# Electronic Supplementary Material (ESI) for ChemComm.
# 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_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H28 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         416.54

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.9355(13)
_cell_length_b                   18.231(2)
_cell_length_c                   12.2805(15)
_cell_angle_alpha                90
_cell_angle_beta                 109.896(4)
_cell_angle_gamma                90
_cell_volume                     2302.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6462
_cell_measurement_theta_min      2.2739
_cell_measurement_theta_max      28.2778
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.280
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888

_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            28904
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             5735
_reflns_number_gt                4329
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1322
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_number_reflns         5735
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0628P)²+0.9265P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.82157(14) 0.40740(8) 0.80754(13) 0.0224(3) Uani d . . . 1 . .
H H1 0.7923 0.4567 0.7931 0.027 Uiso calc U . R 1 . .
C C2 0.79135(13) 0.36023(7) 0.71287(12) 0.0174(3) Uani d . . . 1 . .
C C3 0.83619(13) 0.28789(7) 0.73471(11) 0.0167(3) Uani d . . . 1 . .
C C4 0.90676(13) 0.26786(8) 0.84888(12) 0.0197(3) Uani d . . . 1 . .
H H4 0.9384 0.2192 0.8667 0.024 Uiso calc U . R 1 . .
C C5 0.92962(14) 0.31980(9) 0.93527(12) 0.0235(3) Uani d . . . 1 . .
H H5 0.9777 0.3054 1.0123 0.028 Uiso calc U . R 1 . .
C C6 0.71524(13) 0.38683(7) 0.59437(12) 0.0175(3) Uani d . . . 1 . .
C C7 0.57871(14) 0.38668(8) 0.55745(12) 0.0193(3) Uani d . . . 1 . .
C C8 0.50659(15) 0.35682(9) 0.63248(13) 0.0276(3) Uani d . . . 1 . .
H H8A 0.5253 0.3044 0.6459 0.041 Uiso calc U . R 1 . .
H H8B 0.4129 0.3639 0.5936 0.041 Uiso calc U . R 1 . .
H H8C 0.5346 0.3828 0.7068 0.041 Uiso calc U . R 1 . .
C C9 0.50978(14) 0.41292(8) 0.44708(13) 0.0207(3) Uani d . . . 1 . .
H H9 0.4175 0.4146 0.4224 0.025 Uiso calc U . R 1 . .
C C10 0.57205(14) 0.43674(7) 0.37219(12) 0.0199(3) Uani d . . . 1 . .
C C11 0.49309(16) 0.45866(9) 0.25029(13) 0.0267(3) Uani d . . . 1 . .
H H11A 0.4492 0.4154 0.2072 0.04 Uiso calc U . R 1 . .
H H11B 0.5506 0.4797 0.2123 0.04 Uiso calc U . R 1 . .
H H11C 0.428 0.4952 0.2521 0.04 Uiso calc U . R 1 . .
C C12 0.70719(14) 0.43683(8) 0.41066(12) 0.0203(3) Uani d . . . 1 . .
H H12 0.7507 0.4541 0.3606 0.024 Uiso calc U . R 1 . .
C C13 0.78019(14) 0.41210(7) 0.52102(12) 0.0191(3) Uani d . . . 1 . .
C C14 0.92649(14) 0.41046(9) 0.55859(14) 0.0261(3) Uani d . . . 1 . .
H H14A 0.9547 0.4348 0.5 0.039 Uiso calc U . R 1 . .
H H14B 0.9565 0.3594 0.5674 0.039 Uiso calc U . R 1 . .
H H14C 0.9634 0.4361 0.6328 0.039 Uiso calc U . R 1 . .
C C15 0.81074(13) 0.23516(7) 0.64280(12) 0.0173(3) Uani d . . . 1 . .
C C16 0.79176(13) 0.19001(8) 0.56766(11) 0.0172(3) Uani d . . . 1 . .
C C17 0.76442(13) 0.13360(7) 0.48112(11) 0.0155(3) Uani d . . . 1 . .
C C18 0.80377(13) 0.13980(7) 0.38367(11) 0.0159(3) Uani d . . . 1 . .
C C19 0.76814(14) 0.08298(8) 0.30313(12) 0.0203(3) Uani d . . . 1 . .
H H19 0.792 0.0875 0.2359 0.024 Uiso calc U . R 1 . .
C C20 0.66909(14) 0.01732(8) 0.40740(12) 0.0205(3) Uani d . . . 1 . .
H H20 0.6237 -0.0253 0.4168 0.025 Uiso calc U . R 1 . .
C C21 0.69668(13) 0.07085(8) 0.49222(12) 0.0183(3) Uani d . . . 1 . .
H H21 0.6697 0.0649 0.5575 0.022 Uiso calc U . R 1 . .
C C22 0.88200(13) 0.20300(7) 0.36648(11) 0.0161(3) Uani d . . . 1 . .
C C23 0.81991(13) 0.26378(8) 0.30161(12) 0.0187(3) Uani d . . . 1 . .
C C24 0.67399(15) 0.26703(9) 0.25070(15) 0.0295(4) Uani d . . . 1 . .
H H24A 0.6436 0.2342 0.1836 0.044 Uiso calc U . R 1 . .
H H24B 0.6467 0.3174 0.2262 0.044 Uiso calc U . R 1 . .
H H24C 0.6365 0.2516 0.3091 0.044 Uiso calc U . R 1 . .
C C25 0.89527(14) 0.32151(8) 0.28497(13) 0.0221(3) Uani d . . . 1 . .
H H25 0.8533 0.3625 0.24 0.027 Uiso calc U . R 1 . .
C C26 1.03001(14) 0.32060(8) 0.33248(13) 0.0228(3) Uani d . . . 1 . .
C C27 1.10970(17) 0.38433(9) 0.31527(17) 0.0337(4) Uani d . . . 1 . .
H H27A 1.0518 0.4212 0.2657 0.051 Uiso calc U . R 1 . .
H H27B 1.1709 0.3669 0.2784 0.051 Uiso calc U . R 1 . .
H H27C 1.1581 0.4062 0.3905 0.051 Uiso calc U . R 1 . .
C C28 1.08953(14) 0.25964(8) 0.39676(12) 0.0213(3) Uani d . . . 1 . .
H H28 1.1817 0.2584 0.4298 0.026 Uiso calc U . R 1 . .
C C29 1.01823(13) 0.20038(8) 0.41423(11) 0.0182(3) Uani d . . . 1 . .
C C30 1.08662(15) 0.13376(8) 0.47953(13) 0.0237(3) Uani d . . . 1 . .
H H30A 1.0753 0.0926 0.4257 0.036 Uiso calc U . R 1 . .
H H30B 1.0495 0.121 0.5393 0.036 Uiso calc U . R 1 . .
H H30C 1.1795 0.1444 0.516 0.036 Uiso calc U . R 1 . .
N N1 0.88828(12) 0.38910(7) 0.91700(11) 0.0250(3) Uani d . . . 1 . .
N N2 0.70307(13) 0.02256(7) 0.31277(11) 0.0232(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.3353(19) ?
C1 C2 . 1.3924(19) ?
C1 H1 . 0.95 ?
C2 C3 . 1.4007(19) ?
C2 C6 . 1.4905(19) ?
C3 C4 . 1.3994(19) ?
C3 C15 . 1.4359(19) ?
C4 C5 . 1.380(2) ?
C4 H4 . 0.95 ?
C5 N1 . 1.335(2) ?
C5 H5 . 0.95 ?
C6 C13 . 1.401(2) ?
C6 C7 . 1.405(2) ?
C7 C9 . 1.392(2) ?
C7 C8 . 1.504(2) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 C10 . 1.387(2) ?
C9 H9 . 0.95 ?
C10 C12 . 1.390(2) ?
C10 C11 . 1.505(2) ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 C13 . 1.3932(19) ?
C12 H12 . 0.95 ?
C13 C14 . 1.507(2) ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 C16 . 1.2006(19) ?
C16 C17 . 1.4354(19) ?
C17 C21 . 1.3945(19) ?
C17 C18 . 1.4073(18) ?
C18 C19 . 1.3932(19) ?
C18 C22 . 1.4921(19) ?
C19 N2 . 1.3383(19) ?
C19 H19 . 0.95 ?
C20 N2 . 1.3386(19) ?
C20 C21 . 1.384(2) ?
C20 H20 . 0.95 ?
C21 H21 . 0.95 ?
C22 C23 . 1.3984(19) ?
C22 C29 . 1.4039(19) ?
C23 C25 . 1.394(2) ?
C23 C24 . 1.504(2) ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
C25 C26 . 1.388(2) ?
C25 H25 . 0.95 ?
C26 C28 . 1.390(2) ?
C26 C27 . 1.510(2) ?
C27 H27A . 0.98 ?
C27 H27B . 0.98 ?
C27 H27C . 0.98 ?
C28 C29 . 1.391(2) ?
C28 H28 . 0.95 ?
C29 C30 . 1.5065(19) ?
C30 H30A . 0.98 ?
C30 H30B . 0.98 ?
C30 H30C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 125.40(14) ?
N1 C1 H1 . . 117.3 ?
C2 C1 H1 . . 117.3 ?
C1 C2 C3 . . 116.97(13) ?
C1 C2 C6 . . 120.62(12) ?
C3 C2 C6 . . 122.41(12) ?
C4 C3 C2 . . 118.37(12) ?
C4 C3 C15 . . 120.41(13) ?
C2 C3 C15 . . 121.22(12) ?
C5 C4 C3 . . 119.02(13) ?
C5 C4 H4 . . 120.5 ?
C3 C4 H4 . . 120.5 ?
N1 C5 C4 . . 123.91(13) ?
N1 C5 H5 . . 118.0 ?
C4 C5 H5 . . 118.0 ?
C13 C6 C7 . . 120.57(13) ?
C13 C6 C2 . . 119.86(12) ?
C7 C6 C2 . . 119.56(13) ?
C9 C7 C6 . . 118.51(13) ?
C9 C7 C8 . . 119.84(13) ?
C6 C7 C8 . . 121.62(13) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C10 C9 C7 . . 121.84(13) ?
C10 C9 H9 . . 119.1 ?
C7 C9 H9 . . 119.1 ?
C9 C10 C12 . . 118.69(13) ?
C9 C10 C11 . . 119.84(13) ?
C12 C10 C11 . . 121.42(14) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C10 C12 C13 . . 121.41(13) ?
C10 C12 H12 . . 119.3 ?
C13 C12 H12 . . 119.3 ?
C12 C13 C6 . . 118.93(13) ?
C12 C13 C14 . . 120.09(13) ?
C6 C13 C14 . . 120.95(13) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C16 C15 C3 . . 178.43(15) ?
C15 C16 C17 . . 176.53(14) ?
C21 C17 C18 . . 118.38(12) ?
C21 C17 C16 . . 119.94(12) ?
C18 C17 C16 . . 121.68(12) ?
C19 C18 C17 . . 116.84(12) ?
C19 C18 C22 . . 120.59(12) ?
C17 C18 C22 . . 122.56(12) ?
N2 C19 C18 . . 125.30(13) ?
N2 C19 H19 . . 117.4 ?
C18 C19 H19 . . 117.4 ?
N2 C20 C21 . . 123.33(13) ?
N2 C20 H20 . . 118.3 ?
C21 C20 H20 . . 118.3 ?
C20 C21 C17 . . 119.47(13) ?
C20 C21 H21 . . 120.3 ?
C17 C21 H21 . . 120.3 ?
C23 C22 C29 . . 120.36(13) ?
C23 C22 C18 . . 120.12(12) ?
C29 C22 C18 . . 119.51(12) ?
C25 C23 C22 . . 119.02(13) ?
C25 C23 C24 . . 120.39(13) ?
C22 C23 C24 . . 120.59(13) ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C26 C25 C23 . . 121.69(13) ?
C26 C25 H25 . . 119.2 ?
C23 C25 H25 . . 119.2 ?
C25 C26 C28 . . 118.25(13) ?
C25 C26 C27 . . 120.84(14) ?
C28 C26 C27 . . 120.92(14) ?
C26 C27 H27A . . 109.5 ?
C26 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C26 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C26 C28 C29 . . 121.99(13) ?
C26 C28 H28 . . 119.0 ?
C29 C28 H28 . . 119.0 ?
C28 C29 C22 . . 118.69(13) ?
C28 C29 C30 . . 120.36(13) ?
C22 C29 C30 . . 120.91(13) ?
C29 C30 H30A . . 109.5 ?
C29 C30 H30B . . 109.5 ?
H30A C30 H30B . . 109.5 ?
C29 C30 H30C . . 109.5 ?
H30A C30 H30C . . 109.5 ?
H30B C30 H30C . . 109.5 ?
C5 N1 C1 . . 116.32(13) ?
C19 N2 C20 . . 116.65(12) ?

_database_code_depnum_ccdc_archive 'CCDC 1016579'
#######################################################################
#
#                 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_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H34 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         446.61

_chemical_melting_point          ?

_space_group_crystal_system      trigonal
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   23.567(3)
_cell_length_b                   23.567(3)
_cell_length_c                   12.0950(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5817.6(17)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    1014
_cell_measurement_theta_min      2.6114
_cell_measurement_theta_max      22.5031
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2160

_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            9257
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.1030
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3114
_reflns_number_gt                1576
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1762
_refine_ls_R_factor_gt           0.0875
_refine_ls_wR_factor_gt          0.2390
_refine_ls_wR_factor_ref         0.3040
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_number_reflns         3114
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1398P)²+8.5489P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.398
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.34353(19) 0.8687(2) -0.0744(3) 0.0404(10) Uani d . . . 1 . .
H H1A 0.3901 0.8911 -0.0547 0.061 Uiso calc U . R 1 . .
H H1B 0.3359 0.8951 -0.1285 0.061 Uiso calc U . R 1 . .
H H1C 0.3308 0.8258 -0.1066 0.061 Uiso calc U . R 1 . .
C C2 0.23843(18) 0.83939(18) 0.0143(3) 0.0393(10) Uani d . . . 1 . .
H H2 0.219 0.8304 -0.057 0.047 Uiso calc U . R 1 . .
C C3 0.20141(18) 0.83198(18) 0.1030(3) 0.0406(10) Uani d . . . 1 . .
H H3 0.1566 0.819 0.0926 0.049 Uiso calc U . R 1 . .
C C4 0.22721(18) 0.84308(17) 0.2140(3) 0.0361(9) Uani d . . . 1 . .
C C5 0.1886(2) 0.83715(18) 0.3029(4) 0.0454(11) Uani d . . . 1 . .
C C6 0.29582(17) 0.85936(17) 0.2227(3) 0.0320(9) Uani d . . . 1 . .
C C7 0.33051(18) 0.86794(17) 0.1288(3) 0.0327(9) Uani d . . . 1 . .
H H7 0.3754 0.8802 0.1355 0.039 Uiso calc U . R 1 . .
C C8 0.32581(17) 0.86234(17) 0.3322(3) 0.0331(9) Uani d . . . 1 . .
C C9 0.3470(2) 0.91722(19) 0.4014(3) 0.0384(9) Uani d . . . 1 . .
C C10 0.3426(2) 0.9757(2) 0.3638(4) 0.0497(12) Uani d . . . 1 . .
H H10A 0.2987 0.9611 0.3339 0.075 Uiso calc U . R 1 . .
H H10B 0.3754 0.9992 0.3064 0.075 Uiso calc U . R 1 . .
H H10C 0.3506 1.005 0.4268 0.075 Uiso calc U . R 1 . .
C C11 0.3740(2) 0.9176(2) 0.5038(3) 0.0416(10) Uani d . . . 1 . .
H H11 0.3888 0.9551 0.5497 0.05 Uiso calc U . R 1 . .
C C12 0.3804(2) 0.8652(2) 0.5419(3) 0.0417(10) Uani d . . . 1 . .
C C13 0.4106(3) 0.8668(2) 0.6517(3) 0.0552(12) Uani d . . . 1 . .
H H13A 0.3885 0.8228 0.6841 0.083 Uiso calc U . R 1 . .
H H13B 0.4058 0.8971 0.7012 0.083 Uiso calc U . R 1 . .
H H13C 0.4572 0.8816 0.6417 0.083 Uiso calc U . R 1 . .
C C14 0.35841(19) 0.8110(2) 0.4726(3) 0.0388(9) Uani d . . . 1 . .
H H14 0.3617 0.7744 0.4969 0.047 Uiso calc U . R 1 . .
C C15 0.33185(17) 0.80884(18) 0.3694(3) 0.0334(9) Uani d . . . 1 . .
C C16 0.3093(2) 0.74807(19) 0.2990(4) 0.0403(10) Uani d . . . 1 . .
H H16A 0.3446 0.7545 0.2487 0.06 Uiso calc U . R 1 . .
H H16B 0.2708 0.7401 0.2559 0.06 Uiso calc U . R 1 . .
H H16C 0.2978 0.7103 0.3469 0.06 Uiso calc U . R 1 . .
N N1 0.30454(15) 0.85995(15) 0.0243(3) 0.0361(8) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.457(5) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 C3 . 1.338(5) ?
C2 N1 . 1.386(5) ?
C2 H2 . 0.95 ?
C3 C4 . 1.442(6) ?
C3 H3 . 0.95 ?
C4 C5 . 1.371(5) ?
C4 C6 . 1.467(5) ?
C5 C5 16_565 1.207(8) ?
C6 C7 . 1.355(5) ?
C6 C8 . 1.486(5) ?
C7 N1 . 1.376(5) ?
C7 H7 . 0.95 ?
C8 C9 . 1.406(5) ?
C8 C15 . 1.411(5) ?
C9 C11 . 1.392(6) ?
C9 C10 . 1.504(5) ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.394(6) ?
C11 H11 . 0.95 ?
C12 C14 . 1.393(6) ?
C12 C13 . 1.498(6) ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 C15 . 1.386(5) ?
C14 H14 . 0.95 ?
C15 C16 . 1.516(5) ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 N1 . . 121.4(4) ?
C3 C2 H2 . . 119.3 ?
N1 C2 H2 . . 119.3 ?
C2 C3 C4 . . 122.3(4) ?
C2 C3 H3 . . 118.9 ?
C4 C3 H3 . . 118.9 ?
C5 C4 C3 . . 120.9(4) ?
C5 C4 C6 . . 123.9(4) ?
C3 C4 C6 . . 115.1(3) ?
C5 C5 C4 16_565 . 165.8(7) ?
C7 C6 C4 . . 118.8(3) ?
C7 C6 C8 . . 120.2(3) ?
C4 C6 C8 . . 120.9(3) ?
C6 C7 N1 . . 123.8(3) ?
C6 C7 H7 . . 118.1 ?
N1 C7 H7 . . 118.1 ?
C9 C8 C15 . . 118.9(4) ?
C9 C8 C6 . . 121.0(3) ?
C15 C8 C6 . . 120.0(3) ?
C11 C9 C8 . . 119.1(4) ?
C11 C9 C10 . . 120.3(4) ?
C8 C9 C10 . . 120.5(4) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C11 C12 . . 122.7(4) ?
C9 C11 H11 . . 118.6 ?
C12 C11 H11 . . 118.6 ?
C14 C12 C11 . . 117.2(4) ?
C14 C12 C13 . . 120.7(4) ?
C11 C12 C13 . . 122.0(4) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C15 C14 C12 . . 122.0(4) ?
C15 C14 H14 . . 119.0 ?
C12 C14 H14 . . 119.0 ?
C14 C15 C8 . . 120.0(3) ?
C14 C15 C16 . . 118.6(3) ?
C8 C15 C16 . . 121.3(3) ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C7 N1 C2 . . 118.2(3) ?
C7 N1 C1 . . 121.8(3) ?
C2 N1 C1 . . 119.8(3) ?


_database_code_depnum_ccdc_archive 'CCDC 1016580'
#######################################################################
#
#                 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_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H36 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         448.63

_chemical_melting_point          ?

_space_group_crystal_system      trigonal
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   23.7045(15)
_cell_length_b                   23.7045(15)
_cell_length_c                   11.9100(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5795.7(8)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    2471
_cell_measurement_theta_min      2.6196
_cell_measurement_theta_max      25.1007
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.400
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2178

_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            24989
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_av_sigmaI/netI    0.0725
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         30.53
_diffrn_reflns_theta_full        30.53
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             3935
_reflns_number_gt                2369
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1208
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1720
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_number_reflns         3935
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+9.4392P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.355
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.43597(9) 0.07835(9) 0.08896(16) 0.0238(4) Uani d . . . 1 . .
C C2 0.37341(10) 0.01954(10) 0.12563(17) 0.0317(5) Uani d . . . 1 . .
H H2A 0.3546 -0.0108 0.0625 0.048 Uiso calc U . R 1 . .
H H2B 0.3426 0.0332 0.1505 0.048 Uiso calc U . R 1 . .
H H2C 0.3823 -0.002 0.1878 0.048 Uiso calc U . R 1 . .
C C3 0.46342(9) 0.07845(10) -0.01465(16) 0.0273(4) Uani d . . . 1 . .
H H3 0.4416 0.0413 -0.0618 0.033 Uiso calc U . R 1 . .
C C4 0.52158(10) 0.13102(10) -0.05093(15) 0.0274(4) Uani d . . . 1 . .
C C5 0.55123(12) 0.13039(12) -0.16303(17) 0.0410(6) Uani d . . . 1 . .
H H5A 0.5734 0.1745 -0.1947 0.062 Uiso calc U . R 1 . .
H H5B 0.5168 0.1008 -0.2144 0.062 Uiso calc U . R 1 . .
H H5C 0.5827 0.1155 -0.1526 0.062 Uiso calc U . R 1 . .
C C6 0.55268(9) 0.18489(10) 0.01914(15) 0.0253(4) Uani d . . . 1 . .
H H6 0.5928 0.2211 -0.0042 0.03 Uiso calc U . R 1 . .
C C7 0.52663(9) 0.18727(9) 0.12277(15) 0.0212(4) Uani d . . . 1 . .
C C8 0.56251(9) 0.24763(9) 0.19443(17) 0.0281(4) Uani d . . . 1 . .
H H8A 0.531 0.2559 0.2336 0.042 Uiso calc U . R 1 . .
H H8B 0.5904 0.285 0.1466 0.042 Uiso calc U . R 1 . .
H H8C 0.5894 0.2412 0.2496 0.042 Uiso calc U . R 1 . .
C C9 0.46774(8) 0.13334(8) 0.15870(14) 0.0190(4) Uani d . . . 1 . .
C C10 0.43874(8) 0.13717(8) 0.26791(14) 0.0183(4) Uani d . . . 1 . .
C C11 0.46338(9) 0.12929(8) 0.36524(14) 0.0207(4) Uani d . . . 1 . .
H H11 0.4958 0.1169 0.3618 0.025 Uiso calc U . R 1 . .
C C12 0.47070(10) 0.12839(10) 0.57219(15) 0.0277(4) Uani d . . . 1 . .
H H12A 0.4693 0.1561 0.6318 0.041 Uiso calc U . R 1 . .
H H12B 0.516 0.1397 0.559 0.041 Uiso calc U . R 1 . .
H H12C 0.4451 0.0826 0.5949 0.041 Uiso calc U . R 1 . .
C C13 0.39865(9) 0.15878(9) 0.47289(15) 0.0239(4) Uani d . . . 1 . .
H H13 0.3869 0.1684 0.5436 0.029 Uiso calc U . R 1 . .
C C14 0.37068(9) 0.16555(9) 0.37951(16) 0.0232(4) Uani d . . . 1 . .
H H14 0.339 0.1787 0.3869 0.028 Uiso calc U . R 1 . .
C C15 0.38704(8) 0.15363(8) 0.26814(15) 0.0191(4) Uani d . . . 1 . .
C C16 0.35839(8) 0.15896(8) 0.17114(16) 0.0218(4) Uani d . . . 1 . .
H H16 0.3741 0.1514 0.1027 0.026 Uiso calc U . R 1 . .
N N1 0.44357(8) 0.13842(8) 0.46950(12) 0.0235(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C3 . 1.394(3) ?
C1 C9 . 1.405(2) ?
C1 C2 . 1.505(3) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C3 C4 . 1.386(3) ?
C3 H3 . 0.95 ?
C4 C6 . 1.389(3) ?
C4 C5 . 1.512(3) ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 C7 . 1.394(2) ?
C6 H6 . 0.95 ?
C7 C9 . 1.408(2) ?
C7 C8 . 1.511(3) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 C10 . 1.495(2) ?
C10 C11 . 1.352(2) ?
C10 C15 . 1.460(2) ?
C11 N1 . 1.382(2) ?
C11 H11 . 0.95 ?
C12 N1 . 1.456(2) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C14 . 1.345(3) ?
C13 N1 . 1.372(2) ?
C13 H13 . 0.95 ?
C14 C15 . 1.449(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.378(2) ?
C16 C16 13 1.411(3) ?
C16 H16 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 C1 C9 . . 119.22(17) ?
C3 C1 C2 . . 120.08(17) ?
C9 C1 C2 . . 120.69(17) ?
C1 C2 H2A . . 109.5 ?
C1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C4 C3 C1 . . 122.06(18) ?
C4 C3 H3 . . 119.0 ?
C1 C3 H3 . . 119.0 ?
C3 C4 C6 . . 118.12(17) ?
C3 C4 C5 . . 121.63(19) ?
C6 C4 C5 . . 120.26(19) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C4 C6 C7 . . 121.81(18) ?
C4 C6 H6 . . 119.1 ?
C7 C6 H6 . . 119.1 ?
C6 C7 C9 . . 119.38(17) ?
C6 C7 C8 . . 119.18(17) ?
C9 C7 C8 . . 121.43(16) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C1 C9 C7 . . 119.40(16) ?
C1 C9 C10 . . 121.41(16) ?
C7 C9 C10 . . 119.12(15) ?
C11 C10 C15 . . 120.90(16) ?
C11 C10 C9 . . 119.60(15) ?
C15 C10 C9 . . 119.38(15) ?
C10 C11 N1 . . 122.99(16) ?
C10 C11 H11 . . 118.5 ?
N1 C11 H11 . . 118.5 ?
N1 C12 H12A . . 109.5 ?
N1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 N1 . . 122.24(17) ?
C14 C13 H13 . . 118.9 ?
N1 C13 H13 . . 118.9 ?
C13 C14 C15 . . 122.52(17) ?
C13 C14 H14 . . 118.7 ?
C15 C14 H14 . . 118.7 ?
C16 C15 C14 . . 123.88(16) ?
C16 C15 C10 . . 122.76(16) ?
C14 C15 C10 . . 113.34(15) ?
C15 C16 C16 . 13 127.2(2) ?
C15 C16 H16 . . 116.4 ?
C16 C16 H16 13 . 116.4 ?
C13 N1 C11 . . 117.75(15) ?
C13 N1 C12 . . 121.11(15) ?
C11 N1 C12 . . 121.13(15) ?

_database_code_depnum_ccdc_archive 'CCDC 1016581'
