# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_PYPN
_database_code_depnum_ccdc_archive 'CCDC 1041210'
_audit_update_record             
;
2014-12-26 deposited with the CCDC.
2015-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2-(pyren-1-yl)-1H-phenanthro[9,10-d]imidazole
_chemical_name_common            PYPN
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H18 N2'
_chemical_formula_weight         418.47

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'

_symmetry_cell_setting           Rhombohedral
_symmetry_space_group_name_H-M   R-3

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   24.4661(10)
_cell_length_b                   24.4661(10)
_cell_length_c                   20.545(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     10650.6(14)
_cell_formula_units_Z            18
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1751
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      24.08

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3924
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9857
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17254
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.1047
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4637
_reflns_number_gt                2130
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker AEPX2'
_computing_cell_refinement       'Bruker AEPX2'
_computing_data_reduction        'Bruker AEPX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          SQUEEZE

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0915P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         4637
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1547
_refine_ls_R_factor_gt           0.0735
_refine_ls_wR_factor_ref         0.2145
_refine_ls_wR_factor_gt          0.1903
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.15977(12) 0.19725(11) -0.03824(11) 0.0548(7) Uani 1 1 d . . .
H1A H 0.1307 0.2083 -0.0358 0.066 Uiso 1 1 calc R . .
N2 N 0.22469(12) 0.16228(12) -0.00865(12) 0.0543(7) Uani 1 1 d . . .
C1 C 0.15100(15) 0.16153(15) 0.07620(15) 0.0504(8) Uani 1 1 d . . .
C2 C 0.18843(15) 0.19275(15) 0.13083(15) 0.0518(8) Uani 1 1 d . . .
C3 C 0.16009(15) 0.17965(15) 0.19292(15) 0.0514(8) Uani 1 1 d . . .
C4 C 0.09465(16) 0.13537(16) 0.20026(16) 0.0585(9) Uani 1 1 d . . .
C5 C 0.05925(16) 0.10600(15) 0.14480(17) 0.0614(9) Uani 1 1 d . . .
H5A H 0.0155 0.0765 0.1488 0.074 Uiso 1 1 calc R . .
C6 C 0.08691(17) 0.11923(15) 0.08443(16) 0.0585(9) Uani 1 1 d . . .
H6A H 0.0617 0.0990 0.0473 0.070 Uiso 1 1 calc R . .
C7 C 0.25466(15) 0.23931(15) 0.12555(16) 0.0552(9) Uani 1 1 d . . .
H7A H 0.2747 0.2492 0.0842 0.066 Uiso 1 1 calc R . .
C8 C 0.28791(16) 0.26853(16) 0.17907(16) 0.0615(9) Uani 1 1 d . . .
H8A H 0.3312 0.2993 0.1741 0.074 Uiso 1 1 calc R . .
C9 C 0.26199(16) 0.25608(16) 0.24242(16) 0.0571(9) Uani 1 1 d . . .
C10 C 0.19708(16) 0.21059(15) 0.24942(15) 0.0555(9) Uani 1 1 d . . .
C11 C 0.16864(19) 0.19643(17) 0.31194(16) 0.0651(10) Uani 1 1 d . . .
C12 C 0.1033(2) 0.15237(19) 0.31738(18) 0.0768(11) Uani 1 1 d . . .
H12A H 0.0840 0.1434 0.3591 0.092 Uiso 1 1 calc R . .
C13 C 0.06763(18) 0.12283(17) 0.26450(19) 0.0747(11) Uani 1 1 d . . .
H13A H 0.0240 0.0933 0.2699 0.090 Uiso 1 1 calc R . .
C14 C 0.29655(18) 0.28595(17) 0.29807(18) 0.0705(10) Uani 1 1 d . . .
H14A H 0.3401 0.3164 0.2940 0.085 Uiso 1 1 calc R . .
C15 C 0.2693(2) 0.2725(2) 0.35881(19) 0.0811(12) Uani 1 1 d . . .
H15A H 0.2940 0.2935 0.3960 0.097 Uiso 1 1 calc R . .
C16 C 0.2059(2) 0.2286(2) 0.36585(18) 0.0775(11) Uani 1 1 d . . .
H16A H 0.1874 0.2200 0.4080 0.093 Uiso 1 1 calc R . .
C17 C 0.17921(15) 0.17358(15) 0.01125(15) 0.0530(8) Uani 1 1 d . . .
C18 C 0.19432(14) 0.20059(13) -0.09288(14) 0.0482(8) Uani 1 1 d . . .
C19 C 0.19108(14) 0.22002(14) -0.15773(14) 0.0508(8) Uani 1 1 d . . .
C20 C 0.23054(14) 0.21338(14) -0.20373(15) 0.0507(8) Uani 1 1 d . . .
C21 C 0.27266(14) 0.18979(14) -0.18447(15) 0.0517(8) Uani 1 1 d . . .
C22 C 0.27552(14) 0.17381(13) -0.11890(15) 0.0495(8) Uani 1 1 d . . .
C23 C 0.23408(14) 0.17988(14) -0.07351(14) 0.0492(8) Uani 1 1 d . . .
C24 C 0.15399(15) 0.24626(15) -0.17574(16) 0.0596(9) Uani 1 1 d . . .
H24A H 0.1278 0.2505 -0.1445 0.072 Uiso 1 1 calc R . .
C25 C 0.15551(17) 0.26587(17) -0.23868(18) 0.0730(11) Uani 1 1 d . . .
H25A H 0.1312 0.2848 -0.2505 0.088 Uiso 1 1 calc R . .
C26 C 0.19199(17) 0.25819(17) -0.28465(17) 0.0687(10) Uani 1 1 d . . .
H26A H 0.1915 0.2706 -0.3284 0.082 Uiso 1 1 calc R . .
C27 C 0.22872(16) 0.23308(15) -0.26828(15) 0.0623(9) Uani 1 1 d . . .
H27A H 0.2538 0.2286 -0.3009 0.075 Uiso 1 1 calc R . .
C28 C 0.31076(16) 0.18092(15) -0.22993(16) 0.0600(9) Uani 1 1 d . . .
H28A H 0.3087 0.1896 -0.2747 0.072 Uiso 1 1 calc R . .
C29 C 0.35064(17) 0.16005(16) -0.21052(18) 0.0697(10) Uani 1 1 d . . .
H29A H 0.3761 0.1549 -0.2420 0.084 Uiso 1 1 calc R . .
C30 C 0.35477(17) 0.14615(15) -0.14531(17) 0.0666(10) Uani 1 1 d . . .
H30A H 0.3834 0.1326 -0.1324 0.080 Uiso 1 1 calc R . .
C31 C 0.31672(15) 0.15240(15) -0.10005(16) 0.0568(9) Uani 1 1 d . . .
H31A H 0.3184 0.1421 -0.0558 0.068 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C17 1.368(4) . ?
N1 C18 1.383(3) . ?
N1 H1A 0.8800 . ?
N2 C17 1.337(4) . ?
N2 C23 1.384(4) . ?
C1 C6 1.391(4) . ?
C1 C2 1.408(4) . ?
C1 C17 1.463(4) . ?
C2 C3 1.410(4) . ?
C2 C7 1.446(4) . ?
C3 C4 1.423(4) . ?
C3 C10 1.433(4) . ?
C4 C5 1.394(4) . ?
C4 C13 1.439(4) . ?
C5 C6 1.372(4) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C8 1.342(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.413(4) . ?
C8 H8A 0.9500 . ?
C9 C14 1.392(4) . ?
C9 C10 1.419(4) . ?
C10 C11 1.419(4) . ?
C11 C16 1.400(5) . ?
C11 C12 1.418(5) . ?
C12 C13 1.354(5) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C14 C15 1.375(5) . ?
C14 H14A 0.9500 . ?
C15 C16 1.383(5) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C18 C23 1.362(4) . ?
C18 C19 1.430(4) . ?
C19 C24 1.398(4) . ?
C19 C20 1.417(4) . ?
C20 C27 1.419(4) . ?
C20 C21 1.465(4) . ?
C21 C28 1.411(4) . ?
C21 C22 1.414(4) . ?
C22 C31 1.403(4) . ?
C22 C23 1.439(4) . ?
C24 C25 1.373(4) . ?
C24 H24A 0.9500 . ?
C25 C26 1.375(5) . ?
C25 H25A 0.9500 . ?
C26 C27 1.360(4) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
C28 C29 1.367(4) . ?
C28 H28A 0.9500 . ?
C29 C30 1.398(4) . ?
C29 H29A 0.9500 . ?
C30 C31 1.377(4) . ?
C30 H30A 0.9500 . ?
C31 H31A 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 N1 C18 107.3(3) . . ?
C17 N1 H1A 126.4 . . ?
C18 N1 H1A 126.4 . . ?
C17 N2 C23 104.8(2) . . ?
C6 C1 C2 119.5(3) . . ?
C6 C1 C17 120.2(3) . . ?
C2 C1 C17 120.3(3) . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 C7 122.4(3) . . ?
C3 C2 C7 118.5(3) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 C10 120.3(3) . . ?
C4 C3 C10 119.3(3) . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 C13 122.6(3) . . ?
C3 C4 C13 118.8(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C5 C6 C1 121.7(3) . . ?
C5 C6 H6A 119.2 . . ?
C1 C6 H6A 119.2 . . ?
C8 C7 C2 120.0(3) . . ?
C8 C7 H7A 120.0 . . ?
C2 C7 H7A 120.0 . . ?
C7 C8 C9 123.6(3) . . ?
C7 C8 H8A 118.2 . . ?
C9 C8 H8A 118.2 . . ?
C14 C9 C8 123.6(4) . . ?
C14 C9 C10 118.4(3) . . ?
C8 C9 C10 117.9(3) . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 C3 120.1(3) . . ?
C9 C10 C3 119.7(3) . . ?
C16 C11 C12 122.4(4) . . ?
C16 C11 C10 118.5(4) . . ?
C12 C11 C10 119.1(3) . . ?
C13 C12 C11 121.6(4) . . ?
C13 C12 H12A 119.2 . . ?
C11 C12 H12A 119.2 . . ?
C12 C13 C4 121.2(4) . . ?
C12 C13 H13A 119.4 . . ?
C4 C13 H13A 119.4 . . ?
C15 C14 C9 121.7(4) . . ?
C15 C14 H14A 119.2 . . ?
C9 C14 H14A 119.2 . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C11 121.1(4) . . ?
C15 C16 H16A 119.5 . . ?
C11 C16 H16A 119.5 . . ?
N2 C17 N1 111.2(3) . . ?
N2 C17 C1 126.5(3) . . ?
N1 C17 C1 122.3(3) . . ?
C23 C18 N1 105.7(3) . . ?
C23 C18 C19 124.4(3) . . ?
N1 C18 C19 130.0(3) . . ?
C24 C19 C20 120.8(3) . . ?
C24 C19 C18 123.7(3) . . ?
C20 C19 C18 115.4(3) . . ?
C19 C20 C27 116.5(3) . . ?
C19 C20 C21 121.2(3) . . ?
C27 C20 C21 122.3(3) . . ?
C28 C21 C22 117.4(3) . . ?
C28 C21 C20 122.1(3) . . ?
C22 C21 C20 120.5(3) . . ?
C31 C22 C21 120.7(3) . . ?
C31 C22 C23 122.3(3) . . ?
C21 C22 C23 117.0(3) . . ?
C18 C23 N2 111.0(3) . . ?
C18 C23 C22 121.3(3) . . ?
N2 C23 C22 127.4(3) . . ?
C25 C24 C19 119.9(3) . . ?
C25 C24 H24A 120.0 . . ?
C19 C24 H24A 120.0 . . ?
C24 C25 C26 120.3(3) . . ?
C24 C25 H25A 119.8 . . ?
C26 C25 H25A 119.8 . . ?
C27 C26 C25 120.8(3) . . ?
C27 C26 H26A 119.6 . . ?
C25 C26 H26A 119.6 . . ?
C26 C27 C20 121.6(3) . . ?
C26 C27 H27A 119.2 . . ?
C20 C27 H27A 119.2 . . ?
C29 C28 C21 120.9(3) . . ?
C29 C28 H28A 119.5 . . ?
C21 C28 H28A 119.5 . . ?
C28 C29 C30 121.5(3) . . ?
C28 C29 H29A 119.3 . . ?
C30 C29 H29A 119.3 . . ?
C31 C30 C29 119.0(3) . . ?
C31 C30 H30A 120.5 . . ?
C29 C30 H30A 120.5 . . ?
C30 C31 C22 120.4(3) . . ?
C30 C31 H31A 119.8 . . ?
C22 C31 H31A 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.051

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.333 0.667 0.167 617 232 ' '
2 0.667 0.333 -0.167 617 232 ' '
3 0.000 0.000 0.500 619 232 ' '
_platon_squeeze_details          
;
;


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ether/THF'
