# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_pbcn

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H29 N'
_chemical_formula_weight         391.53

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   11.371(2)
_cell_length_b                   14.464(3)
_cell_length_c                   13.974(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2298.1(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    5551
_cell_measurement_theta_min      2.7050
_cell_measurement_theta_max      26.7298

_exptl_crystal_description       'rod fragment'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_process_details   'REQAB, CrystalClear'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      203(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 AFC8S'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 14.6199
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17811
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2088
_reflns_number_gt                1634
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC, 1999)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 1999)'
_computing_structure_solution    'SHELXTL (Bruker-AXS, 1999)'
_computing_structure_refinement  'SHELXTL (Bruker-AXS, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker-AXS, 1999)'
_computing_publication_material  'SHELXTL (Bruker-AXS, 1999)'

_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)+(0.0942P)²+0.7989P] 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     SHELXL
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2088
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1878
_refine_ls_wR_factor_gt          0.1655
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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 0.5000 0.38686(14) 0.2500 0.0432(6) Uani 1 2 d S . .
C2 C 0.38481(17) 0.37744(13) 0.10664(13) 0.0458(5) Uani 1 1 d . . .
C3 C 0.44091(17) 0.53061(13) 0.18061(14) 0.0490(5) Uani 1 1 d . . .
H3 H 0.3986 0.5618 0.1327 0.059 Uiso 1 1 calc R . .
C1 C 0.44359(16) 0.43446(13) 0.18110(13) 0.0445(5) Uani 1 1 d . . .
C10 C 0.5000 0.58080(19) 0.2500 0.0486(7) Uani 1 2 d S . .
C4 C 0.36828(19) 0.28357(14) 0.12061(15) 0.0530(5) Uani 1 1 d . . .
H4 H 0.3943 0.2563 0.1779 0.064 Uiso 1 1 calc R . .
C11 C 0.5000 0.68391(19) 0.2500 0.0538(7) Uani 1 2 d S . .
C6 C 0.27402(19) 0.26572(16) -0.03259(16) 0.0587(6) Uani 1 1 d . . .
C5 C 0.3141(2) 0.22876(16) 0.05187(15) 0.0585(6) Uani 1 1 d . . .
H5 H 0.3046 0.1652 0.0634 0.070 Uiso 1 1 calc R . .
C7 C 0.2912(2) 0.35959(17) -0.04720(17) 0.0693(7) Uani 1 1 d . . .
H7 H 0.2654 0.3865 -0.1047 0.083 Uiso 1 1 calc R . .
C8 C 0.3451(2) 0.41443(16) 0.02064(16) 0.0621(6) Uani 1 1 d . . .
H8 H 0.3552 0.4779 0.0085 0.075 Uiso 1 1 calc R . .
C12 C 0.5302(2) 0.73400(16) 0.3311(2) 0.0669(7) Uani 1 1 d . . .
H12 H 0.5505 0.7024 0.3875 0.080 Uiso 1 1 calc R . .
C13 C 0.5310(2) 0.82952(17) 0.3303(2) 0.0787(8) Uani 1 1 d . . .
H13 H 0.5533 0.8614 0.3860 0.094 Uiso 1 1 calc R . .
C14 C 0.5000 0.8794(2) 0.2500 0.0798(12) Uani 1 2 d S . .
C9 C 0.2144(3) 0.2068(2) -0.10759(19) 0.0792(8) Uani 1 1 d . . .
H9A H 0.2198 0.1422 -0.0895 0.119 Uiso 1 1 calc R . .
H9B H 0.2527 0.2159 -0.1689 0.119 Uiso 1 1 calc R . .
H9C H 0.1323 0.2244 -0.1126 0.119 Uiso 1 1 calc R . .
C15 C 0.5000 0.9858(2) 0.2500 0.111(2) Uani 1 2 d S . .
C16 C 0.3660(7) 1.0163(5) 0.2299(5) 0.078(2) Uani 0.50 1 d P . .
H16A H 0.3591 1.0829 0.2360 0.117 Uiso 0.50 1 calc PR . .
H16B H 0.3146 0.9865 0.2759 0.117 Uiso 0.50 1 calc PR . .
H16C H 0.3438 0.9978 0.1656 0.117 Uiso 0.50 1 calc PR . .
C17 C 0.5021(7) 1.0216(4) 0.1276(5) 0.100(2) Uani 0.50 1 d P . .
H17A H 0.5127 1.0881 0.1244 0.150 Uiso 0.50 1 calc PR . .
H17B H 0.4283 1.0050 0.0974 0.150 Uiso 0.50 1 calc PR . .
H17C H 0.5664 0.9913 0.0947 0.150 Uiso 0.50 1 calc PR . .
C18 C 0.4150(9) 1.0242(5) 0.2902(10) 0.140(5) Uani 0.50 1 d P . .
H18A H 0.4169 1.0106 0.3581 0.210 Uiso 0.50 1 calc PR . .
H18B H 0.3422 1.0013 0.2629 0.210 Uiso 0.50 1 calc PR . .
H18C H 0.4200 1.0905 0.2807 0.210 Uiso 0.50 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0464(12) 0.0422(11) 0.0411(11) 0.000 0.0006(9) 0.000
C2 0.0464(10) 0.0470(10) 0.0440(10) 0.0006(8) -0.0017(8) 0.0014(8)
C3 0.0490(11) 0.0441(10) 0.0537(11) 0.0053(8) -0.0051(9) 0.0008(8)
C1 0.0446(10) 0.0445(10) 0.0443(10) 0.0029(8) 0.0024(8) 0.0021(7)
C10 0.0430(14) 0.0438(14) 0.0590(16) 0.000 0.0016(12) 0.000
C4 0.0604(12) 0.0499(11) 0.0488(11) 0.0029(9) -0.0056(9) -0.0042(9)
C11 0.0449(15) 0.0400(14) 0.0764(19) 0.000 -0.0016(14) 0.000
C6 0.0521(12) 0.0674(13) 0.0566(12) -0.0097(10) -0.0098(10) -0.0009(10)
C5 0.0635(13) 0.0557(12) 0.0564(13) -0.0036(10) -0.0069(10) -0.0087(10)
C7 0.0813(16) 0.0736(15) 0.0531(13) 0.0021(11) -0.0215(12) 0.0101(12)
C8 0.0774(15) 0.0527(12) 0.0563(13) 0.0031(10) -0.0137(11) 0.0063(10)
C12 0.0666(15) 0.0471(12) 0.0869(17) -0.0055(11) -0.0126(12) -0.0020(10)
C13 0.0707(16) 0.0489(13) 0.116(2) -0.0145(13) -0.0248(15) 0.0009(11)
C14 0.0524(18) 0.0424(16) 0.145(4) 0.000 -0.025(2) 0.000
C9 0.0757(17) 0.0927(19) 0.0691(16) -0.0168(14) -0.0214(13) -0.0035(14)
C15 0.086(3) 0.0376(18) 0.210(6) 0.000 -0.051(4) 0.000
C16 0.099(5) 0.047(3) 0.088(4) -0.005(3) -0.021(3) 0.018(3)
C17 0.121(5) 0.047(3) 0.133(6) 0.024(3) -0.057(5) -0.014(3)
C18 0.123(7) 0.043(3) 0.253(14) 0.002(6) 0.089(9) 0.015(4)

_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 C1 1.346(2) 3_655 ?
N1 C1 1.346(2) . ?
C2 C4 1.385(3) . ?
C2 C8 1.391(3) . ?
C2 C1 1.486(3) . ?
C3 C10 1.385(2) . ?
C3 C1 1.391(3) . ?
C10 C3 1.385(2) 3_655 ?
C10 C11 1.491(4) . ?
C4 C5 1.390(3) . ?
C11 C12 1.389(3) . ?
C11 C12 1.389(3) 3_655 ?
C6 C5 1.373(3) . ?
C6 C7 1.387(3) . ?
C6 C9 1.512(3) . ?
C7 C8 1.380(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.380(3) . ?
C14 C13 1.380(3) 3_655 ?
C14 C15 1.539(5) . ?
C15 C18 1.247(7) 3_655 ?
C15 C18 1.247(7) . ?
C15 C16 1.610(7) 3_655 ?
C15 C16 1.610(7) . ?
C15 C17 1.787(7) 3_655 ?
C15 C17 1.787(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
C1 N1 C1 118.5(2) 3_655 . ?
C4 C2 C8 117.07(19) . . ?
C4 C2 C1 120.43(17) . . ?
C8 C2 C1 122.50(18) . . ?
C10 C3 C1 120.65(19) . . ?
N1 C1 C3 121.68(18) . . ?
N1 C1 C2 115.54(17) . . ?
C3 C1 C2 122.77(17) . . ?
C3 C10 C3 116.8(2) 3_655 . ?
C3 C10 C11 121.61(12) 3_655 . ?
C3 C10 C11 121.61(12) . . ?
C2 C4 C5 121.48(19) . . ?
C12 C11 C12 117.1(3) . 3_655 ?
C12 C11 C10 121.45(14) . . ?
C12 C11 C10 121.45(14) 3_655 . ?
C5 C6 C7 117.5(2) . . ?
C5 C6 C9 121.7(2) . . ?
C7 C6 C9 120.9(2) . . ?
C6 C5 C4 121.3(2) . . ?
C8 C7 C6 121.6(2) . . ?
C7 C8 C2 121.1(2) . . ?
C13 C12 C11 121.1(2) . . ?
C14 C13 C12 121.9(3) . . ?
C13 C14 C13 117.0(3) . 3_655 ?
C13 C14 C15 121.52(15) . . ?
C13 C14 C15 121.52(15) 3_655 . ?
C18 C15 C18 127.2(7) 3_655 . ?
C18 C15 C14 116.4(4) 3_655 . ?
C18 C15 C14 116.4(4) . . ?
C18 C15 C16 39.1(7) 3_655 3_655 ?
C18 C15 C16 122.2(7) . 3_655 ?
C14 C15 C16 105.9(3) . 3_655 ?
C18 C15 C16 122.2(7) 3_655 . ?
C18 C15 C16 39.1(7) . . ?
C14 C15 C16 105.9(3) . . ?
C16 C15 C16 148.2(6) 3_655 . ?
C18 C15 C17 108.2(7) 3_655 3_655 ?
C18 C15 C17 55.3(8) . 3_655 ?
C14 C15 C17 106.9(2) . 3_655 ?
C16 C15 C17 76.5(4) 3_655 3_655 ?
C16 C15 C17 94.3(3) . 3_655 ?
C18 C15 C17 55.3(8) 3_655 . ?
C18 C15 C17 108.2(7) . . ?
C14 C15 C17 106.9(2) . . ?
C16 C15 C17 94.3(3) 3_655 . ?
C16 C15 C17 76.5(4) . . ?
C17 C15 C17 146.3(4) 3_655 . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 989152'
