# 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 2019

####################################################################### 
# 
# 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_bwn17023
_database_code_depnum_ccdc_archive 'CCDC 1889350'
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;
_audit_creation_date             2017-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H7 N5 O2'
_chemical_formula_sum            'C11 H7 N5 O2'
_chemical_formula_weight         241.22
_chemical_absolute_configuration unk
_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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   7.1519(14)
_cell_length_b                   10.616(2)
_cell_length_c                   13.902(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1055.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3294
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      1.4648
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8386
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2297
_reflns_number_total             2370
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.183
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0513P)²+0.5331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1388
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C11(H11), C9(H9), C3(H3), C2(H2), C10(H10)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N3 N 0.0051(3) 0.95747(18) 0.47852(14) 0.0308(5) Uani 1 d . . .
N4 N 0.0017(3) 0.9720(2) 0.64488(15) 0.0344(5) Uani 1 d . . .
C7 C 0.0511(3) 1.0245(2) 0.56216(18) 0.0286(5) Uani 1 d . . .
N5 N 0.2088(3) 1.1933(2) 0.46712(17) 0.0366(5) Uani 1 d . . .
C8 C 0.1400(3) 1.1413(2) 0.55761(19) 0.0301(5) Uani 1 d . . .
O1 O 0.3040(3) 1.12615(19) 0.41509(16) 0.0452(5) Uani 1 d . . .
C5 C 0.0552(4) 0.7262(2) 0.5171(2) 0.0329(5) Uani 1 d . . .
H5 H 0.0899 0.7343 0.5828 0.039 Uiso 1 calc . . R
C1 C -0.0433(4) 0.8188(2) 0.36482(19) 0.0347(6) Uani 1 d . . .
C4 C 0.0454(4) 0.6105(2) 0.4714(2) 0.0395(6) Uani 1 d . . .
H4 H 0.0741 0.5366 0.5070 0.047 Uiso 1 calc . . R
C11 C 0.0381(4) 1.0375(3) 0.72556(19) 0.0410(6) Uani 1 d . . .
H11 H 0.0075 1.0003 0.7857 0.049 Uiso 1 calc . . R
C9 C 0.1696(4) 1.2104(2) 0.6400(2) 0.0371(6) Uani 1 d . . .
H9 H 0.2235 1.2922 0.6379 0.045 Uiso 1 calc . . R
N1 N -0.0851(4) 0.9380(2) 0.32929(17) 0.0444(6) Uani 1 d . . .
N2 N -0.0550(4) 1.0197(2) 0.39753(16) 0.0398(6) Uani 1 d . . .
C6 C 0.0108(3) 0.8299(2) 0.46038(17) 0.0282(5) Uani 1 d . . .
C3 C -0.0055(4) 0.5986(3) 0.3739(2) 0.0449(7) Uani 1 d . . .
H3 H -0.0078 0.5173 0.3454 0.054 Uiso 1 calc . . R
C2 C -0.0514(5) 0.7004(3) 0.3198(2) 0.0447(7) Uani 1 d . . .
H2 H -0.0875 0.6919 0.2544 0.054 Uiso 1 calc . . R
O2 O 0.1722(4) 1.30389(18) 0.44812(18) 0.0599(7) Uani 1 d . . .
C10 C 0.1176(4) 1.1557(3) 0.7256(2) 0.0418(7) Uani 1 d . . .
H10 H 0.1364 1.1992 0.7845 0.050 Uiso 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 C7 1.402(3) . ?
N3 N2 1.375(3) . ?
N3 C6 1.378(3) . ?
N4 C7 1.326(3) . ?
N4 C11 1.345(3) . ?
C7 C8 1.395(3) . ?
N5 C8 1.459(3) . ?
N5 O1 1.222(3) . ?
N5 O2 1.232(3) . ?
C8 C9 1.377(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.385(4) . ?
C5 C6 1.391(3) . ?
C1 N1 1.391(4) . ?
C1 C6 1.389(4) . ?
C1 C2 1.406(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.409(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.377(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(4) . ?
N1 N2 1.304(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.357(5) . ?
C2 H2 0.9500 . ?
C10 H10 0.9500 . ?

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 N3 C7 120.58(19) . . ?
N2 N3 C6 109.4(2) . . ?
C6 N3 C7 130.0(2) . . ?
C7 N4 C11 117.0(2) . . ?
N4 C7 N3 116.3(2) . . ?
N4 C7 C8 122.3(2) . . ?
C8 C7 N3 121.3(2) . . ?
O1 N5 C8 118.5(2) . . ?
O1 N5 O2 123.2(3) . . ?
O2 N5 C8 118.3(2) . . ?
C7 C8 N5 121.9(2) . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 N5 117.6(2) . . ?
C4 C5 H5 122.3 . . ?
C4 C5 C6 115.5(2) . . ?
C6 C5 H5 122.3 . . ?
N1 C1 C2 130.3(2) . . ?
C6 C1 N1 108.8(2) . . ?
C6 C1 C2 120.9(3) . . ?
C5 C4 H4 118.9 . . ?
C5 C4 C3 122.3(3) . . ?
C3 C4 H4 118.9 . . ?
N4 C11 H11 118.3 . . ?
N4 C11 C10 123.4(3) . . ?
C10 C11 H11 118.3 . . ?
C8 C9 H9 121.5 . . ?
C10 C9 C8 116.9(2) . . ?
C10 C9 H9 121.5 . . ?
N2 N1 C1 108.1(2) . . ?
N1 N2 N3 109.1(2) . . ?
N3 C6 C5 132.9(2) . . ?
N3 C6 C1 104.5(2) . . ?
C1 C6 C5 122.6(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 H3 119.2 . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.1(3) . . ?
C3 C2 H2 121.4 . . ?
C11 C10 H10 120.1 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H10 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C7 C8 N5 -7.2(4) . . . . ?
N3 C7 C8 C9 174.4(2) . . . . ?
N4 C7 C8 N5 174.4(2) . . . . ?
N4 C7 C8 C9 -4.0(4) . . . . ?
N4 C11 C10 C9 -2.2(4) . . . . ?
C7 N3 N2 N1 178.7(2) . . . . ?
C7 N3 C6 C5 2.8(5) . . . . ?
C7 N3 C6 C1 -177.8(2) . . . . ?
C7 N4 C11 C10 2.0(4) . . . . ?
C7 C8 C9 C10 3.6(4) . . . . ?
N5 C8 C9 C10 -174.9(2) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
O1 N5 C8 C7 -48.9(3) . . . . ?
O1 N5 C8 C9 129.6(3) . . . . ?
C5 C4 C3 C2 -1.3(5) . . . . ?
C1 N1 N2 N3 -0.4(3) . . . . ?
C4 C5 C6 N3 -179.6(3) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C4 C3 C2 C1 0.9(4) . . . . ?
C11 N4 C7 N3 -177.4(2) . . . . ?
C11 N4 C7 C8 1.1(4) . . . . ?
N1 C1 C6 N3 -1.8(3) . . . . ?
N1 C1 C6 C5 177.6(2) . . . . ?
N1 C1 C2 C3 -178.5(3) . . . . ?
N2 N3 C7 N4 141.4(2) . . . . ?
N2 N3 C7 C8 -37.0(4) . . . . ?
N2 N3 C6 C5 -177.8(3) . . . . ?
N2 N3 C6 C1 1.6(3) . . . . ?
C6 N3 C7 N4 -39.2(4) . . . . ?
C6 N3 C7 C8 142.3(3) . . . . ?
C6 N3 N2 N1 -0.8(3) . . . . ?
C6 C5 C4 C3 0.2(4) . . . . ?
C6 C1 N1 N2 1.4(3) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
C2 C1 N1 N2 -179.5(3) . . . . ?
C2 C1 C6 N3 179.0(2) . . . . ?
C2 C1 C6 C5 -1.5(4) . . . . ?
O2 N5 C8 C7 133.0(3) . . . . ?
O2 N5 C8 C9 -48.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bwn17079
_database_code_depnum_ccdc_archive 'CCDC 1889351'
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;
_audit_creation_date             2017-05-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H7 N5'
_chemical_formula_sum            'C11 H7 N5'
_chemical_formula_weight         209.22
_chemical_absolute_configuration ?
_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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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'

_cell_length_a                   4.5338(9)
_cell_length_b                   12.919(3)
_cell_length_c                   16.167(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     946.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3092
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      1.2595
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3835
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         2.018
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                1944
_reflns_number_total             2112
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 627 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+0.2250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1129
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.6219(5) -0.37109(17) -0.63633(15) 0.0371(6) Uani 1 1 d . . . . .
N2 N -0.4792(5) -0.53805(15) -0.61733(12) 0.0274(5) Uani 1 1 d . . . . .
N3 N -0.2725(5) -0.45373(17) -0.72664(13) 0.0346(5) Uani 1 1 d . . . . .
C1 C -0.7618(6) -0.4142(2) -0.56875(16) 0.0338(6) Uani 1 1 d . . . . .
C2 C -0.9645(7) -0.3671(3) -0.51514(19) 0.0441(7) Uani 1 1 d . . . . .
H2 H -1.0253 -0.2974 -0.5227 0.053 Uiso 1 1 calc R . . . .
C3 C -1.0712(7) -0.4264(3) -0.45114(19) 0.0479(8) Uani 1 1 d . . . . .
H3 H -1.2080 -0.3963 -0.4137 0.057 Uiso 1 1 calc R . . . .
C4 C -0.9857(7) -0.5292(3) -0.43917(18) 0.0463(8) Uani 1 1 d . . . . .
H4 H -1.0664 -0.5669 -0.3941 0.056 Uiso 1 1 calc R . . . .
C5 C -0.7862(7) -0.5778(2) -0.49137(16) 0.0380(6) Uani 1 1 d . . . . .
H5 H -0.7271 -0.6477 -0.4838 0.046 Uiso 1 1 calc R . . . .
C6 C -0.6797(6) -0.5171(2) -0.55528(16) 0.0311(6) Uani 1 1 d . . . . .
N7 N -0.4577(5) -0.44817(16) -0.66353(14) 0.0311(5) Uani 1 1 d . . . . .
C8 C -0.1652(6) -0.5528(2) -0.72082(16) 0.0317(6) Uani 1 1 d . . . . .
C9 C 0.0437(6) -0.6046(2) -0.76943(17) 0.0368(6) Uani 1 1 d . . . . .
H9 H 0.1394 -0.5719 -0.8147 0.044 Uiso 1 1 calc R . . . .
C10 C 0.1025(6) -0.7054(2) -0.74806(18) 0.0406(7) Uani 1 1 d . . . . .
H10 H 0.2425 -0.7439 -0.7791 0.049 Uiso 1 1 calc R . . . .
C11 C -0.0408(7) -0.7522(2) -0.6812(2) 0.0420(7) Uani 1 1 d . . . . .
H11 H 0.0049 -0.8225 -0.6696 0.050 Uiso 1 1 calc R . . . .
N12 N -0.2380(5) -0.70494(16) -0.63242(13) 0.0354(5) Uani 1 1 d . . . . .
C13 C -0.2890(6) -0.60750(18) -0.65462(15) 0.0284(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
N1 C1 1.381(3) . ?
N1 N7 1.319(3) . ?
N2 C6 1.380(3) . ?
N2 N7 1.384(3) . ?
N2 C13 1.383(3) . ?
N3 N7 1.323(3) . ?
N3 C8 1.373(3) . ?
C1 C2 1.402(4) . ?
C1 C6 1.398(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(4) . ?
C8 C9 1.401(4) . ?
C8 C13 1.400(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.399(4) . ?
C11 H11 0.9500 . ?
C11 N12 1.340(4) . ?
N12 C13 1.329(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
N7 N1 C1 102.6(2) . . ?
C6 N2 N7 105.9(2) . . ?
C6 N2 C13 148.7(2) . . ?
C13 N2 N7 105.4(2) . . ?
N7 N3 C8 102.9(2) . . ?
N1 C1 C2 128.0(3) . . ?
N1 C1 C6 112.6(2) . . ?
C6 C1 C2 119.4(3) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 C1 117.1(3) . . ?
C3 C2 H2 121.5 . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.4(3) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.8(3) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 122.4 . . ?
C6 C5 C4 115.2(3) . . ?
C6 C5 H5 122.4 . . ?
N2 C6 C1 104.4(2) . . ?
N2 C6 C5 131.4(3) . . ?
C5 C6 C1 124.2(3) . . ?
N1 N7 N2 114.4(2) . . ?
N1 N7 N3 131.0(2) . . ?
N3 N7 N2 114.5(2) . . ?
N3 C8 C9 130.3(2) . . ?
N3 C8 C13 112.4(2) . . ?
C13 C8 C9 117.3(2) . . ?
C8 C9 H9 121.9 . . ?
C10 C9 C8 116.3(3) . . ?
C10 C9 H9 121.9 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 117.7 . . ?
N12 C11 C10 124.6(3) . . ?
N12 C11 H11 117.7 . . ?
C13 N12 C11 112.9(2) . . ?
N2 C13 C8 104.8(2) . . ?
N12 C13 N2 127.2(2) . . ?
N12 C13 C8 127.9(2) . . ?

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 C2 C3 -179.2(3) . . . . ?
N1 C1 C6 N2 0.2(3) . . . . ?
N1 C1 C6 C5 179.6(2) . . . . ?
N3 C8 C9 C10 -179.3(3) . . . . ?
N3 C8 C13 N2 -0.7(3) . . . . ?
N3 C8 C13 N12 178.8(2) . . . . ?
C1 N1 N7 N2 -0.8(3) . . . . ?
C1 N1 N7 N3 -179.6(3) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C1 C6 N2 -179.3(2) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 N2 179.0(3) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C6 N2 N7 N1 0.9(3) . . . . ?
C6 N2 N7 N3 179.9(2) . . . . ?
C6 N2 C13 C8 -179.4(4) . . . . ?
C6 N2 C13 N12 1.1(6) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
N7 N1 C1 C2 179.8(3) . . . . ?
N7 N1 C1 C6 0.3(3) . . . . ?
N7 N2 C6 C1 -0.6(3) . . . . ?
N7 N2 C6 C5 -179.9(3) . . . . ?
N7 N2 C13 C8 0.4(3) . . . . ?
N7 N2 C13 N12 -179.2(2) . . . . ?
N7 N3 C8 C9 -178.7(3) . . . . ?
N7 N3 C8 C13 0.8(3) . . . . ?
C8 N3 N7 N1 178.3(3) . . . . ?
C8 N3 N7 N2 -0.5(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C8 C13 N2 178.8(2) . . . . ?
C9 C8 C13 N12 -1.6(4) . . . . ?
C9 C10 C11 N12 -1.1(5) . . . . ?
C10 C11 N12 C13 0.9(4) . . . . ?
C11 N12 C13 N2 180.0(3) . . . . ?
C11 N12 C13 C8 0.5(4) . . . . ?
C13 N2 C6 C1 179.1(4) . . . . ?
C13 N2 C6 C5 -0.2(6) . . . . ?
C13 N2 N7 N1 -178.9(2) . . . . ?
C13 N2 N7 N3 0.1(3) . . . . ?
C13 C8 C9 C10 1.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bwn18427a
_database_code_depnum_ccdc_archive 'CCDC 1889352'
_audit_update_record             
;
2019-01-08 deposited with the CCDC.	2019-11-05 downloaded from the CCDC.
;
_audit_creation_date             2018-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H3 N13 O4, C3 H7 N O'
_chemical_formula_sum            'C14 H10 N14 O5'
_chemical_formula_weight         454.36
_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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   17.868(4)
_cell_length_b                   6.8028(14)
_cell_length_c                   15.914(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.01(3)
_cell_angle_gamma                90
_cell_volume                     1876.8(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4947
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4584
_cell_measurement_theta_min      1.3188
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13443
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.436
_diffrn_reflns_theta_min         2.615
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'multiwire proportional'
_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                3423
_reflns_number_total             4232
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0945
_refine_ls_restrained_S_all      1.239
_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)+(0.0458P)²+2.1048P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1788
_refine_ls_wR_factor_ref         0.1917
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C2(H2), C9(H9), C12(H12)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O3 O 0.75074(14) 0.1073(4) 0.52536(16) 0.0431(6) Uani 1 1 d . . . A 2
O1 O 0.76640(14) 1.0269(4) 0.33543(17) 0.0445(6) Uani 1 1 d . . . B 1
O4 O 0.85724(14) 0.2229(4) 0.50248(19) 0.0509(7) Uani 1 1 d . . . A 2
N4 N 0.45327(15) 0.4105(4) 0.39691(17) 0.0290(6) Uani 1 1 d . . . . .
N9 N 0.55134(14) 0.8013(4) 0.32903(16) 0.0289(6) Uani 1 1 d . . . . .
N11 N 0.55357(14) 0.6203(4) 0.36803(16) 0.0265(6) Uani 1 1 d . . . . .
N8 N 0.48176(15) 0.8758(4) 0.30146(17) 0.0321(6) Uani 1 1 d . . . . .
N2 N 0.38455(16) 0.1203(4) 0.45184(19) 0.0350(7) Uani 1 1 d . . . . .
N10 N 0.62083(15) 0.8745(4) 0.32689(18) 0.0330(6) Uani 1 1 d . . . . .
N13 N 0.78723(16) 0.2322(4) 0.49579(19) 0.0364(7) Uani 1 1 d . . . A 2
N1 N 0.33975(16) 0.2508(4) 0.41396(19) 0.0357(7) Uani 1 1 d . . . . .
N5 N 0.31314(16) 0.8922(4) 0.27722(19) 0.0380(7) Uani 1 1 d . . . . .
N12 N 0.79797(17) 0.8732(4) 0.3625(2) 0.0395(7) Uani 1 1 d . . . B 1
N6 N 0.24228(17) 0.8872(5) 0.27515(19) 0.0400(7) Uani 1 1 d . . . . .
O2 O 0.86767(16) 0.8454(4) 0.3735(2) 0.0682(10) Uani 1 1 d . . . B 1
N3 N 0.41768(18) -0.0082(5) 0.4878(2) 0.0434(8) Uani 1 1 d . . . . .
C7 C 0.66967(18) 0.7300(5) 0.3667(2) 0.0289(7) Uani 1 1 d . . . . .
C11 C 0.66544(17) 0.4015(5) 0.43412(19) 0.0284(7) Uani 1 1 d . . . . .
H11 H 0.637000 0.295715 0.450047 0.034 Uiso 1 1 calc R . . . .
C6 C 0.63080(17) 0.5678(5) 0.39295(19) 0.0260(7) Uani 1 1 d . . . . .
C10 C 0.74545(18) 0.4012(5) 0.4504(2) 0.0303(7) Uani 1 1 d . . . . .
C1 C 0.37616(18) 0.4132(5) 0.3852(2) 0.0296(7) Uani 1 1 d . . . . .
C5 C 0.47822(18) 0.5731(5) 0.3660(2) 0.0287(7) Uani 1 1 d . . . . .
C4 C 0.43570(18) 0.7328(5) 0.3245(2) 0.0291(7) Uani 1 1 d . . . . .
C3 C 0.35555(18) 0.7286(5) 0.31587(19) 0.0296(7) Uani 1 1 d . . . . .
C8 C 0.75093(18) 0.7163(5) 0.3855(2) 0.0318(7) Uani 1 1 d . . . . .
C2 C 0.32602(18) 0.5649(5) 0.3473(2) 0.0312(7) Uani 1 1 d . . . . .
H2 H 0.272261 0.554746 0.343466 0.037 Uiso 1 1 calc R . . . .
N7 N 0.17881(19) 0.9051(5) 0.2690(2) 0.0548(9) Uani 1 1 d . . . . .
N14 N 0.95058(18) 0.6596(6) 0.6289(3) 0.0582(10) Uani 1 1 d . . . . .
O5 O 0.84526(18) 0.5137(6) 0.6520(2) 0.0859(12) Uani 1 1 d . . . . .
C9 C 0.78771(18) 0.5530(5) 0.4273(2) 0.0326(7) Uani 1 1 d . . . . .
H9 H 0.842386 0.544858 0.440307 0.039 Uiso 1 1 calc R . . . .
C12 C 0.8789(2) 0.6597(8) 0.6350(3) 0.0580(12) Uani 1 1 d . . . . .
H12 H 0.851295 0.780219 0.625733 0.070 Uiso 1 1 calc R . . . .
C14 C 0.9957(3) 0.4809(9) 0.6411(5) 0.109(2) Uani 1 1 d . . . . .
H14A H 1.041865 0.499446 0.688280 0.164 Uiso 1 1 calc GR . . . .
H14B H 1.010993 0.448966 0.587607 0.164 Uiso 1 1 calc GR . . . .
H14C H 0.964726 0.373075 0.655772 0.164 Uiso 1 1 calc GR . . . .
C13 C 0.9883(4) 0.8378(9) 0.6099(5) 0.121(3) Uani 1 1 d . . . . .
H13A H 0.996739 0.829020 0.551395 0.181 Uiso 1 1 calc GR . . . .
H13B H 1.037945 0.852872 0.652003 0.181 Uiso 1 1 calc GR . . . .
H13C H 0.955477 0.951508 0.613324 0.181 Uiso 1 1 calc GR . . . .


_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
O3 N13 1.232(4) . ?
O1 N12 1.216(4) . ?
O4 N13 1.231(3) . ?
N4 C1 1.345(4) . ?
N4 C5 1.331(4) . ?
N9 N11 1.376(3) . ?
N9 N8 1.315(4) . ?
N9 N10 1.346(4) . ?
N11 C6 1.387(4) . ?
N11 C5 1.376(4) . ?
N8 C4 1.380(4) . ?
N2 N1 1.248(4) . ?
N2 N3 1.131(4) . ?
N10 C7 1.364(4) . ?
N13 C10 1.462(4) . ?
N1 C1 1.414(4) . ?
N5 N6 1.259(4) . ?
N5 C3 1.402(4) . ?
N12 O2 1.230(4) . ?
N12 C8 1.459(4) . ?
N6 N7 1.121(4) . ?
C7 C6 1.419(4) . ?
C7 C8 1.413(4) . ?
C11 H11 0.9500 . ?
C11 C6 1.377(4) . ?
C11 C10 1.390(4) . ?
C10 C9 1.381(5) . ?
C1 C2 1.403(4) . ?
C5 C4 1.396(4) . ?
C4 C3 1.405(4) . ?
C3 C2 1.378(5) . ?
C8 C9 1.377(5) . ?
C2 H2 0.9500 . ?
N14 C12 1.307(5) . ?
N14 C14 1.446(6) . ?
N14 C13 1.453(6) . ?
O5 C12 1.225(6) . ?
C9 H9 0.9500 . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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 N4 C1 111.1(3) . . ?
N8 N9 N11 114.6(2) . . ?
N8 N9 N10 130.7(3) . . ?
N10 N9 N11 114.6(2) . . ?
N9 N11 C6 106.1(2) . . ?
N9 N11 C5 106.1(2) . . ?
C5 N11 C6 147.8(3) . . ?
N9 N8 C4 102.5(3) . . ?
N3 N2 N1 172.0(3) . . ?
N9 N10 C7 102.3(2) . . ?
O3 N13 C10 118.5(3) . . ?
O4 N13 O3 123.5(3) . . ?
O4 N13 C10 118.0(3) . . ?
N2 N1 C1 114.9(3) . . ?
N6 N5 C3 115.0(3) . . ?
O1 N12 O2 123.3(3) . . ?
O1 N12 C8 118.2(3) . . ?
O2 N12 C8 118.5(3) . . ?
N7 N6 N5 171.5(4) . . ?
N10 C7 C6 113.2(3) . . ?
N10 C7 C8 130.9(3) . . ?
C8 C7 C6 116.0(3) . . ?
C6 C11 H11 122.8 . . ?
C6 C11 C10 114.4(3) . . ?
C10 C11 H11 122.8 . . ?
N11 C6 C7 103.9(3) . . ?
C11 C6 N11 130.5(3) . . ?
C11 C6 C7 125.7(3) . . ?
C11 C10 N13 118.2(3) . . ?
C9 C10 N13 118.2(3) . . ?
C9 C10 C11 123.6(3) . . ?
N4 C1 N1 118.7(3) . . ?
N4 C1 C2 126.6(3) . . ?
C2 C1 N1 114.7(3) . . ?
N4 C5 N11 126.7(3) . . ?
N4 C5 C4 129.0(3) . . ?
N11 C5 C4 104.3(3) . . ?
N8 C4 C5 112.5(3) . . ?
N8 C4 C3 130.4(3) . . ?
C5 C4 C3 117.1(3) . . ?
N5 C3 C4 117.2(3) . . ?
C2 C3 N5 126.0(3) . . ?
C2 C3 C4 116.9(3) . . ?
C7 C8 N12 121.6(3) . . ?
C9 C8 N12 118.3(3) . . ?
C9 C8 C7 120.1(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.3 . . ?
C12 N14 C14 120.9(4) . . ?
C12 N14 C13 121.8(5) . . ?
C14 N14 C13 117.3(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.3(3) . . ?
C8 C9 H9 119.9 . . ?
N14 C12 H12 118.0 . . ?
O5 C12 N14 123.9(5) . . ?
O5 C12 H12 118.0 . . ?
N14 C14 H14A 109.5 . . ?
N14 C14 H14B 109.5 . . ?
N14 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N14 C13 H13A 109.5 . . ?
N14 C13 H13B 109.5 . . ?
N14 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O3 N13 C10 C11 -7.3(4) . . . . ?
O3 N13 C10 C9 171.8(3) . . . . ?
O1 N12 C8 C7 8.1(5) . . . . ?
O1 N12 C8 C9 -171.1(3) . . . . ?
O4 N13 C10 C11 172.8(3) . . . . ?
O4 N13 C10 C9 -8.1(5) . . . . ?
N4 C1 C2 C3 1.9(5) . . . . ?
N4 C5 C4 N8 179.9(3) . . . . ?
N4 C5 C4 C3 2.4(5) . . . . ?
N9 N11 C6 C7 0.9(3) . . . . ?
N9 N11 C6 C11 -179.6(3) . . . . ?
N9 N11 C5 N4 -179.8(3) . . . . ?
N9 N11 C5 C4 0.3(3) . . . . ?
N9 N8 C4 C5 0.1(3) . . . . ?
N9 N8 C4 C3 177.1(3) . . . . ?
N9 N10 C7 C6 0.4(3) . . . . ?
N9 N10 C7 C8 -179.8(3) . . . . ?
N11 N9 N8 C4 0.2(3) . . . . ?
N11 N9 N10 C7 0.2(3) . . . . ?
N11 C5 C4 N8 -0.2(4) . . . . ?
N11 C5 C4 C3 -177.7(3) . . . . ?
N8 N9 N11 C6 -179.5(3) . . . . ?
N8 N9 N11 C5 -0.3(3) . . . . ?
N8 N9 N10 C7 178.8(3) . . . . ?
N8 C4 C3 N5 0.7(5) . . . . ?
N8 C4 C3 C2 -178.4(3) . . . . ?
N2 N1 C1 N4 2.9(4) . . . . ?
N2 N1 C1 C2 -176.3(3) . . . . ?
N10 N9 N11 C6 -0.7(3) . . . . ?
N10 N9 N11 C5 178.5(3) . . . . ?
N10 N9 N8 C4 -178.4(3) . . . . ?
N10 C7 C6 N11 -0.8(4) . . . . ?
N10 C7 C6 C11 179.7(3) . . . . ?
N10 C7 C8 N12 0.6(5) . . . . ?
N10 C7 C8 C9 179.7(3) . . . . ?
N13 C10 C9 C8 -179.2(3) . . . . ?
N1 C1 C2 C3 -179.0(3) . . . . ?
N5 C3 C2 C1 -179.4(3) . . . . ?
N12 C8 C9 C10 179.8(3) . . . . ?
N6 N5 C3 C4 -176.2(3) . . . . ?
N6 N5 C3 C2 2.8(5) . . . . ?
O2 N12 C8 C7 -173.6(3) . . . . ?
O2 N12 C8 C9 7.2(5) . . . . ?
C7 C8 C9 C10 0.6(5) . . . . ?
C11 C10 C9 C8 -0.2(5) . . . . ?
C6 N11 C5 N4 -1.2(7) . . . . ?
C6 N11 C5 C4 178.9(4) . . . . ?
C6 C7 C8 N12 -179.6(3) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
C6 C11 C10 N13 178.6(3) . . . . ?
C6 C11 C10 C9 -0.4(5) . . . . ?
C10 C11 C6 N11 -178.8(3) . . . . ?
C10 C11 C6 C7 0.6(5) . . . . ?
C1 N4 C5 N11 179.1(3) . . . . ?
C1 N4 C5 C4 -1.0(5) . . . . ?
C5 N4 C1 N1 179.7(3) . . . . ?
C5 N4 C1 C2 -1.2(4) . . . . ?
C5 N11 C6 C7 -177.7(4) . . . . ?
C5 N11 C6 C11 1.8(7) . . . . ?
C5 C4 C3 N5 177.6(3) . . . . ?
C5 C4 C3 C2 -1.5(4) . . . . ?
C4 C3 C2 C1 -0.4(4) . . . . ?
C8 C7 C6 N11 179.3(3) . . . . ?
C8 C7 C6 C11 -0.2(5) . . . . ?
C14 N14 C12 O5 0.8(8) . . . . ?
C13 N14 C12 O5 -179.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
