# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_m11
_database_code_depnum_ccdc_archive 'CCDC 1415851'
_audit_update_record             
;
2015-07-30 deposited with the CCDC.
2016-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C47 H32 N2'
_chemical_formula_weight         624.75

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)

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

_cell_length_a                   12.390(3)
_cell_length_b                   5.9175(12)
_cell_length_c                   23.356(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.62(3)
_cell_angle_gamma                90.00
_cell_volume                     1704.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.754
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.131
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.991
_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  'Rigaku RAXIS-RAPID'
_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            16200
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_sigmaI/netI    0.2856
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.24
_diffrn_reflns_theta_max         27.48
_reflns_number_total             7374
_reflns_number_gt                3760
_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)+(0.0693P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(5)
_refine_ls_number_reflns         7374
_refine_ls_number_parameters     442
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0699
_refine_ls_wR_factor_ref         0.1839
_refine_ls_wR_factor_gt          0.1546
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
N1 N 0.2554(3) 0.1368(5) 0.15087(12) 0.0487(7) Uani 1 1 d . . .
C7 C 0.3075(3) -0.0176(6) 0.11744(15) 0.0499(9) Uani 1 1 d . . .
C26 C 0.2200(3) 0.5961(6) 0.29968(14) 0.0467(9) Uani 1 1 d . . .
C25 C 0.2939(3) 0.7755(6) 0.30301(16) 0.0553(10) Uani 1 1 d . . .
H25 H 0.2849 0.8950 0.3280 0.066 Uiso 1 1 calc R . .
C8 C 0.2631(3) -0.1764(6) 0.07446(15) 0.0508(9) Uani 1 1 d . . .
C27 C 0.2342(3) 0.4235(6) 0.26071(15) 0.0481(9) Uani 1 1 d . . .
H27 H 0.1861 0.3025 0.2580 0.058 Uiso 1 1 calc R . .
C6 C 0.1408(3) 0.1505(6) 0.15571(14) 0.0471(9) Uani 1 1 d . . .
C20 C 0.4161(3) 0.0072(7) 0.13333(14) 0.0497(9) Uani 1 1 d . . .
C23 C 0.3924(3) 0.6055(6) 0.23117(15) 0.0515(9) Uani 1 1 d . . .
H23 H 0.4503 0.6089 0.2087 0.062 Uiso 1 1 calc R . .
C14 C 0.4555(4) -0.3213(7) 0.07673(16) 0.0571(11) Uani 1 1 d . . .
C22 C 0.3191(3) 0.4278(6) 0.22562(14) 0.0435(9) Uani 1 1 d . . .
C31 C -0.0426(3) 0.5692(7) 0.40781(15) 0.0508(9) Uani 1 1 d . . .
C13 C 0.3401(4) -0.3323(7) 0.05521(15) 0.0586(11) Uani 1 1 d . . .
C19 C 0.4943(4) -0.1416(7) 0.11315(16) 0.0550(10) Uani 1 1 d . . .
C9 C 0.1566(4) -0.1784(8) 0.04914(16) 0.0655(12) Uani 1 1 d . . .
H9 H 0.1078 -0.0718 0.0605 0.079 Uiso 1 1 calc R . .
C36 C -0.2964(3) 0.5016(6) 0.49180(14) 0.0470(9) Uani 1 1 d . . .
C28 C 0.1294(3) 0.5898(6) 0.33674(15) 0.0475(9) Uani 1 1 d . . .
C18 C 0.6038(4) -0.1304(8) 0.13272(17) 0.0629(11) Uani 1 1 d . . .
H18 H 0.6287 -0.0113 0.1564 0.075 Uiso 1 1 calc R . .
N2 N 0.4342(3) 0.1772(5) 0.17393(12) 0.0503(8) Uani 1 1 d . . .
C34 C -0.1262(3) 0.5646(6) 0.44819(15) 0.0510(10) Uani 1 1 d . . .
H34 H -0.1068 0.6415 0.4824 0.061 Uiso 1 1 calc R . .
C33 C 0.0307(3) 0.5016(8) 0.31695(16) 0.0611(11) Uani 1 1 d . . .
H33 H 0.0205 0.4477 0.2794 0.073 Uiso 1 1 calc R . .
C35 C -0.2246(3) 0.4712(6) 0.44526(14) 0.0463(9) Uani 1 1 d . . .
C17 C 0.6755(4) -0.2891(9) 0.1181(2) 0.0772(15) Uani 1 1 d . . .
H17 H 0.7485 -0.2780 0.1315 0.093 Uiso 1 1 calc R . .
C38 C -0.3542(4) 0.7130(8) 0.57187(17) 0.0671(12) Uani 1 1 d . . .
H38 H -0.3479 0.8398 0.5955 0.081 Uiso 1 1 calc R . .
C29 C 0.1405(3) 0.6769(7) 0.39169(15) 0.0579(10) Uani 1 1 d . . .
H29 H 0.2055 0.7451 0.4057 0.069 Uiso 1 1 calc R . .
C32 C -0.0544(3) 0.4900(8) 0.35096(16) 0.0613(11) Uani 1 1 d . . .
H32 H -0.1203 0.4288 0.3359 0.074 Uiso 1 1 calc R . .
C41 C -0.3705(3) 0.3372(8) 0.50276(16) 0.0586(10) Uani 1 1 d . . .
H41 H -0.3763 0.2083 0.4799 0.070 Uiso 1 1 calc R . .
C24 C 0.3796(3) 0.7774(7) 0.26990(16) 0.0576(10) Uani 1 1 d . . .
H24 H 0.4294 0.8953 0.2736 0.069 Uiso 1 1 calc R . .
C1 C 0.0832(4) 0.3384(7) 0.13479(17) 0.0622(11) Uani 1 1 d . . .
H1 H 0.1180 0.4543 0.1169 0.075 Uiso 1 1 calc R . .
C40 C -0.4363(4) 0.3594(9) 0.54686(17) 0.0659(12) Uani 1 1 d . . .
H40 H -0.4860 0.2465 0.5531 0.079 Uiso 1 1 calc R . .
C42 C -0.2663(3) 0.3252(6) 0.39592(14) 0.0472(9) Uani 1 1 d . . .
C30 C 0.0563(3) 0.6644(7) 0.42641(16) 0.0582(11) Uani 1 1 d . . .
H30 H 0.0667 0.7223 0.4636 0.070 Uiso 1 1 calc R . .
C4 C -0.0195(4) -0.0031(10) 0.1888(2) 0.0844(15) Uani 1 1 d . . .
H4 H -0.0548 -0.1174 0.2070 0.101 Uiso 1 1 calc R . .
C39 C -0.4286(4) 0.5453(9) 0.58125(18) 0.0692(13) Uani 1 1 d . . .
H39 H -0.4731 0.5599 0.6109 0.083 Uiso 1 1 calc R . .
C43 C -0.3485(3) 0.3912(7) 0.35566(16) 0.0584(10) Uani 1 1 d . . .
H43 H -0.3837 0.5275 0.3608 0.070 Uiso 1 1 calc R . .
C21 C 0.3375(3) 0.2455(6) 0.18408(15) 0.0476(9) Uani 1 1 d . . .
C2 C -0.0264(4) 0.3520(10) 0.1407(2) 0.0843(15) Uani 1 1 d . . .
H2 H -0.0661 0.4763 0.1262 0.101 Uiso 1 1 calc R . .
C45 C -0.3330(5) 0.0534(8) 0.3011(2) 0.0755(14) Uani 1 1 d . . .
H45 H -0.3541 -0.0356 0.2692 0.091 Uiso 1 1 calc R . .
C47 C -0.2209(4) 0.1107(7) 0.38912(18) 0.0679(12) Uani 1 1 d . . .
H47 H -0.1677 0.0561 0.4165 0.081 Uiso 1 1 calc R . .
C5 C 0.0905(3) -0.0206(8) 0.18290(17) 0.0616(11) Uani 1 1 d . . .
H5 H 0.1297 -0.1460 0.1971 0.074 Uiso 1 1 calc R . .
C37 C -0.2896(4) 0.6914(7) 0.52748(17) 0.0638(12) Uani 1 1 d . . .
H37 H -0.2404 0.8054 0.5211 0.077 Uiso 1 1 calc R . .
C44 C -0.3804(4) 0.2618(9) 0.30797(18) 0.0717(13) Uani 1 1 d . . .
H44 H -0.4337 0.3146 0.2804 0.086 Uiso 1 1 calc R . .
C15 C 0.5321(5) -0.4844(8) 0.06165(18) 0.0737(14) Uani 1 1 d . . .
H15 H 0.5095 -0.6028 0.0372 0.088 Uiso 1 1 calc R . .
C46 C -0.2552(5) -0.0190(8) 0.3419(2) 0.0790(14) Uani 1 1 d . . .
H46 H -0.2241 -0.1604 0.3377 0.095 Uiso 1 1 calc R . .
C12 C 0.2999(5) -0.4945(8) 0.01419(19) 0.0765(14) Uani 1 1 d . . .
H12 H 0.3468 -0.6038 0.0023 0.092 Uiso 1 1 calc R . .
C16 C 0.6387(5) -0.4687(9) 0.0827(2) 0.0803(15) Uani 1 1 d . . .
H16 H 0.6874 -0.5793 0.0734 0.096 Uiso 1 1 calc R . .
C10 C 0.1220(4) -0.3335(9) 0.00791(18) 0.0780(14) Uani 1 1 d . . .
H10 H 0.0509 -0.3310 -0.0090 0.094 Uiso 1 1 calc R . .
C3 C -0.0764(4) 0.1844(11) 0.1676(2) 0.0902(16) Uani 1 1 d . . .
H3 H -0.1500 0.1959 0.1719 0.108 Uiso 1 1 calc R . .
C11 C 0.1945(5) -0.4949(9) -0.0083(2) 0.0819(15) Uani 1 1 d . . .
H11 H 0.1706 -0.6050 -0.0350 0.098 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
N1 C21 1.377(5) . ?
N1 C7 1.400(4) . ?
N1 C6 1.437(5) . ?
C7 C20 1.368(5) . ?
C7 C8 1.444(5) . ?
C26 C27 1.391(5) . ?
C26 C25 1.399(5) . ?
C26 C28 1.483(5) . ?
C25 C24 1.373(5) . ?
C8 C9 1.392(6) . ?
C8 C13 1.431(5) . ?
C27 C22 1.395(5) . ?
C6 C5 1.376(5) . ?
C6 C1 1.384(5) . ?
C20 N2 1.386(5) . ?
C20 C19 1.424(5) . ?
C23 C24 1.381(5) . ?
C23 C22 1.387(5) . ?
C14 C19 1.417(6) . ?
C14 C15 1.422(6) . ?
C14 C13 1.470(6) . ?
C22 C21 1.483(5) . ?
C31 C30 1.380(5) . ?
C31 C32 1.402(5) . ?
C31 C34 1.467(5) . ?
C13 C12 1.412(6) . ?
C19 C18 1.390(6) . ?
C9 C10 1.369(6) . ?
C36 C41 1.379(5) . ?
C36 C37 1.396(5) . ?
C36 C35 1.481(5) . ?
C28 C33 1.368(5) . ?
C28 C29 1.377(5) . ?
C18 C17 1.359(6) . ?
N2 C21 1.307(5) . ?
C34 C35 1.335(5) . ?
C33 C32 1.382(5) . ?
C35 C42 1.492(5) . ?
C17 C16 1.395(7) . ?
C38 C37 1.376(5) . ?
C38 C39 1.387(6) . ?
C29 C30 1.385(5) . ?
C41 C40 1.381(5) . ?
C1 C2 1.381(6) . ?
C40 C39 1.360(7) . ?
C42 C43 1.374(5) . ?
C42 C47 1.404(5) . ?
C4 C3 1.380(8) . ?
C4 C5 1.388(6) . ?
C43 C44 1.377(6) . ?
C2 C3 1.356(7) . ?
C45 C46 1.356(7) . ?
C45 C44 1.382(6) . ?
C47 C46 1.377(6) . ?
C15 C16 1.367(7) . ?
C12 C11 1.359(7) . ?
C10 C11 1.389(7) . ?

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
C21 N1 C7 105.3(3) . . ?
C21 N1 C6 127.6(3) . . ?
C7 N1 C6 126.4(3) . . ?
C20 C7 N1 105.9(3) . . ?
C20 C7 C8 123.8(3) . . ?
N1 C7 C8 130.4(4) . . ?
C27 C26 C25 118.0(3) . . ?
C27 C26 C28 121.0(3) . . ?
C25 C26 C28 121.0(3) . . ?
C24 C25 C26 120.9(4) . . ?
C9 C8 C13 119.6(4) . . ?
C9 C8 C7 125.5(4) . . ?
C13 C8 C7 114.7(4) . . ?
C26 C27 C22 121.5(3) . . ?
C5 C6 C1 120.8(4) . . ?
C5 C6 N1 119.3(3) . . ?
C1 C6 N1 119.8(4) . . ?
C7 C20 N2 110.6(3) . . ?
C7 C20 C19 121.9(4) . . ?
N2 C20 C19 127.3(4) . . ?
C24 C23 C22 120.3(3) . . ?
C19 C14 C15 117.5(4) . . ?
C19 C14 C13 120.0(4) . . ?
C15 C14 C13 122.4(4) . . ?
C23 C22 C27 118.9(3) . . ?
C23 C22 C21 118.1(3) . . ?
C27 C22 C21 123.0(3) . . ?
C30 C31 C32 116.2(3) . . ?
C30 C31 C34 117.8(3) . . ?
C32 C31 C34 126.0(4) . . ?
C12 C13 C8 116.8(4) . . ?
C12 C13 C14 121.9(4) . . ?
C8 C13 C14 121.3(3) . . ?
C18 C19 C14 119.8(4) . . ?
C18 C19 C20 122.4(4) . . ?
C14 C19 C20 117.4(4) . . ?
C10 C9 C8 121.6(5) . . ?
C41 C36 C37 117.3(3) . . ?
C41 C36 C35 120.6(3) . . ?
C37 C36 C35 122.0(3) . . ?
C33 C28 C29 117.5(3) . . ?
C33 C28 C26 121.0(3) . . ?
C29 C28 C26 121.5(3) . . ?
C17 C18 C19 121.7(5) . . ?
C21 N2 C20 105.0(3) . . ?
C35 C34 C31 132.3(3) . . ?
C28 C33 C32 122.1(3) . . ?
C34 C35 C36 121.6(3) . . ?
C34 C35 C42 121.7(3) . . ?
C36 C35 C42 116.7(3) . . ?
C18 C17 C16 119.5(5) . . ?
C37 C38 C39 119.8(4) . . ?
C28 C29 C30 120.9(4) . . ?
C33 C32 C31 120.9(4) . . ?
C36 C41 C40 121.6(4) . . ?
C25 C24 C23 120.5(4) . . ?
C2 C1 C6 119.3(4) . . ?
C39 C40 C41 120.4(4) . . ?
C43 C42 C47 117.3(4) . . ?
C43 C42 C35 122.8(3) . . ?
C47 C42 C35 120.0(4) . . ?
C31 C30 C29 122.3(3) . . ?
C3 C4 C5 119.8(5) . . ?
C40 C39 C38 119.6(4) . . ?
C42 C43 C44 122.0(4) . . ?
N2 C21 N1 113.2(3) . . ?
N2 C21 C22 123.1(4) . . ?
N1 C21 C22 123.7(3) . . ?
C3 C2 C1 120.1(5) . . ?
C46 C45 C44 118.8(4) . . ?
C46 C47 C42 119.9(4) . . ?
C6 C5 C4 119.0(5) . . ?
C38 C37 C36 121.3(4) . . ?
C43 C44 C45 119.9(5) . . ?
C16 C15 C14 120.7(5) . . ?
C45 C46 C47 121.9(5) . . ?
C11 C12 C13 121.7(5) . . ?
C15 C16 C17 120.9(5) . . ?
C9 C10 C11 119.1(5) . . ?
C2 C3 C4 121.0(5) . . ?
C12 C11 C10 121.1(5) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
