# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_bwn16207a
_database_code_depnum_ccdc_archive 'CCDC 1560810'
_audit_update_record             
;
2017-07-07 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;
_audit_creation_date             2016-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C46 H36 N2'
_chemical_formula_sum            'C46 H36 N2'
_chemical_formula_weight         616.77
_chemical_melting_point          ?
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.360(2)
_cell_length_b                   14.549(3)
_cell_length_c                   10.388(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.46(3)
_cell_angle_gamma                90.00
_cell_volume                     1669.8(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5305
_cell_measurement_temperature    153.1500
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      1.3997
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9022
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11048
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.34
_diffrn_ambient_temperature      153.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.8438
	          2theta: -20.1752
scan:
	Number of images: 240
	           Slice: -80.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.8438
	          2theta: -20.1752
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             3934
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0247
_diffrn_orient_matrix_UB_12      0.0947
_diffrn_orient_matrix_UB_13      0.0147
_diffrn_orient_matrix_UB_21      -0.0017
_diffrn_orient_matrix_UB_22      -0.0101
_diffrn_orient_matrix_UB_23      0.0680
_diffrn_orient_matrix_UB_31      0.0905
_diffrn_orient_matrix_UB_32      -0.0019
_diffrn_orient_matrix_UB_33      0.0020
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           90.0000
_diffrn_source_power             4.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3447
_reflns_number_total             3772
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0692
_refine_ls_restrained_S_all      1.206
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0227P)²+0.9915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1284
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.06164(14) 0.14953(11) 0.67599(15) 0.0266(3) Uani 1 d . . .
C1 C -0.22886(16) 0.27554(13) 0.67398(18) 0.0255(4) Uani 1 d . . .
C2 C -0.22503(18) 0.34750(14) 0.58583(19) 0.0309(4) Uani 1 d . . .
H2 H -0.1668 0.3461 0.5334 0.037 Uiso 1 calc . . R
C3 C -0.30470(19) 0.42092(15) 0.5735(2) 0.0372(5) Uani 1 d . . .
H3 H -0.2995 0.4698 0.5144 0.045 Uiso 1 calc . . R
C4 C -0.39172(19) 0.42324(15) 0.6469(2) 0.0379(5) Uani 1 d . . .
H4 H -0.4469 0.4732 0.6379 0.045 Uiso 1 calc . . R
C5 C -0.39784(19) 0.35220(15) 0.7337(2) 0.0361(5) Uani 1 d . . .
H5 H -0.4573 0.3536 0.7846 0.043 Uiso 1 calc . . R
C6 C -0.31775(17) 0.27891(14) 0.74698(19) 0.0306(4) Uani 1 d . . .
H6 H -0.3234 0.2304 0.8064 0.037 Uiso 1 calc . . R
C7 C -0.14174(17) 0.19787(13) 0.69030(18) 0.0260(4) Uani 1 d . . .
C8 C -0.18639(17) 0.10355(13) 0.70802(18) 0.0262(4) Uani 1 d . . .
C9 C -0.12171(19) 0.04565(14) 0.80614(19) 0.0320(4) Uani 1 d . . .
H9 H -0.0469 0.0660 0.8602 0.038 Uiso 1 calc . . R
C10 C -0.1647(2) -0.04129(15) 0.8264(2) 0.0392(5) Uani 1 d . . .
H10 H -0.1199 -0.0793 0.8949 0.047 Uiso 1 calc . . R
C11 C -0.2723(2) -0.07274(15) 0.7473(2) 0.0415(5) Uani 1 d . . .
H11 H -0.3016 -0.1323 0.7609 0.050 Uiso 1 calc . . R
C12 C -0.3370(2) -0.01653(16) 0.6483(2) 0.0426(5) Uani 1 d . . .
H12 H -0.4106 -0.0379 0.5930 0.051 Uiso 1 calc . . R
C13 C -0.29493(19) 0.07097(15) 0.6292(2) 0.0352(5) Uani 1 d . . .
H13 H -0.3407 0.1091 0.5615 0.042 Uiso 1 calc . . R
C14 C -0.02486(17) 0.21529(13) 0.68891(18) 0.0274(4) Uani 1 d . . .
H14 H 0.0006 0.2776 0.6975 0.033 Uiso 1 calc . . R
C15 C 0.03029(16) 0.07393(13) 0.58666(17) 0.0247(4) Uani 1 d . . .
C16 C -0.04453(17) 0.08715(14) 0.46160(18) 0.0272(4) Uani 1 d . . .
H16 H -0.0753 0.1467 0.4352 0.033 Uiso 1 calc . . R
C17 C -0.07423(17) 0.01367(13) 0.37556(18) 0.0271(4) Uani 1 d . . .
H17 H -0.1250 0.0231 0.2900 0.033 Uiso 1 calc . . R
C18 C 0.18330(17) 0.16200(13) 0.74539(18) 0.0251(4) Uani 1 d . . .
C19 C 0.20973(18) 0.20076(14) 0.87137(18) 0.0307(4) Uani 1 d . . .
H19 H 0.1460 0.2184 0.9113 0.037 Uiso 1 calc . . R
C20 C 0.32941(19) 0.21363(15) 0.93870(19) 0.0356(5) Uani 1 d . . .
H20 H 0.3468 0.2393 1.0252 0.043 Uiso 1 calc . . R
C21 C 0.42333(19) 0.18965(14) 0.8817(2) 0.0343(5) Uani 1 d . . .
H21 H 0.5049 0.1994 0.9278 0.041 Uiso 1 calc . . R
C22 C 0.39712(18) 0.15119(15) 0.7565(2) 0.0339(5) Uani 1 d . . .
H22 H 0.4613 0.1346 0.7166 0.041 Uiso 1 calc . . R
C23 C 0.27853(18) 0.13658(14) 0.68846(19) 0.0294(4) Uani 1 d . . .
H23 H 0.2618 0.1093 0.6031 0.035 Uiso 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 C14 1.400(2) . ?
N1 C15 1.430(2) . ?
N1 C18 1.414(2) . ?
C1 C2 1.398(3) . ?
C1 C6 1.398(3) . ?
C1 C7 1.486(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.489(3) . ?
C7 C14 1.355(3) . ?
C8 C9 1.393(3) . ?
C8 C13 1.395(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.390(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.390(2) . ?
C15 C17 1.392(3) 3_556 ?
C16 H16 0.9500 . ?
C16 C17 1.384(3) . ?
C17 C15 1.392(3) 3_556 ?
C17 H17 0.9500 . ?
C18 C19 1.392(3) . ?
C18 C23 1.398(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.389(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(3) . ?
C23 H23 0.9500 . ?

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 N1 C15 120.90(15) . . ?
C14 N1 C18 119.21(15) . . ?
C18 N1 C15 119.74(15) . . ?
C2 C1 C7 121.52(17) . . ?
C6 C1 C2 117.75(18) . . ?
C6 C1 C7 120.73(17) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.21(19) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.5(2) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.9(2) . . ?
C5 C6 H6 119.6 . . ?
C1 C7 C8 118.55(16) . . ?
C14 C7 C1 119.01(17) . . ?
C14 C7 C8 122.44(17) . . ?
C9 C8 C7 120.73(17) . . ?
C9 C8 C13 117.89(18) . . ?
C13 C8 C7 121.37(17) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.3(2) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 120.9(2) . . ?
C12 C13 H13 119.5 . . ?
N1 C14 H14 117.1 . . ?
C7 C14 N1 125.77(18) . . ?
C7 C14 H14 117.1 . . ?
C16 C15 N1 120.39(17) . . ?
C16 C15 C17 119.43(17) . 3_556 ?
C17 C15 N1 120.18(16) 3_556 . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.06(18) . . ?
C17 C16 H16 120.0 . . ?
C15 C17 H17 119.7 3_556 . ?
C16 C17 C15 120.52(17) . 3_556 ?
C16 C17 H17 119.7 . . ?
C19 C18 N1 120.18(17) . . ?
C19 C18 C23 119.08(18) . . ?
C23 C18 N1 120.74(17) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 119.97(19) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.90(19) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.16(19) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.85(19) . . ?
C23 C22 H22 119.6 . . ?
C18 C23 H23 120.0 . . ?
C22 C23 C18 120.04(18) . . ?
C22 C23 H23 120.0 . . ?

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
N1 C15 C16 C17 179.84(17) . . . . ?
N1 C18 C19 C20 -179.43(18) . . . . ?
N1 C18 C23 C22 178.51(18) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C1 C7 C8 C9 -133.87(19) . . . . ?
C1 C7 C8 C13 44.8(3) . . . . ?
C1 C7 C14 N1 -166.21(17) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C7 C8 -141.30(18) . . . . ?
C2 C1 C7 C14 38.9(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C6 C1 C2 C3 1.6(3) . . . . ?
C6 C1 C7 C8 38.7(2) . . . . ?
C6 C1 C7 C14 -141.08(19) . . . . ?
C7 C1 C2 C3 -178.38(18) . . . . ?
C7 C1 C6 C5 178.83(18) . . . . ?
C7 C8 C9 C10 177.80(18) . . . . ?
C7 C8 C13 C12 -178.71(19) . . . . ?
C8 C7 C14 N1 14.0(3) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C8 C13 C12 0.0(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C8 0.8(3) . . . . ?
C13 C8 C9 C10 -1.0(3) . . . . ?
C14 N1 C15 C16 41.4(3) . . . . ?
C14 N1 C15 C17 -138.36(18) . . . 3_556 ?
C14 N1 C18 C19 36.1(3) . . . . ?
C14 N1 C18 C23 -143.28(19) . . . . ?
C14 C7 C8 C9 45.9(3) . . . . ?
C14 C7 C8 C13 -135.3(2) . . . . ?
C15 N1 C14 C7 39.9(3) . . . . ?
C15 N1 C18 C19 -148.37(18) . . . . ?
C15 N1 C18 C23 32.2(3) . . . . ?
C15 C16 C17 C15 0.3(3) . . . 3_556 ?
C17 C15 C16 C17 -0.3(3) 3_556 . . . ?
C18 N1 C14 C7 -144.60(19) . . . . ?
C18 N1 C15 C16 -133.99(19) . . . . ?
C18 N1 C15 C17 46.2(2) . . . 3_556 ?
C18 C19 C20 C21 0.9(3) . . . . ?
C19 C18 C23 C22 -0.9(3) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C21 C22 C23 C18 1.0(3) . . . . ?
C23 C18 C19 C20 0.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
