# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1008378'
_audit_update_record             
;
2015-07-24 deposited with the CCDC.
2015-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H30 N4'
_chemical_formula_weight         662.76

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   24.996(5)
_cell_length_b                   9.4441(19)
_cell_length_c                   14.619(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3450.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1384
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29007
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3915
_reflns_number_gt                2435
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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     
'calc w=1/[σ²(Fo²)+(0.0621P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3915
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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
N2 N 0.40909(4) 1.04196(12) 0.44880(8) 0.0468(3) Uani 1 1 d . . .
C2 C 0.34883(6) 0.70819(16) 0.39627(10) 0.0533(4) Uani 1 1 d . . .
N1 N 0.41222(5) 0.88736(14) 0.33243(8) 0.0521(3) Uani 1 1 d . . .
C4 C 0.5000 1.0293(2) 0.2500 0.0490(5) Uani 1 2 d S . .
H4 H 0.5000 0.9308 0.2500 0.059 Uiso 1 2 calc SR . .
C5 C 0.37927(6) 0.83619(16) 0.40029(10) 0.0498(4) Uani 1 1 d . . .
C6 C 0.31114(6) 0.77696(17) 0.54799(10) 0.0536(4) Uani 1 1 d . . .
C7 C 0.34529(6) 0.89870(16) 0.55365(10) 0.0496(4) Uani 1 1 d . . .
C8 C 0.37658(5) 0.92817(15) 0.47321(10) 0.0478(3) Uani 1 1 d . . .
C9 C 0.41883(6) 1.17004(15) 0.49973(9) 0.0477(3) Uani 1 1 d . . .
C10 C 0.5000 1.3200(2) 0.2500 0.0582(6) Uani 1 2 d S . .
H10 H 0.5000 1.4184 0.2500 0.070 Uiso 1 2 calc SR . .
C11 C 0.46511(6) 1.10074(16) 0.30798(10) 0.0482(3) Uani 1 1 d . . .
C12 C 0.31230(6) 0.68286(16) 0.46829(11) 0.0549(4) Uani 1 1 d . . .
C13 C 0.46492(7) 1.24836(17) 0.30678(10) 0.0553(4) Uani 1 1 d . . .
H13 H 0.4414 1.2984 0.3439 0.066 Uiso 1 1 calc R . .
C14 C 0.42907(5) 1.01101(16) 0.36268(9) 0.0481(3) Uani 1 1 d . . .
C15 C 0.34679(6) 0.97768(18) 0.63511(10) 0.0591(4) Uani 1 1 d . . .
H15 H 0.3704 1.0534 0.6403 0.071 Uiso 1 1 calc R . .
C16 C 0.27759(7) 0.7496(2) 0.62341(13) 0.0669(5) Uani 1 1 d . . .
H16 H 0.2541 0.6734 0.6207 0.080 Uiso 1 1 calc R . .
C17 C 0.37775(7) 1.26410(18) 0.51359(11) 0.0624(4) Uani 1 1 d . . .
H17 H 0.3436 1.2441 0.4921 0.075 Uiso 1 1 calc R . .
C18 C 0.27856(7) 0.8318(2) 0.70057(13) 0.0732(5) Uani 1 1 d . . .
H18 H 0.2554 0.8119 0.7487 0.088 Uiso 1 1 calc R . .
C19 C 0.35383(7) 0.61225(18) 0.32389(12) 0.0660(5) Uani 1 1 d . . .
H19 H 0.3786 0.6291 0.2777 0.079 Uiso 1 1 calc R . .
C20 C 0.27952(7) 0.56171(19) 0.46071(13) 0.0683(5) Uani 1 1 d . . .
H20 H 0.2540 0.5440 0.5056 0.082 Uiso 1 1 calc R . .
C21 C 0.31377(7) 0.9444(2) 0.70732(12) 0.0674(5) Uani 1 1 d . . .
H21 H 0.3151 0.9977 0.7608 0.081 Uiso 1 1 calc R . .
C22 C 0.46938(7) 1.19931(18) 0.53203(11) 0.0639(4) Uani 1 1 d . . .
H22 H 0.4970 1.1346 0.5235 0.077 Uiso 1 1 calc R . .
C23 C 0.28444(8) 0.4700(2) 0.38910(13) 0.0781(6) Uani 1 1 d . . .
H23 H 0.2622 0.3912 0.3859 0.094 Uiso 1 1 calc R . .
C24 C 0.32225(8) 0.4929(2) 0.32076(13) 0.0763(5) Uani 1 1 d . . .
H24 H 0.3261 0.4281 0.2733 0.092 Uiso 1 1 calc R . .
C25 C 0.38774(9) 1.3889(2) 0.55993(12) 0.0794(6) Uani 1 1 d . . .
H25 H 0.3600 1.4524 0.5705 0.095 Uiso 1 1 calc R . .
C26 C 0.43785(10) 1.4196(2) 0.59007(14) 0.0881(6) Uani 1 1 d . . .
H26 H 0.4444 1.5051 0.6196 0.106 Uiso 1 1 calc R . .
C27 C 0.47878(9) 1.3252(2) 0.57708(14) 0.0853(6) Uani 1 1 d . . .
H27 H 0.5129 1.3460 0.5986 0.102 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
N2 C14 1.3855(18) . ?
N2 C8 1.3938(18) . ?
N2 C9 1.4411(18) . ?
C2 C19 1.399(2) . ?
C2 C12 1.414(2) . ?
C2 C5 1.430(2) . ?
N1 C14 1.3178(19) . ?
N1 C5 1.3770(18) . ?
C4 C11 1.3908(17) . ?
C4 C11 1.3908(17) 3_655 ?
C5 C8 1.377(2) . ?
C6 C16 1.409(2) . ?
C6 C7 1.434(2) . ?
C6 C12 1.466(2) . ?
C7 C15 1.406(2) . ?
C7 C8 1.439(2) . ?
C9 C17 1.373(2) . ?
C9 C22 1.377(2) . ?
C10 C13 1.3839(19) . ?
C10 C13 1.3839(19) 3_655 ?
C11 C13 1.394(2) . ?
C11 C14 1.473(2) . ?
C12 C20 1.412(2) . ?
C15 C21 1.376(2) . ?
C16 C18 1.369(3) . ?
C17 C25 1.382(2) . ?
C18 C21 1.384(3) . ?
C19 C24 1.377(2) . ?
C20 C23 1.364(3) . ?
C22 C27 1.379(2) . ?
C23 C24 1.392(3) . ?
C25 C26 1.359(3) . ?
C26 C27 1.370(3) . ?

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
C14 N2 C8 106.27(12) . . ?
C14 N2 C9 125.85(11) . . ?
C8 N2 C9 127.83(11) . . ?
C19 C2 C12 120.75(15) . . ?
C19 C2 C5 122.10(15) . . ?
C12 C2 C5 117.14(14) . . ?
C14 N1 C5 105.09(12) . . ?
C11 C4 C11 122.0(2) . 3_655 ?
C8 C5 N1 111.45(13) . . ?
C8 C5 C2 122.64(14) . . ?
N1 C5 C2 125.84(14) . . ?
C16 C6 C7 117.12(15) . . ?
C16 C6 C12 121.51(15) . . ?
C7 C6 C12 121.34(13) . . ?
C15 C7 C6 119.34(14) . . ?
C15 C7 C8 125.10(14) . . ?
C6 C7 C8 115.54(13) . . ?
C5 C8 N2 105.05(12) . . ?
C5 C8 C7 122.48(13) . . ?
N2 C8 C7 132.46(13) . . ?
C17 C9 C22 120.39(15) . . ?
C17 C9 N2 119.55(13) . . ?
C22 C9 N2 120.04(13) . . ?
C13 C10 C13 121.5(2) . 3_655 ?
C4 C11 C13 118.65(15) . . ?
C4 C11 C14 115.81(14) . . ?
C13 C11 C14 125.46(14) . . ?
C20 C12 C2 116.97(16) . . ?
C20 C12 C6 122.85(15) . . ?
C2 C12 C6 120.13(13) . . ?
C10 C13 C11 119.61(16) . . ?
N1 C14 N2 112.13(12) . . ?
N1 C14 C11 121.55(13) . . ?
N2 C14 C11 126.33(13) . . ?
C21 C15 C7 120.85(16) . . ?
C18 C16 C6 122.00(17) . . ?
C9 C17 C25 119.27(16) . . ?
C16 C18 C21 120.37(16) . . ?
C24 C19 C2 120.29(18) . . ?
C23 C20 C12 121.48(17) . . ?
C15 C21 C18 120.14(17) . . ?
C9 C22 C27 119.54(16) . . ?
C20 C23 C24 120.90(17) . . ?
C19 C24 C23 119.50(18) . . ?
C26 C25 C17 120.49(18) . . ?
C25 C26 C27 120.28(18) . . ?
C26 C27 C22 120.00(18) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.102
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.032
