# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_DPAAnCN
_database_code_depnum_ccdc_archive 'CCDC 1960941'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-10-23 deposited with the CCDC.	2020-01-28 downloaded from the CCDC.
;
_audit_creation_date             2018-03-20
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H18 N2'
_chemical_formula_moiety         'C27 H18 N2'
_chemical_formula_weight         370.45
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/n
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.4404(17)
_cell_length_b                   13.660(2)
_cell_length_c                   13.573(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.071(4)
_cell_angle_gamma                90.0000
_cell_volume                     1924.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3688
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      25.30
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776.00
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_T_max  0.994

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            23037
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3514
_reflns_number_gt                2729
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.1005
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3514
_refine_ls_number_parameters     262
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0555P)²+0.3481P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
N1 N 0.38064(10) 0.17952(8) 0.69866(8) 0.0312(3) Uani 1 1 d . . . . .
N27 N -0.20180(15) 0.11961(11) 0.43210(14) 0.0755(6) Uani 1 1 d . . . . .
C1 C 0.25817(12) 0.15752(9) 0.64650(10) 0.0284(3) Uani 1 1 d . . . . .
C2 C 0.14636(12) 0.17101(9) 0.69329(10) 0.0305(3) Uani 1 1 d . . . . .
C3 C 0.14978(14) 0.20108(10) 0.79383(11) 0.0382(4) Uani 1 1 d . . . . .
H3 H 0.230450 0.211424 0.831740 0.046 Uiso 1 1 calc R U . . .
C4 C 0.03926(16) 0.21519(11) 0.83633(13) 0.0490(4) Uani 1 1 d . . . . .
H4 H 0.042945 0.235209 0.903598 0.059 Uiso 1 1 calc R U . . .
C5 C -0.08168(16) 0.20009(12) 0.78042(16) 0.0560(5) Uani 1 1 d . . . . .
H5 H -0.158600 0.209300 0.810925 0.067 Uiso 1 1 calc R U . . .
C6 C -0.08893(14) 0.17288(11) 0.68476(15) 0.0490(4) Uani 1 1 d . . . . .
H6 H -0.171033 0.163503 0.648651 0.059 Uiso 1 1 calc R U . . .
C7 C 0.02378(13) 0.15794(10) 0.63679(12) 0.0363(4) Uani 1 1 d . . . . .
C8 C 0.01939(14) 0.13267(10) 0.53609(12) 0.0392(4) Uani 1 1 d . . . . .
C9 C 0.13143(14) 0.11507(10) 0.49048(11) 0.0370(3) Uani 1 1 d . . . . .
C10 C 0.13041(19) 0.08382(11) 0.38927(12) 0.0517(5) Uani 1 1 d . . . . .
H10 H 0.050794 0.077460 0.348885 0.062 Uiso 1 1 calc R U . . .
C11 C 0.2422(2) 0.06334(12) 0.35097(13) 0.0576(5) Uani 1 1 d . . . . .
H11 H 0.239743 0.042072 0.284161 0.069 Uiso 1 1 calc R U . . .
C12 C 0.36077(19) 0.07297(12) 0.40798(13) 0.0530(4) Uani 1 1 d . . . . .
H12 H 0.437800 0.057454 0.379852 0.064 Uiso 1 1 calc R U . . .
C13 C 0.36706(16) 0.10407(11) 0.50258(12) 0.0416(4) Uani 1 1 d . . . . .
H13 H 0.448765 0.111208 0.539905 0.050 Uiso 1 1 calc R U . . .
C14 C 0.25321(13) 0.12648(9) 0.54769(10) 0.0326(3) Uani 1 1 d . . . . .
C15 C 0.44410(12) 0.11332(10) 0.76657(10) 0.0294(3) Uani 1 1 d . . . . .
C16 C 0.41156(13) 0.01449(10) 0.76425(10) 0.0333(3) Uani 1 1 d . . . . .
H16 H 0.345379 -0.009087 0.716756 0.040 Uiso 1 1 calc R U . . .
C17 C 0.47617(14) -0.04931(11) 0.83153(12) 0.0411(4) Uani 1 1 d . . . . .
H17 H 0.453667 -0.116719 0.829764 0.049 Uiso 1 1 calc R U . . .
C18 C 0.57244(14) -0.01671(12) 0.90094(12) 0.0442(4) Uani 1 1 d . . . . .
H18 H 0.616642 -0.061244 0.946334 0.053 Uiso 1 1 calc R U . . .
C19 C 0.60383(14) 0.08104(13) 0.90375(11) 0.0451(4) Uani 1 1 d . . . . .
H19 H 0.670040 0.104071 0.951526 0.054 Uiso 1 1 calc R U . . .
C20 C 0.54021(13) 0.14603(11) 0.83793(11) 0.0388(4) Uani 1 1 d . . . . .
H20 H 0.562082 0.213540 0.841293 0.047 Uiso 1 1 calc R U . . .
C21 C 0.44134(13) 0.26659(10) 0.66919(10) 0.0331(3) Uani 1 1 d . . . . .
C22 C 0.56722(14) 0.26496(12) 0.64576(12) 0.0447(4) Uani 1 1 d . . . . .
H22 H 0.614434 0.205384 0.650101 0.054 Uiso 1 1 calc R U . . .
C23 C 0.62409(16) 0.34927(14) 0.61622(13) 0.0561(5) Uani 1 1 d . . . . .
H23 H 0.710763 0.347767 0.600865 0.067 Uiso 1 1 calc R U . . .
C24 C 0.55664(18) 0.43545(14) 0.60877(13) 0.0587(5) Uani 1 1 d . . . . .
H24 H 0.596311 0.493438 0.588082 0.070 Uiso 1 1 calc R U . . .
C25 C 0.43127(18) 0.43776(12) 0.63134(14) 0.0555(5) Uani 1 1 d . . . . .
H25 H 0.384265 0.497409 0.625938 0.067 Uiso 1 1 calc R U . . .
C26 C 0.37332(15) 0.35333(11) 0.66193(12) 0.0421(4) Uani 1 1 d . . . . .
H26 H 0.286913 0.355193 0.677864 0.051 Uiso 1 1 calc R U . . .
C27 C -0.10375(16) 0.12496(11) 0.47810(14) 0.0517(5) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C15 1.4061(17) . ?
N1 C21 1.4248(17) . ?
N1 C1 1.4266(16) . ?
N27 C27 1.144(2) . ?
C1 C2 1.3988(19) . ?
C1 C14 1.402(2) . ?
C2 C3 1.422(2) . ?
C2 C7 1.4319(19) . ?
C3 C4 1.357(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.345(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.419(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.406(2) . ?
C8 C9 1.401(2) . ?
C8 C27 1.439(2) . ?
C9 C14 1.427(2) . ?
C9 C10 1.438(2) . ?
C10 C11 1.356(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.347(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.427(2) . ?
C13 H13 0.9500 . ?
C15 C16 1.3915(19) . ?
C15 C20 1.3925(19) . ?
C16 C17 1.385(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.374(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C26 1.379(2) . ?
C21 C22 1.385(2) . ?
C22 C23 1.375(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.370(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.376(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.386(2) . ?
C25 H25 0.9500 . ?
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
C15 N1 C21 121.88(11) . . ?
C15 N1 C1 121.69(11) . . ?
C21 N1 C1 116.01(10) . . ?
C2 C1 C14 121.73(12) . . ?
C2 C1 N1 119.61(12) . . ?
C14 C1 N1 118.61(12) . . ?
C1 C2 C3 122.44(12) . . ?
C1 C2 C7 118.81(13) . . ?
C3 C2 C7 118.70(12) . . ?
C4 C3 C2 120.85(14) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.06(16) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.86(15) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 121.21(15) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 122.57(14) . . ?
C8 C7 C2 119.12(13) . . ?
C6 C7 C2 118.30(14) . . ?
C9 C8 C7 121.94(13) . . ?
C9 C8 C27 119.03(15) . . ?
C7 C8 C27 119.03(15) . . ?
C8 C9 C14 118.59(13) . . ?
C8 C9 C10 123.45(14) . . ?
C14 C9 C10 117.95(15) . . ?
C11 C10 C9 120.52(16) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 121.15(16) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 120.62(17) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.18(16) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C1 C14 C9 119.62(13) . . ?
C1 C14 C13 121.81(13) . . ?
C9 C14 C13 118.56(13) . . ?
C16 C15 C20 118.90(12) . . ?
C16 C15 N1 120.80(12) . . ?
C20 C15 N1 120.29(12) . . ?
C17 C16 C15 119.66(13) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 121.13(14) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 119.20(14) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C19 C20 120.68(15) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 120.42(14) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C26 C21 C22 119.43(13) . . ?
C26 C21 N1 119.74(12) . . ?
C22 C21 N1 120.81(13) . . ?
C23 C22 C21 120.21(15) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.45(16) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.81(15) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.21(16) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 119.88(15) . . ?
C21 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
N27 C27 C8 179.46(19) . . ?

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
C15 N1 C1 C2 81.10(16) . . . . ?
C21 N1 C1 C2 -106.21(14) . . . . ?
C15 N1 C1 C14 -101.43(14) . . . . ?
C21 N1 C1 C14 71.26(15) . . . . ?
C14 C1 C2 C3 179.07(12) . . . . ?
N1 C1 C2 C3 -3.54(19) . . . . ?
C14 C1 C2 C7 -3.54(19) . . . . ?
N1 C1 C2 C7 173.85(11) . . . . ?
C1 C2 C3 C4 178.78(13) . . . . ?
C7 C2 C3 C4 1.4(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C5 C6 C7 C8 -177.84(14) . . . . ?
C5 C6 C7 C2 1.0(2) . . . . ?
C1 C2 C7 C8 -0.43(19) . . . . ?
C3 C2 C7 C8 177.06(12) . . . . ?
C1 C2 C7 C6 -179.31(12) . . . . ?
C3 C2 C7 C6 -1.82(19) . . . . ?
C6 C7 C8 C9 -177.91(13) . . . . ?
C2 C7 C8 C9 3.3(2) . . . . ?
C6 C7 C8 C27 2.3(2) . . . . ?
C2 C7 C8 C27 -176.54(12) . . . . ?
C7 C8 C9 C14 -2.1(2) . . . . ?
C27 C8 C9 C14 177.68(12) . . . . ?
C7 C8 C9 C10 176.42(13) . . . . ?
C27 C8 C9 C10 -3.8(2) . . . . ?
C8 C9 C10 C11 -176.71(14) . . . . ?
C14 C9 C10 C11 1.8(2) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C2 C1 C14 C9 4.71(19) . . . . ?
N1 C1 C14 C9 -172.71(11) . . . . ?
C2 C1 C14 C13 -174.17(12) . . . . ?
N1 C1 C14 C13 8.42(19) . . . . ?
C8 C9 C14 C1 -1.84(19) . . . . ?
C10 C9 C14 C1 179.55(12) . . . . ?
C8 C9 C14 C13 177.08(12) . . . . ?
C10 C9 C14 C13 -1.54(19) . . . . ?
C12 C13 C14 C1 179.04(14) . . . . ?
C12 C13 C14 C9 0.1(2) . . . . ?
C21 N1 C15 C16 -152.64(13) . . . . ?
C1 N1 C15 C16 19.62(19) . . . . ?
C21 N1 C15 C20 27.85(19) . . . . ?
C1 N1 C15 C20 -159.89(12) . . . . ?
C20 C15 C16 C17 -0.93(19) . . . . ?
N1 C15 C16 C17 179.56(12) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
C17 C18 C19 C20 -0.1(2) . . . . ?
C18 C19 C20 C15 -0.9(2) . . . . ?
C16 C15 C20 C19 1.4(2) . . . . ?
N1 C15 C20 C19 -179.11(13) . . . . ?
C15 N1 C21 C26 -137.15(14) . . . . ?
C1 N1 C21 C26 50.18(18) . . . . ?
C15 N1 C21 C22 44.16(19) . . . . ?
C1 N1 C21 C22 -128.51(14) . . . . ?
C26 C21 C22 C23 0.5(2) . . . . ?
N1 C21 C22 C23 179.18(14) . . . . ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C22 C21 C26 C25 0.0(2) . . . . ?
N1 C21 C26 C25 -178.69(14) . . . . ?
C24 C25 C26 C21 -0.4(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/diethyl ether'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_CzAnCN
_database_code_depnum_ccdc_archive 'CCDC 1960942'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-10-23 deposited with the CCDC.	2020-01-28 downloaded from the CCDC.
;
_audit_creation_date             2018-03-20
_audit_creation_method           'by CrystalStructure 4.2'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H16 N2'
_chemical_formula_moiety         'C27 H16 N2'
_chemical_formula_weight         368.44
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   14.483(3)
_cell_length_b                   9.4676(17)
_cell_length_c                   14.148(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.793(5)
_cell_angle_gamma                90.0000
_cell_volume                     1836.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2381
_cell_measurement_theta_min      1.50
_cell_measurement_theta_max      25.30
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768.00
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_T_max  0.997

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            21587
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_theta_max         25.368
_diffrn_reflns_theta_min         1.485
_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
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3360
_reflns_number_gt                2040
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0825
_refine_ls_wR_factor_gt          0.0718
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3360
_refine_ls_number_parameters     262
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0405P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
N15 N 0.73740(9) 0.11644(13) 0.46813(9) 0.0302(3) Uani 1 1 d . . . . .
N28 N 1.09626(11) 0.59199(16) 0.67868(11) 0.0429(4) Uani 1 1 d . . . . .
C1 C 0.81382(11) 0.21396(15) 0.51541(11) 0.0274(4) Uani 1 1 d . . . . .
C2 C 0.79368(11) 0.35910(16) 0.50234(11) 0.0277(4) Uani 1 1 d . . . . .
C3 C 0.70003(12) 0.41342(17) 0.44730(12) 0.0333(4) Uani 1 1 d . . . . .
H3 H 0.647519 0.349907 0.419363 0.040 Uiso 1 1 calc R U . . .
C4 C 0.68476(13) 0.55417(18) 0.43421(13) 0.0404(5) Uani 1 1 d . . . . .
H4 H 0.621875 0.588205 0.396848 0.048 Uiso 1 1 calc R U . . .
C5 C 0.76128(13) 0.65076(18) 0.47548(13) 0.0454(5) Uani 1 1 d . . . . .
H5 H 0.749856 0.749173 0.464687 0.055 Uiso 1 1 calc R U . . .
C6 C 0.85063(13) 0.60436(17) 0.53022(13) 0.0389(4) Uani 1 1 d . . . . .
H6 H 0.901218 0.670753 0.558362 0.047 Uiso 1 1 calc R U . . .
C7 C 0.87016(11) 0.45774(16) 0.54637(11) 0.0283(4) Uani 1 1 d . . . . .
C8 C 0.96167(11) 0.40679(16) 0.60352(11) 0.0290(4) Uani 1 1 d . . . . .
C9 C 0.98148(11) 0.26157(16) 0.61891(11) 0.0289(4) Uani 1 1 d . . . . .
C10 C 1.07435(12) 0.21002(18) 0.67774(12) 0.0356(4) Uani 1 1 d . . . . .
H10 H 1.124712 0.274857 0.709976 0.043 Uiso 1 1 calc R U . . .
C11 C 1.09182(13) 0.06935(18) 0.68836(13) 0.0399(4) Uani 1 1 d . . . . .
H11 H 1.154022 0.036421 0.728598 0.048 Uiso 1 1 calc R U . . .
C12 C 1.01831(13) -0.02863(18) 0.64010(12) 0.0383(4) Uani 1 1 d . . . . .
H12 H 1.031873 -0.126950 0.647250 0.046 Uiso 1 1 calc R U . . .
C13 C 0.92873(12) 0.01597(17) 0.58375(12) 0.0338(4) Uani 1 1 d . . . . .
H13 H 0.880311 -0.051628 0.551636 0.041 Uiso 1 1 calc R U . . .
C14 C 0.90580(11) 0.16266(16) 0.57175(11) 0.0287(4) Uani 1 1 d . . . . .
C16 C 0.69100(11) 0.02640(15) 0.51699(12) 0.0295(4) Uani 1 1 d . . . . .
C17 C 0.70906(12) 0.00635(17) 0.61826(13) 0.0368(4) Uani 1 1 d . . . . .
H17 H 0.759133 0.056932 0.666519 0.044 Uiso 1 1 calc R U . . .
C18 C 0.65132(13) -0.09015(18) 0.64620(14) 0.0429(5) Uani 1 1 d . . . . .
H18 H 0.662436 -0.107127 0.715167 0.051 Uiso 1 1 calc R U . . .
C19 C 0.57708(13) -0.16326(18) 0.57562(15) 0.0431(5) Uani 1 1 d . . . . .
H19 H 0.538361 -0.228709 0.597241 0.052 Uiso 1 1 calc R U . . .
C20 C 0.55909(12) -0.14218(17) 0.47544(14) 0.0370(4) Uani 1 1 d . . . . .
H20 H 0.507978 -0.191851 0.427759 0.044 Uiso 1 1 calc R U . . .
C21 C 0.61673(11) -0.04703(15) 0.44465(12) 0.0300(4) Uani 1 1 d . . . . .
C22 C 0.61893(11) -0.00063(15) 0.34825(12) 0.0296(4) Uani 1 1 d . . . . .
C23 C 0.56585(12) -0.03715(17) 0.25061(13) 0.0383(4) Uani 1 1 d . . . . .
H23 H 0.515468 -0.105836 0.237544 0.046 Uiso 1 1 calc R U . . .
C24 C 0.58740(13) 0.02774(18) 0.17318(13) 0.0416(5) Uani 1 1 d . . . . .
H24 H 0.552145 0.002821 0.106208 0.050 Uiso 1 1 calc R U . . .
C25 C 0.66044(12) 0.12954(17) 0.19224(13) 0.0378(4) Uani 1 1 d . . . . .
H25 H 0.673324 0.173903 0.137568 0.045 Uiso 1 1 calc R U . . .
C26 C 0.71464(12) 0.16794(16) 0.28800(12) 0.0323(4) Uani 1 1 d . . . . .
H26 H 0.764369 0.237558 0.300441 0.039 Uiso 1 1 calc R U . . .
C27 C 0.69324(11) 0.10023(16) 0.36547(12) 0.0283(4) Uani 1 1 d . . . . .
C28 C 1.03764(12) 0.50759(18) 0.64666(12) 0.0318(4) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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
N15 C27 1.394(2) . ?
N15 C16 1.398(2) . ?
N15 C1 1.4310(19) . ?
N28 C28 1.147(2) . ?
C1 C14 1.401(2) . ?
C1 C2 1.405(2) . ?
C2 C3 1.425(2) . ?
C2 C7 1.429(2) . ?
C3 C4 1.354(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.410(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.350(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.420(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(2) . ?
C8 C9 1.407(2) . ?
C8 C28 1.436(2) . ?
C9 C10 1.421(2) . ?
C9 C14 1.433(2) . ?
C10 C11 1.355(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.411(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.353(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.425(2) . ?
C13 H13 0.9500 . ?
C16 C17 1.384(2) . ?
C16 C21 1.407(2) . ?
C17 C18 1.380(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.371(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.390(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.443(2) . ?
C22 C23 1.391(2) . ?
C22 C27 1.400(2) . ?
C23 C24 1.377(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.378(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(2) . ?
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
C27 N15 C16 108.40(12) . . ?
C27 N15 C1 125.74(12) . . ?
C16 N15 C1 125.78(12) . . ?
C14 C1 C2 122.23(14) . . ?
C14 C1 N15 119.53(13) . . ?
C2 C1 N15 118.24(13) . . ?
C1 C2 C3 123.08(14) . . ?
C1 C2 C7 118.88(14) . . ?
C3 C2 C7 118.04(14) . . ?
C4 C3 C2 120.99(16) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.65(16) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.45(16) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.99(16) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 122.21(14) . . ?
C8 C7 C2 118.95(13) . . ?
C6 C7 C2 118.83(14) . . ?
C7 C8 C9 122.35(14) . . ?
C7 C8 C28 118.08(14) . . ?
C9 C8 C28 119.57(14) . . ?
C8 C9 C10 122.26(15) . . ?
C8 C9 C14 118.64(14) . . ?
C10 C9 C14 119.09(14) . . ?
C11 C10 C9 120.68(16) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.51(16) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.71(15) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.11(15) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C1 C14 C13 123.24(14) . . ?
C1 C14 C9 118.89(13) . . ?
C13 C14 C9 117.87(14) . . ?
C17 C16 N15 129.40(14) . . ?
C17 C16 C21 122.04(15) . . ?
N15 C16 C21 108.56(13) . . ?
C18 C17 C16 117.24(16) . . ?
C18 C17 H17 121.4 . . ?
C16 C17 H17 121.4 . . ?
C17 C18 C19 121.51(17) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C18 120.97(16) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 119.02(16) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C20 C21 C16 119.20(15) . . ?
C20 C21 C22 133.78(15) . . ?
C16 C21 C22 107.02(14) . . ?
C23 C22 C27 119.36(15) . . ?
C23 C22 C21 133.60(15) . . ?
C27 C22 C21 107.03(13) . . ?
C24 C23 C22 119.00(16) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C25 120.53(16) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 122.00(16) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
C25 C26 C27 116.94(15) . . ?
C25 C26 H26 121.5 . . ?
C27 C26 H26 121.5 . . ?
C26 C27 N15 128.87(14) . . ?
C26 C27 C22 122.15(14) . . ?
N15 C27 C22 108.98(13) . . ?
N28 C28 C8 177.37(17) . . ?

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
C27 N15 C1 C14 -115.13(16) . . . . ?
C16 N15 C1 C14 68.3(2) . . . . ?
C27 N15 C1 C2 64.1(2) . . . . ?
C16 N15 C1 C2 -112.40(16) . . . . ?
C14 C1 C2 C3 -178.48(15) . . . . ?
N15 C1 C2 C3 2.3(2) . . . . ?
C14 C1 C2 C7 1.3(2) . . . . ?
N15 C1 C2 C7 -177.97(13) . . . . ?
C1 C2 C3 C4 -178.05(16) . . . . ?
C7 C2 C3 C4 2.2(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 -179.35(16) . . . . ?
C5 C6 C7 C2 0.9(2) . . . . ?
C1 C2 C7 C8 -1.9(2) . . . . ?
C3 C2 C7 C8 177.83(15) . . . . ?
C1 C2 C7 C6 177.84(15) . . . . ?
C3 C2 C7 C6 -2.4(2) . . . . ?
C6 C7 C8 C9 -179.41(15) . . . . ?
C2 C7 C8 C9 0.3(2) . . . . ?
C6 C7 C8 C28 -0.1(2) . . . . ?
C2 C7 C8 C28 179.68(14) . . . . ?
C7 C8 C9 C10 -179.45(15) . . . . ?
C28 C8 C9 C10 1.2(2) . . . . ?
C7 C8 C9 C14 1.9(2) . . . . ?
C28 C8 C9 C14 -177.43(14) . . . . ?
C8 C9 C10 C11 -177.85(16) . . . . ?
C14 C9 C10 C11 0.8(2) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C2 C1 C14 C13 -178.17(14) . . . . ?
N15 C1 C14 C13 1.0(2) . . . . ?
C2 C1 C14 C9 1.0(2) . . . . ?
N15 C1 C14 C9 -179.80(13) . . . . ?
C12 C13 C14 C1 -179.06(15) . . . . ?
C12 C13 C14 C9 1.8(2) . . . . ?
C8 C9 C14 C1 -2.5(2) . . . . ?
C10 C9 C14 C1 178.78(15) . . . . ?
C8 C9 C14 C13 176.67(15) . . . . ?
C10 C9 C14 C13 -2.0(2) . . . . ?
C27 N15 C16 C17 -179.65(15) . . . . ?
C1 N15 C16 C17 -2.6(2) . . . . ?
C27 N15 C16 C21 -0.16(16) . . . . ?
C1 N15 C16 C21 176.87(13) . . . . ?
N15 C16 C17 C18 179.84(15) . . . . ?
C21 C16 C17 C18 0.4(2) . . . . ?
C16 C17 C18 C19 -0.8(2) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C21 0.5(2) . . . . ?
C19 C20 C21 C16 -0.9(2) . . . . ?
C19 C20 C21 C22 179.51(16) . . . . ?
C17 C16 C21 C20 0.4(2) . . . . ?
N15 C16 C21 C20 -179.14(13) . . . . ?
C17 C16 C21 C22 -179.88(14) . . . . ?
N15 C16 C21 C22 0.58(16) . . . . ?
C20 C21 C22 C23 -2.2(3) . . . . ?
C16 C21 C22 C23 178.17(16) . . . . ?
C20 C21 C22 C27 178.88(16) . . . . ?
C16 C21 C22 C27 -0.78(16) . . . . ?
C27 C22 C23 C24 -0.4(2) . . . . ?
C21 C22 C23 C24 -179.28(16) . . . . ?
C22 C23 C24 C25 -0.7(2) . . . . ?
C23 C24 C25 C26 1.0(3) . . . . ?
C24 C25 C26 C27 0.0(2) . . . . ?
C25 C26 C27 N15 178.63(14) . . . . ?
C25 C26 C27 C22 -1.2(2) . . . . ?
C16 N15 C27 C26 179.78(15) . . . . ?
C1 N15 C27 C26 2.8(2) . . . . ?
C16 N15 C27 C22 -0.35(16) . . . . ?
C1 N15 C27 C22 -177.37(13) . . . . ?
C23 C22 C27 C26 1.4(2) . . . . ?
C21 C22 C27 C26 -179.42(14) . . . . ?
C23 C22 C27 N15 -178.43(13) . . . . ?
C21 C22 C27 N15 0.70(16) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene/hexane'
_exptl_crystal_preparation       Luminescent
