# Electronic Supplementary Material (ESI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1487561'
_audit_update_record             
;
2016-06-24 deposited with the CCDC.
2016-07-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        PBNA
_chemical_name_common            
"(2Z, 2'Z)-3,3'-(1,4-phenylene)bis(2-(naphthalen-2-yl) acrylonitrile"
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H20 N2'
_chemical_formula_sum            'C32 H20 N2'
_chemical_formula_weight         432.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   46.530(9)
_cell_length_b                   6.7629(14)
_cell_length_c                   7.2639(15)
_cell_angle_alpha                90
_cell_angle_beta                 97.22(3)
_cell_angle_gamma                90
_cell_volume                     2267.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6971
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.63

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10567
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -60
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.044
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2589
_reflns_number_gt                1534
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0844P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2589
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1430
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_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
C1 C 0.13866(3) 0.2749(3) 0.2261(2) 0.0370(4) Uani 1 1 d . . . . .
C2 C 0.11599(4) 0.4013(3) 0.2404(2) 0.0409(4) Uani 1 1 d . . . . .
C3 C 0.08682(4) 0.3449(3) 0.1794(2) 0.0423(4) Uani 1 1 d . . . . .
C4 C 0.06335(4) 0.4727(4) 0.1965(3) 0.0555(6) Uani 1 1 d . . . . .
C5 C 0.03550(5) 0.4129(5) 0.1379(3) 0.0683(7) Uani 1 1 d . . . . .
C6 C 0.02997(5) 0.2249(4) 0.0586(3) 0.0696(7) Uani 1 1 d . . . . .
C7 C 0.05234(4) 0.0983(4) 0.0387(3) 0.0601(6) Uani 1 1 d . . . . .
C8 C 0.08145(4) 0.1544(3) 0.1003(2) 0.0444(5) Uani 1 1 d . . . . .
C9 C 0.10516(4) 0.0283(3) 0.0831(3) 0.0491(5) Uani 1 1 d . . . . .
C10 C 0.13285(4) 0.0855(3) 0.1438(3) 0.0456(5) Uani 1 1 d . . . . .
C11 C 0.17437(4) 0.5406(3) 0.3154(3) 0.0435(4) Uani 1 1 d . . . . .
C12 C 0.16894(4) 0.3325(3) 0.2973(2) 0.0365(4) Uani 1 1 d . . . . .
C13 C 0.19015(4) 0.2003(3) 0.3500(3) 0.0422(5) Uani 1 1 d . . . . .
C14 C 0.23660(4) 0.4021(3) 0.3938(3) 0.0475(5) Uani 1 1 d . . . . .
C15 C 0.22057(3) 0.2331(3) 0.4237(2) 0.0377(4) Uani 1 1 d . . . . .
C16 C 0.23471(4) 0.0814(3) 0.5296(3) 0.0475(5) Uani 1 1 d . . . . .
H1 H 0.1014(4) -0.109(3) 0.027(3) 0.060(6) Uiso 1 1 d . . . . .
H2 H 0.0495(4) -0.039(4) -0.016(3) 0.056(6) Uiso 1 1 d . . . . .
H3 H 0.1492(5) -0.004(4) 0.130(3) 0.070(7) Uiso 1 1 d . . . . .
H4 H 0.1857(4) 0.061(4) 0.338(3) 0.061(6) Uiso 1 1 d . . . . .
H5 H 0.1192(4) 0.531(3) 0.292(3) 0.044(5) Uiso 1 1 d . . . . .
H6 H 0.2273(5) 0.508(4) 0.323(3) 0.069(7) Uiso 1 1 d . . . . .
H7 H 0.0679(5) 0.611(4) 0.248(3) 0.066(6) Uiso 1 1 d . . . . .
H8 H 0.0197(6) 0.510(4) 0.147(3) 0.081(7) Uiso 1 1 d . . . . .
H9 H 0.2247(5) -0.040(4) 0.552(3) 0.066(6) Uiso 1 1 d . . . . .
H10 H 0.0092(5) 0.185(4) 0.018(3) 0.082(7) Uiso 1 1 d . . . . .
N2 N 0.17789(4) 0.7068(3) 0.3301(3) 0.0724(6) 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 1.372(2) . ?
C1 C10 1.425(3) . ?
C1 C12 1.490(2) . ?
C2 C3 1.426(2) . ?
C3 C4 1.410(3) . ?
C3 C8 1.420(3) . ?
C4 C5 1.373(3) . ?
C5 C6 1.406(4) . ?
C6 C7 1.369(3) . ?
C7 C8 1.423(2) . ?
C8 C9 1.412(3) . ?
C9 C10 1.364(2) . ?
C11 N2 1.139(2) . ?
C11 C12 1.433(3) . ?
C12 C13 1.351(2) . ?
C13 C15 1.466(2) . ?
C14 C16 1.385(2) 7_556 ?
C14 C15 1.396(2) . ?
C15 C16 1.397(2) . ?
C16 C14 1.385(2) 7_556 ?

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 C1 C10 119.00(16) . . ?
C2 C1 C12 120.87(16) . . ?
C10 C1 C12 120.12(15) . . ?
C1 C2 C3 121.40(18) . . ?
C4 C3 C8 119.53(18) . . ?
C4 C3 C2 121.76(19) . . ?
C8 C3 C2 118.71(17) . . ?
C5 C4 C3 120.2(2) . . ?
C4 C5 C6 120.7(2) . . ?
C7 C6 C5 120.4(2) . . ?
C6 C7 C8 120.4(2) . . ?
C9 C8 C3 118.93(16) . . ?
C9 C8 C7 122.3(2) . . ?
C3 C8 C7 118.74(19) . . ?
C10 C9 C8 121.13(19) . . ?
C9 C10 C1 120.80(18) . . ?
N2 C11 C12 178.1(2) . . ?
C13 C12 C11 120.64(16) . . ?
C13 C12 C1 123.39(17) . . ?
C11 C12 C1 115.92(15) . . ?
C12 C13 C15 129.86(18) . . ?
C16 C14 C15 120.72(16) 7_556 . ?
C14 C15 C16 117.58(15) . . ?
C14 C15 C13 125.26(16) . . ?
C16 C15 C13 117.15(16) . . ?
C14 C16 C15 121.69(17) 7_556 . ?

_refine_diff_density_max         0.183
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.060



_exptl_crystal_recrystallization_method Sublimation
_chemical_properties_physical    ', Heat-sensitive,Pressure-sensitive'
_exptl_crystal_preparation       ', Luminescent'
