# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


#######################################################################
#
#                 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_ia2311_0m
_database_code_depnum_ccdc_archive 'CCDC 887676'
#TrackingRef '12029_web_deposit_cif_file_0_IvanAprahamian_1340204718.triazolopyridinium-2a.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H14 N3 O2, Cl O4'
_chemical_formula_sum            'C15 H14 Cl N3 O6'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      173(2)
_chemical_formula_weight         367.74

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  'P 2yn'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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                   13.7923(7)
_cell_length_b                   5.9508(3)
_cell_length_c                   19.9335(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.5400(10)
_cell_angle_gamma                90.00
_cell_volume                     1608.44(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      25.34
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8758
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop
using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data
were measured using omega and phi scans of 0.5\% per frame
for 30 s. The total number of images were based on
results from the program COSMO where redundancy was expected to be 4 and
completeness to 0.83\%A to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which
corrects for Lp. Scaling and absorption corrections were applied using SADABS6
multi-scan technique, supplied by George Sheldrick. The structures are solved
by the direct method using the SHELXS-97 program and refined by least squares
method on F2, SHELXL-97, incorporated in SHELXTL-PC V 6.14.

All H atoms were placed in calculated positions and refined using a riding
model.
C-H(aromatic) = 0.94 \%A and Uiso(H) = 1.2Ueq(C)
C-H (alaphatic) = 0.99 \%A and Uiso(H) = 1.2Ueq(C)
CH2 = 0.98 \%A and Uiso(H) = 1.2Ueq(C)
CH3 = 0.97\%A and Uiso(H) = 1.5Ueq(C)
N-H = 0.86 (0.92)\%A and Uiso(H) = 1.2 Ueq(N)
O-H(alcohol) = 0.85\%Aand Uiso(H) = 1.2Ueq(O)
O-H(acid) = 0.82\%A and Uiso(H) = 1.5Ueq(O)
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w,and/f 0.5 deg'
_diffrn_detector_area_resol_mean 836.6
_diffrn_reflns_number            24909
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.39
_reflns_number_total             2947
_reflns_number_gt                2544
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_cell_refinement       'APEX2 (BRUKER, V2010.11-3, 2010)'
_computing_data_reduction        'SAINT (BRUKER, V7.68A, 2010)'
_computing_structure_solution    
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_refinement  
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0623P)^2^+1.1166P] where P=(Fo^2^+2Fc^2^)/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         2947
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.03898(10) 1.0731(2) 0.23093(7) 0.0351(3) Uani 1 1 d . . .
O2 O 0.90126(10) 1.2722(2) 0.23570(7) 0.0353(3) Uani 1 1 d . . .
N1 N 0.79625(12) 0.8874(3) 0.17200(8) 0.0308(4) Uani 1 1 d . . .
N2 N 0.77457(11) 0.7016(3) 0.13594(8) 0.0297(4) Uani 1 1 d . . .
N3 N 0.85734(11) 0.6110(3) 0.11844(8) 0.0263(3) Uani 1 1 d . . .
C1 C 0.89248(14) 0.9192(3) 0.17825(9) 0.0282(4) Uani 1 1 d . . .
C2 C 0.93506(13) 0.7460(3) 0.14468(9) 0.0269(4) Uani 1 1 d . . .
C3 C 1.02877(14) 0.6910(4) 0.13202(10) 0.0340(5) Uani 1 1 d . . .
H3 H 1.0843 0.7828 0.1488 0.041 Uiso 1 1 calc R . .
C4 C 1.03829(15) 0.5023(4) 0.09503(11) 0.0370(5) Uani 1 1 d . . .
H4 H 1.1014 0.4605 0.0866 0.044 Uiso 1 1 calc R . .
C5 C 0.95574(15) 0.3688(4) 0.06917(10) 0.0341(5) Uani 1 1 d . . .
H5 H 0.9642 0.2375 0.0437 0.041 Uiso 1 1 calc R . .
C6 C 0.86413(15) 0.4235(3) 0.07982(10) 0.0296(4) Uani 1 1 d . . .
H6 H 0.8078 0.3363 0.0614 0.036 Uiso 1 1 calc R . .
C7 C 0.94275(14) 1.1106(3) 0.21811(9) 0.0286(4) Uani 1 1 d . . .
C8 C 1.10148(15) 1.2368(4) 0.27309(11) 0.0378(5) Uani 1 1 d . . .
H8A H 1.0741 1.2730 0.3144 0.045 Uiso 1 1 calc R . .
H8B H 1.1059 1.3772 0.2472 0.045 Uiso 1 1 calc R . .
C9 C 1.20051(17) 1.1312(5) 0.29231(15) 0.0545(7) Uani 1 1 d . . .
H9A H 1.1941 0.9864 0.3145 0.082 Uiso 1 1 calc R . .
H9B H 1.2437 1.2302 0.3238 0.082 Uiso 1 1 calc R . .
H9C H 1.2289 1.1076 0.2512 0.082 Uiso 1 1 calc R . .
C10 C 0.67963(14) 0.5937(3) 0.12426(10) 0.0309(4) Uani 1 1 d . . .
C11 C 0.60085(15) 0.7056(4) 0.08621(11) 0.0413(5) Uani 1 1 d . . .
H11 H 0.6088 0.8473 0.0660 0.050 Uiso 1 1 calc R . .
C12 C 0.50869(17) 0.6009(5) 0.07872(12) 0.0555(7) Uani 1 1 d . . .
H12 H 0.4522 0.6735 0.0536 0.067 Uiso 1 1 calc R . .
C13 C 0.49915(18) 0.3922(5) 0.10766(14) 0.0572(7) Uani 1 1 d . . .
H13 H 0.4363 0.3221 0.1016 0.069 Uiso 1 1 calc R . .
C14 C 0.57951(17) 0.2856(4) 0.14496(13) 0.0494(6) Uani 1 1 d . . .
H14 H 0.5721 0.1424 0.1645 0.059 Uiso 1 1 calc R . .
C15 C 0.67142(16) 0.3868(4) 0.15419(11) 0.0377(5) Uani 1 1 d . . .
H15 H 0.7274 0.3157 0.1805 0.045 Uiso 1 1 calc R . .
Cl1 Cl 0.22960(4) 0.09354(9) 0.04357(3) 0.03841(18) Uani 1 1 d . . .
O3 O 0.25645(13) 0.3211(3) 0.03537(10) 0.0574(5) Uani 1 1 d . A .
O4 O 0.2833(3) -0.0658(7) 0.0169(3) 0.0624(13) Uani 0.50 1 d P A 1
O6 O 0.1280(2) 0.0812(6) 0.0050(2) 0.0444(9) Uani 0.50 1 d P A 1
O5 O 0.2225(5) 0.0758(9) 0.11197(18) 0.0762(19) Uani 0.50 1 d P A 1
O4A O 0.3184(5) -0.0122(15) 0.0721(8) 0.199(6) Uani 0.50 1 d P A 2
O5A O 0.2094(17) 0.0151(17) -0.0192(3) 0.311(11) Uani 0.50 1 d P A 2
O6A O 0.1622(9) 0.0335(13) 0.0760(9) 0.214(7) Uani 0.50 1 d P A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0285(7) 0.0367(8) 0.0387(8) -0.0096(6) 0.0021(6) -0.0042(6)
O2 0.0361(8) 0.0305(7) 0.0383(8) -0.0049(6) 0.0037(6) 0.0017(6)
N1 0.0299(8) 0.0283(9) 0.0334(9) -0.0043(7) 0.0034(7) 0.0007(7)
N2 0.0243(8) 0.0284(8) 0.0358(9) -0.0055(7) 0.0038(6) 0.0006(6)
N3 0.0257(8) 0.0264(8) 0.0266(8) 0.0002(6) 0.0046(6) 0.0008(6)
C1 0.0280(9) 0.0288(10) 0.0271(9) 0.0010(7) 0.0033(7) 0.0003(8)
C2 0.0278(9) 0.0276(9) 0.0244(9) 0.0015(7) 0.0021(7) -0.0017(8)
C3 0.0276(10) 0.0391(11) 0.0353(10) -0.0020(9) 0.0053(8) -0.0014(8)
C4 0.0332(10) 0.0417(12) 0.0381(11) -0.0021(9) 0.0117(8) 0.0043(9)
C5 0.0412(11) 0.0320(10) 0.0308(10) -0.0025(8) 0.0106(8) 0.0041(9)
C6 0.0344(10) 0.0272(10) 0.0267(9) -0.0010(8) 0.0041(8) -0.0011(8)
C7 0.0307(10) 0.0293(10) 0.0253(9) 0.0011(8) 0.0035(8) -0.0024(8)
C8 0.0353(11) 0.0375(11) 0.0383(11) -0.0068(9) 0.0010(9) -0.0083(9)
C9 0.0366(12) 0.0548(15) 0.0660(16) -0.0101(13) -0.0065(11) -0.0057(11)
C10 0.0250(10) 0.0359(11) 0.0314(10) -0.0093(8) 0.0042(8) -0.0011(8)
C11 0.0334(11) 0.0555(14) 0.0340(11) -0.0084(10) 0.0036(9) 0.0062(10)
C12 0.0281(11) 0.094(2) 0.0414(13) -0.0217(14) -0.0016(9) 0.0113(12)
C13 0.0363(13) 0.080(2) 0.0583(15) -0.0329(15) 0.0158(11) -0.0197(13)
C14 0.0446(13) 0.0470(14) 0.0619(15) -0.0205(12) 0.0235(12) -0.0148(11)
C15 0.0351(11) 0.0347(11) 0.0452(12) -0.0083(9) 0.0125(9) -0.0020(9)
Cl1 0.0414(3) 0.0352(3) 0.0378(3) 0.0008(2) 0.0050(2) -0.0026(2)
O3 0.0582(11) 0.0413(10) 0.0678(12) 0.0084(8) -0.0016(9) -0.0084(8)
O4 0.032(2) 0.052(2) 0.100(4) -0.029(3) 0.004(2) 0.0158(17)
O6 0.0292(16) 0.041(2) 0.058(2) 0.0009(18) -0.0054(15) -0.0093(14)
O5 0.138(5) 0.065(3) 0.0224(17) 0.0117(16) 0.006(2) -0.030(3)
O4A 0.063(4) 0.120(6) 0.402(16) 0.158(9) 0.009(6) 0.018(4)
O5A 0.71(3) 0.131(8) 0.052(4) 0.001(4) -0.040(9) -0.228(14)
O6A 0.192(9) 0.079(5) 0.45(2) 0.078(9) 0.258(13) 0.031(6)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.324(2) . ?
O1 C8 1.461(2) . ?
O2 C7 1.203(2) . ?
N1 N2 1.323(2) . ?
N1 C1 1.324(2) . ?
N2 N3 1.364(2) . ?
N2 C10 1.439(2) . ?
N3 C2 1.365(2) . ?
N3 C6 1.369(2) . ?
C1 C2 1.414(3) . ?
C1 C7 1.486(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.363(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.407(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.359(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.488(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.378(3) . ?
C10 C15 1.382(3) . ?
C11 C12 1.399(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.372(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
Cl1 O6A 1.276(6) . ?
Cl1 O5A 1.317(7) . ?
Cl1 O4 1.369(4) . ?
Cl1 O5 1.389(4) . ?
Cl1 O4A 1.401(6) . ?
Cl1 O3 1.4209(18) . ?
Cl1 O6 1.471(3) . ?

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
C7 O1 C8 117.64(15) . . ?
N2 N1 C1 107.08(15) . . ?
N1 N2 N3 110.65(15) . . ?
N1 N2 C10 124.73(15) . . ?
N3 N2 C10 124.17(15) . . ?
N2 N3 C2 107.74(15) . . ?
N2 N3 C6 127.78(16) . . ?
C2 N3 C6 124.45(16) . . ?
N1 C1 C2 110.33(16) . . ?
N1 C1 C7 121.44(17) . . ?
C2 C1 C7 128.19(17) . . ?
N3 C2 C3 118.65(17) . . ?
N3 C2 C1 104.20(16) . . ?
C3 C2 C1 137.13(18) . . ?
C4 C3 C2 118.28(19) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 120.80(19) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 121.38(19) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 N3 116.41(18) . . ?
C5 C6 H6 121.8 . . ?
N3 C6 H6 121.8 . . ?
O2 C7 O1 126.29(17) . . ?
O2 C7 C1 124.61(17) . . ?
O1 C7 C1 109.10(16) . . ?
O1 C8 C9 106.48(18) . . ?
O1 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
O1 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 123.3(2) . . ?
C11 C10 N2 118.44(19) . . ?
C15 C10 N2 118.16(18) . . ?
C10 C11 C12 117.0(2) . . ?
C10 C11 H11 121.5 . . ?
C12 C11 H11 121.5 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C10 C15 C14 118.4(2) . . ?
C10 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
O6A Cl1 O5A 109.5(10) . . ?
O6A Cl1 O4 119.9(4) . . ?
O5A Cl1 O4 54.6(9) . . ?
O6A Cl1 O5 45.0(8) . . ?
O5A Cl1 O5 149.9(5) . . ?
O4 Cl1 O5 118.0(4) . . ?
O6A Cl1 O4A 109.4(7) . . ?
O5A Cl1 O4A 104.1(11) . . ?
O4 Cl1 O4A 49.7(6) . . ?
O5 Cl1 O4A 77.3(6) . . ?
O6A Cl1 O3 123.7(4) . . ?
O5A Cl1 O3 104.0(3) . . ?
O4 Cl1 O3 116.4(2) . . ?
O5 Cl1 O3 104.6(2) . . ?
O4A Cl1 O3 104.3(3) . . ?
O6A Cl1 O6 62.5(8) . . ?
O5A Cl1 O6 58.0(10) . . ?
O4 Cl1 O6 107.1(2) . . ?
O5 Cl1 O6 106.1(3) . . ?
O4A Cl1 O6 150.2(5) . . ?
O3 Cl1 O6 103.35(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
C1 N1 N2 N3 0.0(2) . . . . ?
C1 N1 N2 C10 172.52(18) . . . . ?
N1 N2 N3 C2 0.0(2) . . . . ?
C10 N2 N3 C2 -172.56(17) . . . . ?
N1 N2 N3 C6 -178.03(17) . . . . ?
C10 N2 N3 C6 9.4(3) . . . . ?
N2 N1 C1 C2 0.0(2) . . . . ?
N2 N1 C1 C7 -177.98(16) . . . . ?
N2 N3 C2 C3 -178.42(17) . . . . ?
C6 N3 C2 C3 -0.3(3) . . . . ?
N2 N3 C2 C1 0.00(19) . . . . ?
C6 N3 C2 C1 178.12(16) . . . . ?
N1 C1 C2 N3 0.0(2) . . . . ?
C7 C1 C2 N3 177.81(17) . . . . ?
N1 C1 C2 C3 178.0(2) . . . . ?
C7 C1 C2 C3 -4.2(4) . . . . ?
N3 C2 C3 C4 -1.2(3) . . . . ?
C1 C2 C3 C4 -178.9(2) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 N3 -1.8(3) . . . . ?
N2 N3 C6 C5 179.50(17) . . . . ?
C2 N3 C6 C5 1.8(3) . . . . ?
C8 O1 C7 O2 3.1(3) . . . . ?
C8 O1 C7 C1 -176.67(16) . . . . ?
N1 C1 C7 O2 -15.5(3) . . . . ?
C2 C1 C7 O2 166.90(19) . . . . ?
N1 C1 C7 O1 164.23(17) . . . . ?
C2 C1 C7 O1 -13.4(3) . . . . ?
C7 O1 C8 C9 167.57(19) . . . . ?
N1 N2 C10 C11 65.6(3) . . . . ?
N3 N2 C10 C11 -122.9(2) . . . . ?
N1 N2 C10 C15 -111.8(2) . . . . ?
N3 N2 C10 C15 59.7(2) . . . . ?
C15 C10 C11 C12 0.4(3) . . . . ?
N2 C10 C11 C12 -176.86(18) . . . . ?
C10 C11 C12 C13 -1.2(3) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C11 C10 C15 C14 0.6(3) . . . . ?
N2 C10 C15 C14 177.90(18) . . . . ?
C13 C14 C15 C10 -0.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.050
_contact_Crystallographer_name   'Richard Staples'
_contact_Crystallographer_email  staples@chemistry.msu.com