# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14
_database_code_depnum_ccdc_archive 'CCDC 1526952'
_audit_update_record             
;
2017-01-12 deposited with the CCDC.
2017-07-26 downloaded from the CCDC.
;
#=====================================================================  

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        C9N3O2H7
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 N3 O2'
_chemical_formula_sum            'C9 H7 N3 O2'
_chemical_formula_weight         189.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.8058(2)
_cell_length_b                   5.4704(3)
_cell_length_c                   31.7944(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.687(4)
_cell_angle_gamma                90
_cell_volume                     835.80(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2276
_cell_measurement_theta_min      4.1683
_cell_measurement_theta_max      66.4684

_exptl_crystal_description       flake
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.929
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.752
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      297.09(10)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3503
_diffrn_reflns_number            4779
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         4.1683
_diffrn_reflns_theta_max         66.4684
_diffrn_reflns_theta_full        66.4915
_diffrn_measured_fraction_theta_max 0.9880
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             1488
_reflns_number_gt                1296
_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 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXL-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)+(0.0949P)²+0.0666P]
 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     SHELXL
_refine_ls_extinction_coef       0.036(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1488
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1359
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_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
O1 O 0.1328(2) -0.1191(2) 0.45349(4) 0.0549(4) Uani 1 1 d . . . . .
H1A H 0.0207 -0.1344 0.4725 0.082 Uiso 1 1 calc R U . . .
O2 O 0.2416(2) 0.2169(2) 0.48987(3) 0.0553(4) Uani 1 1 d . . . . .
N1 N 1.0296(2) 0.3356(2) 0.33088(4) 0.0397(4) Uani 1 1 d . . . . .
C8 C 1.1322(4) 0.2002(3) 0.29941(5) 0.0498(4) Uani 1 1 d . . . . .
H8A H 1.0957 0.0365 0.2936 0.060 Uiso 1 1 calc R U . . .
C9 C 1.3004(4) 0.3537(3) 0.27789(5) 0.0526(5) Uani 1 1 d . . . . .
H9A H 1.4020 0.3129 0.2542 0.063 Uiso 1 1 calc R U . . .
C1 C 0.2704(3) 0.0787(3) 0.45874(5) 0.0411(4) Uani 1 1 d . . . . .
C2 C 0.4722(3) 0.1439(3) 0.42574(4) 0.0390(4) Uani 1 1 d . . . . .
C3 C 0.5029(3) -0.0051(3) 0.39070(5) 0.0440(4) Uani 1 1 d . . . . .
H3A H 0.3981 -0.1474 0.3883 0.053 Uiso 1 1 calc R U . . .
C4 C 0.6873(3) 0.0561(3) 0.35951(5) 0.0437(4) Uani 1 1 d . . . . .
H4A H 0.7077 -0.0441 0.3361 0.052 Uiso 1 1 calc R U . . .
C5 C 0.8418(3) 0.2691(3) 0.36350(5) 0.0374(4) Uani 1 1 d . . . . .
C6 C 0.8168(3) 0.4175(3) 0.39847(5) 0.0439(4) Uani 1 1 d . . . . .
H6A H 0.9241 0.5582 0.4011 0.053 Uiso 1 1 calc R U . . .
C7 C 0.6306(3) 0.3545(3) 0.42945(5) 0.0441(4) Uani 1 1 d . . . . .
H7A H 0.6116 0.4542 0.4529 0.053 Uiso 1 1 calc R U . . .
N4 N 1.1313(4) 0.5650(3) 0.32891(5) 0.0599(5) Uani 1 1 d . . . . .
N5 N 1.2960(4) 0.5747(3) 0.29646(5) 0.0620(5) 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
O1 C1 1.2777(18) . ?
O1 H1A 0.8200 . ?
O2 C1 1.2547(19) . ?
N1 C8 1.3434(19) . ?
N1 N4 1.3485(18) . ?
N1 C5 1.4300(18) . ?
C8 C9 1.357(2) . ?
C8 H8A 0.9300 . ?
C9 N5 1.346(2) . ?
C9 H9A 0.9300 . ?
C1 C2 1.481(2) . ?
C2 C7 1.385(2) . ?
C2 C3 1.390(2) . ?
C3 C4 1.379(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.387(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.383(2) . ?
C6 C7 1.382(2) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
N4 N5 1.309(2) . ?

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
C1 O1 H1A 109.5 . . ?
C8 N1 N4 110.01(13) . . ?
C8 N1 C5 129.82(13) . . ?
N4 N1 C5 120.17(13) . . ?
N1 C8 C9 105.10(14) . . ?
N1 C8 H8A 127.4 . . ?
C9 C8 H8A 127.4 . . ?
N5 C9 C8 108.80(14) . . ?
N5 C9 H9A 125.6 . . ?
C8 C9 H9A 125.6 . . ?
O2 C1 O1 123.48(14) . . ?
O2 C1 C2 119.54(13) . . ?
O1 C1 C2 116.98(13) . . ?
C7 C2 C3 119.50(14) . . ?
C7 C2 C1 120.27(14) . . ?
C3 C2 C1 120.23(14) . . ?
C4 C3 C2 120.62(14) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 119.10(14) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C6 C5 C4 121.01(14) . . ?
C6 C5 N1 119.71(13) . . ?
C4 C5 N1 119.29(13) . . ?
C7 C6 C5 119.34(14) . . ?
C7 C6 H6A 120.3 . . ?
C5 C6 H6A 120.3 . . ?
C6 C7 C2 120.43(14) . . ?
C6 C7 H7A 119.8 . . ?
C2 C7 H7A 119.8 . . ?
N5 N4 N1 107.30(14) . . ?
N4 N5 C9 108.79(14) . . ?

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
N4 N1 C8 C9 -0.1(2) . . . . ?
C5 N1 C8 C9 -179.83(14) . . . . ?
N1 C8 C9 N5 0.0(2) . . . . ?
O2 C1 C2 C7 0.8(2) . . . . ?
O1 C1 C2 C7 -179.45(14) . . . . ?
O2 C1 C2 C3 -178.84(14) . . . . ?
O1 C1 C2 C3 0.9(2) . . . . ?
C7 C2 C3 C4 -0.6(2) . . . . ?
C1 C2 C3 C4 179.02(14) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C6 1.1(2) . . . . ?
C3 C4 C5 N1 -178.89(13) . . . . ?
C8 N1 C5 C6 164.01(16) . . . . ?
N4 N1 C5 C6 -15.7(2) . . . . ?
C8 N1 C5 C4 -16.0(2) . . . . ?
N4 N1 C5 C4 164.28(15) . . . . ?
C4 C5 C6 C7 -1.3(2) . . . . ?
N1 C5 C6 C7 178.69(13) . . . . ?
C5 C6 C7 C2 0.5(2) . . . . ?
C3 C2 C7 C6 0.4(2) . . . . ?
C1 C2 C7 C6 -179.23(14) . . . . ?
C8 N1 N4 N5 0.2(2) . . . . ?
C5 N1 N4 N5 179.93(14) . . . . ?
N1 N4 N5 C9 -0.2(2) . . . . ?
C8 C9 N5 N4 0.1(2) . . . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-2


_chemical_properties_physical    ', Photo-sensitive'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_14_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1537756'
_audit_update_record             
;
2017-03-17 deposited with the CCDC.
2017-07-26 downloaded from the CCDC.
;
#=====================================================================

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          156
_chemical_formula_moiety         'C10 H9 N3 O'
_chemical_formula_sum            'C10 H9 N3 O'
_chemical_formula_weight         187.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.0343(6)
_cell_length_b                   20.902(3)
_cell_length_c                   10.871(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.641(17)
_cell_angle_gamma                90
_cell_volume                     910.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294.6(10)
_cell_measurement_reflns_used    1145
_cell_measurement_theta_min      4.2030
_cell_measurement_theta_max      71.7830

_exptl_crystal_description       flake
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   0.977
_exptl_transmission_factor_max   0.993
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.759
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      294.6(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3503
_diffrn_reflns_number            5216
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.949
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1807
_reflns_number_gt                757
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXS-2013 (Sheldrick, 2013)'
_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     
;
 w=1/[σ²(Fo²)+(0.2000P)²]
 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     SHELXL
_refine_ls_extinction_coef       0.000(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1807
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2006
_refine_ls_R_factor_gt           0.1565
_refine_ls_wR_factor_ref         0.4744
_refine_ls_wR_factor_gt          0.4220
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_restrained_S_all      1.221
_refine_ls_shift/su_max          0.062
_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
O1 O 0.7359(16) 0.6779(3) -0.3986(7) 0.130(2) Uani 1 1 d . . . . .
N1 N 0.0410(18) 0.5842(4) 0.2845(8) 0.119(2) Uani 1 1 d . . . . .
N2 N 0.1341(19) 0.5722(3) 0.1840(7) 0.115(2) Uani 1 1 d . . . . .
N3 N 0.1925(12) 0.62736(19) 0.1183(6) 0.0881(18) Uani 1 1 d . . . . .
C1 C 0.031(2) 0.6536(4) 0.2950(7) 0.111(2) Uani 1 1 d . . . . .
H1A H -0.0207 0.6762 0.3639 0.133 Uiso 1 1 calc R U . . .
C2 C 0.107(2) 0.6793(3) 0.1914(8) 0.108(2) Uani 1 1 d . . . . .
H2A H 0.1052 0.7225 0.1707 0.130 Uiso 1 1 calc R U . . .
C3 C 0.3009(14) 0.6285(2) 0.0047(6) 0.0771(16) Uani 1 1 d . . . . .
C4 C 0.2941(14) 0.5718(2) -0.0614(7) 0.092(2) Uani 1 1 d . . . . .
H4A H 0.2178 0.5341 -0.0289 0.110 Uiso 1 1 calc R U . . .
C5 C 0.4047(14) 0.5729(3) -0.1778(7) 0.0897(19) Uani 1 1 d . . . . .
H5A H 0.3966 0.5348 -0.2223 0.108 Uiso 1 1 calc R U . . .
C6 C 0.5277(12) 0.6273(2) -0.2329(6) 0.0789(18) Uani 1 1 d . . . . .
C7 C 0.5250(18) 0.6841(3) -0.1584(9) 0.102(2) Uani 1 1 d . . . . .
H7A H 0.5964 0.7225 -0.1895 0.123 Uiso 1 1 calc R U . . .
C8 C 0.4208(17) 0.6832(3) -0.0436(8) 0.099(2) Uani 1 1 d . . . . .
H8A H 0.4314 0.7206 0.0030 0.119 Uiso 1 1 calc R U . . .
C9 C 0.6398(16) 0.6307(3) -0.3500(8) 0.0913(19) Uani 1 1 d . . . . .
C10 C 0.651(2) 0.5730(4) -0.4246(9) 0.134(3) Uani 1 1 d . . . . .
H10A H 0.5714 0.5374 -0.3808 0.200 Uiso 1 1 calc R U . . .
H10B H 0.8769 0.5651 -0.4403 0.200 Uiso 1 1 calc R U . . .
H10C H 0.5128 0.5786 -0.5018 0.200 Uiso 1 1 calc R U . . .


_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 C9 1.205(7) . ?
N1 N2 1.222(9) . ?
N1 C1 1.456(11) . ?
N2 N3 1.391(8) . ?
N3 C3 1.357(8) . ?
N3 C2 1.411(8) . ?
C1 C2 1.315(11) . ?
C1 H1A 0.9300 . ?
C2 H2A 0.9300 . ?
C3 C8 1.369(8) . ?
C3 C4 1.386(8) . ?
C4 C5 1.389(10) . ?
C4 H4A 0.9300 . ?
C5 C6 1.403(8) . ?
C5 H5A 0.9300 . ?
C6 C9 1.401(10) . ?
C6 C7 1.437(9) . ?
C7 C8 1.363(11) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
C9 C10 1.455(10) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
N2 N1 C1 106.8(7) . . ?
N1 N2 N3 112.1(6) . . ?
C3 N3 N2 125.0(5) . . ?
C3 N3 C2 128.6(5) . . ?
N2 N3 C2 106.4(6) . . ?
C2 C1 N1 109.2(7) . . ?
C2 C1 H1A 125.4 . . ?
N1 C1 H1A 125.4 . . ?
C1 C2 N3 105.3(7) . . ?
C1 C2 H2A 127.3 . . ?
N3 C2 H2A 127.3 . . ?
N3 C3 C8 122.0(6) . . ?
N3 C3 C4 117.9(5) . . ?
C8 C3 C4 120.2(7) . . ?
C3 C4 C5 118.0(5) . . ?
C3 C4 H4A 121.0 . . ?
C5 C4 H4A 121.0 . . ?
C4 C5 C6 124.6(6) . . ?
C4 C5 H5A 117.7 . . ?
C6 C5 H5A 117.7 . . ?
C9 C6 C5 126.5(6) . . ?
C9 C6 C7 119.7(5) . . ?
C5 C6 C7 113.8(7) . . ?
C8 C7 C6 121.9(6) . . ?
C8 C7 H7A 119.0 . . ?
C6 C7 H7A 119.0 . . ?
C7 C8 C3 121.5(6) . . ?
C7 C8 H8A 119.3 . . ?
C3 C8 H8A 119.3 . . ?
O1 C9 C6 126.3(7) . . ?
O1 C9 C10 113.7(8) . . ?
C6 C9 C10 119.9(6) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_refine_diff_density_max         0.604
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.078

_shelxl_version_number           2013-2

