# 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. 
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#######################################################################

data_cd214210
_database_code_depnum_ccdc_archive 'CCDC 1016979'
_audit_update_record             
;
2014-07-30 deposited with the CCDC.
2015-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H30 N4'
_chemical_formula_weight         590.70

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                   17.624(4)
_cell_length_b                   13.658(3)
_cell_length_c                   14.035(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.504(4)
_cell_angle_gamma                90
_cell_volume                     3203.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2626
_cell_measurement_theta_min      4.875
_cell_measurement_theta_max      48.653

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6353
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9452
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.926
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3154
_reflns_number_gt                2383
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0925P)²+0.5869P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0095(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3154
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1670
_refine_ls_wR_factor_gt          0.1528
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
N1 N 0.71343(14) 1.16420(15) 0.1719(2) 0.1082(8) Uani 1 1 d . . . . .
N2 N 0.46382(16) 1.09895(15) 0.1132(3) 0.1258(11) Uani 1 1 d . . . . .
C1 C 0.37063(10) 0.56394(13) 0.05886(12) 0.0506(4) Uani 1 1 d . . . . .
C2 C 0.32626(11) 0.62046(16) -0.02215(13) 0.0643(5) Uani 1 1 d . . . . .
H2 H 0.3452 0.6809 -0.0351 0.077 Uiso 1 1 calc R U . . .
C3 C 0.25347(13) 0.5852(2) -0.08299(16) 0.0785(7) Uani 1 1 d . . . . .
H3 H 0.2226 0.6231 -0.1362 0.094 Uiso 1 1 calc R U . . .
C4 C 0.22625(14) 0.4949(2) -0.06578(17) 0.0873(8) Uani 1 1 d . . . . .
H4 H 0.1773 0.4722 -0.1077 0.105 Uiso 1 1 calc R U . . .
C5 C 0.27085(13) 0.43717(18) 0.01332(17) 0.0766(6) Uani 1 1 d . . . . .
H5 H 0.2526 0.3755 0.0240 0.092 Uiso 1 1 calc R U . . .
C6 C 0.34308(11) 0.47268(14) 0.07626(13) 0.0574(5) Uani 1 1 d . . . . .
C7 C 0.40281(11) 0.42414(12) 0.16501(13) 0.0548(5) Uani 1 1 d . . . . .
C8 C 0.46681(10) 0.50496(11) 0.20190(11) 0.0430(4) Uani 1 1 d . . . . .
C9 C 0.44808(9) 0.58148(11) 0.13662(12) 0.0441(4) Uani 1 1 d . . . . .
C10 C 0.49337(10) 0.67263(11) 0.13913(11) 0.0450(4) Uani 1 1 d . . . . .
C11 C 0.45345(10) 0.76251(12) 0.12439(13) 0.0522(5) Uani 1 1 d . . . . .
H11 H 0.3985 0.7638 0.1130 0.063 Uiso 1 1 calc R U . . .
C12 C 0.49368(11) 0.84868(13) 0.12641(14) 0.0562(5) Uani 1 1 d . . . . .
H12 H 0.4657 0.9075 0.1166 0.067 Uiso 1 1 calc R U . . .
C13 C 0.57638(11) 0.84934(12) 0.14311(13) 0.0527(4) Uani 1 1 d . . . . .
C14 C 0.61583(10) 0.75986(13) 0.15587(14) 0.0544(5) Uani 1 1 d . . . . .
H14 H 0.6706 0.7585 0.1660 0.065 Uiso 1 1 calc R U . . .
C15 C 0.57537(10) 0.67300(12) 0.15384(12) 0.0498(4) Uani 1 1 d . . . . .
H15 H 0.6031 0.6140 0.1624 0.060 Uiso 1 1 calc R U . . .
C16 C 0.62457(11) 0.93683(14) 0.15051(14) 0.0603(5) Uani 1 1 d . . . . .
H16 H 0.6784 0.9248 0.1599 0.072 Uiso 1 1 calc R U . . .
C17 C 0.60523(12) 1.03178(13) 0.14627(13) 0.0588(5) Uani 1 1 d . . . . .
C18 C 0.66573(14) 1.10558(15) 0.15997(17) 0.0755(6) Uani 1 1 d . . . . .
C19 C 0.52651(15) 1.06857(15) 0.12849(19) 0.0752(6) Uani 1 1 d . . . . .
C20 C 0.36459(14) 0.39786(16) 0.24602(16) 0.0765(6) Uani 1 1 d . . . . .
H20A H 0.3395 0.4549 0.2626 0.115 Uiso 1 1 calc R U . . .
H20B H 0.4052 0.3746 0.3050 0.115 Uiso 1 1 calc R U . . .
H20C H 0.3252 0.3476 0.2211 0.115 Uiso 1 1 calc R U . . .
C21 C 0.43368(16) 0.33233(15) 0.12512(19) 0.0872(7) Uani 1 1 d . . . . .
H21A H 0.3895 0.2897 0.0935 0.131 Uiso 1 1 calc R U . . .
H21B H 0.4714 0.2986 0.1800 0.131 Uiso 1 1 calc R U . . .
H21C H 0.4593 0.3515 0.0770 0.131 Uiso 1 1 calc R U . . .


_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 C18 1.134(3) . ?
N2 C19 1.135(3) . ?
C1 C6 1.387(2) . ?
C1 C2 1.391(3) . ?
C1 C9 1.472(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.506(3) . ?
C7 C20 1.537(3) . ?
C7 C21 1.541(3) . ?
C7 C8 1.545(2) . ?
C8 C9 1.360(2) . ?
C8 C8 1.479(3) 2_655 ?
C9 C10 1.473(2) . ?
C10 C15 1.393(2) . ?
C10 C11 1.397(2) . ?
C11 C12 1.370(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.401(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(2) . ?
C13 C16 1.451(2) . ?
C14 C15 1.380(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.337(3) . ?
C16 H16 0.9300 . ?
C17 C19 1.421(3) . ?
C17 C18 1.435(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C6 C1 C2 120.33(17) . . ?
C6 C1 C9 108.05(15) . . ?
C2 C1 C9 131.62(16) . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C5 C6 C1 120.27(19) . . ?
C5 C6 C7 129.24(19) . . ?
C1 C6 C7 110.45(15) . . ?
C6 C7 C20 111.07(16) . . ?
C6 C7 C21 107.01(16) . . ?
C20 C7 C21 111.53(17) . . ?
C6 C7 C8 101.95(13) . . ?
C20 C7 C8 111.32(15) . . ?
C21 C7 C8 113.49(16) . . ?
C9 C8 C8 124.58(11) . 2_655 ?
C9 C8 C7 109.14(15) . . ?
C8 C8 C7 125.98(11) 2_655 . ?
C8 C9 C1 110.14(14) . . ?
C8 C9 C10 128.29(15) . . ?
C1 C9 C10 121.55(14) . . ?
C15 C10 C11 117.95(15) . . ?
C15 C10 C9 122.35(14) . . ?
C11 C10 C9 119.69(15) . . ?
C12 C11 C10 121.25(16) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.88(16) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 117.87(15) . . ?
C14 C13 C16 117.24(16) . . ?
C12 C13 C16 124.87(16) . . ?
C15 C14 C13 121.30(16) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C10 120.73(15) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C17 C16 C13 131.34(18) . . ?
C17 C16 H16 114.3 . . ?
C13 C16 H16 114.3 . . ?
C16 C17 C19 124.85(17) . . ?
C16 C17 C18 120.46(19) . . ?
C19 C17 C18 114.68(17) . . ?
N1 C18 C17 179.1(3) . . ?
N2 C19 C17 178.9(3) . . ?
C7 C20 H20A 109.5 . . ?
C7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 C21 H21A 109.5 . . ?
C7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C6 C1 C2 C3 1.8(3) . . . . ?
C9 C1 C2 C3 -179.00(18) . . . . ?
C1 C2 C3 C4 -1.8(3) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C4 C5 C6 C7 -178.6(2) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C9 C1 C6 C5 -179.70(17) . . . . ?
C2 C1 C6 C7 177.57(16) . . . . ?
C9 C1 C6 C7 -1.82(19) . . . . ?
C5 C6 C7 C20 -59.5(3) . . . . ?
C1 C6 C7 C20 122.88(17) . . . . ?
C5 C6 C7 C21 62.5(3) . . . . ?
C1 C6 C7 C21 -115.18(17) . . . . ?
C5 C6 C7 C8 -178.15(19) . . . . ?
C1 C6 C7 C8 4.21(18) . . . . ?
C6 C7 C8 C9 -5.29(17) . . . . ?
C20 C7 C8 C9 -123.77(17) . . . . ?
C21 C7 C8 C9 109.42(18) . . . . ?
C6 C7 C8 C8 168.60(17) . . . 2_655 ?
C20 C7 C8 C8 50.1(2) . . . 2_655 ?
C21 C7 C8 C8 -76.7(2) . . . 2_655 ?
C8 C8 C9 C1 -169.46(17) 2_655 . . . ?
C7 C8 C9 C1 4.53(18) . . . . ?
C8 C8 C9 C10 8.6(3) 2_655 . . . ?
C7 C8 C9 C10 -177.37(14) . . . . ?
C6 C1 C9 C8 -1.79(19) . . . . ?
C2 C1 C9 C8 178.92(18) . . . . ?
C6 C1 C9 C10 179.96(14) . . . . ?
C2 C1 C9 C10 0.7(3) . . . . ?
C8 C9 C10 C15 47.6(2) . . . . ?
C1 C9 C10 C15 -134.50(17) . . . . ?
C8 C9 C10 C11 -133.72(18) . . . . ?
C1 C9 C10 C11 44.2(2) . . . . ?
C15 C10 C11 C12 -1.4(3) . . . . ?
C9 C10 C11 C12 179.89(16) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C11 C12 C13 C16 -177.43(17) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C16 C13 C14 C15 177.55(17) . . . . ?
C13 C14 C15 C10 -0.2(3) . . . . ?
C11 C10 C15 C14 1.4(2) . . . . ?
C9 C10 C15 C14 -179.92(15) . . . . ?
C14 C13 C16 C17 -176.73(19) . . . . ?
C12 C13 C16 C17 1.7(3) . . . . ?
C13 C16 C17 C19 -2.7(3) . . . . ?
C13 C16 C17 C18 177.4(2) . . . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.101

_shelxl_version_number           2013-4

