# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_y-3-2
_database_code_depnum_ccdc_archive 'CCDC 1555726'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-11-20 downloaded from the CCDC.
;
_audit_creation_date             2017-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H36 N2'
_chemical_formula_sum            'C44 H36 N2'
_chemical_formula_weight         592.75
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3224(7)
_cell_length_b                   21.5654(17)
_cell_length_c                   8.0810(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.337(6)
_cell_angle_gamma                90
_cell_volume                     1598.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3969
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.4610
_cell_measurement_theta_min      4.0680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.11a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_description       stick
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8858
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.076
_diffrn_reflns_theta_max         67.076
_diffrn_reflns_theta_min         4.100
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  27.00   0.50    0.50    --    5.00  38.00  60.00   72
  2  ω     53.00  94.00   0.50    0.50    --    5.00  38.00  60.00   82
  3  ω    -59.00  -9.00   0.50    0.50    --  -45.20  72.00   0.00  100
  4  ω    -76.00 -46.00   0.50    0.50    -- -100.10  72.00   0.00   60
  5  ω    -91.00 -11.00   0.50    0.50    -- -100.10  57.00  90.00  160
  6  ω    -93.00 -68.00   0.50    0.50    -- -100.10  72.00 120.00   50
  7  ω   -110.00 -81.00   0.50    0.50    -- -100.10  72.00   0.00   58
  8  ω   -105.00 -11.00   0.50    0.50    -- -100.10  72.00  30.00  188
  9  ω   -105.00 -79.00   0.50    0.50    -- -100.10  72.00  60.00   52
 10  ω    -97.00 -11.00   0.50    0.50    -- -100.10  72.00  90.00  172
 11  ω   -115.00 -65.00   0.50    0.50    --  -45.20 -38.00  60.00  100
 12  ω    -69.00 -38.00   0.50    0.50    --  -45.20 -72.00 -30.00   62
 13  ω   -112.00 -11.00   0.50    0.50    -- -100.10  19.00 -90.00  202
 14  ω   -114.00 -65.00   0.50    0.50    -- -100.10  57.00   0.00   98
 15  ω   -109.00 -13.00   0.50    0.50    -- -100.10  19.00  30.00  192
 16  ω   -121.00 -90.00   0.50    0.50    -- -100.10 -57.00-120.00   62
 17  ω   -135.00 -88.00   0.50    0.50    --  -45.20 -72.00 -30.00   94
 18  ω   -172.00-133.00   0.50    0.50    -- -100.10 -57.00-120.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0454785000
_diffrn_orient_matrix_UB_12      -0.0680388000
_diffrn_orient_matrix_UB_13      0.0312097000
_diffrn_orient_matrix_UB_21      0.1613457000
_diffrn_orient_matrix_UB_22      0.0202214000
_diffrn_orient_matrix_UB_23      0.0390820000
_diffrn_orient_matrix_UB_31      -0.0098879000
_diffrn_orient_matrix_UB_32      0.0071692000
_diffrn_orient_matrix_UB_33      0.1872434000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2460
_reflns_number_total             2813
_reflns_odcompleteness_completeness 98.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.11a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.11a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.11a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2813
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.4962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1152
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C003(H003), C007(H007), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L)
2.b Idealised Me refined as rotating group:
 C00M(H00A,H00G,H00M), C00N(H00N,H00O,H00P)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N001 N 0.64541(13) 0.39601(6) 0.52742(14) 0.0322(3) Uani 1 1 d . . . . .
C002 C 0.72556(15) 0.42138(7) 0.40608(17) 0.0313(3) Uani 1 1 d . . . . .
C003 C 0.75797(16) 0.38408(7) 0.27812(18) 0.0334(3) Uani 1 1 d . . . . .
H003 H 0.7266 0.3431 0.2698 0.040 Uiso 1 1 calc R . . . .
C004 C 0.72484(16) 0.35837(7) 0.65584(17) 0.0307(3) Uani 1 1 d . . . . .
C005 C 0.88512(15) 0.46903(7) 0.17496(18) 0.0337(3) Uani 1 1 d . . . . .
C006 C 0.49494(16) 0.38429(7) 0.47463(18) 0.0330(3) Uani 1 1 d . . . . .
C007 C 0.83668(16) 0.40758(7) 0.16280(18) 0.0355(4) Uani 1 1 d . . . . .
H007 H 0.8575 0.3824 0.0767 0.043 Uiso 1 1 calc R . . . .
C008 C 0.64984(17) 0.32746(7) 0.76799(18) 0.0336(3) Uani 1 1 d . . . . .
C009 C 0.41691(17) 0.35464(7) 0.58536(19) 0.0368(4) Uani 1 1 d . . . . .
C00A C 0.96661(16) 0.49195(7) 0.05340(19) 0.0373(4) Uani 1 1 d . . . . .
C00B C 0.42232(17) 0.40209(8) 0.31469(18) 0.0381(4) Uani 1 1 d . . . . .
H00B H 0.4723 0.4238 0.2433 0.046 Uiso 1 1 calc R . . . .
C00C C 0.87518(17) 0.35156(8) 0.67273(18) 0.0370(4) Uani 1 1 d . . . . .
H00C H 0.9258 0.3739 0.6032 0.044 Uiso 1 1 calc R . . . .
C00D C 0.85284(17) 0.50577(7) 0.3052(2) 0.0391(4) Uani 1 1 d . . . . .
H00D H 0.8853 0.5466 0.3151 0.047 Uiso 1 1 calc R . . . .
C00E C 0.77316(17) 0.48247(7) 0.42026(19) 0.0371(4) Uani 1 1 d . . . . .
H00E H 0.7517 0.5075 0.5063 0.044 Uiso 1 1 calc R . . . .
C00F C 0.72701(19) 0.28618(7) 0.88229(19) 0.0404(4) Uani 1 1 d . . . . .
H00F H 0.6775 0.2636 0.9525 0.048 Uiso 1 1 calc R . . . .
C00G C 0.49249(17) 0.34586(8) 0.76786(19) 0.0417(4) Uani 1 1 d . . . . .
C00H C 0.95005(19) 0.31156(8) 0.7930(2) 0.0443(4) Uani 1 1 d . . . . .
H00H H 1.0507 0.3078 0.8047 0.053 Uiso 1 1 calc R . . . .
C00I C 0.27159(17) 0.33949(8) 0.5268(2) 0.0444(4) Uani 1 1 d . . . . .
H00I H 0.2202 0.3182 0.5974 0.053 Uiso 1 1 calc R . . . .
C00J C 0.27657(18) 0.38764(9) 0.2621(2) 0.0456(4) Uani 1 1 d . . . . .
H00J H 0.2292 0.3998 0.1559 0.055 Uiso 1 1 calc R . . . .
C00K C 0.87610(19) 0.27759(8) 0.8948(2) 0.0441(4) Uani 1 1 d . . . . .
H00K H 0.9254 0.2492 0.9711 0.053 Uiso 1 1 calc R . . . .
C00L C 0.20122(18) 0.35525(9) 0.3665(2) 0.0481(4) Uani 1 1 d . . . . .
H00L H 0.1044 0.3442 0.3297 0.058 Uiso 1 1 calc R . . . .
C00M C 0.4938(2) 0.40983(10) 0.8552(2) 0.0520(5) Uani 1 1 d . . . . .
H00A H 0.5451 0.4066 0.9690 0.078 Uiso 1 1 calc GR . . . .
H00G H 0.3954 0.4230 0.8552 0.078 Uiso 1 1 calc GR . . . .
H00M H 0.5417 0.4396 0.7956 0.078 Uiso 1 1 calc GR . . . .
C00N C 0.4137(2) 0.29915(12) 0.8626(2) 0.0685(6) Uani 1 1 d . . . . .
H00N H 0.4096 0.2597 0.8072 0.103 Uiso 1 1 calc GR . . . .
H00O H 0.3165 0.3135 0.8642 0.103 Uiso 1 1 calc GR . . . .
H00P H 0.4657 0.2950 0.9759 0.103 Uiso 1 1 calc GR . . . .


_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
N001 C002 1.4429(17) . ?
N001 C004 1.4172(18) . ?
N001 C006 1.4138(19) . ?
C002 C003 1.386(2) . ?
C002 C00E 1.388(2) . ?
C003 H003 0.9300 . ?
C003 C007 1.382(2) . ?
C004 C008 1.408(2) . ?
C004 C00C 1.391(2) . ?
C005 C007 1.398(2) . ?
C005 C00A 1.433(2) . ?
C005 C00D 1.393(2) . ?
C006 C009 1.404(2) . ?
C006 C00B 1.401(2) . ?
C007 H007 0.9300 . ?
C008 C00F 1.387(2) . ?
C008 C00G 1.519(2) . ?
C009 C00G 1.528(2) . ?
C009 C00I 1.391(2) . ?
C00A C00A 1.202(3) 3_765 ?
C00B H00B 0.9300 . ?
C00B C00J 1.384(2) . ?
C00C H00C 0.9300 . ?
C00C C00H 1.390(2) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.384(2) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00K 1.388(2) . ?
C00G C00M 1.549(3) . ?
C00G C00N 1.530(2) . ?
C00H H00H 0.9300 . ?
C00H C00K 1.376(2) . ?
C00I H00I 0.9300 . ?
C00I C00L 1.385(2) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.380(2) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00A 0.9600 . ?
C00M H00G 0.9600 . ?
C00M H00M 0.9600 . ?
C00N H00N 0.9600 . ?
C00N H00O 0.9600 . ?
C00N H00P 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
C004 N001 C002 116.65(11) . . ?
C006 N001 C002 118.00(11) . . ?
C006 N001 C004 118.57(12) . . ?
C003 C002 N001 119.73(13) . . ?
C003 C002 C00E 120.21(13) . . ?
C00E C002 N001 120.04(13) . . ?
C002 C003 H003 119.9 . . ?
C007 C003 C002 120.25(14) . . ?
C007 C003 H003 119.9 . . ?
C008 C004 N001 119.21(13) . . ?
C00C C004 N001 121.14(13) . . ?
C00C C004 C008 119.65(13) . . ?
C007 C005 C00A 118.88(14) . . ?
C00D C005 C007 118.78(13) . . ?
C00D C005 C00A 122.34(14) . . ?
C009 C006 N001 119.24(13) . . ?
C00B C006 N001 121.23(13) . . ?
C00B C006 C009 119.53(14) . . ?
C003 C007 C005 120.28(14) . . ?
C003 C007 H007 119.9 . . ?
C005 C007 H007 119.9 . . ?
C004 C008 C00G 117.83(13) . . ?
C00F C008 C004 118.32(14) . . ?
C00F C008 C00G 123.59(14) . . ?
C006 C009 C00G 118.00(13) . . ?
C00I C009 C006 118.31(14) . . ?
C00I C009 C00G 123.47(14) . . ?
C00A C00A C005 176.3(2) 3_765 . ?
C006 C00B H00B 119.8 . . ?
C00J C00B C006 120.44(14) . . ?
C00J C00B H00B 119.8 . . ?
C004 C00C H00C 119.8 . . ?
C00H C00C C004 120.31(14) . . ?
C00H C00C H00C 119.8 . . ?
C005 C00D H00D 119.5 . . ?
C00E C00D C005 121.05(14) . . ?
C00E C00D H00D 119.5 . . ?
C002 C00E H00E 120.3 . . ?
C00D C00E C002 119.42(14) . . ?
C00D C00E H00E 120.3 . . ?
C008 C00F H00F 119.1 . . ?
C008 C00F C00K 121.81(15) . . ?
C00K C00F H00F 119.1 . . ?
C008 C00G C009 108.12(12) . . ?
C008 C00G C00M 107.68(13) . . ?
C008 C00G C00N 112.19(15) . . ?
C009 C00G C00M 107.11(13) . . ?
C009 C00G C00N 112.64(14) . . ?
C00N C00G C00M 108.87(15) . . ?
C00C C00H H00H 119.8 . . ?
C00K C00H C00C 120.39(16) . . ?
C00K C00H H00H 119.8 . . ?
C009 C00I H00I 119.0 . . ?
C00L C00I C009 121.96(15) . . ?
C00L C00I H00I 119.0 . . ?
C00B C00J H00J 119.8 . . ?
C00L C00J C00B 120.36(15) . . ?
C00L C00J H00J 119.8 . . ?
C00F C00K H00K 120.4 . . ?
C00H C00K C00F 119.22(15) . . ?
C00H C00K H00K 120.4 . . ?
C00I C00L H00L 120.4 . . ?
C00J C00L C00I 119.22(15) . . ?
C00J C00L H00L 120.4 . . ?
C00G C00M H00A 109.5 . . ?
C00G C00M H00G 109.5 . . ?
C00G C00M H00M 109.5 . . ?
H00A C00M H00G 109.5 . . ?
H00A C00M H00M 109.5 . . ?
H00G C00M H00M 109.5 . . ?
C00G C00N H00N 109.5 . . ?
C00G C00N H00O 109.5 . . ?
C00G C00N H00P 109.5 . . ?
H00N C00N H00O 109.5 . . ?
H00N C00N H00P 109.5 . . ?
H00O C00N H00P 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.486
