . . . . .
C8 C 0.2069(3) 0.85470(18) 0.52066(8) 0.0202(4) Uani 1 1 d . . . . .
C5 C 0.6201(3) 0.76739(18) 0.42339(8) 0.0215(4) Uani 1 1 d . . . . .
C9 C 0.2092(3) 0.95425(18) 0.45120(8) 0.0200(4) Uani 1 1 d . . . . .
C4 C 0.4190(3) 0.90993(18) 0.40221(8) 0.0203(4) Uani 1 1 d . . . . .
C10 C 0.0098(3) 1.09960(18) 0.42890(8) 0.0207(4) Uani 1 1 d . . . . .
C7 C 0.4118(3) 0.71820(18) 0.53932(8) 0.0219(3) Uani 1 1 d . . . . .
H2 H 0.412603 0.652181 0.585850 0.026 Uiso 1 1 calc R U . . .
C6 C 0.6174(3) 0.67567(18) 0.49110(8) 0.0221(4) Uani 1 1 d . . . . .
H1 H 0.756379 0.582266 0.505464 0.027 Uiso 1 1 calc R U . . .
C3 C 0.4282(3) 1.00804(19) 0.33379(8) 0.0227(4) Uani 1 1 d . . . . .
C1 C 0.8328(3) 0.71692(19) 0.37223(8) 0.0233(4) Uani 1 1 d . . . . .
C11 C 0.0295(3) 1.19292(19) 0.36125(8) 0.0246(4) Uani 1 1 d . . . . .
H3 H -0.101209 1.290231 0.346632 0.029 Uiso 1 1 calc R U . . .
C12 C 0.2356(3) 1.14838(19) 0.31382(8) 0.0254(4) Uani 1 1 d . . . . .
H4 H 0.243111 1.214939 0.267651 0.031 Uiso 1 1 calc R U . . .
C14 C 0.9144(3) 0.6461(2) 0.21121(9) 0.0296(4) Uani 1 1 d . . . . .
H7 H 0.841853 0.556969 0.245430 0.035 Uiso 1 1 calc R U . . .
H8 H 0.754096 0.708599 0.180706 0.035 Uiso 1 1 calc R U . . .
C15 C 1.1298(3) 0.5680(2) 0.16425(9) 0.0324(4) Uani 1 1 d . . . . .
H9 H 1.296052 0.512475 0.194258 0.039 Uiso 1 1 calc R U . . .
H10 H 1.192259 0.656813 0.127847 0.039 Uiso 1 1 calc R U . . .
C2 C 0.6433(3) 0.9622(2) 0.28219(8) 0.0250(4) Uani 1 1 d . . . . .
C13 C 1.0345(3) 0.7624(2) 0.25281(8) 0.0270(4) Uani 1 1 d . . . . .
H5 H 1.210268 0.704949 0.278218 0.032 Uiso 1 1 calc R U . . .
H6 H 1.081466 0.860511 0.218964 0.032 Uiso 1 1 calc R U . . .
C16 C 1.0170(3) 0.4419(2) 0.12629(9) 0.0335(4) Uani 1 1 d . . . . .
H11 H 0.946231 0.355951 0.162538 0.040 Uiso 1 1 calc R U . . .
H12 H 0.856400 0.498631 0.094482 0.040 Uiso 1 1 calc R U . . .
C17 C 1.2372(4) 0.3582(3) 0.08207(12) 0.0480(5) Uani 1 1 d . . . . .
H13 H 1.401330 0.306078 0.113552 0.058 Uiso 1 1 calc R U . . .
H14 H 1.301806 0.443932 0.044591 0.058 Uiso 1 1 calc R U . . .
C18A C 1.1320(5) 0.2261(3) 0.04623(15) 0.0636(7) Uani 1 1 d D . . . .
H16A H 0.938831 0.268250 0.027188 0.076 Uiso 0.506(5) 1 calc R U P A 1
H15A H 1.252350 0.211164 0.004909 0.076 Uiso 0.506(5) 1 calc R U P A 1
H15B H 1.023392 0.158582 0.081827 0.076 Uiso 0.494(5) 1 calc R U P A 2
H16B H 0.999190 0.283630 0.006937 0.076 Uiso 0.494(5) 1 calc R U P A 2
C19A C 1.1283(8) 0.0795(5) 0.08746(19) 0.0383(11) Uani 0.506(5) 1 d D . P A 1
H17A H 1.057933 0.004247 0.059563 0.057 Uiso 0.506(5) 1 calc R U P A 1
H18A H 1.319295 0.034164 0.105528 0.057 Uiso 0.506(5) 1 calc R U P A 1
H19A H 1.004895 0.091410 0.127869 0.057 Uiso 0.506(5) 1 calc R U P A 1
C19B C 1.3340(9) 0.1161(7) 0.0176(3) 0.0683(17) Uani 0.494(5) 1 d D . P A 2
H18B H 1.238208 0.038458 -0.003651 0.102 Uiso 0.494(5) 1 calc R U P A 2
H19B H 1.439523 0.179682 -0.019358 0.102 Uiso 0.494(5) 1 calc R U P A 2
H17B H 1.463837 0.054062 0.055874 0.102 Uiso 0.494(5) 1 calc R U P A 2


_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 1.2265(19) . ?
O2 C2 1.2116(19) . ?
N1 C1 1.386(2) . ?
N1 C2 1.404(2) . ?
N1 C13 1.4780(19) . ?
C8 C9 1.423(2) . ?
C8 C10 1.472(2) 2_576 ?
C8 C7 1.388(2) . ?
C5 C4 1.417(2) . ?
C5 C6 1.370(2) . ?
C5 C1 1.481(2) . ?
C9 C4 1.428(2) . ?
C9 C10 1.431(2) . ?
C4 C3 1.405(2) . ?
C10 C11 1.383(2) . ?
C7 H2 0.9500 . ?
C7 C6 1.399(2) . ?
C6 H1 0.9500 . ?
C3 C12 1.378(2) . ?
C3 C2 1.483(2) . ?
C11 H3 0.9500 . ?
C11 C12 1.395(2) . ?
C12 H4 0.9500 . ?
C14 H7 0.9900 . ?
C14 H8 0.9900 . ?
C14 C15 1.520(2) . ?
C14 C13 1.521(2) . ?
C15 H9 0.9900 . ?
C15 H10 0.9900 . ?
C15 C16 1.526(2) . ?
C13 H5 0.9900 . ?
C13 H6 0.9900 . ?
C16 H11 0.9900 . ?
C16 H12 0.9900 . ?
C16 C17 1.522(2) . ?
C17 H13 0.9900 . ?
C17 H14 0.9900 . ?
C17 C18A 1.527(3) . ?
C18A H16A 0.9900 . ?
C18A H15A 0.9900 . ?
C18A H15B 0.9900 . ?
C18A H16B 0.9900 . ?
C18A C19A 1.320(4) . ?
C18A C19B 1.417(4) . ?
C19A H17A 0.9800 . ?
C19A H18A 0.9800 . ?
C19A H19A 0.9800 . ?
C19B H18B 0.9800 . ?
C19B H19B 0.9800 . ?
C19B H17B 0.9800 . ?

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 C2 124.76(13) . . ?
C1 N1 C13 117.58(13) . . ?
C2 N1 C13 117.53(13) . . ?
C9 C8 C10 119.23(14) . 2_576 ?
C7 C8 C9 118.97(14) . . ?
C7 C8 C10 121.79(14) . 2_576 ?
C4 C5 C1 120.03(14) . . ?
C6 C5 C4 120.09(14) . . ?
C6 C5 C1 119.88(14) . . ?
C8 C9 C4 119.28(14) . . ?
C8 C9 C10 122.14(14) . . ?
C4 C9 C10 118.57(14) . . ?
C5 C4 C9 119.52(14) . . ?
C3 C4 C5 120.23(14) . . ?
C3 C4 C9 120.24(14) . . ?
C9 C10 C8 118.62(14) . 2_576 ?
C11 C10 C8 122.41(14) . 2_576 ?
C11 C10 C9 118.97(14) . . ?
C8 C7 H2 119.3 . . ?
C8 C7 C6 121.45(14) . . ?
C6 C7 H2 119.3 . . ?
C5 C6 C7 120.65(14) . . ?
C5 C6 H1 119.7 . . ?
C7 C6 H1 119.7 . . ?
C4 C3 C2 120.71(14) . . ?
C12 C3 C4 120.10(14) . . ?
C12 C3 C2 119.19(14) . . ?
O1 C1 N1 120.47(14) . . ?
O1 C1 C5 121.99(14) . . ?
N1 C1 C5 117.53(13) . . ?
C10 C11 H3 119.0 . . ?
C10 C11 C12 121.95(15) . . ?
C12 C11 H3 119.0 . . ?
C3 C12 C11 120.17(14) . . ?
C3 C12 H4 119.9 . . ?
C11 C12 H4 119.9 . . ?
H7 C14 H8 107.8 . . ?
C15 C14 H7 109.0 . . ?
C15 C14 H8 109.0 . . ?
C15 C14 C13 112.86(12) . . ?
C13 C14 H7 109.0 . . ?
C13 C14 H8 109.0 . . ?
C14 C15 H9 108.9 . . ?
C14 C15 H10 108.9 . . ?
C14 C15 C16 113.25(13) . . ?
H9 C15 H10 107.7 . . ?
C16 C15 H9 108.9 . . ?
C16 C15 H10 108.9 . . ?
O2 C2 N1 120.51(14) . . ?
O2 C2 C3 122.81(15) . . ?
N1 C2 C3 116.68(13) . . ?
N1 C13 C14 111.43(12) . . ?
N1 C13 H5 109.3 . . ?
N1 C13 H6 109.3 . . ?
C14 C13 H5 109.3 . . ?
C14 C13 H6 109.3 . . ?
H5 C13 H6 108.0 . . ?
C15 C16 H11 109.0 . . ?
C15 C16 H12 109.0 . . ?
H11 C16 H12 107.8 . . ?
C17 C16 C15 113.11(14) . . ?
C17 C16 H11 109.0 . . ?
C17 C16 H12 109.0 . . ?
C16 C17 H13 108.8 . . ?
C16 C17 H14 108.8 . . ?
C16 C17 C18A 113.92(16) . . ?
H13 C17 H14 107.7 . . ?
C18A C17 H13 108.8 . . ?
C18A C17 H14 108.8 . . ?
C17 C18A H16A 108.3 . . ?
C17 C18A H15A 108.3 . . ?
C17 C18A H15B 107.8 . . ?
C17 C18A H16B 107.8 . . ?
H16A C18A H15A 107.4 . . ?
H15B C18A H16B 107.1 . . ?
C19A C18A C17 115.9(3) . . ?
C19A C18A H16A 108.3 . . ?
C19A C18A H15A 108.3 . . ?
C19B C18A C17 118.1(2) . . ?
C19B C18A H15B 107.8 . . ?
C19B C18A H16B 107.8 . . ?
C18A C19A H17A 109.5 . . ?
C18A C19A H18A 109.5 . . ?
C18A C19A H19A 109.5 . . ?
H17A C19A H18A 109.5 . . ?
H17A C19A H19A 109.5 . . ?
H18A C19A H19A 109.5 . . ?
C18A C19B H18B 109.5 . . ?
C18A C19B H19B 109.5 . . ?
C18A C19B H17B 109.5 . . ?
H18B C19B H19B 109.5 . . ?
H18B C19B H17B 109.5 . . ?
H19B C19B H17B 109.5 . . ?

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
C8 C9 C4 C5 0.4(2) . . . . ?
C8 C9 C4 C3 -178.91(12) . . . . ?
C8 C9 C10 C8 -1.0(2) . . . 2_576 ?
C8 C9 C10 C11 178.25(12) . . . . ?
C8 C10 C11 C12 -179.92(13) 2_576 . . . ?
C8 C7 C6 C5 -0.7(2) . . . . ?
C5 C4 C3 C12 -178.79(12) . . . . ?
C5 C4 C3 C2 1.4(2) . . . . ?
C9 C8 C7 C6 -0.8(2) . . . . ?
C9 C4 C3 C12 0.5(2) . . . . ?
C9 C4 C3 C2 -179.33(12) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
C4 C5 C6 C7 2.0(2) . . . . ?
C4 C5 C1 O1 -176.51(12) . . . . ?
C4 C5 C1 N1 2.6(2) . . . . ?
C4 C9 C10 C8 179.92(11) . . . 2_576 ?
C4 C9 C10 C11 -0.8(2) . . . . ?
C4 C3 C12 C11 -0.5(2) . . . . ?
C4 C3 C2 O2 179.55(14) . . . . ?
C4 C3 C2 N1 0.2(2) . . . . ?
C10 C8 C9 C4 -179.92(11) 2_576 . . . ?
C10 C8 C9 C10 1.0(2) 2_576 . . . ?
C10 C8 C7 C6 -179.93(12) 2_576 . . . ?
C10 C9 C4 C5 179.43(11) . . . . ?
C10 C9 C4 C3 0.2(2) . . . . ?
C10 C11 C12 C3 -0.2(2) . . . . ?
C7 C8 C9 C4 0.9(2) . . . . ?
C7 C8 C9 C10 -178.12(12) . . . . ?
C6 C5 C4 C9 -1.8(2) . . . . ?
C6 C5 C4 C3 177.44(12) . . . . ?
C6 C5 C1 O1 3.2(2) . . . . ?
C6 C5 C1 N1 -177.65(12) . . . . ?
C1 N1 C2 O2 -179.73(13) . . . . ?
C1 N1 C2 C3 -0.3(2) . . . . ?
C1 N1 C13 C14 86.26(16) . . . . ?
C1 C5 C4 C9 177.93(11) . . . . ?
C1 C5 C4 C3 -2.8(2) . . . . ?
C1 C5 C6 C7 -177.76(12) . . . . ?
C12 C3 C2 O2 -0.2(2) . . . . ?
C12 C3 C2 N1 -179.62(12) . . . . ?
C14 C15 C16 C17 -177.33(15) . . . . ?
C15 C14 C13 N1 -171.98(13) . . . . ?
C15 C16 C17 C18A 177.52(18) . . . . ?
C2 N1 C1 O1 178.10(13) . . . . ?
C2 N1 C1 C5 -1.0(2) . . . . ?
C2 N1 C13 C14 -89.71(16) . . . . ?
C2 C3 C12 C11 179.33(13) . . . . ?
C13 N1 C1 O1 2.4(2) . . . . ?
C13 N1 C1 C5 -176.67(11) . . . . ?
C13 N1 C2 O2 -4.1(2) . . . . ?
C13 N1 C2 C3 175.32(11) . . . . ?
C13 C14 C15 C16 175.99(14) . . . . ?
C16 C17 C18A C19A -80.5(3) . . . . ?
C16 C17 C18A C19B -166.1(3) . . . . ?

_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_PDI_C8_0_1MPa
_database_code_depnum_ccdc_archive 'CCDC 2493916'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C8_0_1MPa       
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.473 Why?  
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT910_PDI_C8_0_1MPa       
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         92 Note   
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT911_PDI_C8_0_1MPa       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        1460 Report
RESPONSE: These reflections were probably affected by unexpected 
deviations in their intensities for symmetry equivalent measurements and 
omitted during initial data reduction.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-08-07

_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            PDI-C8
_chemical_name_systematic        N,N-Dioctyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C40 H42 N2 O4'
_chemical_formula_sum            'C40 H42 N2 O4'
_chemical_formula_weight         614.75
_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 -0.0004 0.0007 '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 -0.0003 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0008 0.0027 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7686(3)
_cell_length_b                   8.5193(4)
_cell_length_c                   20.2896(10)
_cell_angle_alpha                85.291(4)
_cell_angle_beta                 89.680(4)
_cell_angle_gamma                82.293(4)
_cell_volume                     814.05(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    659
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.6920
_cell_measurement_theta_min      5.3320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.042
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.067
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.012
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0072
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 0.473
_diffrn_reflns_Laue_measured_fraction_max 0.330
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            2702
_diffrn_reflns_point_group_measured_fraction_full 0.473
_diffrn_reflns_point_group_measured_fraction_max 0.330
_diffrn_reflns_theta_full        17.166
_diffrn_reflns_theta_max         23.095
_diffrn_reflns_theta_min         5.335
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.473
_diffrn_measured_fraction_theta_max 0.330
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     22.00  92.00   0.25    0.50  57.05   0.00-134.76    --   280
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0581261000
_diffrn_orient_matrix_UB_12      -0.0269199000
_diffrn_orient_matrix_UB_13      -0.0169111000
_diffrn_orient_matrix_UB_21      -0.0163403000
_diffrn_orient_matrix_UB_22      0.0486030000
_diffrn_orient_matrix_UB_23      -0.0150818000
_diffrn_orient_matrix_UB_31      0.0847956000
_diffrn_orient_matrix_UB_32      0.0181941000
_diffrn_orient_matrix_UB_33      0.0088502000
_diffrn_radiation_monochromator  synchrotron
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.4919
_diffrn_source                   synchrotron
_diffrn_special_details          
;
 Data were collected at room conditions (296 K / 0.1 MPa)
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1422
_reflns_number_total             2287
_reflns_odcompleteness_completeness 32.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     23.09
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0751
_refine_ls_restrained_S_all      1.028
_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)+(0.1745P)²+0.0192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2205
_refine_ls_wR_factor_ref         0.2543
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C16(H11,H12), C15(H9,H10), C17(H13,H14), C13(H5,H6), C14(H7,H8), C18(H15,H16),
  C19(H18,H17)
1.b Aromatic/amide H refined with riding coordinates:
 C11(H3), C7(H2), C12(H4), C6(H1)
1.c Idealised Me refined as rotating group:
 C20(H21,H19,H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8466(5) 0.6919(2) 0.68011(14) 0.0508(9) Uani 1 1 d . . . . .
O2 O 1.0045(5) 0.5217(2) 0.60338(13) 0.0663(10) Uani 1 1 d . . . . .
C10 C 0.2013(4) 0.8695(2) 0.48073(13) 0.0384(8) Uani 1 1 d . . . . .
C8 C 0.0203(5) 1.0516(2) 0.56579(13) 0.0392(7) Uani 1 1 d . . . . .
O1 O 0.6807(6) 0.8587(3) 0.75789(14) 0.0791(11) Uani 1 1 d . . . . .
C4 C 0.4275(5) 0.8461(2) 0.59026(13) 0.0390(8) Uani 1 1 d . . . . .
C1 C 0.6640(7) 0.8180(3) 0.70158(17) 0.0540(10) Uani 1 1 d . . . . .
C3 C 0.6227(5) 0.7198(2) 0.57033(14) 0.0424(8) Uani 1 1 d . . . . .
C9 C 0.2129(5) 0.9235(2) 0.54520(13) 0.0389(7) Uani 1 1 d . . . . .
C11 C 0.4008(5) 0.7457(2) 0.46297(15) 0.0439(8) Uani 1 1 d . . . . .
H3 H 0.3947 0.7116 0.4207 0.079(10) Uiso 1 1 calc R . . . .
C2 C 0.8405(5) 0.6358(3) 0.61735(16) 0.0459(9) Uani 1 1 d . . . . .
C5 C 0.4426(5) 0.8992(3) 0.65416(15) 0.0460(9) Uani 1 1 d . . . . .
C7 C 0.0456(6) 1.1005(3) 0.62882(16) 0.0504(9) Uani 1 1 d . . . . .
H2 H -0.0799 1.1850 0.6422 0.104(14) Uiso 1 1 calc R . . . .
C12 C 0.6111(5) 0.6714(2) 0.50751(14) 0.0439(8) Uani 1 1 d . . . . .
H4 H 0.7429 0.5893 0.4945 0.067(9) Uiso 1 1 calc R . . . .
C6 C 0.2581(7) 1.0243(3) 0.67288(17) 0.0542(10) Uani 1 1 d . . . . .
H1 H 0.2727 1.0593 0.7148 0.092(11) Uiso 1 1 calc R . . . .
C16 C 1.0037(8) 0.2119(4) 0.8400(2) 0.0715(13) Uani 1 1 d . . . . .
H11 H 0.8664 0.2522 0.8721 0.102(16) Uiso 1 1 calc R . . . .
H12 H 0.9038 0.1638 0.8072 0.089(11) Uiso 1 1 calc R . . . .
C15 C 1.1390(8) 0.3516(3) 0.8060(2) 0.0679(12) Uani 1 1 d . . . . .
H9 H 1.2209 0.4076 0.8392 0.065(8) Uiso 1 1 calc R . . . .
H10 H 1.2899 0.3109 0.7772 0.115(17) Uiso 1 1 calc R . . . .
C17 C 1.2215(10) 0.0855(4) 0.8749(2) 0.0802(15) Uani 1 1 d . . . . .
H13 H 1.3099 0.1310 0.9104 0.071(9) Uiso 1 1 calc R . . . .
H14 H 1.3678 0.0513 0.8438 0.119(19) Uiso 1 1 calc R . . . .
C13 C 1.0528(6) 0.6018(3) 0.72797(17) 0.0573(10) Uani 1 1 d . . . . .
H5 H 1.1100 0.6723 0.7590 0.082(10) Uiso 1 1 calc R . . . .
H6 H 1.2199 0.5580 0.7048 0.080(10) Uiso 1 1 calc R . . . .
C14 C 0.9197(7) 0.4667(4) 0.76553(19) 0.0668(12) Uani 1 1 d . . . . .
H7 H 0.7744 0.5116 0.7948 0.082(12) Uiso 1 1 calc R . . . .
H8 H 0.8300 0.4090 0.7342 0.074(9) Uiso 1 1 calc R . . . .
C18 C 1.0866(11) -0.0579(5) 0.9032(3) 0.0873(18) Uani 1 1 d . . . . .
H15 H 0.9501 -0.0241 0.9365 0.100(17) Uiso 1 1 calc R . . . .
H16 H 0.9847 -0.0971 0.8681 0.138(18) Uiso 1 1 calc R . . . .
C19 C 1.2978(14) -0.1924(6) 0.9337(4) 0.116(2) Uani 1 1 d . . . . .
H18 H 1.4327 -0.2283 0.9004 0.24(5) Uiso 1 1 calc R . . . .
H17 H 1.4013 -0.1538 0.9687 0.134(19) Uiso 1 1 calc R . . . .
C20 C 1.155(2) -0.3303(8) 0.9617(5) 0.151(3) Uani 1 1 d . . . . .
H21 H 1.1516 -0.4054 0.9290 0.36(10) Uiso 1 1 calc R . . . .
H19 H 0.9643 -0.2924 0.9739 0.26(6) Uiso 1 1 calc R . . . .
H20 H 1.2570 -0.3810 1.0001 0.16(2) Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.387(5) . ?
N1 C2 1.398(5) . ?
N1 C13 1.478(2) . ?
O2 C2 1.215(5) . ?
C10 C8 1.475(2) 2_576 ?
C10 C9 1.426(4) . ?
C10 C11 1.392(4) . ?
C8 C10 1.475(2) 2_576 ?
C8 C9 1.418(4) . ?
C8 C7 1.388(4) . ?
O1 C1 1.227(5) . ?
C4 C3 1.409(4) . ?
C4 C9 1.431(2) . ?
C4 C5 1.413(5) . ?
C1 C5 1.492(3) . ?
C3 C2 1.483(3) . ?
C3 C12 1.375(4) . ?
C11 H3 0.9300 . ?
C11 C12 1.403(3) . ?
C5 C6 1.366(5) . ?
C7 H2 0.9300 . ?
C7 C6 1.409(3) . ?
C12 H4 0.9300 . ?
C6 H1 0.9300 . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C15 1.541(4) . ?
C16 C17 1.524(4) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C14 1.528(3) . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C18 1.525(6) . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C13 C14 1.534(4) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C18 H15 0.9700 . ?
C18 H16 0.9700 . ?
C18 C19 1.515(5) . ?
C19 H18 0.9700 . ?
C19 H17 0.9700 . ?
C19 C20 1.506(9) . ?
C20 H21 0.9600 . ?
C20 H19 0.9600 . ?
C20 H20 0.9600 . ?

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 C2 125.09(19) . . ?
C1 N1 C13 118.3(3) . . ?
C2 N1 C13 116.5(3) . . ?
C9 C10 C8 118.9(2) . 2_576 ?
C11 C10 C8 121.7(3) . 2_576 ?
C11 C10 C9 119.36(18) . . ?
C9 C8 C10 119.0(3) . 2_576 ?
C7 C8 C10 121.6(3) . 2_576 ?
C7 C8 C9 119.43(19) . . ?
C3 C4 C9 119.9(3) . . ?
C5 C4 C3 120.84(18) . . ?
C5 C4 C9 119.2(3) . . ?
N1 C1 C5 117.4(3) . . ?
O1 C1 N1 121.2(2) . . ?
O1 C1 C5 121.4(3) . . ?
C4 C3 C2 120.3(3) . . ?
C12 C3 C4 120.51(18) . . ?
C12 C3 C2 119.2(3) . . ?
C10 C9 C4 118.7(2) . . ?
C8 C9 C10 122.14(18) . . ?
C8 C9 C4 119.2(3) . . ?
C10 C11 H3 119.3 . . ?
C10 C11 C12 121.4(3) . . ?
C12 C11 H3 119.3 . . ?
N1 C2 C3 116.8(3) . . ?
O2 C2 N1 120.6(2) . . ?
O2 C2 C3 122.6(3) . . ?
C4 C5 C1 119.5(3) . . ?
C6 C5 C4 120.84(19) . . ?
C6 C5 C1 119.7(3) . . ?
C8 C7 H2 119.4 . . ?
C8 C7 C6 121.1(3) . . ?
C6 C7 H2 119.4 . . ?
C3 C12 C11 120.1(3) . . ?
C3 C12 H4 119.9 . . ?
C11 C12 H4 119.9 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H1 119.9 . . ?
C7 C6 H1 119.9 . . ?
H11 C16 H12 107.8 . . ?
C15 C16 H11 109.1 . . ?
C15 C16 H12 109.1 . . ?
C17 C16 H11 109.1 . . ?
C17 C16 H12 109.1 . . ?
C17 C16 C15 112.5(3) . . ?
C16 C15 H9 109.4 . . ?
C16 C15 H10 109.4 . . ?
H9 C15 H10 108.0 . . ?
C14 C15 C16 111.0(3) . . ?
C14 C15 H9 109.4 . . ?
C14 C15 H10 109.4 . . ?
C16 C17 H13 109.3 . . ?
C16 C17 H14 109.3 . . ?
C16 C17 C18 111.6(3) . . ?
H13 C17 H14 108.0 . . ?
C18 C17 H13 109.3 . . ?
C18 C17 H14 109.3 . . ?
N1 C13 H5 109.7 . . ?
N1 C13 H6 109.7 . . ?
N1 C13 C14 110.0(2) . . ?
H5 C13 H6 108.2 . . ?
C14 C13 H5 109.7 . . ?
C14 C13 H6 109.7 . . ?
C15 C14 C13 111.9(2) . . ?
C15 C14 H7 109.2 . . ?
C15 C14 H8 109.2 . . ?
C13 C14 H7 109.2 . . ?
C13 C14 H8 109.2 . . ?
H7 C14 H8 107.9 . . ?
C17 C18 H15 108.8 . . ?
C17 C18 H16 108.8 . . ?
H15 C18 H16 107.7 . . ?
C19 C18 C17 113.6(4) . . ?
C19 C18 H15 108.8 . . ?
C19 C18 H16 108.8 . . ?
C18 C19 H18 109.3 . . ?
C18 C19 H17 109.3 . . ?
H18 C19 H17 107.9 . . ?
C20 C19 C18 111.8(6) . . ?
C20 C19 H18 109.3 . . ?
C20 C19 H17 109.3 . . ?
C19 C20 H21 109.5 . . ?
C19 C20 H19 109.5 . . ?
C19 C20 H20 109.5 . . ?
H21 C20 H19 109.5 . . ?
H21 C20 H20 109.5 . . ?
H19 C20 H20 109.5 . . ?

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
N1 C1 C5 C4 -0.1(3) . . . . ?
N1 C1 C5 C6 -179.8(2) . . . . ?
N1 C13 C14 C15 169.3(3) . . . . ?
C10 C8 C9 C10 0.7(3) 2_576 . . . ?
C10 C8 C9 C4 -179.74(15) 2_576 . . . ?
C10 C8 C7 C6 180.0(2) 2_576 . . . ?
C10 C11 C12 C3 0.3(3) . . . . ?
C8 C10 C9 C8 -0.7(3) 2_576 . . . ?
C8 C10 C9 C4 179.74(15) 2_576 . . . ?
C8 C10 C11 C12 179.95(16) 2_576 . . . ?
C8 C7 C6 C5 -0.5(4) . . . . ?
O1 C1 C5 C4 -178.7(2) . . . . ?
O1 C1 C5 C6 1.6(4) . . . . ?
C4 C3 C2 N1 -2.2(3) . . . . ?
C4 C3 C2 O2 176.5(2) . . . . ?
C4 C3 C12 C11 -1.2(3) . . . . ?
C4 C5 C6 C7 1.2(4) . . . . ?
C1 N1 C2 O2 -178.0(2) . . . . ?
C1 N1 C2 C3 0.7(3) . . . . ?
C1 N1 C13 C14 88.1(3) . . . . ?
C1 C5 C6 C7 -179.1(2) . . . . ?
C3 C4 C9 C10 0.3(3) . . . . ?
C3 C4 C9 C8 -179.25(17) . . . . ?
C3 C4 C5 C1 -1.4(3) . . . . ?
C3 C4 C5 C6 178.3(2) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C9 C8 C7 C6 -0.4(4) . . . . ?
C9 C4 C3 C2 -178.17(16) . . . . ?
C9 C4 C3 C12 0.9(3) . . . . ?
C9 C4 C5 C1 179.37(18) . . . . ?
C9 C4 C5 C6 -1.0(3) . . . . ?
C11 C10 C9 C8 178.39(17) . . . . ?
C11 C10 C9 C4 -1.2(3) . . . . ?
C2 N1 C1 O1 179.0(2) . . . . ?
C2 N1 C1 C5 0.4(4) . . . . ?
C2 N1 C13 C14 -87.9(4) . . . . ?
C2 C3 C12 C11 177.86(17) . . . . ?
C5 C4 C3 C2 2.6(3) . . . . ?
C5 C4 C3 C12 -178.37(17) . . . . ?
C5 C4 C9 C10 179.56(17) . . . . ?
C5 C4 C9 C8 0.0(3) . . . . ?
C7 C8 C9 C10 -178.86(18) . . . . ?
C7 C8 C9 C4 0.7(3) . . . . ?
C12 C3 C2 N1 178.71(18) . . . . ?
C12 C3 C2 O2 -2.6(4) . . . . ?
C16 C15 C14 C13 -176.7(4) . . . . ?
C16 C17 C18 C19 175.5(5) . . . . ?
C15 C16 C17 C18 -175.2(5) . . . . ?
C17 C16 C15 C14 173.9(4) . . . . ?
C17 C18 C19 C20 179.2(7) . . . . ?
C13 N1 C1 O1 3.3(4) . . . . ?
C13 N1 C1 C5 -175.25(18) . . . . ?
C13 N1 C2 O2 -2.3(3) . . . . ?
C13 N1 C2 C3 176.47(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.151
_oxdiff_exptl_absorpt_empirical_full_min 0.479
####################################################################### 
# 
# 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_PDI_C7_100K
_database_code_depnum_ccdc_archive 'CCDC 2493915'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-03-06 downloaded from the CCDC.
;
_audit_creation_date             2025-03-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PDI-C7
_chemical_name_systematic        'N,N diheptyl 3,4,9,10 perylenedicarboximide'
_chemical_formula_moiety         'C38 H38 N2 O4'
_chemical_formula_sum            'C38 H38 N2 O4'
_chemical_formula_weight         586.70
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.78950(10)
_cell_length_b                   8.2562(2)
_cell_length_c                   18.9401(4)
_cell_angle_alpha                79.3950(10)
_cell_angle_beta                 90.1040(10)
_cell_angle_gamma                82.5010(10)
_cell_volume                     729.60(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6836
_cell_measurement_temperature    101.00
_cell_measurement_theta_max      72.594
_cell_measurement_theta_min      4.753
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1266 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.8524.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.034
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25548
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.587
_diffrn_reflns_theta_min         4.752
_diffrn_ambient_temperature      101.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 Data were collected at low temperature of 100 K.
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2414
_reflns_number_total             2862
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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         0.339
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2862
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.072
_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)+(0.0733P)²+0.2755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1390
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Sof(H15B)=Sof(H16B)=Sof(C19B)=Sof(H18B)=Sof(H19B)=Sof(H17B)=1-FVAR(1)
 Sof(H16A)=Sof(H15A)=Sof(C19A)=Sof(H17A)=Sof(H18A)=Sof(H19A)=FVAR(1)
2.a Secondary CH2 refined with riding coordinates:
 C14(H7,H8), C13(H5,H6), C15(H9,H10), C16(H11,H12), C17(H13,H14), C18(H16A,
 H15A), C18(H15B,H16B)
2.b Me refined with riding coordinates:
 C19A(H17A,H18A,H19A), C19B(H18B,H19B,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H1), C7(H2), C11(H3), C12(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0010(2) 0.59006(12) 0.38717(5) 0.0231(3) Uani 1 1 d . . . . .
O2 O 0.6564(2) 1.04471(13) 0.22172(5) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.8322(2) 0.81863(14) 0.30478(6) 0.0190(3) Uani 1 1 d . . . . .
C5 C 0.6197(3) 0.76778(16) 0.42326(7) 0.0171(3) Uani 1 1 d . . . . .
C10 C 0.0098(3) 1.09981(16) 0.42869(7) 0.0168(3) Uani 1 1 d . . . . .
C6 C 0.6179(3) 0.67483(16) 0.49125(7) 0.0179(3) Uani 1 1 d . . . . .
H1 H 0.756754 0.581118 0.505587 0.021 Uiso 1 1 calc R U . . .
C8 C 0.2073(3) 0.85432(16) 0.52085(7) 0.0161(3) Uani 1 1 d . . . . .
C9 C 0.2086(3) 0.95483(16) 0.45099(7) 0.0165(3) Uani 1 1 d . . . . .
C4 C 0.4186(3) 0.91017(16) 0.40204(7) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.8328(3) 0.71703(17) 0.37202(7) 0.0183(3) Uani 1 1 d . . . . .
C7 C 0.4121(3) 0.71745(16) 0.53966(7) 0.0176(3) Uani 1 1 d . . . . .
H2 H 0.412866 0.651194 0.586340 0.021 Uiso 1 1 calc R U . . .
C11 C 0.0282(3) 1.19455(17) 0.36067(7) 0.0193(3) Uani 1 1 d . . . . .
H3 H -0.102557 1.292045 0.346069 0.023 Uiso 1 1 calc R U . . .
C2 C 0.6430(3) 0.96348(17) 0.28154(7) 0.0190(3) Uani 1 1 d . . . . .
C3 C 0.4276(3) 1.00912(17) 0.33329(7) 0.0179(3) Uani 1 1 d . . . . .
C12 C 0.2350(3) 1.14980(17) 0.31309(7) 0.0195(3) Uani 1 1 d . . . . .
H4 H 0.242629 1.216526 0.266753 0.023 Uiso 1 1 calc R U . . .
C14 C 0.9128(3) 0.64692(18) 0.21055(8) 0.0227(3) Uani 1 1 d . . . . .
H7 H 0.839667 0.557572 0.244807 0.027 Uiso 1 1 calc R U . . .
H8 H 0.752687 0.709749 0.179795 0.027 Uiso 1 1 calc R U . . .
C13 C 1.0348(3) 0.76361(18) 0.25247(8) 0.0206(3) Uani 1 1 d . . . . .
H5 H 1.210233 0.705743 0.278213 0.025 Uiso 1 1 calc R U . . .
H6 H 1.082639 0.861879 0.218590 0.025 Uiso 1 1 calc R U . . .
C15 C 1.1292(3) 0.56885(19) 0.16362(8) 0.0252(3) Uani 1 1 d . . . . .
H9 H 1.295608 0.513251 0.193878 0.030 Uiso 1 1 calc R U . . .
H10 H 1.191967 0.657838 0.127091 0.030 Uiso 1 1 calc R U . . .
C16 C 1.0151(3) 0.44230(19) 0.12564(8) 0.0263(3) Uani 1 1 d . . . . .
H11 H 0.944367 0.356010 0.162012 0.032 Uiso 1 1 calc R U . . .
H12 H 0.854187 0.498993 0.093635 0.032 Uiso 1 1 calc R U . . .
C17 C 1.2365(3) 0.3587(2) 0.08133(11) 0.0387(4) Uani 1 1 d . . . . .
H13 H 1.401382 0.307200 0.112968 0.046 Uiso 1 1 calc R U . . .
H14 H 1.300354 0.444718 0.043575 0.046 Uiso 1 1 calc R U . . .
C18 C 1.1309(4) 0.2253(3) 0.04567(13) 0.0533(6) Uani 1 1 d . . . . .
H16A H 0.937346 0.267159 0.026443 0.064 Uiso 0.505(5) 1 calc R U P A 1
H15A H 1.251077 0.210302 0.004283 0.064 Uiso 0.505(5) 1 calc R U P A 1
H15B H 1.025473 0.156181 0.081759 0.064 Uiso 0.495(5) 1 calc R U P A 2
H16B H 0.994957 0.282024 0.006678 0.064 Uiso 0.495(5) 1 calc R U P A 2
C19A C 1.1268(7) 0.0778(4) 0.08709(16) 0.0276(8) Uani 0.505(5) 1 d . . P A 1
H17A H 1.056112 0.002387 0.059036 0.041 Uiso 0.505(5) 1 calc R U P A 1
H18A H 1.318077 0.032332 0.105335 0.041 Uiso 0.505(5) 1 calc R U P A 1
H19A H 1.003362 0.089368 0.127564 0.041 Uiso 0.505(5) 1 calc R U P A 1
C19B C 1.3342(8) 0.1168(5) 0.0162(2) 0.0459(12) Uani 0.495(5) 1 d . . P A 2
H18B H 1.239101 0.038010 -0.004794 0.069 Uiso 0.495(5) 1 calc R U P A 2
H19B H 1.436471 0.181969 -0.021156 0.069 Uiso 0.495(5) 1 calc R U P A 2
H17B H 1.467120 0.055578 0.054253 0.069 Uiso 0.495(5) 1 calc R U P A 2


_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 1.2240(18) . ?
O2 C2 1.2123(17) . ?
N1 C1 1.3898(18) . ?
N1 C2 1.4024(19) . ?
N1 C13 1.4777(17) . ?
C5 C6 1.373(2) . ?
C5 C4 1.414(2) . ?
C5 C1 1.4835(19) . ?
C10 C8 1.4738(19) 2_576 ?
C10 C9 1.426(2) . ?
C10 C11 1.3881(19) . ?
C6 H1 0.9500 . ?
C6 C7 1.4025(19) . ?
C8 C9 1.4270(19) . ?
C8 C7 1.388(2) . ?
C9 C4 1.428(2) . ?
C4 C3 1.4081(19) . ?
C7 H2 0.9500 . ?
C11 H3 0.9500 . ?
C11 C12 1.400(2) . ?
C2 C3 1.4851(19) . ?
C3 C12 1.379(2) . ?
C12 H4 0.9500 . ?
C14 H7 0.9900 . ?
C14 H8 0.9900 . ?
C14 C13 1.5252(18) . ?
C14 C15 1.5230(19) . ?
C13 H5 0.9900 . ?
C13 H6 0.9900 . ?
C15 H9 0.9900 . ?
C15 H10 0.9900 . ?
C15 C16 1.5272(19) . ?
C16 H11 0.9900 . ?
C16 H12 0.9900 . ?
C16 C17 1.527(2) . ?
C17 H13 0.9900 . ?
C17 H14 0.9900 . ?
C17 C18 1.531(2) . ?
C18 H16A 0.9900 . ?
C18 H15A 0.9900 . ?
C18 H15B 0.9900 . ?
C18 H16B 0.9900 . ?
C18 C19A 1.324(4) . ?
C18 C19B 1.421(4) . ?
C19A H17A 0.9800 . ?
C19A H18A 0.9800 . ?
C19A H19A 0.9800 . ?
C19B H18B 0.9800 . ?
C19B H19B 0.9800 . ?
C19B H17B 0.9800 . ?

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 C2 124.95(12) . . ?
C1 N1 C13 117.23(12) . . ?
C2 N1 C13 117.70(11) . . ?
C6 C5 C4 120.26(13) . . ?
C6 C5 C1 119.52(13) . . ?
C4 C5 C1 120.22(12) . . ?
C9 C10 C8 118.79(13) . 2_576 ?
C11 C10 C8 121.98(13) . 2_576 ?
C11 C10 C9 119.22(13) . . ?
C5 C6 H1 119.8 . . ?
C5 C6 C7 120.37(13) . . ?
C7 C6 H1 119.8 . . ?
C9 C8 C10 118.93(13) . 2_576 ?
C7 C8 C10 121.87(13) . 2_576 ?
C7 C8 C9 119.19(13) . . ?
C10 C9 C8 122.27(13) . . ?
C10 C9 C4 118.80(13) . . ?
C8 C9 C4 118.93(13) . . ?
C5 C4 C9 119.78(13) . . ?
C3 C4 C5 120.21(13) . . ?
C3 C4 C9 120.01(13) . . ?
O1 C1 N1 120.64(13) . . ?
O1 C1 C5 122.11(13) . . ?
N1 C1 C5 117.25(12) . . ?
C6 C7 H2 119.3 . . ?
C8 C7 C6 121.45(13) . . ?
C8 C7 H2 119.3 . . ?
C10 C11 H3 119.2 . . ?
C10 C11 C12 121.55(13) . . ?
C12 C11 H3 119.2 . . ?
O2 C2 N1 120.70(13) . . ?
O2 C2 C3 122.64(13) . . ?
N1 C2 C3 116.66(12) . . ?
C4 C3 C2 120.65(13) . . ?
C12 C3 C4 120.23(13) . . ?
C12 C3 C2 119.12(13) . . ?
C11 C12 H4 119.9 . . ?
C3 C12 C11 120.19(13) . . ?
C3 C12 H4 119.9 . . ?
H7 C14 H8 107.8 . . ?
C13 C14 H7 109.1 . . ?
C13 C14 H8 109.1 . . ?
C15 C14 H7 109.1 . . ?
C15 C14 H8 109.1 . . ?
C15 C14 C13 112.60(11) . . ?
N1 C13 C14 111.13(11) . . ?
N1 C13 H5 109.4 . . ?
N1 C13 H6 109.4 . . ?
C14 C13 H5 109.4 . . ?
C14 C13 H6 109.4 . . ?
H5 C13 H6 108.0 . . ?
C14 C15 H9 109.0 . . ?
C14 C15 H10 109.0 . . ?
C14 C15 C16 112.97(11) . . ?
H9 C15 H10 107.8 . . ?
C16 C15 H9 109.0 . . ?
C16 C15 H10 109.0 . . ?
C15 C16 H11 109.0 . . ?
C15 C16 H12 109.0 . . ?
H11 C16 H12 107.8 . . ?
C17 C16 C15 112.79(12) . . ?
C17 C16 H11 109.0 . . ?
C17 C16 H12 109.0 . . ?
C16 C17 H13 108.8 . . ?
C16 C17 H14 108.8 . . ?
C16 C17 C18 113.72(14) . . ?
H13 C17 H14 107.7 . . ?
C18 C17 H13 108.8 . . ?
C18 C17 H14 108.8 . . ?
C17 C18 H16A 108.2 . . ?
C17 C18 H15A 108.2 . . ?
C17 C18 H15B 107.9 . . ?
C17 C18 H16B 107.9 . . ?
H16A C18 H15A 107.4 . . ?
H15B C18 H16B 107.2 . . ?
C19A C18 C17 116.3(2) . . ?
C19A C18 H16A 108.2 . . ?
C19A C18 H15A 108.2 . . ?
C19B C18 C17 117.8(2) . . ?
C19B C18 H15B 107.9 . . ?
C19B C18 H16B 107.9 . . ?
C18 C19A H17A 109.5 . . ?
C18 C19A H18A 109.5 . . ?
C18 C19A H19A 109.5 . . ?
H17A C19A H18A 109.5 . . ?
H17A C19A H19A 109.5 . . ?
H18A C19A H19A 109.5 . . ?
C18 C19B H18B 109.5 . . ?
C18 C19B H19B 109.5 . . ?
C18 C19B H17B 109.5 . . ?
H18B C19B H19B 109.5 . . ?
H18B C19B H17B 109.5 . . ?
H19B C19B H17B 109.5 . . ?

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
O2 C2 C3 C4 179.46(12) . . . . ?
O2 C2 C3 C12 -0.3(2) . . . . ?
N1 C2 C3 C4 0.21(18) . . . . ?
N1 C2 C3 C12 -179.58(11) . . . . ?
C5 C6 C7 C8 -0.57(19) . . . . ?
C5 C4 C3 C2 1.50(19) . . . . ?
C5 C4 C3 C12 -178.71(11) . . . . ?
C10 C8 C9 C10 1.1(2) 2_576 . . . ?
C10 C8 C9 C4 -179.87(10) 2_576 . . . ?
C10 C8 C7 C6 -179.99(11) 2_576 . . . ?
C10 C9 C4 C5 179.38(11) . . . . ?
C10 C9 C4 C3 0.31(19) . . . . ?
C10 C11 C12 C3 -0.2(2) . . . . ?
C6 C5 C4 C9 -1.58(19) . . . . ?
C6 C5 C4 C3 177.49(11) . . . . ?
C6 C5 C1 O1 3.29(19) . . . . ?
C6 C5 C1 N1 -177.73(11) . . . . ?
C8 C10 C9 C8 -1.1(2) 2_576 . . . ?
C8 C10 C9 C4 179.86(10) 2_576 . . . ?
C8 C10 C11 C12 -179.91(11) 2_576 . . . ?
C8 C9 C4 C5 0.27(19) . . . . ?
C8 C9 C4 C3 -178.80(11) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
C9 C8 C7 C6 -0.74(19) . . . . ?
C9 C4 C3 C2 -179.44(11) . . . . ?
C9 C4 C3 C12 0.4(2) . . . . ?
C4 C5 C6 C7 1.73(19) . . . . ?
C4 C5 C1 O1 -176.23(11) . . . . ?
C4 C5 C1 N1 2.75(18) . . . . ?
C4 C3 C12 C11 -0.4(2) . . . . ?
C1 N1 C2 O2 -179.66(12) . . . . ?
C1 N1 C2 C3 -0.40(19) . . . . ?
C1 N1 C13 C14 86.52(14) . . . . ?
C1 C5 C6 C7 -177.79(10) . . . . ?
C1 C5 C4 C9 177.94(10) . . . . ?
C1 C5 C4 C3 -2.99(19) . . . . ?
C7 C8 C9 C10 -178.21(11) . . . . ?
C7 C8 C9 C4 0.86(19) . . . . ?
C11 C10 C9 C8 178.15(11) . . . . ?
C11 C10 C9 C4 -0.93(19) . . . . ?
C2 N1 C1 O1 177.95(12) . . . . ?
C2 N1 C1 C5 -1.04(19) . . . . ?
C2 N1 C13 C14 -89.70(14) . . . . ?
C2 C3 C12 C11 179.40(11) . . . . ?
C14 C15 C16 C17 -177.42(14) . . . . ?
C13 N1 C1 O1 2.03(18) . . . . ?
C13 N1 C1 C5 -176.96(10) . . . . ?
C13 N1 C2 O2 -3.76(19) . . . . ?
C13 N1 C2 C3 175.50(10) . . . . ?
C13 C14 C15 C16 175.84(12) . . . . ?
C15 C14 C13 N1 -172.08(12) . . . . ?
C15 C16 C17 C18 177.22(16) . . . . ?
C16 C17 C18 C19A -80.4(2) . . . . ?
C16 C17 C18 C19B -167.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
