# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1431519'
_audit_update_record             
;
2015-10-15 deposited with the CCDC.
2016-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C58 H42 N4'
_chemical_formula_weight         794.95

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.9142(17)
_cell_length_b                   13.574(2)
_cell_length_c                   14.539(2)
_cell_angle_alpha                90
_cell_angle_beta                 76.691(8)
_cell_angle_gamma                90
_cell_volume                     2096.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3880
_cell_measurement_theta_min      1
_cell_measurement_theta_max      25.35

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             836
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.018
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_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_source                   'Enraf Nonius FR590'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            7210
_diffrn_reflns_av_unetI/netI     0.2232
_diffrn_reflns_av_R_equivalents  0.1898
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.194
_diffrn_reflns_theta_max         25.258
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3743
_reflns_number_gt                1096
_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       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SIR-97 (Altomare al, 1999)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_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)+(0.1344P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3743
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2867
_refine_ls_R_factor_gt           0.0919
_refine_ls_wR_factor_ref         0.3083
_refine_ls_wR_factor_gt          0.2180
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_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 0.0080(6) 0.5416(6) 0.0309(5) 0.105(3) Uani 1 1 d . . . . .
H1 H 0.0050 0.6004 -0.0077 0.126 Uiso 1 1 calc R U . . .
C2 C 0.1333(6) 0.5493(6) 0.0596(4) 0.0811(19) Uani 1 1 d . . . . .
C3 C 0.1935(6) 0.4657(6) 0.0868(5) 0.088(2) Uani 1 1 d . . . . .
H3 H 0.1583 0.4033 0.0869 0.106 Uiso 1 1 calc R U . . .
C4 C 0.3111(6) 0.4797(5) 0.1144(4) 0.0729(17) Uani 1 1 d . . . . .
C5 C 0.3003(5) 0.6471(6) 0.0907(4) 0.0772(19) Uani 1 1 d . . . . .
C6 C 0.1884(6) 0.6390(6) 0.0624(5) 0.0852(19) Uani 1 1 d . . . . .
H6 H 0.1504 0.6952 0.0452 0.102 Uiso 1 1 calc R U . . .
C7 C 0.3599(6) 0.7455(6) 0.0946(4) 0.0794(19) Uani 1 1 d . . . . .
C8 C 0.4892(6) 0.7506(6) 0.0801(4) 0.087(2) Uani 1 1 d . . . . .
H8 H 0.5369 0.6933 0.0675 0.105 Uiso 1 1 calc R U . . .
C9 C 0.5487(7) 0.8399(7) 0.0841(5) 0.100(2) Uani 1 1 d . . . . .
H9 H 0.6360 0.8423 0.0738 0.120 Uiso 1 1 calc R U . . .
C10 C 0.4797(9) 0.9252(7) 0.1031(6) 0.110(3) Uani 1 1 d . . . . .
H10 H 0.5195 0.9852 0.1071 0.132 Uiso 1 1 calc R U . . .
C11 C 0.3499(9) 0.9206(6) 0.1163(6) 0.107(3) Uani 1 1 d . . . . .
H11 H 0.3022 0.9779 0.1273 0.129 Uiso 1 1 calc R U . . .
C12 C 0.2923(7) 0.8318(6) 0.1130(5) 0.093(2) Uani 1 1 d . . . . .
H12 H 0.2050 0.8296 0.1234 0.112 Uiso 1 1 calc R U . . .
C13 C 0.3825(6) 0.3971(6) 0.1398(5) 0.0789(18) Uani 1 1 d . . . . .
C14 C 0.3282(7) 0.3061(7) 0.1628(5) 0.101(2) Uani 1 1 d . . . . .
H14 H 0.2436 0.2978 0.1631 0.121 Uiso 1 1 calc R U . . .
C15 C 0.3943(8) 0.2277(6) 0.1853(5) 0.105(2) Uani 1 1 d . . . . .
H15 H 0.3547 0.1671 0.1989 0.126 Uiso 1 1 calc R U . . .
C16 C 0.5201(8) 0.2380(7) 0.1879(5) 0.105(2) Uani 1 1 d . . . . .
H16 H 0.5653 0.1852 0.2039 0.126 Uiso 1 1 calc R U . . .
C17 C 0.5762(7) 0.3293(7) 0.1660(6) 0.104(2) Uani 1 1 d . . . . .
H17 H 0.6604 0.3381 0.1670 0.124 Uiso 1 1 calc R U . . .
C18 C 0.5092(6) 0.4058(5) 0.1430(5) 0.093(2) Uani 1 1 d . . . . .
H18 H 0.5489 0.4664 0.1288 0.112 Uiso 1 1 calc R U . . .
C19 C -0.1028(6) 0.5541(6) 0.1165(5) 0.083(2) Uani 1 1 d . . . . .
C20 C -0.1259(6) 0.4894(5) 0.1914(6) 0.088(2) Uani 1 1 d . . . . .
H20 H -0.0742 0.4346 0.1898 0.105 Uiso 1 1 calc R U . . .
C21 C -0.2269(6) 0.5046(5) 0.2712(5) 0.089(2) Uani 1 1 d . . . . .
H21 H -0.2415 0.4602 0.3213 0.107 Uiso 1 1 calc R U . . .
C22 C -0.3039(6) 0.5871(5) 0.2735(5) 0.0758(18) Uani 1 1 d . . . . .
C23 C -0.2773(6) 0.6508(5) 0.1981(5) 0.0854(19) Uani 1 1 d . . . . .
H23 H -0.3281 0.7060 0.1995 0.102 Uiso 1 1 calc R U . . .
C24 C -0.1802(7) 0.6371(5) 0.1211(5) 0.089(2) Uani 1 1 d . . . . .
H24 H -0.1656 0.6827 0.0720 0.107 Uiso 1 1 calc R U . . .
C25 C -0.4096(6) 0.6036(5) 0.3545(5) 0.0739(17) Uani 1 1 d . . . . .
C26 C -0.3962(6) 0.6061(5) 0.4467(6) 0.0850(19) Uani 1 1 d . . . . .
H26 H -0.3172 0.5961 0.4590 0.102 Uiso 1 1 calc R U . . .
C27 C -0.4980(7) 0.6230(5) 0.5205(5) 0.093(2) Uani 1 1 d . . . . .
H27 H -0.4843 0.6251 0.5813 0.112 Uiso 1 1 calc R U . . .
C28 C -0.6298(6) 0.6332(5) 0.4208(7) 0.092(2) Uani 1 1 d . . . . .
H28 H -0.7106 0.6402 0.4109 0.111 Uiso 1 1 calc R U . . .
C29 C -0.5319(6) 0.6196(5) 0.3419(5) 0.092(2) Uani 1 1 d . . . . .
H29 H -0.5471 0.6210 0.2815 0.110 Uiso 1 1 calc R U . . .
N1 N 0.3599(4) 0.5696(4) 0.1158(4) 0.0760(15) Uani 1 1 d . . . . .
N2 N -0.6167(5) 0.6369(4) 0.5102(5) 0.0980(18) 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 C1 1.479(13) 3_565 ?
C1 C2 1.522(8) . ?
C1 C19 1.532(9) . ?
C2 C6 1.364(9) . ?
C2 C3 1.414(9) . ?
C3 C4 1.443(8) . ?
C4 N1 1.334(7) . ?
C4 C13 1.461(9) . ?
C5 N1 1.331(7) . ?
C5 C6 1.379(8) . ?
C5 C7 1.494(9) . ?
C7 C12 1.378(9) . ?
C7 C8 1.380(8) . ?
C8 C9 1.383(9) . ?
C9 C10 1.374(10) . ?
C10 C11 1.386(10) . ?
C11 C12 1.365(9) . ?
C13 C14 1.377(9) . ?
C13 C18 1.399(8) . ?
C14 C15 1.366(10) . ?
C15 C16 1.389(10) . ?
C16 C17 1.387(10) . ?
C17 C18 1.356(9) . ?
C19 C20 1.378(9) . ?
C19 C24 1.400(9) . ?
C20 C21 1.419(9) . ?
C21 C22 1.395(9) . ?
C22 C23 1.375(8) . ?
C22 C25 1.463(9) . ?
C23 C24 1.365(9) . ?
C25 C26 1.382(8) . ?
C25 C29 1.406(8) . ?
C26 C27 1.375(9) . ?
C27 N2 1.351(8) . ?
C28 N2 1.340(9) . ?
C28 C29 1.388(9) . ?

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
C1 C1 C2 117.2(7) 3_565 . ?
C1 C1 C19 113.4(7) 3_565 . ?
C2 C1 C19 111.1(5) . . ?
C6 C2 C3 118.1(6) . . ?
C6 C2 C1 120.0(7) . . ?
C3 C2 C1 121.8(7) . . ?
C2 C3 C4 118.2(7) . . ?
N1 C4 C3 120.6(6) . . ?
N1 C4 C13 117.4(6) . . ?
C3 C4 C13 122.0(7) . . ?
N1 C5 C6 122.8(7) . . ?
N1 C5 C7 116.8(5) . . ?
C6 C5 C7 120.4(6) . . ?
C2 C6 C5 120.5(7) . . ?
C12 C7 C8 118.1(7) . . ?
C12 C7 C5 123.3(6) . . ?
C8 C7 C5 118.6(7) . . ?
C9 C8 C7 120.7(7) . . ?
C8 C9 C10 120.4(7) . . ?
C9 C10 C11 119.0(8) . . ?
C12 C11 C10 120.0(7) . . ?
C11 C12 C7 121.7(7) . . ?
C14 C13 C18 116.2(7) . . ?
C14 C13 C4 121.6(6) . . ?
C18 C13 C4 122.2(7) . . ?
C15 C14 C13 122.4(8) . . ?
C14 C15 C16 120.5(8) . . ?
C15 C16 C17 118.1(7) . . ?
C18 C17 C16 120.4(8) . . ?
C17 C18 C13 122.5(7) . . ?
C20 C19 C24 118.5(6) . . ?
C20 C19 C1 122.6(7) . . ?
C24 C19 C1 118.9(7) . . ?
C19 C20 C21 121.3(6) . . ?
C22 C21 C20 119.1(7) . . ?
C23 C22 C21 118.0(7) . . ?
C23 C22 C25 121.9(6) . . ?
C21 C22 C25 120.1(7) . . ?
C24 C23 C22 123.4(7) . . ?
C23 C24 C19 119.7(7) . . ?
C26 C25 C29 116.0(6) . . ?
C26 C25 C22 123.0(6) . . ?
C29 C25 C22 121.0(6) . . ?
C27 C26 C25 120.9(6) . . ?
N2 C27 C26 124.1(7) . . ?
N2 C28 C29 124.9(6) . . ?
C28 C29 C25 119.1(7) . . ?
C4 N1 C5 119.8(6) . . ?
C28 N2 C27 114.9(6) . . ?

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

