# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_C6_0_1MPa
_database_code_depnum_ccdc_archive 'CCDC 2412018'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C6_0_1MPa       
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.448 Why?  
RESPONSE: These data come from a high-pressure experiment and part of the 
reflections could not be collected due to the limited DAC opening angle and the 
measurement strategy. 
;
_vrf_PLAT084_PDI_C6_0_1MPa       
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.38 Report 
RESPONSE: The high factor results from weak diffraction. Additionally, due 
to the high-pressure DAC used in this experiment, some diffraction data 
were omitted. 
;
_vrf_PLAT911_PDI_C6_0_1MPa       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600       1412 Report
                1  0  0,   2  0  0,   3  0  0,   4  0  0,   5  0  0,  -5  1  0, 
               -4  1  0,  -3  1  0,  -2  1  0,  -1  1  0,   0  1  0,   1  1  0, 
                2  1  0,   3  1  0,   4  1  0,   5  1  0,  -5  2  0,  -4  2  0, 
               -3  2  0,  -1  2  0,   0  2  0,   1  2  0,   2  2  0,   3  2  0, 
                4  2  0,   5  2  0,  -2  3  0,  -1  3  0,   0  3  0,   1  3  0, 
                2  3  0,   3  3  0,   4  3  0,   5  3  0,  -4  4  0,  -3  4  0, 
               -1  4  0,   0  4  0,   1  4  0,   2  4  0,   3  4  0,   4  4  0, 
                5  4  0,  -4  5  0,  -3  5  0,  -1  5  0,   0  5  0,   1  5  0, 
                2  5  0,   3  5  0,   4  5  0,   5  5  0,  -4  6  0,  -3  6  0, 
               -1  6  0,   0  6  0,   1  6  0,   2  6  0,   3  6  0,   4  6  0, 
               -3  7  0,  -1  7  0,   0  7  0,   1  7  0,   2  7  0,   3  7  0, 
                4  7  0,  -1  8  0,   0  8  0,   1  8  0,   2  8  0,   3  8  0, 
                4  8  0,  -1  9  0,   0  9  0,   1  9  0,   2  9  0,   3  9  0, 
                0 10  0,   1 10  0,  -1-10  1,   0-10  1,  -3 -9  1,  -2 -9  1, 
               -1 -9  1,   0 -9  1,   1 -9  1,  -3 -8  1,  -2 -8  1,  -1 -8  1, 
                0 -8  1,   1 -8  1,  -4 -7  1,  -3 -7  1,  -2 -7  1,  -1 -7  1, 

RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-06-07
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   4.77230(10)
_cell_length_b                   8.57560(10)
_cell_length_c                   17.6181(2)
_cell_angle_alpha                81.7340(10)
_cell_angle_beta                 84.8810(10)
_cell_angle_gamma                83.0100(10)
_cell_volume                     706.342(19)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1503
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2800
_cell_measurement_theta_min      4.3290
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.045
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00206
_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    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_preparation       'mounted in a diamond-anvil cell'
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.072
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0072
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 0.448
_diffrn_reflns_Laue_measured_fraction_max 0.331
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            2943
_diffrn_reflns_point_group_measured_fraction_full 0.448
_diffrn_reflns_point_group_measured_fraction_max 0.331
_diffrn_reflns_theta_full        17.159
_diffrn_reflns_theta_max         25.271
_diffrn_reflns_theta_min         1.620
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.448
_diffrn_measured_fraction_theta_max 0.331
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     27.00  87.00   0.20    0.50  57.05   0.00-134.76    --   300
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.49172
_diffrn_source                   synchrotron
_diffrn_special_details          
'Data were collected under room conditions (296 K/0.1 MPa)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2059
_reflns_number_total             2560
_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         0.370
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.711
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.1202
_refine_ls_restrained_S_all      1.711
_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          0.3750
_refine_ls_wR_factor_ref         0.3800
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C15(H9,H10), C16(H11,H12), C14(H7,H8), C13(H5,H6), C17(H13,H14)
1.b Aromatic/amide H refined with riding coordinates:
 C7(H2), C6(H1), C11(H3), C12(H4)
1.c Idealised Me refined as rotating group:
 C18(H15,H16,H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O -0.0255(4) 0.4250(2) 0.61704(8) 0.0606(7) Uani 1 1 d . . . . .
O1 O 0.2540(5) 0.0207(3) 0.80026(8) 0.0750(10) Uani 1 1 d . . . . .
N1 N 0.1106(4) 0.2213(3) 0.70831(8) 0.0482(6) Uani 1 1 d . . . . .
C4 C 0.5508(5) 0.1097(3) 0.60412(8) 0.0378(6) Uani 1 1 d . . . . .
C7 C 0.9163(5) -0.1609(3) 0.65142(9) 0.0480(7) Uani 1 1 d . . . . .
H2 H 1.035978 -0.251030 0.667769 0.058 Uiso 1 1 calc R U . . .
C8 C 0.9603(4) -0.0828(3) 0.57710(8) 0.0369(6) Uani 1 1 d . . . . .
C10 C 0.8066(5) 0.1386(2) 0.47633(8) 0.0364(6) Uani 1 1 d . . . . .
C15 C -0.2070(5) 0.4997(3) 0.85314(11) 0.0590(8) Uani 1 1 d . . . . .
H9 H -0.290525 0.424534 0.892538 0.071 Uiso 1 1 calc R U . . .
H10 H -0.355885 0.552962 0.821578 0.071 Uiso 1 1 calc R U . . .
C3 C 0.3653(5) 0.2449(3) 0.58038(9) 0.0396(6) Uani 1 1 d . . . . .
C2 C 0.1335(5) 0.3052(3) 0.63457(10) 0.0458(7) Uani 1 1 d . . . . .
C6 C 0.6945(6) -0.1059(3) 0.70209(10) 0.0499(7) Uani 1 1 d . . . . .
H1 H 0.667710 -0.160433 0.751301 0.060 Uiso 1 1 calc R U . . .
C9 C 0.7759(4) 0.0550(2) 0.55231(8) 0.0351(5) Uani 1 1 d . . . . .
C5 C 0.5163(5) 0.0283(3) 0.67937(9) 0.0429(6) Uani 1 1 d . . . . .
C16 C -0.0802(6) 0.6224(4) 0.89137(12) 0.0599(9) Uani 1 1 d . . . . .
H11 H 0.066879 0.568439 0.923368 0.072 Uiso 1 1 calc R U . . .
H12 H 0.006730 0.695869 0.851809 0.072 Uiso 1 1 calc R U . . .
C11 C 0.6161(5) 0.2707(3) 0.45512(9) 0.0406(6) Uani 1 1 d . . . . .
H3 H 0.636729 0.325731 0.405839 0.049 Uiso 1 1 calc R U . . .
C12 C 0.3933(5) 0.3228(3) 0.50634(9) 0.0426(6) Uani 1 1 d . . . . .
H4 H 0.265197 0.409461 0.490424 0.051 Uiso 1 1 calc R U . . .
C14 C 0.0187(5) 0.4107(3) 0.80314(11) 0.0554(8) Uani 1 1 d . . . . .
H7 H 0.167070 0.357477 0.834860 0.066 Uiso 1 1 calc R U . . .
H8 H 0.102768 0.486251 0.764046 0.066 Uiso 1 1 calc R U . . .
C13 C -0.1041(5) 0.2878(4) 0.76404(12) 0.0553(8) Uani 1 1 d . . . . .
H5 H -0.163503 0.203340 0.802591 0.066 Uiso 1 1 calc R U . . .
H6 H -0.268711 0.337641 0.737717 0.066 Uiso 1 1 calc R U . . .
C1 C 0.2860(5) 0.0850(3) 0.73458(10) 0.0509(7) Uani 1 1 d . . . . .
C18 C -0.1661(11) 0.8321(6) 0.9797(2) 0.0976(16) Uani 1 1 d . . . . .
H15 H -0.021040 0.775661 1.010731 0.146 Uiso 1 1 calc R U . . .
H16 H -0.307973 0.886130 1.011755 0.146 Uiso 1 1 calc R U . . .
H17 H -0.084384 0.908063 0.941363 0.146 Uiso 1 1 calc R U . . .
C17 C -0.3012(7) 0.7152(4) 0.94059(14) 0.0710(10) Uani 1 1 d . . . . .
H13 H -0.392395 0.642011 0.979378 0.085 Uiso 1 1 calc R U . . .
H14 H -0.445007 0.772628 0.908459 0.085 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.220(2) . ?
O1 C1 1.213(3) . ?
N1 C2 1.393(3) . ?
N1 C13 1.476(2) . ?
N1 C1 1.399(3) . ?
C4 C3 1.407(3) . ?
C4 C9 1.426(3) . ?
C4 C5 1.412(3) . ?
C7 H2 0.9300 . ?
C7 C8 1.393(3) . ?
C7 C6 1.404(3) . ?
C8 C10 1.472(3) 2_756 ?
C8 C9 1.424(3) . ?
C10 C9 1.429(3) . ?
C10 C11 1.392(2) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.535(4) . ?
C15 C14 1.530(2) . ?
C3 C2 1.489(2) . ?
C3 C12 1.380(3) . ?
C6 H1 0.9300 . ?
C6 C5 1.378(3) . ?
C5 C1 1.485(3) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C17 1.526(3) . ?
C11 H3 0.9300 . ?
C11 C12 1.405(2) . ?
C12 H4 0.9300 . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C13 1.536(4) . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C18 H15 0.9600 . ?
C18 H16 0.9600 . ?
C18 H17 0.9600 . ?
C18 C17 1.527(6) . ?
C17 H13 0.9700 . ?
C17 H14 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
C2 N1 C13 117.07(17) . . ?
C2 N1 C1 125.05(16) . . ?
C1 N1 C13 117.77(18) . . ?
C3 C4 C9 120.0(2) . . ?
C3 C4 C5 120.29(18) . . ?
C5 C4 C9 119.72(18) . . ?
C8 C7 H2 119.4 . . ?
C8 C7 C6 121.19(18) . . ?
C6 C7 H2 119.4 . . ?
C7 C8 C10 121.67(17) . 2_756 ?
C7 C8 C9 119.16(18) . . ?
C9 C8 C10 119.16(19) . 2_756 ?
C9 C10 C8 118.97(17) . 2_756 ?
C11 C10 C8 121.94(19) . 2_756 ?
C11 C10 C9 119.09(18) . . ?
H9 C15 H10 108.0 . . ?
C16 C15 H9 109.4 . . ?
C16 C15 H10 109.4 . . ?
C14 C15 H9 109.4 . . ?
C14 C15 H10 109.4 . . ?
C14 C15 C16 111.3(2) . . ?
C4 C3 C2 120.4(2) . . ?
C12 C3 C4 120.61(17) . . ?
C12 C3 C2 118.96(17) . . ?
O2 C2 N1 120.62(17) . . ?
O2 C2 C3 122.4(2) . . ?
N1 C2 C3 116.93(17) . . ?
C7 C6 H1 119.8 . . ?
C5 C6 C7 120.4(2) . . ?
C5 C6 H1 119.8 . . ?
C4 C9 C10 118.89(17) . . ?
C8 C9 C4 119.2(2) . . ?
C8 C9 C10 121.85(18) . . ?
C4 C5 C1 120.51(18) . . ?
C6 C5 C4 120.25(18) . . ?
C6 C5 C1 119.2(2) . . ?
C15 C16 H11 109.1 . . ?
C15 C16 H12 109.1 . . ?
H11 C16 H12 107.8 . . ?
C17 C16 C15 112.6(3) . . ?
C17 C16 H11 109.1 . . ?
C17 C16 H12 109.1 . . ?
C10 C11 H3 119.2 . . ?
C10 C11 C12 121.62(19) . . ?
C12 C11 H3 119.2 . . ?
C3 C12 C11 119.76(16) . . ?
C3 C12 H4 120.1 . . ?
C11 C12 H4 120.1 . . ?
C15 C14 H7 109.2 . . ?
C15 C14 H8 109.2 . . ?
C15 C14 C13 112.1(2) . . ?
H7 C14 H8 107.9 . . ?
C13 C14 H7 109.2 . . ?
C13 C14 H8 109.2 . . ?
N1 C13 C14 110.1(2) . . ?
N1 C13 H5 109.6 . . ?
N1 C13 H6 109.6 . . ?
C14 C13 H5 109.6 . . ?
C14 C13 H6 109.6 . . ?
H5 C13 H6 108.2 . . ?
O1 C1 N1 120.72(17) . . ?
O1 C1 C5 122.45(19) . . ?
N1 C1 C5 116.78(19) . . ?
H15 C18 H16 109.5 . . ?
H15 C18 H17 109.5 . . ?
H16 C18 H17 109.5 . . ?
C17 C18 H15 109.5 . . ?
C17 C18 H16 109.5 . . ?
C17 C18 H17 109.5 . . ?
C16 C17 C18 111.1(3) . . ?
C16 C17 H13 109.4 . . ?
C16 C17 H14 109.4 . . ?
C18 C17 H13 109.4 . . ?
C18 C17 H14 109.4 . . ?
H13 C17 H14 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
C4 C3 C2 O2 177.5(2) . . . . ?
C4 C3 C2 N1 -0.3(4) . . . . ?
C4 C3 C12 C11 -2.7(4) . . . . ?
C4 C5 C1 O1 -178.1(3) . . . . ?
C4 C5 C1 N1 -0.4(5) . . . . ?
C7 C8 C9 C4 0.0(4) . . . . ?
C7 C8 C9 C10 -178.80(19) . . . . ?
C7 C6 C5 C4 1.6(5) . . . . ?
C7 C6 C5 C1 -179.1(2) . . . . ?
C8 C7 C6 C5 -0.6(5) . . . . ?
C8 C10 C9 C4 179.70(15) 2_756 . . . ?
C8 C10 C9 C8 -1.5(5) 2_756 . . . ?
C8 C10 C11 C12 179.71(18) 2_756 . . . ?
C10 C8 C9 C4 -179.70(15) 2_756 . . . ?
C10 C8 C9 C10 1.5(5) 2_756 . . . ?
C10 C11 C12 C3 1.9(4) . . . . ?
C15 C16 C17 C18 178.2(3) . . . . ?
C15 C14 C13 N1 172.10(19) . . . . ?
C3 C4 C9 C8 -179.54(17) . . . . ?
C3 C4 C9 C10 -0.7(4) . . . . ?
C3 C4 C5 C6 178.7(2) . . . . ?
C3 C4 C5 C1 -0.5(5) . . . . ?
C2 N1 C13 C14 -85.5(3) . . . . ?
C2 N1 C1 O1 178.8(3) . . . . ?
C2 N1 C1 C5 1.1(5) . . . . ?
C2 C3 C12 C11 178.03(19) . . . . ?
C6 C7 C8 C10 179.5(2) . . . 2_756 ?
C6 C7 C8 C9 -0.2(5) . . . . ?
C6 C5 C1 O1 2.6(5) . . . . ?
C6 C5 C1 N1 -179.7(2) . . . . ?
C9 C4 C3 C2 -178.63(18) . . . . ?
C9 C4 C3 C12 2.1(4) . . . . ?
C9 C4 C5 C6 -1.7(5) . . . . ?
C9 C4 C5 C1 178.99(19) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C5 C4 C3 C2 0.9(4) . . . . ?
C5 C4 C3 C12 -178.4(2) . . . . ?
C5 C4 C9 C8 0.9(5) . . . . ?
C5 C4 C9 C10 179.77(16) . . . . ?
C16 C15 C14 C13 -179.7(2) . . . . ?
C11 C10 C9 C4 -0.1(4) . . . . ?
C11 C10 C9 C8 178.75(19) . . . . ?
C12 C3 C2 O2 -3.2(4) . . . . ?
C12 C3 C2 N1 179.01(19) . . . . ?
C14 C15 C16 C17 179.0(2) . . . . ?
C13 N1 C2 O2 -2.5(4) . . . . ?
C13 N1 C2 C3 175.3(2) . . . . ?
C13 N1 C1 O1 2.8(5) . . . . ?
C13 N1 C1 C5 -174.9(2) . . . . ?
C1 N1 C2 O2 -178.5(2) . . . . ?
C1 N1 C2 C3 -0.8(5) . . . . ?
C1 N1 C13 C14 90.8(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_C6_1_74GPa
_database_code_depnum_ccdc_archive 'CCDC 2412023'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C6_1_74GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.226 Why?  
RESPONSE: These data come from a high-pressure experiment and part of the 
reflections could not be collected due to the limited DAC opening angle and the 
measurement strategy.
;
_vrf_PLAT088_PDI_C6_1_74GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.75 Note   
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber. 
;
_vrf_PLAT340_PDI_C6_1_74GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03158 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_C6_1_74GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        259 Report
                5 -4  1,   5 -1  1,   5  0  1,   5  1  1,   5  2  1,   4  4  1, 
                2  5  1,   4  5  1,   3  7  1,   2  8  1,   1-10  2,   4 -7  2, 
                5 -4  2,   5 -3  2,   5 -2  2,   1 -1  2,   4 -1  2,   5 -1  2, 
                1  0  2,   4  0  2,   5  0  2,   1  1  2,   4  1  2,   5  1  2, 
                0  2  2,   1  2  2,   4  2  2,   5  2  2,   0  3  2,   3  3  2, 
                4  3  2,   3  4  2,   4  4  2,   2  5  2,   3  5  2,   4  5  2, 
                2  6  2,   3  6  2,   2  7  2,   3  7  2,   1  8  2,   2  8  2, 
                0  9  2,   1  9  2,  -1 10  2,   0 10  2,   1-10  3,   3 -9  3, 
                3 -8  3,   3 -7  3,   4 -7  3,   3 -6  3,   4 -6  3,   3 -5  3, 
                4 -5  3,   3 -4  3,   4 -4  3,   5 -4  3,   0 -3  3,   1 -3  3, 
                2 -3  3,   3 -3  3,   4 -3  3,   5 -3  3,   0 -2  3,   1 -2  3, 
                2 -2  3,   3 -2  3,   4 -2  3,   5 -2  3,  -1 -1  3,   1 -1  3, 
                2 -1  3,   3 -1  3,   4 -1  3,   5 -1  3,  -1  0  3,   1  0  3, 
                2  0  3,   3  0  3,   4  0  3,   5  0  3,  -1  1  3,   1  1  3, 
                2  1  3,   3  1  3,   4  1  3,   5  1  3,  -1  2  3,   0  2  3, 
                1  2  3,   2  2  3,   3  2  3,   4  2  3,  -1  3  3,   0  3  3, 
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-06-07
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   4.4771(8)
_cell_length_b                   8.5973(12)
_cell_length_c                   15.894(10)
_cell_angle_alpha                90.70(4)
_cell_angle_beta                 92.11(4)
_cell_angle_gamma                97.502(13)
_cell_volume                     606.0(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    888
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0700
_cell_measurement_theta_min      4.6000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.451
_exptl_absorpt_correction_T_min  0.328
_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    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 3 2 0.0672
-1 -12 1 0.1540
6 -2 -2 0.1352
1 12 -1 0.1177
-6 0 5 0.0677
0 0 -22 0.0180
6 0 -4 0.1218
0 0 22 0.0148

_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.038
_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)      0.398     0.453
         range of gasket transmission (min-max)           0.816     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 = 250.0 microns, radius = 250.0 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  0.0782
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 0.226
_diffrn_reflns_Laue_measured_fraction_max 0.210
_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       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            2964
_diffrn_reflns_point_group_measured_fraction_full 0.226
_diffrn_reflns_point_group_measured_fraction_max 0.210
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.406
_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 0.226
_diffrn_measured_fraction_theta_max 0.210
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00 -21.00   0.75   17.50    --  -29.94  77.00 150.00   48
  2  ω    -19.00  44.00   0.75   17.50    --  -29.94 -39.00-167.00   84
  3  ω    -89.00 -26.00   0.75   17.50    --  -29.94 135.00 123.00   84
  4  ω     13.00  40.00   0.75   17.50    --  -29.94-114.00-135.00   36
  5  ω    -44.00  19.00   0.75   17.50    --  -29.94  19.00-180.00   84
  6  ω    -31.00   0.50   0.75   17.50    --  -29.94   0.00   0.00   42
  7  ω     13.00  40.00   0.75   17.50    --  -29.94-114.00  45.00   36
  8  ω    -55.00   8.00   0.75   17.50    --  -29.94  67.00 -23.00   84
  9  ω    -19.00  44.00   0.75   17.50    --  -29.94 -39.00  12.00   84
 10  ω    -31.00   0.50   0.75   17.50    --   30.41   0.00-150.00   42
 11  ω    -31.00   0.50   0.75   17.50    --   30.41   0.00  30.00   42
 12  ω      8.00  32.00   0.75   17.50    --  -29.94 -99.00-150.00   32
 13  ω    -19.00   5.00   0.75   17.50    --  -29.94 -57.00  30.00   32
 14  ω    -19.00  14.00   0.75   17.50    --  -29.94 -19.00-150.00   44
 15  ω    -40.00 -13.00   0.75   17.50    --   30.41 114.00 135.00   36
 16  ω      1.75  49.00   0.75   17.50    --   30.41 -53.00  17.00   63
 17  ω    -16.00   8.00   0.75   17.50    --   30.41  67.00 157.00   32
 18  ω     20.00  56.00   0.75   17.50    --   30.41 -77.00-150.00   48
 19  ω     31.00  76.00   0.75   17.50    --   30.41-125.00  60.00   60
 20  ω     -5.00  19.00   0.75   17.50    --   30.41  57.00 -30.00   32
 21  ω    -44.00  19.00   0.75   17.50    --  -29.94  39.00 -12.00   84
 22  ω    -44.00  19.00   0.75   17.50    --  -29.94  19.00-180.00   84
 23  ω    -19.00  44.00   0.75   17.50    --  -29.94 -19.00-180.00   84
 24  ω    -19.00  44.00   0.75   17.50    --  -29.94 -39.00  12.00   84
 25  ω    -22.25  40.00   0.75   17.50    --  -29.94 -26.00   7.00   83
 26  ω    -26.25  36.00   0.75   17.50    --  -29.94 -13.00   3.00   83
 27  ω    -36.00  27.00   0.75   17.50    --  -29.94  13.00  -3.00   84
 28  ω    -40.00  23.00   0.75   17.50    --  -29.94  26.00  -7.00   84
 29  ω     -8.00  52.00   0.75   17.50    --  -29.94 -37.00-180.00   80
 30  ω    -49.00  14.00   0.75   17.50    --  -29.94  53.00 -17.00   84
;
_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 1.74(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                255
_reflns_number_total             526
_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         0.159
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         526
_refine_ls_number_restraints     374
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.0799
_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)+(0.0264P)²+5.3784P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1663
_refine_ls_wR_factor_ref         0.2181
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H4(0.026) H3(0.033) H6(0.045) H7(0.045) H13(0.045) H12(0.045)
 H8(0.054) H9(0.054) H2(0.041) H13A(0.045) H5(0.045) H11(0.052) H10(0.052)
 H1(0.038) H16(0.084) H17(0.084) H14(0.084)
 Fixed X: H4(0.7588) H3(0.39556) H6(0.786029) H7(1.10692) H13(1.072756)
 H12(1.013125) H8(0.721923) H9(1.036814) H2(-0.084896) H13A(1.266728)
 H5(1.156505) H11(0.634506) H10(0.546493) H1(0.27623) H16(0.877456)
 H17(0.677466) H14(0.577357)
 Fixed Y: H4(0.417751) H3(0.322081) H6(0.361094) H7(0.451028) H13(0.819723)
 H12(0.667223) H8(0.539001) H9(0.631159) H2(-0.225319) H13A(0.376679)
 H5(0.230838) H11(0.749967) H10(0.605307) H1(-0.131536) H16(0.866857)
 H17(0.920103) H14(0.762115)
 Fixed Z: H4(0.501806) H3(0.596352) H6(0.120131) H7(0.106784) H13(0.087372)
 H12(0.03083) H8(0.228308) H9(0.210279) H2(0.326016) H13A(0.238313)
 H5(0.179865) H11(0.155938) H10(0.095236) H1(0.232568) H16(-0.048318)
 H17(0.022792) H14(-0.026868)
;
_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 1.046(2) 0.4475(11) 0.369(2) 0.041(8) Uani 1 1 d D U . . .
O1 O 0.703(3) 0.0599(14) 0.179(2) 0.041(5) Uani 1 1 d D U . . .
N1 N 0.876(3) 0.2553(14) 0.2748(18) 0.029(5) Uani 1 1 d D U . . .
C2 C 0.869(3) 0.3324(19) 0.355(2) 0.028(5) Uani 1 1 d D U . . .
C12 C 0.621(3) 0.3306(17) 0.486(2) 0.022(4) Uani 1 1 d D U . . .
H4 H 0.758800 0.417751 0.501806 0.026 Uiso 1 1 calc R U . . .
C11 C 0.404(3) 0.2724(14) 0.544(3) 0.028(5) Uani 1 1 d D U . . .
H3 H 0.395560 0.322081 0.596352 0.033 Uiso 1 1 calc R U . . .
C14 C 0.959(3) 0.4215(15) 0.149(3) 0.038(6) Uani 1 1 d D U . . .
H6 H 0.786029 0.361094 0.120131 0.045 Uiso 1 1 calc R U . . .
H7 H 1.106920 0.451028 0.106784 0.045 Uiso 1 1 calc R U . . .
C17 C 0.916(4) 0.7462(18) 0.060(2) 0.038(11) Uani 1 1 d D U . . .
H13 H 1.072756 0.819723 0.087372 0.045 Uiso 1 1 calc R U . . .
H12 H 1.013125 0.667223 0.030830 0.045 Uiso 1 1 calc R U . . .
C4 C 0.436(3) 0.1268(15) 0.3842(16) 0.024(4) Uani 1 1 d D U . . .
C10 C 0.200(3) 0.1383(15) 0.522(2) 0.024(4) Uani 1 1 d D U . . .
C5 C 0.462(3) 0.0559(16) 0.3050(17) 0.027(4) Uani 1 1 d D U . . .
C15 C 0.861(3) 0.5684(15) 0.184(3) 0.045(9) Uani 1 1 d D U . . .
H8 H 0.721923 0.539001 0.228308 0.054 Uiso 1 1 calc R U . . .
H9 H 1.036814 0.631159 0.210279 0.054 Uiso 1 1 calc R U . . .
C7 C 0.050(4) -0.138(2) 0.342(2) 0.034(5) Uani 1 1 d D U . . .
H2 H -0.084896 -0.225319 0.326016 0.041 Uiso 1 1 calc R U . . .
C13 C 1.091(3) 0.3181(18) 0.210(2) 0.038(6) Uani 1 1 d D U . . .
H13A H 1.266728 0.376679 0.238313 0.045 Uiso 1 1 calc R U . . .
H5 H 1.156505 0.230838 0.179865 0.045 Uiso 1 1 calc R U . . .
C16 C 0.715(3) 0.6690(18) 0.124(2) 0.043(6) Uani 1 1 d D U . . .
H11 H 0.634506 0.749967 0.155938 0.052 Uiso 1 1 calc R U . . .
H10 H 0.546493 0.605307 0.095236 0.052 Uiso 1 1 calc R U . . .
C3 C 0.638(3) 0.2620(15) 0.4061(19) 0.022(4) Uani 1 1 d D U . . .
C9 C 0.224(3) 0.0662(16) 0.4432(18) 0.026(4) Uani 1 1 d D U . . .
C8 C 0.024(3) -0.0724(16) 0.423(2) 0.026(5) Uani 1 1 d D U . . .
C6 C 0.265(3) -0.0801(15) 0.284(2) 0.032(5) Uani 1 1 d D U . . .
H1 H 0.276230 -0.131536 0.232568 0.038 Uiso 1 1 calc R U . . .
C18 C 0.747(4) 0.831(2) -0.004(3) 0.056(9) Uani 1 1 d D U . . .
H16 H 0.877456 0.866857 -0.048318 0.084 Uiso 1 1 calc R U . . .
H17 H 0.677466 0.920103 0.022792 0.084 Uiso 1 1 calc R U . . .
H14 H 0.577357 0.762115 -0.026868 0.084 Uiso 1 1 calc R U . . .
C1 C 0.679(4) 0.118(2) 0.247(2) 0.024(5) Uani 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.20(2) . ?
O1 C1 1.21(3) . ?
N1 C2 1.43(3) . ?
N1 C13 1.49(2) . ?
N1 C1 1.43(2) . ?
C2 C3 1.414(17) . ?
C12 H4 0.9300 . ?
C12 C11 1.415(17) . ?
C12 C3 1.406(18) . ?
C11 H3 0.9300 . ?
C11 C10 1.405(15) . ?
C14 H6 0.9700 . ?
C14 H7 0.9700 . ?
C14 C15 1.50(2) . ?
C14 C13 1.48(2) . ?
C17 H13 0.9700 . ?
C17 H12 0.9700 . ?
C17 C16 1.49(2) . ?
C17 C18 1.49(2) . ?
C4 C5 1.406(17) . ?
C4 C3 1.410(15) . ?
C4 C9 1.414(16) . ?
C10 C9 1.410(18) . ?
C10 C8 1.42(3) 2_556 ?
C5 C6 1.398(16) . ?
C5 C1 1.423(17) . ?
C15 H8 0.9700 . ?
C15 H9 0.9700 . ?
C15 C16 1.49(2) . ?
C7 H2 0.9300 . ?
C7 C8 1.407(18) . ?
C7 C6 1.405(17) . ?
C13 H13A 0.9700 . ?
C13 H5 0.9700 . ?
C16 H11 0.9700 . ?
C16 H10 0.9700 . ?
C9 C8 1.421(15) . ?
C6 H1 0.9300 . ?
C18 H16 0.9600 . ?
C18 H17 0.9600 . ?
C18 H14 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 121.4(15) . . ?
C1 N1 C2 125.1(19) . . ?
C1 N1 C13 113.5(19) . . ?
O2 C2 N1 118(2) . . ?
O2 C2 C3 129(3) . . ?
C3 C2 N1 113.5(18) . . ?
C11 C12 H4 118.7 . . ?
C3 C12 H4 118.7 . . ?
C3 C12 C11 122.7(17) . . ?
C12 C11 H3 120.5 . . ?
C10 C11 C12 119(2) . . ?
C10 C11 H3 120.5 . . ?
H6 C14 H7 107.4 . . ?
C15 C14 H6 108.2 . . ?
C15 C14 H7 108.2 . . ?
C13 C14 H6 108.2 . . ?
C13 C14 H7 108.2 . . ?
C13 C14 C15 116(3) . . ?
H13 C17 H12 107.9 . . ?
C16 C17 H13 109.2 . . ?
C16 C17 H12 109.2 . . ?
C18 C17 H13 109.2 . . ?
C18 C17 H12 109.2 . . ?
C18 C17 C16 112.1(16) . . ?
C5 C4 C3 117.9(16) . . ?
C5 C4 C9 123.2(15) . . ?
C3 C4 C9 118.9(18) . . ?
C11 C10 C9 118.2(19) . . ?
C11 C10 C8 122(2) . 2_556 ?
C9 C10 C8 119.4(17) . 2_556 ?
C4 C5 C1 122.1(17) . . ?
C6 C5 C4 117.9(18) . . ?
C6 C5 C1 120(2) . . ?
C14 C15 H8 108.1 . . ?
C14 C15 H9 108.1 . . ?
H8 C15 H9 107.3 . . ?
C16 C15 C14 117(3) . . ?
C16 C15 H8 108.1 . . ?
C16 C15 H9 108.1 . . ?
C8 C7 H2 117.5 . . ?
C6 C7 H2 117.5 . . ?
C6 C7 C8 125(2) . . ?
N1 C13 H13A 108.9 . . ?
N1 C13 H5 108.9 . . ?
C14 C13 N1 113.4(14) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H5 108.9 . . ?
H13A C13 H5 107.7 . . ?
C17 C16 H11 108.5 . . ?
C17 C16 H10 108.5 . . ?
C15 C16 C17 115.2(15) . . ?
C15 C16 H11 108.5 . . ?
C15 C16 H10 108.5 . . ?
H11 C16 H10 107.5 . . ?
C12 C3 C2 116.4(18) . . ?
C12 C3 C4 118.3(17) . . ?
C4 C3 C2 125(2) . . ?
C4 C9 C8 119(2) . . ?
C10 C9 C4 122.7(16) . . ?
C10 C9 C8 117.9(18) . . ?
C7 C8 C10 121.3(19) . 2_556 ?
C7 C8 C9 116(2) . . ?
C9 C8 C10 123(2) . 2_556 ?
C5 C6 C7 119(2) . . ?
C5 C6 H1 120.7 . . ?
C7 C6 H1 120.7 . . ?
C17 C18 H16 109.5 . . ?
C17 C18 H17 109.5 . . ?
C17 C18 H14 109.5 . . ?
H16 C18 H17 109.5 . . ?
H16 C18 H14 109.5 . . ?
H17 C18 H14 109.5 . . ?
O1 C1 N1 121(2) . . ?
O1 C1 C5 123(2) . . ?
C5 C1 N1 116(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
O2 C2 C3 C12 -3(3) . . . . ?
O2 C2 C3 C4 179(2) . . . . ?
N1 C2 C3 C12 179.1(14) . . . . ?
N1 C2 C3 C4 2(2) . . . . ?
C2 N1 C13 C14 -94(2) . . . . ?
C2 N1 C1 O1 -179(2) . . . . ?
C2 N1 C1 C5 0(2) . . . . ?
C12 C11 C10 C9 1(2) . . . . ?
C12 C11 C10 C8 179.7(16) . . . 2_556 ?
C11 C12 C3 C2 -179.7(16) . . . . ?
C11 C12 C3 C4 -2(2) . . . . ?
C11 C10 C9 C4 -3(2) . . . . ?
C11 C10 C9 C8 177.8(15) . . . . ?
C14 C15 C16 C17 -67(2) . . . . ?
C4 C5 C6 C7 1(2) . . . . ?
C4 C5 C1 O1 -179.4(19) . . . . ?
C4 C5 C1 N1 2(2) . . . . ?
C4 C9 C8 C10 -178.3(17) . . . 2_556 ?
C4 C9 C8 C7 -1(2) . . . . ?
C10 C9 C8 C10 1(3) . . . 2_556 ?
C10 C9 C8 C7 178.1(14) . . . . ?
C5 C4 C3 C2 0(2) . . . . ?
C5 C4 C3 C12 -177.9(14) . . . . ?
C5 C4 C9 C10 -179.8(15) . . . . ?
C5 C4 C9 C8 0(2) . . . . ?
C15 C14 C13 N1 62(2) . . . . ?
C13 N1 C2 O2 -2(2) . . . . ?
C13 N1 C2 C3 176.2(14) . . . . ?
C13 N1 C1 O1 3(3) . . . . ?
C13 N1 C1 C5 -177.9(14) . . . . ?
C13 C14 C15 C16 -177.0(13) . . . . ?
C3 C12 C11 C10 2(2) . . . . ?
C3 C4 C5 C6 178.6(15) . . . . ?
C3 C4 C5 C1 -1(2) . . . . ?
C3 C4 C9 C10 2(2) . . . . ?
C3 C4 C9 C8 -178.3(15) . . . . ?
C9 C4 C5 C6 1(2) . . . . ?
C9 C4 C5 C1 -179.3(16) . . . . ?
C9 C4 C3 C2 177.6(16) . . . . ?
C9 C4 C3 C12 0(2) . . . . ?
C8 C10 C9 C4 178.4(16) 2_556 . . . ?
C8 C10 C9 C8 -1(2) 2_556 . . . ?
C8 C7 C6 C5 -3(3) . . . . ?
C6 C5 C1 O1 1(3) . . . . ?
C6 C5 C1 N1 -178.3(16) . . . . ?
C6 C7 C8 C10 -179.9(17) . . . 2_556 ?
C6 C7 C8 C9 3(2) . . . . ?
C18 C17 C16 C15 174.0(17) . . . . ?
C1 N1 C2 O2 -179.2(19) . . . . ?
C1 N1 C2 C3 -1(2) . . . . ?
C1 N1 C13 C14 83.6(19) . . . . ?
C1 C5 C6 C7 -179.2(17) . . . . ?

_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_C6_3_43GPa
_database_code_depnum_ccdc_archive 'CCDC 2412028'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C6_3_43GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.320 Why?  
RESPONSE: These data come from a high-pressure experiment and part of the 
reflections could not be collected due to the limited DAC opening angle and the 
measurement strategy.
;
_vrf_PLAT088_PDI_C6_3_43GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.99 Note   
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber. 
;
_vrf_PLAT911_PDI_C6_3_43GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        903 Report
               -1  1  0,  -5  2  0,  -1  2  0,  -2  3  0,  -1  3  0,  -5  4  0, 
               -4  4  0,  -3  4  0,  -2  4  0,  -4  5  0,  -3  5  0,  -2  5  0, 
               -4  6  0,  -3  6  0,  -2  6  0,  -4  7  0,  -3  7  0,  -3  8  0, 
               -3  9  0,   2 -9  1,   3 -9  1,   3 -8  1,   3 -7  1,   4 -7  1, 
                2 -6  1,   3 -6  1,   4 -6  1,   2 -5  1,   3 -5  1,   4 -5  1, 
               -1 -4  1,   2 -4  1,   3 -4  1,   2 -3  1,   1 -2  1,   5 -2  1, 
                1 -1  1,  -1  1  1,   0  1  1,  -1  2  1,  -2  3  1,  -5  4  1, 
               -4  4  1,  -3  4  1,  -2  4  1,  -4  5  1,  -3  5  1,  -2  5  1, 
               -4  6  1,  -3  6  1,  -4  7  1,  -3  7  1,  -3  8  1,  -2  8  1, 
               -3  9  1,  -1  9  1,   3 -9  2,   3 -8  2,   3 -7  2,   4 -7  2, 
                2 -6  2,   3 -6  2,   4 -6  2,   3 -5  2,   4 -5  2,   2 -4  2, 
                3 -4  2,   2 -3  2,   3 -3  2,   1 -2  2,   2 -2  2,   5 -2  2, 
                0 -1  2,   1 -1  2,   1  0  2,  -1  1  2,   0  1  2,   1  1  2, 
               -1  2  2,   0  2  2,  -1  3  2,  -5  4  2,  -4  4  2,  -3  4  2, 
               -2  4  2,  -4  5  2,  -3  5  2,  -4  6  2,  -3  6  2,  -1  6  2, 
               -4  7  2,  -3  7  2,  -3  8  2,  -3  9  2,  -1  9  2,   3 -8  3, 
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-06-07
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   4.3382(2)
_cell_length_b                   8.5989(3)
_cell_length_c                   15.5271(14)
_cell_angle_alpha                90.778(6)
_cell_angle_beta                 93.255(6)
_cell_angle_gamma                97.299(3)
_cell_volume                     573.47(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2160
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3770
_cell_measurement_theta_min      3.2740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38214
_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    1.618
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_preparation       'mounted in a diamond-anvil cell'
_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.066
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.320
_diffrn_reflns_Laue_measured_fraction_max 0.201
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6044
_diffrn_reflns_point_group_measured_fraction_full 0.320
_diffrn_reflns_point_group_measured_fraction_max 0.201
_diffrn_reflns_theta_full        17.160
_diffrn_reflns_theta_max         24.398
_diffrn_reflns_theta_min         1.869
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.320
_diffrn_measured_fraction_theta_max 0.201
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     18.00  97.00   0.20    0.50  57.05   0.00-134.76    --   395
  2  φ     18.00  97.00   0.20    0.50  57.05   0.00-134.76    --   395
  3  φ     18.00  97.00   0.20    0.50  57.05   0.00-134.76    --   395
  4  φ     18.00  97.00   0.20    0.50  57.05   0.00-134.76    --   395
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.49173
_diffrn_source                   synchrotron
_diffrn_special_details          
'Data were collected at room temperature and pressure of 3.43(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                952
_reflns_number_total             1144
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.101
_refine_diff_density_min         -0.091
_refine_diff_density_rms         0.024
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.112
_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)+(0.0989P)²+0.0098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1364
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H4(0.038) H3(0.048) H7(0.05) H8(0.05) H16(0.051) H15(0.051)
 H9(0.05) H10(0.05) H2(0.045) H5(0.045) H6(0.045) H12(0.06) H11(0.06) H1(0.042)
 H18(0.072) H19(0.072) H17(0.072)
 Fixed X: H4(0.757874) H3(0.395189) H7(0.785674) H8(1.114621) H16(1.092155)
 H15(1.044738) H9(0.738497) H10(1.064851) H2(-0.070768) H5(1.191979)
 H6(1.29635) H12(0.635854) H11(0.555608) H1(0.283879) H18(0.894797)
 H19(0.640121) H17(0.611566)
 Fixed Y: H4(0.430456) H3(0.33103) H7(0.361426) H8(0.45019) H16(0.831009)
 H15(0.679715) H9(0.540312) H10(0.629979) H2(-0.239591) H5(0.232131)
 H6(0.378473) H12(0.750774) H11(0.607901) H1(-0.132087) H18(0.896211)
 H19(0.911652) H17(0.764327)
 Fixed Z: H4(0.498564) H3(0.597423) H7(0.116629) H8(0.10019) H16(0.08769)
 H15(0.028312) H9(0.230031) H10(0.211878) H2(0.326071) H5(0.17775) H6(0.238876)
 H12(0.154279) H11(0.089982) H1(0.226552) H18(-0.046731) H19(0.019476) H17(-
 0.042427)
;
_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 1.0596(2) 0.45219(12) 0.36643(19) 0.0447(18) Uani 1 1 d . . . . .
O1 O 0.7174(3) 0.05865(14) 0.1732(3) 0.042(2) Uani 1 1 d . . . . .
N1 N 0.8930(3) 0.25339(14) 0.2719(2) 0.0313(19) Uani 1 1 d . . . . .
C2 C 0.8816(3) 0.33137(17) 0.3478(3) 0.035(2) Uani 1 1 d . . . . .
C12 C 0.6254(3) 0.33871(17) 0.4847(3) 0.032(2) Uani 1 1 d . . . . .
H4 H 0.757874 0.430456 0.498564 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4056(3) 0.27981(15) 0.5447(3) 0.040(2) Uani 1 1 d . . . . .
H3 H 0.395189 0.331030 0.597423 0.048 Uiso 1 1 calc R U . . .
C14 C 0.9702(3) 0.42110(15) 0.1444(3) 0.042(2) Uani 1 1 d . . . . .
H7 H 0.785674 0.361426 0.116629 0.050 Uiso 1 1 calc R U . . .
H8 H 1.114621 0.450190 0.100190 0.050 Uiso 1 1 calc R U . . .
C17 C 0.9370(4) 0.75572(17) 0.0572(3) 0.043(2) Uani 1 1 d . . . . .
H16 H 1.092155 0.831009 0.087690 0.051 Uiso 1 1 calc R U . . .
H15 H 1.044738 0.679715 0.028312 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4460(3) 0.12663(15) 0.3830(3) 0.028(2) Uani 1 1 d . . . . .
C10 C 0.2045(3) 0.14192(15) 0.5222(3) 0.033(2) Uani 1 1 d . . . . .
C5 C 0.4683(3) 0.05321(16) 0.3060(3) 0.037(2) Uani 1 1 d . . . . .
C15 C 0.8795(4) 0.56955(15) 0.1850(3) 0.041(2) Uani 1 1 d . . . . .
H9 H 0.738497 0.540312 0.230031 0.050 Uiso 1 1 calc R U . . .
H10 H 1.064851 0.629979 0.211878 0.050 Uiso 1 1 calc R U . . .
C7 C 0.0555(4) -0.14610(17) 0.3403(3) 0.038(2) Uani 1 1 d . . . . .
H2 H -0.070768 -0.239591 0.326071 0.045 Uiso 1 1 calc R U . . .
C13 C 1.1183(3) 0.31792(16) 0.2084(3) 0.037(2) Uani 1 1 d . . . . .
H5 H 1.191979 0.232131 0.177750 0.045 Uiso 1 1 calc R U . . .
H6 H 1.296350 0.378473 0.238876 0.045 Uiso 1 1 calc R U . . .
C16 C 0.7255(4) 0.67228(18) 0.1218(3) 0.050(2) Uani 1 1 d . . . . .
H12 H 0.635854 0.750774 0.154279 0.060 Uiso 1 1 calc R U . . .
H11 H 0.555608 0.607901 0.089982 0.060 Uiso 1 1 calc R U . . .
C3 C 0.6471(3) 0.26692(16) 0.4098(3) 0.035(2) Uani 1 1 d . . . . .
C9 C 0.2235(3) 0.06531(15) 0.4440(3) 0.031(2) Uani 1 1 d . . . . .
C8 C 0.0246(3) -0.07650(16) 0.4162(3) 0.035(2) Uani 1 1 d . . . . .
C6 C 0.2725(3) -0.08413(15) 0.2801(3) 0.035(2) Uani 1 1 d . . . . .
H1 H 0.283879 -0.132087 0.226552 0.042 Uiso 1 1 calc R U . . .
C18 C 0.7542(4) 0.83963(19) -0.0092(3) 0.048(3) Uani 1 1 d . . . . .
H18 H 0.894797 0.896211 -0.046731 0.072 Uiso 1 1 calc R U . . .
H19 H 0.640121 0.911652 0.019476 0.072 Uiso 1 1 calc R U . . .
H17 H 0.611566 0.764327 -0.042427 0.072 Uiso 1 1 calc R U . . .
C1 C 0.6958(4) 0.11678(19) 0.2422(4) 0.034(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.234(2) . ?
O1 C1 1.189(7) . ?
N1 C2 1.355(5) . ?
N1 C13 1.490(3) . ?
N1 C1 1.418(3) . ?
C2 C3 1.500(4) . ?
C12 H4 0.9300 . ?
C12 C11 1.423(4) . ?
C12 C3 1.323(6) . ?
C11 H3 0.9300 . ?
C11 C10 1.407(3) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C15 1.521(4) . ?
C14 C13 1.511(4) . ?
C17 H16 0.9700 . ?
C17 H15 0.9700 . ?
C17 C16 1.523(4) . ?
C17 C18 1.512(5) . ?
C4 C5 1.358(6) . ?
C4 C3 1.438(3) . ?
C4 C9 1.448(4) . ?
C10 C9 1.384(6) . ?
C10 C8 1.484(4) 2_556 ?
C5 C6 1.404(3) . ?
C5 C1 1.498(4) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.513(4) . ?
C7 H2 0.9300 . ?
C7 C8 1.335(6) . ?
C7 C6 1.425(4) . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C16 H12 0.9700 . ?
C16 H11 0.9700 . ?
C9 C8 1.447(3) . ?
C6 H1 0.9300 . ?
C18 H18 0.9600 . ?
C18 H19 0.9600 . ?
C18 H17 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 119.23(16) . . ?
C2 N1 C1 126.6(2) . . ?
C1 N1 C13 114.1(3) . . ?
O2 C2 N1 121.4(3) . . ?
O2 C2 C3 120.2(3) . . ?
N1 C2 C3 118.43(17) . . ?
C11 C12 H4 119.0 . . ?
C3 C12 H4 119.0 . . ?
C3 C12 C11 122.00(19) . . ?
C12 C11 H3 120.9 . . ?
C10 C11 C12 118.2(4) . . ?
C10 C11 H3 120.9 . . ?
H7 C14 H8 107.7 . . ?
C15 C14 H7 108.9 . . ?
C15 C14 H8 108.9 . . ?
C13 C14 H7 108.9 . . ?
C13 C14 H8 108.9 . . ?
C13 C14 C15 113.6(3) . . ?
H16 C17 H15 108.0 . . ?
C16 C17 H16 109.3 . . ?
C16 C17 H15 109.3 . . ?
C18 C17 H16 109.3 . . ?
C18 C17 H15 109.3 . . ?
C18 C17 C16 111.42(15) . . ?
C5 C4 C3 122.2(2) . . ?
C5 C4 C9 121.78(19) . . ?
C3 C4 C9 116.0(3) . . ?
C11 C10 C8 119.5(4) . 2_556 ?
C9 C10 C11 120.6(2) . . ?
C9 C10 C8 119.89(19) . 2_556 ?
C4 C5 C6 122.1(2) . . ?
C4 C5 C1 122.1(2) . . ?
C6 C5 C1 115.8(3) . . ?
C14 C15 H9 108.7 . . ?
C14 C15 H10 108.7 . . ?
H9 C15 H10 107.6 . . ?
C16 C15 C14 114.0(3) . . ?
C16 C15 H9 108.7 . . ?
C16 C15 H10 108.7 . . ?
C8 C7 H2 118.4 . . ?
C8 C7 C6 123.20(18) . . ?
C6 C7 H2 118.4 . . ?
N1 C13 C14 111.27(13) . . ?
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 . . ?
C17 C16 H12 108.4 . . ?
C17 C16 H11 108.4 . . ?
C15 C16 C17 115.65(14) . . ?
C15 C16 H12 108.4 . . ?
C15 C16 H11 108.4 . . ?
H12 C16 H11 107.4 . . ?
C12 C3 C2 120.90(18) . . ?
C12 C3 C4 122.3(2) . . ?
C4 C3 C2 116.8(3) . . ?
C10 C9 C4 120.88(18) . . ?
C10 C9 C8 123.9(3) . . ?
C8 C9 C4 115.2(4) . . ?
C7 C8 C10 122.53(19) . 2_556 ?
C7 C8 C9 121.2(3) . . ?
C9 C8 C10 116.2(4) . 2_556 ?
C5 C6 C7 116.4(3) . . ?
C5 C6 H1 121.8 . . ?
C7 C6 H1 121.8 . . ?
C17 C18 H18 109.5 . . ?
C17 C18 H19 109.5 . . ?
C17 C18 H17 109.5 . . ?
H18 C18 H19 109.5 . . ?
H18 C18 H17 109.5 . . ?
H19 C18 H17 109.5 . . ?
O1 C1 N1 121.9(3) . . ?
O1 C1 C5 124.3(2) . . ?
N1 C1 C5 113.8(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
O2 C2 C3 C12 0.6(4) . . . . ?
O2 C2 C3 C4 179.38(18) . . . . ?
N1 C2 C3 C12 -179.8(2) . . . . ?
N1 C2 C3 C4 -1.0(3) . . . . ?
C2 N1 C13 C14 -93.0(3) . . . . ?
C2 N1 C1 O1 177.8(3) . . . . ?
C2 N1 C1 C5 -3.5(4) . . . . ?
C12 C11 C10 C9 0.7(4) . . . . ?
C12 C11 C10 C8 179.26(18) . . . 2_556 ?
C11 C12 C3 C2 -179.83(16) . . . . ?
C11 C12 C3 C4 1.4(4) . . . . ?
C11 C10 C9 C4 -1.2(4) . . . . ?
C11 C10 C9 C8 -179.81(17) . . . . ?
C14 C15 C16 C17 -70.4(3) . . . . ?
C4 C5 C6 C7 -2.2(3) . . . . ?
C4 C5 C1 O1 -177.9(3) . . . . ?
C4 C5 C1 N1 3.4(4) . . . . ?
C4 C9 C8 C10 179.77(15) . . . 2_556 ?
C4 C9 C8 C7 2.0(4) . . . . ?
C10 C9 C8 C10 -1.6(4) . . . 2_556 ?
C10 C9 C8 C7 -179.4(2) . . . . ?
C5 C4 C3 C2 1.1(4) . . . . ?
C5 C4 C3 C12 179.9(2) . . . . ?
C5 C4 C9 C10 180.0(2) . . . . ?
C5 C4 C9 C8 -1.3(4) . . . . ?
C15 C14 C13 N1 65.6(2) . . . . ?
C13 N1 C2 O2 -2.0(3) . . . . ?
C13 N1 C2 C3 178.33(15) . . . . ?
C13 N1 C1 O1 1.7(4) . . . . ?
C13 N1 C1 C5 -179.57(17) . . . . ?
C13 C14 C15 C16 -178.91(10) . . . . ?
C3 C12 C11 C10 -0.8(4) . . . . ?
C3 C4 C5 C6 179.72(18) . . . . ?
C3 C4 C5 C1 -2.4(4) . . . . ?
C3 C4 C9 C10 1.7(4) . . . . ?
C3 C4 C9 C8 -179.59(17) . . . . ?
C9 C4 C5 C6 1.6(4) . . . . ?
C9 C4 C5 C1 179.41(19) . . . . ?
C9 C4 C3 C2 179.37(16) . . . . ?
C9 C4 C3 C12 -1.8(4) . . . . ?
C8 C10 C9 C4 -179.79(16) 2_556 . . . ?
C8 C10 C9 C8 1.6(5) 2_556 . . . ?
C8 C7 C6 C5 2.9(4) . . . . ?
C6 C5 C1 O1 0.1(5) . . . . ?
C6 C5 C1 N1 -178.65(17) . . . . ?
C6 C7 C8 C10 179.46(17) . . . 2_556 ?
C6 C7 C8 C9 -2.9(5) . . . . ?
C18 C17 C16 C15 173.4(3) . . . . ?
C1 N1 C2 O2 -178.0(2) . . . . ?
C1 N1 C2 C3 2.4(4) . . . . ?
C1 N1 C13 C14 83.4(3) . . . . ?
C1 C5 C6 C7 179.8(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
;
####################################################################### 
# 
# 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_C6_2_74GPa
_database_code_depnum_ccdc_archive 'CCDC 2412027'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C6_2_74GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.316 Why?  
RESPONSE: These data come from a high-pressure experiment and part of the 
reflections could not be collected due to the limited DAC opening angle and the 
measurement strategy.
;
_vrf_PLAT088_PDI_C6_2_74GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.06 Note   
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber. 
;
_vrf_PLAT911_PDI_C6_2_74GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        914 Report
               -1  1  0,  -1  2  0,  -3  3  0,  -2  3  0,  -5  4  0,  -4  4  0, 
               -3  4  0,  -2  4  0,  -4  5  0,  -3  5  0,  -2  5  0,  -4  6  0, 
               -3  6  0,  -4  7  0,  -3  7  0,  -3  8  0,  -3  9  0,   3 -9  1, 
                3 -8  1,   2 -7  1,   3 -7  1,   4 -7  1,   3 -6  1,   4 -6  1, 
                3 -5  1,   4 -5  1,  -1 -4  1,   2 -4  1,   3 -4  1,   4 -4  1, 
                5 -4  1,   2 -3  1,   1 -2  1,  -2 -1  1,   1 -1  1,   4 -1  1, 
               -1  1  1,   0  1  1,  -1  2  1,  -5  3  1,  -4  3  1,  -2  3  1, 
               -5  4  1,  -4  4  1,  -3  4  1,  -2  4  1,  -4  5  1,  -3  5  1, 
               -4  6  1,  -3  6  1,  -4  7  1,  -3  7  1,  -3  8  1,  -3  9  1, 
                3 -9  2,   3 -8  2,   3 -7  2,   4 -7  2,   3 -6  2,   4 -6  2, 
                3 -5  2,   4 -5  2,   3 -4  2,   2 -3  2,   1 -2  2,   2 -2  2, 
                0 -1  2,   1 -1  2,   4 -1  2,  -3  0  2,   1  0  2,   3  0  2, 
               -1  1  2,   0  1  2,   1  1  2,  -1  2  2,   0  2  2,  -5  3  2, 
               -2  3  2,  -1  3  2,   4  3  2,  -5  4  2,  -4  4  2,  -3  4  2, 
               -4  5  2,  -3  5  2,  -4  6  2,  -3  6  2,  -4  7  2,  -3  7  2, 
               -2  7  2,  -3  8  2,  -3  9  2,   2 -9  3,   3 -8  3,   3 -7  3, 
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-06-07
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   4.37850(10)
_cell_length_b                   8.5972(2)
_cell_length_c                   15.7128(8)
_cell_angle_alpha                90.904(4)
_cell_angle_beta                 92.733(4)
_cell_angle_gamma                97.328(2)
_cell_volume                     585.83(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2250
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2960
_cell_measurement_theta_min      1.8620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.054
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74096
_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    1.583
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_preparation       'mounted in a diamond-anvil cell'
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.067
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.316
_diffrn_reflns_Laue_measured_fraction_max 0.197
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5996
_diffrn_reflns_point_group_measured_fraction_full 0.316
_diffrn_reflns_point_group_measured_fraction_max 0.197
_diffrn_reflns_theta_full        17.160
_diffrn_reflns_theta_max         24.487
_diffrn_reflns_theta_min         1.863
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_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  φ     19.00  97.00   0.20    0.50  57.05   0.00-134.76    --   390
  2  φ     19.00  97.00   0.20    0.50  57.05   0.00-134.76    --   390
  3  φ     19.00  97.00   0.20    0.50  57.05   0.00-134.76    --   390
  4  φ     19.00  97.00   0.20    0.50  57.05   0.00-134.76    --   390
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.49173
_diffrn_source                   synchrotron
_diffrn_special_details          
'Data were collected at room temperature and pressure of 2.74(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                997
_reflns_number_total             1158
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.097
_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)+(0.1098P)²+0.0098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1445
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H4(0.034) H3(0.041) H7(0.048) H8(0.048) H14(0.052) H13(0.052)
 H9(0.049) H10(0.049) H2(0.047) H5(0.05) H6(0.05) H12(0.059) H11(0.059)
 H1(0.045) H16(0.082) H17(0.082) H15(0.082)
 Fixed X: H4(0.757937) H3(0.396407) H7(0.782973) H8(1.109429) H14(1.088145)
 H13(1.0348) H9(0.732451) H10(1.055993) H2(-0.075762) H5(1.18722) H6(1.283733)
 H12(0.632143) H11(0.552552) H1(0.280643) H16(0.893177) H17(0.652883)
 H15(0.602995)
 Fixed Y: H4(0.428341) H3(0.328443) H7(0.360068) H8(0.448853) H14(0.826732)
 H13(0.674952) H9(0.540982) H10(0.630756) H2(-0.236757) H5(0.232943)
 H6(0.380558) H12(0.750988) H11(0.606228) H1(-0.129822) H16(0.887729)
 H17(0.914103) H15(0.763105)
 Fixed Z: H4(0.499645) H3(0.596845) H7(0.118557) H8(0.102056) H14(0.08676)
 H13(0.028378) H9(0.230176) H10(0.21175) H2(0.326052) H5(0.180649) H6(0.240539)
 H12(0.153568) H11(0.091295) H1(0.22886) H16(-0.046669) H17(0.02125) H15(-
 0.037567)
;
_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 1.0546(2) 0.45147(12) 0.36720(19) 0.0421(16) Uani 1 1 d . . . . .
O1 O 0.7105(3) 0.06020(14) 0.1751(3) 0.041(2) Uani 1 1 d . . . . .
N1 N 0.8863(3) 0.25408(14) 0.2723(2) 0.0282(18) Uani 1 1 d . . . . .
C2 C 0.8773(3) 0.33130(16) 0.3485(3) 0.036(2) Uani 1 1 d . . . . .
C12 C 0.6249(3) 0.33752(15) 0.4855(3) 0.029(2) Uani 1 1 d . . . . .
H4 H 0.757937 0.428341 0.499645 0.034 Uiso 1 1 calc R U . . .
C11 C 0.4063(3) 0.27800(14) 0.5444(2) 0.034(2) Uani 1 1 d . . . . .
H3 H 0.396407 0.328443 0.596845 0.041 Uiso 1 1 calc R U . . .
C14 C 0.9647(3) 0.42043(14) 0.1458(3) 0.040(2) Uani 1 1 d . . . . .
H7 H 0.782973 0.360068 0.118557 0.048 Uiso 1 1 calc R U . . .
H8 H 1.109429 0.448853 0.102056 0.048 Uiso 1 1 calc R U . . .
C17 C 0.9316(3) 0.75241(17) 0.0573(3) 0.044(2) Uani 1 1 d . . . . .
H14 H 1.088145 0.826732 0.086760 0.052 Uiso 1 1 calc R U . . .
H13 H 1.034800 0.674952 0.028378 0.052 Uiso 1 1 calc R U . . .
C4 C 0.4435(3) 0.12699(15) 0.3839(3) 0.027(2) Uani 1 1 d . . . . .
C10 C 0.2046(3) 0.14105(14) 0.5221(3) 0.030(2) Uani 1 1 d . . . . .
C5 C 0.4642(3) 0.05424(15) 0.3071(3) 0.032(2) Uani 1 1 d . . . . .
C15 C 0.8732(3) 0.56962(15) 0.1855(3) 0.041(2) Uani 1 1 d . . . . .
H9 H 0.732451 0.540982 0.230176 0.049 Uiso 1 1 calc R U . . .
H10 H 1.055993 0.630756 0.211750 0.049 Uiso 1 1 calc R U . . .
C7 C 0.0521(3) -0.14449(17) 0.3408(3) 0.039(2) Uani 1 1 d . . . . .
H2 H -0.075762 -0.236757 0.326052 0.047 Uiso 1 1 calc R U . . .
C13 C 1.1102(3) 0.31860(15) 0.2103(3) 0.041(2) Uani 1 1 d . . . . .
H5 H 1.187220 0.232943 0.180649 0.050 Uiso 1 1 calc R U . . .
H6 H 1.283733 0.380558 0.240539 0.050 Uiso 1 1 calc R U . . .
C16 C 0.7207(4) 0.67132(18) 0.1220(3) 0.049(2) Uani 1 1 d . . . . .
H12 H 0.632143 0.750988 0.153568 0.059 Uiso 1 1 calc R U . . .
H11 H 0.552552 0.606228 0.091295 0.059 Uiso 1 1 calc R U . . .
C3 C 0.6446(3) 0.26634(16) 0.4099(3) 0.032(2) Uani 1 1 d . . . . .
C9 C 0.2221(3) 0.06541(15) 0.4441(3) 0.029(2) Uani 1 1 d . . . . .
C8 C 0.0236(3) -0.07579(15) 0.4171(3) 0.029(2) Uani 1 1 d . . . . .
C6 C 0.2689(3) -0.08213(15) 0.2819(3) 0.038(2) Uani 1 1 d . . . . .
H1 H 0.280643 -0.129822 0.228860 0.045 Uiso 1 1 calc R U . . .
C18 C 0.7542(4) 0.83695(18) -0.0072(3) 0.054(3) Uani 1 1 d . . . . .
H16 H 0.893177 0.887729 -0.046669 0.082 Uiso 1 1 calc R U . . .
H17 H 0.652883 0.914103 0.021250 0.082 Uiso 1 1 calc R U . . .
H15 H 0.602995 0.763105 -0.037567 0.082 Uiso 1 1 calc R U . . .
C1 C 0.6910(4) 0.11805(18) 0.2448(3) 0.030(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.233(2) . ?
O1 C1 1.207(7) . ?
N1 C2 1.365(5) . ?
N1 C13 1.479(3) . ?
N1 C1 1.407(3) . ?
C2 C3 1.499(4) . ?
C12 H4 0.9300 . ?
C12 C11 1.418(4) . ?
C12 C3 1.338(6) . ?
C11 H3 0.9300 . ?
C11 C10 1.408(2) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C15 1.525(3) . ?
C14 C13 1.519(4) . ?
C17 H14 0.9700 . ?
C17 H13 0.9700 . ?
C17 C16 1.523(4) . ?
C17 C18 1.501(4) . ?
C4 C5 1.363(6) . ?
C4 C3 1.435(3) . ?
C4 C9 1.445(4) . ?
C10 C9 1.388(6) . ?
C10 C8 1.480(4) 2_556 ?
C5 C6 1.400(3) . ?
C5 C1 1.489(4) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.523(4) . ?
C7 H2 0.9300 . ?
C7 C8 1.346(6) . ?
C7 C6 1.419(4) . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C16 H12 0.9700 . ?
C16 H11 0.9700 . ?
C9 C8 1.445(3) . ?
C6 H1 0.9300 . ?
C18 H16 0.9600 . ?
C18 H17 0.9600 . ?
C18 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
C2 N1 C13 118.90(15) . . ?
C2 N1 C1 125.6(3) . . ?
C1 N1 C13 115.4(3) . . ?
O2 C2 N1 121.5(3) . . ?
O2 C2 C3 120.2(4) . . ?
N1 C2 C3 118.26(17) . . ?
C11 C12 H4 119.2 . . ?
C3 C12 H4 119.2 . . ?
C3 C12 C11 121.70(18) . . ?
C12 C11 H3 120.7 . . ?
C10 C11 C12 118.7(3) . . ?
C10 C11 H3 120.7 . . ?
H7 C14 H8 107.8 . . ?
C15 C14 H7 109.0 . . ?
C15 C14 H8 109.0 . . ?
C13 C14 H7 109.0 . . ?
C13 C14 H8 109.0 . . ?
C13 C14 C15 113.0(3) . . ?
H14 C17 H13 108.0 . . ?
C16 C17 H14 109.3 . . ?
C16 C17 H13 109.3 . . ?
C18 C17 H14 109.3 . . ?
C18 C17 H13 109.3 . . ?
C18 C17 C16 111.39(15) . . ?
C5 C4 C3 121.8(2) . . ?
C5 C4 C9 121.54(19) . . ?
C3 C4 C9 116.6(4) . . ?
C11 C10 C8 119.7(3) . 2_556 ?
C9 C10 C11 120.5(2) . . ?
C9 C10 C8 119.85(18) . 2_556 ?
C4 C5 C6 121.8(2) . . ?
C4 C5 C1 121.62(19) . . ?
C6 C5 C1 116.6(3) . . ?
C14 C15 H9 108.8 . . ?
C14 C15 H10 108.8 . . ?
H9 C15 H10 107.7 . . ?
C16 C15 C14 113.7(3) . . ?
C16 C15 H9 108.8 . . ?
C16 C15 H10 108.8 . . ?
C8 C7 H2 118.6 . . ?
C8 C7 C6 122.81(18) . . ?
C6 C7 H2 118.6 . . ?
N1 C13 C14 111.53(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 . . ?
C17 C16 H12 108.4 . . ?
C17 C16 H11 108.4 . . ?
C15 C16 C17 115.56(14) . . ?
C15 C16 H12 108.4 . . ?
C15 C16 H11 108.4 . . ?
H12 C16 H11 107.5 . . ?
C12 C3 C2 120.81(18) . . ?
C12 C3 C4 121.8(2) . . ?
C4 C3 C2 117.4(3) . . ?
C4 C9 C8 115.8(4) . . ?
C10 C9 C4 120.72(18) . . ?
C10 C9 C8 123.5(3) . . ?
C7 C8 C10 122.47(18) . 2_556 ?
C7 C8 C9 120.8(3) . . ?
C9 C8 C10 116.7(4) . 2_556 ?
C5 C6 C7 117.2(3) . . ?
C5 C6 H1 121.4 . . ?
C7 C6 H1 121.4 . . ?
C17 C18 H16 109.5 . . ?
C17 C18 H17 109.5 . . ?
C17 C18 H15 109.5 . . ?
H16 C18 H17 109.5 . . ?
H16 C18 H15 109.5 . . ?
H17 C18 H15 109.5 . . ?
O1 C1 N1 121.0(3) . . ?
O1 C1 C5 123.8(2) . . ?
N1 C1 C5 115.2(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
O2 C2 C3 C12 0.2(4) . . . . ?
O2 C2 C3 C4 179.45(17) . . . . ?
N1 C2 C3 C12 -179.8(2) . . . . ?
N1 C2 C3 C4 -0.5(3) . . . . ?
C2 N1 C13 C14 -95.2(3) . . . . ?
C2 N1 C1 O1 177.9(3) . . . . ?
C2 N1 C1 C5 -1.8(4) . . . . ?
C12 C11 C10 C9 0.6(4) . . . . ?
C12 C11 C10 C8 179.42(17) . . . 2_556 ?
C11 C12 C3 C2 179.99(15) . . . . ?
C11 C12 C3 C4 0.7(4) . . . . ?
C11 C10 C9 C4 -1.0(4) . . . . ?
C11 C10 C9 C8 179.75(16) . . . . ?
C14 C15 C16 C17 -69.8(3) . . . . ?
C4 C5 C6 C7 -1.6(3) . . . . ?
C4 C5 C1 O1 -177.6(3) . . . . ?
C4 C5 C1 N1 2.1(4) . . . . ?
C4 C9 C8 C10 179.87(14) . . . 2_556 ?
C4 C9 C8 C7 1.0(4) . . . . ?
C10 C9 C8 C10 -0.9(4) . . . 2_556 ?
C10 C9 C8 C7 -179.7(2) . . . . ?
C5 C4 C3 C2 0.9(4) . . . . ?
C5 C4 C3 C12 -179.8(2) . . . . ?
C5 C4 C9 C10 179.93(19) . . . . ?
C5 C4 C9 C8 -0.8(4) . . . . ?
C15 C14 C13 N1 66.2(2) . . . . ?
C13 N1 C2 O2 -1.3(3) . . . . ?
C13 N1 C2 C3 178.71(13) . . . . ?
C13 N1 C1 O1 0.2(4) . . . . ?
C13 N1 C1 C5 -179.52(16) . . . . ?
C13 C14 C15 C16 -178.76(9) . . . . ?
C3 C12 C11 C10 -0.4(4) . . . . ?
C3 C4 C5 C6 179.73(16) . . . . ?
C3 C4 C5 C1 -1.8(4) . . . . ?
C3 C4 C9 C10 1.3(4) . . . . ?
C3 C4 C9 C8 -179.45(15) . . . . ?
C9 C4 C5 C6 1.1(4) . . . . ?
C9 C4 C5 C1 179.61(17) . . . . ?
C9 C4 C3 C2 179.59(16) . . . . ?
C9 C4 C3 C12 -1.1(4) . . . . ?
C8 C10 C9 C4 -179.88(14) 2_556 . . . ?
C8 C10 C9 C8 0.9(4) 2_556 . . . ?
C8 C7 C6 C5 1.9(4) . . . . ?
C6 C5 C1 O1 1.0(4) . . . . ?
C6 C5 C1 N1 -179.32(18) . . . . ?
C6 C7 C8 C10 179.58(15) . . . 2_556 ?
C6 C7 C8 C9 -1.7(4) . . . . ?
C18 C17 C16 C15 174.6(3) . . . . ?
C1 N1 C2 O2 -178.90(18) . . . . ?
C1 N1 C2 C3 1.1(4) . . . . ?
C1 N1 C13 C14 82.7(2) . . . . ?
C1 C5 C6 C7 179.84(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
;
####################################################################### 
# 
# 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_C6_4_61GPa
_database_code_depnum_ccdc_archive 'CCDC 2412029'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C6_4_61GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.310 Why?  
RESPONSE: These data come from a high-pressure experiment and part of the 
reflections could not be collected due to the limited DAC opening angle and the 
measurement strategy.
;
_vrf_PLAT088_PDI_C6_4_61GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       5.66 Note   
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber. 
;
_vrf_PLAT911_PDI_C6_4_61GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        905 Report
                0  2  0,  -1  4  0,  -1  5  0,  -2  6  0,  -1  6  0,  -3  7  0, 
               -2  7  0,  -1  7  0,  -3  8  0,  -2  8  0,  -1  8  0,   1  8  0, 
               -3  9  0,  -2  9  0,  -1  9  0,  -1 10  0,   0 10  0,   0-10  1, 
                1-10  1,   0 -9  1,   1 -9  1,   2 -9  1,   0 -8  1,   1 -8  1, 
                2 -8  1,   3 -8  1,   1 -7  1,   2 -7  1,   3 -7  1,   1 -6  1, 
                2 -6  1,   1 -5  1,   1 -4  1,   0 -2  1,   0  2  1,  -1  4  1, 
               -1  5  1,  -1  6  1,   1  6  1,  -2  7  1,  -1  7  1,   1  7  1, 
               -3  8  1,  -2  8  1,  -1  8  1,   1  8  1,  -3  9  1,  -2  9  1, 
               -1  9  1,  -1 10  1,   0-10  2,   1-10  2,   0 -9  2,   1 -9  2, 
                2 -9  2,   0 -8  2,   1 -8  2,   2 -8  2,   3 -8  2,   0 -7  2, 
                1 -7  2,   2 -7  2,   1 -6  2,   2 -6  2,   1 -5  2,   1 -3  2, 
                2 -3  2,   0 -2  2,   1 -2  2,   1 -1  2,   1  0  2,   4  0  2, 
                1  1  2,  -1  2  2,   0  2  2,  -1  3  2,   0  3  2,  -2  4  2, 
               -1  4  2,   0  4  2,  -1  5  2,  -1  6  2,   1  6  2,   2  6  2, 
               -2  7  2,  -1  7  2,   2  7  2,  -2  8  2,  -1  8  2,   1  8  2, 
               -2  9  2,  -1  9  2,   0  9  2,  -1 10  2,   0 10  2,   0-10  3, 
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-06-07
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   4.29260(10)
_cell_length_b                   8.5559(3)
_cell_length_c                   15.3181(19)
_cell_angle_alpha                90.875(6)
_cell_angle_beta                 93.694(4)
_cell_angle_gamma                97.093(2)
_cell_volume                     556.97(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1548
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.3530
_cell_measurement_theta_min      3.3170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82232
_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    1.666
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_preparation       'mounted in a diamond-anvil cell'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.065
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0985
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.310
_diffrn_reflns_Laue_measured_fraction_max 0.204
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5719
_diffrn_reflns_point_group_measured_fraction_full 0.310
_diffrn_reflns_point_group_measured_fraction_max 0.204
_diffrn_reflns_theta_full        17.159
_diffrn_reflns_theta_max         24.074
_diffrn_reflns_theta_min         3.316
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.310
_diffrn_measured_fraction_theta_max 0.204
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     18.00  97.00   0.20    0.50  57.05   0.00-134.76    --   395
  2  φ     18.00  97.00   0.20    0.50  57.05   0.00-134.76    --   395
  3  φ     18.00  97.00   0.20    0.50  57.05   0.00-134.76    --   395
  4  φ     18.00  97.00   0.20    0.50  57.05   0.00-134.76    --   395
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.49172
_diffrn_source                   synchrotron
_diffrn_special_details          
'Data were collected at room temperature and pressure of 4.61(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                855
_reflns_number_total             1082
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.038
_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     191
_refine_ls_number_reflns         1082
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.070
_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)+(0.1278P)²+0.0466P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1709
_refine_ls_wR_factor_ref         0.1854
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H4(0.048) H3(0.042) H7(0.05) H8(0.05) H17(0.057) H13(0.057)
 H10(0.054) H9(0.054) H2(0.045) H5(0.053) H6(0.053) H11(0.069) H12(0.069)
 H1(0.049) H16(0.08) H19B(0.08) H15(0.08)
 Fixed X: H4(0.75949) H3(0.39375) H7(0.790718) H8(1.122506) H17(1.094501)
 H13(1.053083) H10(1.070601) H9(0.741438) H2(-0.070135) H5(1.204736)
 H6(1.304236) H11(0.558364) H12(0.63373) H1(0.290482) H16(0.89004)
 H19B(0.658729) H15(0.592223)
 Fixed Y: H4(0.433713) H3(0.333942) H7(0.3596) H8(0.449387) H17(0.833138)
 H13(0.683135) H10(0.627419) H9(0.536884) H2(-0.242944) H5(0.231422)
 H6(0.378401) H11(0.607431) H12(0.748647) H1(-0.137452) H16(0.888804)
 H19B(0.922223) H15(0.767861)
 Fixed Z: H4(0.499662) H3(0.598812) H7(0.11382) H8(0.09815) H17(0.090308)
 H13(0.028254) H10(0.211596) H9(0.228809) H2(0.324426) H5(0.176862)
 H6(0.239562) H11(0.086629) H12(0.153849) H1(0.225097) H16(-0.050284)
 H19B(0.020925) H15(-0.037234)
;
_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 1.0649(3) 0.4528(2) 0.3664(3) 0.044(3) Uani 1 1 d . . . . .
O1 O 0.7225(5) 0.0554(3) 0.1701(4) 0.044(3) Uani 1 1 d . . . . .
N1 N 0.8990(4) 0.2512(2) 0.2702(4) 0.033(3) Uani 1 1 d . . . . .
C2 C 0.8859(4) 0.3310(3) 0.3466(4) 0.043(3) Uani 1 1 d . . . . .
C12 C 0.6269(4) 0.3412(3) 0.4855(4) 0.040(3) Uani 1 1 d . . . . .
H4 H 0.759490 0.433713 0.499662 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4058(4) 0.2823(3) 0.5455(4) 0.035(3) Uani 1 1 d . . . . .
H3 H 0.393750 0.333942 0.598812 0.042 Uiso 1 1 calc R U . . .
C14 C 0.9764(5) 0.4198(3) 0.1426(4) 0.041(3) Uani 1 1 d . . . . .
H7 H 0.790718 0.359600 0.113820 0.050 Uiso 1 1 calc R U . . .
H8 H 1.122506 0.449387 0.098150 0.050 Uiso 1 1 calc R U . . .
C17 C 0.9408(5) 0.7576(3) 0.0580(4) 0.047(3) Uani 1 1 d . . . . .
H17 H 1.094501 0.833138 0.090308 0.057 Uiso 1 1 calc R U . . .
H13 H 1.053083 0.683135 0.028254 0.057 Uiso 1 1 calc R U . . .
C4 C 0.4492(4) 0.1260(3) 0.3825(4) 0.035(3) Uani 1 1 d . . . . .
C10 C 0.2042(4) 0.1426(2) 0.5219(4) 0.034(3) Uani 1 1 d . . . . .
C5 C 0.4728(5) 0.0504(3) 0.3043(4) 0.040(3) Uani 1 1 d . . . . .
C15 C 0.8837(5) 0.5671(3) 0.1836(4) 0.045(3) Uani 1 1 d . . . . .
H10 H 1.070601 0.627419 0.211596 0.054 Uiso 1 1 calc R U . . .
H9 H 0.741438 0.536884 0.228809 0.054 Uiso 1 1 calc R U . . .
C7 C 0.0575(5) -0.1491(3) 0.3390(4) 0.037(3) Uani 1 1 d . . . . .
H2 H -0.070135 -0.242944 0.324426 0.045 Uiso 1 1 calc R U . . .
C13 C 1.1267(4) 0.3169(3) 0.2077(4) 0.044(3) Uani 1 1 d . . . . .
H5 H 1.204736 0.231422 0.176862 0.053 Uiso 1 1 calc R U . . .
H6 H 1.304236 0.378401 0.239562 0.053 Uiso 1 1 calc R U . . .
C16 C 0.7275(5) 0.6716(3) 0.1204(5) 0.057(4) Uani 1 1 d . . . . .
H11 H 0.558364 0.607431 0.086629 0.069 Uiso 1 1 calc R U . . .
H12 H 0.633730 0.748647 0.153849 0.069 Uiso 1 1 calc R U . . .
C3 C 0.6499(4) 0.2676(3) 0.4091(4) 0.036(3) Uani 1 1 d . . . . .
C9 C 0.2249(4) 0.0650(3) 0.4440(4) 0.038(3) Uani 1 1 d . . . . .
C8 C 0.0263(5) -0.0780(2) 0.4153(4) 0.033(3) Uani 1 1 d . . . . .
C6 C 0.2773(5) -0.0878(3) 0.2789(4) 0.041(3) Uani 1 1 d . . . . .
H1 H 0.290482 -0.137452 0.225097 0.049 Uiso 1 1 calc R U . . .
C18 C 0.7536(5) 0.8417(3) -0.0081(5) 0.053(4) Uani 1 1 d . . . . .
H16 H 0.890040 0.888804 -0.050284 0.080 Uiso 1 1 calc R U . . .
H19B H 0.658729 0.922223 0.020925 0.080 Uiso 1 1 calc R U . . .
H15 H 0.592223 0.767861 -0.037234 0.080 Uiso 1 1 calc R U . . .
C1 C 0.7018(5) 0.1140(3) 0.2412(5) 0.040(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.238(4) . ?
O1 C1 1.206(10) . ?
N1 C2 1.353(8) . ?
N1 C13 1.480(5) . ?
N1 C1 1.408(5) . ?
C2 C3 1.497(5) . ?
C12 H4 0.9300 . ?
C12 C11 1.417(5) . ?
C12 C3 1.336(8) . ?
C11 H3 0.9300 . ?
C11 C10 1.414(4) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C15 1.508(5) . ?
C14 C13 1.507(6) . ?
C17 H17 0.9700 . ?
C17 H13 0.9700 . ?
C17 C16 1.504(6) . ?
C17 C18 1.500(7) . ?
C4 C5 1.369(9) . ?
C4 C3 1.434(4) . ?
C4 C9 1.448(6) . ?
C10 C9 1.369(9) . ?
C10 C8 1.488(5) 2_556 ?
C5 C6 1.397(4) . ?
C5 C1 1.483(6) . ?
C15 H10 0.9700 . ?
C15 H9 0.9700 . ?
C15 C16 1.508(6) . ?
C7 H2 0.9300 . ?
C7 C8 1.331(9) . ?
C7 C6 1.420(5) . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C9 C8 1.447(5) . ?
C6 H1 0.9300 . ?
C18 H16 0.9600 . ?
C18 H19B 0.9600 . ?
C18 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
C2 N1 C13 118.2(2) . . ?
C2 N1 C1 126.1(4) . . ?
C1 N1 C13 115.6(5) . . ?
O2 C2 N1 122.0(4) . . ?
O2 C2 C3 119.5(5) . . ?
N1 C2 C3 118.5(3) . . ?
C11 C12 H4 119.1 . . ?
C3 C12 H4 119.1 . . ?
C3 C12 C11 121.8(3) . . ?
C12 C11 H3 121.0 . . ?
C10 C11 C12 118.0(5) . . ?
C10 C11 H3 121.0 . . ?
H7 C14 H8 107.8 . . ?
C15 C14 H7 108.9 . . ?
C15 C14 H8 108.9 . . ?
C13 C14 H7 108.9 . . ?
C13 C14 H8 108.9 . . ?
C13 C14 C15 113.2(5) . . ?
H17 C17 H13 108.1 . . ?
C16 C17 H17 109.6 . . ?
C16 C17 H13 109.6 . . ?
C18 C17 H17 109.6 . . ?
C18 C17 H13 109.6 . . ?
C18 C17 C16 110.4(2) . . ?
C5 C4 C3 122.0(4) . . ?
C5 C4 C9 121.7(3) . . ?
C3 C4 C9 116.3(5) . . ?
C11 C10 C8 118.6(5) . 2_556 ?
C9 C10 C11 121.1(4) . . ?
C9 C10 C8 120.2(3) . 2_556 ?
C4 C5 C6 121.7(4) . . ?
C4 C5 C1 121.4(3) . . ?
C6 C5 C1 116.8(5) . . ?
C14 C15 H10 108.6 . . ?
C14 C15 H9 108.6 . . ?
C14 C15 C16 114.6(5) . . ?
H10 C15 H9 107.6 . . ?
C16 C15 H10 108.6 . . ?
C16 C15 H9 108.6 . . ?
C8 C7 H2 118.6 . . ?
C8 C7 C6 122.8(3) . . ?
C6 C7 H2 118.6 . . ?
N1 C13 C14 111.1(2) . . ?
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 . . ?
C17 C16 C15 115.3(2) . . ?
C17 C16 H11 108.5 . . ?
C17 C16 H12 108.5 . . ?
C15 C16 H11 108.5 . . ?
C15 C16 H12 108.5 . . ?
H11 C16 H12 107.5 . . ?
C12 C3 C2 121.1(3) . . ?
C12 C3 C4 122.0(4) . . ?
C4 C3 C2 116.9(5) . . ?
C10 C9 C4 120.8(3) . . ?
C10 C9 C8 124.2(4) . . ?
C8 C9 C4 114.9(5) . . ?
C7 C8 C10 122.7(3) . 2_556 ?
C7 C8 C9 121.8(4) . . ?
C9 C8 C10 115.5(5) . 2_556 ?
C5 C6 C7 117.0(5) . . ?
C5 C6 H1 121.5 . . ?
C7 C6 H1 121.5 . . ?
C17 C18 H16 109.5 . . ?
C17 C18 H19B 109.5 . . ?
C17 C18 H15 109.5 . . ?
H16 C18 H19B 109.5 . . ?
H16 C18 H15 109.5 . . ?
H19B C18 H15 109.5 . . ?
O1 C1 N1 121.1(4) . . ?
O1 C1 C5 123.9(3) . . ?
N1 C1 C5 115.0(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 C12 0.8(6) . . . . ?
O2 C2 C3 C4 -179.9(3) . . . . ?
N1 C2 C3 C12 179.8(3) . . . . ?
N1 C2 C3 C4 -0.9(6) . . . . ?
C2 N1 C13 C14 -92.8(5) . . . . ?
C2 N1 C1 O1 176.5(4) . . . . ?
C2 N1 C1 C5 -3.4(6) . . . . ?
C12 C11 C10 C9 1.0(6) . . . . ?
C12 C11 C10 C8 179.2(3) . . . 2_556 ?
C11 C12 C3 C2 -179.7(3) . . . . ?
C11 C12 C3 C4 1.0(6) . . . . ?
C11 C10 C9 C4 -1.5(6) . . . . ?
C11 C10 C9 C8 -179.8(3) . . . . ?
C14 C15 C16 C17 -71.3(4) . . . . ?
C4 C5 C6 C7 -1.6(6) . . . . ?
C4 C5 C1 O1 -176.8(4) . . . . ?
C4 C5 C1 N1 3.1(6) . . . . ?
C4 C9 C8 C10 179.7(2) . . . 2_556 ?
C4 C9 C8 C7 2.0(6) . . . . ?
C10 C9 C8 C10 -2.0(7) . . . 2_556 ?
C10 C9 C8 C7 -179.7(4) . . . . ?
C5 C4 C3 C2 0.8(6) . . . . ?
C5 C4 C3 C12 -179.9(3) . . . . ?
C5 C4 C9 C10 -179.8(3) . . . . ?
C5 C4 C9 C8 -1.5(6) . . . . ?
C15 C14 C13 N1 66.2(3) . . . . ?
C13 N1 C2 O2 -2.6(6) . . . . ?
C13 N1 C2 C3 178.3(2) . . . . ?
C13 N1 C1 O1 0.4(6) . . . . ?
C13 N1 C1 C5 -179.4(3) . . . . ?
C13 C14 C15 C16 -179.02(15) . . . . ?
C3 C12 C11 C10 -0.8(6) . . . . ?
C3 C4 C5 C6 179.8(3) . . . . ?
C3 C4 C5 C1 -2.0(7) . . . . ?
C3 C4 C9 C10 1.7(6) . . . . ?
C3 C4 C9 C8 -179.9(3) . . . . ?
C9 C4 C5 C6 1.4(7) . . . . ?
C9 C4 C5 C1 179.6(3) . . . . ?
C9 C4 C3 C2 179.2(2) . . . . ?
C9 C4 C3 C12 -1.4(6) . . . . ?
C8 C10 C9 C4 -179.7(2) 2_556 . . . ?
C8 C10 C9 C8 2.1(7) 2_556 . . . ?
C8 C7 C6 C5 2.2(6) . . . . ?
C6 C5 C1 O1 1.6(7) . . . . ?
C6 C5 C1 N1 -178.6(3) . . . . ?
C6 C7 C8 C10 -180.0(3) . . . 2_556 ?
C6 C7 C8 C9 -2.5(7) . . . . ?
C18 C17 C16 C15 173.2(4) . . . . ?
C1 N1 C2 O2 -178.6(3) . . . . ?
C1 N1 C2 C3 2.4(6) . . . . ?
C1 N1 C13 C14 83.6(4) . . . . ?
C1 C5 C6 C7 -179.9(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_C6_1_41GPa
_database_code_depnum_ccdc_archive 'CCDC 2412022'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C6_1_41GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.328 Why?    
RESPONSE: These data come from a high-pressure experiment and part of the 
reflections could not be collected due to the limited DAC opening angle and the 
measurement strategy.
;
_vrf_PLAT088_PDI_C6_1_41GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.54 Note 
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber. 
;
_vrf_PLAT910_PDI_C6_1_41GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).         20 Note  
                0  1  0,   0  2  0,   0  3  0,   0 -2  1,   0 -1  1,   0  0  1, 
                0  1  1,   0  2  1,   0  3  1,   0 -2  2,   0 -1  2,   0  0  2, 
                0  1  2,   0  2  2,   0  3  2,   0 -1  3,   0  0  3,   0  1  3, 
                0  2  3,   0  3  3,   
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
_vrf_PLAT911_PDI_C6_1_41GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600       2395 Report
               -1  4  0,   0  4  0,   0  5  0,   0  6  0,   0  7  0,  -1  8  0, 
                0  8  0,   2  8  0,   1  9  0,   1 10  0,   1 11  0,   1 12  0, 
               -3 13  0,   1 13  0,   1 14  0,   1 15  0,  -2 16  0,   1 16  0, 
                2 16  0,   1 17  0,   1 18  0,  -1-17  1,  -1-16  1,   0-16  1, 
               -2-15  1,  -1-15  1,   0-15  1,   1-15  1,  -1-14  1,   0-14  1, 
               -1-13  1,   0-13  1,   3-13  1,  -1-12  1,   0-12  1,   2-12  1, 
               -1-11  1,   0-11  1,  -1-10  1,   0-10  1,  -1 -9  1,   0 -9  1, 
               -1 -8  1,   0 -8  1,  -2 -7  1,  -1 -7  1,   0 -7  1,   1 -7  1, 
               -2 -6  1,  -1 -6  1,   0 -6  1,  -1 -5  1,   0 -5  1,   1 -5  1, 
                0 -4  1,   0 -3  1,  -2 -1  1,  -1  0  1,   0  4  1,   0  5  1, 
                0  6  1,   1  8  1,   1  9  1,   1 10  1,   1 11  1,   1 12  1, 
                2 12  1,   1 13  1,   1 14  1,   3 14  1,   1 15  1,   2 15  1, 
               -2 16  1,   1 16  1,   2 16  1,   1 17  1,   2 17  1,   1 18  1, 
               -1-17  2,   0-17  2,   1-17  2,  -1-16  2,   0-16  2,   1-16  2, 
                2-16  2,  -2-15  2,  -1-15  2,   0-15  2,   1-15  2,   2-15  2, 
                3-15  2,  -2-14  2,  -1-14  2,   0-14  2,   1-14  2,   2-14  2,
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-06-07
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         '2(C18 H17 N O2)'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   4.53080(10)
_cell_length_b                   16.9532(3)
_cell_length_c                   17.8870(10)
_cell_angle_alpha                66.484(3)
_cell_angle_beta                 95.489(2)
_cell_angle_gamma                96.2870(10)
_cell_volume                     1250.21(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5532
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3110
_cell_measurement_theta_min      3.1300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.051
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58865
_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    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_preparation       'mounted in a diamond-anvil cell'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.069
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.328
_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       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13675
_diffrn_reflns_point_group_measured_fraction_full 0.328
_diffrn_reflns_point_group_measured_fraction_max 0.181
_diffrn_reflns_theta_full        17.160
_diffrn_reflns_theta_max         25.299
_diffrn_reflns_theta_min         3.135
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.328
_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     18.00  96.00   0.20    0.50  57.05   0.00-134.76    --   390
  2  φ     18.00  96.00   0.20    0.50  57.05   0.00-134.76    --   390
  3  φ     18.00  96.00   0.20    0.50  57.05   0.00-134.76    --   390
  4  φ     18.00  96.00   0.20    0.50  57.05   0.00-134.76    --   390
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.49173
_diffrn_source                   synchrotron
_diffrn_special_details          
'Data were collected at room temperature and pressure of 1.41(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                2100
_reflns_number_total             2491
_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    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         2491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0610
_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)+(0.1541P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1714
_refine_ls_wR_factor_ref         0.1786
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C14(H8,H7), C33(H26,H27), C31(H22,H23), C15(H10,H9), C16(H12,H11), C32(H24,
 H25), C34(H28,H29), C13(H6,H5), C35(H30,H31), C17(H14,H13)
1.b Aromatic/amide H refined with riding coordinates:
 C30(H21), C29(H20), C24(H18), C7(H3), C25(H19), C12(H1), C11(H2), C6(H4)
1.c Idealised Me refined as rotating group:
 C18(H15,H17,H16), C36(H34,H32,H33)
;
_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
O4 O 0.5231(2) 0.77618(10) 0.3693(2) 0.0424(17) Uani 1 1 d . . . . .
O1 O 0.5010(2) 0.71333(10) 0.6211(2) 0.0431(18) Uani 1 1 d . . . . .
N1 N 0.6827(2) 0.76157(13) 0.7197(3) 0.032(2) Uani 1 1 d . . . . .
C20 C 0.3412(3) 0.72590(13) 0.3511(3) 0.033(2) Uani 1 1 d . . . . .
C4 C 1.0909(3) 0.88060(14) 0.6111(3) 0.023(2) Uani 1 1 d . . . . .
N2 N 0.3352(2) 0.72114(11) 0.2762(3) 0.034(2) Uani 1 1 d . . . . .
C30 C 0.1176(2) 0.67098(12) 0.4847(3) 0.031(2) Uani 1 1 d . . . . .
H21 H 0.252676 0.708900 0.498822 0.037 Uiso 1 1 calc R U . . .
C23 C -0.0750(3) 0.60758(12) 0.3111(3) 0.027(2) Uani 1 1 d . . . . .
C29 C -0.0880(2) 0.61768(11) 0.5410(2) 0.0300(19) Uani 1 1 d . . . . .
H20 H -0.088081 0.620723 0.591791 0.036 Uiso 1 1 calc R U . . .
C9 C 1.2938(3) 0.94027(13) 0.5535(3) 0.026(2) Uani 1 1 d . . . . .
O3 O 0.1424(3) 0.66663(16) 0.1831(3) 0.048(2) Uani 1 1 d . . . . .
C22 C -0.0822(3) 0.61082(12) 0.3863(3) 0.029(2) Uani 1 1 d . . . . .
C28 C -0.2940(3) 0.55966(12) 0.5212(3) 0.031(2) Uani 1 1 d . . . . .
C14 C 0.6557(3) 0.61238(11) 0.8211(2) 0.042(2) Uani 1 1 d . . . . .
H8 H 0.736884 0.597970 0.780341 0.051 Uiso 1 1 calc R U . . .
H7 H 0.821096 0.623860 0.854957 0.051 Uiso 1 1 calc R U . . .
C24 C -0.2725(3) 0.55111(13) 0.2880(3) 0.037(2) Uani 1 1 d . . . . .
H18 H -0.268642 0.550118 0.236455 0.044 Uiso 1 1 calc R U . . .
C7 C 1.0853(2) 0.88902(12) 0.4501(3) 0.033(2) Uani 1 1 d . . . . .
H3 H 1.082754 0.890873 0.397398 0.039 Uiso 1 1 calc R U . . .
C33 C 0.3203(3) 0.91919(12) 0.1975(3) 0.043(2) Uani 1 1 d . . . . .
H26 H 0.506054 0.939957 0.217697 0.052 Uiso 1 1 calc R U . . .
H27 H 0.203112 0.885627 0.244159 0.052 Uiso 1 1 calc R U . . .
C10 C 1.4991(3) 0.99429(14) 0.5833(3) 0.021(2) Uani 1 1 d . . . . .
C26 C -0.4921(3) 0.49731(12) 0.4194(3) 0.029(2) Uani 1 1 d . . . . .
C31 C 0.5387(3) 0.78048(12) 0.2144(3) 0.036(2) Uani 1 1 d . . . . .
H22 H 0.604543 0.750473 0.183545 0.044 Uiso 1 1 calc R U . . .
H23 H 0.712682 0.798100 0.241743 0.044 Uiso 1 1 calc R U . . .
C19 C 0.1354(3) 0.66597(17) 0.2499(4) 0.038(3) Uani 1 1 d . . . . .
C15 C 0.4618(2) 0.53550(11) 0.8740(2) 0.044(2) Uani 1 1 d . . . . .
H10 H 0.296858 0.523184 0.840491 0.053 Uiso 1 1 calc R U . . .
H9 H 0.380659 0.549244 0.915199 0.053 Uiso 1 1 calc R U . . .
C16 C 0.6375(3) 0.45548(12) 0.9158(3) 0.048(2) Uani 1 1 d . . . . .
H12 H 0.726658 0.444289 0.874164 0.058 Uiso 1 1 calc R U . . .
H11 H 0.797898 0.467973 0.950395 0.058 Uiso 1 1 calc R U . . .
C25 C -0.4763(3) 0.49598(14) 0.3434(3) 0.033(2) Uani 1 1 d . . . . .
H19 H -0.604887 0.457351 0.328549 0.040 Uiso 1 1 calc R U . . .
C32 C 0.3873(3) 0.86064(12) 0.1557(3) 0.039(2) Uani 1 1 d . . . . .
H24 H 0.515146 0.893135 0.111202 0.047 Uiso 1 1 calc R U . . .
H25 H 0.202921 0.842615 0.132618 0.047 Uiso 1 1 calc R U . . .
C18 C 0.6528(4) 0.30122(16) 1.0165(4) 0.062(3) Uani 1 1 d . . . . .
H15 H 0.804683 0.320826 1.047776 0.092 Uiso 1 1 calc R U . . .
H17 H 0.743581 0.283418 0.980035 0.092 Uiso 1 1 calc R U . . .
H16 H 0.533553 0.253352 1.052728 0.092 Uiso 1 1 calc R U . . .
C34 C 0.1515(3) 0.99685(13) 0.1407(3) 0.042(2) Uani 1 1 d . . . . .
H28 H -0.030857 0.975485 0.119580 0.051 Uiso 1 1 calc R U . . .
H29 H 0.096136 1.026796 0.172910 0.051 Uiso 1 1 calc R U . . .
C3 C 1.0906(3) 0.87554(15) 0.6903(3) 0.030(2) Uani 1 1 d . . . . .
C13 C 0.4919(3) 0.69440(12) 0.7779(3) 0.040(2) Uani 1 1 d . . . . .
H6 H 0.311722 0.681891 0.749335 0.048 Uiso 1 1 calc R U . . .
H5 H 0.436095 0.714535 0.817878 0.048 Uiso 1 1 calc R U . . .
C8 C 1.2912(3) 0.94380(13) 0.4746(3) 0.029(2) Uani 1 1 d . . . . .
C12 C 1.2926(3) 0.92788(14) 0.7178(3) 0.037(2) Uani 1 1 d . . . . .
H1 H 1.295450 0.924066 0.771211 0.044 Uiso 1 1 calc R U . . .
C27 C -0.2902(3) 0.55572(11) 0.4441(3) 0.026(2) Uani 1 1 d . . . . .
C21 C 0.1233(2) 0.66830(12) 0.4106(3) 0.028(2) Uani 1 1 d . . . . .
C35 C 0.3168(3) 1.06083(14) 0.0699(3) 0.041(2) Uani 1 1 d . . . . .
H30 H 0.376521 1.031416 0.037713 0.049 Uiso 1 1 calc R U . . .
H31 H 0.495641 1.084504 0.090314 0.049 Uiso 1 1 calc R U . . .
C1 C 0.6764(3) 0.76374(14) 0.6415(3) 0.028(2) Uani 1 1 d . . . . .
C17 C 0.4562(3) 0.37457(12) 0.9671(3) 0.045(2) Uani 1 1 d . . . . .
H14 H 0.314978 0.356339 0.931735 0.054 Uiso 1 1 calc R U . . .
H13 H 0.344653 0.387237 1.004116 0.054 Uiso 1 1 calc R U . . .
C11 C 1.4924(3) 0.98685(17) 0.6618(4) 0.032(3) Uani 1 1 d . . . . .
H2 H 1.626193 1.022359 0.679454 0.039 Uiso 1 1 calc R U . . .
C36 C 0.1305(4) 1.13431(17) 0.0153(4) 0.061(3) Uani 1 1 d . . . . .
H34 H 0.075815 1.164750 0.046411 0.091 Uiso 1 1 calc R U . . .
H32 H -0.045816 1.111282 -0.005630 0.091 Uiso 1 1 calc R U . . .
H33 H 0.244150 1.173219 -0.029359 0.091 Uiso 1 1 calc R U . . .
C5 C 0.8846(3) 0.82673(14) 0.5824(3) 0.029(2) Uani 1 1 d . . . . .
C6 C 0.8832(3) 0.83138(14) 0.5057(3) 0.027(2) Uani 1 1 d . . . . .
H4 H 0.746245 0.795854 0.488906 0.032 Uiso 1 1 calc R U . . .
O2 O 0.8752(4) 0.80733(19) 0.8185(4) 0.042(3) Uani 1 1 d . . . . .
C2 C 0.8801(4) 0.8140(2) 0.7484(4) 0.033(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C20 1.237(2) . ?
O1 C1 1.241(3) . ?
N1 C13 1.462(4) . ?
N1 C1 1.381(6) . ?
N1 C2 1.399(4) . ?
C20 N2 1.372(6) . ?
C20 C21 1.491(4) . ?
C4 C9 1.440(5) . ?
C4 C3 1.385(7) . ?
C4 C5 1.437(4) . ?
N2 C31 1.479(4) . ?
N2 C19 1.414(4) . ?
C30 H21 0.9300 . ?
C30 C29 1.403(4) . ?
C30 C21 1.347(6) . ?
C23 C22 1.371(6) . ?
C23 C24 1.395(3) . ?
C23 C19 1.488(5) . ?
C29 H20 0.9300 . ?
C29 C28 1.407(3) . ?
C9 C10 1.448(4) . ?
C9 C8 1.388(7) . ?
O3 C19 1.194(8) . ?
C22 C27 1.433(4) . ?
C22 C21 1.438(3) . ?
C28 C26 1.475(4) 2_466 ?
C28 C27 1.409(7) . ?
C14 H8 0.9700 . ?
C14 H7 0.9700 . ?
C14 C15 1.513(3) . ?
C14 C13 1.530(3) . ?
C24 H18 0.9300 . ?
C24 C25 1.399(4) . ?
C7 H3 0.9300 . ?
C7 C8 1.407(3) . ?
C7 C6 1.409(4) . ?
C33 H26 0.9700 . ?
C33 H27 0.9700 . ?
C33 C32 1.529(4) . ?
C33 C34 1.535(4) . ?
C10 C8 1.477(5) 2_876 ?
C10 C11 1.361(7) . ?
C26 C25 1.377(7) . ?
C26 C27 1.444(3) . ?
C31 H22 0.9700 . ?
C31 H23 0.9700 . ?
C31 C32 1.532(4) . ?
C15 H10 0.9700 . ?
C15 H9 0.9700 . ?
C15 C16 1.532(3) . ?
C16 H12 0.9700 . ?
C16 H11 0.9700 . ?
C16 C17 1.514(3) . ?
C25 H19 0.9300 . ?
C32 H24 0.9700 . ?
C32 H25 0.9700 . ?
C18 H15 0.9600 . ?
C18 H17 0.9600 . ?
C18 H16 0.9600 . ?
C18 C17 1.528(4) . ?
C34 H28 0.9700 . ?
C34 H29 0.9700 . ?
C34 C35 1.500(5) . ?
C3 C12 1.397(4) . ?
C3 C2 1.478(6) . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C12 H1 0.9300 . ?
C12 C11 1.414(5) . ?
C35 H30 0.9700 . ?
C35 H31 0.9700 . ?
C35 C36 1.523(4) . ?
C1 C5 1.489(5) . ?
C17 H14 0.9700 . ?
C17 H13 0.9700 . ?
C11 H2 0.9300 . ?
C36 H34 0.9600 . ?
C36 H32 0.9600 . ?
C36 H33 0.9600 . ?
C5 C6 1.342(7) . ?
C6 H4 0.9300 . ?
O2 C2 1.214(9) . ?

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 117.6(2) . . ?
C1 N1 C2 124.0(3) . . ?
C2 N1 C13 118.1(4) . . ?
O4 C20 N2 121.2(3) . . ?
O4 C20 C21 120.5(4) . . ?
N2 C20 C21 118.3(2) . . ?
C3 C4 C9 121.9(3) . . ?
C3 C4 C5 121.1(3) . . ?
C5 C4 C9 117.0(5) . . ?
C20 N2 C31 119.49(19) . . ?
C20 N2 C19 125.2(3) . . ?
C19 N2 C31 115.3(4) . . ?
C29 C30 H21 119.4 . . ?
C21 C30 H21 119.4 . . ?
C21 C30 C29 121.3(2) . . ?
C22 C23 C24 121.1(3) . . ?
C22 C23 C19 121.6(2) . . ?
C24 C23 C19 117.3(4) . . ?
C30 C29 H20 119.8 . . ?
C30 C29 C28 120.4(4) . . ?
C28 C29 H20 119.8 . . ?
C4 C9 C10 116.2(5) . . ?
C8 C9 C4 120.9(3) . . ?
C8 C9 C10 122.9(3) . . ?
C23 C22 C27 121.2(2) . . ?
C23 C22 C21 121.2(3) . . ?
C27 C22 C21 117.6(4) . . ?
C29 C28 C26 120.6(4) . 2_466 ?
C29 C28 C27 119.0(3) . . ?
C27 C28 C26 120.3(2) . 2_466 ?
H8 C14 H7 107.7 . . ?
C15 C14 H8 108.8 . . ?
C15 C14 H7 108.8 . . ?
C15 C14 C13 113.84(12) . . ?
C13 C14 H8 108.8 . . ?
C13 C14 H7 108.8 . . ?
C23 C24 H18 120.5 . . ?
C23 C24 C25 119.0(4) . . ?
C25 C24 H18 120.5 . . ?
C8 C7 H3 120.1 . . ?
C8 C7 C6 119.8(4) . . ?
C6 C7 H3 120.1 . . ?
H26 C33 H27 107.8 . . ?
C32 C33 H26 109.0 . . ?
C32 C33 H27 109.0 . . ?
C32 C33 C34 113.1(3) . . ?
C34 C33 H26 109.0 . . ?
C34 C33 H27 109.0 . . ?
C9 C10 C8 117.2(5) . 2_876 ?
C11 C10 C9 119.9(3) . . ?
C11 C10 C8 122.8(3) . 2_876 ?
C25 C26 C28 123.0(2) . 2_466 ?
C25 C26 C27 119.8(3) . . ?
C27 C26 C28 117.2(4) . 2_466 ?
N2 C31 H22 109.3 . . ?
N2 C31 H23 109.3 . . ?
N2 C31 C32 111.55(13) . . ?
H22 C31 H23 108.0 . . ?
C32 C31 H22 109.3 . . ?
C32 C31 H23 109.3 . . ?
N2 C19 C23 115.6(5) . . ?
O3 C19 N2 121.0(4) . . ?
O3 C19 C23 123.5(2) . . ?
C14 C15 H10 109.3 . . ?
C14 C15 H9 109.3 . . ?
C14 C15 C16 111.50(12) . . ?
H10 C15 H9 108.0 . . ?
C16 C15 H10 109.3 . . ?
C16 C15 H9 109.3 . . ?
C15 C16 H12 108.6 . . ?
C15 C16 H11 108.6 . . ?
H12 C16 H11 107.5 . . ?
C17 C16 C15 114.84(12) . . ?
C17 C16 H12 108.6 . . ?
C17 C16 H11 108.6 . . ?
C24 C25 H19 119.1 . . ?
C26 C25 C24 121.9(2) . . ?
C26 C25 H19 119.1 . . ?
C33 C32 C31 112.6(3) . . ?
C33 C32 H24 109.1 . . ?
C33 C32 H25 109.1 . . ?
C31 C32 H24 109.1 . . ?
C31 C32 H25 109.1 . . ?
H24 C32 H25 107.8 . . ?
H15 C18 H17 109.5 . . ?
H15 C18 H16 109.5 . . ?
H17 C18 H16 109.5 . . ?
C17 C18 H15 109.5 . . ?
C17 C18 H17 109.5 . . ?
C17 C18 H16 109.5 . . ?
C33 C34 H28 108.3 . . ?
C33 C34 H29 108.3 . . ?
H28 C34 H29 107.4 . . ?
C35 C34 C33 115.77(15) . . ?
C35 C34 H28 108.3 . . ?
C35 C34 H29 108.3 . . ?
C4 C3 C12 120.8(3) . . ?
C4 C3 C2 121.2(3) . . ?
C12 C3 C2 118.1(5) . . ?
N1 C13 C14 110.13(13) . . ?
N1 C13 H6 109.6 . . ?
N1 C13 H5 109.6 . . ?
C14 C13 H6 109.6 . . ?
C14 C13 H5 109.6 . . ?
H6 C13 H5 108.1 . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 C10 119.9(3) . 2_876 ?
C7 C8 C10 120.5(5) . 2_876 ?
C3 C12 H1 121.1 . . ?
C3 C12 C11 117.8(4) . . ?
C11 C12 H1 121.1 . . ?
C22 C27 C26 117.1(4) . . ?
C28 C27 C22 120.5(2) . . ?
C28 C27 C26 122.4(3) . . ?
C30 C21 C20 120.7(2) . . ?
C30 C21 C22 121.2(3) . . ?
C22 C21 C20 118.1(4) . . ?
C34 C35 H30 109.1 . . ?
C34 C35 H31 109.1 . . ?
C34 C35 C36 112.39(19) . . ?
H30 C35 H31 107.9 . . ?
C36 C35 H30 109.1 . . ?
C36 C35 H31 109.1 . . ?
O1 C1 N1 120.4(3) . . ?
O1 C1 C5 120.5(4) . . ?
N1 C1 C5 119.2(2) . . ?
C16 C17 C18 111.81(14) . . ?
C16 C17 H14 109.3 . . ?
C16 C17 H13 109.3 . . ?
C18 C17 H14 109.3 . . ?
C18 C17 H13 109.3 . . ?
H14 C17 H13 107.9 . . ?
C10 C11 C12 123.4(3) . . ?
C10 C11 H2 118.3 . . ?
C12 C11 H2 118.3 . . ?
C35 C36 H34 109.5 . . ?
C35 C36 H32 109.5 . . ?
C35 C36 H33 109.5 . . ?
H34 C36 H32 109.5 . . ?
H34 C36 H33 109.5 . . ?
H32 C36 H33 109.5 . . ?
C4 C5 C1 117.6(5) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 C1 120.9(3) . . ?
C7 C6 H4 119.4 . . ?
C5 C6 C7 121.3(2) . . ?
C5 C6 H4 119.4 . . ?
N1 C2 C3 116.9(5) . . ?
O2 C2 N1 120.1(4) . . ?
O2 C2 C3 122.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C20 N2 C31 -3.4(3) . . . . ?
O4 C20 N2 C19 -179.82(16) . . . . ?
O4 C20 C21 C30 1.1(3) . . . . ?
O4 C20 C21 C22 -179.69(14) . . . . ?
O1 C1 C5 C4 -177.28(14) . . . . ?
O1 C1 C5 C6 1.2(3) . . . . ?
N1 C1 C5 C4 2.2(3) . . . . ?
N1 C1 C5 C6 -179.34(19) . . . . ?
C20 N2 C31 C32 -95.1(3) . . . . ?
C20 N2 C19 C23 -2.0(3) . . . . ?
C20 N2 C19 O3 179.0(3) . . . . ?
C4 C9 C10 C8 -179.83(11) . . . 2_876 ?
C4 C9 C10 C11 0.0(3) . . . . ?
C4 C9 C8 C7 0.7(3) . . . . ?
C4 C9 C8 C10 179.84(12) . . . 2_876 ?
C4 C3 C12 C11 1.1(3) . . . . ?
C4 C3 C2 N1 0.0(4) . . . . ?
C4 C3 C2 O2 179.4(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
N2 C20 C21 C30 -179.35(18) . . . . ?
N2 C20 C21 C22 -0.1(3) . . . . ?
N2 C31 C32 C33 67.9(2) . . . . ?
C30 C29 C28 C26 179.18(14) . . . 2_466 ?
C30 C29 C28 C27 0.2(3) . . . . ?
C23 C22 C27 C28 179.80(17) . . . . ?
C23 C22 C27 C26 -0.4(3) . . . . ?
C23 C22 C21 C20 1.3(3) . . . . ?
C23 C22 C21 C30 -179.49(18) . . . . ?
C23 C24 C25 C26 1.5(3) . . . . ?
C29 C30 C21 C20 179.43(12) . . . . ?
C29 C30 C21 C22 0.2(3) . . . . ?
C29 C28 C27 C22 -0.8(3) . . . . ?
C29 C28 C27 C26 179.33(12) . . . . ?
C9 C4 C3 C12 -1.0(3) . . . . ?
C9 C4 C3 C2 179.85(16) . . . . ?
C9 C4 C5 C1 179.08(13) . . . . ?
C9 C4 C5 C6 0.6(3) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C22 C23 C24 C25 -1.2(3) . . . . ?
C22 C23 C19 N2 3.1(3) . . . . ?
C22 C23 C19 O3 -177.9(3) . . . . ?
C28 C26 C25 C24 179.60(14) 2_466 . . . ?
C28 C26 C27 C22 179.84(11) 2_466 . . . ?
C28 C26 C27 C28 -0.3(3) 2_466 . . . ?
C14 C15 C16 C17 -177.5(3) . . . . ?
C24 C23 C22 C27 0.7(3) . . . . ?
C24 C23 C22 C21 179.31(14) . . . . ?
C24 C23 C19 N2 -178.95(15) . . . . ?
C24 C23 C19 O3 0.1(4) . . . . ?
C33 C34 C35 C36 178.3(3) . . . . ?
C10 C9 C8 C7 179.83(12) . . . . ?
C10 C9 C8 C10 -1.0(4) . . . 2_876 ?
C26 C28 C27 C22 -179.84(12) 2_466 . . . ?
C26 C28 C27 C26 0.3(4) 2_466 . . . ?
C31 N2 C19 C23 -178.56(14) . . . . ?
C31 N2 C19 O3 2.4(4) . . . . ?
C19 N2 C31 C32 81.7(3) . . . . ?
C19 C23 C22 C27 178.55(16) . . . . ?
C19 C23 C22 C21 -2.8(3) . . . . ?
C19 C23 C24 C25 -179.19(17) . . . . ?
C15 C14 C13 N1 -172.1(3) . . . . ?
C15 C16 C17 C18 -171.7(3) . . . . ?
C25 C26 C27 C22 0.6(3) . . . . ?
C25 C26 C27 C28 -179.56(17) . . . . ?
C32 C33 C34 C35 -64.9(3) . . . . ?
C34 C33 C32 C31 -176.47(13) . . . . ?
C3 C4 C9 C10 0.4(3) . . . . ?
C3 C4 C9 C8 179.60(18) . . . . ?
C3 C4 C5 C1 -1.6(3) . . . . ?
C3 C4 C5 C6 179.9(2) . . . . ?
C3 C12 C11 C10 -0.7(3) . . . . ?
C13 N1 C1 O1 4.2(3) . . . . ?
C13 N1 C1 C5 -175.26(13) . . . . ?
C13 N1 C2 C3 174.14(16) . . . . ?
C13 N1 C2 O2 -5.3(4) . . . . ?
C13 C14 C15 C16 -179.9(3) . . . . ?
C8 C9 C10 C8 1.0(4) . . . 2_876 ?
C8 C9 C10 C11 -179.2(2) . . . . ?
C8 C7 C6 C5 -0.8(3) . . . . ?
C8 C10 C11 C12 179.96(14) 2_876 . . . ?
C12 C3 C2 N1 -179.23(16) . . . . ?
C12 C3 C2 O2 0.2(4) . . . . ?
C27 C22 C21 C20 179.92(13) . . . . ?
C27 C22 C21 C30 -0.8(3) . . . . ?
C27 C26 C25 C24 -1.2(4) . . . . ?
C21 C20 N2 C31 177.01(13) . . . . ?
C21 C20 N2 C19 0.6(3) . . . . ?
C21 C30 C29 C28 0.1(3) . . . . ?
C21 C22 C27 C28 1.1(3) . . . . ?
C21 C22 C27 C26 -179.02(13) . . . . ?
C1 N1 C13 C14 87.9(3) . . . . ?
C1 N1 C2 C3 0.7(4) . . . . ?
C1 N1 C2 O2 -178.8(3) . . . . ?
C1 C5 C6 C7 -178.11(12) . . . . ?
C5 C4 C9 C10 179.72(13) . . . . ?
C5 C4 C9 C8 -1.1(3) . . . . ?
C5 C4 C3 C12 179.76(13) . . . . ?
C5 C4 C3 C2 0.6(4) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C6 C7 C8 C10 -178.89(14) . . . 2_876 ?
C2 N1 C13 C14 -86.0(3) . . . . ?
C2 N1 C1 O1 177.71(16) . . . . ?
C2 N1 C1 C5 -1.7(4) . . . . ?
C2 C3 C12 C11 -179.74(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
;
####################################################################### 
# 
# 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_C6_470K
_database_code_depnum_ccdc_archive 'CCDC 2421130'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-12 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_ATOM007_PDI_C6_470K         
;
PROBLEM: _atom_site_aniso_label is missing
            Unique label identifying the atom site.
RESPONSE: The structure was refined isotropically 
due to the overall poor diffraction quality of the 
crystal and its low resolution.
;
_vrf_THETM01_PDI_C6_470K         
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength =    0.4005
RESPONSE: Due to the weak diffraction of these crystals, the data were
truncated to include only the part where reflections were observed.
;
_vrf_PLAT026_PDI_C6_470K         
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        19% Check 
RESPONSE: This low value results from a reconstructive transition and the overall 
poor diffraction quality of the crystal.
;
_vrf_PLAT027_PDI_C6_470K         
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      16.00 Degree 
RESPONSE: These data come from high-temperature studies, and the 
poor data quality is related to the progressive increase in thermal 
motions. Additionally, after undergoing a phase transition, this crystal
shattered and became poorly diffractive. Attempts to collect higher-quality
data at high temperatures were unsuccessful.
;
_vrf_PLAT029_PDI_C6_470K         
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.904 Why?  
RESPONSE: These data come from high-temperature studies, and the 
poor data quality is related to the progressive increase in thermal 
motions. Additionally, after undergoing a phase transition, this crystal
shattered and became poorly diffractive. Attempts to collect higher-quality
data at high temperatures were unsuccessful.
;
_vrf_PLAT084_PDI_C6_470K         
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.54 Report
RESPONSE: These data come from high-temperature studies, and the 
poor data quality is related to the progressive increase in thermal 
motions. Additionally, after undergoing a phase transition, this crystal
shattered and became poorly diffractive. Attempts to collect higher-quality
data at high temperatures were unsuccessful.
;
_vrf_PLAT201_PDI_C6_470K         
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         63 Report
              O101    O102    O103    O104    N101    N102    C41     C59       
              C101    C102    C103    C104    C105    C106    C107    C108      
              C109    C110    C111    C112    C113    C114    C115    C116      
              C117    C118    C119    C120    C121    C122    C123    C124      
              C125    C126    C127    C128    C129    C130    C131    C132      
              C133    C134    O201    O202    N201    C55     C58     C201      
              C202    C203    C204    C205    C206    C207    C208    C209      
              C210    C211    C212    C213    C214    C215    C216              
RESPONSE: The structure was refined isotropically due to the overall 
poor diffraction quality of the crystal. Furthermore, these data come from 
high-temperature studies, and the poor quality is related to the 
reconstructive phase transition and the progressive increase in thermal motion.
;
_vrf_PLAT241_PDI_C6_470K         
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of       C44 Check 
RESPONSE: These data come from high-temperature studies, and the poor data
quality is related to the reconstructive phase transition and the progressive 
increase in thermal motion of the atoms, which can lead to higher values of the Ueq. 
The issue is not due to the assignment of an incorrect atom type.
;
_vrf_PLAT242_PDI_C6_470K         
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of       C45 Check
RESPONSE: The issue is not due to the assignment of an incorrect atom type, 
but rather the poor quality of the experimental data. Additionally, this atom 
belongs to the terminal group, which may contribute to the low Ueq value 
and lead to a false alarm.
;
_vrf_PLAT412_PDI_C6_470K         
;
PROBLEM: Short Intra XH3 .. XHn     H31      ..H36      .       1.52 Ang.  
                                                      x,y,z  =      1_555 Check 
RESPONSE: These data come from high-temperature studies, and the short distance 
is likely a result of thermal motion and poor data quality.
;
_vrf_PLAT082_PDI_C6_470K         
;
PROBLEM: High R1 Value ..................................       0.18 Report
RESPONSE: These data come from high-temperature studies, and the 
poor data quality is related to the progressive increase in thermal 
motions. Additionally, after undergoing a phase transition, this crystal
shattered and became poorly diffractive. Attempts to collect higher-quality
data at high temperatures were unsuccessful.
;
_vrf_PLAT340_PDI_C6_470K         
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.05 Ang.  
RESPONSE: These data come from high-temperature studies, and the 
poor data quality is related to the progressive increase in thermal 
motions. Additionally, after undergoing a phase transition, this crystal
shattered and became poorly diffractive. Attempts to collect higher-quality
data at high temperatures were unsuccessful.
;
_vrf_PLAT410_PDI_C6_470K         
;
PROBLEM:  Short Intra H...H Contact  H20       ..H24      .       1.89 Ang.  
                                                      x,y,z  =      1_555 Check 
RESPONSE: These data come from high-temperature studies, and the short distance 
is likely a result of thermal motion and poor data quality.
;
_vrf_PLAT911_PDI_C6_470K         
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.400        458 Report
                7  0  0,  -8  1  0,  -7  1  0,   1  1  0,   7  1  0,  -1  2  0, 
               -1  3  0,   0  3  0,   1  3  0,  -8  4  0,  -7  4  0,  -1  4  0, 
                0  4  0,   1  4  0,  -8  5  0,  -7  5  0,  -1  5  0,   0  5  0, 
                1  5  0,  -8  6  0,  -7  6  0,  -1  6  0,   0  6  0,   1  6  0, 
               -8  7  0,  -7  8  0,  -6  9  0,  -1  9  0,   1 -9  1,   6 -9  1, 
                8 -7  1,   0 -6  1,   1 -6  1,   7 -6  1,   8 -6  1,   0 -5  1, 
                1 -5  1,   8 -5  1,  -1 -4  1,   7 -4  1,   8 -4  1,  -1 -2  1, 
                5 -2  1,   6 -2  1,   7 -1  1,   7  0  1,   8  0  1,  -8  1  1, 
               -7  1  1,   7  1  1,  -1  2  1,   0  2  1,   1  2  1,   7  2  1, 
                0  3  1,   1  3  1,  -7  4  1,   0  4  1,   1  4  1,  -7  5  1, 
                0  5  1,   1  5  1,   5  5  1,  -8  6  1,  -7  6  1,  -2  6  1, 
                1  6  1,   2  6  1,   4  6  1,  -7  8  1,  -1  8  1,  -5  9  1, 
               -1  9  1,   1 -9  2,   6 -9  2,  -1 -8  2,   8 -7  2,   7 -6  2, 
                8 -6  2,   7 -4  2,   8 -4  2,   9 -4  2,   5 -3  2,   6 -3  2, 
                7 -3  2,   8 -3  2,   6 -1  2,   7  0  2,  -1  1  2,   1  1  2, 
               -8  3  2,  -1  3  2,  -8  4  2,  -2  4  2,  -1  4  2,   1  4  2, 
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
2025-02-12
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   11.443(7)
_cell_length_b                   11.988(8)
_cell_length_c                   19.506(9)
_cell_angle_alpha                96.05(5)
_cell_angle_beta                 73.16(5)
_cell_angle_gamma                114.90(6)
_cell_volume                     2323(3)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    433
_cell_measurement_temperature    470.00(14)
_cell_measurement_theta_max      26.9960
_cell_measurement_theta_min      4.0450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.623
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.1219
_diffrn_reflns_Laue_measured_fraction_full 0.904
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4375
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        16.000
_diffrn_reflns_theta_max         38.129
_diffrn_reflns_theta_min         4.066
_diffrn_ambient_temperature      470
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.904
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                382
_reflns_number_total             2037
_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         0.221
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2037
_refine_ls_number_restraints     1119
_refine_ls_R_factor_all          0.4219
_refine_ls_R_factor_gt           0.1781
_refine_ls_restrained_S_all      0.951
_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          0.3891
_refine_ls_wR_factor_ref         0.5437
_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
 N2-C43 \\sim N1-C13 \\sim N3-C49
 with sigma of 0.02
 O3-C19 \\sim O4-C20 \\sim O1-C1 \\sim O2-C2 \\sim O6-C32 \\sim O5-C31
 with sigma of 0.02
 N3-C32 \\sim N3-C31 \\sim N2-C19 \\sim N2-C20 \\sim N1-C1 \\sim N1-C2
 with sigma of 0.02
 N1-C13 \\sim N2-C43 \\sim N3-C49
 with sigma of 0.02
 C24-C23 \\sim C19-C23 \\sim C20-C21 \\sim C22-C21 \\sim C23-C22 \\sim C30-C29
\\sim C21-C30 \\sim C22-C27
 \\sim C25-C24 \\sim C28-C27 \\sim C27-C26 \\sim C25-C26 \\sim C40-C28 \\sim
C38-C26 \\sim C37-C38 \\sim C39-
 C40 \\sim C38-C39 \\sim C41-C40 \\sim C41-C42 \\sim C42-C33 \\sim C33-C34
\\sim C34-C35 \\sim C35-C36 ~
 C36-C37 \\sim C34-C39 \\sim C31-C35 \\sim C32-C33 \\sim C9-C10 \\sim C8-C9
\\sim C7-C8 \\sim C6-C7 \\sim C5-C6
 \\sim C4-C5 \\sim C4-C9 \\sim C3-C4 \\sim C12-C3 \\sim C11-C12 \\sim C11-C10
\\sim C2-C3 \\sim C1-C5 \\sim C29-C28
 with sigma of 0.02
 C44-C43 \\sim C45-C44 \\sim C46-C45 \\sim C47-C46 \\sim C15-C14 \\sim C16-C15
\\sim C14-C13 \\sim C50-C49
 \\sim C51-C50 \\sim C52-C51 \\sim C53-C52
 with sigma of 0.02
 C53-C51 \\sim C52-C50 \\sim C51-C49 \\sim N3-C50 \\sim N2-C44 \\sim C45-C43
\\sim C46-C44 \\sim C47-C45 ~
 N1-C14 \\sim C15-C13 \\sim C16-C14
 with sigma of 0.02
 C33-C35 \\sim C31-C32 \\sim C23-C21 \\sim C20-C19 \\sim C3-C5 \\sim C1-C2
 with sigma of 0.02
 C17-C15 \\sim C18-C16
 with sigma of 0.02
 C17-C18 \\sim C17-C16 \\sim C16-C15
 with sigma of 0.02
 C54-C53 \\sim C53-C52 \\sim C52-C51
 with sigma of 0.02
 C53-C51 \\sim C52-C50 \\sim C54-C52
 with sigma of 0.02
 C46-C44 \\sim C47-C45 \\sim C48-C46
 with sigma of 0.02
 C47-C46 \\sim C48-C47 \\sim C46-C45 \\sim C45-C44
 with sigma of 0.02
 C1-C3 \\sim C2-C5 \\sim N1-C4 \\sim N2-C22 \\sim C20-C23 \\sim C19-C21 \\sim
C32-C35 \\sim N3-C34 \\sim C31-C33
 with sigma of 0.02
 C13-C15 \\sim C15-C17
 with sigma of 0.04
 C14-C16 \\sim C16-C18
 with sigma of 0.04
3. Restrained planarity
 C39, C34, C33, C42, C41, C40, C28, C27, C22, C23, C24, C25, C26, C38, C35, O3,
  C29, C30, C31, C43, O5, C32, N2, C36, O4, C20, O6, C19, N3, C21, C37, C49
 with sigma of 0.1
4.a Secondary CH2 refined with riding coordinates:
 C47(H34,H35), C13(H6,H5), C50(H41,H42), C14(H8,H7), C16(H12,H11), C52(H45,
 H46), C43(H26,H27), C15(H10,H9), C51(H43,H44), C44(H29,H28), C49(H40,H39),
 C45(H31,H30), C53(H48,H47), C46(H33,H32), C17(H14,H13)
4.b Aromatic/amide H refined with riding coordinates:
 C42(H25), C41(H24), C24(H18), C25(H19), C29(H20), C11(H3), C12(H4), C30(H21),
 C6(H1), C7(H2), C36(H22), C37(H23)
4.c Fitted hexagon refined as free rotating group:
 C39(C34,C33,C42,C41,C40), C27(C22,C23,C24,C25,C26), C10(C11,C12,C3,C4,C9)
4.d Idealised Me refined as rotating group:
 C18(H15,H17,H16), C54(H50,H54B,H49), C48(H37,H36,H51)
;
_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
C39 C 0.4179(17) 0.0837(13) 0.4647(13) 0.265(14) Uiso 1 1 d DG . . . .
C34 C 0.3479(18) 0.0018(14) 0.4199(8) 0.275(15) Uiso 1 1 d DG . . . .
C33 C 0.2087(18) -0.0522(12) 0.4410(9) 0.280(15) Uiso 1 1 d DG . . . .
C42 C 0.1397(17) -0.0243(18) 0.5069(10) 0.296(15) Uiso 1 1 d DG . . . .
H25 H 0.046585 -0.060382 0.521058 0.355 Uiso 1 1 calc R U . . .
C41 C 0.210(3) 0.0577(19) 0.5517(7) 0.278(15) Uiso 1 1 d DG . . . .
H24 H 0.163553 0.076333 0.595782 0.334 Uiso 1 1 calc R U . . .
C40 C 0.349(3) 0.1117(12) 0.5306(11) 0.280(15) Uiso 1 1 d DG . . . .
C28 C 0.410(2) 0.190(2) 0.5792(13) 0.271(15) Uiso 1 1 d D . . . .
C27 C 0.5496(18) 0.2584(17) 0.5650(14) 0.295(16) Uiso 1 1 d DG . . . .
C22 C 0.6179(19) 0.3375(18) 0.6114(9) 0.291(15) Uiso 1 1 d DG . . . .
C23 C 0.7570(19) 0.3882(17) 0.5925(11) 0.323(17) Uiso 1 1 d DG . . . .
C24 C 0.8278(18) 0.360(2) 0.5274(12) 0.290(15) Uiso 1 1 d DG . . . .
H18 H 0.920905 0.393818 0.514752 0.348 Uiso 1 1 calc R U . . .
C25 C 0.760(3) 0.281(2) 0.4810(9) 0.352(19) Uiso 1 1 d DG . . . .
H19 H 0.806869 0.261763 0.437424 0.422 Uiso 1 1 calc R U . . .
C26 C 0.620(3) 0.2300(17) 0.4999(12) 0.280(15) Uiso 1 1 d DG . . . .
C38 C 0.559(2) 0.152(2) 0.4513(15) 0.305(17) Uiso 1 1 d D . . . .
C35 C 0.422(3) -0.019(3) 0.3529(13) 0.330(18) Uiso 1 1 d D . . . .
O3 O 0.949(3) 0.521(3) 0.6286(13) 0.415(16) Uiso 1 1 d D . . . .
C47 C 1.092(5) 0.924(5) 0.855(3) 0.63(4) Uiso 1 1 d D . . . .
H34 H 1.104547 1.009252 0.863564 0.752 Uiso 1 1 calc R U . . .
H35 H 1.179643 0.922217 0.839974 0.752 Uiso 1 1 calc R U . . .
C13 C 0.462(4) 0.814(4) 0.8305(16) 0.42(2) Uiso 1 1 d D . . . .
H6 H 0.369085 0.800820 0.848643 0.504 Uiso 1 1 calc R U . . .
H5 H 0.516242 0.901744 0.828774 0.504 Uiso 1 1 calc R U . . .
O2 O 0.254(2) 0.668(3) 0.7891(13) 0.385(14) Uiso 1 1 d D . . . .
C29 C 0.347(3) 0.231(3) 0.6427(15) 0.300(17) Uiso 1 1 d D . . . .
H20 H 0.254848 0.201702 0.652440 0.360 Uiso 1 1 calc R U . . .
O1 O 0.701(2) 0.867(3) 0.7306(13) 0.385(15) Uiso 1 1 d D . . . .
C10 C 0.386(3) 0.4950(18) 0.5499(9) 0.248(14) Uiso 1 1 d DG . . . .
C11 C 0.261(2) 0.4787(17) 0.5957(14) 0.285(15) Uiso 1 1 d DG . . . .
H3 H 0.183857 0.427509 0.582766 0.342 Uiso 1 1 calc R U . . .
C12 C 0.2526(17) 0.5388(19) 0.6607(12) 0.288(15) Uiso 1 1 d DG . . . .
H4 H 0.169226 0.527851 0.691271 0.346 Uiso 1 1 calc R U . . .
C3 C 0.368(2) 0.6152(19) 0.6800(9) 0.38(2) Uiso 1 1 d DG . . . .
C4 C 0.4931(17) 0.6315(18) 0.6342(10) 0.278(15) Uiso 1 1 d DG . . . .
C9 C 0.502(2) 0.5714(19) 0.5692(9) 0.268(15) Uiso 1 1 d DG . . . .
C30 C 0.403(3) 0.308(3) 0.6937(17) 0.315(17) Uiso 1 1 d D . . . .
H21 H 0.350722 0.322592 0.736997 0.378 Uiso 1 1 calc R U . . .
C5 C 0.6124(18) 0.722(3) 0.6448(17) 0.317(18) Uiso 1 1 d D . . . .
C8 C 0.615(3) 0.578(3) 0.5131(13) 0.269(16) Uiso 1 1 d D . . . .
C50 C 0.123(4) -0.176(3) 0.2260(19) 0.48(3) Uiso 1 1 d D . . . .
H41 H 0.204309 -0.103349 0.207412 0.581 Uiso 1 1 calc R U . . .
H42 H 0.051717 -0.150190 0.248529 0.581 Uiso 1 1 calc R U . . .
C14 C 0.495(5) 0.756(4) 0.8797(16) 0.55(3) Uiso 1 1 d D . . . .
H8 H 0.428976 0.672316 0.889491 0.655 Uiso 1 1 calc R U . . .
H7 H 0.581559 0.754192 0.857283 0.655 Uiso 1 1 calc R U . . .
C16 C 0.463(4) 0.737(6) 1.005(2) 0.79(6) Uiso 1 1 d D . . . .
H12 H 0.386025 0.739985 1.041135 0.951 Uiso 1 1 calc R U . . .
H11 H 0.438954 0.653614 0.987490 0.951 Uiso 1 1 calc R U . . .
C52 C 0.002(7) -0.235(6) 0.138(3) 0.85(7) Uiso 1 1 d D . . . .
H45 H 0.053476 -0.164206 0.105043 1.016 Uiso 1 1 calc R U . . .
H46 H -0.061947 -0.214354 0.175719 1.016 Uiso 1 1 calc R U . . .
C31 C 0.356(4) -0.105(3) 0.3094(12) 0.327(19) Uiso 1 1 d D . . . .
C1 C 0.609(3) 0.781(3) 0.7092(19) 0.285(17) Uiso 1 1 d D . . . .
C2 C 0.363(3) 0.677(3) 0.7439(14) 0.34(2) Uiso 1 1 d D . . . .
C43 C 0.821(5) 0.567(3) 0.753(2) 0.50(3) Uiso 1 1 d D . . . .
H26 H 0.894880 0.543518 0.745413 0.602 Uiso 1 1 calc R U . . .
H27 H 0.762628 0.537197 0.800881 0.602 Uiso 1 1 calc R U . . .
C15 C 0.499(7) 0.820(4) 0.946(2) 0.73(5) Uiso 1 1 d D . . . .
H10 H 0.437748 0.859932 0.956195 0.879 Uiso 1 1 calc R U . . .
H9 H 0.588596 0.883583 0.941788 0.879 Uiso 1 1 calc R U . . .
O5 O 0.411(2) -0.136(2) 0.2483(11) 0.350(13) Uiso 1 1 d D . . . .
C6 C 0.730(3) 0.726(3) 0.5981(15) 0.286(16) Uiso 1 1 d D . . . .
H1 H 0.810943 0.770805 0.609030 0.344 Uiso 1 1 calc R U . . .
C32 C 0.141(2) -0.131(3) 0.3961(16) 0.35(2) Uiso 1 1 d D . . . .
C7 C 0.726(3) 0.663(3) 0.5344(15) 0.262(15) Uiso 1 1 d D . . . .
H2 H 0.808465 0.680131 0.501216 0.314 Uiso 1 1 calc R U . . .
C51 C 0.090(5) -0.257(5) 0.168(2) 0.66(5) Uiso 1 1 d D . . . .
H43 H 0.171473 -0.247007 0.130540 0.793 Uiso 1 1 calc R U . . .
H44 H 0.047735 -0.342031 0.185084 0.793 Uiso 1 1 calc R U . . .
C44 C 0.874(8) 0.699(3) 0.754(4) 0.83(7) Uiso 1 1 d D . . . .
H29 H 0.802458 0.724977 0.757520 0.997 Uiso 1 1 calc R U . . .
H28 H 0.940961 0.731478 0.708586 0.997 Uiso 1 1 calc R U . . .
N2 N 0.750(4) 0.507(3) 0.7042(17) 0.419(19) Uiso 1 1 d D . . . .
C36 C 0.562(3) 0.035(3) 0.3337(18) 0.35(2) Uiso 1 1 d D . . . .
H22 H 0.613809 0.019342 0.290622 0.420 Uiso 1 1 calc R U . . .
C49 C 0.144(4) -0.237(3) 0.2788(17) 0.38(2) Uiso 1 1 d D . . . .
H40 H 0.057481 -0.295742 0.305748 0.455 Uiso 1 1 calc R U . . .
H39 H 0.195406 -0.283394 0.253827 0.455 Uiso 1 1 calc R U . . .
O4 O 0.556(2) 0.493(2) 0.7779(12) 0.365(13) Uiso 1 1 d D . . . .
C45 C 0.933(5) 0.748(4) 0.813(2) 0.64(4) Uiso 1 1 d D . . . .
H31 H 0.863273 0.740280 0.856755 0.766 Uiso 1 1 calc R U . . .
H30 H 0.980986 0.700938 0.818989 0.766 Uiso 1 1 calc R U . . .
C53 C -0.071(6) -0.339(6) 0.099(4) 0.81(6) Uiso 1 1 d D . . . .
H48 H -0.149972 -0.394991 0.132898 0.973 Uiso 1 1 calc R U . . .
H47 H -0.099190 -0.310493 0.064933 0.973 Uiso 1 1 calc R U . . .
C20 C 0.605(4) 0.451(3) 0.7188(13) 0.282(16) Uiso 1 1 d D . . . .
O6 O 0.021(3) -0.183(3) 0.3960(12) 0.394(15) Uiso 1 1 d D . . . .
C19 C 0.822(3) 0.467(3) 0.6397(17) 0.35(2) Uiso 1 1 d D . . . .
N3 N 0.209(4) -0.160(2) 0.3267(15) 0.320(15) Uiso 1 1 d D . . . .
C46 C 1.025(8) 0.876(4) 0.799(3) 0.82(7) Uiso 1 1 d D . . . .
H33 H 1.091237 0.884270 0.753687 0.983 Uiso 1 1 calc R U . . .
H32 H 0.975989 0.923789 0.796319 0.983 Uiso 1 1 calc R U . . .
C21 C 0.541(2) 0.362(3) 0.6755(15) 0.360(19) Uiso 1 1 d D . . . .
N1 N 0.484(3) 0.768(3) 0.7608(14) 0.304(14) Uiso 1 1 d D . . . .
C37 C 0.615(3) 0.113(3) 0.3850(15) 0.267(15) Uiso 1 1 d D . . . .
H23 H 0.708333 0.145675 0.372672 0.320 Uiso 1 1 calc R U . . .
C17 C 0.573(6) 0.770(6) 1.036(4) 0.77(6) Uiso 1 1 d D . . . .
H14 H 0.575881 0.837814 1.068269 0.927 Uiso 1 1 calc R U . . .
H13 H 0.656881 0.797652 0.998056 0.927 Uiso 1 1 calc R U . . .
C18 C 0.558(12) 0.666(7) 1.074(7) 1.23(15) Uiso 1 1 d D . . . .
H15 H 0.584406 0.693167 1.117521 1.851 Uiso 1 1 calc R U . . .
H17 H 0.614147 0.627891 1.044662 1.851 Uiso 1 1 calc R U . . .
H16 H 0.466551 0.607402 1.085326 1.851 Uiso 1 1 calc R U . . .
C54 C 0.011(11) -0.403(8) 0.062(5) 1.04(11) Uiso 1 1 d D . . . .
H50 H 0.096699 -0.365992 0.072294 1.563 Uiso 1 1 calc R U . . .
H54B H 0.023871 -0.399108 0.011422 1.563 Uiso 1 1 calc R U . . .
H49 H -0.032584 -0.487971 0.077856 1.563 Uiso 1 1 calc R U . . .
C48 C 1.016(12) 0.854(12) 0.921(4) 1.5(2) Uiso 1 1 d D . . . .
H37 H 1.071938 0.828856 0.938241 2.232 Uiso 1 1 calc R U . . .
H36 H 0.941700 0.781924 0.912511 2.232 Uiso 1 1 calc R U . . .
H51 H 0.982368 0.903040 0.956400 2.232 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
C39 C34 1.3900 . ?
C39 C40 1.3900 . ?
C39 C38 1.423(14) . ?
C34 C33 1.3900 . ?
C34 C35 1.398(13) . ?
C33 C42 1.3900 . ?
C33 C32 1.365(14) . ?
C42 H25 0.9300 . ?
C42 C41 1.3900 . ?
C41 H24 0.9300 . ?
C41 C40 1.3900 . ?
C40 C28 1.383(14) . ?
C28 C27 1.410(14) . ?
C28 C29 1.394(14) . ?
C27 C22 1.3900 . ?
C27 C26 1.3900 . ?
C22 C23 1.3900 . ?
C22 C21 1.390(13) . ?
C23 C24 1.3900 . ?
C23 C19 1.382(14) . ?
C24 H18 0.9300 . ?
C24 C25 1.3900 . ?
C25 H19 0.9300 . ?
C25 C26 1.3900 . ?
C26 C38 1.385(14) . ?
C38 C37 1.398(14) . ?
C35 C31 1.378(14) . ?
C35 C36 1.393(14) . ?
O3 C19 1.279(18) . ?
C47 H34 0.9700 . ?
C47 H35 0.9700 . ?
C47 C46 1.45(3) . ?
C47 C48 1.44(3) . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.45(3) . ?
C13 N1 1.40(2) . ?
O2 C2 1.274(18) . ?
C29 H20 0.9300 . ?
C29 C30 1.389(14) . ?
O1 C1 1.263(18) . ?
C10 C11 1.3900 . ?
C10 C9 1.3900 . ?
C10 C8 1.43(3) 2_666 ?
C11 H3 0.9300 . ?
C11 C12 1.3900 . ?
C12 H4 0.9300 . ?
C12 C3 1.3900 . ?
C3 C4 1.3900 . ?
C3 C2 1.383(14) . ?
C4 C9 1.3900 . ?
C4 C5 1.396(13) . ?
C9 C8 1.412(14) . ?
C30 H21 0.9300 . ?
C30 C21 1.378(14) . ?
C5 C1 1.373(14) . ?
C5 C6 1.371(14) . ?
C8 C7 1.396(14) . ?
C50 H41 0.9700 . ?
C50 H42 0.9700 . ?
C50 C51 1.45(3) . ?
C50 C49 1.45(3) . ?
C14 H8 0.9700 . ?
C14 H7 0.9700 . ?
C14 C15 1.43(3) . ?
C16 H12 0.9700 . ?
C16 H11 0.9700 . ?
C16 C15 1.45(3) . ?
C16 C17 1.44(3) . ?
C52 H45 0.9700 . ?
C52 H46 0.9700 . ?
C52 C51 1.43(3) . ?
C52 C53 1.45(3) . ?
C31 O5 1.271(17) . ?
C31 N3 1.466(19) . ?
C1 N1 1.450(18) . ?
C2 N1 1.453(19) . ?
C43 H26 0.9700 . ?
C43 H27 0.9700 . ?
C43 C44 1.43(3) . ?
C43 N2 1.38(2) . ?
C15 H10 0.9700 . ?
C15 H9 0.9700 . ?
C6 H1 0.9300 . ?
C6 C7 1.387(14) . ?
C32 O6 1.256(18) . ?
C32 N3 1.439(18) . ?
C7 H2 0.9300 . ?
C51 H43 0.9700 . ?
C51 H44 0.9700 . ?
C44 H29 0.9700 . ?
C44 H28 0.9700 . ?
C44 C45 1.46(3) . ?
N2 C20 1.458(19) . ?
N2 C19 1.451(19) . ?
C36 H22 0.9300 . ?
C36 C37 1.388(14) . ?
C49 H40 0.9700 . ?
C49 H39 0.9700 . ?
C49 N3 1.39(2) . ?
O4 C20 1.276(18) . ?
C45 H31 0.9700 . ?
C45 H30 0.9700 . ?
C45 C46 1.45(3) . ?
C53 H48 0.9700 . ?
C53 H47 0.9700 . ?
C53 C54 1.45(3) . ?
C20 C21 1.375(14) . ?
C46 H33 0.9700 . ?
C46 H32 0.9700 . ?
C37 H23 0.9300 . ?
C17 H14 0.9700 . ?
C17 H13 0.9700 . ?
C17 C18 1.45(3) . ?
C18 H15 0.9653 . ?
C18 H17 0.9634 . ?
C18 H16 0.9663 . ?
C54 H50 1.1097 . ?
C54 H54B 1.0872 . ?
C54 H49 1.1298 . ?
C48 H37 1.0951 . ?
C48 H36 1.0834 . ?
C48 H51 1.0990 . ?

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
C34 C39 C40 120.0 . . ?
C34 C39 C38 128.2(19) . . ?
C40 C39 C38 111.8(19) . . ?
C39 C34 C35 117.5(15) . . ?
C33 C34 C39 120.0 . . ?
C33 C34 C35 122.4(15) . . ?
C42 C33 C34 120.0 . . ?
C32 C33 C34 119.3(12) . . ?
C32 C33 C42 120.7(12) . . ?
C33 C42 H25 120.0 . . ?
C33 C42 C41 120.0 . . ?
C41 C42 H25 120.0 . . ?
C42 C41 H24 120.0 . . ?
C40 C41 C42 120.0 . . ?
C40 C41 H24 120.0 . . ?
C41 C40 C39 120.0 . . ?
C28 C40 C39 124(2) . . ?
C28 C40 C41 116(2) . . ?
C40 C28 C27 124(2) . . ?
C40 C28 C29 127(3) . . ?
C29 C28 C27 109(2) . . ?
C22 C27 C28 127(2) . . ?
C22 C27 C26 120.0 . . ?
C26 C27 C28 113(2) . . ?
C27 C22 C21 116.9(15) . . ?
C23 C22 C27 120.0 . . ?
C23 C22 C21 123.1(15) . . ?
C22 C23 C24 120.0 . . ?
C19 C23 C22 118.6(12) . . ?
C19 C23 C24 121.4(12) . . ?
C23 C24 H18 120.0 . . ?
C25 C24 C23 120.0 . . ?
C25 C24 H18 120.0 . . ?
C24 C25 H19 120.0 . . ?
C24 C25 C26 120.0 . . ?
C26 C25 H19 120.0 . . ?
C25 C26 C27 120.0 . . ?
C38 C26 C27 123(2) . . ?
C38 C26 C25 117(2) . . ?
C26 C38 C39 124(2) . . ?
C26 C38 C37 130(2) . . ?
C37 C38 C39 106(2) . . ?
C31 C35 C34 118.6(12) . . ?
C31 C35 C36 120(2) . . ?
C36 C35 C34 121(3) . . ?
H34 C47 H35 108.0 . . ?
C46 C47 H34 108.7 . . ?
C46 C47 H35 110.0 . . ?
C46 C47 C48 111(3) . . ?
C48 C47 H34 109.9 . . ?
C48 C47 H35 109.0 . . ?
H6 C13 H5 107.7 . . ?
C14 C13 H6 108.8 . . ?
C14 C13 H5 109.1 . . ?
N1 C13 H6 108.8 . . ?
N1 C13 H5 108.9 . . ?
N1 C13 C14 113(2) . . ?
C28 C29 H20 115.3 . . ?
C30 C29 C28 129(3) . . ?
C30 C29 H20 115.3 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 C8 116(3) . 2_666 ?
C9 C10 C8 124(3) . 2_666 ?
C10 C11 H3 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H3 120.0 . . ?
C11 C12 H4 120.0 . . ?
C11 C12 C3 120.0 . . ?
C3 C12 H4 120.0 . . ?
C12 C3 C4 120.0 . . ?
C2 C3 C12 121.5(12) . . ?
C2 C3 C4 118.5(12) . . ?
C3 C4 C9 120.0 . . ?
C3 C4 C5 122.5(15) . . ?
C9 C4 C5 116.7(15) . . ?
C10 C9 C8 110(2) . . ?
C4 C9 C10 120.0 . . ?
C4 C9 C8 130(2) . . ?
C29 C30 H21 122.3 . . ?
C21 C30 C29 115(3) . . ?
C21 C30 H21 122.4 . . ?
C1 C5 C4 118.5(12) . . ?
C6 C5 C4 118(3) . . ?
C6 C5 C1 122(2) . . ?
C9 C8 C10 126(3) . 2_666 ?
C7 C8 C10 128(3) . 2_666 ?
C7 C8 C9 106(3) . . ?
H41 C50 H42 108.0 . . ?
C51 C50 H41 110.5 . . ?
C51 C50 H42 109.1 . . ?
C49 C50 H41 109.8 . . ?
C49 C50 H42 108.5 . . ?
C49 C50 C51 111(3) . . ?
C13 C14 H8 109.2 . . ?
C13 C14 H7 108.9 . . ?
H8 C14 H7 107.8 . . ?
C15 C14 C13 113(3) . . ?
C15 C14 H8 109.7 . . ?
C15 C14 H7 108.6 . . ?
H12 C16 H11 108.0 . . ?
C15 C16 H12 110.0 . . ?
C15 C16 H11 109.1 . . ?
C17 C16 H12 110.4 . . ?
C17 C16 H11 108.7 . . ?
C17 C16 C15 111(3) . . ?
H45 C52 H46 107.8 . . ?
C51 C52 H45 110.7 . . ?
C51 C52 H46 108.0 . . ?
C51 C52 C53 113(3) . . ?
C53 C52 H45 110.0 . . ?
C53 C52 H46 107.4 . . ?
C35 C31 N3 121.1(12) . . ?
O5 C31 C35 125(3) . . ?
O5 C31 N3 113(4) . . ?
O1 C1 C5 131(3) . . ?
O1 C1 N1 106(3) . . ?
C5 C1 N1 121.9(12) . . ?
O2 C2 C3 123(2) . . ?
O2 C2 N1 115(2) . . ?
C3 C2 N1 121.9(12) . . ?
H26 C43 H27 107.2 . . ?
C44 C43 H26 107.2 . . ?
C44 C43 H27 108.7 . . ?
N2 C43 H26 107.5 . . ?
N2 C43 H27 108.3 . . ?
N2 C43 C44 117(2) . . ?
C14 C15 C16 111(3) . . ?
C14 C15 H10 109.2 . . ?
C14 C15 H9 110.0 . . ?
C16 C15 H10 108.7 . . ?
C16 C15 H9 109.5 . . ?
H10 C15 H9 107.9 . . ?
C5 C6 H1 120.6 . . ?
C5 C6 C7 119(3) . . ?
C7 C6 H1 120.4 . . ?
C33 C32 N3 122.3(12) . . ?
O6 C32 C33 134(3) . . ?
O6 C32 N3 103(2) . . ?
C8 C7 H2 115.5 . . ?
C6 C7 C8 129(3) . . ?
C6 C7 H2 115.5 . . ?
C50 C51 H43 108.2 . . ?
C50 C51 H44 110.1 . . ?
C52 C51 C50 112(3) . . ?
C52 C51 H43 107.6 . . ?
C52 C51 H44 110.5 . . ?
H43 C51 H44 107.8 . . ?
C43 C44 H29 108.7 . . ?
C43 C44 H28 110.2 . . ?
C43 C44 C45 111(3) . . ?
H29 C44 H28 108.0 . . ?
C45 C44 H29 109.0 . . ?
C45 C44 H28 109.8 . . ?
C43 N2 C20 126(4) . . ?
C43 N2 C19 116(4) . . ?
C19 N2 C20 115.5(15) . . ?
C35 C36 H22 123.2 . . ?
C37 C36 C35 114(3) . . ?
C37 C36 H22 123.2 . . ?
C50 C49 H40 109.1 . . ?
C50 C49 H39 107.7 . . ?
H40 C49 H39 107.5 . . ?
N3 C49 C50 115(2) . . ?
N3 C49 H40 108.8 . . ?
N3 C49 H39 108.2 . . ?
C44 C45 H31 109.9 . . ?
C44 C45 H30 109.3 . . ?
H31 C45 H30 108.1 . . ?
C46 C45 C44 111(3) . . ?
C46 C45 H31 109.3 . . ?
C46 C45 H30 109.7 . . ?
C52 C53 H48 110.7 . . ?
C52 C53 H47 109.0 . . ?
H48 C53 H47 107.9 . . ?
C54 C53 C52 112(3) . . ?
C54 C53 H48 110.2 . . ?
C54 C53 H47 107.4 . . ?
O4 C20 N2 108(3) . . ?
O4 C20 C21 130(3) . . ?
C21 C20 N2 121.8(12) . . ?
C23 C19 N2 121.7(12) . . ?
O3 C19 C23 125(3) . . ?
O3 C19 N2 113(3) . . ?
C32 N3 C31 115.5(15) . . ?
C49 N3 C31 121(4) . . ?
C49 N3 C32 124(3) . . ?
C47 C46 C45 111(3) . . ?
C47 C46 H33 108.8 . . ?
C47 C46 H32 110.0 . . ?
C45 C46 H33 109.1 . . ?
C45 C46 H32 109.5 . . ?
H33 C46 H32 108.0 . . ?
C30 C21 C22 122(3) . . ?
C20 C21 C22 118.5(12) . . ?
C20 C21 C30 119(2) . . ?
C13 N1 C1 129(3) . . ?
C13 N1 C2 115(3) . . ?
C1 N1 C2 115.4(15) . . ?
C38 C37 H23 113.3 . . ?
C36 C37 C38 133(3) . . ?
C36 C37 H23 113.2 . . ?
C16 C17 H14 108.6 . . ?
C16 C17 H13 110.3 . . ?
C16 C17 C18 110(3) . . ?
H14 C17 H13 108.1 . . ?
C18 C17 H14 106.9 . . ?
C18 C17 H13 112.6 . . ?
C17 C18 H15 110.8 . . ?
C17 C18 H17 106.7 . . ?
C17 C18 H16 112.4 . . ?
H15 C18 H17 109.4 . . ?
H15 C18 H16 109.0 . . ?
H17 C18 H16 108.4 . . ?
C53 C54 H50 125.3 . . ?
C53 C54 H54B 122.7 . . ?
C53 C54 H49 127.4 . . ?
H50 C54 H54B 90.6 . . ?
H50 C54 H49 88.5 . . ?
H54B C54 H49 91.6 . . ?
C47 C48 H37 123.8 . . ?
C47 C48 H36 122.4 . . ?
C47 C48 H51 124.2 . . ?
H37 C48 H36 94.6 . . ?
H37 C48 H51 92.6 . . ?
H36 C48 H51 90.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C39 C34 C33 C42 0.0 . . . . ?
C39 C34 C33 C32 179.3(18) . . . . ?
C39 C34 C35 C31 176(3) . . . . ?
C39 C34 C35 C36 4(4) . . . . ?
C39 C40 C28 C27 5(3) . . . . ?
C39 C40 C28 C29 173(2) . . . . ?
C39 C38 C37 C36 6(5) . . . . ?
C34 C39 C40 C41 0.0 . . . . ?
C34 C39 C40 C28 178.6(15) . . . . ?
C34 C39 C38 C26 -178.7(19) . . . . ?
C34 C39 C38 C37 -4(3) . . . . ?
C34 C33 C42 C41 0.0 . . . . ?
C34 C33 C32 O6 -171(4) . . . . ?
C34 C33 C32 N3 -1(4) . . . . ?
C34 C35 C31 O5 -178(3) . . . . ?
C34 C35 C31 N3 10(5) . . . . ?
C34 C35 C36 C37 -4(5) . . . . ?
C33 C34 C35 C31 -7(4) . . . . ?
C33 C34 C35 C36 -179(3) . . . . ?
C33 C42 C41 C40 0.0 . . . . ?
C33 C32 N3 C31 4(5) . . . . ?
C33 C32 N3 C49 -178(2) . . . . ?
C42 C33 C32 O6 8(6) . . . . ?
C42 C33 C32 N3 178(2) . . . . ?
C42 C41 C40 C39 0.0 . . . . ?
C42 C41 C40 C28 -178.7(14) . . . . ?
C41 C40 C28 C27 -175.9(19) . . . . ?
C41 C40 C28 C29 -8(4) . . . . ?
C40 C39 C34 C33 0.0 . . . . ?
C40 C39 C34 C35 177.2(17) . . . . ?
C40 C39 C38 C26 4(3) . . . . ?
C40 C39 C38 C37 178.4(18) . . . . ?
C40 C28 C27 C22 -179.3(15) . . . . ?
C40 C28 C27 C26 -6(3) . . . . ?
C40 C28 C29 C30 180(3) . . . . ?
C28 C27 C22 C23 173(2) . . . . ?
C28 C27 C22 C21 -7(3) . . . . ?
C28 C27 C26 C25 -173.8(19) . . . . ?
C28 C27 C26 C38 6(2) . . . . ?
C28 C29 C30 C21 7(6) . . . . ?
C27 C28 C29 C30 -11(5) . . . . ?
C27 C22 C23 C24 0.0 . . . . ?
C27 C22 C23 C19 180(2) . . . . ?
C27 C22 C21 C30 2(4) . . . . ?
C27 C22 C21 C20 -172(3) . . . . ?
C27 C26 C38 C39 -6(4) . . . . ?
C27 C26 C38 C37 -179(3) . . . . ?
C22 C27 C26 C25 0.0 . . . . ?
C22 C27 C26 C38 180(2) . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C22 C23 C19 O3 -179(3) . . . . ?
C22 C23 C19 N2 -6(4) . . . . ?
C23 C22 C21 C30 -178(3) . . . . ?
C23 C22 C21 C20 7(5) . . . . ?
C23 C24 C25 C26 0.0 . . . . ?
C24 C23 C19 O3 1(5) . . . . ?
C24 C23 C19 N2 173(2) . . . . ?
C24 C25 C26 C27 0.0 . . . . ?
C24 C25 C26 C38 -180(2) . . . . ?
C25 C26 C38 C39 174.2(18) . . . . ?
C25 C26 C38 C37 1(4) . . . . ?
C26 C27 C22 C23 0.0 . . . . ?
C26 C27 C22 C21 180(2) . . . . ?
C26 C38 C37 C36 180(3) . . . . ?
C38 C39 C34 C33 -177.0(17) . . . . ?
C38 C39 C34 C35 0(2) . . . . ?
C38 C39 C40 C41 177.5(15) . . . . ?
C38 C39 C40 C28 -4(2) . . . . ?
C35 C34 C33 C42 -177.0(18) . . . . ?
C35 C34 C33 C32 2(3) . . . . ?
C35 C31 N3 C32 -9(5) . . . . ?
C35 C31 N3 C49 173(3) . . . . ?
C35 C36 C37 C38 -2(6) . . . . ?
C13 C14 C15 C16 150(4) . . . . ?
O2 C2 N1 C13 12(6) . . . . ?
O2 C2 N1 C1 -179(3) . . . . ?
C29 C28 C27 C22 11(3) . . . . ?
C29 C28 C27 C26 -176(2) . . . . ?
C29 C30 C21 C22 -2(5) . . . . ?
C29 C30 C21 C20 173(3) . . . . ?
O1 C1 N1 C13 -17(6) . . . . ?
O1 C1 N1 C2 177(3) . . . . ?
C10 C11 C12 C3 0.0 . . . . ?
C10 C9 C8 C10 -8(4) . . . 2_666 ?
C10 C9 C8 C7 176(2) . . . . ?
C10 C8 C7 C6 -173(3) 2_666 . . . ?
C11 C10 C9 C4 0.0 . . . . ?
C11 C10 C9 C8 -177.1(19) . . . . ?
C11 C12 C3 C4 0.0 . . . . ?
C11 C12 C3 C2 179(3) . . . . ?
C12 C3 C4 C9 0.0 . . . . ?
C12 C3 C4 C5 169(3) . . . . ?
C12 C3 C2 O2 1(6) . . . . ?
C12 C3 C2 N1 -173(3) . . . . ?
C3 C4 C9 C10 0.0 . . . . ?
C3 C4 C9 C8 176(2) . . . . ?
C3 C4 C5 C1 13(5) . . . . ?
C3 C4 C5 C6 177(3) . . . . ?
C3 C2 N1 C13 -174(3) . . . . ?
C3 C2 N1 C1 -5(6) . . . . ?
C4 C3 C2 O2 180(3) . . . . ?
C4 C3 C2 N1 7(5) . . . . ?
C4 C9 C8 C10 175(2) . . . 2_666 ?
C4 C9 C8 C7 -1(4) . . . . ?
C4 C5 C1 O1 -177(4) . . . . ?
C4 C5 C1 N1 -11(7) . . . . ?
C4 C5 C6 C7 15(6) . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C9 C4 C5 C1 -178(3) . . . . ?
C9 C4 C5 C6 -13(5) . . . . ?
C9 C8 C7 C6 3(6) . . . . ?
C5 C4 C9 C10 -170(3) . . . . ?
C5 C4 C9 C8 7(3) . . . . ?
C5 C1 N1 C13 174(3) . . . . ?
C5 C1 N1 C2 8(6) . . . . ?
C5 C6 C7 C8 -10(7) . . . . ?
C8 C10 C11 C12 175(2) 2_666 . . . ?
C8 C10 C9 C4 -175(2) 2_666 . . . ?
C8 C10 C9 C8 8(3) 2_666 . . . ?
C50 C49 N3 C31 -88(5) . . . . ?
C50 C49 N3 C32 94(5) . . . . ?
C14 C13 N1 C1 -67(7) . . . . ?
C14 C13 N1 C2 100(5) . . . . ?
C31 C35 C36 C37 -175(3) . . . . ?
C1 C5 C6 C7 179(4) . . . . ?
C2 C3 C4 C9 -179(3) . . . . ?
C2 C3 C4 C5 -10(3) . . . . ?
C43 C44 C45 C46 160(8) . . . . ?
C43 N2 C20 O4 16(5) . . . . ?
C43 N2 C20 C21 -159(3) . . . . ?
C43 N2 C19 C23 169(3) . . . . ?
C43 N2 C19 O3 -18(5) . . . . ?
C15 C16 C17 C18 -159(10) . . . . ?
O5 C31 N3 C32 179(3) . . . . ?
O5 C31 N3 C49 0(5) . . . . ?
C6 C5 C1 O1 19(9) . . . . ?
C6 C5 C1 N1 -175(3) . . . . ?
C32 C33 C42 C41 -179.3(19) . . . . ?
C51 C50 C49 N3 164(4) . . . . ?
C51 C52 C53 C54 -36(11) . . . . ?
C44 C43 N2 C20 -99(7) . . . . ?
C44 C43 N2 C19 100(7) . . . . ?
C44 C45 C46 C47 -176(7) . . . . ?
N2 C43 C44 C45 174(5) . . . . ?
N2 C20 C21 C22 -9(6) . . . . ?
N2 C20 C21 C30 177(3) . . . . ?
C36 C35 C31 O5 -6(7) . . . . ?
C36 C35 C31 N3 -178(3) . . . . ?
C49 C50 C51 C52 148(6) . . . . ?
O4 C20 C21 C22 177(3) . . . . ?
O4 C20 C21 C30 3(7) . . . . ?
C53 C52 C51 C50 -159(7) . . . . ?
C20 N2 C19 C23 5(5) . . . . ?
C20 N2 C19 O3 179(3) . . . . ?
O6 C32 N3 C31 177(3) . . . . ?
O6 C32 N3 C49 -5(5) . . . . ?
C19 C23 C24 C25 -180(3) . . . . ?
C19 N2 C20 O4 178(3) . . . . ?
C19 N2 C20 C21 2(6) . . . . ?
C21 C22 C23 C24 -180(2) . . . . ?
C21 C22 C23 C19 0(3) . . . . ?
N1 C13 C14 C15 168(4) . . . . ?
C17 C16 C15 C14 118(6) . . . . ?
C48 C47 C46 C45 -23(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_C6_0_5GPa
_database_code_depnum_ccdc_archive 'CCDC 2412019'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C6_0_5GPa       
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.315 Why?    
RESPONSE: These data come from a high-pressure experiment and part of the 
reflections could not be collected due to the limited DAC opening angle and the 
measurement strategy.
;
_vrf_PLAT088_PDI_C6_0_5GPa       
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.84 Note 
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber. 
;
_vrf_PLAT911_PDI_C6_0_5GPa       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600       1171 Report
                1  1  0,   0  2  0,   0  3  0,  -1  4  0,  -2  5  0,   1  5  0, 
               -1  6  0,   1  6  0,  -1  7  0,  -2  8  0,  -1  8  0,   3  8  0, 
               -2  9  0,  -1  9  0,   0 10  0,   0-10  1,   1 -9  1,   2 -9  1, 
               -3 -8  1,   2 -8  1,   3 -7  1,   0 -6  1,  -4 -5  1,  -1 -5  1, 
                0 -5  1,   3 -5  1,   0 -4  1,   1 -4  1,   0 -3  1,   0 -2  1, 
                1  1  1,   0  2  1,   0  3  1,  -2  4  1,  -1  4  1,   0  4  1, 
               -1  5  1,   0  5  1,  -1  6  1,  -1  7  1,  -3  8  1,  -2  8  1, 
               -1  8  1,   0  8  1,  -2  9  1,  -1  9  1,   0  9  1,   0 10  1, 
                0 -9  2,   1 -9  2,  -3 -8  2,  -1 -8  2,   0 -8  2,   1 -8  2, 
               -1 -7  2,   0 -7  2,   1 -7  2,   3 -7  2,  -3 -6  2,  -1 -6  2, 
                0 -6  2,   1 -6  2,  -1 -5  2,   0 -5  2,   1 -5  2,   3 -5  2, 
               -1 -4  2,   0 -4  2,   1 -4  2,  -1 -3  2,   0 -3  2,   1 -3  2, 
               -1 -2  2,   0 -2  2,   1 -2  2,  -1 -1  2,   1 -1  2,   1  1  2, 
                0  2  2,   1  2  2,  -1  3  2,   0  3  2,  -1  4  2,   0  4  2, 
               -1  5  2,   0  5  2,  -1  6  2,   0  6  2,  -2  7  2,  -1  7  2, 
                0  7  2,  -3  8  2,  -2  8  2,  -1  8  2,   0  8  2,   1  8  2, 
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-06-07
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   4.64520(10)
_cell_length_b                   8.5703(3)
_cell_length_c                   17.076(2)
_cell_angle_alpha                80.961(6)
_cell_angle_beta                 85.933(4)
_cell_angle_gamma                84.011(2)
_cell_volume                     666.68(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2743
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3820
_cell_measurement_theta_min      3.1180
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.047
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75164
_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    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_preparation       'mounted in a diamond-anvil cell'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.315
_diffrn_reflns_Laue_measured_fraction_max 0.175
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6772
_diffrn_reflns_point_group_measured_fraction_full 0.315
_diffrn_reflns_point_group_measured_fraction_max 0.175
_diffrn_reflns_theta_full        17.160
_diffrn_reflns_theta_max         25.473
_diffrn_reflns_theta_min         3.055
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.315
_diffrn_measured_fraction_theta_max 0.175
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ     18.00  96.00   0.20    0.50  57.05   0.00-134.76    --   390
  2  φ     18.00  96.00   0.20    0.50  57.05   0.00-134.76    --   390
  3  φ     18.00  96.00   0.20    0.50  57.05   0.00-134.76    --   390
  4  φ     18.00  96.00   0.20    0.50  57.05   0.00-134.76    --   390
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.49173
_diffrn_source                   synchrotron
_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                1116
_reflns_number_total             1306
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.069
_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)+(0.1600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1754
_refine_ls_wR_factor_ref         0.1832
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C15(H9,H10), C14(H7,H8), C13(H5,H6), C17(H14,H13), C16(H12,H11)
1.b Aromatic/amide H refined with riding coordinates:
 C12(H4), C11(H3), C7(H2), C6(H1)
1.c Idealised Me refined as rotating group:
 C18(H16,H17,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
O2 O -0.02725(18) 0.42544(14) 0.61868(17) 0.0516(17) Uani 1 1 d . . . . .
N1 N 0.1070(2) 0.21879(19) 0.7134(2) 0.044(2) Uani 1 1 d . . . . .
C15 C -0.2035(2) 0.50151(18) 0.8570(2) 0.052(2) Uani 1 1 d . . . . .
H9 H -0.293511 0.427923 0.898152 0.062 Uiso 1 1 calc R U . . .
H10 H -0.353194 0.553364 0.822387 0.062 Uiso 1 1 calc R U . . .
C14 C 0.0226(2) 0.40970(19) 0.8092(2) 0.055(2) Uani 1 1 d . . . . .
H7 H 0.171215 0.356980 0.843936 0.066 Uiso 1 1 calc R U . . .
H8 H 0.113899 0.483395 0.768394 0.066 Uiso 1 1 calc R U . . .
C12 C 0.3955(2) 0.3245(2) 0.5063(3) 0.036(2) Uani 1 1 d . . . . .
H4 H 0.268236 0.412862 0.490002 0.043 Uiso 1 1 calc R U . . .
C11 C 0.6175(2) 0.27480(16) 0.4523(2) 0.0410(18) Uani 1 1 d . . . . .
H3 H 0.637048 0.331107 0.401310 0.049 Uiso 1 1 calc R U . . .
C10 C 0.8087(2) 0.14022(18) 0.4757(2) 0.0327(18) Uani 1 1 d . . . . .
C2 C 0.1338(2) 0.3034(2) 0.6386(3) 0.040(2) Uani 1 1 d . . . . .
C18 C -0.1686(5) 0.8398(3) 0.9843(3) 0.077(4) Uani 1 1 d . . . . .
H16 H -0.307922 0.879467 1.022351 0.116 Uiso 1 1 calc R U . . .
H17 H -0.116460 0.925888 0.944474 0.116 Uiso 1 1 calc R U . . .
H15 H 0.001161 0.790878 1.010604 0.116 Uiso 1 1 calc R U . . .
C9 C 0.7756(2) 0.05503(18) 0.5530(2) 0.034(2) Uani 1 1 d . . . . .
C4 C 0.5506(2) 0.10779(19) 0.6081(2) 0.0353(19) Uani 1 1 d . . . . .
C8 C 0.9593(2) -0.0858(2) 0.5804(3) 0.038(2) Uani 1 1 d . . . . .
C5 C 0.5134(3) 0.0254(2) 0.6838(3) 0.037(2) Uani 1 1 d . . . . .
C3 C 0.3631(2) 0.2464(2) 0.5815(3) 0.036(2) Uani 1 1 d . . . . .
C13 C -0.1061(2) 0.28557(18) 0.7701(2) 0.044(2) Uani 1 1 d . . . . .
H5 H -0.166218 0.200996 0.810683 0.053 Uiso 1 1 calc R U . . .
H6 H -0.275976 0.334342 0.742545 0.053 Uiso 1 1 calc R U . . .
C7 C 0.9117(3) -0.1646(2) 0.6550(3) 0.046(2) Uani 1 1 d . . . . .
H2 H 1.028497 -0.257334 0.671237 0.055 Uiso 1 1 calc R U . . .
C17 C -0.2996(3) 0.7176(2) 0.9452(3) 0.056(2) Uani 1 1 d . . . . .
H14 H -0.450778 0.771228 0.911567 0.067 Uiso 1 1 calc R U . . .
H13 H -0.388589 0.643077 0.986096 0.067 Uiso 1 1 calc R U . . .
C16 C -0.0765(2) 0.62565(18) 0.8951(2) 0.050(2) Uani 1 1 d . . . . .
H12 H 0.010087 0.700156 0.853688 0.060 Uiso 1 1 calc R U . . .
H11 H 0.076478 0.573753 0.928556 0.060 Uiso 1 1 calc R U . . .
C6 C 0.6917(3) -0.1114(2) 0.7089(2) 0.049(2) Uani 1 1 d . . . . .
H1 H 0.666905 -0.166542 0.760020 0.059 Uiso 1 1 calc R U . . .
O1 O 0.2520(3) 0.0162(2) 0.8095(3) 0.060(3) Uani 1 1 d . . . . .
C1 C 0.2854(3) 0.0817(2) 0.7413(3) 0.039(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.237(2) . ?
N1 C2 1.370(5) . ?
N1 C13 1.471(3) . ?
N1 C1 1.404(3) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C14 1.515(3) . ?
C15 C16 1.519(2) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C13 1.532(2) . ?
C12 H4 0.9300 . ?
C12 C11 1.412(4) . ?
C12 C3 1.358(6) . ?
C11 H3 0.9300 . ?
C11 C10 1.404(3) . ?
C10 C9 1.411(6) . ?
C10 C8 1.479(4) 2_756 ?
C2 C3 1.489(4) . ?
C18 H16 0.9600 . ?
C18 H17 0.9600 . ?
C18 H15 0.9600 . ?
C18 C17 1.524(3) . ?
C9 C4 1.440(4) . ?
C9 C8 1.438(3) . ?
C4 C5 1.382(6) . ?
C4 C3 1.431(3) . ?
C8 C7 1.360(6) . ?
C5 C6 1.390(3) . ?
C5 C1 1.487(5) . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C7 H2 0.9300 . ?
C7 C6 1.415(4) . ?
C17 H14 0.9700 . ?
C17 H13 0.9700 . ?
C17 C16 1.530(3) . ?
C16 H12 0.9700 . ?
C16 H11 0.9700 . ?
C6 H1 0.9300 . ?
O1 C1 1.219(7) . ?

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 117.09(17) . . ?
C2 N1 C1 124.5(3) . . ?
C1 N1 C13 118.1(4) . . ?
H9 C15 H10 107.8 . . ?
C14 C15 H9 109.1 . . ?
C14 C15 H10 109.1 . . ?
C14 C15 C16 112.55(11) . . ?
C16 C15 H9 109.1 . . ?
C16 C15 H10 109.1 . . ?
C15 C14 H7 109.1 . . ?
C15 C14 H8 109.1 . . ?
C15 C14 C13 112.56(11) . . ?
H7 C14 H8 107.8 . . ?
C13 C14 H7 109.1 . . ?
C13 C14 H8 109.1 . . ?
C11 C12 H4 119.2 . . ?
C3 C12 H4 119.2 . . ?
C3 C12 C11 121.67(18) . . ?
C12 C11 H3 120.1 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H3 120.1 . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 C8 120.5(4) . 2_756 ?
C9 C10 C8 119.9(2) . 2_756 ?
O2 C2 N1 121.0(3) . . ?
O2 C2 C3 120.3(4) . . ?
N1 C2 C3 118.7(2) . . ?
H16 C18 H17 109.5 . . ?
H16 C18 H15 109.5 . . ?
H17 C18 H15 109.5 . . ?
C17 C18 H16 109.5 . . ?
C17 C18 H17 109.5 . . ?
C17 C18 H15 109.5 . . ?
C10 C9 C4 120.2(2) . . ?
C10 C9 C8 122.6(3) . . ?
C8 C9 C4 117.3(4) . . ?
C5 C4 C9 121.0(2) . . ?
C5 C4 C3 120.9(3) . . ?
C3 C4 C9 118.1(4) . . ?
C9 C8 C10 117.5(4) . 2_756 ?
C7 C8 C10 122.8(2) . 2_756 ?
C7 C8 C9 119.7(3) . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 C1 121.1(2) . . ?
C6 C5 C1 118.1(4) . . ?
C12 C3 C2 121.0(2) . . ?
C12 C3 C4 120.6(3) . . ?
C4 C3 C2 118.4(4) . . ?
N1 C13 C14 110.96(13) . . ?
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 . . ?
C8 C7 H2 118.7 . . ?
C8 C7 C6 122.7(2) . . ?
C6 C7 H2 118.7 . . ?
C18 C17 H14 109.0 . . ?
C18 C17 H13 109.0 . . ?
C18 C17 C16 113.05(15) . . ?
H14 C17 H13 107.8 . . ?
C16 C17 H14 109.0 . . ?
C16 C17 H13 109.0 . . ?
C15 C16 C17 113.54(12) . . ?
C15 C16 H12 108.9 . . ?
C15 C16 H11 108.9 . . ?
C17 C16 H12 108.9 . . ?
C17 C16 H11 108.9 . . ?
H12 C16 H11 107.7 . . ?
C5 C6 C7 118.4(4) . . ?
C5 C6 H1 120.8 . . ?
C7 C6 H1 120.8 . . ?
N1 C1 C5 116.5(4) . . ?
O1 C1 N1 120.3(3) . . ?
O1 C1 C5 123.3(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
O2 C2 C3 C12 -1.5(3) . . . . ?
O2 C2 C3 C4 177.93(12) . . . . ?
N1 C2 C3 C12 178.87(16) . . . . ?
N1 C2 C3 C4 -1.7(3) . . . . ?
C15 C14 C13 N1 170.1(2) . . . . ?
C14 C15 C16 C17 -178.7(2) . . . . ?
C12 C11 C10 C9 0.5(2) . . . . ?
C12 C11 C10 C8 179.45(12) . . . 2_756 ?
C11 C12 C3 C2 177.97(10) . . . . ?
C11 C12 C3 C4 -1.5(3) . . . . ?
C11 C10 C9 C4 -1.3(3) . . . . ?
C11 C10 C9 C8 178.57(10) . . . . ?
C10 C9 C4 C5 179.52(13) . . . . ?
C10 C9 C4 C3 0.7(3) . . . . ?
C10 C9 C8 C10 0.4(3) . . . 2_756 ?
C10 C9 C8 C7 -178.44(15) . . . . ?
C10 C8 C7 C6 179.24(12) 2_756 . . . ?
C2 N1 C13 C14 -83.1(3) . . . . ?
C2 N1 C1 C5 -1.3(3) . . . . ?
C2 N1 C1 O1 177.8(2) . . . . ?
C18 C17 C16 C15 179.0(3) . . . . ?
C9 C4 C5 C6 -0.2(3) . . . . ?
C9 C4 C5 C1 178.64(13) . . . . ?
C9 C4 C3 C12 0.7(3) . . . . ?
C9 C4 C3 C2 -178.81(11) . . . . ?
C9 C8 C7 C6 -2.0(3) . . . . ?
C4 C9 C8 C10 -179.76(10) . . . 2_756 ?
C4 C9 C8 C7 1.4(3) . . . . ?
C4 C5 C6 C7 -0.3(3) . . . . ?
C4 C5 C1 N1 2.0(3) . . . . ?
C4 C5 C1 O1 -177.2(2) . . . . ?
C8 C10 C9 C4 179.76(10) 2_756 . . . ?
C8 C10 C9 C8 -0.4(3) 2_756 . . . ?
C8 C9 C4 C5 -0.3(3) . . . . ?
C8 C9 C4 C3 -179.13(11) . . . . ?
C8 C7 C6 C5 1.4(3) . . . . ?
C5 C4 C3 C12 -178.16(15) . . . . ?
C5 C4 C3 C2 2.4(3) . . . . ?
C3 C12 C11 C10 0.9(3) . . . . ?
C3 C4 C5 C6 178.55(12) . . . . ?
C3 C4 C5 C1 -2.6(3) . . . . ?
C13 N1 C2 O2 -4.3(3) . . . . ?
C13 N1 C2 C3 175.26(10) . . . . ?
C13 N1 C1 C5 -175.31(13) . . . . ?
C13 N1 C1 O1 3.9(3) . . . . ?
C16 C15 C14 C13 -179.4(3) . . . . ?
C6 C5 C1 N1 -179.11(13) . . . . ?
C6 C5 C1 O1 1.7(4) . . . . ?
C1 N1 C2 O2 -178.35(13) . . . . ?
C1 N1 C2 C3 1.2(3) . . . . ?
C1 N1 C13 C14 91.3(2) . . . . ?
C1 C5 C6 C7 -179.17(15) . . . . ?

_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_C6_2_41GPa
_database_code_depnum_ccdc_archive 'CCDC 2412026'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PDI_C6_2_41GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      15.00 Degree 
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle. 
;
_vrf_PLAT029_PDI_C6_2_41GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.356 Why?  
RESPONSE: These data come from a high-pressure experiment and part of the 
reflections could not be collected due to the limited DAC opening angle and the 
measurement strategy.
;
_vrf_PLAT088_PDI_C6_2_41GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.57 Note   
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber. 
;
_vrf_PLAT340_PDI_C6_2_41GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.04316 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_C6_2_41GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        270 Report
               -2  2  0,  -2  8  0,   1 -4  1,   5 -2  1,  -2 -1  1,   5 -1  1, 
                5  0  1,   2  1  1,   5  1  1,  -2  2  1,  -1  4  1,   4  4  1, 
               -2  5  1,   2  5  1,   4  5  1,   3  6  1,   3  7  1,   2  8  1, 
                0 10  1,   4 -7  2,   5 -4  2,   5 -3  2,   5 -2  2,  -2 -1  2, 
                1 -1  2,   4 -1  2,   5 -1  2,   1  0  2,   4  0  2,   5  0  2, 
                1  1  2,   4  1  2,   5  1  2,   0  2  2,   1  2  2,   3  2  2, 
                4  2  2,   3  3  2,   4  3  2,   0  4  2,   3  4  2,   4  4  2, 
                2  5  2,   3  5  2,   4  5  2,   2  6  2,   3  6  2,   1  7  2, 
                2  7  2,   3  7  2,   1  8  2,   2  8  2,   0  9  2,   1  9  2, 
               -1 10  2,   0 10  2,   3 -9  3,   3 -8  3,   3 -7  3,   4 -7  3, 
                3 -6  3,   4 -6  3,   3 -5  3,   4 -5  3,   3 -4  3,   4 -4  3, 
                0 -3  3,   1 -3  3,   2 -3  3,   3 -3  3,   4 -3  3,   5 -3  3, 
                0 -2  3,   1 -2  3,   2 -2  3,   3 -2  3,   4 -2  3,   5 -2  3, 
               -1 -1  3,   1 -1  3,   2 -1  3,   3 -1  3,   4 -1  3,   5 -1  3, 
               -1  0  3,   1  0  3,   2  0  3,   3  0  3,   4  0  3,   5  0  3, 
               -1  1  3,   1  1  3,   2  1  3,   3  1  3,   4  1  3,   5  1  3, 
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-06-07
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   4.4179(4)
_cell_length_b                   8.5938(6)
_cell_length_c                   15.738(6)
_cell_angle_alpha                90.801(18)
_cell_angle_beta                 92.621(19)
_cell_angle_gamma                97.410(7)
_cell_volume                     591.8(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    802
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7060
_cell_measurement_theta_min      4.6430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.451
_exptl_absorpt_correction_T_min  0.348
_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    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 2 2 0.0580
1 12 -1 0.1222
-6 0 0 0.0506
0 0 -22 0.0131
6 0 -2 0.0709
0 0 22 0.0131
-1 -12 1 0.1333

_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.037
_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)      0.397     0.453
         range of gasket transmission (min-max)           0.840     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 = 205.0 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  0.0860
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.356
_diffrn_reflns_Laue_measured_fraction_max 0.219
_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       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            4347
_diffrn_reflns_point_group_measured_fraction_full 0.356
_diffrn_reflns_point_group_measured_fraction_max 0.219
_diffrn_reflns_theta_full        15.000
_diffrn_reflns_theta_max         25.626
_diffrn_reflns_theta_min         4.658
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.356
_diffrn_measured_fraction_theta_max 0.219
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00 -21.00   0.75   17.50    --  -29.94  77.00 150.00   48
  2  ω    -19.00  44.00   0.75   17.50    --  -29.94 -39.00-167.00   84
  3  ω    -89.00 -26.00   0.75   17.50    --  -29.94 135.00 123.00   84
  4  ω     13.00  40.00   0.75   17.50    --  -29.94-114.00-135.00   36
  5  ω    -44.00  19.00   0.75   17.50    --  -29.94  19.00-180.00   84
  6  ω    -31.00   0.50   0.75   17.50    --  -29.94   0.00   0.00   42
  7  ω     13.00  40.00   0.75   17.50    --  -29.94-114.00  45.00   36
  8  ω    -55.00   8.00   0.75   17.50    --  -29.94  67.00 -23.00   84
  9  ω    -19.00  44.00   0.75   17.50    --  -29.94 -39.00  12.00   84
 10  ω    -31.00   0.50   0.75   17.50    --   30.41   0.00-150.00   42
 11  ω    -31.00   0.50   0.75   17.50    --   30.41   0.00  30.00   42
 12  ω      8.00  32.00   0.75   17.50    --  -29.94 -99.00-150.00   32
 13  ω    -19.00   5.00   0.75   17.50    --  -29.94 -57.00  30.00   32
 14  ω    -19.00  14.00   0.75   17.50    --  -29.94 -19.00-150.00   44
 15  ω    -40.00 -13.00   0.75   17.50    --   30.41 114.00 135.00   36
 16  ω      1.75  49.00   0.75   17.50    --   30.41 -53.00  17.00   63
 17  ω    -16.00   8.00   0.75   17.50    --   30.41  67.00 157.00   32
 18  ω     20.00  56.00   0.75   17.50    --   30.41 -77.00-150.00   48
 19  ω     31.00  76.00   0.75   17.50    --   30.41-125.00  60.00   60
 20  ω     -5.00  19.00   0.75   17.50    --   30.41  57.00 -30.00   32
 21  ω    -44.00  19.00   0.75   17.50    --  -29.94  39.00 -12.00   84
 22  ω    -44.00  19.00   0.75   17.50    --  -29.94  19.00-180.00   84
 23  ω    -19.00  44.00   0.75   17.50    --  -29.94 -19.00-180.00   84
 24  ω    -19.00  44.00   0.75   17.50    --  -29.94 -39.00  12.00   84
 25  ω    -22.25  40.00   0.75   17.50    --  -29.94 -26.00   7.00   83
 26  ω    -26.25  36.00   0.75   17.50    --  -29.94 -13.00   3.00   83
 27  ω    -36.00  27.00   0.75   17.50    --  -29.94  13.00  -3.00   84
 28  ω    -40.00  23.00   0.75   17.50    --  -29.94  26.00  -7.00   84
 29  ω     -8.00  52.00   0.75   17.50    --  -29.94 -37.00-180.00   80
 30  ω    -49.00  14.00   0.75   17.50    --  -29.94  53.00 -17.00   84
;
_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 2.41(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                278
_reflns_number_total             490
_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         0.129
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         490
_refine_ls_number_restraints     276
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.0730
_refine_ls_restrained_S_all      0.817
_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)+(0.1311P)²+2.5333P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1953
_refine_ls_wR_factor_ref         0.2615
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C1-N1 \\sim C2-C3 \\sim C4-C5
 with sigma of 0.02
 C4-C3 \\sim C12-C11 \\sim C10-C9
 with sigma of 0.02
 C13-C14 \\sim C15-C16 \\sim C17-C18
 with sigma of 0.02
2. Rigid bond restraints
 C1, C3, C2, C5, N1, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim N1 \\sim C2 \\sim C4 \\sim C5 \\sim C3: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
Uanis(C9) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N1) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
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 0.1 and
sigma for terminal atoms of 0.2
Uanis(O2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C1, C3, C2, C5, N1, C4, C9, C8, C10, C7, O1, C12, O2, C6, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C14, C18, C13, C15, C17, C16
 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:
 C14(H14A,H14B), C17(H17A,H17B), C15(H15A,H15B), C13(H13A,H13B), C16(H16A,H16B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C7(H7), C6(H6)
5.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 1.046(2) 0.4470(10) 0.364(2) 0.039(8) Uani 1 1 d . U . . .
O1 O 0.712(3) 0.0593(12) 0.177(3) 0.039(5) Uani 1 1 d . . . . .
N1 N 0.884(2) 0.2538(11) 0.277(3) 0.029(5) Uani 1 1 d D U . . .
C2 C 0.878(3) 0.3327(17) 0.353(3) 0.029(6) Uani 1 1 d D U . . .
C12 C 0.624(3) 0.3341(14) 0.483(3) 0.027(6) Uani 1 1 d D . . . .
H12 H 0.759012 0.423484 0.498358 0.032 Uiso 1 1 calc R U . . .
C11 C 0.401(3) 0.2748(13) 0.541(3) 0.037(7) Uani 1 1 d D . . . .
H11 H 0.392684 0.327736 0.592610 0.045 Uiso 1 1 calc R U . . .
C14 C 0.965(3) 0.4194(14) 0.143(3) 0.05(2) Uani 1 1 d D U . . .
H14A H 0.789542 0.358130 0.114053 0.058 Uiso 1 1 calc R U . . .
H14B H 1.112749 0.451012 0.100881 0.058 Uiso 1 1 calc R U . . .
C17 C 0.922(3) 0.7509(17) 0.057(3) 0.04(2) Uani 1 1 d D U . . .
H17A H 1.075637 0.826290 0.085934 0.053 Uiso 1 1 calc R U . . .
H17B H 1.025900 0.673853 0.028395 0.053 Uiso 1 1 calc R U . . .
C4 C 0.444(3) 0.1259(15) 0.384(3) 0.031(5) Uani 1 1 d D U . . .
C10 C 0.196(3) 0.1421(15) 0.524(2) 0.026(6) Uani 1 1 d D . . . .
C5 C 0.457(3) 0.0531(16) 0.301(3) 0.031(5) Uani 1 1 d D U . . .
C15 C 0.863(3) 0.5670(14) 0.183(3) 0.061(18) Uani 1 1 d D U . . .
H15A H 0.718895 0.534731 0.226546 0.074 Uiso 1 1 calc R U . . .
H15B H 1.039250 0.628504 0.211558 0.074 Uiso 1 1 calc R U . . .
C7 C 0.051(4) -0.1401(17) 0.340(4) 0.038(7) Uani 1 1 d . . . . .
H7 H -0.079621 -0.229309 0.322196 0.045 Uiso 1 1 calc R U . . .
C13 C 1.104(3) 0.3188(16) 0.207(3) 0.04(2) Uani 1 1 d D U . . .
H13A H 1.282360 0.379552 0.234435 0.046 Uiso 1 1 calc R U . . .
H13B H 1.171600 0.230918 0.177110 0.046 Uiso 1 1 calc R U . . .
C16 C 0.717(3) 0.6692(15) 0.122(3) 0.06(2) Uani 1 1 d D U . . .
H16A H 0.632276 0.748805 0.154420 0.076 Uiso 1 1 calc R U . . .
H16B H 0.547577 0.605453 0.091799 0.076 Uiso 1 1 calc R U . . .
C3 C 0.642(3) 0.2633(13) 0.408(3) 0.028(6) Uani 1 1 d D U . . .
C9 C 0.222(3) 0.0675(14) 0.444(2) 0.023(5) Uani 1 1 d D U . . .
C8 C 0.019(3) -0.0729(15) 0.421(4) 0.030(7) Uani 1 1 d . . . . .
C18 C 0.746(4) 0.8343(17) -0.008(3) 0.06(2) Uani 1 1 d D U . . .
H18A H 0.875641 0.867051 -0.053981 0.087 Uiso 1 1 calc R U . . .
H18B H 0.678016 0.924620 0.017481 0.087 Uiso 1 1 calc R U . . .
H18C H 0.572220 0.764523 -0.030641 0.087 Uiso 1 1 calc R U . . .
C1 C 0.687(3) 0.1171(16) 0.244(4) 0.026(5) Uani 1 1 d D U . . .
C6 C 0.266(3) -0.0778(14) 0.288(3) 0.032(5) Uani 1 1 d . U . . .
H6 H 0.282854 -0.132901 0.237541 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.16(2) . ?
O1 C1 1.18(7) . ?
N1 C2 1.37(6) . ?
N1 C13 1.56(4) . ?
N1 C1 1.44(3) . ?
C2 C3 1.46(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.42(3) . ?
C12 C3 1.33(7) . ?
C11 H11 0.9300 . ?
C11 C10 1.38(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.54(4) . ?
C14 C13 1.50(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C16 1.52(4) . ?
C17 C18 1.51(3) . ?
C4 C5 1.44(3) . ?
C4 C3 1.42(2) . ?
C4 C9 1.44(3) . ?
C10 C9 1.42(3) . ?
C10 C8 1.40(4) 2_556 ?
C5 C1 1.44(4) . ?
C5 C6 1.32(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.49(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.41(8) . ?
C7 C6 1.35(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C9 C8 1.44(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C6 H6 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 N1 C13 120.9(15) . . ?
C2 N1 C1 129(3) . . ?
C1 N1 C13 110(3) . . ?
O2 C2 N1 117(3) . . ?
O2 C2 C3 128(3) . . ?
N1 C2 C3 114.2(18) . . ?
C11 C12 H12 119.6 . . ?
C3 C12 H12 119.6 . . ?
C3 C12 C11 120.9(17) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 C12 123(3) . . ?
C10 C11 H11 118.6 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C13 C14 C15 113(3) . . ?
H17A C17 H17B 107.9 . . ?
C16 C17 H17A 109.1 . . ?
C16 C17 H17B 109.1 . . ?
C18 C17 H17A 109.1 . . ?
C18 C17 H17B 109.1 . . ?
C18 C17 C16 112.4(15) . . ?
C3 C4 C5 121(2) . . ?
C3 C4 C9 117(3) . . ?
C9 C4 C5 122.3(17) . . ?
C11 C10 C9 115(2) . . ?
C11 C10 C8 126(3) . 2_556 ?
C8 C10 C9 119(2) 2_556 . ?
C1 C5 C4 119(2) . . ?
C6 C5 C4 114(3) . . ?
C6 C5 C1 126(3) . . ?
C14 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 115(3) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121(2) . . ?
N1 C13 H13A 108.7 . . ?
N1 C13 H13B 108.7 . . ?
C14 C13 N1 114.3(14) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C17 C16 H16A 108.2 . . ?
C17 C16 H16B 108.2 . . ?
C15 C16 C17 116.5(14) . . ?
C15 C16 H16A 108.2 . . ?
C15 C16 H16B 108.2 . . ?
H16A C16 H16B 107.3 . . ?
C12 C3 C2 117.3(18) . . ?
C12 C3 C4 121(2) . . ?
C4 C3 C2 121(3) . . ?
C10 C9 C4 123.0(18) . . ?
C10 C9 C8 119(3) . . ?
C8 C9 C4 118(3) . . ?
C10 C8 C7 121(2) 2_556 . ?
C10 C8 C9 122(4) 2_556 . ?
C7 C8 C9 117(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C1 N1 123(3) . . ?
O1 C1 C5 121.7(19) . . ?
N1 C1 C5 115(3) . . ?
C5 C6 C7 127(4) . . ?
C5 C6 H6 116.4 . . ?
C7 C6 H6 116.4 . . ?

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
O2 C2 C3 C12 -4(4) . . . . ?
O2 C2 C3 C4 177(3) . . . . ?
N1 C2 C3 C12 180(3) . . . . ?
N1 C2 C3 C4 0(3) . . . . ?
C2 N1 C13 C14 -93(3) . . . . ?
C2 N1 C1 O1 179(3) . . . . ?
C2 N1 C1 C5 -1(4) . . . . ?
C12 C11 C10 C9 0(2) . . . . ?
C12 C11 C10 C8 177(2) . . . 2_556 ?
C11 C12 C3 C2 179.7(17) . . . . ?
C11 C12 C3 C4 -1(4) . . . . ?
C11 C10 C9 C4 -1(2) . . . . ?
C11 C10 C9 C8 179(2) . . . . ?
C14 C15 C16 C17 -67(3) . . . . ?
C4 C5 C1 O1 178(3) . . . . ?
C4 C5 C1 N1 -1(2) . . . . ?
C4 C5 C6 C7 6(3) . . . . ?
C4 C9 C8 C10 177.4(18) . . . 2_556 ?
C4 C9 C8 C7 -1(4) . . . . ?
C10 C9 C8 C10 -3(3) . . . 2_556 ?
C10 C9 C8 C7 179(2) . . . . ?
C5 C4 C3 C2 -3(3) . . . . ?
C5 C4 C3 C12 178(2) . . . . ?
C5 C4 C9 C10 -176.8(16) . . . . ?
C5 C4 C9 C8 3(3) . . . . ?
C15 C14 C13 N1 61(2) . . . . ?
C13 N1 C2 O2 -2(4) . . . . ?
C13 N1 C2 C3 175.3(15) . . . . ?
C13 N1 C1 O1 5(4) . . . . ?
C13 N1 C1 C5 -175.5(17) . . . . ?
C13 C14 C15 C16 -178.8(10) . . . . ?
C3 C12 C11 C10 1(3) . . . . ?
C3 C4 C5 C1 3(2) . . . . ?
C3 C4 C5 C6 177.5(18) . . . . ?
C3 C4 C9 C10 1(2) . . . . ?
C3 C4 C9 C8 -179(2) . . . . ?
C9 C4 C5 C1 -179.4(17) . . . . ?
C9 C4 C5 C6 -5(2) . . . . ?
C9 C4 C3 C2 179.6(19) . . . . ?
C9 C4 C3 C12 0(3) . . . . ?
C8 C10 C9 C4 -177.5(18) 2_556 . . . ?
C8 C10 C9 C8 3(3) 2_556 . . . ?
C8 C7 C6 C5 -4(4) . . . . ?
C18 C17 C16 C15 172.8(16) . . . . ?
C1 N1 C2 O2 -175.2(19) . . . . ?
C1 N1 C2 C3 2(4) . . . . ?
C1 N1 C13 C14 82(2) . . . . ?
C1 C5 C6 C7 180(2) . . . . ?
C6 C5 C1 O1 4(4) . . . . ?
C6 C5 C1 N1 -175(2) . . . . ?
C6 C7 C8 C10 -177.0(18) . . . 2_556 ?
C6 C7 C8 C9 2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PDI_C6_1_95GPa
_database_code_depnum_ccdc_archive 'CCDC 2412024'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C6_1_95GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.321 Why?  
RESPONSE: These data come from a high-pressure experiment and part of the 
reflections could not be collected due to the limited DAC opening angle and the 
measurement strategy.
;
_vrf_PLAT088_PDI_C6_1_95GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.26 Note   
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber. 
;
_vrf_PLAT911_PDI_C6_1_95GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        666 Report
                1  0  0,   2  0  0,   3  0  0,   4  0  0,   5  0  0,  -5  1  0, 
               -4  1  0,   1  1  0,   2  1  0,   3  1  0,   4  1  0,   5  1  0, 
               -5  2  0,   3  2  0,   4  2  0,   5  2  0,   4  3  0,   4  4  0, 
                3  5  0,   4  5  0,  -4 -5  1,  -4 -4  1,  -4 -3  1,  -3 -3  1, 
               -5 -2  1,  -4 -2  1,  -3 -2  1,  -5 -1  1,  -4 -1  1,  -3 -1  1, 
               -2 -1  1,  -1 -1  1,   3 -1  1,   4 -1  1,   5 -1  1,  -5  0  1, 
               -4  0  1,  -3  0  1,  -2  0  1,  -1  0  1,   1  0  1,   4  0  1, 
                5  0  1,  -5  1  1,  -4  1  1,   1  1  1,   2  1  1,   3  1  1, 
                4  1  1,   5  1  1,  -5  2  1,   3  2  1,   4  2  1,   5  2  1, 
                4  3  1,   4  4  1,   3  5  1,   4  5  1,  -4 -5  2,  -4 -4  2, 
               -4 -3  2,  -3 -3  2,  -5 -2  2,  -4 -2  2,  -3 -2  2,  -2 -2  2, 
               -5 -1  2,  -4 -1  2,  -3 -1  2,  -2 -1  2,  -1 -1  2,   0 -1  2, 
                1 -1  2,   3 -1  2,   4 -1  2,   5 -1  2,  -5  0  2,  -4  0  2, 
               -3  0  2,  -1  0  2,   0  0  2,   1  0  2,   2  0  2,   4  0  2, 
                5  0  2,  -5  1  2,  -1  1  2,   0  1  2,   1  1  2,   2  1  2, 
                3  1  2,   4  1  2,   5  1  2,  -5  2  2,   0  2  2,   1  2  2, 
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-06-07
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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 0.0007 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                   4.46430(10)
_cell_length_b                   8.61510(10)
_cell_length_c                   15.8664(8)
_cell_angle_alpha                90.750(3)
_cell_angle_beta                 92.236(3)
_cell_angle_gamma                97.4900(10)
_cell_volume                     604.46(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1486
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.9320
_cell_measurement_theta_min      1.8620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.052
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93170
_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_colour_primary    red
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_preparation       'mounted in a diamond-anvil cell'
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.068
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.321
_diffrn_reflns_Laue_measured_fraction_max 0.199
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3501
_diffrn_reflns_point_group_measured_fraction_full 0.321
_diffrn_reflns_point_group_measured_fraction_max 0.199
_diffrn_reflns_theta_full        17.156
_diffrn_reflns_theta_max         24.435
_diffrn_reflns_theta_min         1.649
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.321
_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  φ     19.00  96.00   0.20    0.40  57.05   0.00-134.76    --   385
  2  φ     19.00  96.00   0.20    0.40  57.05   0.00-134.76    --   385
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.49163
_diffrn_source                   synchrotron
_diffrn_special_details          
'Data were collected at room temperature and pressure of 1.95(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                1022
_reflns_number_total             1202
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.24(5)
_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   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         1202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.068
_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)+(0.1151P)²+0.0295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1520
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H4(0.047) H3(0.047) H7(0.053) H8(0.053) H13(0.061) H14(0.061)
 H10(0.055) H9(0.055) H2(0.048) H5(0.053) H6(0.053) H11(0.069) H12(0.069)
 H1(0.052) H16(0.095) H17(0.095) H15(0.095)
 Fixed X: H4(0.753278) H3(0.396127) H7(0.779137) H8(1.10007) H13(1.022681)
 H14(1.076107) H10(1.043792) H9(0.726013) H2(-0.077147) H5(1.176364)
 H6(1.265433) H11(0.5528) H12(0.625444) H1(0.275353) H16(0.890363)
 H17(0.651197) H15(0.604001)
 Fixed Y: H4(0.423945) H3(0.324659) H7(0.35967) H8(0.448784) H13(0.670881)
 H14(0.822655) H10(0.631575) H9(0.541242) H2(-0.232487) H5(0.234722)
 H6(0.382795) H11(0.60266) H12(0.749188) H1(-0.126458) H16(0.884832)
 H17(0.91127) H15(0.76072)
 Fixed Z: H4(0.500548) H3(0.595623) H7(0.120665) H8(0.104103) H13(0.029237)
 H14(0.086435) H10(0.212307) H9(0.231132) H2(0.325941) H5(0.183614)
 H6(0.242316) H11(0.091644) H12(0.151745) H1(0.231748) H16(-0.04602)
 H17(0.020694) H15(-0.037368)
;
_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 1.0456(3) 0.44888(11) 0.3686(2) 0.051(2) Uani 1 1 d . . . . .
O1 O 0.7045(3) 0.06248(14) 0.1780(3) 0.047(2) Uani 1 1 d . . . . .
N1 N 0.8779(3) 0.25470(13) 0.2734(2) 0.035(2) Uani 1 1 d . . . . .
C2 C 0.8681(3) 0.33001(15) 0.3502(3) 0.036(2) Uani 1 1 d . . . . .
C12 C 0.6208(3) 0.33432(14) 0.4860(3) 0.039(2) Uani 1 1 d . . . . .
H4 H 0.753278 0.423945 0.500548 0.047 Uiso 1 1 calc R U . . .
C11 C 0.4050(3) 0.27475(14) 0.5436(3) 0.039(2) Uani 1 1 d . . . . .
H3 H 0.396127 0.324659 0.595623 0.047 Uiso 1 1 calc R U . . .
C14 C 0.9565(4) 0.42039(14) 0.1474(3) 0.044(2) Uani 1 1 d . . . . .
H7 H 0.779137 0.359670 0.120665 0.053 Uiso 1 1 calc R U . . .
H8 H 1.100070 0.448784 0.104103 0.053 Uiso 1 1 calc R U . . .
C17 C 0.9221(4) 0.74876(17) 0.0576(3) 0.051(3) Uani 1 1 d . . . . .
H13 H 1.022681 0.670881 0.029237 0.061 Uiso 1 1 calc R U . . .
H14 H 1.076107 0.822655 0.086435 0.061 Uiso 1 1 calc R U . . .
C4 C 0.4393(3) 0.12737(13) 0.3863(3) 0.030(2) Uani 1 1 d . . . . .
C10 C 0.2029(3) 0.13953(13) 0.5224(3) 0.032(2) Uani 1 1 d . . . . .
C5 C 0.4609(3) 0.05559(14) 0.3079(3) 0.039(2) Uani 1 1 d . . . . .
C15 C 0.8655(4) 0.56960(15) 0.1868(3) 0.046(2) Uani 1 1 d . . . . .
H10 H 1.043792 0.631575 0.212307 0.055 Uiso 1 1 calc R U . . .
H9 H 0.726013 0.541242 0.231132 0.055 Uiso 1 1 calc R U . . .
C7 C 0.0504(4) -0.14154(15) 0.3413(3) 0.040(3) Uani 1 1 d . . . . .
H2 H -0.077147 -0.232487 0.325941 0.048 Uiso 1 1 calc R U . . .
C13 C 1.0975(4) 0.31980(15) 0.2124(3) 0.044(2) Uani 1 1 d . . . . .
H5 H 1.176364 0.234722 0.183614 0.053 Uiso 1 1 calc R U . . .
H6 H 1.265433 0.382795 0.242316 0.053 Uiso 1 1 calc R U . . .
C16 C 0.7154(4) 0.66939(18) 0.1216(3) 0.058(2) Uani 1 1 d . . . . .
H11 H 0.552800 0.602660 0.091644 0.069 Uiso 1 1 calc R U . . .
H12 H 0.625444 0.749188 0.151745 0.069 Uiso 1 1 calc R U . . .
C3 C 0.6403(3) 0.26472(15) 0.4102(3) 0.031(2) Uani 1 1 d . . . . .
C9 C 0.2210(3) 0.06504(14) 0.4440(3) 0.033(2) Uani 1 1 d . . . . .
C8 C 0.0221(3) -0.07439(13) 0.4179(3) 0.033(2) Uani 1 1 d . . . . .
C6 C 0.2643(4) -0.07908(14) 0.2843(3) 0.043(2) Uani 1 1 d . . . . .
H1 H 0.275353 -0.126458 0.231748 0.052 Uiso 1 1 calc R U . . .
C18 C 0.7513(5) 0.83419(19) -0.0072(4) 0.064(3) Uani 1 1 d . . . . .
H16 H 0.890363 0.884832 -0.046020 0.095 Uiso 1 1 calc R U . . .
H17 H 0.651197 0.911270 0.020694 0.095 Uiso 1 1 calc R U . . .
H15 H 0.604001 0.760720 -0.037368 0.095 Uiso 1 1 calc R U . . .
C1 C 0.6836(3) 0.11963(17) 0.2477(3) 0.034(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.235(2) . ?
O1 C1 1.217(7) . ?
N1 C2 1.377(6) . ?
N1 C13 1.469(4) . ?
N1 C1 1.404(3) . ?
C2 C3 1.482(4) . ?
C12 H4 0.9300 . ?
C12 C11 1.407(4) . ?
C12 C3 1.348(6) . ?
C11 H3 0.9300 . ?
C11 C10 1.406(3) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C15 1.531(3) . ?
C14 C13 1.525(4) . ?
C17 H13 0.9700 . ?
C17 H14 0.9700 . ?
C17 C16 1.509(4) . ?
C17 C18 1.511(5) . ?
C4 C5 1.393(7) . ?
C4 C3 1.426(3) . ?
C4 C9 1.422(5) . ?
C10 C9 1.402(7) . ?
C10 C8 1.471(4) 2_556 ?
C5 C6 1.398(3) . ?
C5 C1 1.466(5) . ?
C15 H10 0.9700 . ?
C15 H9 0.9700 . ?
C15 C16 1.542(4) . ?
C7 H2 0.9300 . ?
C7 C8 1.357(7) . ?
C7 C6 1.401(4) . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C9 C8 1.443(3) . ?
C6 H1 0.9300 . ?
C18 H16 0.9600 . ?
C18 H17 0.9600 . ?
C18 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
C2 N1 C13 119.19(17) . . ?
C2 N1 C1 124.1(3) . . ?
C1 N1 C13 116.6(3) . . ?
O2 C2 N1 120.7(3) . . ?
O2 C2 C3 120.8(4) . . ?
N1 C2 C3 118.45(18) . . ?
C11 C12 H4 119.2 . . ?
C3 C12 H4 119.2 . . ?
C3 C12 C11 121.64(18) . . ?
C12 C11 H3 120.1 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H3 120.1 . . ?
H7 C14 H8 107.9 . . ?
C15 C14 H7 109.1 . . ?
C15 C14 H8 109.1 . . ?
C13 C14 H7 109.1 . . ?
C13 C14 H8 109.1 . . ?
C13 C14 C15 112.3(3) . . ?
H13 C17 H14 107.9 . . ?
C16 C17 H13 109.2 . . ?
C16 C17 H14 109.2 . . ?
C16 C17 C18 111.86(18) . . ?
C18 C17 H13 109.2 . . ?
C18 C17 H14 109.2 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 C9 121.1(2) . . ?
C9 C4 C3 118.8(4) . . ?
C11 C10 C8 120.6(4) . 2_556 ?
C9 C10 C11 119.4(3) . . ?
C9 C10 C8 119.99(19) . 2_556 ?
C4 C5 C6 120.2(3) . . ?
C4 C5 C1 121.5(2) . . ?
C6 C5 C1 118.3(4) . . ?
C14 C15 H10 109.1 . . ?
C14 C15 H9 109.1 . . ?
C14 C15 C16 112.4(3) . . ?
H10 C15 H9 107.9 . . ?
C16 C15 H10 109.1 . . ?
C16 C15 H9 109.1 . . ?
C8 C7 H2 118.7 . . ?
C8 C7 C6 122.51(19) . . ?
C6 C7 H2 118.7 . . ?
N1 C13 C14 111.93(15) . . ?
N1 C13 H5 109.2 . . ?
N1 C13 H6 109.2 . . ?
C14 C13 H5 109.2 . . ?
C14 C13 H6 109.2 . . ?
H5 C13 H6 107.9 . . ?
C17 C16 C15 115.68(16) . . ?
C17 C16 H11 108.4 . . ?
C17 C16 H12 108.4 . . ?
C15 C16 H11 108.4 . . ?
C15 C16 H12 108.4 . . ?
H11 C16 H12 107.4 . . ?
C12 C3 C2 120.76(19) . . ?
C12 C3 C4 120.3(3) . . ?
C4 C3 C2 119.0(4) . . ?
C4 C9 C8 117.4(4) . . ?
C10 C9 C4 120.1(2) . . ?
C10 C9 C8 122.5(3) . . ?
C7 C8 C10 122.6(2) . 2_556 ?
C7 C8 C9 119.9(3) . . ?
C9 C8 C10 117.5(4) . 2_556 ?
C5 C6 C7 118.9(4) . . ?
C5 C6 H1 120.5 . . ?
C7 C6 H1 120.5 . . ?
C17 C18 H16 109.5 . . ?
C17 C18 H17 109.5 . . ?
C17 C18 H15 109.5 . . ?
H16 C18 H17 109.5 . . ?
H16 C18 H15 109.5 . . ?
H17 C18 H15 109.5 . . ?
O1 C1 N1 119.7(3) . . ?
O1 C1 C5 123.4(2) . . ?
N1 C1 C5 116.9(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
O2 C2 C3 C12 0.4(4) . . . . ?
O2 C2 C3 C4 179.90(18) . . . . ?
N1 C2 C3 C12 -179.79(19) . . . . ?
N1 C2 C3 C4 -0.3(3) . . . . ?
C2 N1 C13 C14 -96.8(3) . . . . ?
C2 N1 C1 O1 178.6(2) . . . . ?
C2 N1 C1 C5 -0.9(3) . . . . ?
C12 C11 C10 C9 0.5(3) . . . . ?
C12 C11 C10 C8 179.32(16) . . . 2_556 ?
C11 C12 C3 C2 179.61(14) . . . . ?
C11 C12 C3 C4 0.2(4) . . . . ?
C11 C10 C9 C4 -0.9(4) . . . . ?
C11 C10 C9 C8 179.78(16) . . . . ?
C14 C15 C16 C17 -70.0(3) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C4 C5 C1 O1 -178.2(2) . . . . ?
C4 C5 C1 N1 1.3(4) . . . . ?
C4 C9 C8 C10 179.70(13) . . . 2_556 ?
C4 C9 C8 C7 0.7(4) . . . . ?
C10 C9 C8 C10 -0.9(4) . . . 2_556 ?
C10 C9 C8 C7 -179.9(2) . . . . ?
C5 C4 C3 C2 0.7(4) . . . . ?
C5 C4 C3 C12 -179.8(2) . . . . ?
C5 C4 C9 C10 -179.81(18) . . . . ?
C5 C4 C9 C8 -0.4(4) . . . . ?
C15 C14 C13 N1 66.7(2) . . . . ?
C13 N1 C2 O2 -1.6(3) . . . . ?
C13 N1 C2 C3 178.60(14) . . . . ?
C13 N1 C1 O1 0.4(3) . . . . ?
C13 N1 C1 C5 -179.09(17) . . . . ?
C13 C14 C15 C16 -178.54(13) . . . . ?
C3 C12 C11 C10 -0.1(3) . . . . ?
C3 C4 C5 C6 179.95(17) . . . . ?
C3 C4 C5 C1 -1.2(4) . . . . ?
C3 C4 C9 C10 0.9(4) . . . . ?
C3 C4 C9 C8 -179.74(16) . . . . ?
C9 C4 C5 C6 0.6(4) . . . . ?
C9 C4 C5 C1 179.51(16) . . . . ?
C9 C4 C3 C2 -179.99(16) . . . . ?
C9 C4 C3 C12 -0.5(4) . . . . ?
C8 C10 C9 C4 -179.70(13) 2_556 . . . ?
C8 C10 C9 C8 1.0(4) 2_556 . . . ?
C8 C7 C6 C5 1.4(4) . . . . ?
C6 C5 C1 O1 0.7(4) . . . . ?
C6 C5 C1 N1 -179.85(17) . . . . ?
C6 C7 C8 C10 179.83(16) . . . 2_556 ?
C6 C7 C8 C9 -1.2(4) . . . . ?
C18 C17 C16 C15 175.9(3) . . . . ?
C1 N1 C2 O2 -179.75(18) . . . . ?
C1 N1 C2 C3 0.5(4) . . . . ?
C1 N1 C13 C14 81.5(2) . . . . ?
C1 C5 C6 C7 179.99(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
;
####################################################################### 
# 
# 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_C6_2_05GPa
_database_code_depnum_ccdc_archive 'CCDC 2412025'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_PDI_C6_2_05GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.321 Why?  
RESPONSE: These data come from a high-pressure experiment and part of the 
reflections could not be collected due to the limited DAC opening angle and the 
measurement strategy.
;
_vrf_PLAT088_PDI_C6_2_05GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.30 Note   
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber. 
;
_vrf_PLAT911_PDI_C6_2_05GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        919 Report
               -1  1  0,  -1  2  0,  -2  3  0,  -5  4  0,  -4  4  0,  -3  4  0, 
               -2  4  0,  -4  5  0,  -3  5  0,  -2  5  0,  -4  6  0,  -3  6  0, 
               -4  7  0,  -3  7  0,  -3  8  0,  -3  9  0,   3 -9  1,   3 -8  1, 
                3 -7  1,   4 -7  1,   3 -6  1,   4 -6  1,   2 -5  1,   3 -5  1, 
                4 -5  1,   2 -4  1,   3 -4  1,   5 -4  1,   2 -3  1,   4 -3  1, 
                1 -2  1,   1 -1  1,   2 -1  1,  -1  1  1,   0  1  1,  -3  2  1, 
               -1  2  1,  -2  3  1,  -5  4  1,  -4  4  1,  -3  4  1,  -2  4  1, 
               -4  5  1,  -3  5  1,  -2  5  1,  -4  6  1,  -3  6  1,  -4  7  1, 
               -3  7  1,  -3  8  1,  -3  9  1,   2 -9  2,   3 -9  2,   3 -8  2, 
                3 -7  2,   4 -7  2,   3 -6  2,   4 -6  2,   3 -5  2,   4 -5  2, 
                2 -4  2,   3 -4  2,   2 -3  2,   1 -2  2,   2 -2  2,   0 -1  2, 
                1 -1  2,   1  0  2,   2  0  2,  -1  1  2,   0  1  2,   1  1  2, 
               -3  2  2,  -1  2  2,   0  2  2,   3  2  2,  -4  3  2,  -1  3  2, 
               -5  4  2,  -3  4  2,  -2  4  2,  -4  5  2,  -3  5  2,  -4  6  2, 
               -3  6  2,  -4  7  2,  -3  7  2,  -3  8  2,  -3  9  2,  -1  9  2, 
                2 -9  3,   3 -9  3,   3 -8  3,   2 -7  3,   3 -7  3,   4 -7  3, 
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-06-07
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   4.45490(10)
_cell_length_b                   8.60030(10)
_cell_length_c                   15.8585(8)
_cell_angle_alpha                90.799(2)
_cell_angle_beta                 92.222(2)
_cell_angle_gamma                97.4430(10)
_cell_volume                     601.91(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3164
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3690
_cell_measurement_theta_min      1.8620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.052
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76840
_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    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_preparation       'mounted in a diamond-anvil cell'
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.068
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.321
_diffrn_reflns_Laue_measured_fraction_max 0.202
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6537
_diffrn_reflns_point_group_measured_fraction_full 0.321
_diffrn_reflns_point_group_measured_fraction_max 0.202
_diffrn_reflns_theta_full        17.160
_diffrn_reflns_theta_max         24.366
_diffrn_reflns_theta_min         1.862
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.321
_diffrn_measured_fraction_theta_max 0.202
_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  97.00   0.20    0.50  57.05   0.00-134.76    --   390
  2  φ     19.00  97.00   0.20    0.50  57.05   0.00-134.76    --   390
  3  φ     19.00  97.00   0.20    0.50  57.05   0.00-134.76    --   390
  4  φ     19.00  97.00   0.20    0.50  57.05   0.00-134.76    --   390
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dectris-CrysAlisPro-abstract goniometer imported dectris images'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.49173
_diffrn_source                   synchrotron
_diffrn_special_details          
'Data were collected at room temperature and pressure of 2.05(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                1106
_reflns_number_total             1204
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.026
_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     191
_refine_ls_number_reflns         1204
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.131
_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)+(0.0934P)²+0.0322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1318
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
2.a Secondary CH2 refined with riding coordinates:
 C14(H7,H8), C17(H14,H13), C15(H9,H10), C13(H5,H6), C16(H11,H12)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H4), C11(H3), C7(H2), C6(H1)
2.c Idealised Me refined as rotating group:
 C18(H16,H17,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
O2 O 1.0466(2) 0.44920(11) 0.36857(17) 0.0359(15) Uani 1 1 d . . . . .
O1 O 0.7050(3) 0.06173(13) 0.1781(2) 0.0353(18) Uani 1 1 d . . . . .
N1 N 0.8786(2) 0.25427(12) 0.2740(2) 0.0251(16) Uani 1 1 d . . . . .
C2 C 0.8702(3) 0.32959(15) 0.3493(2) 0.0259(5) Uani 1 1 d . U . . .
C12 C 0.6221(3) 0.33447(14) 0.4855(2) 0.0255(18) Uani 1 1 d . . . . .
H4 H 0.755021 0.424264 0.499813 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4043(3) 0.27520(13) 0.5440(2) 0.0296(18) Uani 1 1 d . . . . .
H3 H 0.394646 0.325195 0.596051 0.036 Uiso 1 1 calc R U . . .
C14 C 0.9572(3) 0.41986(13) 0.1473(2) 0.0324(18) Uani 1 1 d . . . . .
H7 H 0.779704 0.358817 0.120509 0.039 Uiso 1 1 calc R U . . .
H8 H 1.100891 0.448077 0.103872 0.039 Uiso 1 1 calc R U . . .
C17 C 0.9231(3) 0.74900(16) 0.0573(3) 0.040(2) Uani 1 1 d . . . . .
H14 H 1.077972 0.822872 0.085999 0.047 Uiso 1 1 calc R U . . .
H13 H 1.023295 0.670878 0.028681 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4402(3) 0.12696(13) 0.3851(2) 0.0247(18) Uani 1 1 d . . . . .
C10 C 0.2038(2) 0.13968(13) 0.5219(2) 0.0255(18) Uani 1 1 d . . . . .
C5 C 0.4599(3) 0.05518(14) 0.3088(2) 0.0254(19) Uani 1 1 d . . . . .
C15 C 0.8649(3) 0.56944(14) 0.1859(2) 0.036(2) Uani 1 1 d . . . . .
H9 H 0.725608 0.541172 0.230368 0.043 Uiso 1 1 calc R U . . .
H10 H 1.043436 0.631640 0.211375 0.043 Uiso 1 1 calc R U . . .
C7 C 0.0507(3) -0.14199(15) 0.3418(3) 0.031(2) Uani 1 1 d . . . . .
H2 H -0.076490 -0.233520 0.326910 0.037 Uiso 1 1 calc R U . . .
C13 C 1.0988(3) 0.31911(14) 0.2120(2) 0.0337(18) Uani 1 1 d . . . . .
H5 H 1.176177 0.233469 0.183010 0.040 Uiso 1 1 calc R U . . .
H6 H 1.268242 0.381911 0.241502 0.040 Uiso 1 1 calc R U . . .
C16 C 0.7150(3) 0.66913(17) 0.1219(3) 0.047(2) Uani 1 1 d . . . . .
H11 H 0.551051 0.602816 0.092069 0.057 Uiso 1 1 calc R U . . .
H12 H 0.626259 0.749189 0.152460 0.057 Uiso 1 1 calc R U . . .
C3 C 0.6410(3) 0.26486(14) 0.4106(2) 0.0274(18) Uani 1 1 d . . . . .
C9 C 0.2205(3) 0.06516(13) 0.4447(2) 0.0273(18) Uani 1 1 d . . . . .
C8 C 0.0225(3) -0.07468(14) 0.4174(2) 0.0269(18) Uani 1 1 d . . . . .
C6 C 0.2656(3) -0.07967(14) 0.2836(2) 0.033(2) Uani 1 1 d . . . . .
H1 H 0.277103 -0.126541 0.230846 0.039 Uiso 1 1 calc R U . . .
C18 C 0.7520(4) 0.83420(19) -0.0068(3) 0.050(3) Uani 1 1 d . . . . .
H16 H 0.890879 0.885623 -0.045553 0.075 Uiso 1 1 calc R U . . .
H17 H 0.650873 0.910850 0.021350 0.075 Uiso 1 1 calc R U . . .
H15 H 0.605043 0.760588 -0.037209 0.075 Uiso 1 1 calc R U . . .
C1 C 0.6847(3) 0.11876(16) 0.2464(3) 0.025(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.238(2) . ?
O1 C1 1.195(6) . ?
N1 C2 1.354(5) . ?
N1 C13 1.480(3) . ?
N1 C1 1.411(3) . ?
C2 C3 1.497(3) . ?
C12 H4 0.9300 . ?
C12 C11 1.420(3) . ?
C12 C3 1.334(5) . ?
C11 H3 0.9300 . ?
C11 C10 1.405(2) . ?
C14 H7 0.9700 . ?
C14 H8 0.9700 . ?
C14 C15 1.528(3) . ?
C14 C13 1.523(3) . ?
C17 H14 0.9700 . ?
C17 H13 0.9700 . ?
C17 C16 1.520(4) . ?
C17 C18 1.502(4) . ?
C4 C5 1.362(5) . ?
C4 C3 1.433(3) . ?
C4 C9 1.444(3) . ?
C10 C9 1.384(5) . ?
C10 C8 1.483(3) 2_556 ?
C5 C6 1.398(2) . ?
C5 C1 1.493(4) . ?
C15 H9 0.9700 . ?
C15 H10 0.9700 . ?
C15 C16 1.526(4) . ?
C7 H2 0.9300 . ?
C7 C8 1.341(5) . ?
C7 C6 1.416(3) . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C9 C8 1.447(3) . ?
C6 H1 0.9300 . ?
C18 H16 0.9600 . ?
C18 H17 0.9600 . ?
C18 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
C2 N1 C13 119.18(14) . . ?
C2 N1 C1 125.7(2) . . ?
C1 N1 C13 115.1(3) . . ?
O2 C2 N1 121.8(2) . . ?
O2 C2 C3 119.6(3) . . ?
N1 C2 C3 118.56(16) . . ?
C11 C12 H4 119.1 . . ?
C3 C12 H4 119.1 . . ?
C3 C12 C11 121.78(16) . . ?
C12 C11 H3 120.6 . . ?
C10 C11 C12 118.8(3) . . ?
C10 C11 H3 120.6 . . ?
H7 C14 H8 107.8 . . ?
C15 C14 H7 109.0 . . ?
C15 C14 H8 109.0 . . ?
C13 C14 H7 109.0 . . ?
C13 C14 H8 109.0 . . ?
C13 C14 C15 112.9(3) . . ?
H14 C17 H13 107.9 . . ?
C16 C17 H14 109.3 . . ?
C16 C17 H13 109.3 . . ?
C18 C17 H14 109.3 . . ?
C18 C17 H13 109.3 . . ?
C18 C17 C16 111.72(15) . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 C9 121.35(17) . . ?
C3 C4 C9 117.1(3) . . ?
C11 C10 C8 119.6(3) . 2_556 ?
C9 C10 C11 120.4(2) . . ?
C9 C10 C8 119.99(17) . 2_556 ?
C4 C5 C6 121.8(2) . . ?
C4 C5 C1 121.80(18) . . ?
C6 C5 C1 116.3(3) . . ?
C14 C15 H9 108.9 . . ?
C14 C15 H10 108.9 . . ?
H9 C15 H10 107.7 . . ?
C16 C15 C14 113.3(3) . . ?
C16 C15 H9 108.9 . . ?
C16 C15 H10 108.9 . . ?
C8 C7 H2 118.6 . . ?
C8 C7 C6 122.81(17) . . ?
C6 C7 H2 118.6 . . ?
N1 C13 C14 112.02(12) . . ?
N1 C13 H5 109.2 . . ?
N1 C13 H6 109.2 . . ?
C14 C13 H5 109.2 . . ?
C14 C13 H6 109.2 . . ?
H5 C13 H6 107.9 . . ?
C17 C16 C15 115.49(13) . . ?
C17 C16 H11 108.4 . . ?
C17 C16 H12 108.4 . . ?
C15 C16 H11 108.4 . . ?
C15 C16 H12 108.4 . . ?
H11 C16 H12 107.5 . . ?
C12 C3 C2 121.12(16) . . ?
C12 C3 C4 121.4(2) . . ?
C4 C3 C2 117.5(3) . . ?
C4 C9 C8 115.8(3) . . ?
C10 C9 C4 120.54(17) . . ?
C10 C9 C8 123.6(2) . . ?
C7 C8 C10 122.76(17) . 2_556 ?
C7 C8 C9 120.9(2) . . ?
C9 C8 C10 116.4(3) . 2_556 ?
C5 C6 C7 117.3(3) . . ?
C5 C6 H1 121.4 . . ?
C7 C6 H1 121.4 . . ?
C17 C18 H16 109.5 . . ?
C17 C18 H17 109.5 . . ?
C17 C18 H15 109.5 . . ?
H16 C18 H17 109.5 . . ?
H16 C18 H15 109.5 . . ?
H17 C18 H15 109.5 . . ?
O1 C1 N1 121.1(2) . . ?
O1 C1 C5 124.01(18) . . ?
N1 C1 C5 114.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C2 C3 C12 0.5(3) . . . . ?
O2 C2 C3 C4 179.51(15) . . . . ?
N1 C2 C3 C12 -179.82(19) . . . . ?
N1 C2 C3 C4 -0.8(3) . . . . ?
C2 N1 C13 C14 -96.3(3) . . . . ?
C2 N1 C1 O1 178.6(2) . . . . ?
C2 N1 C1 C5 -1.6(3) . . . . ?
C12 C11 C10 C9 0.4(3) . . . . ?
C12 C11 C10 C8 179.18(15) . . . 2_556 ?
C11 C12 C3 C2 179.50(13) . . . . ?
C11 C12 C3 C4 0.5(4) . . . . ?
C11 C10 C9 C4 -1.1(3) . . . . ?
C11 C10 C9 C8 179.98(14) . . . . ?
C14 C15 C16 C17 -69.8(2) . . . . ?
C4 C5 C6 C7 -1.6(3) . . . . ?
C4 C5 C1 O1 -178.2(3) . . . . ?
C4 C5 C1 N1 2.0(3) . . . . ?
C4 C9 C8 C10 179.82(12) . . . 2_556 ?
C4 C9 C8 C7 1.3(4) . . . . ?
C10 C9 C8 C10 -1.2(4) . . . 2_556 ?
C10 C9 C8 C7 -179.70(19) . . . . ?
C5 C4 C3 C2 1.2(3) . . . . ?
C5 C4 C3 C12 -179.7(2) . . . . ?
C5 C4 C9 C10 179.99(17) . . . . ?
C5 C4 C9 C8 -1.0(3) . . . . ?
C15 C14 C13 N1 66.20(19) . . . . ?
C13 N1 C2 O2 -1.8(3) . . . . ?
C13 N1 C2 C3 178.48(13) . . . . ?
C13 N1 C1 O1 1.1(4) . . . . ?
C13 N1 C1 C5 -179.11(15) . . . . ?
C13 C14 C15 C16 -178.48(9) . . . . ?
C3 C12 C11 C10 -0.1(3) . . . . ?
C3 C4 C5 C6 179.77(14) . . . . ?
C3 C4 C5 C1 -1.9(4) . . . . ?
C3 C4 C9 C10 1.4(3) . . . . ?
C3 C4 C9 C8 -179.59(14) . . . . ?
C9 C4 C5 C6 1.2(4) . . . . ?
C9 C4 C5 C1 179.52(15) . . . . ?
C9 C4 C3 C2 179.86(14) . . . . ?
C9 C4 C3 C12 -1.1(3) . . . . ?
C8 C10 C9 C4 -179.82(13) 2_556 . . . ?
C8 C10 C9 C8 1.2(4) 2_556 . . . ?
C8 C7 C6 C5 2.0(3) . . . . ?
C6 C5 C1 O1 0.2(4) . . . . ?
C6 C5 C1 N1 -179.60(16) . . . . ?
C6 C7 C8 C10 179.70(14) . . . 2_556 ?
C6 C7 C8 C9 -1.9(4) . . . . ?
C18 C17 C16 C15 175.7(3) . . . . ?
C1 N1 C2 O2 -179.22(17) . . . . ?
C1 N1 C2 C3 1.1(3) . . . . ?
C1 N1 C13 C14 81.4(2) . . . . ?
C1 C5 C6 C7 179.98(17) . . . . ?

_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_C6_1_05GPa
_database_code_depnum_ccdc_archive 'CCDC 2412021'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PDI_C6_1_05GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      15.00 Degree   
RESPONSE: The data come from high-pressure studies and are limited by the 
DAC opening angle.  
;
_vrf_PLAT029_PDI_C6_1_05GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.350 Why?    
RESPONSE: These data come from a high-pressure experiment and part of the 
reflections could not be collected due to the limited DAC opening angle and the 
measurement strategy.
;
_vrf_PLAT088_PDI_C6_1_05GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.91 Note 
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber. 
;
_vrf_PLAT340_PDI_C6_1_05GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02868 Ang.
RESPONSE: The data come from high-pressure studies and are limited by 
the DAC opening angle.
;
_vrf_PLAT911_PDI_C6_1_05GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        566 Report
               -4  6  0,  -3  7  0,  -2  8  0,   3  8  0,  -2  9  0,  -1  9  0, 
                0  9  0,   1  9  0,   2  9  0,   0 10  0,   1 10  0,  -1-10  1, 
                0-10  1,  -2 -9  1,  -1 -9  1,   0 -9  1,   1 -9  1,  -3 -8  1, 
               -2 -8  1,  -1 -8  1,   0 -8  1,   1 -8  1,   2 -8  1,  -4 -7  1, 
               -3 -7  1,  -2 -7  1,  -1 -7  1,   0 -7  1,   1 -7  1,   2 -7  1, 
                3 -7  1,  -4 -6  1,   2 -6  1,   3 -6  1,   4 -6  1,   4 -5  1, 
                0 -4  1,   4 -4  1,   5 -3  1,  -2 -2  1,  -1  0  1,   1  0  1, 
               -1  1  1,   1  4  1,  -2  9  1,   0 10  1,   1 10  1,  -2 -9  2, 
               -1 -9  2,   0 -9  2,   1 -9  2,  -3 -8  2,  -2 -8  2,  -1 -8  2, 
                0 -8  2,   1 -8  2,   2 -8  2,  -4 -7  2,  -3 -7  2,  -2 -7  2, 
               -1 -7  2,   0 -7  2,   1 -7  2,   2 -7  2,   3 -7  2,  -4 -6  2, 
               -3 -6  2,  -2 -6  2,  -1 -6  2,   0 -6  2,   1 -6  2,   2 -6  2, 
                3 -6  2,   4 -6  2,  -4 -5  2,  -3 -5  2,  -2 -5  2,  -1 -5  2, 
                0 -5  2,   1 -5  2,   2 -5  2,   3 -5  2,   4 -5  2,  -5 -4  2, 
               -4 -4  2,  -1 -4  2,   0 -4  2,   1 -4  2,   2 -4  2,   3 -4  2, 
                4 -4  2,  -5 -3  2,  -1 -3  2,   0 -3  2,   1 -3  2,   4 -3  2,
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-06-07
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   4.5494(4)
_cell_length_b                   8.5761(10)
_cell_length_c                   16.782(5)
_cell_angle_alpha                80.612(16)
_cell_angle_beta                 86.817(15)
_cell_angle_gamma                84.468(8)
_cell_volume                     642.5(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1464
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4590
_cell_measurement_theta_min      4.4900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.452
_exptl_absorpt_correction_T_min  0.338
_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    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 2 0 0.0990
-1 12 4 0.1373
6 0 -2 0.0988
0 0 23 0.0131
-6 0 -3 0.0710
0 0 -23 0.0164
1 -12 -4 0.1250

_exptl_crystal_preparation       'mounted in a diamond-anvil cell '
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.039
_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)           0.817     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 = 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  0.0786
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.350
_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       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5266
_diffrn_reflns_point_group_measured_fraction_full 0.350
_diffrn_reflns_point_group_measured_fraction_max 0.208
_diffrn_reflns_theta_full        15.000
_diffrn_reflns_theta_max         26.469
_diffrn_reflns_theta_min         4.505
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.350
_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  ω    -57.00 -21.00   0.75   17.50    --  -29.94  77.00 150.00   48
  2  ω    -19.00  44.00   0.75   17.50    --  -29.94 -39.00-167.00   84
  3  ω    -89.00 -26.00   0.75   17.50    --  -29.94 135.00 123.00   84
  4  ω     13.00  40.00   0.75   17.50    --  -29.94-114.00-135.00   36
  5  ω    -44.00  19.00   0.75   17.50    --  -29.94  19.00-180.00   84
  6  ω    -31.00   0.50   0.75   17.50    --  -29.94   0.00   0.00   42
  7  ω     13.00  40.00   0.75   17.50    --  -29.94-114.00  45.00   36
  8  ω    -55.00   8.00   0.75   17.50    --  -29.94  67.00 -23.00   84
  9  ω    -19.00  44.00   0.75   17.50    --  -29.94 -39.00  12.00   84
 10  ω    -31.00   0.50   0.75   17.50    --   30.41   0.00-150.00   42
 11  ω    -31.00   0.50   0.75   17.50    --   30.41   0.00  30.00   42
 12  ω      8.00  32.00   0.75   17.50    --  -29.94 -99.00-150.00   32
 13  ω    -19.00   5.00   0.75   17.50    --  -29.94 -57.00  30.00   32
 14  ω    -19.00  14.00   0.75   17.50    --  -29.94 -19.00-150.00   44
 15  ω    -40.00 -13.00   0.75   17.50    --   30.41 114.00 135.00   36
 16  ω      1.75  49.00   0.75   17.50    --   30.41 -53.00  17.00   63
 17  ω    -16.00   8.00   0.75   17.50    --   30.41  67.00 157.00   32
 18  ω     20.00  56.00   0.75   17.50    --   30.41 -77.00-150.00   48
 19  ω     31.00  76.00   0.75   17.50    --   30.41-125.00  60.00   60
 20  ω     -5.00  19.00   0.75   17.50    --   30.41  57.00 -30.00   32
 21  ω    -44.00  19.00   0.75   17.50    --  -29.94  39.00 -12.00   84
 22  ω    -44.00  19.00   0.75   17.50    --  -29.94  19.00-180.00   84
 23  ω    -19.00  44.00   0.75   17.50    --  -29.94 -19.00-180.00   84
 24  ω    -19.00  44.00   0.75   17.50    --  -29.94 -39.00  12.00   84
 25  ω    -22.25  40.00   0.75   17.50    --  -29.94 -26.00   7.00   83
 26  ω    -26.25  36.00   0.75   17.50    --  -29.94 -13.00   3.00   83
 27  ω    -36.00  27.00   0.75   17.50    --  -29.94  13.00  -3.00   84
 28  ω    -40.00  23.00   0.75   17.50    --  -29.94  26.00  -7.00   84
 29  ω     -8.00  52.00   0.75   17.50    --  -29.94 -37.00-180.00   80
 30  ω    -49.00  14.00   0.75   17.50    --  -29.94  53.00 -17.00   84
;
_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 1.05(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                308
_reflns_number_total             555
_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    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         555
_refine_ls_number_restraints     531
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.0735
_refine_ls_restrained_S_all      0.748
_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)+(0.0412P)²+3.0297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1936
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C14-C13 \\sim C15-C14
 with sigma of 0.02
 C3-C2 \\sim C4-C3 \\sim C5-C4 \\sim C5-C1 \\sim C3-C12 \\sim C12-C11 \\sim
C11-C10 \\sim C10-C9 \\sim C4-C9 ~
 C9-C8 \\sim C7-C8 \\sim C6-C7
 with sigma of 0.02
 O2-C2 \\sim O1-C1
 with sigma of 0.02
 N1-C1 \\sim N1-C2
 with sigma of 0.02
2. Rigid bond restraints
 O1, O2, N1, C10, C11, C12, C3, C5, C4, C9, C8, C7, C6, C1, C2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C13, C14, C15, C18, C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O1 \\sim O2 \\sim N1 \\sim C10 \\sim C11 \\sim C12 \\sim C3 \\sim C5 \\sim C4
\\sim C9 \\sim C8 \\sim C7 \\sim C6 \\sim C1 \\sim C2: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
C13 \\sim C14 \\sim C15 \\sim C18 \\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(C10) \\sim
Ueq, Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C5)
\\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq,
Uanis(C7) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C16) \\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(C3) \\sim Ueq,
Uanis(C14) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C8) \\sim Ueq,
Uanis(C11) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
4. Rigid body (RIGU) restrains
 O1, O2, N1, C10, C11, C12, C3, C5, C4, C9, C8, C7, C6, C1, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C13, C14, C15, C18, 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(H5,H6), C14(H8,H7), C15(H10,H9), C16(H11,H12), C17(H14,H13)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H4), C11(H3), C7(H2), C6(H1)
5.c Idealised Me refined as rotating group:
 C18(H17,H15,H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O -0.0260(17) 0.4253(11) 0.6205(18) 0.047(6) Uani 1 1 d D U . . .
O1 O 0.254(2) 0.0129(13) 0.8136(17) 0.052(4) Uani 1 1 d D U . . .
N1 N 0.107(2) 0.2165(11) 0.7165(15) 0.034(4) Uani 1 1 d D U . . .
C1 C 0.290(3) 0.0819(18) 0.7440(17) 0.035(4) Uani 1 1 d D U . . .
C5 C 0.508(2) 0.0221(15) 0.6888(15) 0.030(3) Uani 1 1 d D U . . .
C4 C 0.552(2) 0.1051(13) 0.6094(14) 0.028(3) Uani 1 1 d D U . . .
C3 C 0.365(2) 0.2438(13) 0.5863(14) 0.028(3) Uani 1 1 d D U . . .
C2 C 0.140(3) 0.3037(16) 0.6389(18) 0.030(4) Uani 1 1 d D U . . .
C12 C 0.398(3) 0.3256(15) 0.5068(15) 0.031(4) Uani 1 1 d D U . . .
H4 H 0.270986 0.415576 0.490935 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6151(19) 0.2776(12) 0.4500(19) 0.031(4) Uani 1 1 d D U . . .
H3 H 0.630929 0.333398 0.397812 0.037 Uiso 1 1 calc R U . . .
C10 C 0.807(2) 0.1411(13) 0.4758(16) 0.028(4) Uani 1 1 d D U . . .
C9 C 0.776(2) 0.0536(13) 0.5547(14) 0.029(4) Uani 1 1 d D U . . .
C8 C 0.959(2) -0.0874(13) 0.5799(17) 0.031(4) Uani 1 1 d D U . . .
C7 C 0.910(3) -0.1687(17) 0.6590(17) 0.036(4) Uani 1 1 d D U . . .
H2 H 1.028247 -0.261383 0.676531 0.044 Uiso 1 1 calc R U . . .
C6 C 0.687(2) -0.1136(14) 0.713(2) 0.038(4) Uani 1 1 d D U . . .
H1 H 0.661794 -0.170019 0.764311 0.046 Uiso 1 1 calc R U . . .
C13 C -0.111(2) 0.2841(16) 0.775(3) 0.037(17) Uani 1 1 d D U . . .
H5 H -0.167468 0.200263 0.817082 0.044 Uiso 1 1 calc R U . . .
H6 H -0.286696 0.331002 0.746661 0.044 Uiso 1 1 calc R U . . .
C14 C 0.027(2) 0.4102(17) 0.811(2) 0.042(16) Uani 1 1 d D U . . .
H8 H 0.112852 0.483976 0.768312 0.050 Uiso 1 1 calc R U . . .
H7 H 0.184641 0.359589 0.845740 0.050 Uiso 1 1 calc R U . . .
C15 C -0.201(2) 0.5017(15) 0.861(2) 0.037(15) Uani 1 1 d D U . . .
H10 H -0.359035 0.550744 0.826305 0.045 Uiso 1 1 calc R U . . .
H9 H -0.285983 0.427129 0.903722 0.045 Uiso 1 1 calc R U . . .
C16 C -0.075(2) 0.6285(15) 0.898(3) 0.036(15) Uani 1 1 d . U . . .
H11 H 0.080840 0.578610 0.933274 0.043 Uiso 1 1 calc R U . . .
H12 H 0.013442 0.701278 0.855273 0.043 Uiso 1 1 calc R U . . .
C17 C -0.292(3) 0.7215(17) 0.946(3) 0.046(16) Uani 1 1 d . U . . .
H14 H -0.448779 0.771014 0.910669 0.056 Uiso 1 1 calc R U . . .
H13 H -0.379486 0.649026 0.988847 0.056 Uiso 1 1 calc R U . . .
C18 C -0.166(3) 0.846(2) 0.981(3) 0.05(2) Uani 1 1 d . U . . .
H17 H -0.075868 0.918227 0.939146 0.081 Uiso 1 1 calc R U . . .
H15 H -0.019651 0.798143 1.018967 0.081 Uiso 1 1 calc R U . . .
H16 H -0.320495 0.903643 1.008863 0.081 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.234(19) . ?
O1 C1 1.23(3) . ?
N1 C1 1.386(19) . ?
N1 C2 1.40(3) . ?
N1 C13 1.49(3) . ?
C1 C5 1.434(15) . ?
C5 C4 1.419(17) . ?
C5 C6 1.37(2) . ?
C4 C3 1.408(14) . ?
C4 C9 1.419(15) . ?
C3 C2 1.427(16) . ?
C3 C12 1.411(17) . ?
C12 H4 0.9300 . ?
C12 C11 1.413(16) . ?
C11 H3 0.9300 . ?
C11 C10 1.415(14) . ?
C10 C9 1.418(17) . ?
C10 C8 1.47(3) 2_756 ?
C9 C8 1.420(14) . ?
C8 C7 1.411(18) . ?
C7 H2 0.9300 . ?
C7 C6 1.416(16) . ?
C6 H1 0.9300 . ?
C13 H5 0.9700 . ?
C13 H6 0.9700 . ?
C13 C14 1.527(19) . ?
C14 H8 0.9700 . ?
C14 H7 0.9700 . ?
C14 C15 1.532(19) . ?
C15 H10 0.9700 . ?
C15 H9 0.9700 . ?
C15 C16 1.51(3) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C17 1.49(3) . ?
C17 H14 0.9700 . ?
C17 H13 0.9700 . ?
C17 C18 1.48(3) . ?
C18 H17 0.9600 . ?
C18 H15 0.9600 . ?
C18 H16 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 122.8(17) . . ?
C1 N1 C13 119(2) . . ?
C2 N1 C13 117.7(15) . . ?
O1 C1 N1 119.5(18) . . ?
O1 C1 C5 121.6(18) . . ?
N1 C1 C5 118.8(19) . . ?
C4 C5 C1 121.0(15) . . ?
C6 C5 C1 121(2) . . ?
C6 C5 C4 118.1(16) . . ?
C5 C4 C9 122.5(12) . . ?
C3 C4 C5 117.1(15) . . ?
C3 C4 C9 120.4(17) . . ?
C4 C3 C2 123.2(18) . . ?
C4 C3 C12 118.2(15) . . ?
C12 C3 C2 118.6(15) . . ?
O2 C2 N1 118.4(19) . . ?
O2 C2 C3 125(2) . . ?
N1 C2 C3 116.9(15) . . ?
C3 C12 H4 118.4 . . ?
C3 C12 C11 123.2(14) . . ?
C11 C12 H4 118.4 . . ?
C12 C11 H3 121.3 . . ?
C12 C11 C10 117.3(17) . . ?
C10 C11 H3 121.3 . . ?
C11 C10 C9 121.0(15) . . ?
C11 C10 C8 120(2) . 2_756 ?
C9 C10 C8 119.3(13) . 2_756 ?
C4 C9 C8 118.8(17) . . ?
C10 C9 C4 119.8(13) . . ?
C10 C9 C8 121.4(15) . . ?
C9 C8 C10 119.3(19) . 2_756 ?
C7 C8 C10 122.8(14) . 2_756 ?
C7 C8 C9 117.8(16) . . ?
C8 C7 H2 119.0 . . ?
C8 C7 C6 122.0(16) . . ?
C6 C7 H2 119.0 . . ?
C5 C6 C7 121(2) . . ?
C5 C6 H1 119.6 . . ?
C7 C6 H1 119.6 . . ?
N1 C13 H5 109.7 . . ?
N1 C13 H6 109.7 . . ?
N1 C13 C14 109.7(11) . . ?
H5 C13 H6 108.2 . . ?
C14 C13 H5 109.7 . . ?
C14 C13 H6 109.7 . . ?
C13 C14 H8 109.2 . . ?
C13 C14 H7 109.2 . . ?
C13 C14 C15 111.9(10) . . ?
H8 C14 H7 107.9 . . ?
C15 C14 H8 109.2 . . ?
C15 C14 H7 109.2 . . ?
C14 C15 H10 108.8 . . ?
C14 C15 H9 108.8 . . ?
H10 C15 H9 107.7 . . ?
C16 C15 C14 113.8(10) . . ?
C16 C15 H10 108.8 . . ?
C16 C15 H9 108.8 . . ?
C15 C16 H11 108.5 . . ?
C15 C16 H12 108.5 . . ?
H11 C16 H12 107.5 . . ?
C17 C16 C15 115.2(10) . . ?
C17 C16 H11 108.5 . . ?
C17 C16 H12 108.5 . . ?
C16 C17 H14 108.6 . . ?
C16 C17 H13 108.6 . . ?
H14 C17 H13 107.6 . . ?
C18 C17 C16 114.7(12) . . ?
C18 C17 H14 108.6 . . ?
C18 C17 H13 108.6 . . ?
C17 C18 H17 109.5 . . ?
C17 C18 H15 109.5 . . ?
C17 C18 H16 109.5 . . ?
H17 C18 H15 109.5 . . ?
H17 C18 H16 109.5 . . ?
H15 C18 H16 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 C5 C4 -178.4(17) . . . . ?
O1 C1 C5 C6 -1(3) . . . . ?
N1 C1 C5 C4 5(2) . . . . ?
N1 C1 C5 C6 -177.8(13) . . . . ?
N1 C13 C14 C15 171(2) . . . . ?
C1 N1 C2 O2 -177.4(15) . . . . ?
C1 N1 C2 C3 3.1(19) . . . . ?
C1 N1 C13 C14 92(2) . . . . ?
C1 C5 C4 C3 -2.8(18) . . . . ?
C1 C5 C4 C9 176.7(12) . . . . ?
C1 C5 C6 C7 -177.3(13) . . . . ?
C5 C4 C3 C2 0.9(17) . . . . ?
C5 C4 C3 C12 -178.0(12) . . . . ?
C5 C4 C9 C10 179.5(12) . . . . ?
C5 C4 C9 C8 0.9(16) . . . . ?
C4 C5 C6 C7 0.1(19) . . . . ?
C4 C3 C2 O2 179.5(14) . . . . ?
C4 C3 C2 N1 -1.0(18) . . . . ?
C4 C3 C12 C11 -1.7(18) . . . . ?
C4 C9 C8 C10 -179.4(12) . . . 2_756 ?
C4 C9 C8 C7 -0.5(16) . . . . ?
C3 C4 C9 C10 -0.9(16) . . . . ?
C3 C4 C9 C8 -179.6(12) . . . . ?
C3 C12 C11 C10 -0.5(17) . . . . ?
C2 N1 C1 O1 178.2(18) . . . . ?
C2 N1 C1 C5 -5(2) . . . . ?
C2 N1 C13 C14 -80(2) . . . . ?
C2 C3 C12 C11 179.3(11) . . . . ?
C12 C3 C2 O2 -2(2) . . . . ?
C12 C3 C2 N1 177.9(12) . . . . ?
C12 C11 C10 C9 2.1(16) . . . . ?
C12 C11 C10 C8 -178.8(12) . . . 2_756 ?
C11 C10 C9 C4 -1.4(17) . . . . ?
C11 C10 C9 C8 177.2(12) . . . . ?
C10 C9 C8 C10 1.9(19) . . . 2_756 ?
C10 C9 C8 C7 -179.1(12) . . . . ?
C10 C8 C7 C6 178.9(12) 2_756 . . . ?
C9 C4 C3 C2 -178.7(11) . . . . ?
C9 C4 C3 C12 2.4(16) . . . . ?
C9 C8 C7 C6 -0.1(19) . . . . ?
C8 C10 C9 C4 179.5(11) 2_756 . . . ?
C8 C10 C9 C8 -1.9(19) 2_756 . . . ?
C8 C7 C6 C5 0(2) . . . . ?
C6 C5 C4 C3 179.8(12) . . . . ?
C6 C5 C4 C9 -0.7(18) . . . . ?
C13 N1 C1 O1 6(2) . . . . ?
C13 N1 C1 C5 -177.1(12) . . . . ?
C13 N1 C2 O2 -5(2) . . . . ?
C13 N1 C2 C3 175.3(12) . . . . ?
C13 C14 C15 C16 -180(3) . . . . ?
C14 C15 C16 C17 179(2) . . . . ?
C15 C16 C17 C18 -180(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
- 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_C6_0_73GPa
_database_code_depnum_ccdc_archive 'CCDC 2412020'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-05 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT027_PDI_C6_0_73GPa      
;
PROBLEM:_diffrn_reflns_theta_full value (too) Low ......      15.00 Degree   
RESPONSE: The data come from high-pressure studies and are limited by the 
DAC opening angle.  
;
_vrf_PLAT029_PDI_C6_0_73GPa      
;
PROBLEM:_diffrn_measured_fraction_theta_full value Low .      0.315 Why?    
RESPONSE: These data come from a high-pressure experiment and part of the 
reflections could not be collected due to the limited DAC opening angle and the 
measurement strategy.
;
_vrf_PLAT088_PDI_C6_0_73GPa      
;
PROBLEM: Poor Data / Parameter Ratio ....................       2.29 Note 
RESPONSE: The data/parameter ratio is affected by the access limits of the DAC 
chamber. 
;
_vrf_PLAT340_PDI_C6_0_73GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03211 Ang.
RESPONSE: The data come from high-pressure studies and are limited by
 the DAC opening angle.
;
_vrf_PLAT911_PDI_C6_0_73GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600        703 Report
                5  0  0,  -5  1  0,  -4  1  0,  -5  2  0,  -4  2  0,  -3  2  0, 
               -2  2  0,   0  2  0,  -5  3  0,  -4  3  0,  -3  3  0,  -2  3  0, 
               -4  4  0,  -3  4  0,  -2  4  0,  -4  5  0,  -3  5  0,  -2  5  0, 
               -1  5  0,   0  5  0,  -4  6  0,  -3  6  0,  -2  6  0,  -1  6  0, 
                0  6  0,  -3  7  0,  -2  7  0,  -1  7  0,   0  7  0,   4  7  0, 
               -2  8  0,  -1  8  0,   0  8  0,   1  8  0,   2  8  0,   3  8  0, 
               -2  9  0,  -1  9  0,   0  9  0,   1  9  0,   2  9  0,   0 10  0, 
                1 10  0,  -1-10  1,   0-10  1,  -2 -9  1,  -1 -9  1,   0 -9  1, 
                1 -9  1,  -3 -8  1,  -2 -8  1,  -1 -8  1,   0 -8  1,   1 -8  1, 
                2 -8  1,  -4 -7  1,  -3 -7  1,  -2 -7  1,  -1 -7  1,   0 -7  1, 
                1 -7  1,   2 -7  1,   3 -7  1,  -4 -6  1,  -3 -6  1,   1 -6  1, 
                2 -6  1,   3 -6  1,   4 -6  1,  -3 -5  1,   2 -5  1,   3 -5  1, 
                4 -5  1,  -5 -4  1,   0 -4  1,   3 -4  1,   4 -4  1,   3 -3  1, 
                4 -3  1,   5 -3  1,  -2 -2  1,   0 -2  1,   3 -2  1,   4 -2  1, 
                5 -2  1,   3 -1  1,   4 -1  1,   5 -1  1,  -5  0  1,  -1  0  1, 
                1  0  1,   5  0  1,  -5  1  1,  -4  1  1,  -1  1  1,   1  1  1, 
RESPONSE: The data come from high-pressure studies and are limited by the DAC 
opening angle and the measurement strategy.
;
# end Validation Reply Form
loop_
_audit_creation_date
2024-06-07
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   4.5971(3)
_cell_length_b                   8.5635(10)
_cell_length_c                   16.880(6)
_cell_angle_alpha                80.833(20)
_cell_angle_beta                 86.337(16)
_cell_angle_gamma                84.247(7)
_cell_volume                     651.9(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    835
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.8300
_cell_measurement_theta_min      4.4310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.452
_exptl_absorpt_correction_T_min  0.337
_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    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
6 3 1 0.0672
-6 -1 0 0.1352
-1 12 4 0.1177
1 -12 -4 0.1540
0 0 23 0.0180
-6 0 2 0.1218
0 0 -23 0.0148
6 0 -3 0.0677

_exptl_crystal_preparation       'mounted in a diamond-anvil cell'
_exptl_crystal_size_max          0.324
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.039
_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)      0.400     0.454
         range of gasket transmission (min-max)           0.809     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 = 250.0 microns, radius = 250.0 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  0.0474
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_Laue_measured_fraction_full 0.315
_diffrn_reflns_Laue_measured_fraction_max 0.155
_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       -6
_diffrn_reflns_number            1850
_diffrn_reflns_point_group_measured_fraction_full 0.315
_diffrn_reflns_point_group_measured_fraction_max 0.155
_diffrn_reflns_theta_full        15.000
_diffrn_reflns_theta_max         26.233
_diffrn_reflns_theta_min         4.461
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2413
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.315
_diffrn_measured_fraction_theta_max 0.155
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00 -21.00   0.75   17.50    --  -29.94  77.00 150.00   48
  2  ω    -19.00  44.00   0.75   17.50    --  -29.94 -39.00-167.00   84
  3  ω    -89.00 -26.00   0.75   17.50    --  -29.94 135.00 123.00   84
  4  ω     13.00  40.00   0.75   17.50    --  -29.94-114.00-135.00   36
  5  ω    -44.00  19.00   0.75   17.50    --  -29.94  19.00-180.00   84
  6  ω    -31.00   0.50   0.75   17.50    --  -29.94   0.00   0.00   42
  7  ω     13.00  40.00   0.75   17.50    --  -29.94-114.00  45.00   36
  8  ω    -55.00   8.00   0.75   17.50    --  -29.94  67.00 -23.00   84
  9  ω    -19.00  44.00   0.75   17.50    --  -29.94 -39.00  12.00   84
 10  ω    -31.00   0.50   0.75   17.50    --   30.41   0.00-150.00   42
 11  ω    -31.00   0.50   0.75   17.50    --   30.41   0.00  30.00   42
 12  ω      8.00  32.00   0.75   17.50    --  -29.94 -99.00-150.00   32
 13  ω    -19.00   5.00   0.75   17.50    --  -29.94 -57.00  30.00   32
 14  ω    -19.00  14.00   0.75   17.50    --  -29.94 -19.00-150.00   44
 15  ω    -40.00 -13.00   0.75   17.50    --   30.41 114.00 135.00   36
 16  ω      1.75  49.00   0.75   17.50    --   30.41 -53.00  17.00   63
 17  ω    -16.00   8.00   0.75   17.50    --   30.41  67.00 157.00   32
 18  ω     20.00  56.00   0.75   17.50    --   30.41 -77.00-150.00   48
 19  ω     31.00  76.00   0.75   17.50    --   30.41-125.00  60.00   60
 20  ω     -5.00  19.00   0.75   17.50    --   30.41  57.00 -30.00   32
 21  ω    -44.00  19.00   0.75   17.50    --  -29.94  39.00 -12.00   84
 22  ω    -44.00  19.00   0.75   17.50    --  -29.94  19.00-180.00   84
 23  ω    -19.00  44.00   0.75   17.50    --  -29.94 -19.00-180.00   84
 24  ω    -19.00  44.00   0.75   17.50    --  -29.94 -39.00  12.00   84
 25  ω    -22.25  40.00   0.75   17.50    --  -29.94 -26.00   7.00   83
 26  ω    -26.25  36.00   0.75   17.50    --  -29.94 -13.00   3.00   83
 27  ω    -36.00  27.00   0.75   17.50    --  -29.94  13.00  -3.00   84
 28  ω    -40.00  23.00   0.75   17.50    --  -29.94  26.00  -7.00   84
 29  ω     -8.00  52.00   0.75   17.50    --  -29.94 -37.00-180.00   80
 30  ω    -49.00  14.00   0.75   17.50    --  -29.94  53.00 -17.00   84
;
_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 0.73(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                180
_reflns_number_total             410
_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         0.086
_refine_diff_density_min         -0.093
_refine_diff_density_rms         0.022
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         410
_refine_ls_number_restraints     374
_refine_ls_R_factor_all          0.1640
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      0.770
_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)+2.8846P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.1241
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C3-C2 \\sim C12-C3 \\sim C11-C12 \\sim C10-C11 \\sim C9-C10 \\sim C9-C4 \\sim
C3-C4 \\sim C4-C5 \\sim C1-C5 ~
 C6-C5 \\sim C6-C7 \\sim C8-C9 \\sim C7-C8
 with sigma of 0.02
 O1-C1 \\sim O2-C2
 with sigma of 0.02
 N1-C13 \\sim C14-C13 \\sim C15-C14 \\sim C16-C15 \\sim C17-C16 \\sim C18-C17
 with sigma of 0.02
 N1-C1 \\sim N1-C2
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(N1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C9)
\\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C12) \\sim Ueq,
Uanis(C11) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(O1) \\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, Uanis(C16)
\\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
Uanis(C1) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C3) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7)
\\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq,
Uanis(C11) \\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C14) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C18) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 O2, C2, N1, C3, C1, C4, C12, O1, C5, C9, C11, C6, C10, C8, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C13, C14, C15, C16, C17, C18
 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(H8,H7), C15(H10,H9), C16(H11,H12), C17(H14,H13)
4.b Aromatic/amide H refined with riding coordinates:
 C12(H4), C11(H3), C7(H2), C6(H1)
4.c Fitted hexagon refined as free rotating group:
 N1(C1,C5,C4,C3,C2)
4.d Idealised Me refined as rotating group:
 C18(H17,H15,H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O -0.026(3) 0.4261(16) 0.618(2) 0.053(8) Uani 1 1 d D U . . .
O1 O 0.250(3) 0.0169(18) 0.8133(17) 0.063(6) Uani 1 1 d D U . . .
N1 N 0.108(2) 0.2189(16) 0.7132(11) 0.046(6) Uani 1 1 d DG U . . .
C1 C 0.287(3) 0.0820(16) 0.7392(9) 0.042(6) Uani 1 1 d DG U . . .
C5 C 0.507(2) 0.0261(12) 0.6877(12) 0.030(4) Uani 1 1 d DG U . . .
C4 C 0.549(2) 0.1071(17) 0.6103(11) 0.036(5) Uani 1 1 d DG U . . .
C3 C 0.370(3) 0.2440(17) 0.5843(9) 0.033(5) Uani 1 1 d DG U . . .
C2 C 0.149(2) 0.2999(11) 0.6357(12) 0.043(6) Uani 1 1 d DG U . . .
C12 C 0.400(4) 0.324(2) 0.5053(13) 0.037(5) Uani 1 1 d D U . . .
H4 H 0.271215 0.411977 0.489111 0.045 Uiso 1 1 calc R U . . .
C11 C 0.617(3) 0.2759(19) 0.450(2) 0.034(5) Uani 1 1 d D U . . .
H3 H 0.635506 0.329849 0.397554 0.040 Uiso 1 1 calc R U . . .
C10 C 0.806(4) 0.1407(19) 0.4779(19) 0.027(5) Uani 1 1 d D U . . .
C9 C 0.769(3) 0.053(2) 0.5553(16) 0.029(5) Uani 1 1 d D U . . .
C8 C 0.962(4) -0.084(2) 0.578(2) 0.036(5) Uani 1 1 d D U . . .
C7 C 0.916(4) -0.168(2) 0.656(2) 0.034(6) Uani 1 1 d D U . . .
H2 H 1.034502 -0.260579 0.673090 0.041 Uiso 1 1 calc R U . . .
C6 C 0.691(3) -0.1128(17) 0.709(2) 0.044(6) Uani 1 1 d D U . . .
H1 H 0.664280 -0.170992 0.760099 0.053 Uiso 1 1 calc R U . . .
C13 C -0.110(3) 0.281(2) 0.775(2) 0.06(3) Uani 1 1 d D U . . .
H6 H -0.291659 0.322837 0.750264 0.071 Uiso 1 1 calc R U . . .
H5 H -0.151635 0.194964 0.818043 0.071 Uiso 1 1 calc R U . . .
C14 C 0.024(3) 0.410(2) 0.808(3) 0.049(7) Uani 1 1 d D U . . .
H8 H 0.101958 0.483631 0.764397 0.059 Uiso 1 1 calc R U . . .
H7 H 0.184032 0.363054 0.841583 0.059 Uiso 1 1 calc R U . . .
C15 C -0.202(3) 0.501(2) 0.858(2) 0.056(18) Uani 1 1 d D U . . .
H10 H -0.357760 0.551147 0.824532 0.068 Uiso 1 1 calc R U . . .
H9 H -0.286236 0.426207 0.900821 0.068 Uiso 1 1 calc R U . . .
C16 C -0.073(3) 0.627(2) 0.896(3) 0.052(7) Uani 1 1 d D U . . .
H11 H 0.082244 0.576547 0.929997 0.062 Uiso 1 1 calc R U . . .
H12 H 0.012787 0.701127 0.853483 0.062 Uiso 1 1 calc R U . . .
C17 C -0.295(4) 0.719(3) 0.945(3) 0.07(2) Uani 1 1 d D U . . .
H14 H -0.451512 0.768143 0.911264 0.084 Uiso 1 1 calc R U . . .
H13 H -0.379430 0.644697 0.987962 0.084 Uiso 1 1 calc R U . . .
C18 C -0.170(4) 0.846(3) 0.982(4) 0.078(12) Uani 1 1 d D U . . .
H17 H -0.074280 0.915542 0.940614 0.117 Uiso 1 1 calc R U . . .
H15 H -0.031554 0.796753 1.020725 0.117 Uiso 1 1 calc R U . . .
H16 H -0.325629 0.905169 1.008008 0.117 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.289(17) . ?
O1 C1 1.29(3) . ?
N1 C1 1.3900 . ?
N1 C2 1.3900 . ?
N1 C13 1.520(18) . ?
C1 C5 1.3900 . ?
C5 C4 1.3900 . ?
C5 C6 1.399(16) . ?
C4 C3 1.3900 . ?
C4 C9 1.422(16) . ?
C3 C2 1.3900 . ?
C3 C12 1.403(19) . ?
C12 H4 0.9300 . ?
C12 C11 1.400(17) . ?
C11 H3 0.9300 . ?
C11 C10 1.414(16) . ?
C10 C9 1.410(19) . ?
C10 C8 1.48(4) 2_756 ?
C9 C8 1.414(16) . ?
C8 C7 1.411(19) . ?
C7 H2 0.9300 . ?
C7 C6 1.419(17) . ?
C6 H1 0.9300 . ?
C13 H6 0.9700 . ?
C13 H5 0.9700 . ?
C13 C14 1.519(15) . ?
C14 H8 0.9700 . ?
C14 H7 0.9700 . ?
C14 C15 1.523(17) . ?
C15 H10 0.9700 . ?
C15 H9 0.9700 . ?
C15 C16 1.519(16) . ?
C16 H11 0.9700 . ?
C16 H12 0.9700 . ?
C16 C17 1.512(18) . ?
C17 H14 0.9700 . ?
C17 H13 0.9700 . ?
C17 C18 1.509(17) . ?
C18 H17 0.9600 . ?
C18 H15 0.9600 . ?
C18 H16 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 120.0 . . ?
C1 N1 C13 116.9(17) . . ?
C2 N1 C13 122.9(16) . . ?
O1 C1 N1 117.3(16) . . ?
O1 C1 C5 122.5(16) . . ?
N1 C1 C5 120.0 . . ?
C1 C5 C6 123.1(19) . . ?
C4 C5 C1 120.0 . . ?
C4 C5 C6 116.9(19) . . ?
C5 C4 C3 120.0 . . ?
C5 C4 C9 121.8(17) . . ?
C3 C4 C9 118.2(17) . . ?
C4 C3 C2 120.0 . . ?
C4 C3 C12 120.8(18) . . ?
C2 C3 C12 119.2(18) . . ?
O2 C2 N1 115(2) . . ?
O2 C2 C3 125(2) . . ?
C3 C2 N1 120.0 . . ?
C3 C12 H4 118.5 . . ?
C11 C12 C3 123(2) . . ?
C11 C12 H4 118.5 . . ?
C12 C11 H3 122.1 . . ?
C12 C11 C10 116(2) . . ?
C10 C11 H3 122.1 . . ?
C11 C10 C8 118(3) . 2_756 ?
C9 C10 C11 122(2) . . ?
C9 C10 C8 119.2(17) . 2_756 ?
C10 C9 C4 120(2) . . ?
C10 C9 C8 119(2) . . ?
C8 C9 C4 121(2) . . ?
C9 C8 C10 122(3) . 2_756 ?
C7 C8 C10 121(2) . 2_756 ?
C7 C8 C9 117(3) . . ?
C8 C7 H2 119.8 . . ?
C8 C7 C6 120(3) . . ?
C6 C7 H2 119.8 . . ?
C5 C6 C7 123(2) . . ?
C5 C6 H1 118.7 . . ?
C7 C6 H1 118.7 . . ?
N1 C13 H6 110.1 . . ?
N1 C13 H5 110.1 . . ?
H6 C13 H5 108.4 . . ?
C14 C13 N1 108.2(14) . . ?
C14 C13 H6 110.1 . . ?
C14 C13 H5 110.1 . . ?
C13 C14 H8 109.3 . . ?
C13 C14 H7 109.3 . . ?
C13 C14 C15 111.6(12) . . ?
H8 C14 H7 108.0 . . ?
C15 C14 H8 109.3 . . ?
C15 C14 H7 109.3 . . ?
C14 C15 H10 108.9 . . ?
C14 C15 H9 108.9 . . ?
H10 C15 H9 107.8 . . ?
C16 C15 C14 113.1(12) . . ?
C16 C15 H10 108.9 . . ?
C16 C15 H9 108.9 . . ?
C15 C16 H11 108.8 . . ?
C15 C16 H12 108.8 . . ?
H11 C16 H12 107.7 . . ?
C17 C16 C15 113.7(12) . . ?
C17 C16 H11 108.8 . . ?
C17 C16 H12 108.8 . . ?
C16 C17 H14 108.7 . . ?
C16 C17 H13 108.7 . . ?
H14 C17 H13 107.6 . . ?
C18 C17 C16 114.1(14) . . ?
C18 C17 H14 108.7 . . ?
C18 C17 H13 108.7 . . ?
C17 C18 H17 109.5 . . ?
C17 C18 H15 109.5 . . ?
C17 C18 H16 109.5 . . ?
H17 C18 H15 109.5 . . ?
H17 C18 H16 109.5 . . ?
H15 C18 H16 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 C5 C4 -175.7(17) . . . . ?
O1 C1 C5 C6 5.8(16) . . . . ?
N1 C1 C5 C4 0.0 . . . . ?
N1 C1 C5 C6 -178.4(13) . . . . ?
N1 C13 C14 C15 169(2) . . . . ?
C1 N1 C2 O2 -179.1(12) . . . . ?
C1 N1 C2 C3 0.0 . . . . ?
C1 N1 C13 C14 97(2) . . . . ?
C1 C5 C4 C3 0.0 . . . . ?
C1 C5 C4 C9 -179.1(11) . . . . ?
C1 C5 C6 C7 -179.6(12) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C5 C4 C3 C12 -177.4(15) . . . . ?
C5 C4 C9 C10 -178.7(12) . . . . ?
C5 C4 C9 C8 -2.1(18) . . . . ?
C4 C5 C6 C7 2(2) . . . . ?
C4 C3 C2 O2 179.0(14) . . . . ?
C4 C3 C2 N1 0.0 . . . . ?
C4 C3 C12 C11 -3(2) . . . . ?
C4 C9 C8 C10 -179.3(14) . . . 2_756 ?
C4 C9 C8 C7 3(2) . . . . ?
C3 C4 C9 C10 2.2(18) . . . . ?
C3 C4 C9 C8 178.8(12) . . . . ?
C3 C12 C11 C10 0(2) . . . . ?
C2 N1 C1 O1 175.9(16) . . . . ?
C2 N1 C1 C5 0.0 . . . . ?
C2 N1 C13 C14 -78(2) . . . . ?
C2 C3 C12 C11 179.6(11) . . . . ?
C12 C3 C2 O2 -3.5(15) . . . . ?
C12 C3 C2 N1 177.4(15) . . . . ?
C12 C11 C10 C9 4(2) . . . . ?
C12 C11 C10 C8 179.5(15) . . . 2_756 ?
C11 C10 C9 C4 -5(2) . . . . ?
C11 C10 C9 C8 178.1(15) . . . . ?
C10 C9 C8 C10 -3(3) . . . 2_756 ?
C10 C9 C8 C7 179.9(17) . . . . ?
C10 C8 C7 C6 -179.5(16) 2_756 . . . ?
C9 C4 C3 C2 179.1(10) . . . . ?
C9 C4 C3 C12 1.7(15) . . . . ?
C9 C8 C7 C6 -2(3) . . . . ?
C8 C10 C9 C4 179.2(14) 2_756 . . . ?
C8 C10 C9 C8 3(2) 2_756 . . . ?
C8 C7 C6 C5 -1(3) . . . . ?
C6 C5 C4 C3 178.5(12) . . . . ?
C6 C5 C4 C9 -0.5(15) . . . . ?
C13 N1 C1 O1 1.2(14) . . . . ?
C13 N1 C1 C5 -174.8(10) . . . . ?
C13 N1 C2 O2 -4.7(16) . . . . ?
C13 N1 C2 C3 174.4(11) . . . . ?
C13 C14 C15 C16 178(3) . . . . ?
C14 C15 C16 C17 180(2) . . . . ?
C15 C16 C17 C18 -179(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_C6_298K
_database_code_depnum_ccdc_archive 'CCDC 2422224'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-07 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_PDI_C6_298K         
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        30% Check 
RESPONSE: Due to the overall poor diffraction quality
of the needle-shaped crystal and low symmetry.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-02-07
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   4.7568(10)
_cell_length_b                   8.5487(16)
_cell_length_c                   17.576(2)
_cell_angle_alpha                81.678(14)
_cell_angle_beta                 84.850(15)
_cell_angle_gamma                83.169(16)
_cell_volume                     700.3(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    484
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.7550
_cell_measurement_theta_min      3.5820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53a (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    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.621
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.023
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.1485
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.807
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5401
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.807
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.518
_diffrn_reflns_theta_min         3.524
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.807
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                958
_reflns_number_total             3166
_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 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (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    ?
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2545
_refine_ls_R_factor_gt           0.0724
_refine_ls_restrained_S_all      0.914
_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)+(0.0536P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1986
_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.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C11(H11), C12(H12)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 -0.0260(5) 0.4253(3) 0.61707(16) 0.0687(9) Uani 1 1 d . . . . .
O2 O 0.2561(6) 0.0207(4) 0.80058(18) 0.0851(10) Uani 1 1 d . . . . .
N1 N 0.1125(7) 0.2211(4) 0.7086(2) 0.0540(9) Uani 1 1 d . . . . .
C8 C 0.8063(7) 0.1389(4) 0.4768(2) 0.0415(10) Uani 1 1 d . . . . .
C6 C 0.3958(8) 0.3218(4) 0.5072(2) 0.0515(11) Uani 1 1 d . . . . .
H6 H 0.269329 0.409621 0.491385 0.062 Uiso 1 1 calc R U . . .
C7 C 0.6170(7) 0.2697(4) 0.4552(2) 0.0482(11) Uani 1 1 d . . . . .
H7 H 0.636069 0.324136 0.405491 0.058 Uiso 1 1 calc R U . . .
C9 C 0.7749(8) 0.0557(4) 0.5520(2) 0.0427(10) Uani 1 1 d . . . . .
C4 C 0.5510(7) 0.1099(4) 0.6051(2) 0.0430(10) Uani 1 1 d . . . . .
C10 C 0.9608(8) -0.0823(4) 0.5773(2) 0.0433(10) Uani 1 1 d . . . . .
C5 C 0.3644(7) 0.2457(4) 0.5801(2) 0.0443(10) Uani 1 1 d . . . . .
C1 C 0.1354(8) 0.3055(5) 0.6356(3) 0.0507(11) Uani 1 1 d . . . . .
C3 C 0.5163(8) 0.0284(5) 0.6791(2) 0.0490(10) Uani 1 1 d . . . . .
C11 C 0.9153(8) -0.1592(5) 0.6509(2) 0.0556(11) Uani 1 1 d . . . . .
H11 H 1.033445 -0.250356 0.667199 0.067 Uiso 1 1 calc R U . . .
C2 C 0.2880(9) 0.0855(5) 0.7351(3) 0.0581(12) Uani 1 1 d . . . . .
C12 C 0.6948(8) -0.1034(5) 0.7019(2) 0.0605(12) Uani 1 1 d . . . . .
H12 H 0.670326 -0.156882 0.751601 0.073 Uiso 1 1 calc R U . . .
C13 C -0.1041(8) 0.2893(5) 0.7641(2) 0.0624(13) Uani 1 1 d . . . . .
H13A H -0.166743 0.204908 0.802645 0.075 Uiso 1 1 calc R U . . .
H13B H -0.267405 0.340028 0.737250 0.075 Uiso 1 1 calc R U . . .
C16 C -0.0800(8) 0.6221(5) 0.8919(2) 0.0699(13) Uani 1 1 d . . . . .
H16A H 0.066978 0.568174 0.924128 0.084 Uiso 1 1 calc R U . . .
H16B H 0.008326 0.695918 0.852396 0.084 Uiso 1 1 calc R U . . .
C14 C 0.0185(8) 0.4102(5) 0.8032(2) 0.0661(13) Uani 1 1 d . . . . .
H14A H 0.167133 0.355965 0.834762 0.079 Uiso 1 1 calc R U . . .
H14B H 0.104091 0.485826 0.764037 0.079 Uiso 1 1 calc R U . . .
C15 C -0.2014(8) 0.4999(5) 0.8534(2) 0.0706(13) Uani 1 1 d . . . . .
H15A H -0.285668 0.424361 0.892825 0.085 Uiso 1 1 calc R U . . .
H15B H -0.351017 0.553251 0.821896 0.085 Uiso 1 1 calc R U . . .
C17 C -0.2965(9) 0.7151(5) 0.9407(3) 0.0838(15) Uani 1 1 d . . . . .
H17A H -0.386344 0.641424 0.979967 0.101 Uiso 1 1 calc R U . . .
H17B H -0.442480 0.770231 0.908432 0.101 Uiso 1 1 calc R U . . .
C18 C -0.1723(11) 0.8352(6) 0.9795(3) 0.1114(19) Uani 1 1 d . . . . .
H18A H -0.015251 0.783434 1.007501 0.167 Uiso 1 1 calc R U . . .
H18B H -0.314963 0.880947 1.014384 0.167 Uiso 1 1 calc R U . . .
H18C H -0.107870 0.917627 0.941075 0.167 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.227(4) . ?
O2 C2 1.207(5) . ?
N1 C1 1.380(5) . ?
N1 C2 1.394(5) . ?
N1 C13 1.481(4) . ?
C8 C7 1.380(5) . ?
C8 C9 1.412(5) . ?
C8 C10 1.477(5) 2_756 ?
C6 H6 0.9300 . ?
C6 C7 1.406(5) . ?
C6 C5 1.354(5) . ?
C7 H7 0.9300 . ?
C9 C4 1.432(5) . ?
C9 C10 1.429(5) . ?
C4 C5 1.416(5) . ?
C4 C3 1.389(5) . ?
C10 C11 1.374(5) . ?
C5 C1 1.490(5) . ?
C3 C2 1.486(5) . ?
C3 C12 1.362(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.403(5) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.517(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C15 1.517(4) . ?
C16 C17 1.507(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.516(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.513(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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 125.4(4) . . ?
C1 N1 C13 116.2(4) . . ?
C2 N1 C13 118.2(4) . . ?
C7 C8 C9 119.3(4) . . ?
C7 C8 C10 121.5(4) . 2_756 ?
C9 C8 C10 119.1(3) . 2_756 ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.8(4) . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C8 C9 C4 119.7(4) . . ?
C8 C9 C10 122.0(4) . . ?
C10 C9 C4 118.4(4) . . ?
C5 C4 C9 118.6(4) . . ?
C3 C4 C9 120.2(4) . . ?
C3 C4 C5 121.2(4) . . ?
C9 C10 C8 118.9(4) . 2_756 ?
C11 C10 C8 122.1(4) . 2_756 ?
C11 C10 C9 119.0(4) . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 C1 120.3(4) . . ?
C4 C5 C1 119.0(4) . . ?
O1 C1 N1 121.3(4) . . ?
O1 C1 C5 121.2(4) . . ?
N1 C1 C5 117.4(4) . . ?
C4 C3 C2 120.6(4) . . ?
C12 C3 C4 120.4(4) . . ?
C12 C3 C2 118.9(4) . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.5(4) . . ?
C12 C11 H11 119.3 . . ?
O2 C2 N1 121.0(4) . . ?
O2 C2 C3 122.6(5) . . ?
N1 C2 C3 116.4(4) . . ?
C3 C12 C11 120.5(4) . . ?
C3 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
N1 C13 H13A 109.6 . . ?
N1 C13 H13B 109.6 . . ?
N1 C13 C14 110.2(3) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H16A C16 H16B 107.6 . . ?
C15 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C17 C16 C15 114.1(3) . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 C13 113.1(3) . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 C16 113.2(3) . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C16 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C16 C17 C18 113.5(4) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 172.8(3) . . . . ?
C8 C9 C4 C5 0.6(4) . . . . ?
C8 C9 C4 C3 179.5(3) . . . . ?
C8 C9 C10 C8 0.4(5) . . . 2_756 ?
C8 C9 C10 C11 -178.9(3) . . . . ?
C8 C10 C11 C12 179.4(3) 2_756 . . . ?
C6 C5 C1 O1 -1.1(5) . . . . ?
C6 C5 C1 N1 179.1(3) . . . . ?
C7 C8 C9 C4 -1.1(4) . . . . ?
C7 C8 C9 C10 178.8(3) . . . . ?
C7 C6 C5 C4 -1.2(5) . . . . ?
C7 C6 C5 C1 177.8(3) . . . . ?
C9 C8 C7 C6 0.6(5) . . . . ?
C9 C4 C5 C6 0.6(4) . . . . ?
C9 C4 C5 C1 -178.4(3) . . . . ?
C9 C4 C3 C2 178.8(3) . . . . ?
C9 C4 C3 C12 0.1(5) . . . . ?
C9 C10 C11 C12 -1.3(5) . . . . ?
C4 C9 C10 C8 -179.6(3) . . . 2_756 ?
C4 C9 C10 C11 1.1(4) . . . . ?
C4 C5 C1 O1 177.9(3) . . . . ?
C4 C5 C1 N1 -2.0(5) . . . . ?
C4 C3 C2 O2 -177.8(4) . . . . ?
C4 C3 C2 N1 1.1(5) . . . . ?
C4 C3 C12 C11 -0.3(5) . . . . ?
C10 C8 C7 C6 179.8(3) 2_756 . . . ?
C10 C8 C9 C4 179.6(3) 2_756 . . . ?
C10 C8 C9 C10 -0.4(5) 2_756 . . . ?
C10 C9 C4 C5 -179.4(3) . . . . ?
C10 C9 C4 C3 -0.5(4) . . . . ?
C10 C11 C12 C3 0.9(6) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
C5 C4 C3 C2 -2.3(5) . . . . ?
C5 C4 C3 C12 178.9(3) . . . . ?
C1 N1 C2 O2 178.5(4) . . . . ?
C1 N1 C2 C3 -0.4(5) . . . . ?
C1 N1 C13 C14 -85.7(4) . . . . ?
C3 C4 C5 C6 -178.3(3) . . . . ?
C3 C4 C5 C1 2.7(4) . . . . ?
C2 N1 C1 O1 -179.0(3) . . . . ?
C2 N1 C1 C5 0.8(5) . . . . ?
C2 N1 C13 C14 89.8(4) . . . . ?
C2 C3 C12 C11 -179.0(3) . . . . ?
C12 C3 C2 O2 0.9(6) . . . . ?
C12 C3 C2 N1 179.9(3) . . . . ?
C13 N1 C1 O1 -3.9(5) . . . . ?
C13 N1 C1 C5 176.0(3) . . . . ?
C13 N1 C2 O2 3.4(6) . . . . ?
C13 N1 C2 C3 -175.5(3) . . . . ?
C13 C14 C15 C16 -179.4(3) . . . . ?
C15 C16 C17 C18 179.4(4) . . . . ?
C17 C16 C15 C14 178.7(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_C6_440K
_database_code_depnum_ccdc_archive 'CCDC 2412030'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-12-20 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
_audit_creation_date             2024-11-26
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         C36H34N2O4
_chemical_oxdiff_usercomment     440K
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                   4.8395(10)
_cell_length_b                   8.5365(13)
_cell_length_c                   18.158(3)
_cell_angle_alpha                84.478(12)
_cell_angle_beta                 83.426(15)
_cell_angle_gamma                81.495(16)
_cell_volume                     734.6(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    904
_cell_measurement_temperature    440.00(14)
_cell_measurement_theta_max      71.5980
_cell_measurement_theta_min      5.2460
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.748
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.808
_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   'Data were collected at 440 K.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 5 3 0.0591
0 -5 -3 0.0749
3 3 2 0.1669
-3 -4 -2 0.2204
0 1 -11 0.0515
0 -1 11 0.0010

_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.047
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
-0.6571 5.0953 2.7350 -0.0071 0.0692 0.9976
0.1873 -5.3995 -2.9692 0.0175 -0.2217 -0.9875
2.8966 2.8731 1.8681 -0.0789 0.9904 0.1137
-2.6770 -3.5530 -2.2199 0.0768 -0.9612 -0.2649
-0.3319 0.7856 -11.4445 -0.9902 -0.1371 0.0002
0.1485 -0.8774 11.3995 0.9968 0.0792 0.0090

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4371
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.091
_diffrn_reflns_theta_min         4.919
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      440.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0294
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00 -43.00   1.00    8.00    --  -35.62 125.00 -30.00   43
  2  ω     21.00  99.00   1.00    8.00    --   35.62  57.00 -60.00   78
  3  ω      8.00  67.00   1.00    8.00    --   35.62-125.00 150.00   59
  4  ω     17.00  66.00   1.00    8.00    --   35.62  38.00 -90.00   49
  5  ω     53.00 105.00   1.00    8.00    --   35.62  38.00   0.00   52
  6  ω      8.00  43.00   1.00    8.00    --   35.62-125.00-150.00   35
  7  ω     55.00  86.00   1.00    8.00    --   35.62-125.00-120.00   31
  8  ω     17.00  99.00   1.00    8.00    --   35.62  38.00  90.00   82
  9  ω     46.00  89.00   1.00   35.00    --  109.02 -61.00  30.00   43
 10  ω     66.00 109.00   1.00   35.00    --  109.02-111.00-150.00   43
 11  ω     42.00 100.00   1.00   35.00    --  109.02-111.00 150.00   58
 12  ω    100.00 157.00   1.00   35.00    --  109.02  61.00 -30.00   57
 13  ω    118.00 149.00   1.00   35.00    --  109.02  77.00 -90.00   31
 14  ω     43.00  96.00   1.00   35.00    --  109.02 -45.00 120.00   53
 15  ω     86.00 122.00   1.00   35.00    --  109.02  77.00 -60.00   36
 16  ω     72.00 102.00   1.00   35.00    --  109.02 -94.00 -60.00   30
 17  ω    102.00 127.00   1.00   35.00    --  109.02 -61.00  30.00   25
 18  ω     40.00 131.00   1.00   35.00    --  109.02 178.00 150.00   91
 19  ω     77.00 104.00   1.00   35.00    --  109.02 -94.00  30.00   27
 20  ω     51.00 125.00   1.00   35.00    --  109.02 -45.00-180.00   74
 21  ω     58.00 135.00   1.00   35.00    --  109.02 -77.00-120.00   77
 22  ω    106.00 132.00   1.00   35.00    --  109.02  45.00 150.00   26
 23  ω     95.00 142.00   1.00   35.00    --  109.02  45.00  90.00   47
 24  ω     83.00 158.00   1.00   35.00    --  109.02  77.00   0.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0312945000
_diffrn_orient_matrix_UB_12      -0.0505022000
_diffrn_orient_matrix_UB_13      0.0839647000
_diffrn_orient_matrix_UB_21      0.2905157000
_diffrn_orient_matrix_UB_22      0.0473900000
_diffrn_orient_matrix_UB_23      0.0068101000
_diffrn_orient_matrix_UB_31      -0.1389515000
_diffrn_orient_matrix_UB_32      0.1694677000
_diffrn_orient_matrix_UB_33      0.0156473000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1116
_reflns_number_total             2807
_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       
'CrysAlisPro system (CCD 43.109a (release 21-02-2024))'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2807
_refine_ls_number_restraints     187
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0797
_refine_ls_restrained_S_all      0.984
_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)+(0.1643P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2516
_refine_ls_wR_factor_ref         0.3256
_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
 C3-C2 \\sim C12-C3 \\sim C11-C12 \\sim C10-C11 \\sim C9-C10 \\sim C9-C4 \\sim
C3-C4 \\sim C4-C5 \\sim C1-C5 ~
 C6-C5 \\sim C6-C7 \\sim C8-C9 \\sim C7-C8
 with sigma of 0.02
 C13-C1 \\sim C13-C2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 2A
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
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C14(H14A,H14B), C13(H13A,H13B), C17(H17A,H17B)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C11(H11), C12(H12)
4.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
O2 O -0.0412(6) 0.4339(3) 0.61726(17) 0.1339(10) Uani 1 1 d . . . . .
O1 O 0.2369(7) 0.0418(4) 0.79015(18) 0.1627(13) Uani 1 1 d . . . . .
N1 N 0.0978(6) 0.2387(4) 0.70384(18) 0.1135(9) Uani 1 1 d . . . . .
C4 C 0.5440(5) 0.1181(3) 0.60175(16) 0.0891(8) Uani 1 1 d D U . . .
C7 C 0.9113(7) -0.1481(4) 0.6444(2) 0.1095(10) Uani 1 1 d D U . . .
H7 H 1.031700 -0.237822 0.659496 0.131 Uiso 1 1 calc R U . . .
C8 C 0.9598(5) -0.0769(3) 0.57372(16) 0.0876(8) Uani 1 1 d D U . . .
C10 C 0.8044(5) 0.1365(3) 0.47862(16) 0.0853(8) Uani 1 1 d D U . . .
C15 C -0.2137(12) 0.5191(8) 0.8503(3) 0.182(2) Uani 1 1 d . U . . .
H15A H -0.290098 0.444770 0.888202 0.218 Uiso 1 1 calc R U . . .
H15B H -0.366582 0.571763 0.822823 0.218 Uiso 1 1 calc R U . . .
C3 C 0.3535(6) 0.2517(3) 0.58019(19) 0.0928(8) Uani 1 1 d D U . . .
C2 C 0.1233(7) 0.3160(4) 0.6328(2) 0.1062(10) Uani 1 1 d D U . . .
C6 C 0.6882(8) -0.0900(4) 0.6937(2) 0.1157(11) Uani 1 1 d D U . . .
H6 H 0.661589 -0.141058 0.741063 0.139 Uiso 1 1 calc R U . . .
C9 C 0.7715(5) 0.0591(3) 0.55108(16) 0.0844(8) Uani 1 1 d D U . . .
C5 C 0.5054(7) 0.0425(4) 0.67340(19) 0.1014(9) Uani 1 1 d D U . . .
C16 C -0.0942(14) 0.6434(8) 0.8880(4) 0.204(3) Uani 1 1 d . U . . .
H16A H 0.055027 0.589876 0.916528 0.245 Uiso 1 1 calc R U . . .
H16B H -0.011701 0.715091 0.849858 0.245 Uiso 1 1 calc R U . . .
C11 C 0.6108(6) 0.2659(3) 0.45951(19) 0.0956(9) Uani 1 1 d D U . . .
H11 H 0.630903 0.316399 0.411866 0.115 Uiso 1 1 calc R U . . .
C12 C 0.3881(6) 0.3225(3) 0.5092(2) 0.0997(9) Uani 1 1 d D U . . .
H12 H 0.260808 0.409237 0.494318 0.120 Uiso 1 1 calc R U . . .
C14 C -0.0055(10) 0.4313(6) 0.7996(3) 0.1550(17) Uani 1 1 d . U . . .
H14A H 0.145135 0.377108 0.827490 0.186 Uiso 1 1 calc R U . . .
H14B H 0.074140 0.506256 0.762635 0.186 Uiso 1 1 calc R U . . .
C13 C -0.1218(8) 0.3073(5) 0.7592(3) 0.1334(13) Uani 1 1 d D U . . .
H13A H -0.180828 0.223886 0.795047 0.160 Uiso 1 1 calc R U . . .
H13B H -0.283710 0.357839 0.734734 0.160 Uiso 1 1 calc R U . . .
C1 C 0.2745(8) 0.1028(5) 0.7273(2) 0.1181(11) Uani 1 1 d D U . . .
C18 C -0.177(2) 0.8353(13) 0.9763(7) 0.334(6) Uani 1 1 d . U . . .
H18A H 0.015390 0.839121 0.956759 0.501 Uiso 1 1 calc R U . . .
H18B H -0.184140 0.795584 1.027663 0.501 Uiso 1 1 calc R U . . .
H18C H -0.280254 0.940124 0.972020 0.501 Uiso 1 1 calc R U . . .
C17 C -0.295(2) 0.7345(12) 0.9360(6) 0.288(5) Uani 1 1 d . U . . .
H17A H -0.431939 0.798100 0.906576 0.346 Uiso 1 1 calc R U . . .
H17B H -0.392716 0.662759 0.970710 0.346 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.219(4) . ?
O1 C1 1.213(5) . ?
N1 C2 1.393(5) . ?
N1 C13 1.473(5) . ?
N1 C1 1.397(5) . ?
C4 C3 1.410(4) . ?
C4 C9 1.416(4) . ?
C4 C5 1.401(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(4) . ?
C7 C6 1.385(5) . ?
C8 C10 1.462(4) 2_756 ?
C8 C9 1.425(4) . ?
C10 C9 1.417(4) . ?
C10 C11 1.383(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.531(7) . ?
C15 C14 1.456(7) . ?
C3 C2 1.460(5) . ?
C3 C12 1.374(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.377(4) . ?
C5 C1 1.466(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.421(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(4) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.547(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 C17 1.401(11) . ?
C17 H17A 0.9700 . ?
C17 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
C2 N1 C13 118.3(3) . . ?
C2 N1 C1 124.3(3) . . ?
C1 N1 C13 117.3(3) . . ?
C3 C4 C9 120.3(3) . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 C9 120.0(3) . . ?
C8 C7 H7 119.1 . . ?
C8 C7 C6 121.9(3) . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C10 122.4(3) . 2_756 ?
C7 C8 C9 118.4(3) . . ?
C9 C8 C10 119.2(3) . 2_756 ?
C9 C10 C8 119.2(2) . 2_756 ?
C11 C10 C8 122.0(3) . 2_756 ?
C11 C10 C9 118.8(3) . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C14 C15 C16 113.1(5) . . ?
C4 C3 C2 120.7(3) . . ?
C12 C3 C4 119.4(3) . . ?
C12 C3 C2 120.0(3) . . ?
O2 C2 N1 119.7(3) . . ?
O2 C2 C3 122.9(4) . . ?
N1 C2 C3 117.4(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C4 C9 C8 119.4(3) . . ?
C4 C9 C10 119.0(3) . . ?
C10 C9 C8 121.6(3) . . ?
C4 C5 C1 121.0(3) . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 C1 119.4(3) . . ?
C15 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C17 C16 C15 114.4(7) . . ?
C17 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C10 C11 H11 119.0 . . ?
C10 C11 C12 122.0(3) . . ?
C12 C11 H11 119.0 . . ?
C3 C12 C11 120.5(3) . . ?
C3 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C15 C14 C13 114.3(4) . . ?
H14A C14 H14B 107.6 . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
N1 C13 C14 109.5(3) . . ?
N1 C13 H13A 109.8 . . ?
N1 C13 H13B 109.8 . . ?
C14 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
O1 C1 N1 120.3(4) . . ?
O1 C1 C5 122.9(4) . . ?
N1 C1 C5 116.9(3) . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 C16 113.6(9) . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?

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
C4 C3 C2 O2 177.8(3) . . . . ?
C4 C3 C2 N1 -1.1(4) . . . . ?
C4 C3 C12 C11 -1.4(4) . . . . ?
C4 C5 C1 O1 -178.9(4) . . . . ?
C4 C5 C1 N1 -0.3(5) . . . . ?
C7 C8 C9 C4 0.8(4) . . . . ?
C7 C8 C9 C10 -178.6(2) . . . . ?
C7 C6 C5 C4 0.7(5) . . . . ?
C7 C6 C5 C1 -178.9(3) . . . . ?
C8 C7 C6 C5 0.0(6) . . . . ?
C8 C10 C9 C4 179.51(19) 2_756 . . . ?
C8 C10 C9 C8 -1.1(4) 2_756 . . . ?
C8 C10 C11 C12 -179.8(2) 2_756 . . . ?
C10 C8 C9 C4 -179.51(19) 2_756 . . . ?
C10 C8 C9 C10 1.1(4) 2_756 . . . ?
C10 C11 C12 C3 0.6(4) . . . . ?
C15 C16 C17 C18 173.4(9) . . . . ?
C15 C14 C13 N1 173.9(4) . . . . ?
C3 C4 C9 C8 -179.3(2) . . . . ?
C3 C4 C9 C10 0.1(4) . . . . ?
C3 C4 C5 C6 178.6(3) . . . . ?
C3 C4 C5 C1 -1.9(4) . . . . ?
C2 N1 C13 C14 -87.5(4) . . . . ?
C2 N1 C1 O1 -179.5(4) . . . . ?
C2 N1 C1 C5 1.9(5) . . . . ?
C2 C3 C12 C11 177.9(2) . . . . ?
C6 C7 C8 C10 179.6(3) . . . 2_756 ?
C6 C7 C8 C9 -0.8(5) . . . . ?
C6 C5 C1 O1 0.6(6) . . . . ?
C6 C5 C1 N1 179.3(3) . . . . ?
C9 C4 C3 C2 -178.2(2) . . . . ?
C9 C4 C3 C12 1.0(4) . . . . ?
C9 C4 C5 C6 -0.7(4) . . . . ?
C9 C4 C5 C1 178.9(2) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C5 C4 C3 C2 2.6(4) . . . . ?
C5 C4 C3 C12 -178.2(2) . . . . ?
C5 C4 C9 C8 -0.1(4) . . . . ?
C5 C4 C9 C10 179.3(2) . . . . ?
C16 C15 C14 C13 -178.6(5) . . . . ?
C11 C10 C9 C4 -0.8(3) . . . . ?
C11 C10 C9 C8 178.5(2) . . . . ?
C12 C3 C2 O2 -1.5(5) . . . . ?
C12 C3 C2 N1 179.7(2) . . . . ?
C14 C15 C16 C17 178.1(8) . . . . ?
C13 N1 C2 O2 -2.7(5) . . . . ?
C13 N1 C2 C3 176.2(3) . . . . ?
C13 N1 C1 O1 3.2(6) . . . . ?
C13 N1 C1 C5 -175.5(3) . . . . ?
C1 N1 C2 O2 179.9(3) . . . . ?
C1 N1 C2 C3 -1.2(5) . . . . ?
C1 N1 C13 C14 90.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.365
_oxdiff_exptl_absorpt_empirical_full_min 0.198
####################################################################### 
# 
# 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_C6_100K
_database_code_depnum_ccdc_archive 'CCDC 2421994'
loop_
_audit_author_name
_audit_author_address
'Paulina Ratajczyk'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2025-02-06 deposited with the CCDC.	2025-05-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT026_PDI_C6_100K         
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        30% Check 
RESPONSE: Due to the overall poor diffraction quality
of the needle-shaped crystal and low symmetry.
;
# end Validation Reply Form
loop_
_audit_creation_date
2025-02-06
_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-C6
_chemical_name_systematic        N,N-Dihexyl-3,4,9,10-perylenedicarboximide
_chemical_formula_moiety         'C36 H34 N2 O4'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_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                   4.7056(19)
_cell_length_b                   8.514(3)
_cell_length_c                   17.281(5)
_cell_angle_alpha                81.34(3)
_cell_angle_beta                 85.64(3)
_cell_angle_gamma                83.89(3)
_cell_volume                     679.3(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    438
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.1110
_cell_measurement_theta_min      3.6190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.618
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.021
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_av_unetI/netI     0.2394
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.814
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4969
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.360
_diffrn_reflns_theta_min         3.585
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.814
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                913
_reflns_number_total             3047
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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         0.359
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3047
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2490
_refine_ls_R_factor_gt           0.0800
_refine_ls_restrained_S_all      0.957
_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)+(0.0409P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.2278
_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.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C16(H16A,H16B), C15(H15A,H15B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C6(H6), C7(H7), C12(H12)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 -0.0233(6) 0.4237(4) 0.6171(2) 0.0331(9) Uani 1 1 d . . . . .
O2 O 0.2539(7) 0.0116(4) 0.8042(2) 0.0393(10) Uani 1 1 d . . . . .
N1 N 0.1096(7) 0.2143(5) 0.7100(2) 0.0231(10) Uani 1 1 d . . . . .
C8 C 0.8059(8) 0.1406(5) 0.4756(3) 0.0193(11) Uani 1 1 d . . . . .
C11 C 0.9165(9) -0.1636(5) 0.6537(3) 0.0234(11) Uani 1 1 d . . . . .
H11 H 1.039248 -0.256031 0.671123 0.028 Uiso 1 1 calc R U . . .
C6 C 0.3961(9) 0.3234(5) 0.5057(3) 0.0255(12) Uani 1 1 d . . . . .
H6 H 0.266325 0.413453 0.489267 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6144(8) 0.2739(5) 0.4533(3) 0.0219(11) Uani 1 1 d . . . . .
H7 H 0.633584 0.331361 0.401944 0.026 Uiso 1 1 calc R U . . .
C5 C 0.3647(9) 0.2444(5) 0.5807(3) 0.0214(11) Uani 1 1 d . . . . .
C10 C 0.9618(9) -0.0863(5) 0.5793(3) 0.0212(11) Uani 1 1 d . . . . .
C4 C 0.5525(9) 0.1062(5) 0.6061(3) 0.0206(11) Uani 1 1 d . . . . .
C3 C 0.5152(9) 0.0250(5) 0.6813(3) 0.0229(12) Uani 1 1 d . . . . .
C9 C 0.7759(9) 0.0545(5) 0.5523(3) 0.0222(11) Uani 1 1 d . . . . .
C1 C 0.1365(10) 0.3023(6) 0.6361(3) 0.0278(12) Uani 1 1 d . . . . .
C13 C -0.1081(9) 0.2800(6) 0.7666(3) 0.0294(13) Uani 1 1 d . . . . .
H13A H -0.168034 0.192736 0.807158 0.035 Uiso 1 1 calc R U . . .
H13B H -0.278979 0.329576 0.738861 0.035 Uiso 1 1 calc R U . . .
C12 C 0.6935(9) -0.1104(5) 0.7051(3) 0.0264(12) Uani 1 1 d . . . . .
H12 H 0.665370 -0.167711 0.756254 0.032 Uiso 1 1 calc R U . . .
C2 C 0.2856(10) 0.0793(6) 0.7372(3) 0.0250(12) Uani 1 1 d . . . . .
C14 C 0.0183(9) 0.4046(6) 0.8053(3) 0.0343(14) Uani 1 1 d . . . . .
H14A H 0.106315 0.481298 0.763996 0.041 Uiso 1 1 calc R U . . .
H14B H 0.171680 0.350633 0.838800 0.041 Uiso 1 1 calc R U . . .
C16 C -0.0787(9) 0.6208(5) 0.8931(3) 0.0331(14) Uani 1 1 d . . . . .
H16A H 0.009277 0.697114 0.851577 0.040 Uiso 1 1 calc R U . . .
H16B H 0.074524 0.567579 0.926850 0.040 Uiso 1 1 calc R U . . .
C15 C -0.2040(9) 0.4966(5) 0.8554(3) 0.0318(13) Uani 1 1 d . . . . .
H15A H -0.358238 0.549850 0.822014 0.038 Uiso 1 1 calc R U . . .
H15B H -0.290875 0.420003 0.897000 0.038 Uiso 1 1 calc R U . . .
C17 C -0.3019(10) 0.7131(6) 0.9426(3) 0.0351(14) Uani 1 1 d . . . . .
H17A H -0.452461 0.769612 0.908796 0.042 Uiso 1 1 calc R U . . .
H17B H -0.393612 0.637227 0.983572 0.042 Uiso 1 1 calc R U . . .
C18 C -0.1659(10) 0.8336(6) 0.9812(3) 0.0423(16) Uani 1 1 d . . . . .
H18A H -0.009097 0.778740 1.012178 0.063 Uiso 1 1 calc R U . . .
H18B H -0.310244 0.885008 1.015666 0.063 Uiso 1 1 calc R U . . .
H18C H -0.090887 0.914730 0.940703 0.063 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.229(5) . ?
O2 C2 1.220(6) . ?
N1 C1 1.385(6) . ?
N1 C13 1.486(5) . ?
N1 C2 1.386(5) . ?
C8 C7 1.398(6) . ?
C8 C10 1.476(6) 2_756 ?
C8 C9 1.419(7) . ?
C11 H11 0.9500 . ?
C11 C10 1.364(6) . ?
C11 C12 1.405(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(5) . ?
C6 C5 1.372(6) . ?
C7 H7 0.9500 . ?
C5 C4 1.429(6) . ?
C5 C1 1.478(6) . ?
C10 C9 1.446(6) . ?
C4 C3 1.385(7) . ?
C4 C9 1.429(6) . ?
C3 C12 1.381(6) . ?
C3 C2 1.477(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.528(6) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.533(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.513(6) . ?
C16 C17 1.530(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.523(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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 C13 116.6(4) . . ?
C1 N1 C2 125.2(4) . . ?
C2 N1 C13 117.9(4) . . ?
C7 C8 C10 121.3(5) . 2_756 ?
C7 C8 C9 119.6(4) . . ?
C9 C8 C10 119.1(4) . 2_756 ?
C10 C11 H11 119.0 . . ?
C10 C11 C12 121.9(4) . . ?
C12 C11 H11 119.0 . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(4) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 C8 120.6(5) . . ?
C6 C7 H7 119.7 . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 C1 120.2(4) . . ?
C4 C5 C1 119.4(5) . . ?
C11 C10 C8 122.7(4) . 2_756 ?
C11 C10 C9 119.4(4) . . ?
C9 C10 C8 117.9(4) . 2_756 ?
C3 C4 C5 120.1(4) . . ?
C3 C4 C9 121.4(4) . . ?
C9 C4 C5 118.5(4) . . ?
C4 C3 C2 121.4(4) . . ?
C12 C3 C4 119.9(4) . . ?
C12 C3 C2 118.7(5) . . ?
C8 C9 C10 123.0(4) . . ?
C8 C9 C4 119.7(4) . . ?
C4 C9 C10 117.4(5) . . ?
O1 C1 N1 121.3(4) . . ?
O1 C1 C5 121.2(5) . . ?
N1 C1 C5 117.4(4) . . ?
N1 C13 H13A 109.7 . . ?
N1 C13 H13B 109.7 . . ?
N1 C13 C14 109.6(4) . . ?
H13A C13 H13B 108.2 . . ?
C14 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C11 C12 H12 120.0 . . ?
C3 C12 C11 120.0(5) . . ?
C3 C12 H12 120.0 . . ?
O2 C2 N1 121.2(4) . . ?
O2 C2 C3 122.3(4) . . ?
N1 C2 C3 116.5(4) . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C13 C14 C15 113.2(4) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H16A C16 H16B 107.8 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C15 C16 C17 112.9(4) . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 C14 113.1(4) . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C16 111.2(4) . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 171.4(4) . . . . ?
C8 C10 C9 C8 0.7(7) 2_756 . . . ?
C8 C10 C9 C4 -179.8(4) 2_756 . . . ?
C11 C10 C9 C8 -179.1(4) . . . . ?
C11 C10 C9 C4 0.4(6) . . . . ?
C6 C5 C4 C3 -178.5(4) . . . . ?
C6 C5 C4 C9 1.2(7) . . . . ?
C6 C5 C1 O1 -2.1(7) . . . . ?
C6 C5 C1 N1 177.8(4) . . . . ?
C7 C8 C9 C10 178.8(4) . . . . ?
C7 C8 C9 C4 -0.7(6) . . . . ?
C7 C6 C5 C4 -1.6(7) . . . . ?
C7 C6 C5 C1 178.1(4) . . . . ?
C5 C6 C7 C8 0.9(7) . . . . ?
C5 C4 C3 C12 178.6(4) . . . . ?
C5 C4 C3 C2 -0.8(7) . . . . ?
C5 C4 C9 C8 0.0(6) . . . . ?
C5 C4 C9 C10 -179.6(4) . . . . ?
C10 C8 C7 C6 179.8(4) 2_756 . . . ?
C10 C8 C9 C10 -0.7(7) 2_756 . . . ?
C10 C8 C9 C4 179.8(4) 2_756 . . . ?
C10 C11 C12 C3 -1.0(7) . . . . ?
C4 C5 C1 O1 177.7(4) . . . . ?
C4 C5 C1 N1 -2.4(7) . . . . ?
C4 C3 C12 C11 1.5(7) . . . . ?
C4 C3 C2 O2 -178.2(5) . . . . ?
C4 C3 C2 N1 0.5(6) . . . . ?
C3 C4 C9 C8 179.7(5) . . . . ?
C3 C4 C9 C10 0.1(6) . . . . ?
C9 C8 C7 C6 0.3(6) . . . . ?
C9 C4 C3 C12 -1.1(7) . . . . ?
C9 C4 C3 C2 179.5(4) . . . . ?
C1 N1 C13 C14 -83.1(5) . . . . ?
C1 N1 C2 O2 177.4(5) . . . . ?
C1 N1 C2 C3 -1.3(7) . . . . ?
C1 C5 C4 C3 1.8(7) . . . . ?
C1 C5 C4 C9 -178.5(4) . . . . ?
C13 N1 C1 O1 -4.0(7) . . . . ?
C13 N1 C1 C5 176.1(4) . . . . ?
C13 N1 C2 O2 3.6(7) . . . . ?
C13 N1 C2 C3 -175.1(4) . . . . ?
C13 C14 C15 C16 -179.5(5) . . . . ?
C12 C11 C10 C8 -179.8(4) . . . 2_756 ?
C12 C11 C10 C9 0.0(7) . . . . ?
C12 C3 C2 O2 2.4(7) . . . . ?
C12 C3 C2 N1 -179.0(4) . . . . ?
C2 N1 C1 O1 -177.8(4) . . . . ?
C2 N1 C1 C5 2.2(7) . . . . ?
C2 N1 C13 C14 91.2(5) . . . . ?
C2 C3 C12 C11 -179.1(4) . . . . ?
C15 C16 C17 C18 178.5(5) . . . . ?
C17 C16 C15 C14 179.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
