# 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.
# 
#  For further information on the CCDC, data deposition and
#  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_in3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H30 N O'
_chemical_formula_weight         420.55

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7300(15)
_cell_length_b                   11.040(2)
_cell_length_c                   14.680(3)
_cell_angle_alpha                79.75(3)
_cell_angle_beta                 87.94(3)
_cell_angle_gamma                89.29(3)
_cell_volume                     1231.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             450
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13118
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4253
_reflns_number_gt                3622
_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)+(0.0891P)²+2.6343P] 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_number_reflns         4253
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0730
_refine_ls_wR_factor_ref         0.2338
_refine_ls_wR_factor_gt          0.2305
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_restrained_S_all      1.143
_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
O1 O 0.1311(4) 0.9674(2) 0.88693(17) 0.0372(7) Uani 1 1 d . . .
Q1 H 0.310(6) 0.353(5) 0.383(3) 0.051(13) Uiso 1 1 d . . .
Q2 H 0.114(7) 0.887(5) 0.909(3) 0.060(15) Uiso 1 1 d . . .
C1 C 0.0676(4) 0.9902(3) 0.8010(2) 0.0267(7) Uani 1 1 d . . .
C2 C -0.0063(4) 0.8942(3) 0.7624(2) 0.0233(7) Uani 1 1 d . . .
C3 C -0.0696(4) 0.9259(3) 0.6728(2) 0.0250(7) Uani 1 1 d . . .
H3 H -0.1185 0.8632 0.6452 0.030 Uiso 1 1 calc R . .
C4 C -0.0638(4) 1.0437(3) 0.6235(2) 0.0249(7) Uani 1 1 d . . .
H4 H -0.1085 1.0611 0.5631 0.030 Uiso 1 1 calc R . .
C5 C 0.0086(4) 1.1397(3) 0.6622(2) 0.0237(7) Uani 1 1 d . . .
C6 C 0.0775(4) 1.1090(3) 0.7512(2) 0.0275(7) Uani 1 1 d . . .
H6 H 0.1314 1.1710 0.7775 0.033 Uiso 1 1 calc R . .
C7 C -0.0217(4) 0.7706(3) 0.8136(2) 0.0246(7) Uani 1 1 d . . .
H7 H -0.0696 0.7090 0.7845 0.030 Uiso 1 1 calc R . .
N8 N 0.0275(4) 0.7408(2) 0.89788(19) 0.0256(6) Uani 1 1 d . . .
C9 C 0.0089(4) 0.6195(3) 0.9473(2) 0.0238(7) Uani 1 1 d . . .
C10 C 0.1090(4) 0.5860(3) 1.0248(2) 0.0272(7) Uani 1 1 d . . .
H10 H 0.1834 0.6449 1.0425 0.033 Uiso 1 1 calc R . .
C11 C 0.1020(4) 0.4686(3) 1.0765(2) 0.0269(7) Uani 1 1 d . . .
H11 H 0.1729 0.4474 1.1286 0.032 Uiso 1 1 calc R . .
N12 N 0.0110(4) 1.2581(3) 0.6147(2) 0.0288(7) Uani 1 1 d . . .
C13 C -0.0532(5) 1.2912(3) 0.5211(2) 0.0322(8) Uani 1 1 d . . .
H13A H -0.0272(9) 1.222(2) 0.4864(10) 0.039 Uiso 1 1 calc R . .
H13B H 0.0100(19) 1.366(2) 0.4877(10) 0.039 Uiso 1 1 calc R . .
C14 C -0.2471(5) 1.3175(4) 0.5204(3) 0.0401(9) Uani 1 1 d . . .
H14A H -0.3097 1.2435 0.5502 0.060 Uiso 1 1 calc R . .
H14B H -0.2831 1.3411 0.4563 0.060 Uiso 1 1 calc R . .
H14C H -0.2733 1.3848 0.5542 0.060 Uiso 1 1 calc R . .
C15 C 0.0838(5) 1.3598(3) 0.6527(2) 0.0312(8) Uani 1 1 d . . .
H15A H 0.0619(8) 1.3446(5) 0.7224(19) 0.037 Uiso 1 1 calc R . .
H15B H 0.0226(18) 1.439(2) 0.6257(7) 0.037 Uiso 1 1 calc R . .
C16 C 0.2751(5) 1.3737(4) 0.6316(3) 0.0412(9) Uani 1 1 d . . .
H16A H 0.3355 1.2990 0.6607 0.062 Uiso 1 1 calc R . .
H16B H 0.3175 1.4445 0.6561 0.062 Uiso 1 1 calc R . .
H16C H 0.2971 1.3869 0.5644 0.062 Uiso 1 1 calc R . .
O101 O 0.2653(3) 0.4329(2) 0.35382(17) 0.0331(6) Uani 1 1 d . . .
C101 C 0.3769(4) 0.4708(3) 0.2808(2) 0.0247(7) Uani 1 1 d . . .
C102 C 0.5022(4) 0.3878(3) 0.2547(2) 0.0251(7) Uani 1 1 d . . .
C103 C 0.6111(5) 0.4326(3) 0.1783(2) 0.0324(8) Uani 1 1 d . . .
H103 H 0.6949 0.3785 0.1582 0.039 Uiso 1 1 calc R . .
C104 C 0.6019(5) 0.5512(3) 0.1311(2) 0.0303(8) Uani 1 1 d . . .
H104 H 0.6775 0.5771 0.0790 0.036 Uiso 1 1 calc R . .
C105 C 0.4810(4) 0.6354(3) 0.1593(2) 0.0244(7) Uani 1 1 d . . .
C106 C 0.3660(4) 0.5906(3) 0.2346(2) 0.0253(7) Uani 1 1 d . . .
H106 H 0.2799 0.6440 0.2536 0.030 Uiso 1 1 calc R . .
C107 C 0.5270(4) 0.2667(3) 0.3067(2) 0.0257(7) Uani 1 1 d . . .
H107 H 0.6134 0.2151 0.2859 0.031 Uiso 1 1 calc R . .
N108 N 0.4362(4) 0.2251(2) 0.38092(18) 0.0246(6) Uani 1 1 d . . .
C109 C 0.4721(4) 0.1102(3) 0.4372(2) 0.0221(7) Uani 1 1 d . . .
C110 C 0.3793(4) 0.0827(3) 0.5211(2) 0.0274(7) Uani 1 1 d . . .
H110 H 0.2950 0.1400 0.5361 0.033 Uiso 1 1 calc R . .
C111 C 0.4051(4) -0.0248(3) 0.5832(2) 0.0275(7) Uani 1 1 d . . .
H111 H 0.3392 -0.0405 0.6399 0.033 Uiso 1 1 calc R . .
N112 N 0.4765(4) 0.7551(2) 0.11461(19) 0.0273(6) Uani 1 1 d . . .
C113 C 0.6077(5) 0.8053(3) 0.0440(2) 0.0312(8) Uani 1 1 d . . .
H11A H 0.717(3) 0.7637(13) 0.0588(5) 0.037 Uiso 1 1 calc R . .
H11B H 0.6231(7) 0.892(3) 0.0457(2) 0.037 Uiso 1 1 calc R . .
C114 C 0.5612(5) 0.7916(4) -0.0525(3) 0.0398(9) Uani 1 1 d . . .
H11C H 0.5504 0.7040 -0.0554 0.060 Uiso 1 1 calc R . .
H11D H 0.6522 0.8282 -0.0967 0.060 Uiso 1 1 calc R . .
H11E H 0.4510 0.8336 -0.0679 0.060 Uiso 1 1 calc R . .
C115 C 0.3526(5) 0.8451(3) 0.1415(2) 0.0300(8) Uani 1 1 d . . .
H11F H 0.239(3) 0.8023(12) 0.1626(6) 0.036 Uiso 1 1 calc R . .
H11G H 0.3295(8) 0.9104(18) 0.0855(16) 0.036 Uiso 1 1 calc R . .
C116 C 0.4162(5) 0.9062(3) 0.2180(3) 0.0350(8) Uani 1 1 d . . .
H11H H 0.4252 0.8449 0.2748 0.053 Uiso 1 1 calc R . .
H11I H 0.3346 0.9711 0.2290 0.053 Uiso 1 1 calc R . .
H11J H 0.5303 0.9423 0.1999 0.053 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
O1 C1 1.351(4) . ?
C1 C6 1.384(5) . ?
C1 C2 1.421(5) . ?
C2 C3 1.404(5) . ?
C2 C7 1.440(4) . ?
C3 C4 1.372(4) . ?
C4 C5 1.419(5) . ?
C5 N12 1.368(4) . ?
C5 C6 1.412(5) . ?
C7 N8 1.292(4) . ?
N8 C9 1.411(4) . ?
C9 C10 1.392(5) . ?
C9 C11 1.403(5) 2_567 ?
C10 C11 1.381(5) . ?
C11 C9 1.403(5) 2_567 ?
N12 C13 1.462(4) . ?
N12 C15 1.465(4) . ?
C13 C14 1.523(6) . ?
C15 C16 1.504(5) . ?
O101 C101 1.360(4) . ?
C101 C106 1.379(5) . ?
C101 C102 1.415(5) . ?
C102 C103 1.398(5) . ?
C102 C107 1.431(4) . ?
C103 C104 1.370(5) . ?
C104 C105 1.413(5) . ?
C105 N112 1.367(4) . ?
C105 C106 1.415(4) . ?
C107 N108 1.291(4) . ?
N108 C109 1.415(4) . ?
C109 C110 1.389(5) . ?
C109 C111 1.392(5) 2_656 ?
C110 C111 1.380(5) . ?
C111 C109 1.392(5) 2_656 ?
N112 C113 1.464(4) . ?
N112 C115 1.466(4) . ?
C113 C114 1.508(5) . ?
C115 C116 1.508(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
O1 C1 C6 118.4(3) . . ?
O1 C1 C2 120.7(3) . . ?
C6 C1 C2 120.9(3) . . ?
C3 C2 C1 117.0(3) . . ?
C3 C2 C7 121.0(3) . . ?
C1 C2 C7 122.0(3) . . ?
C4 C3 C2 122.6(3) . . ?
C3 C4 C5 120.3(3) . . ?
N12 C5 C6 121.3(3) . . ?
N12 C5 C4 120.9(3) . . ?
C6 C5 C4 117.9(3) . . ?
C1 C6 C5 121.1(3) . . ?
N8 C7 C2 122.1(3) . . ?
C7 N8 C9 121.2(3) . . ?
C10 C9 C11 118.3(3) . 2_567 ?
C10 C9 N8 117.1(3) . . ?
C11 C9 N8 124.7(3) 2_567 . ?
C11 C10 C9 121.2(3) . . ?
C10 C11 C9 120.5(3) . 2_567 ?
C5 N12 C13 122.2(3) . . ?
C5 N12 C15 122.4(3) . . ?
C13 N12 C15 115.3(3) . . ?
N12 C13 C14 112.6(3) . . ?
N12 C15 C16 112.2(3) . . ?
O101 C101 C106 118.7(3) . . ?
O101 C101 C102 119.8(3) . . ?
C106 C101 C102 121.5(3) . . ?
C103 C102 C101 116.6(3) . . ?
C103 C102 C107 120.7(3) . . ?
C101 C102 C107 122.5(3) . . ?
C104 C103 C102 122.8(3) . . ?
C103 C104 C105 120.6(3) . . ?
N112 C105 C106 122.0(3) . . ?
N112 C105 C104 120.6(3) . . ?
C106 C105 C104 117.4(3) . . ?
C101 C106 C105 121.0(3) . . ?
N108 C107 C102 122.4(3) . . ?
C107 N108 C109 122.2(3) . . ?
C110 C109 C111 117.7(3) . 2_656 ?
C110 C109 N108 116.6(3) . . ?
C111 C109 N108 125.6(3) 2_656 . ?
C111 C110 C109 122.4(3) . . ?
C110 C111 C109 119.9(3) . 2_656 ?
C105 N112 C113 122.1(3) . . ?
C105 N112 C115 122.2(3) . . ?
C113 N112 C115 115.3(3) . . ?
N112 C113 C114 113.1(3) . . ?
N112 C115 C116 112.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.074
_database_code_depnum_ccdc_archive 'CCDC 996876'
