# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_zoulin
_database_code_depnum_ccdc_archive 'CCDC 1046692'
_audit_update_record             
;
2015-02-02 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;
_audit_creation_date             2013-01-07
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            PyrDI
_chemical_name_systematic        'pyrene-1,2:6,7-tetracarboxylic diimides'
_chemical_formula_moiety         'C26 H20 N2 O4'
_chemical_formula_sum            'C26 H20 N2 O4'
_chemical_formula_weight         424.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C24H18O4N2
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.3610(5)
_cell_length_b                   8.3907(5)
_cell_length_c                   16.3626(10)
_cell_angle_alpha                80.826(5)
_cell_angle_beta                 89.447(5)
_cell_angle_gamma                85.419(5)
_cell_volume                     994.50(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2338
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      29.7400
_cell_measurement_theta_min      3.7560
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6115
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.65
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9886
_diffrn_measured_fraction_theta_max 0.8383
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00   56.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8167  -99.0000  150.0000 76

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   84.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8167   57.0000   30.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega  -55.00   40.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8167  -57.0000 -120.0000 95
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0278394000
_diffrn_orient_matrix_UB_12      0.0808467000
_diffrn_orient_matrix_UB_13      0.0048480000
_diffrn_orient_matrix_UB_21      -0.0861694000
_diffrn_orient_matrix_UB_22      -0.0074604000
_diffrn_orient_matrix_UB_23      -0.0174291000
_diffrn_orient_matrix_UB_31      -0.0338315000
_diffrn_orient_matrix_UB_32      -0.0280521000
_diffrn_orient_matrix_UB_33      0.0400111000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3041
_reflns_number_total             3899
_reflns_odcompleteness_completeness 98.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0571P)²+0.6631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1363
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H6 of C6, H9 of C9, H22 of C22, H16 of C16, H25 of C25, H26 of C26, H12 of
  C12, H13 of C13
 At 1.5 times of:
  {H11a,H11b,H11c} of C11, {H10a,H10b,H10c} of C10, {H23a,H23b,H23c} of C23,
  {H24a,H24b,H24c} of C24
2.a Ternary CH refined with riding coordinates:
 C9(H9), C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C13(H13), C16(H16), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C23(H23a,H23b,H23c), C24(H24a,H24b,
 H24c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2166(3) 0.1203(2) 0.20386(12) 0.0244(4) Uani 1 1 d . . .
C2 C 0.1646(2) 0.2786(2) 0.15095(12) 0.0207(4) Uani 1 1 d . . .
C3 C 0.0953(2) 0.3127(2) 0.07052(11) 0.0196(4) Uani 1 1 d . . .
C4 C 0.0393(2) 0.4786(2) 0.04030(11) 0.0183(4) Uani 1 1 d . . .
C5 C 0.0586(2) 0.6012(2) 0.09014(11) 0.0198(4) Uani 1 1 d . . .
C6 C 0.1399(2) 0.5606(2) 0.16877(12) 0.0216(4) Uani 1 1 d . . .
H6 H 0.1603 0.6416 0.2014 0.026 Uiso 1 1 calc R . .
C7 C 0.1891(2) 0.3997(2) 0.19702(11) 0.0213(4) Uani 1 1 d . . .
C8 C 0.2683(3) 0.3231(2) 0.27897(12) 0.0252(4) Uani 1 1 d . . .
C9 C 0.3303(3) 0.0317(2) 0.35023(13) 0.0316(5) Uani 1 1 d . . .
H9 H 0.3365 -0.0760 0.3311 0.038 Uiso 1 1 calc R . .
C10 C 0.1827(3) 0.0322(3) 0.41581(15) 0.0441(6) Uani 1 1 d . . .
H10A H 0.1758 0.1355 0.4368 0.066 Uiso 1 1 calc R . .
H10B H 0.2120 -0.0567 0.4615 0.066 Uiso 1 1 calc R . .
H10C H 0.0651 0.0180 0.3914 0.066 Uiso 1 1 calc R . .
C11 C 0.5171(3) 0.0539(3) 0.38282(14) 0.0375(5) Uani 1 1 d . . .
H11A H 0.6055 0.0584 0.3375 0.056 Uiso 1 1 calc R . .
H11B H 0.5539 -0.0373 0.4262 0.056 Uiso 1 1 calc R . .
H11C H 0.5126 0.1551 0.4058 0.056 Uiso 1 1 calc R . .
C12 C 0.0790(2) 0.1939(2) 0.01790(12) 0.0219(4) Uani 1 1 d . . .
H12 H 0.1203 0.0842 0.0370 0.026 Uiso 1 1 calc R . .
C13 C -0.0056(2) 0.7648(2) 0.05861(12) 0.0221(4) Uani 1 1 d . . .
H13 H 0.0037 0.8462 0.0923 0.027 Uiso 1 1 calc R . .
C14 C 0.7662(3) 0.4379(3) 0.28116(13) 0.0341(5) Uani 1 1 d . . .
C15 C 0.6893(3) 0.4297(3) 0.19752(13) 0.0290(5) Uani 1 1 d . . .
C16 C 0.6783(3) 0.2986(3) 0.15725(13) 0.0292(5) Uani 1 1 d . . .
H16 H 0.7203 0.1926 0.1829 0.035 Uiso 1 1 calc R . .
C17 C 0.6033(2) 0.3260(2) 0.07732(12) 0.0248(4) Uani 1 1 d . . .
C18 C 0.5380(2) 0.4868(2) 0.04045(12) 0.0223(4) Uani 1 1 d . . .
C19 C 0.5482(2) 0.6195(2) 0.08421(12) 0.0244(4) Uani 1 1 d . . .
C20 C 0.6277(3) 0.5855(3) 0.16268(13) 0.0276(4) Uani 1 1 d . . .
C21 C 0.6647(3) 0.6978(3) 0.22260(14) 0.0330(5) Uani 1 1 d . . .
C22 C 0.7848(3) 0.6628(3) 0.36790(14) 0.0415(6) Uani 1 1 d . . .
H22 H 0.7507 0.7821 0.3568 0.050 Uiso 1 1 calc R . .
C23 C 0.6621(4) 0.5916(4) 0.43648(15) 0.0515(7) Uani 1 1 d . . .
H23A H 0.5346 0.6148 0.4189 0.077 Uiso 1 1 calc R . .
H23B H 0.6818 0.6397 0.4861 0.077 Uiso 1 1 calc R . .
H23C H 0.6906 0.4741 0.4489 0.077 Uiso 1 1 calc R . .
C24 C 0.9825(4) 0.6411(4) 0.38889(18) 0.0545(7) Uani 1 1 d . . .
H24A H 1.0218 0.5252 0.3997 0.082 Uiso 1 1 calc R . .
H24B H 1.0037 0.6893 0.4383 0.082 Uiso 1 1 calc R . .
H24C H 1.0522 0.6943 0.3425 0.082 Uiso 1 1 calc R . .
C25 C 0.4771(3) 0.7776(2) 0.04702(14) 0.0284(5) Uani 1 1 d . . .
H25 H 0.4799 0.8657 0.0768 0.034 Uiso 1 1 calc R . .
C26 C 0.4057(3) 0.8028(2) -0.03035(13) 0.0273(5) Uani 1 1 d . . .
H26 H 0.3603 0.9091 -0.0540 0.033 Uiso 1 1 calc R . .
N1 N 0.2795(2) 0.15677(19) 0.27841(10) 0.0267(4) Uani 1 1 d . . .
N2 N 0.7452(2) 0.5983(2) 0.29112(11) 0.0354(4) Uani 1 1 d . . .
O1 O 0.2045(2) -0.01534(16) 0.18899(9) 0.0334(4) Uani 1 1 d . . .
O2 O 0.3155(2) 0.38953(17) 0.33478(9) 0.0334(4) Uani 1 1 d . . .
O3 O 0.8361(2) 0.3257(2) 0.32959(10) 0.0441(4) Uani 1 1 d . . .
O4 O 0.6377(2) 0.8430(2) 0.21434(11) 0.0439(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
C1 C2 1.489(3) . ?
C1 N1 1.396(3) . ?
C1 O1 1.212(2) . ?
C2 C3 1.394(3) . ?
C2 C7 1.382(3) . ?
C3 C4 1.430(3) . ?
C3 C12 1.430(3) . ?
C4 C4 1.426(4) 2_565 ?
C4 C5 1.427(3) . ?
C5 C6 1.404(3) . ?
C5 C13 1.431(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.377(3) . ?
C7 C8 1.494(3) . ?
C8 N1 1.393(3) . ?
C8 O2 1.210(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.520(3) . ?
C9 C11 1.515(3) . ?
C9 N1 1.475(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C13 1.351(3) 2_565 ?
C13 C12 1.351(3) 2_565 ?
C13 H13 0.9500 . ?
C14 C15 1.500(3) . ?
C14 N2 1.378(3) . ?
C14 O3 1.213(3) . ?
C15 C16 1.377(3) . ?
C15 C20 1.383(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.402(3) . ?
C17 C18 1.435(3) . ?
C17 C26 1.428(3) 2_665 ?
C18 C18 1.419(4) 2_665 ?
C18 C19 1.423(3) . ?
C19 C20 1.394(3) . ?
C19 C25 1.429(3) . ?
C20 C21 1.505(3) . ?
C21 N2 1.393(3) . ?
C21 O4 1.205(3) . ?
C22 H22 1.0000 . ?
C22 C23 1.511(3) . ?
C22 C24 1.489(4) . ?
C22 N2 1.485(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25 0.9500 . ?
C25 C26 1.354(3) . ?
C26 C17 1.428(3) 2_665 ?
C26 H26 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
N1 C1 C2 106.19(16) . . ?
O1 C1 C2 128.96(18) . . ?
O1 C1 N1 124.83(18) . . ?
C3 C2 C1 130.28(17) . . ?
C7 C2 C1 107.86(16) . . ?
C7 C2 C3 121.81(17) . . ?
C2 C3 C4 116.40(17) . . ?
C2 C3 C12 124.28(17) . . ?
C4 C3 C12 119.32(17) . . ?
C4 C4 C3 119.4(2) 2_565 . ?
C4 C4 C5 119.7(2) 2_565 . ?
C5 C4 C3 120.91(16) . . ?
C4 C5 C13 119.00(17) . . ?
C6 C5 C4 120.01(16) . . ?
C6 C5 C13 120.99(17) . . ?
C5 C6 H6 121.1 . . ?
C7 C6 C5 117.81(18) . . ?
C7 C6 H6 121.1 . . ?
C2 C7 C8 108.29(16) . . ?
C6 C7 C2 122.88(17) . . ?
C6 C7 C8 128.80(18) . . ?
N1 C8 C7 105.81(16) . . ?
O2 C8 C7 127.97(18) . . ?
O2 C8 N1 126.22(18) . . ?
C10 C9 H9 107.7 . . ?
C11 C9 H9 107.7 . . ?
C11 C9 C10 112.88(19) . . ?
N1 C9 H9 107.7 . . ?
N1 C9 C10 109.69(18) . . ?
N1 C9 C11 110.95(17) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C12 H12 119.5 . . ?
C13 C12 C3 120.97(17) 2_565 . ?
C13 C12 H12 119.5 2_565 . ?
C5 C13 H13 119.2 . . ?
C12 C13 C5 121.54(17) 2_565 . ?
C12 C13 H13 119.2 2_565 . ?
N2 C14 C15 106.36(18) . . ?
O3 C14 C15 126.6(2) . . ?
O3 C14 N2 127.0(2) . . ?
C16 C15 C14 129.9(2) . . ?
C16 C15 C20 122.68(19) . . ?
C20 C15 C14 107.40(19) . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C17 118.14(18) . . ?
C17 C16 H16 120.9 . . ?
C16 C17 C18 119.86(19) . . ?
C16 C17 C26 121.36(18) . 2_665 ?
C26 C17 C18 118.76(18) 2_665 . ?
C18 C18 C17 119.4(2) 2_665 . ?
C18 C18 C19 119.9(2) 2_665 . ?
C19 C18 C17 120.70(18) . . ?
C18 C19 C25 119.53(18) . . ?
C20 C19 C18 116.87(18) . . ?
C20 C19 C25 123.59(19) . . ?
C15 C20 C19 121.71(19) . . ?
C15 C20 C21 108.40(18) . . ?
C19 C20 C21 129.89(19) . . ?
N2 C21 C20 105.13(19) . . ?
O4 C21 C20 129.0(2) . . ?
O4 C21 N2 125.8(2) . . ?
C23 C22 H22 107.0 . . ?
C24 C22 H22 107.0 . . ?
C24 C22 C23 114.4(2) . . ?
N2 C22 H22 107.0 . . ?
N2 C22 C23 109.2(2) . . ?
N2 C22 C24 112.0(2) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C25 H25 119.7 . . ?
C26 C25 C19 120.54(19) . . ?
C26 C25 H25 119.7 . . ?
C17 C26 H26 119.1 2_665 . ?
C25 C26 C17 121.83(18) . 2_665 ?
C25 C26 H26 119.1 . . ?
C1 N1 C9 122.93(16) . . ?
C8 N1 C1 111.74(16) . . ?
C8 N1 C9 124.95(17) . . ?
C14 N2 C21 112.70(18) . . ?
C14 N2 C22 125.73(19) . . ?
C21 N2 C22 121.32(19) . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
