# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_DPA-4-Per
_database_code_depnum_ccdc_archive 'CCDC 1881912'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius-Maximilians-Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2018-11-28 deposited with the CCDC.	2019-06-21 downloaded from the CCDC.
;

_audit_creation_date             2017-07-11

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_formula_moiety         'C76 H64 N4 O8'
_chemical_formula_sum            'C76 H64 N4 O8'
_chemical_formula_weight         1161.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.025(7)
_cell_length_b                   11.576(7)
_cell_length_c                   18.285(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.45(2)
_cell_angle_gamma                90
_cell_volume                     2955(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4322
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      24.68
_cell_special_details            
;
To simulate systematic errors the final estimation of uncertainties
in unit cell parameters was based on 32 Monte-Carlo simulations.
;


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.132
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6719
_exptl_absorpt_correction_T_max  0.7454
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 3.00 3.00 0.1520
0.00 -2.00 -1.00 0.1280
-1.00 1.00 -1.00 0.1790
1.00 -1.00 1.00 0.1460
-1.00 3.00 0.00 0.1560
0.00 -3.00 -2.00 0.1280
-2.00 0.00 -3.00 0.1880
2.00 0.00 3.00 0.1780
0.00 2.00 1.00 0.1460
0.00 3.00 2.00 0.1460
-2.00 3.00 -1.00 0.1620
2.00 -3.00 1.00 0.1470
0.00 -1.00 -1.00 0.1260
1.00 0.00 2.00 0.1820
-1.00 0.00 1.00 0.0660
1.00 0.00 -1.00 0.0280
1.00 0.00 -2.00 0.0570
-1.00 1.00 2.00 0.1130
-1.00 1.00 1.00 0.1350
-1.00 -1.00 -1.00 0.1670
3.00 3.00 2.00 0.1410
-1.00 3.00 -2.00 0.1510
1.00 3.00 0.00 0.1530
0.00 3.00 -1.00 0.1500
1.00 3.00 -2.00 0.1340

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_source                   'rotating-anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            23828
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.921
_diffrn_reflns_theta_max         26.511
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6104
_reflns_number_gt                4063
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 ver. 2016.1-0 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.37A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.37A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.5086P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6104
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.10273(10) -0.01994(12) 0.81006(7) 0.0330(3) Uani 1 1 d . . . . .
C1 C 0.15311(13) 0.31975(16) 0.63629(9) 0.0215(4) Uani 1 1 d . . . . .
N1 N 0.18100(11) 0.22491(14) 0.68136(8) 0.0264(4) Uani 1 1 d . . . . .
O2 O 0.55597(9) 0.05952(12) 0.70713(7) 0.0327(3) Uani 1 1 d . . . . .
C2 C 0.11119(13) 0.15969(16) 0.71581(10) 0.0244(4) Uani 1 1 d . . . . .
N2 N 0.28949(11) 0.76253(13) 0.49470(9) 0.0292(4) Uani 1 1 d . . . . .
O3 O 0.68055(9) 0.75560(11) 0.57822(7) 0.0322(3) Uani 1 1 d . . . . .
C3 C 0.27753(13) 0.18565(16) 0.68869(10) 0.0234(4) Uani 1 1 d . . . . .
C4 C 0.22812(13) 0.67268(15) 0.51080(10) 0.0232(4) Uani 1 1 d . . . . .
O4 O 0.10201(9) 1.15317(11) 0.37841(7) 0.0302(3) Uani 1 1 d . . . . .
C7 C 0.21490(13) 0.40859(15) 0.62519(9) 0.0216(4) Uani 1 1 d . . . . .
H7 H 0.2768 0.4094 0.6512 0.026 Uiso 1 1 calc R U . . .
C6 C 0.24733(13) 0.86929(15) 0.46860(11) 0.0252(4) Uani 1 1 d . . . . .
C5 C 0.38942(13) 0.75940(16) 0.51410(10) 0.0242(4) Uani 1 1 d . . . . .
C8 C 0.18775(12) 0.49888(15) 0.57558(9) 0.0193(4) Uani 1 1 d . . . . .
C9 C 0.25298(13) 0.58798(15) 0.56204(10) 0.0221(4) Uani 1 1 d . . . . .
H9 H 0.3146 0.5894 0.5886 0.027 Uiso 1 1 calc R U . . .
C10 C 0.13623(13) 0.66906(15) 0.47201(10) 0.0219(4) Uani 1 1 d . . . . .
H10 H 0.1204 0.7250 0.4348 0.026 Uiso 1 1 calc R U . . .
C11 C 0.06884(12) 0.58820(15) 0.48579(9) 0.0185(4) Uani 1 1 d . . . . .
C12 C 0.09362(12) 0.50022(14) 0.53849(9) 0.0174(4) Uani 1 1 d . . . . .
C13 C 0.02851(12) 0.41070(15) 0.55315(9) 0.0185(4) Uani 1 1 d . . . . .
C14 C 0.05970(13) 0.32207(16) 0.59989(9) 0.0223(4) Uani 1 1 d . . . . .
H14 H 0.0170 0.2606 0.6078 0.027 Uiso 1 1 calc R U . . .
C19 C 0.11170(13) 0.03992(17) 0.71467(10) 0.0262(4) Uani 1 1 d . . . . .
H19 H 0.1599 0.0007 0.6912 0.031 Uiso 1 1 calc R U . . .
C15 C 0.04132(14) 0.21525(17) 0.75123(10) 0.0296(5) Uani 1 1 d . . . . .
H15 H 0.0420 0.2971 0.7549 0.035 Uiso 1 1 calc R U . . .
C16 C -0.02961(15) 0.15278(17) 0.78145(10) 0.0298(5) Uani 1 1 d . . . . .
H16 H -0.0789 0.1919 0.8038 0.036 Uiso 1 1 calc R U . . .
C17 C -0.02844(14) 0.03300(17) 0.77902(10) 0.0265(4) Uani 1 1 d . . . . .
C20 C -0.10568(16) -0.14344(17) 0.80857(12) 0.0367(5) Uani 1 1 d . . . . .
H20A H -0.1616 -0.1704 0.8320 0.055 Uiso 1 1 calc R U . . .
H20B H -0.0472 -0.1743 0.8352 0.055 Uiso 1 1 calc R U . . .
H20C H -0.1102 -0.1702 0.7575 0.055 Uiso 1 1 calc R U . . .
C21 C 0.31945(13) 0.15084(16) 0.75675(10) 0.0256(4) Uani 1 1 d . . . . .
H21 H 0.2847 0.1581 0.7986 0.031 Uiso 1 1 calc R U . . .
C22 C 0.41149(13) 0.10555(17) 0.76474(10) 0.0260(4) Uani 1 1 d . . . . .
H22 H 0.4383 0.0788 0.8114 0.031 Uiso 1 1 calc R U . . .
C23 C 0.46381(13) 0.09955(16) 0.70490(10) 0.0247(4) Uani 1 1 d . . . . .
C24 C 0.42269(14) 0.13478(16) 0.63650(10) 0.0252(4) Uani 1 1 d . . . . .
H24 H 0.4586 0.1307 0.5951 0.030 Uiso 1 1 calc R U . . .
C25 C 0.33011(14) 0.17568(16) 0.62833(10) 0.0252(4) Uani 1 1 d . . . . .
H25 H 0.3019 0.1973 0.5810 0.030 Uiso 1 1 calc R U . . .
C26 C 0.60173(15) 0.0294(2) 0.77710(12) 0.0463(6) Uani 1 1 d . . . . .
H26A H 0.6677 0.0052 0.7719 0.070 Uiso 1 1 calc R U . . .
H26B H 0.5668 -0.0342 0.7978 0.070 Uiso 1 1 calc R U . . .
H26C H 0.6023 0.0964 0.8099 0.070 Uiso 1 1 calc R U . . .
C27 C 0.44319(13) 0.66544(16) 0.49649(10) 0.0255(4) Uani 1 1 d . . . . .
H27 H 0.4127 0.6026 0.4703 0.031 Uiso 1 1 calc R U . . .
C28 C 0.54065(13) 0.66109(15) 0.51621(10) 0.0238(4) Uani 1 1 d . . . . .
H28 H 0.5765 0.5953 0.5042 0.029 Uiso 1 1 calc R U . . .
C29 C 0.58585(13) 0.75310(16) 0.55354(10) 0.0238(4) Uani 1 1 d . . . . .
C30 C 0.53302(13) 0.85018(16) 0.56856(10) 0.0264(4) Uani 1 1 d . . . . .
H30 H 0.5642 0.9150 0.5921 0.032 Uiso 1 1 calc R U . . .
C31 C 0.43597(13) 0.85300(16) 0.54960(11) 0.0263(4) Uani 1 1 d . . . . .
H31 H 0.4002 0.9194 0.5608 0.032 Uiso 1 1 calc R U . . .
C32 C 0.73390(14) 0.65356(18) 0.56906(12) 0.0360(5) Uani 1 1 d . . . . .
H32A H 0.8007 0.6658 0.5885 0.054 Uiso 1 1 calc R U . . .
H32B H 0.7313 0.6344 0.5167 0.054 Uiso 1 1 calc R U . . .
H32C H 0.7067 0.5899 0.5956 0.054 Uiso 1 1 calc R U . . .
C33 C 0.26136(14) 0.90846(16) 0.39903(11) 0.0302(5) Uani 1 1 d . . . . .
H33 H 0.3044 0.8692 0.3705 0.036 Uiso 1 1 calc R U . . .
C34 C 0.21280(14) 1.00454(17) 0.37113(12) 0.0325(5) Uani 1 1 d . . . . .
H34 H 0.2225 1.0317 0.3234 0.039 Uiso 1 1 calc R U . . .
C35 C 0.14992(13) 1.06169(15) 0.41250(10) 0.0249(4) Uani 1 1 d . . . . .
C36 C 0.13886(14) 1.02631(17) 0.48319(11) 0.0276(4) Uani 1 1 d . . . . .
H36 H 0.0978 1.0673 0.5125 0.033 Uiso 1 1 calc R U . . .
C37 C 0.18888(14) 0.92963(17) 0.51077(11) 0.0297(5) Uani 1 1 d . . . . .
H37 H 0.1824 0.9050 0.5596 0.036 Uiso 1 1 calc R U . . .
C38 C 0.02436(16) 1.1983(2) 0.41359(12) 0.0414(6) Uani 1 1 d . . . . .
H38A H -0.0112 1.2537 0.3809 0.062 Uiso 1 1 calc R U . . .
H38B H 0.0488 1.2374 0.4591 0.062 Uiso 1 1 calc R U . . .
H38C H -0.0183 1.1351 0.4251 0.062 Uiso 1 1 calc R U . . .
C18 C 0.04336(14) -0.02377(17) 0.74704(10) 0.0270(4) Uani 1 1 d . . . . .
H18 H 0.0460 -0.1058 0.7472 0.032 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 C17 1.377(2) . ?
O1 C20 1.430(2) . ?
C1 C7 1.372(3) . ?
C1 N1 1.406(2) . ?
C1 C14 1.412(3) . ?
N1 C3 1.422(2) . ?
N1 C2 1.429(2) . ?
O2 C23 1.370(2) . ?
O2 C26 1.419(2) . ?
C2 C15 1.383(3) . ?
C2 C19 1.387(3) . ?
N2 C4 1.399(2) . ?
N2 C5 1.413(2) . ?
N2 C6 1.432(2) . ?
O3 C29 1.362(2) . ?
O3 C32 1.417(2) . ?
C3 C21 1.385(3) . ?
C3 C25 1.389(3) . ?
C4 C9 1.378(3) . ?
C4 C10 1.411(3) . ?
O4 C35 1.372(2) . ?
O4 C38 1.416(2) . ?
C7 C8 1.412(3) . ?
C7 H7 0.9500 . ?
C6 C37 1.369(3) . ?
C6 C33 1.382(3) . ?
C5 C27 1.379(3) . ?
C5 C31 1.393(3) . ?
C8 C9 1.416(2) . ?
C8 C12 1.426(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.370(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.422(2) . ?
C11 C13 1.479(2) 3_566 ?
C12 C13 1.424(2) . ?
C13 C14 1.380(2) . ?
C13 C11 1.479(2) 3_566 ?
C14 H14 0.9500 . ?
C19 C18 1.386(3) . ?
C19 H19 0.9500 . ?
C15 C16 1.386(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(3) . ?
C24 C25 1.377(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.381(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.388(3) . ?
C30 C31 1.373(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.377(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.379(3) . ?
C36 C37 1.390(3) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O1 C20 117.30(16) . . ?
C7 C1 N1 121.84(16) . . ?
C7 C1 C14 119.12(17) . . ?
N1 C1 C14 119.02(16) . . ?
C1 N1 C3 120.94(15) . . ?
C1 N1 C2 120.45(15) . . ?
C3 N1 C2 118.39(15) . . ?
C23 O2 C26 117.02(15) . . ?
C15 C2 C19 118.47(18) . . ?
C15 C2 N1 120.41(17) . . ?
C19 C2 N1 121.12(18) . . ?
C4 N2 C5 122.92(15) . . ?
C4 N2 C6 117.95(15) . . ?
C5 N2 C6 118.30(15) . . ?
C29 O3 C32 116.91(15) . . ?
C21 C3 C25 118.54(18) . . ?
C21 C3 N1 119.78(17) . . ?
C25 C3 N1 121.60(16) . . ?
C9 C4 N2 123.43(17) . . ?
C9 C4 C10 118.73(16) . . ?
N2 C4 C10 117.84(16) . . ?
C35 O4 C38 116.30(15) . . ?
C1 C7 C8 120.93(17) . . ?
C1 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C37 C6 C33 119.75(17) . . ?
C37 C6 N2 120.19(18) . . ?
C33 C6 N2 119.97(18) . . ?
C27 C5 C31 118.67(17) . . ?
C27 C5 N2 120.86(17) . . ?
C31 C5 N2 120.45(17) . . ?
C7 C8 C9 120.80(16) . . ?
C7 C8 C12 119.64(16) . . ?
C9 C8 C12 119.56(16) . . ?
C4 C9 C8 120.74(17) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C4 122.72(17) . . ?
C11 C10 H10 118.6 . . ?
C4 C10 H10 118.6 . . ?
C10 C11 C12 119.03(16) . . ?
C10 C11 C13 121.79(16) . 3_566 ?
C12 C11 C13 119.18(15) . 3_566 ?
C11 C12 C13 121.94(16) . . ?
C11 C12 C8 119.06(16) . . ?
C13 C12 C8 118.95(16) . . ?
C14 C13 C12 119.12(16) . . ?
C14 C13 C11 121.92(16) . 3_566 ?
C12 C13 C11 118.85(15) . 3_566 ?
C13 C14 C1 122.11(17) . . ?
C13 C14 H14 118.9 . . ?
C1 C14 H14 118.9 . . ?
C18 C19 C2 121.38(19) . . ?
C18 C19 H19 119.3 . . ?
C2 C19 H19 119.3 . . ?
C2 C15 C16 120.74(18) . . ?
C2 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C17 119.83(19) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
O1 C17 C18 125.08(18) . . ?
O1 C17 C16 114.83(18) . . ?
C18 C17 C16 120.09(18) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C21 C22 121.05(18) . . ?
C3 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 119.75(17) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
O2 C23 C22 124.49(17) . . ?
O2 C23 C24 115.86(17) . . ?
C22 C23 C24 119.64(18) . . ?
C25 C24 C23 120.37(18) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C3 120.58(17) . . ?
C24 C25 H25 119.7 . . ?
C3 C25 H25 119.7 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C5 C27 C28 121.16(17) . . ?
C5 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C27 C28 C29 119.72(17) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
O3 C29 C28 124.46(17) . . ?
O3 C29 C30 116.07(16) . . ?
C28 C29 C30 119.47(17) . . ?
C31 C30 C29 120.30(18) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C5 120.58(18) . . ?
C30 C31 H31 119.7 . . ?
C5 C31 H31 119.7 . . ?
O3 C32 H32A 109.5 . . ?
O3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C6 119.83(19) . . ?
C34 C33 H33 120.1 . . ?
C6 C33 H33 120.1 . . ?
C33 C34 C35 120.16(19) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
O4 C35 C36 124.16(17) . . ?
O4 C35 C34 115.53(17) . . ?
C36 C35 C34 120.32(17) . . ?
C35 C36 C37 118.78(18) . . ?
C35 C36 H36 120.6 . . ?
C37 C36 H36 120.6 . . ?
C6 C37 C36 121.00(19) . . ?
C6 C37 H37 119.5 . . ?
C36 C37 H37 119.5 . . ?
O4 C38 H38A 109.5 . . ?
O4 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O4 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C17 C18 C19 119.37(18) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?

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
C7 C1 N1 C3 -30.7(3) . . . . ?
C14 C1 N1 C3 147.58(17) . . . . ?
C7 C1 N1 C2 154.75(18) . . . . ?
C14 C1 N1 C2 -27.0(2) . . . . ?
C1 N1 C2 C15 -46.1(2) . . . . ?
C3 N1 C2 C15 139.16(18) . . . . ?
C1 N1 C2 C19 133.89(19) . . . . ?
C3 N1 C2 C19 -40.8(2) . . . . ?
C1 N1 C3 C21 139.90(18) . . . . ?
C2 N1 C3 C21 -45.4(2) . . . . ?
C1 N1 C3 C25 -43.4(3) . . . . ?
C2 N1 C3 C25 131.32(19) . . . . ?
C5 N2 C4 C9 17.2(3) . . . . ?
C6 N2 C4 C9 -152.22(18) . . . . ?
C5 N2 C4 C10 -162.53(17) . . . . ?
C6 N2 C4 C10 28.1(3) . . . . ?
N1 C1 C7 C8 175.38(16) . . . . ?
C14 C1 C7 C8 -2.9(3) . . . . ?
C4 N2 C6 C37 59.4(2) . . . . ?
C5 N2 C6 C37 -110.4(2) . . . . ?
C4 N2 C6 C33 -117.0(2) . . . . ?
C5 N2 C6 C33 73.1(2) . . . . ?
C4 N2 C5 C27 50.8(3) . . . . ?
C6 N2 C5 C27 -139.79(19) . . . . ?
C4 N2 C5 C31 -131.0(2) . . . . ?
C6 N2 C5 C31 38.3(3) . . . . ?
C1 C7 C8 C9 -177.46(17) . . . . ?
C1 C7 C8 C12 2.4(3) . . . . ?
N2 C4 C9 C8 -179.66(17) . . . . ?
C10 C4 C9 C8 0.0(3) . . . . ?
C7 C8 C9 C4 176.59(17) . . . . ?
C12 C8 C9 C4 -3.2(3) . . . . ?
C9 C4 C10 C11 3.4(3) . . . . ?
N2 C4 C10 C11 -176.85(17) . . . . ?
C4 C10 C11 C12 -3.5(3) . . . . ?
C4 C10 C11 C13 177.13(17) . . . 3_566 ?
C10 C11 C12 C13 -177.23(16) . . . . ?
C13 C11 C12 C13 2.2(3) 3_566 . . . ?
C10 C11 C12 C8 0.2(2) . . . . ?
C13 C11 C12 C8 179.55(15) 3_566 . . . ?
C7 C8 C12 C11 -176.70(16) . . . . ?
C9 C8 C12 C11 3.1(2) . . . . ?
C7 C8 C12 C13 0.8(2) . . . . ?
C9 C8 C12 C13 -179.41(16) . . . . ?
C11 C12 C13 C14 174.12(16) . . . . ?
C8 C12 C13 C14 -3.3(2) . . . . ?
C11 C12 C13 C11 -2.2(3) . . . 3_566 ?
C8 C12 C13 C11 -179.55(15) . . . 3_566 ?
C12 C13 C14 C1 2.8(3) . . . . ?
C11 C13 C14 C1 178.98(16) 3_566 . . . ?
C7 C1 C14 C13 0.3(3) . . . . ?
N1 C1 C14 C13 -178.04(16) . . . . ?
C15 C2 C19 C18 1.0(3) . . . . ?
N1 C2 C19 C18 -179.05(16) . . . . ?
C19 C2 C15 C16 -3.4(3) . . . . ?
N1 C2 C15 C16 176.62(17) . . . . ?
C2 C15 C16 C17 2.8(3) . . . . ?
C20 O1 C17 C18 -0.3(3) . . . . ?
C20 O1 C17 C16 179.47(17) . . . . ?
C15 C16 C17 O1 -179.44(16) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C25 C3 C21 C22 -0.8(3) . . . . ?
N1 C3 C21 C22 176.05(17) . . . . ?
C3 C21 C22 C23 2.8(3) . . . . ?
C26 O2 C23 C22 -4.2(3) . . . . ?
C26 O2 C23 C24 176.34(18) . . . . ?
C21 C22 C23 O2 178.10(17) . . . . ?
C21 C22 C23 C24 -2.4(3) . . . . ?
O2 C23 C24 C25 179.56(16) . . . . ?
C22 C23 C24 C25 0.1(3) . . . . ?
C23 C24 C25 C3 2.0(3) . . . . ?
C21 C3 C25 C24 -1.6(3) . . . . ?
N1 C3 C25 C24 -178.40(17) . . . . ?
C31 C5 C27 C28 2.8(3) . . . . ?
N2 C5 C27 C28 -179.05(17) . . . . ?
C5 C27 C28 C29 -0.8(3) . . . . ?
C32 O3 C29 C28 -4.5(3) . . . . ?
C32 O3 C29 C30 174.71(17) . . . . ?
C27 C28 C29 O3 177.09(17) . . . . ?
C27 C28 C29 C30 -2.1(3) . . . . ?
O3 C29 C30 C31 -176.26(17) . . . . ?
C28 C29 C30 C31 3.0(3) . . . . ?
C29 C30 C31 C5 -1.0(3) . . . . ?
C27 C5 C31 C30 -1.9(3) . . . . ?
N2 C5 C31 C30 179.95(17) . . . . ?
C37 C6 C33 C34 -3.3(3) . . . . ?
N2 C6 C33 C34 173.22(17) . . . . ?
C6 C33 C34 C35 -0.2(3) . . . . ?
C38 O4 C35 C36 -12.3(3) . . . . ?
C38 O4 C35 C34 168.01(18) . . . . ?
C33 C34 C35 O4 -177.18(18) . . . . ?
C33 C34 C35 C36 3.1(3) . . . . ?
O4 C35 C36 C37 177.68(17) . . . . ?
C34 C35 C36 C37 -2.7(3) . . . . ?
C33 C6 C37 C36 3.7(3) . . . . ?
N2 C6 C37 C36 -172.73(17) . . . . ?
C35 C36 C37 C6 -0.8(3) . . . . ?
O1 C17 C18 C19 177.03(17) . . . . ?
C16 C17 C18 C19 -2.8(3) . . . . ?
C2 C19 C18 C17 2.1(3) . . . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.045


_chemical_name_systematic        
N2,N2,N5,N5,N8,N8,N11,N11-(4-methoxyphenyl)perylene-2,5,8,11-tetraamine
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
