# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1407822'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 N6 O'
_chemical_formula_weight         240.23

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_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                   7.1366(3)
_cell_length_b                   16.9882(6)
_cell_length_c                   9.4410(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.008(2)
_cell_angle_gamma                90.00
_cell_volume                     1061.20(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2157
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      25.88

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_T_max  0.712
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            8967
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2437
_reflns_number_gt                1625
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0444P)²+0.1523P] 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     SHELXL
_refine_ls_extinction_coef       0.0017(1)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2404
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.0917
_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 0.90557(17) 1.05971(7) 0.15107(13) 0.0375(3) Uani 1 1 d . . .
C2 C 0.8361(2) 0.98788(9) 0.12364(16) 0.0358(3) Uani 1 1 d . . .
C3 C 0.7049(2) 0.97001(8) -0.03383(16) 0.0352(3) Uani 1 1 d . . .
N2 N 1.02191(19) 1.07970(8) 0.29369(15) 0.0433(3) Uani 1 1 d . . .
N3 N 1.06212(19) 1.20896(7) 0.21021(15) 0.0444(3) Uani 1 1 d . . .
H2 H 0.9800 1.2048 0.1167 0.053 Uiso 1 1 calc R . .
C8 C 0.6291(2) 0.89345(9) -0.07085(17) 0.0393(4) Uani 1 1 d . . .
C11 C 1.1003(2) 1.15354(9) 0.31621(16) 0.0389(4) Uani 1 1 d . . .
C1 C 0.8845(2) 0.92534(9) 0.24079(18) 0.0425(4) Uani 1 1 d . . .
C7 C 0.5009(2) 0.87637(10) -0.21959(19) 0.0490(4) Uani 1 1 d . . .
H6 H 0.4517 0.8254 -0.2444 0.059 Uiso 1 1 calc R . .
C10 C 0.8018(3) 0.84866(10) 0.19144(19) 0.0526(4) Uani 1 1 d . . .
H8 H 0.8309 0.8080 0.2624 0.063 Uiso 1 1 calc R . .
N6 N 1.2313(2) 1.18000(8) 0.44629(14) 0.0492(4) Uani 1 1 d . . .
C4 C 0.6478(2) 1.02722(9) -0.14769(17) 0.0429(4) Uani 1 1 d . . .
H3 H 0.6967 1.0783 -0.1246 0.051 Uiso 1 1 calc R . .
C9 C 0.6847(3) 0.83415(10) 0.0469(2) 0.0505(4) Uani 1 1 d . . .
H7 H 0.6363 0.7832 0.0204 0.061 Uiso 1 1 calc R . .
C5 C 0.5199(2) 1.00906(11) -0.29403(18) 0.0507(4) Uani 1 1 d . . .
H4 H 0.4831 1.0478 -0.3691 0.061 Uiso 1 1 calc R . .
C6 C 0.4459(2) 0.93330(11) -0.33006(19) 0.0532(5) Uani 1 1 d . . .
H5 H 0.3591 0.9212 -0.4290 0.064 Uiso 1 1 calc R . .
N4 N 1.1739(2) 1.27283(8) 0.27386(16) 0.0552(4) Uani 1 1 d . . .
N5 N 1.2729(2) 1.25431(8) 0.41425(16) 0.0540(4) Uani 1 1 d . . .
O1 O 0.99265(18) 0.93869(7) 0.37598(13) 0.0583(4) Uani 1 1 d . . .
H1 H 1.055(3) 1.0429(12) 0.370(2) 0.077(6) Uiso 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
N1 C2 1.3060(18) . ?
N1 N2 1.3341(16) . ?
C2 C3 1.4615(19) . ?
C2 C1 1.478(2) . ?
C3 C4 1.392(2) . ?
C3 C8 1.402(2) . ?
N2 C11 1.3574(19) . ?
N2 H1 0.912(19) . ?
N3 C11 1.3257(18) . ?
N3 N4 1.3473(17) . ?
N3 H2 0.8600 . ?
C8 C7 1.389(2) . ?
C8 C9 1.441(2) . ?
C11 N6 1.3130(18) . ?
C1 O1 1.2401(17) . ?
C1 C10 1.434(2) . ?
C7 C6 1.368(2) . ?
C7 H6 0.9300 . ?
C10 C9 1.329(2) . ?
C10 H8 0.9300 . ?
N6 N5 1.3565(19) . ?
C4 C5 1.375(2) . ?
C4 H3 0.9300 . ?
C9 H7 0.9300 . ?
C5 C6 1.384(2) . ?
C5 H4 0.9300 . ?
C6 H5 0.9300 . ?
N4 N5 1.2857(18) . ?

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
C2 N1 N2 118.97(12) . . ?
N1 C2 C3 116.54(13) . . ?
N1 C2 C1 123.94(13) . . ?
C3 C2 C1 119.52(13) . . ?
C4 C3 C8 118.78(14) . . ?
C4 C3 C2 122.07(14) . . ?
C8 C3 C2 119.13(13) . . ?
N1 N2 C11 117.22(13) . . ?
N1 N2 H1 119.9(13) . . ?
C11 N2 H1 122.7(13) . . ?
C11 N3 N4 108.38(13) . . ?
C11 N3 H2 125.8 . . ?
N4 N3 H2 125.8 . . ?
C7 C8 C3 119.49(14) . . ?
C7 C8 C9 121.35(15) . . ?
C3 C8 C9 119.16(14) . . ?
N6 C11 N3 109.62(14) . . ?
N6 C11 N2 124.76(14) . . ?
N3 C11 N2 125.58(14) . . ?
O1 C1 C10 121.48(14) . . ?
O1 C1 C2 121.30(14) . . ?
C10 C1 C2 117.23(14) . . ?
C6 C7 C8 121.01(16) . . ?
C6 C7 H6 119.5 . . ?
C8 C7 H6 119.5 . . ?
C9 C10 C1 121.73(15) . . ?
C9 C10 H8 119.1 . . ?
C1 C10 H8 119.1 . . ?
C11 N6 N5 104.39(12) . . ?
C5 C4 C3 120.74(15) . . ?
C5 C4 H3 119.6 . . ?
C3 C4 H3 119.6 . . ?
C10 C9 C8 123.21(15) . . ?
C10 C9 H7 118.4 . . ?
C8 C9 H7 118.4 . . ?
C4 C5 C6 120.25(16) . . ?
C4 C5 H4 119.9 . . ?
C6 C5 H4 119.9 . . ?
C7 C6 C5 119.74(15) . . ?
C7 C6 H5 120.1 . . ?
C5 C6 H5 120.1 . . ?
N5 N4 N3 105.51(13) . . ?
N4 N5 N6 112.09(12) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.034
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1407823'
_audit_update_record             
;
2016-07-24 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_audit_creation_date             2016-07-24
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.09.16 svn.r3215 for OlexSys, GUI svn.r5095)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H7 N5 O'
_chemical_formula_sum            'C12 H7 N5 O'
_chemical_formula_weight         237.23
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.7787(3)
_cell_length_b                   15.4361(13)
_cell_length_c                   17.0098(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.735(6)
_cell_angle_gamma                90
_cell_volume                     991.02(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2003
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.8545
_cell_measurement_theta_min      2.3945
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0640 before and 0.0311 after correction.
The Ratio of minimum to maximum transmission is 0.7005.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488.0
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14370
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_min         1.782
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1106
_reflns_number_total             2280
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2259
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0658P)²+0.0340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1400
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1-H1A
 0.8 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C11(H11), C6(H6), C5(H5), C1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
N1 N 0.5315(5) 0.19222(12) 0.96599(10) 0.0458(5) Uani 1 1 d . . . . .
N3 N 0.8347(6) 0.17201(14) 1.07830(12) 0.0571(6) Uani 1 1 d . . . . .
N2 N 0.5846(6) 0.10567(13) 0.96936(12) 0.0594(6) Uani 1 1 d . . . . .
N4 N 0.6648(5) 0.31737(12) 1.04367(10) 0.0475(5) Uani 1 1 d . . . . .
N5 N 0.4972(5) 0.36548(12) 0.99029(10) 0.0452(5) Uani 1 1 d . . . . .
C8 C 0.1793(5) 0.38561(15) 0.86624(12) 0.0400(6) Uani 1 1 d . . . . .
C3 C 0.3491(5) 0.32865(14) 0.92320(11) 0.0387(5) Uani 1 1 d . . . . .
C4 C 0.3614(6) 0.23990(15) 0.90756(12) 0.0430(6) Uani 1 1 d . . . . .
C9 C 0.1576(5) 0.47488(15) 0.87674(12) 0.0426(6) Uani 1 1 d . . . . .
H9 H 0.2504 0.5000 0.9229 0.051 Uiso 1 1 calc R . . . .
C12 C -0.1310(6) 0.40172(17) 0.73850(13) 0.0500(6) Uani 1 1 d . . . . .
H12 H -0.2307 0.3778 0.6924 0.060 Uiso 1 1 calc R . . . .
C11 C -0.1461(6) 0.48831(16) 0.74944(13) 0.0509(7) Uani 1 1 d . . . . .
H11 H -0.2535 0.5233 0.7107 0.061 Uiso 1 1 calc R . . . .
C6 C 0.0550(6) 0.25684(15) 0.78432(13) 0.0503(7) Uani 1 1 d . . . . .
H6 H -0.0438 0.2332 0.7380 0.060 Uiso 1 1 calc R . . . .
C10 C -0.0007(6) 0.52593(16) 0.81896(12) 0.0451(6) Uani 1 1 d . . . . .
C7 C 0.0331(6) 0.34692(15) 0.79563(11) 0.0416(6) Uani 1 1 d . . . . .
C2 C 0.6810(6) 0.23101(15) 1.03171(12) 0.0451(6) Uani 1 1 d . . . . .
C5 C 0.2150(6) 0.20287(16) 0.83848(13) 0.0514(7) Uani 1 1 d . . . . .
H5 H 0.2265 0.1435 0.8298 0.062 Uiso 1 1 calc R . . . .
C1 C 0.7653(7) 0.09873(17) 1.03803(16) 0.0638(8) Uani 1 1 d . . . . .
H1 H 0.8407 0.0452 1.0574 0.077 Uiso 1 1 calc R . . . .
O1 O -0.0282(5) 0.61255(11) 0.82465(10) 0.0625(6) Uani 1 1 d D . . . .
H1A H 0.066(8) 0.6330(17) 0.8682(12) 0.093(10) 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
N1 N2 1.352(2) . ?
N1 C4 1.372(3) . ?
N1 C2 1.367(3) . ?
N3 C2 1.323(3) . ?
N3 C1 1.342(3) . ?
N2 C1 1.329(3) . ?
N4 N5 1.312(2) . ?
N4 C2 1.350(3) . ?
N5 C3 1.370(2) . ?
C8 C3 1.437(3) . ?
C8 C9 1.392(3) . ?
C8 C7 1.429(3) . ?
C3 C4 1.397(3) . ?
C4 C5 1.397(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.351(3) . ?
C12 C7 1.409(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.406(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.407(3) . ?
C6 C5 1.362(3) . ?
C10 O1 1.345(3) . ?
C5 H5 0.9300 . ?
C1 H1 0.9300 . ?
O1 H1A 0.867(17) . ?

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 C4 128.64(19) . . ?
N2 N1 C2 110.10(18) . . ?
C2 N1 C4 121.3(2) . . ?
C2 N3 C1 101.83(19) . . ?
C1 N2 N1 100.71(19) . . ?
N5 N4 C2 118.58(18) . . ?
N4 N5 C3 120.39(19) . . ?
C9 C8 C3 123.12(18) . . ?
C9 C8 C7 119.9(2) . . ?
C7 C8 C3 117.0(2) . . ?
N5 C3 C8 117.3(2) . . ?
N5 C3 C4 123.3(2) . . ?
C4 C3 C8 119.32(19) . . ?
N1 C4 C3 114.01(19) . . ?
N1 C4 C5 122.9(2) . . ?
C3 C4 C5 123.1(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C7 121.3(2) . . ?
C7 C12 H12 119.4 . . ?
C12 C11 H11 119.8 . . ?
C12 C11 C10 120.5(2) . . ?
C10 C11 H11 119.8 . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C5 C6 C7 122.6(2) . . ?
C9 C10 C11 120.3(2) . . ?
O1 C10 C9 123.4(2) . . ?
O1 C10 C11 116.3(2) . . ?
C12 C7 C8 117.9(2) . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 C12 121.7(2) . . ?
N3 C2 N1 109.9(2) . . ?
N3 C2 N4 127.7(2) . . ?
N4 C2 N1 122.4(2) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 C4 117.6(2) . . ?
C6 C5 H5 121.2 . . ?
N3 C1 H1 121.3 . . ?
N2 C1 N3 117.4(2) . . ?
N2 C1 H1 121.3 . . ?
C10 O1 H1A 113.2(19) . . ?

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 N2 C1 N3 -0.5(3) . . . . ?
N1 C4 C5 C6 -179.5(2) . . . . ?
N2 N1 C4 C3 179.2(2) . . . . ?
N2 N1 C4 C5 -1.1(4) . . . . ?
N2 N1 C2 N3 0.5(3) . . . . ?
N2 N1 C2 N4 -179.5(2) . . . . ?
N4 N5 C3 C8 -178.11(19) . . . . ?
N4 N5 C3 C4 0.8(3) . . . . ?
N5 N4 C2 N1 0.4(3) . . . . ?
N5 N4 C2 N3 -179.6(2) . . . . ?
N5 C3 C4 N1 0.8(3) . . . . ?
N5 C3 C4 C5 -178.9(2) . . . . ?
C8 C3 C4 N1 179.68(19) . . . . ?
C8 C3 C4 C5 -0.1(3) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C8 C9 C10 O1 -179.3(2) . . . . ?
C3 C8 C9 C10 178.3(2) . . . . ?
C3 C8 C7 C12 -179.2(2) . . . . ?
C3 C8 C7 C6 0.6(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 N1 N2 C1 179.1(2) . . . . ?
C4 N1 C2 N3 -178.7(2) . . . . ?
C4 N1 C2 N4 1.2(3) . . . . ?
C9 C8 C3 N5 -0.5(3) . . . . ?
C9 C8 C3 C4 -179.5(2) . . . . ?
C9 C8 C7 C12 -0.1(3) . . . . ?
C9 C8 C7 C6 179.7(2) . . . . ?
C12 C11 C10 C9 -0.2(4) . . . . ?
C12 C11 C10 O1 180.0(2) . . . . ?
C11 C12 C7 C8 0.8(3) . . . . ?
C11 C12 C7 C6 -179.0(2) . . . . ?
C7 C8 C3 N5 178.54(19) . . . . ?
C7 C8 C3 C4 -0.4(3) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C7 C12 C11 C10 -0.7(4) . . . . ?
C7 C6 C5 C4 0.0(4) . . . . ?
C2 N1 N2 C1 0.0(3) . . . . ?
C2 N1 C4 C3 -1.8(3) . . . . ?
C2 N1 C4 C5 178.0(2) . . . . ?
C2 N3 C1 N2 0.8(3) . . . . ?
C2 N4 N5 C3 -1.4(3) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C5 C6 C7 C12 179.4(2) . . . . ?
C1 N3 C2 N1 -0.7(3) . . . . ?
C1 N3 C2 N4 179.3(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
