# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# 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_tbt2et

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H27 N5 O2'
_chemical_formula_sum            'C13 H27 N5 O2'
_chemical_formula_weight         285.40

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           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   12.6187(2)
_cell_length_b                   15.3717(3)
_cell_length_c                   15.8322(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3070.99(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    110
_cell_measurement_reflns_used    7867
_cell_measurement_theta_min      2.8885
_cell_measurement_theta_max      28.5725

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_min  0.88116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110
_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  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  25
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15851
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3001
_reflns_number_gt                2315
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.64 (release 22-03-2010 CrysAlis171 .NET)
(compiled Mar 22 2010,13:57:49)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_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)+(0.0881P)²+0.2462P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3001
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1382
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
C1 C 0.82099(13) -0.15396(11) 0.04807(10) 0.0190(4) Uani 1 1 d . . .
C2 C 0.73594(13) -0.00581(10) 0.04487(10) 0.0171(4) Uani 1 1 d . . .
C3 C 0.89505(13) -0.03713(11) 0.13571(10) 0.0194(4) Uani 1 1 d . . .
C4 C 0.95361(14) -0.18774(12) 0.15629(11) 0.0244(4) Uani 1 1 d . . .
H4A H 1.0185 -0.1604 0.1756 0.029 Uiso 1 1 calc R . .
H4B H 0.9727 -0.2348 0.1185 0.029 Uiso 1 1 calc R . .
C5 C 0.89422(17) -0.22429(13) 0.23143(12) 0.0315(5) Uani 1 1 d . . .
H5A H 0.9381 -0.2659 0.2601 0.047 Uiso 1 1 calc R . .
H5B H 0.8305 -0.2523 0.2124 0.047 Uiso 1 1 calc R . .
H5C H 0.8764 -0.1779 0.2695 0.047 Uiso 1 1 calc R . .
C6 C 0.85061(13) 0.11340(11) 0.11397(11) 0.0210(4) Uani 1 1 d . . .
H6A H 0.8443 0.1204 0.1747 0.025 Uiso 1 1 calc R . .
H6B H 0.7955 0.1481 0.0877 0.025 Uiso 1 1 calc R . .
C7 C 0.95838(14) 0.14745(12) 0.08573(12) 0.0282(4) Uani 1 1 d . . .
H7A H 0.9653 0.2074 0.1017 0.042 Uiso 1 1 calc R . .
H7B H 0.9644 0.1423 0.0255 0.042 Uiso 1 1 calc R . .
H7C H 1.0134 0.1141 0.1122 0.042 Uiso 1 1 calc R . .
C8 C 0.80656(14) 0.06840(12) -0.08087(11) 0.0251(4) Uani 1 1 d . . .
H8A H 0.7875 0.1121 -0.1214 0.038 Uiso 0.50 1 calc PR . .
H8B H 0.8192 0.0143 -0.1094 0.038 Uiso 0.50 1 calc PR . .
H8C H 0.8697 0.0860 -0.0516 0.038 Uiso 0.50 1 calc PR . .
H8D H 0.8634 0.0295 -0.0669 0.038 Uiso 0.50 1 calc PR . .
H8E H 0.8317 0.1273 -0.0789 0.038 Uiso 0.50 1 calc PR . .
H8F H 0.7812 0.0556 -0.1367 0.038 Uiso 0.50 1 calc PR . .
C9 C 0.61757(14) 0.07577(12) -0.05784(11) 0.0249(4) Uani 1 1 d . . .
H9A H 0.6249 0.1199 -0.1003 0.037 Uiso 0.50 1 calc PR . .
H9B H 0.5699 0.0957 -0.0147 0.037 Uiso 0.50 1 calc PR . .
H9C H 0.5899 0.0237 -0.0831 0.037 Uiso 0.50 1 calc PR . .
H9D H 0.5649 0.0396 -0.0318 0.037 Uiso 0.50 1 calc PR . .
H9E H 0.6199 0.0639 -0.1173 0.037 Uiso 0.50 1 calc PR . .
H9F H 0.5999 0.1358 -0.0490 0.037 Uiso 0.50 1 calc PR . .
C10 C 0.61234(14) 0.07082(11) 0.14033(11) 0.0238(4) Uani 1 1 d . . .
H10A H 0.6126 0.1177 0.1003 0.036 Uiso 0.50 1 calc PR . .
H10B H 0.6630 0.0825 0.1841 0.036 Uiso 0.50 1 calc PR . .
H10C H 0.5430 0.0654 0.1647 0.036 Uiso 0.50 1 calc PR . .
H10D H 0.5998 0.0594 0.1991 0.036 Uiso 0.50 1 calc PR . .
H10E H 0.5494 0.0946 0.1153 0.036 Uiso 0.50 1 calc PR . .
H10F H 0.6694 0.1117 0.1347 0.036 Uiso 0.50 1 calc PR . .
C11 C 0.63999(14) -0.08106(12) 0.15875(10) 0.0237(4) Uani 1 1 d . . .
H11A H 0.5751 -0.0794 0.1904 0.036 Uiso 1 1 calc R . .
H11B H 0.6990 -0.0744 0.1965 0.036 Uiso 1 1 calc R . .
H11C H 0.6455 -0.1358 0.1299 0.036 Uiso 1 1 calc R . .
C12 C 0.67393(13) -0.13122(12) -0.04479(10) 0.0209(4) Uani 1 1 d . . .
H12A H 0.6164 -0.0897 -0.0498 0.025 Uiso 1 1 calc R . .
H12B H 0.6457 -0.1835 -0.0188 0.025 Uiso 1 1 calc R . .
C13 C 0.71411(16) -0.15345(14) -0.13242(11) 0.0323(5) Uani 1 1 d . . .
H13A H 0.6572 -0.1773 -0.1654 0.048 Uiso 1 1 calc R . .
H13B H 0.7702 -0.1954 -0.1281 0.048 Uiso 1 1 calc R . .
H13C H 0.7403 -0.1017 -0.1593 0.048 Uiso 1 1 calc R . .
N1 N 0.88985(11) -0.12384(9) 0.11038(8) 0.0203(3) Uani 1 1 d . . .
N2 N 0.75665(11) -0.09423(9) 0.01103(8) 0.0177(3) Uani 1 1 d . . .
N3 N 0.83377(10) 0.02053(9) 0.09208(8) 0.0178(3) Uani 1 1 d . . .
N4 N 0.64057(11) -0.01070(9) 0.09725(9) 0.0190(3) Uani 1 1 d . . .
N5 N 0.72081(11) 0.05751(9) -0.02055(8) 0.0196(3) Uani 1 1 d . . .
O1 O 0.82030(10) -0.23110(8) 0.02868(8) 0.0251(3) Uani 1 1 d . . .
O2 O 0.95562(10) -0.01504(8) 0.19265(8) 0.0261(3) Uani 1 1 d . . .


_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
C1 O1 1.225(2) . ?
C1 N2 1.359(2) . ?
C1 N1 1.394(2) . ?
C2 N5 1.434(2) . ?
C2 N4 1.463(2) . ?
C2 N2 1.484(2) . ?
C2 N3 1.499(2) . ?
C3 O2 1.230(2) . ?
C3 N3 1.364(2) . ?
C3 N1 1.393(2) . ?
C4 N1 1.463(2) . ?
C4 C5 1.514(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N3 1.484(2) . ?
C6 C7 1.524(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N5 1.453(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 H8D 0.9600 . ?
C8 H8E 0.9600 . ?
C8 H8F 0.9600 . ?
C9 N5 1.457(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 H9D 0.9600 . ?
C9 H9E 0.9600 . ?
C9 H9F 0.9600 . ?
C10 N4 1.470(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10 H10D 0.9600 . ?
C10 H10E 0.9600 . ?
C10 H10F 0.9600 . ?
C11 N4 1.455(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N2 1.481(2) . ?
C12 C13 1.516(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
O1 C1 N2 122.79(16) . . ?
O1 C1 N1 120.23(15) . . ?
N2 C1 N1 116.98(15) . . ?
N5 C2 N4 109.55(13) . . ?
N5 C2 N2 112.60(13) . . ?
N4 C2 N2 107.60(12) . . ?
N5 C2 N3 106.65(12) . . ?
N4 C2 N3 114.11(13) . . ?
N2 C2 N3 106.40(12) . . ?
O2 C3 N3 122.97(16) . . ?
O2 C3 N1 120.29(15) . . ?
N3 C3 N1 116.68(14) . . ?
N1 C4 C5 111.55(15) . . ?
N1 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
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 . . ?
N3 C6 C7 112.93(14) . . ?
N3 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
N3 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N5 C8 H8A 109.5 . . ?
N5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N5 C8 H8D 109.5 . . ?
H8A C8 H8D 141.1 . . ?
H8B C8 H8D 56.3 . . ?
H8C C8 H8D 56.3 . . ?
N5 C8 H8E 109.5 . . ?
H8A C8 H8E 56.3 . . ?
H8B C8 H8E 141.1 . . ?
H8C C8 H8E 56.3 . . ?
H8D C8 H8E 109.5 . . ?
N5 C8 H8F 109.5 . . ?
H8A C8 H8F 56.3 . . ?
H8B C8 H8F 56.3 . . ?
H8C C8 H8F 141.1 . . ?
H8D C8 H8F 109.5 . . ?
H8E C8 H8F 109.5 . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N5 C9 H9D 109.5 . . ?
H9A C9 H9D 141.1 . . ?
H9B C9 H9D 56.3 . . ?
H9C C9 H9D 56.3 . . ?
N5 C9 H9E 109.5 . . ?
H9A C9 H9E 56.3 . . ?
H9B C9 H9E 141.1 . . ?
H9C C9 H9E 56.3 . . ?
H9D C9 H9E 109.5 . . ?
N5 C9 H9F 109.5 . . ?
H9A C9 H9F 56.3 . . ?
H9B C9 H9F 56.3 . . ?
H9C C9 H9F 141.1 . . ?
H9D C9 H9F 109.5 . . ?
H9E C9 H9F 109.5 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C10 H10D 109.5 . . ?
H10A C10 H10D 141.1 . . ?
H10B C10 H10D 56.3 . . ?
H10C C10 H10D 56.3 . . ?
N4 C10 H10E 109.5 . . ?
H10A C10 H10E 56.3 . . ?
H10B C10 H10E 141.1 . . ?
H10C C10 H10E 56.3 . . ?
H10D C10 H10E 109.5 . . ?
N4 C10 H10F 109.5 . . ?
H10A C10 H10F 56.3 . . ?
H10B C10 H10F 56.3 . . ?
H10C C10 H10F 141.1 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
N4 C11 H11A 109.5 . . ?
N4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 113.38(14) . . ?
N2 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
N2 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
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 . . ?
C3 N1 C1 123.42(14) . . ?
C3 N1 C4 118.25(14) . . ?
C1 N1 C4 118.13(14) . . ?
C1 N2 C12 114.79(14) . . ?
C1 N2 C2 124.62(13) . . ?
C12 N2 C2 116.29(13) . . ?
C3 N3 C6 115.18(13) . . ?
C3 N3 C2 122.95(13) . . ?
C6 N3 C2 119.61(12) . . ?
C11 N4 C2 114.93(13) . . ?
C11 N4 C10 108.77(13) . . ?
C2 N4 C10 114.73(13) . . ?
C2 N5 C8 116.98(13) . . ?
C2 N5 C9 122.84(13) . . ?
C8 N5 C9 112.16(13) . . ?

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
O2 C3 N1 C1 178.09(15) . . . . ?
N3 C3 N1 C1 -4.6(2) . . . . ?
O2 C3 N1 C4 3.3(2) . . . . ?
N3 C3 N1 C4 -179.35(14) . . . . ?
O1 C1 N1 C3 -179.99(15) . . . . ?
N2 C1 N1 C3 0.2(2) . . . . ?
O1 C1 N1 C4 -5.2(2) . . . . ?
N2 C1 N1 C4 174.94(14) . . . . ?
C5 C4 N1 C3 88.47(18) . . . . ?
C5 C4 N1 C1 -86.58(18) . . . . ?
O1 C1 N2 C12 9.2(2) . . . . ?
N1 C1 N2 C12 -170.95(13) . . . . ?
O1 C1 N2 C2 164.95(15) . . . . ?
N1 C1 N2 C2 -15.2(2) . . . . ?
C13 C12 N2 C1 -81.48(18) . . . . ?
C13 C12 N2 C2 120.68(16) . . . . ?
N5 C2 N2 C1 146.24(15) . . . . ?
N4 C2 N2 C1 -92.95(17) . . . . ?
N3 C2 N2 C1 29.75(19) . . . . ?
N5 C2 N2 C12 -58.34(17) . . . . ?
N4 C2 N2 C12 62.47(17) . . . . ?
N3 C2 N2 C12 -174.83(12) . . . . ?
O2 C3 N3 C6 4.1(2) . . . . ?
N1 C3 N3 C6 -173.15(13) . . . . ?
O2 C3 N3 C2 -158.74(15) . . . . ?
N1 C3 N3 C2 24.0(2) . . . . ?
C7 C6 N3 C3 68.91(19) . . . . ?
C7 C6 N3 C2 -127.62(15) . . . . ?
N5 C2 N3 C3 -154.63(14) . . . . ?
N4 C2 N3 C3 84.28(18) . . . . ?
N2 C2 N3 C3 -34.22(19) . . . . ?
N5 C2 N3 C6 43.25(18) . . . . ?
N4 C2 N3 C6 -77.85(17) . . . . ?
N2 C2 N3 C6 163.66(13) . . . . ?
N5 C2 N4 C11 171.85(13) . . . . ?
N2 C2 N4 C11 49.13(17) . . . . ?
N3 C2 N4 C11 -68.68(17) . . . . ?
N5 C2 N4 C10 -60.95(18) . . . . ?
N2 C2 N4 C10 176.34(13) . . . . ?
N3 C2 N4 C10 58.53(18) . . . . ?
N4 C2 N5 C8 -177.58(13) . . . . ?
N2 C2 N5 C8 -57.89(18) . . . . ?
N3 C2 N5 C8 58.45(17) . . . . ?
N4 C2 N5 C9 -31.2(2) . . . . ?
N2 C2 N5 C9 88.45(18) . . . . ?
N3 C2 N5 C9 -155.21(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.049
_database_code_depnum_ccdc_archive 'CCDC 1012671'
#######################################################################
#
#                 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_shelx

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H26 N4 O2'
_chemical_formula_sum            'C15 H26 N4 O2'
_chemical_formula_weight         294.40

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1256(12)
_cell_length_b                   8.7350(11)
_cell_length_c                   11.1764(16)
_cell_angle_alpha                101.997(12)
_cell_angle_beta                 106.888(13)
_cell_angle_gamma                90.243(11)
_cell_volume                     740.71(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1559
_cell_measurement_theta_min      4.2320
_cell_measurement_theta_max      65.1030

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.720
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_T_min  0.94496
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4706
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.189
_diffrn_reflns_theta_max         63.495
_diffrn_reflns_theta_full        63.500
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2394
_reflns_number_gt                1834
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0835P)²+0.0334P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2394
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1337
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_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_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
C1 C -0.0402(3) 0.1921(3) 0.7214(2) 0.0264(5) Uani 1 1 d . . . . .
H1A H -0.0934 0.1803 0.7865 0.032 Uiso 1 1 calc R U . . .
H1B H 0.0507 0.1200 0.7245 0.032 Uiso 1 1 calc R U . . .
C2 C -0.1742(4) 0.1476(3) 0.5910(2) 0.0402(6) Uani 1 1 d . . . . .
H2A H -0.2192 0.0414 0.5769 0.060 Uiso 1 1 calc R U . . .
H2B H -0.1221 0.1567 0.5257 0.060 Uiso 1 1 calc R U . . .
H2C H -0.2663 0.2166 0.5879 0.060 Uiso 1 1 calc R U . . .
C3 C -0.0424(3) 0.4701(3) 0.8116(2) 0.0244(5) Uani 1 1 d . . . . .
C4 C -0.0353(3) 0.7493(3) 0.9147(2) 0.0271(5) Uani 1 1 d . . . . .
H4A H 0.0562 0.8297 0.9626 0.033 Uiso 1 1 calc R U . . .
H4B H -0.0761 0.7081 0.9759 0.033 Uiso 1 1 calc R U . . .
C5 C -0.1819(3) 0.8231(3) 0.8325(2) 0.0313(6) Uani 1 1 d . . . . .
H5A H -0.2232 0.9045 0.8863 0.047 Uiso 1 1 calc R U . . .
H5B H -0.2739 0.7445 0.7859 0.047 Uiso 1 1 calc R U . . .
H5C H -0.1416 0.8669 0.7734 0.047 Uiso 1 1 calc R U . . .
C6 C 0.1504(3) 0.6647(3) 0.7788(2) 0.0246(3) Uani 1 1 d . . . . .
C7 C 0.3325(3) 0.5686(3) 0.6430(2) 0.0246(3) Uani 1 1 d . . . . .
H7A H 0.4491 0.5479 0.6871 0.030 Uiso 1 1 calc R U . . .
H7B H 0.3324 0.6772 0.6353 0.030 Uiso 1 1 calc R U . . .
C8 C 0.2720(3) 0.4601(3) 0.5096(2) 0.0331(6) Uani 1 1 d . . . . .
H8A H 0.3705 0.4264 0.4810 0.040 Uiso 1 1 calc R U . . .
H8B H 0.2004 0.5150 0.4486 0.040 Uiso 1 1 calc R U . . .
C9 C 0.1678(3) 0.3166(3) 0.5185(2) 0.0329(6) Uani 1 1 d . . . . .
H9A H 0.0494 0.3423 0.5095 0.039 Uiso 1 1 calc R U . . .
H9B H 0.1672 0.2298 0.4482 0.039 Uiso 1 1 calc R U . . .
C10 C 0.2144(3) 0.3840(3) 0.7454(2) 0.0246(3) Uani 1 1 d . . . . .
C11 C 0.3489(3) 0.3903(3) 0.8757(2) 0.0256(5) Uani 1 1 d . . . . .
H11A H 0.4578 0.4315 0.8718 0.031 Uiso 1 1 calc R U . . .
H11B H 0.3147 0.4657 0.9395 0.031 Uiso 1 1 calc R U . . .
C12 C 0.3815(3) 0.2390(3) 0.9243(2) 0.0287(5) Uani 1 1 d . . . . .
H12A H 0.4249 0.2655 1.0171 0.034 Uiso 1 1 calc R U . . .
H12B H 0.2728 0.1775 0.9008 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5090(3) 0.1386(3) 0.8724(2) 0.0315(6) Uani 1 1 d . . . . .
H13A H 0.5298 0.0498 0.9132 0.038 Uiso 1 1 calc R U . . .
H13B H 0.6177 0.2002 0.8957 0.038 Uiso 1 1 calc R U . . .
C14 C 0.4486(3) 0.0776(3) 0.7275(2) 0.0303(6) Uani 1 1 d . . . . .
H14A H 0.5366 0.0157 0.7023 0.036 Uiso 1 1 calc R U . . .
H14B H 0.3451 0.0090 0.7049 0.036 Uiso 1 1 calc R U . . .
C15 C 0.4109(3) 0.2068(3) 0.6525(2) 0.0277(5) Uani 1 1 d . . . . .
H15A H 0.4978 0.2930 0.6943 0.033 Uiso 1 1 calc R U . . .
H15B H 0.4206 0.1666 0.5673 0.033 Uiso 1 1 calc R U . . .
N1 N 0.0371(2) 0.3541(2) 0.75191(17) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.0358(2) 0.6216(2) 0.83958(17) 0.0241(4) Uani 1 1 d . . . . .
N3 N 0.2168(2) 0.5412(2) 0.71576(17) 0.0246(3) Uani 1 1 d . . . . .
N4 N 0.2392(2) 0.2674(2) 0.64061(17) 0.0262(5) Uani 1 1 d . . . . .
O1 O -0.1742(2) 0.44702(19) 0.83917(15) 0.0303(4) Uani 1 1 d . . . . .
O2 O 0.1824(2) 0.80206(18) 0.78119(16) 0.0329(4) Uani 1 1 d . . . . .


_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
C1 N1 1.476(3) . ?
C1 C2 1.517(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 O1 1.224(3) . ?
C3 N1 1.365(3) . ?
C3 N2 1.399(3) . ?
C4 N2 1.476(3) . ?
C4 C5 1.515(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 O2 1.220(3) . ?
C6 N3 1.364(3) . ?
C6 N2 1.393(3) . ?
C7 N3 1.458(3) . ?
C7 C8 1.531(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.546(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N4 1.473(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N4 1.447(3) . ?
C10 N3 1.479(3) . ?
C10 N1 1.488(3) . ?
C10 C11 1.536(3) . ?
C11 C12 1.527(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.524(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.525(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.522(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N4 1.474(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
N1 C1 C2 113.49(18) . . ?
N1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
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 . . ?
O1 C3 N1 123.6(2) . . ?
O1 C3 N2 120.7(2) . . ?
N1 C3 N2 115.64(19) . . ?
N2 C4 C5 113.19(19) . . ?
N2 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
N2 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
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 . . ?
O2 C6 N3 124.6(2) . . ?
O2 C6 N2 121.3(2) . . ?
N3 C6 N2 114.17(19) . . ?
N3 C7 C8 109.18(18) . . ?
N3 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N3 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C7 C8 C9 107.90(18) . . ?
C7 C8 H8A 110.1 . . ?
C9 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
C9 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
N4 C9 C8 112.4(2) . . ?
N4 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
N4 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
N4 C10 N3 109.57(16) . . ?
N4 C10 N1 107.78(18) . . ?
N3 C10 N1 105.30(16) . . ?
N4 C10 C11 114.70(18) . . ?
N3 C10 C11 108.13(18) . . ?
N1 C10 C11 110.94(17) . . ?
C12 C11 C10 118.64(19) . . ?
C12 C11 H11A 107.7 . . ?
C10 C11 H11A 107.7 . . ?
C12 C11 H11B 107.7 . . ?
C10 C11 H11B 107.7 . . ?
H11A C11 H11B 107.1 . . ?
C13 C12 C11 114.01(19) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 113.93(19) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 113.7(2) . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C13 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
N4 C15 C14 114.06(19) . . ?
N4 C15 H15A 108.7 . . ?
C14 C15 H15A 108.7 . . ?
N4 C15 H15B 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C3 N1 C1 117.52(18) . . ?
C3 N1 C10 120.55(18) . . ?
C1 N1 C10 120.46(17) . . ?
C6 N2 C3 123.44(18) . . ?
C6 N2 C4 117.19(18) . . ?
C3 N2 C4 117.89(18) . . ?
C6 N3 C7 120.12(18) . . ?
C6 N3 C10 121.60(17) . . ?
C7 N3 C10 116.30(17) . . ?
C10 N4 C9 110.32(17) . . ?
C10 N4 C15 119.12(18) . . ?
C9 N4 C15 111.84(17) . . ?

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
N3 C7 C8 C9 -24.5(2) . . . . ?
C7 C8 C9 N4 -36.5(2) . . . . ?
N4 C10 C11 C12 -53.0(3) . . . . ?
N3 C10 C11 C12 -175.60(18) . . . . ?
N1 C10 C11 C12 69.4(2) . . . . ?
C10 C11 C12 C13 84.0(3) . . . . ?
C11 C12 C13 C14 -63.2(3) . . . . ?
C12 C13 C14 C15 58.3(3) . . . . ?
C13 C14 C15 N4 -81.9(3) . . . . ?
O1 C3 N1 C1 -1.1(3) . . . . ?
N2 C3 N1 C1 179.54(17) . . . . ?
O1 C3 N1 C10 -167.29(19) . . . . ?
N2 C3 N1 C10 13.3(3) . . . . ?
C2 C1 N1 C3 89.3(2) . . . . ?
C2 C1 N1 C10 -104.5(2) . . . . ?
N4 C10 N1 C3 -158.96(17) . . . . ?
N3 C10 N1 C3 -42.1(2) . . . . ?
C11 C10 N1 C3 74.7(2) . . . . ?
N4 C10 N1 C1 35.2(2) . . . . ?
N3 C10 N1 C1 152.11(17) . . . . ?
C11 C10 N1 C1 -91.1(2) . . . . ?
O2 C6 N2 C3 161.5(2) . . . . ?
N3 C6 N2 C3 -16.9(3) . . . . ?
O2 C6 N2 C4 -4.3(3) . . . . ?
N3 C6 N2 C4 177.29(18) . . . . ?
O1 C3 N2 C6 -159.6(2) . . . . ?
N1 C3 N2 C6 19.8(3) . . . . ?
O1 C3 N2 C4 6.1(3) . . . . ?
N1 C3 N2 C4 -174.46(17) . . . . ?
C5 C4 N2 C6 79.6(3) . . . . ?
C5 C4 N2 C3 -87.1(2) . . . . ?
O2 C6 N3 C7 -1.1(3) . . . . ?
N2 C6 N3 C7 177.23(18) . . . . ?
O2 C6 N3 C10 162.3(2) . . . . ?
N2 C6 N3 C10 -19.4(3) . . . . ?
C8 C7 N3 C6 -131.1(2) . . . . ?
C8 C7 N3 C10 64.6(2) . . . . ?
N4 C10 N3 C6 161.53(19) . . . . ?
N1 C10 N3 C6 45.9(3) . . . . ?
C11 C10 N3 C6 -72.8(2) . . . . ?
N4 C10 N3 C7 -34.5(2) . . . . ?
N1 C10 N3 C7 -150.16(17) . . . . ?
C11 C10 N3 C7 91.2(2) . . . . ?
N3 C10 N4 C9 -30.5(2) . . . . ?
N1 C10 N4 C9 83.6(2) . . . . ?
C11 C10 N4 C9 -152.32(19) . . . . ?
N3 C10 N4 C15 100.8(2) . . . . ?
N1 C10 N4 C15 -145.10(18) . . . . ?
C11 C10 N4 C15 -21.0(3) . . . . ?
C8 C9 N4 C10 68.7(2) . . . . ?
C8 C9 N4 C15 -66.3(2) . . . . ?
C14 C15 N4 C10 81.9(3) . . . . ?
C14 C15 N4 C9 -147.5(2) . . . . ?

_refine_diff_density_max         0.585
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1012672'
