# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_ic16051
_database_code_depnum_ccdc_archive 'CCDC 1008747'
_audit_update_record             
;
2015-07-02 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H32 N2'
_chemical_formula_weight         660.78

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.8317(4)
_cell_length_b                   7.8512(3)
_cell_length_c                   17.4533(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.411(2)
_cell_angle_gamma                90.00
_cell_volume                     1758.27(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    10927
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.00

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             692
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'NONIUS KappaCCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10927
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_sigmaI/netI    0.0752
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3090
_reflns_number_gt                1482
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'NONIUS COLLECT'
_computing_cell_refinement       DENZO-SMN
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0591P)²+0.2078P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3090
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1489
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1587
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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
N1 N 0.3146(2) 0.3581(4) 0.17446(19) 0.0863(9) Uani 1 1 d . . .
C1 C -0.0182(3) 1.1424(4) 0.20217(18) 0.0740(9) Uani 1 1 d . . .
H1 H -0.0057 1.1511 0.2546 0.089 Uiso 1 1 calc R . .
C2 C 0.0345(2) 1.0258(4) 0.16042(18) 0.0620(8) Uani 1 1 d . . .
H2 H 0.0820 0.9546 0.1850 0.074 Uiso 1 1 calc R . .
C3 C 0.0190(2) 1.0091(3) 0.07961(16) 0.0500(7) Uani 1 1 d . . .
C4 C 0.0704(2) 0.8852(3) 0.03650(16) 0.0495(7) Uani 1 1 d . . .
C5 C 0.0528(2) 0.8757(3) -0.04303(16) 0.0513(7) Uani 1 1 d . . .
C6 C 0.1076(2) 0.7583(4) -0.08994(19) 0.0689(9) Uani 1 1 d . . .
H6 H 0.1559 0.6854 -0.0672 0.083 Uiso 1 1 calc R . .
C7 C 0.0917(3) 0.7494(4) -0.16696(19) 0.0774(10) Uani 1 1 d . . .
H7 H 0.1292 0.6720 -0.1962 0.093 Uiso 1 1 calc R . .
C8 C 0.1368(2) 0.7532(3) 0.07445(16) 0.0542(7) Uani 1 1 d . . .
C9 C 0.0976(2) 0.5910(4) 0.08289(17) 0.0642(9) Uani 1 1 d . . .
H9 H 0.0302 0.5678 0.0661 0.077 Uiso 1 1 calc R . .
C10 C 0.1560(2) 0.4621(4) 0.11561(18) 0.0707(9) Uani 1 1 d . . .
H10 H 0.1282 0.3531 0.1199 0.085 Uiso 1 1 calc R . .
C11 C 0.2543(2) 0.4947(4) 0.1416(2) 0.0721(10) Uani 1 1 d . . .
C12 C 0.2952(3) 0.6550(4) 0.1347(2) 0.0924(13) Uani 1 1 d . . .
H12 H 0.3623 0.6775 0.1525 0.111 Uiso 1 1 calc R . .
C13 C 0.2361(2) 0.7840(4) 0.1012(2) 0.0835(11) Uani 1 1 d . . .
H13 H 0.2643 0.8927 0.0968 0.100 Uiso 1 1 calc R . .
C14 C 0.2942(3) 0.2762(4) 0.2448(3) 0.0902(13) Uani 1 1 d . . .
C15 C 0.2232(3) 0.3167(6) 0.2995(3) 0.1062(15) Uani 1 1 d . . .
H15 H 0.1762 0.4055 0.2923 0.127 Uiso 1 1 calc R . .
C16 C 0.2233(3) 0.2207(6) 0.3667(3) 0.1279(18) Uani 1 1 d . . .
H16 H 0.1773 0.2462 0.4060 0.153 Uiso 1 1 calc R . .
C17 C 0.2939(5) 0.0845(8) 0.3744(4) 0.141(3) Uani 1 1 d . . .
H17 H 0.2917 0.0181 0.4185 0.170 Uiso 1 1 calc R . .
C18 C 0.3640(4) 0.0469(6) 0.3208(4) 0.125(2) Uani 1 1 d . . .
H18 H 0.4111 -0.0417 0.3284 0.150 Uiso 1 1 calc R . .
C19 C 0.3661(3) 0.1428(5) 0.2526(3) 0.0974(14) Uani 1 1 d . . .
C20 C 0.4306(3) 0.1419(4) 0.1851(3) 0.0960(14) Uani 1 1 d . . .
C21 C 0.5152(4) 0.0441(6) 0.1614(4) 0.135(2) Uani 1 1 d . . .
H21 H 0.5398 -0.0449 0.1917 0.162 Uiso 1 1 calc R . .
C22 C 0.5616(5) 0.0810(8) 0.0927(4) 0.148(3) Uani 1 1 d . . .
H22 H 0.6190 0.0175 0.0773 0.178 Uiso 1 1 calc R . .
C23 C 0.5250(4) 0.2108(6) 0.0457(3) 0.1280(17) Uani 1 1 d . . .
H23 H 0.5572 0.2310 -0.0010 0.154 Uiso 1 1 calc R . .
C24 C 0.4417(3) 0.3101(5) 0.0672(3) 0.1009(14) Uani 1 1 d . . .
H24 H 0.4165 0.3967 0.0358 0.121 Uiso 1 1 calc R . .
C25 C 0.3972(3) 0.2761(4) 0.1372(3) 0.0858(12) 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
N1 C25 1.404(5) . ?
N1 C14 1.412(5) . ?
N1 C11 1.439(4) . ?
C1 C2 1.354(4) . ?
C1 C7 1.407(4) 3_575 ?
C2 C3 1.429(4) . ?
C3 C4 1.398(4) . ?
C3 C5 1.437(4) 3_575 ?
C4 C5 1.407(4) . ?
C4 C8 1.494(4) . ?
C5 C6 1.422(4) . ?
C5 C3 1.437(4) 3_575 ?
C6 C7 1.360(4) . ?
C7 C1 1.407(4) 3_575 ?
C8 C9 1.377(4) . ?
C8 C13 1.376(4) . ?
C9 C10 1.380(4) . ?
C10 C11 1.362(4) . ?
C11 C12 1.369(4) . ?
C12 C13 1.392(4) . ?
C14 C15 1.362(5) . ?
C14 C19 1.402(5) . ?
C15 C16 1.394(5) . ?
C16 C17 1.407(7) . ?
C17 C18 1.336(7) . ?
C18 C19 1.409(6) . ?
C19 C20 1.444(6) . ?
C20 C21 1.394(7) . ?
C20 C25 1.410(5) . ?
C21 C22 1.375(8) . ?
C22 C23 1.388(7) . ?
C23 C24 1.378(5) . ?
C24 C25 1.377(5) . ?

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
C25 N1 C14 109.8(3) . . ?
C25 N1 C11 124.2(3) . . ?
C14 N1 C11 125.7(3) . . ?
C2 C1 C7 120.6(3) . 3_575 ?
C1 C2 C3 121.8(3) . . ?
C4 C3 C2 122.2(3) . . ?
C4 C3 C5 120.1(2) . 3_575 ?
C2 C3 C5 117.7(3) . 3_575 ?
C3 C4 C5 119.7(2) . . ?
C3 C4 C8 120.9(2) . . ?
C5 C4 C8 119.2(3) . . ?
C4 C5 C6 121.7(2) . . ?
C4 C5 C3 120.2(2) . 3_575 ?
C6 C5 C3 118.1(3) . 3_575 ?
C7 C6 C5 122.1(3) . . ?
C6 C7 C1 119.7(3) . 3_575 ?
C9 C8 C13 117.7(2) . . ?
C9 C8 C4 118.8(2) . . ?
C13 C8 C4 123.5(3) . . ?
C8 C9 C10 121.7(3) . . ?
C11 C10 C9 119.9(3) . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 N1 119.1(3) . . ?
C12 C11 N1 120.9(3) . . ?
C11 C12 C13 119.8(3) . . ?
C8 C13 C12 121.0(3) . . ?
C15 C14 C19 123.3(5) . . ?
C15 C14 N1 129.3(3) . . ?
C19 C14 N1 107.4(5) . . ?
C14 C15 C16 117.9(4) . . ?
C15 C16 C17 119.2(5) . . ?
C18 C17 C16 122.5(5) . . ?
C17 C18 C19 119.4(5) . . ?
C14 C19 C18 117.7(5) . . ?
C14 C19 C20 107.8(4) . . ?
C18 C19 C20 134.4(4) . . ?
C21 C20 C25 118.0(6) . . ?
C21 C20 C19 134.1(5) . . ?
C25 C20 C19 107.8(4) . . ?
C22 C21 C20 119.1(5) . . ?
C21 C22 C23 121.6(6) . . ?
C24 C23 C22 120.9(6) . . ?
C23 C24 C25 117.4(4) . . ?
C24 C25 N1 129.9(4) . . ?
C24 C25 C20 122.9(4) . . ?
N1 C25 C20 107.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.031
