# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  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.
#
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#  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
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_mo_2013419_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H17 N3'
_chemical_formula_weight         203.29

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           ?
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   13.087(2)
_cell_length_b                   11.462(2)
_cell_length_c                   15.654(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.333(8)
_cell_angle_gamma                90.00
_cell_volume                     2346.4(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9867
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            15840
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         27.59
_reflns_number_total             5370
_reflns_number_gt                2984
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1270P)²+0.0000P] 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         5370
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.2200
_refine_ls_wR_factor_gt          0.1753
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.88863(12) 0.44649(14) 0.24233(10) 0.0442(4) Uani 1 1 d . . .
N1' N 0.80194(11) 0.94128(14) 1.02671(9) 0.0416(4) Uani 1 1 d . . .
N3' N 0.81245(12) 0.77487(15) 1.10327(10) 0.0508(5) Uani 1 1 d . . .
C11 C 0.9479(3) 0.0829(2) 0.40084(17) 0.0843(9) Uani 1 1 d . . .
H4 H 1.0135 0.1051 0.4252 0.126 Uiso 1 1 calc R . .
H5 H 0.9434 -0.0007 0.3983 0.126 Uiso 1 1 calc R . .
H1 H 0.8951 0.1126 0.4357 0.126 Uiso 1 1 calc R . .
C10 C 0.93467(17) 0.13296(18) 0.31093(14) 0.0545(6) Uani 1 1 d . . .
H6 H 0.8688 0.1058 0.2864 0.065 Uiso 1 1 calc R . .
C2 C 0.93250(14) 0.26445(18) 0.31232(12) 0.0480(5) Uani 1 1 d . . .
C1 C 0.88514(14) 0.32570(17) 0.24183(12) 0.0432(5) Uani 1 1 d . . .
C4 C 0.93569(14) 0.50791(18) 0.30999(12) 0.0472(5) Uani 1 1 d . . .
C7 C 0.93786(16) 0.63815(18) 0.30492(14) 0.0546(6) Uani 1 1 d . . .
H10 H 0.8707 0.6641 0.2823 0.065 Uiso 1 1 calc R . .
C9 C 1.01735(18) 0.6787(2) 0.24320(15) 0.0678(7) Uani 1 1 d . . .
H12 H 1.0840 0.6535 0.2635 0.102 Uiso 1 1 calc R . .
H2 H 1.0161 0.7623 0.2395 0.102 Uiso 1 1 calc R . .
H11 H 1.0021 0.6459 0.1877 0.102 Uiso 1 1 calc R . .
C12 C 1.01757(19) 0.0920(2) 0.25313(16) 0.0691(7) Uani 1 1 d . . .
H18 H 1.0052 0.1235 0.1969 0.104 Uiso 1 1 calc R . .
H19 H 1.0170 0.0083 0.2503 0.104 Uiso 1 1 calc R . .
H100 H 1.0830 0.1181 0.2756 0.104 Uiso 1 1 calc R . .
N3 N 0.97737(14) 0.32101(16) 0.37583(11) 0.0573(5) Uani 1 1 d . . .
C3 C 0.97742(17) 0.4412(2) 0.37359(14) 0.0584(6) Uani 1 1 d . . .
H16 H 1.0089 0.4798 0.4198 0.070 Uiso 1 1 calc R . .
N2 N 0.83341(14) 0.28513(15) 0.17254(10) 0.0548(5) Uani 1 1 d . . .
C6 C 0.80390(18) 0.38357(18) 0.12956(14) 0.0578(6) Uani 1 1 d . . .
H8 H 0.7659 0.3827 0.0781 0.069 Uiso 1 1 calc R . .
C5 C 0.83572(16) 0.48322(19) 0.16962(12) 0.0520(5) Uani 1 1 d . . .
H7 H 0.8242 0.5596 0.1517 0.062 Uiso 1 1 calc R . .
C8 C 0.9567(2) 0.6951(2) 0.39224(16) 0.0797(8) Uani 1 1 d . . .
H15 H 0.9065 0.6680 0.4307 0.119 Uiso 1 1 calc R . .
H14 H 0.9516 0.7783 0.3865 0.119 Uiso 1 1 calc R . .
H13 H 1.0238 0.6748 0.4145 0.119 Uiso 1 1 calc R . .
C9' C 0.91951(18) 1.1647(2) 0.97379(17) 0.0717(7) Uani 1 1 d . . .
H26 H 0.9476 1.1231 1.0225 0.108 Uiso 1 1 calc R . .
H20 H 0.9285 1.2470 0.9826 0.108 Uiso 1 1 calc R . .
H25 H 0.9541 1.1412 0.9237 0.108 Uiso 1 1 calc R . .
C7' C 0.80569(16) 1.13713(18) 0.96197(15) 0.0545(6) Uani 1 1 d . . .
H30 H 0.7725 1.1623 1.0138 0.065 Uiso 1 1 calc R . .
C4' C 0.79037(14) 1.00803(18) 0.95344(12) 0.0469(5) Uani 1 1 d . . .
C3' C 0.77375(17) 0.9464(2) 0.88014(13) 0.0584(6) Uani 1 1 d . . .
H31 H 0.7626 0.9889 0.8300 0.070 Uiso 1 1 calc R . .
N2' N 0.77190(14) 0.82658(17) 0.87346(11) 0.0604(5) Uani 1 1 d . . .
C2' C 0.78691(14) 0.76500(18) 0.94377(12) 0.0476(5) Uani 1 1 d . . .
C10' C 0.79258(17) 0.63402(18) 0.93701(14) 0.0565(6) Uani 1 1 d . . .
H33 H 0.7741 0.6035 0.9928 0.068 Uiso 1 1 calc R . .
C12' C 0.8986(3) 0.5951(3) 0.9243(4) 0.169(2) Uani 1 1 d . . .
H35 H 0.9022 0.5117 0.9288 0.253 Uiso 1 1 calc R . .
H21 H 0.9436 0.6297 0.9671 0.253 Uiso 1 1 calc R . .
H34 H 0.9189 0.6186 0.8686 0.253 Uiso 1 1 calc R . .
C11' C 0.7171(3) 0.5848(2) 0.8736(3) 0.1203(14) Uani 1 1 d . . .
H37 H 0.7333 0.6102 0.8173 0.180 Uiso 1 1 calc R . .
H36 H 0.6498 0.6113 0.8863 0.180 Uiso 1 1 calc R . .
H22 H 0.7193 0.5012 0.8762 0.180 Uiso 1 1 calc R . .
C5' C 0.81612(15) 0.97192(19) 1.11150(12) 0.0512(5) Uani 1 1 d . . .
H24 H 0.8209 1.0468 1.1341 0.061 Uiso 1 1 calc R . .
C6' C 0.82163(17) 0.86967(19) 1.15496(13) 0.0546(6) Uani 1 1 d . . .
H23 H 0.8308 0.8650 1.2141 0.066 Uiso 1 1 calc R . .
C1' C 0.80029(14) 0.81999(17) 1.02453(12) 0.0425(5) Uani 1 1 d . . .
C8' C 0.7580(2) 1.2060(2) 0.88710(18) 0.0839(8) Uani 1 1 d . . .
H28 H 0.7886 1.1823 0.8351 0.126 Uiso 1 1 calc R . .
H29 H 0.7696 1.2878 0.8962 0.126 Uiso 1 1 calc R . .
H27 H 0.6858 1.1911 0.8828 0.126 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
N1 C5 1.374(2) . ?
N1 C1 1.385(3) . ?
N1 C4 1.394(2) . ?
N1' C5' 1.378(2) . ?
N1' C4' 1.382(2) . ?
N1' C1' 1.391(3) . ?
N3' C1' 1.340(2) . ?
N3' C6' 1.357(2) . ?
C11 C10 1.523(3) . ?
C11 H4 0.9600 . ?
C11 H5 0.9600 . ?
C11 H1 0.9600 . ?
C10 C2 1.508(3) . ?
C10 C12 1.515(3) . ?
C10 H6 0.9800 . ?
C2 N3 1.306(2) . ?
C2 C1 1.428(3) . ?
C1 N2 1.338(2) . ?
C4 C3 1.353(3) . ?
C4 C7 1.495(3) . ?
C7 C9 1.521(3) . ?
C7 C8 1.526(3) . ?
C7 H10 0.9800 . ?
C9 H12 0.9600 . ?
C9 H2 0.9600 . ?
C9 H11 0.9600 . ?
C12 H18 0.9600 . ?
C12 H19 0.9600 . ?
C12 H100 0.9600 . ?
N3 C3 1.378(3) . ?
C3 H16 0.9300 . ?
N2 C6 1.362(3) . ?
C6 C5 1.360(3) . ?
C6 H8 0.9300 . ?
C5 H7 0.9300 . ?
C8 H15 0.9600 . ?
C8 H14 0.9600 . ?
C8 H13 0.9600 . ?
C9' C7' 1.527(3) . ?
C9' H26 0.9600 . ?
C9' H20 0.9600 . ?
C9' H25 0.9600 . ?
C7' C4' 1.499(3) . ?
C7' C8' 1.525(3) . ?
C7' H30 0.9800 . ?
C4' C3' 1.357(3) . ?
C3' N2' 1.378(3) . ?
C3' H31 0.9300 . ?
N2' C2' 1.316(2) . ?
C2' C1' 1.417(3) . ?
C2' C10' 1.507(3) . ?
C10' C12' 1.479(4) . ?
C10' C11' 1.483(3) . ?
C10' H33 0.9800 . ?
C12' H35 0.9600 . ?
C12' H21 0.9600 . ?
C12' H34 0.9600 . ?
C11' H37 0.9600 . ?
C11' H36 0.9600 . ?
C11' H22 0.9600 . ?
C5' C6' 1.356(3) . ?
C5' H24 0.9300 . ?
C6' H23 0.9300 . ?
C8' H28 0.9600 . ?
C8' H29 0.9600 . ?
C8' H27 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
C5 N1 C1 106.63(16) . . ?
C5 N1 C4 131.82(18) . . ?
C1 N1 C4 121.50(16) . . ?
C5' N1' C4' 131.62(18) . . ?
C5' N1' C1' 106.24(16) . . ?
C4' N1' C1' 122.14(16) . . ?
C1' N3' C6' 104.11(16) . . ?
C10 C11 H4 109.5 . . ?
C10 C11 H5 109.5 . . ?
H4 C11 H5 109.5 . . ?
C10 C11 H1 109.5 . . ?
H4 C11 H1 109.5 . . ?
H5 C11 H1 109.5 . . ?
C2 C10 C12 109.45(17) . . ?
C2 C10 C11 111.4(2) . . ?
C12 C10 C11 112.2(2) . . ?
C2 C10 H6 107.9 . . ?
C12 C10 H6 107.9 . . ?
C11 C10 H6 107.9 . . ?
N3 C2 C1 120.78(19) . . ?
N3 C2 C10 119.94(18) . . ?
C1 C2 C10 119.22(18) . . ?
N2 C1 N1 111.55(16) . . ?
N2 C1 C2 130.15(19) . . ?
N1 C1 C2 118.28(17) . . ?
C3 C4 N1 115.22(19) . . ?
C3 C4 C7 126.56(19) . . ?
N1 C4 C7 118.20(17) . . ?
C4 C7 C9 110.71(18) . . ?
C4 C7 C8 112.48(19) . . ?
C9 C7 C8 110.41(19) . . ?
C4 C7 H10 107.7 . . ?
C9 C7 H10 107.7 . . ?
C8 C7 H10 107.7 . . ?
C7 C9 H12 109.5 . . ?
C7 C9 H2 109.5 . . ?
H12 C9 H2 109.5 . . ?
C7 C9 H11 109.5 . . ?
H12 C9 H11 109.5 . . ?
H2 C9 H11 109.5 . . ?
C10 C12 H18 109.5 . . ?
C10 C12 H19 109.5 . . ?
H18 C12 H19 109.5 . . ?
C10 C12 H100 109.5 . . ?
H18 C12 H100 109.5 . . ?
H19 C12 H100 109.5 . . ?
C2 N3 C3 118.52(17) . . ?
C4 C3 N3 125.70(19) . . ?
C4 C3 H16 117.2 . . ?
N3 C3 H16 117.2 . . ?
C1 N2 C6 103.68(17) . . ?
C5 C6 N2 113.13(19) . . ?
C5 C6 H8 123.4 . . ?
N2 C6 H8 123.4 . . ?
C6 C5 N1 105.01(18) . . ?
C6 C5 H7 127.5 . . ?
N1 C5 H7 127.5 . . ?
C7 C8 H15 109.5 . . ?
C7 C8 H14 109.5 . . ?
H15 C8 H14 109.5 . . ?
C7 C8 H13 109.5 . . ?
H15 C8 H13 109.5 . . ?
H14 C8 H13 109.5 . . ?
C7' C9' H26 109.5 . . ?
C7' C9' H20 109.5 . . ?
H26 C9' H20 109.5 . . ?
C7' C9' H25 109.5 . . ?
H26 C9' H25 109.5 . . ?
H20 C9' H25 109.5 . . ?
C4' C7' C8' 113.15(19) . . ?
C4' C7' C9' 109.96(17) . . ?
C8' C7' C9' 110.7(2) . . ?
C4' C7' H30 107.6 . . ?
C8' C7' H30 107.6 . . ?
C9' C7' H30 107.6 . . ?
C3' C4' N1' 114.96(19) . . ?
C3' C4' C7' 127.26(19) . . ?
N1' C4' C7' 117.58(18) . . ?
C4' C3' N2' 125.78(19) . . ?
C4' C3' H31 117.1 . . ?
N2' C3' H31 117.1 . . ?
C2' N2' C3' 118.02(17) . . ?
N2' C2' C1' 121.10(19) . . ?
N2' C2' C10' 118.80(18) . . ?
C1' C2' C10' 120.08(18) . . ?
C12' C10' C11' 113.5(3) . . ?
C12' C10' C2' 111.0(2) . . ?
C11' C10' C2' 113.1(2) . . ?
C12' C10' H33 106.2 . . ?
C11' C10' H33 106.2 . . ?
C2' C10' H33 106.2 . . ?
C10' C12' H35 109.5 . . ?
C10' C12' H21 109.5 . . ?
H35 C12' H21 109.5 . . ?
C10' C12' H34 109.5 . . ?
H35 C12' H34 109.5 . . ?
H21 C12' H34 109.5 . . ?
C10' C11' H37 109.5 . . ?
C10' C11' H36 109.5 . . ?
H37 C11' H36 109.5 . . ?
C10' C11' H22 109.5 . . ?
H37 C11' H22 109.5 . . ?
H36 C11' H22 109.5 . . ?
C6' C5' N1' 105.38(18) . . ?
C6' C5' H24 127.3 . . ?
N1' C5' H24 127.3 . . ?
C5' C6' N3' 113.04(18) . . ?
C5' C6' H23 123.5 . . ?
N3' C6' H23 123.5 . . ?
N3' C1' N1' 111.22(16) . . ?
N3' C1' C2' 130.89(19) . . ?
N1' C1' C2' 117.89(17) . . ?
C7' C8' H28 109.5 . . ?
C7' C8' H29 109.5 . . ?
H28 C8' H29 109.5 . . ?
C7' C8' H27 109.5 . . ?
H28 C8' H27 109.5 . . ?
H29 C8' H27 109.5 . . ?

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
C12 C10 C2 N3 -99.3(2) . . . . ?
C11 C10 C2 N3 25.4(3) . . . . ?
C12 C10 C2 C1 77.9(2) . . . . ?
C11 C10 C2 C1 -157.5(2) . . . . ?
C5 N1 C1 N2 0.3(2) . . . . ?
C4 N1 C1 N2 177.80(16) . . . . ?
C5 N1 C1 C2 -178.31(17) . . . . ?
C4 N1 C1 C2 -0.8(3) . . . . ?
N3 C2 C1 N2 -177.9(2) . . . . ?
C10 C2 C1 N2 4.9(3) . . . . ?
N3 C2 C1 N1 0.4(3) . . . . ?
C10 C2 C1 N1 -176.71(17) . . . . ?
C5 N1 C4 C3 177.1(2) . . . . ?
C1 N1 C4 C3 0.4(3) . . . . ?
C5 N1 C4 C7 -4.4(3) . . . . ?
C1 N1 C4 C7 178.91(16) . . . . ?
C3 C4 C7 C9 102.6(3) . . . . ?
N1 C4 C7 C9 -75.7(2) . . . . ?
C3 C4 C7 C8 -21.5(3) . . . . ?
N1 C4 C7 C8 160.21(18) . . . . ?
C1 C2 N3 C3 0.4(3) . . . . ?
C10 C2 N3 C3 177.53(18) . . . . ?
N1 C4 C3 N3 0.5(3) . . . . ?
C7 C4 C3 N3 -177.85(19) . . . . ?
C2 N3 C3 C4 -0.9(3) . . . . ?
N1 C1 N2 C6 -0.3(2) . . . . ?
C2 C1 N2 C6 178.1(2) . . . . ?
C1 N2 C6 C5 0.2(2) . . . . ?
N2 C6 C5 N1 0.0(3) . . . . ?
C1 N1 C5 C6 -0.2(2) . . . . ?
C4 N1 C5 C6 -177.32(19) . . . . ?
C5' N1' C4' C3' -177.51(19) . . . . ?
C1' N1' C4' C3' 2.2(3) . . . . ?
C5' N1' C4' C7' 7.3(3) . . . . ?
C1' N1' C4' C7' -172.95(15) . . . . ?
C8' C7' C4' C3' 24.7(3) . . . . ?
C9' C7' C4' C3' -99.6(3) . . . . ?
C8' C7' C4' N1' -160.83(18) . . . . ?
C9' C7' C4' N1' 74.9(2) . . . . ?
N1' C4' C3' N2' -2.8(3) . . . . ?
C7' C4' C3' N2' 171.86(19) . . . . ?
C4' C3' N2' C2' 0.4(3) . . . . ?
C3' N2' C2' C1' 2.6(3) . . . . ?
C3' N2' C2' C10' -175.74(18) . . . . ?
N2' C2' C10' C12' 88.9(3) . . . . ?
C1' C2' C10' C12' -89.4(3) . . . . ?
N2' C2' C10' C11' -40.0(3) . . . . ?
C1' C2' C10' C11' 141.6(3) . . . . ?
C4' N1' C5' C6' 179.49(18) . . . . ?
C1' N1' C5' C6' -0.3(2) . . . . ?
N1' C5' C6' N3' 0.4(2) . . . . ?
C1' N3' C6' C5' -0.3(2) . . . . ?
C6' N3' C1' N1' 0.1(2) . . . . ?
C6' N3' C1' C2' 180.0(2) . . . . ?
C5' N1' C1' N3' 0.1(2) . . . . ?
C4' N1' C1' N3' -179.67(15) . . . . ?
C5' N1' C1' C2' -179.76(16) . . . . ?
C4' N1' C1' C2' 0.4(3) . . . . ?
N2' C2' C1' N3' 177.13(19) . . . . ?
C10' C2' C1' N3' -4.5(3) . . . . ?
N2' C2' C1' N1' -3.0(3) . . . . ?
C10' C2' C1' N1' 175.33(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.085
_database_code_depnum_ccdc_archive 'CCDC 979230'
#######################################################################
#
#                 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_mo_2013441_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 N6 O '
_chemical_formula_weight         340.43

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   Pccn

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

_cell_length_a                   10.079(8)
_cell_length_b                   11.523(10)
_cell_length_c                   15.799(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1835(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(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    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            7300
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1598
_reflns_number_gt                893
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0899P)²+0.2525P] 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         1598
_refine_ls_number_parameters     120
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1751
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1S O 0.2500 0.7500 0.2590(2) 0.0509(8) Uani 1 2 d SD . .
N1 N 0.8561(2) 0.4231(2) 0.34772(16) 0.0489(7) Uani 1 1 d . . .
N2 N 1.0610(2) 0.6816(2) 0.38938(16) 0.0502(7) Uani 1 1 d . . .
H5 H 1.1222 0.6909 0.3520 0.060 Uiso 1 1 calc R . .
N3 N 1.0425(3) 0.7532(2) 0.45674(18) 0.0646(8) Uani 1 1 d . . .
C8 C 0.9510(3) 0.5043(3) 0.1734(2) 0.0608(9) Uani 1 1 d . . .
H8 H 0.8768 0.4520 0.1739 0.091 Uiso 1 1 calc R . .
H1 H 1.0040 0.4901 0.1240 0.091 Uiso 1 1 calc R . .
H9 H 0.9193 0.5828 0.1725 0.091 Uiso 1 1 calc R . .
C7 C 1.0351(3) 0.4851(3) 0.25296(18) 0.0494(8) Uani 1 1 d . . .
H7 H 1.1037 0.5453 0.2537 0.059 Uiso 1 1 calc R . .
C6 C 0.9526(3) 0.5004(2) 0.33169(17) 0.0420(7) Uani 1 1 d . . .
C5 C 0.9710(3) 0.5931(2) 0.38803(17) 0.0410(7) Uani 1 1 d . . .
C3 C 0.8905(3) 0.6069(3) 0.4602(2) 0.0482(8) Uani 1 1 d . . .
C2 C 0.7921(3) 0.5245(3) 0.4756(2) 0.0556(9) Uani 1 1 d . . .
H2 H 0.7368 0.5299 0.5226 0.067 Uiso 1 1 calc R . .
C9 C 1.1059(3) 0.3680(3) 0.2513(2) 0.0617(10) Uani 1 1 d . . .
H3 H 1.1620 0.3612 0.3001 0.093 Uiso 1 1 calc R . .
H11 H 1.1587 0.3623 0.2009 0.093 Uiso 1 1 calc R . .
H10 H 1.0413 0.3067 0.2518 0.093 Uiso 1 1 calc R . .
C1 C 0.7804(3) 0.4357(3) 0.4190(2) 0.0555(9) Uani 1 1 d . . .
H6 H 0.7162 0.3796 0.4296 0.067 Uiso 1 1 calc R . .
C4 C 0.9417(4) 0.7092(3) 0.4994(2) 0.0617(10) Uani 1 1 d . . .
H4 H 0.9081 0.7410 0.5491 0.074 Uiso 1 1 calc R . .
H1A H 0.213(4) 0.807(3) 0.231(2) 0.110(16) Uiso 1 1 d 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
O1S H1A 0.873(18) . ?
N1 C6 1.343(4) . ?
N1 C1 1.368(4) . ?
N2 N3 1.360(4) . ?
N2 C5 1.365(4) . ?
N2 H5 0.8600 . ?
N3 C4 1.321(4) . ?
C8 C7 1.532(4) . ?
C8 H8 0.9600 . ?
C8 H1 0.9600 . ?
C8 H9 0.9600 . ?
C7 C6 1.506(4) . ?
C7 C9 1.527(4) . ?
C7 H7 0.9800 . ?
C6 C5 1.403(4) . ?
C5 C3 1.409(4) . ?
C3 C2 1.394(4) . ?
C3 C4 1.428(5) . ?
C2 C1 1.365(5) . ?
C2 H2 0.9300 . ?
C9 H3 0.9600 . ?
C9 H11 0.9600 . ?
C9 H10 0.9600 . ?
C1 H6 0.9300 . ?
C4 H4 0.9300 . ?

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
C6 N1 C1 119.3(3) . . ?
N3 N2 C5 112.0(3) . . ?
N3 N2 H5 124.0 . . ?
C5 N2 H5 124.0 . . ?
C4 N3 N2 105.8(3) . . ?
C7 C8 H8 109.5 . . ?
C7 C8 H1 109.5 . . ?
H8 C8 H1 109.5 . . ?
C7 C8 H9 109.5 . . ?
H8 C8 H9 109.5 . . ?
H1 C8 H9 109.5 . . ?
C6 C7 C9 112.1(2) . . ?
C6 C7 C8 110.8(2) . . ?
C9 C7 C8 111.8(3) . . ?
C6 C7 H7 107.3 . . ?
C9 C7 H7 107.3 . . ?
C8 C7 H7 107.3 . . ?
N1 C6 C5 118.8(3) . . ?
N1 C6 C7 118.5(3) . . ?
C5 C6 C7 122.7(2) . . ?
N2 C5 C6 131.8(3) . . ?
N2 C5 C3 106.6(3) . . ?
C6 C5 C3 121.6(3) . . ?
C2 C3 C5 118.3(3) . . ?
C2 C3 C4 138.0(3) . . ?
C5 C3 C4 103.7(3) . . ?
C1 C2 C3 117.2(3) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 H2 121.4 . . ?
C7 C9 H3 109.5 . . ?
C7 C9 H11 109.5 . . ?
H3 C9 H11 109.5 . . ?
C7 C9 H10 109.5 . . ?
H3 C9 H10 109.5 . . ?
H11 C9 H10 109.5 . . ?
C2 C1 N1 124.8(3) . . ?
C2 C1 H6 117.6 . . ?
N1 C1 H6 117.6 . . ?
N3 C4 C3 111.9(3) . . ?
N3 C4 H4 124.0 . . ?
C3 C4 H4 124.0 . . ?

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
C5 N2 N3 C4 1.1(3) . . . . ?
C1 N1 C6 C5 -1.2(4) . . . . ?
C1 N1 C6 C7 180.0(3) . . . . ?
C9 C7 C6 N1 -58.6(3) . . . . ?
C8 C7 C6 N1 67.1(3) . . . . ?
C9 C7 C6 C5 122.6(3) . . . . ?
C8 C7 C6 C5 -111.7(3) . . . . ?
N3 N2 C5 C6 -179.9(3) . . . . ?
N3 N2 C5 C3 -1.3(3) . . . . ?
N1 C6 C5 N2 178.2(3) . . . . ?
C7 C6 C5 N2 -3.0(5) . . . . ?
N1 C6 C5 C3 -0.3(4) . . . . ?
C7 C6 C5 C3 178.5(3) . . . . ?
N2 C5 C3 C2 -177.8(3) . . . . ?
C6 C5 C3 C2 1.0(4) . . . . ?
N2 C5 C3 C4 0.9(3) . . . . ?
C6 C5 C3 C4 179.7(3) . . . . ?
C5 C3 C2 C1 -0.2(4) . . . . ?
C4 C3 C2 C1 -178.3(4) . . . . ?
C3 C2 C1 N1 -1.4(5) . . . . ?
C6 N1 C1 C2 2.1(5) . . . . ?
N2 N3 C4 C3 -0.5(4) . . . . ?
C2 C3 C4 N3 178.0(3) . . . . ?
C5 C3 C4 N3 -0.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 979231'
#######################################################################
#
#                 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_cu_2013487_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 N3'
_chemical_formula_weight         161.21

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   7.9968(2)
_cell_length_b                   4.75170(10)
_cell_length_c                   22.7801(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.9490(10)
_cell_angle_gamma                90.00
_cell_volume                     860.95(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(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    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.620
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_reflns_number            11629
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.90
_diffrn_reflns_theta_max         67.89
_reflns_number_total             1557
_reflns_number_gt                1281
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0436P)²+0.1485P] 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         1557
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1624(2) 1.2283(4) 0.04516(8) 0.0669(5) Uani 1 1 d . . .
H1 H 0.0671 1.2991 0.0232 0.080 Uiso 1 1 calc R . .
N2 N 0.13431(17) 1.0441(3) 0.08752(7) 0.0629(4) Uani 1 1 d . . .
C2 C 0.26717(19) 0.9318(3) 0.11934(7) 0.0512(4) Uani 1 1 d . . .
C3 C 0.42904(19) 1.0009(3) 0.10625(7) 0.0480(4) Uani 1 1 d . . .
C6 C 0.43939(19) 1.2026(3) 0.06157(7) 0.0484(4) Uani 1 1 d . . .
N1 N 0.30809(17) 1.3233(3) 0.03033(6) 0.0576(4) Uani 1 1 d . . .
N3 N 0.60370(16) 1.2499(3) 0.05555(6) 0.0555(4) Uani 1 1 d . . .
H4 H 0.6419 1.3664 0.0313 0.067 Uiso 1 1 calc R . .
C7 C 0.2381(2) 0.7418(4) 0.17044(8) 0.0623(5) Uani 1 1 d . . .
H5 H 0.3054 0.5712 0.1672 0.075 Uiso 1 1 calc R . .
C8 C 0.0550(3) 0.6531(5) 0.17079(11) 0.0841(7) Uani 1 1 d . . .
H7 H -0.0117 0.8142 0.1785 0.126 Uiso 1 1 calc R . .
H11 H 0.0465 0.5146 0.2010 0.126 Uiso 1 1 calc R . .
H6 H 0.0151 0.5747 0.1331 0.126 Uiso 1 1 calc R . .
C4 C 0.5980(2) 0.9263(4) 0.12641(7) 0.0575(4) Uani 1 1 d . . .
H2 H 0.6324 0.7965 0.1558 0.069 Uiso 1 1 calc R . .
C5 C 0.6987(2) 1.0810(4) 0.09456(8) 0.0596(5) Uani 1 1 d . . .
H3 H 0.8156 1.0734 0.0986 0.071 Uiso 1 1 calc R . .
C9 C 0.3004(3) 0.8879(5) 0.22840(8) 0.0834(6) Uani 1 1 d . . .
H10 H 0.4181 0.9293 0.2288 0.125 Uiso 1 1 calc R . .
H9 H 0.2833 0.7665 0.2609 0.125 Uiso 1 1 calc R . .
H8 H 0.2391 1.0598 0.2318 0.125 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
C1 N1 1.325(2) . ?
C1 N2 1.339(2) . ?
C1 H1 0.9300 . ?
N2 C2 1.334(2) . ?
C2 C3 1.397(2) . ?
C2 C7 1.510(2) . ?
C3 C6 1.407(2) . ?
C3 C4 1.426(2) . ?
C6 N1 1.335(2) . ?
C6 N3 1.354(2) . ?
N3 C5 1.368(2) . ?
N3 H4 0.8600 . ?
C7 C8 1.524(3) . ?
C7 C9 1.529(3) . ?
C7 H5 0.9800 . ?
C8 H7 0.9600 . ?
C8 H11 0.9600 . ?
C8 H6 0.9600 . ?
C4 C5 1.356(2) . ?
C4 H2 0.9300 . ?
C5 H3 0.9300 . ?
C9 H10 0.9600 . ?
C9 H9 0.9600 . ?
C9 H8 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
N1 C1 N2 128.61(16) . . ?
N1 C1 H1 115.7 . . ?
N2 C1 H1 115.7 . . ?
C2 N2 C1 117.99(14) . . ?
N2 C2 C3 119.56(14) . . ?
N2 C2 C7 118.70(14) . . ?
C3 C2 C7 121.69(14) . . ?
C2 C3 C6 116.09(14) . . ?
C2 C3 C4 137.78(15) . . ?
C6 C3 C4 106.12(13) . . ?
N1 C6 N3 126.34(14) . . ?
N1 C6 C3 125.18(14) . . ?
N3 C6 C3 108.47(13) . . ?
C1 N1 C6 112.42(14) . . ?
C6 N3 C5 108.45(13) . . ?
C6 N3 H4 125.8 . . ?
C5 N3 H4 125.8 . . ?
C2 C7 C8 113.22(16) . . ?
C2 C7 C9 109.36(15) . . ?
C8 C7 C9 110.41(16) . . ?
C2 C7 H5 107.9 . . ?
C8 C7 H5 107.9 . . ?
C9 C7 H5 107.9 . . ?
C7 C8 H7 109.5 . . ?
C7 C8 H11 109.5 . . ?
H7 C8 H11 109.5 . . ?
C7 C8 H6 109.5 . . ?
H7 C8 H6 109.5 . . ?
H11 C8 H6 109.5 . . ?
C5 C4 C3 106.78(15) . . ?
C5 C4 H2 126.6 . . ?
C3 C4 H2 126.6 . . ?
C4 C5 N3 110.17(15) . . ?
C4 C5 H3 124.9 . . ?
N3 C5 H3 124.9 . . ?
C7 C9 H10 109.5 . . ?
C7 C9 H9 109.5 . . ?
H10 C9 H9 109.5 . . ?
C7 C9 H8 109.5 . . ?
H10 C9 H8 109.5 . . ?
H9 C9 H8 109.5 . . ?

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
N1 C1 N2 C2 -1.5(3) . . . . ?
C1 N2 C2 C3 -2.3(3) . . . . ?
C1 N2 C2 C7 175.16(16) . . . . ?
N2 C2 C3 C6 3.8(2) . . . . ?
C7 C2 C3 C6 -173.54(14) . . . . ?
N2 C2 C3 C4 -177.28(18) . . . . ?
C7 C2 C3 C4 5.3(3) . . . . ?
C2 C3 C6 N1 -2.1(2) . . . . ?
C4 C3 C6 N1 178.67(15) . . . . ?
C2 C3 C6 N3 178.48(13) . . . . ?
C4 C3 C6 N3 -0.73(18) . . . . ?
N2 C1 N1 C6 3.1(3) . . . . ?
N3 C6 N1 C1 178.15(16) . . . . ?
C3 C6 N1 C1 -1.2(2) . . . . ?
N1 C6 N3 C5 -178.53(16) . . . . ?
C3 C6 N3 C5 0.86(18) . . . . ?
N2 C2 C7 C8 12.4(2) . . . . ?
C3 C2 C7 C8 -170.17(16) . . . . ?
N2 C2 C7 C9 -111.14(19) . . . . ?
C3 C2 C7 C9 66.3(2) . . . . ?
C2 C3 C4 C5 -178.63(19) . . . . ?
C6 C3 C4 C5 0.32(19) . . . . ?
C3 C4 C5 N3 0.2(2) . . . . ?
C6 N3 C5 C4 -0.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        67.89
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039
_database_code_depnum_ccdc_archive 'CCDC 979233'
#######################################################################
#
#                 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_mo_2013449_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            ' C12 H17 N3 '
_chemical_formula_weight         203.29

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           ?
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   12.9851(18)
_cell_length_b                   14.1460(19)
_cell_length_c                   13.3141(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.871(9)
_cell_angle_gamma                90.00
_cell_volume                     2432.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.11
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9912
_exptl_absorpt_correction_T_max  0.9941
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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_reflns_number            23913
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4283
_reflns_number_gt                2809
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.2000P)²+0.5144P] 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         4283
_refine_ls_number_parameters     279
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0801
_refine_ls_wR_factor_ref         0.3010
_refine_ls_wR_factor_gt          0.2534
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.002

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
N3' N 0.61483(17) -0.04860(17) 0.20605(17) 0.0595(7) Uani 1 1 d . . .
N1 N 0.7257(2) 0.99021(18) 0.8479(2) 0.0740(8) Uani 1 1 d . . .
C7 C 0.7378(4) 0.7686(3) 0.5753(3) 0.1061(14) Uani 1 1 d . . .
H103 H 0.7799 0.7117 0.5698 0.127 Uiso 1 1 calc R . .
N2 N 0.76935(18) 0.83991(17) 0.88279(17) 0.0605(7) Uani 1 1 d . . .
C12' C 0.5145(4) 0.1276(4) 0.0858(4) 0.1362(19) Uani 1 1 d . . .
H12 H 0.5636 0.1692 0.0594 0.204 Uiso 1 1 calc R . .
H1 H 0.4468 0.1557 0.0766 0.204 Uiso 1 1 calc R . .
H3 H 0.5135 0.0683 0.0508 0.204 Uiso 1 1 calc R . .
C10' C 0.5444(3) 0.1119(2) 0.1948(3) 0.0756(9) Uani 1 1 d . . .
H4 H 0.4863 0.0776 0.2191 0.091 Uiso 1 1 calc R . .
C3' C 0.6348(2) 0.0459(2) 0.2108(2) 0.0626(8) Uani 1 1 d . . .
C2' C 0.5236(2) -0.0998(2) 0.1911(3) 0.0737(9) Uani 1 1 d . . .
H2' H 0.4565 -0.0764 0.1798 0.088 Uiso 1 1 calc R . .
C1' C 0.5534(3) -0.1907(3) 0.1967(3) 0.0897(11) Uani 1 1 d . . .
H2 H 0.5073 -0.2412 0.1897 0.108 Uiso 1 1 calc R . .
C6' C 0.6951(2) -0.1152(2) 0.2191(2) 0.0639(8) Uani 1 1 d . . .
N1' N 0.6585(2) -0.20172(19) 0.2136(2) 0.0835(9) Uani 1 1 d . . .
N2' N 0.7952(2) -0.0891(2) 0.2339(2) 0.0736(8) Uani 1 1 d . . .
C5' C 0.8149(3) 0.0027(3) 0.2379(3) 0.0772(9) Uani 1 1 d . . .
C4' C 0.7356(3) 0.0714(2) 0.2271(3) 0.0740(9) Uani 1 1 d . . .
H8 H 0.7529 0.1352 0.2313 0.089 Uiso 1 1 calc R . .
C7' C 0.9264(3) 0.0329(3) 0.2526(4) 0.1070(14) Uani 1 1 d D . .
H101 H 0.9229 0.1007 0.2672 0.128 Uiso 1 1 calc R . .
C11' C 0.5556(5) 0.1989(5) 0.2563(6) 0.177(3) Uani 1 1 d . . .
H100 H 0.5629 0.1825 0.3266 0.266 Uiso 1 1 calc R . .
H10 H 0.4953 0.2378 0.2417 0.266 Uiso 1 1 calc R . .
H9 H 0.6158 0.2330 0.2405 0.266 Uiso 1 1 calc R . .
C1 C 0.7472(3) 0.9769(3) 0.9495(3) 0.0804(10) Uani 1 1 d . . .
H1A H 0.7435 1.0248 0.9969 0.097 Uiso 1 1 calc R . .
C6 C 0.7404(2) 0.9063(2) 0.8079(2) 0.0605(7) Uani 1 1 d . . .
N3 N 0.7305(2) 0.88392(18) 0.70866(19) 0.0724(8) Uani 1 1 d . . .
C5 C 0.7490(3) 0.7953(2) 0.6854(2) 0.0741(9) Uani 1 1 d . . .
C8 C 0.7817(8) 0.8426(5) 0.5105(4) 0.213(4) Uani 1 1 d . . .
H27 H 0.7421 0.8997 0.5125 0.319 Uiso 1 1 calc R . .
H14 H 0.7787 0.8203 0.4422 0.319 Uiso 1 1 calc R . .
H28 H 0.8524 0.8550 0.5354 0.319 Uiso 1 1 calc R . .
C3 C 0.7883(2) 0.7477(2) 0.8592(2) 0.0659(8) Uani 1 1 d . . .
C4 C 0.7771(3) 0.7258(2) 0.7599(2) 0.0726(9) Uani 1 1 d . . .
H16 H 0.7881 0.6640 0.7400 0.087 Uiso 1 1 calc R . .
C10 C 0.8161(3) 0.6800(2) 0.9460(3) 0.0847(11) Uani 1 1 d . . .
H23 H 0.8577 0.7159 0.9985 0.102 Uiso 1 1 calc R . .
C11 C 0.7197(4) 0.6497(3) 0.9907(4) 0.1181(16) Uani 1 1 d . . .
H18 H 0.6816 0.7046 1.0077 0.177 Uiso 1 1 calc R . .
H17 H 0.7383 0.6131 1.0505 0.177 Uiso 1 1 calc R . .
H19 H 0.6777 0.6122 0.9425 0.177 Uiso 1 1 calc R . .
C12 C 0.8818(4) 0.5984(3) 0.9186(4) 0.1158(15) Uani 1 1 d . . .
H20 H 0.9078 0.5652 0.9788 0.174 Uiso 1 1 calc R . .
H21 H 0.9387 0.6216 0.8850 0.174 Uiso 1 1 calc R . .
H22 H 0.8407 0.5562 0.8744 0.174 Uiso 1 1 calc R . .
C2 C 0.7741(3) 0.8876(2) 0.9737(2) 0.0764(9) Uani 1 1 d . . .
H24 H 0.7920 0.8630 1.0379 0.092 Uiso 1 1 calc R . .
C8' C 0.9821(5) -0.0043(8) 0.3377(6) 0.242(5) Uani 1 1 d D . .
H10A H 0.9757 -0.0720 0.3370 0.363 Uiso 1 1 calc R . .
H10B H 0.9555 0.0204 0.3971 0.363 Uiso 1 1 calc R . .
H10C H 1.0537 0.0127 0.3382 0.363 Uiso 1 1 calc R . .
C9 C 0.6307(6) 0.7412(8) 0.5422(5) 0.233(5) Uani 1 1 d . . .
H10D H 0.5909 0.7966 0.5225 0.349 Uiso 1 1 calc R . .
H10E H 0.6011 0.7102 0.5966 0.349 Uiso 1 1 calc R . .
H10F H 0.6299 0.6989 0.4858 0.349 Uiso 1 1 calc R . .
C9' C 0.9732(5) 0.0291(10) 0.1628(6) 0.294(7) Uani 1 1 d D . .
H10G H 0.9207 0.0260 0.1066 0.441 Uiso 1 1 calc R . .
H10H H 1.0164 -0.0259 0.1631 0.441 Uiso 1 1 calc R . .
H10I H 1.0145 0.0847 0.1570 0.441 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
N3' C3' 1.362(4) . ?
N3' C2' 1.385(4) . ?
N3' C6' 1.403(4) . ?
N1 C6 1.322(4) . ?
N1 C1 1.366(5) . ?
C7 C9 1.468(8) . ?
C7 C8 1.506(7) . ?
C7 C5 1.505(5) . ?
C7 H103 0.9800 . ?
N2 C3 1.370(4) . ?
N2 C2 1.382(4) . ?
N2 C6 1.393(4) . ?
C12' C10' 1.480(6) . ?
C12' H12 0.9600 . ?
C12' H1 0.9600 . ?
C12' H3 0.9600 . ?
C10' C11' 1.478(6) . ?
C10' C3' 1.497(4) . ?
C10' H4 0.9800 . ?
C3' C4' 1.353(4) . ?
C2' C1' 1.343(5) . ?
C2' H2' 0.9300 . ?
C1' N1' 1.368(5) . ?
C1' H2 0.9300 . ?
C6' N1' 1.312(4) . ?
C6' N2' 1.347(4) . ?
N2' C5' 1.323(4) . ?
C5' C4' 1.413(5) . ?
C5' C7' 1.503(5) . ?
C4' H8 0.9300 . ?
C7' C8' 1.385(8) . ?
C7' C9' 1.396(8) . ?
C7' H101 0.9800 . ?
C11' H100 0.9600 . ?
C11' H10 0.9600 . ?
C11' H9 0.9600 . ?
C1 C2 1.342(5) . ?
C1 H1A 0.9300 . ?
C6 N3 1.353(4) . ?
N3 C5 1.320(4) . ?
C5 C4 1.417(4) . ?
C8 H27 0.9600 . ?
C8 H14 0.9600 . ?
C8 H28 0.9600 . ?
C3 C4 1.351(4) . ?
C3 C10 1.516(5) . ?
C4 H16 0.9300 . ?
C10 C12 1.502(6) . ?
C10 C11 1.502(6) . ?
C10 H23 0.9800 . ?
C11 H18 0.9600 . ?
C11 H17 0.9600 . ?
C11 H19 0.9600 . ?
C12 H20 0.9600 . ?
C12 H21 0.9600 . ?
C12 H22 0.9600 . ?
C2 H24 0.9300 . ?
C8' H10A 0.9600 . ?
C8' H10B 0.9600 . ?
C8' H10C 0.9600 . ?
C9 H10D 0.9600 . ?
C9 H10E 0.9600 . ?
C9 H10F 0.9600 . ?
C9' H10G 0.9600 . ?
C9' H10H 0.9600 . ?
C9' H10I 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
C3' N3' C2' 132.5(3) . . ?
C3' N3' C6' 121.2(2) . . ?
C2' N3' C6' 106.2(3) . . ?
C6 N1 C1 104.5(3) . . ?
C9 C7 C8 114.5(6) . . ?
C9 C7 C5 110.7(4) . . ?
C8 C7 C5 112.3(4) . . ?
C9 C7 H103 106.3 . . ?
C8 C7 H103 106.3 . . ?
C5 C7 H103 106.3 . . ?
C3 N2 C2 132.3(3) . . ?
C3 N2 C6 121.3(2) . . ?
C2 N2 C6 106.4(3) . . ?
C10' C12' H12 109.5 . . ?
C10' C12' H1 109.5 . . ?
H12 C12' H1 109.5 . . ?
C10' C12' H3 109.5 . . ?
H12 C12' H3 109.5 . . ?
H1 C12' H3 109.5 . . ?
C11' C10' C12' 114.7(5) . . ?
C11' C10' C3' 114.2(3) . . ?
C12' C10' C3' 110.9(3) . . ?
C11' C10' H4 105.3 . . ?
C12' C10' H4 105.3 . . ?
C3' C10' H4 105.3 . . ?
C4' C3' N3' 116.4(3) . . ?
C4' C3' C10' 126.0(3) . . ?
N3' C3' C10' 117.5(3) . . ?
C1' C2' N3' 104.8(3) . . ?
C1' C2' H2' 127.6 . . ?
N3' C2' H2' 127.6 . . ?
C2' C1' N1' 113.3(3) . . ?
C2' C1' H2 123.4 . . ?
N1' C1' H2 123.4 . . ?
N1' C6' N2' 127.1(3) . . ?
N1' C6' N3' 111.1(3) . . ?
N2' C6' N3' 121.8(3) . . ?
C6' N1' C1' 104.6(3) . . ?
C5' N2' C6' 117.1(3) . . ?
N2' C5' C4' 122.3(3) . . ?
N2' C5' C7' 117.7(3) . . ?
C4' C5' C7' 120.0(3) . . ?
C3' C4' C5' 121.1(3) . . ?
C3' C4' H8 119.5 . . ?
C5' C4' H8 119.5 . . ?
C8' C7' C9' 116.7(7) . . ?
C8' C7' C5' 114.4(5) . . ?
C9' C7' C5' 112.0(4) . . ?
C8' C7' H101 103.9 . . ?
C9' C7' H101 103.9 . . ?
C5' C7' H101 103.9 . . ?
C10' C11' H100 109.5 . . ?
C10' C11' H10 109.5 . . ?
H100 C11' H10 109.5 . . ?
C10' C11' H9 109.5 . . ?
H100 C11' H9 109.5 . . ?
H10 C11' H9 109.5 . . ?
C2 C1 N1 113.0(3) . . ?
C2 C1 H1A 123.5 . . ?
N1 C1 H1A 123.5 . . ?
N1 C6 N3 126.8(3) . . ?
N1 C6 N2 110.9(3) . . ?
N3 C6 N2 122.2(3) . . ?
C5 N3 C6 116.8(3) . . ?
N3 C5 C4 122.3(3) . . ?
N3 C5 C7 117.7(3) . . ?
C4 C5 C7 120.0(3) . . ?
C7 C8 H27 109.5 . . ?
C7 C8 H14 109.5 . . ?
H27 C8 H14 109.5 . . ?
C7 C8 H28 109.5 . . ?
H27 C8 H28 109.5 . . ?
H14 C8 H28 109.5 . . ?
C4 C3 N2 116.0(3) . . ?
C4 C3 C10 126.5(3) . . ?
N2 C3 C10 117.4(3) . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 H16 119.3 . . ?
C5 C4 H16 119.3 . . ?
C12 C10 C11 113.2(4) . . ?
C12 C10 C3 113.4(3) . . ?
C11 C10 C3 109.8(3) . . ?
C12 C10 H23 106.7 . . ?
C11 C10 H23 106.7 . . ?
C3 C10 H23 106.7 . . ?
C10 C11 H18 109.5 . . ?
C10 C11 H17 109.5 . . ?
H18 C11 H17 109.5 . . ?
C10 C11 H19 109.5 . . ?
H18 C11 H19 109.5 . . ?
H17 C11 H19 109.5 . . ?
C10 C12 H20 109.5 . . ?
C10 C12 H21 109.5 . . ?
H20 C12 H21 109.5 . . ?
C10 C12 H22 109.5 . . ?
H20 C12 H22 109.5 . . ?
H21 C12 H22 109.5 . . ?
C1 C2 N2 105.2(3) . . ?
C1 C2 H24 127.4 . . ?
N2 C2 H24 127.4 . . ?
C7' C8' H10A 109.5 . . ?
C7' C8' H10B 109.5 . . ?
H10A C8' H10B 109.5 . . ?
C7' C8' H10C 109.5 . . ?
H10A C8' H10C 109.5 . . ?
H10B C8' H10C 109.5 . . ?
C7 C9 H10D 109.5 . . ?
C7 C9 H10E 109.5 . . ?
H10D C9 H10E 109.5 . . ?
C7 C9 H10F 109.5 . . ?
H10D C9 H10F 109.5 . . ?
H10E C9 H10F 109.5 . . ?
C7' C9' H10G 109.5 . . ?
C7' C9' H10H 109.5 . . ?
H10G C9' H10H 109.5 . . ?
C7' C9' H10I 109.5 . . ?
H10G C9' H10I 109.5 . . ?
H10H C9' H10I 109.5 . . ?

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
C2' N3' C3' C4' 179.8(3) . . . . ?
C6' N3' C3' C4' 0.9(4) . . . . ?
C2' N3' C3' C10' -1.8(5) . . . . ?
C6' N3' C3' C10' 179.3(3) . . . . ?
C11' C10' C3' C4' -36.9(6) . . . . ?
C12' C10' C3' C4' 94.6(5) . . . . ?
C11' C10' C3' N3' 144.9(5) . . . . ?
C12' C10' C3' N3' -83.6(4) . . . . ?
C3' N3' C2' C1' -178.5(3) . . . . ?
C6' N3' C2' C1' 0.4(3) . . . . ?
N3' C2' C1' N1' -0.4(4) . . . . ?
C3' N3' C6' N1' 178.7(3) . . . . ?
C2' N3' C6' N1' -0.4(3) . . . . ?
C3' N3' C6' N2' -1.9(4) . . . . ?
C2' N3' C6' N2' 179.0(3) . . . . ?
N2' C6' N1' C1' -179.2(3) . . . . ?
N3' C6' N1' C1' 0.1(4) . . . . ?
C2' C1' N1' C6' 0.2(5) . . . . ?
N1' C6' N2' C5' -179.3(3) . . . . ?
N3' C6' N2' C5' 1.4(4) . . . . ?
C6' N2' C5' C4' 0.0(5) . . . . ?
C6' N2' C5' C7' -178.9(3) . . . . ?
N3' C3' C4' C5' 0.4(5) . . . . ?
C10' C3' C4' C5' -177.9(3) . . . . ?
N2' C5' C4' C3' -0.9(5) . . . . ?
C7' C5' C4' C3' 178.0(4) . . . . ?
N2' C5' C7' C8' -56.1(8) . . . . ?
C4' C5' C7' C8' 125.0(7) . . . . ?
N2' C5' C7' C9' 79.7(8) . . . . ?
C4' C5' C7' C9' -99.2(7) . . . . ?
C6 N1 C1 C2 -0.4(4) . . . . ?
C1 N1 C6 N3 -178.8(3) . . . . ?
C1 N1 C6 N2 0.9(3) . . . . ?
C3 N2 C6 N1 179.7(3) . . . . ?
C2 N2 C6 N1 -1.1(3) . . . . ?
C3 N2 C6 N3 -0.6(4) . . . . ?
C2 N2 C6 N3 178.6(3) . . . . ?
N1 C6 N3 C5 -180.0(3) . . . . ?
N2 C6 N3 C5 0.3(4) . . . . ?
C6 N3 C5 C4 0.5(5) . . . . ?
C6 N3 C5 C7 179.7(3) . . . . ?
C9 C7 C5 N3 -87.8(6) . . . . ?
C8 C7 C5 N3 41.5(6) . . . . ?
C9 C7 C5 C4 91.4(6) . . . . ?
C8 C7 C5 C4 -139.3(5) . . . . ?
C2 N2 C3 C4 -179.1(3) . . . . ?
C6 N2 C3 C4 -0.1(4) . . . . ?
C2 N2 C3 C10 2.8(5) . . . . ?
C6 N2 C3 C10 -178.2(3) . . . . ?
N2 C3 C4 C5 0.9(5) . . . . ?
C10 C3 C4 C5 178.8(3) . . . . ?
N3 C5 C4 C3 -1.2(5) . . . . ?
C7 C5 C4 C3 179.6(3) . . . . ?
C4 C3 C10 C12 29.3(5) . . . . ?
N2 C3 C10 C12 -152.8(3) . . . . ?
C4 C3 C10 C11 -98.4(4) . . . . ?
N2 C3 C10 C11 79.5(4) . . . . ?
N1 C1 C2 N2 -0.3(4) . . . . ?
C3 N2 C2 C1 179.9(3) . . . . ?
C6 N2 C2 C1 0.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 979222'
