# 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 2021

####################################################################### 
# 
# 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_Wq190614_a
_database_code_depnum_ccdc_archive 'CCDC 1939028'
loop_
_audit_author_name
_audit_author_address
'Qing Lang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-10-02 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H4 N12 O2'
_chemical_formula_sum            'C5 H4 N12 O2'
_chemical_formula_weight         264.20

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.252(2)
_cell_length_b                   4.7966(8)
_cell_length_c                   17.536(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.273(5)
_cell_angle_gamma                90
_cell_volume                     1075.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3864
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      26.73

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5911
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            9641
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.187
_diffrn_reflns_theta_max         27.644
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2481
_reflns_number_gt                1624
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0437P)²+0.1642P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2481
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
C1 C 0.61285(11) 0.3544(4) 0.28455(8) 0.0468(4) Uani 1 1 d . . . . .
C2 C 0.57039(11) 0.4888(3) 0.34204(8) 0.0432(4) Uani 1 1 d . . . . .
C3 C 0.46062(13) 0.8082(3) 0.39205(9) 0.0518(4) Uani 1 1 d . . . . .
H3A H 0.423499 0.980688 0.374637 0.062 Uiso 1 1 calc R U . . .
H3B H 0.518916 0.850624 0.437101 0.062 Uiso 1 1 calc R U . . .
C4 C 0.28904(12) 0.6022(3) 0.37244(8) 0.0434(4) Uani 1 1 d . . . . .
C5 C 0.21160(12) 0.4179(3) 0.38532(8) 0.0451(4) Uani 1 1 d . . . . .
N1 N 0.68046(11) 0.1667(3) 0.31735(8) 0.0599(4) Uani 1 1 d . . . . .
N2 N 0.61280(10) 0.3771(3) 0.41069(7) 0.0534(4) Uani 1 1 d . . . . .
N3 N 0.58222(10) 0.4234(3) 0.20450(7) 0.0581(4) Uani 1 1 d . . . . .
N4 N 0.61691(12) 0.2651(4) 0.16105(9) 0.0668(4) Uani 1 1 d . . . . .
N5 N 0.64098(17) 0.1431(5) 0.11484(10) 0.1011(7) Uani 1 1 d . . . . .
N6 N 0.50025(10) 0.6988(3) 0.32923(7) 0.0501(4) Uani 1 1 d . . . . .
H6 H 0.4682(13) 0.733(4) 0.2827(10) 0.060 Uiso 1 1 d . U . . .
N7 N 0.39090(10) 0.6155(3) 0.41637(7) 0.0505(4) Uani 1 1 d . . . . .
H7 H 0.3969(14) 0.594(4) 0.4633(11) 0.061 Uiso 1 1 d . U . . .
N8 N 0.24882(11) 0.7530(3) 0.31038(7) 0.0559(4) Uani 1 1 d . . . . .
N9 N 0.12388(11) 0.4543(3) 0.33200(8) 0.0562(4) Uani 1 1 d . . . . .
N10 N 0.23205(11) 0.2284(3) 0.44763(7) 0.0565(4) Uani 1 1 d . . . . .
N11 N 0.15643(12) 0.0800(3) 0.45258(7) 0.057 Uani 1 1 d . . . . .
N12 N 0.09778(14) -0.0693(4) 0.46494(9) 0.0821(5) Uani 1 1 d . . . . .
O1 O 0.68314(9) 0.1750(3) 0.39679(6) 0.0644(4) Uani 1 1 d . . . . .
O2 O 0.14470(9) 0.6657(3) 0.28381(6) 0.0630(3) 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
C1 N1 1.293(2) . ?
C1 N3 1.3946(18) . ?
C1 C2 1.431(2) . ?
C2 N2 1.3022(18) . ?
C2 N6 1.349(2) . ?
C3 N6 1.4386(19) . ?
C3 N7 1.448(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N8 1.2984(19) . ?
C4 N7 1.3682(19) . ?
C4 C5 1.417(2) . ?
C5 N9 1.297(2) . ?
C5 N10 1.392(2) . ?
N1 O1 1.3847(17) . ?
N2 O1 1.4099(18) . ?
N3 N4 1.246(2) . ?
N4 N5 1.112(2) . ?
N6 H6 0.830(17) . ?
N7 H7 0.813(17) . ?
N8 O2 1.3993(17) . ?
N9 O2 1.3932(18) . ?
N10 N11 1.251(2) . ?
N11 N12 1.1190(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N3 126.65(15) . . ?
N1 C1 C2 110.81(13) . . ?
N3 C1 C2 122.54(14) . . ?
N2 C2 N6 124.88(14) . . ?
N2 C2 C1 108.18(14) . . ?
N6 C2 C1 126.93(13) . . ?
N6 C3 N7 112.51(13) . . ?
N6 C3 H3A 109.1 . . ?
N7 C3 H3A 109.1 . . ?
N6 C3 H3B 109.1 . . ?
N7 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N8 C4 N7 124.92(14) . . ?
N8 C4 C5 109.06(14) . . ?
N7 C4 C5 125.99(14) . . ?
N9 C5 N10 127.29(15) . . ?
N9 C5 C4 110.49(14) . . ?
N10 C5 C4 122.22(14) . . ?
C1 N1 O1 104.98(13) . . ?
C2 N2 O1 105.48(12) . . ?
N4 N3 C1 114.48(14) . . ?
N5 N4 N3 171.44(19) . . ?
C2 N6 C3 121.29(13) . . ?
C2 N6 H6 117.5(12) . . ?
C3 N6 H6 119.1(12) . . ?
C4 N7 C3 118.37(13) . . ?
C4 N7 H7 112.5(12) . . ?
C3 N7 H7 118.7(13) . . ?
C4 N8 O2 105.27(13) . . ?
C5 N9 O2 104.60(13) . . ?
N11 N10 C5 115.61(13) . . ?
N12 N11 N10 170.96(18) . . ?
N1 O1 N2 110.55(11) . . ?
N9 O2 N8 110.57(11) . . ?

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 N2 -0.62(18) . . . . ?
N3 C1 C2 N2 179.02(14) . . . . ?
N1 C1 C2 N6 178.12(14) . . . . ?
N3 C1 C2 N6 -2.2(2) . . . . ?
N8 C4 C5 N9 -0.26(17) . . . . ?
N7 C4 C5 N9 -178.40(14) . . . . ?
N8 C4 C5 N10 179.60(14) . . . . ?
N7 C4 C5 N10 1.5(2) . . . . ?
N3 C1 N1 O1 -179.52(15) . . . . ?
C2 C1 N1 O1 0.10(17) . . . . ?
N6 C2 N2 O1 -177.95(13) . . . . ?
C1 C2 N2 O1 0.82(15) . . . . ?
N1 C1 N3 N4 7.8(2) . . . . ?
C2 C1 N3 N4 -171.75(14) . . . . ?
N2 C2 N6 C3 -4.0(2) . . . . ?
C1 C2 N6 C3 177.46(14) . . . . ?
N7 C3 N6 C2 -70.82(18) . . . . ?
N8 C4 N7 C3 -0.9(2) . . . . ?
C5 C4 N7 C3 176.92(13) . . . . ?
N6 C3 N7 C4 -81.16(17) . . . . ?
N7 C4 N8 O2 178.59(13) . . . . ?
C5 C4 N8 O2 0.43(15) . . . . ?
N10 C5 N9 O2 -179.89(14) . . . . ?
C4 C5 N9 O2 -0.04(16) . . . . ?
N9 C5 N10 N11 -0.8(2) . . . . ?
C4 C5 N10 N11 179.34(13) . . . . ?
C1 N1 O1 N2 0.42(16) . . . . ?
C2 N2 O1 N1 -0.80(15) . . . . ?
C5 N9 O2 N8 0.31(16) . . . . ?
C4 N8 O2 N9 -0.47(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N6 H6 N9 0.830(17) 2.318(18) 3.1227(19) 163.4(16) 2 yes
N6 H6 O2 0.830(17) 2.645(18) 3.2600(19) 132.1(15) 2 yes
N7 H7 N2 0.813(17) 2.250(18) 3.0460(18) 166.1(17) 3_666 yes

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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 1937836'
loop_
_audit_author_name
_audit_author_address
'Qing Lang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2021-10-16 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H2 N14 O6'
_chemical_formula_sum            'C5 H2 N14 O6'
_chemical_formula_weight         354.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.7238(9)
_cell_length_b                   6.6508(6)
_cell_length_c                   20.1429(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.855(4)
_cell_angle_gamma                90
_cell_volume                     1301.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1952
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      25.33

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7444
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.226
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2273
_reflns_number_gt                1531
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0424P)²+0.7834P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2273
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
C1 C 0.7653(3) 0.5753(4) 0.15345(13) 0.0242(6) Uani 1 1 d . . . . .
H1A H 0.6986 0.4749 0.1351 0.029 Uiso 1 1 calc R U . . .
H1B H 0.7534 0.5851 0.2019 0.029 Uiso 1 1 calc R U . . .
C2 C 1.1382(3) 0.4215(5) 0.20069(15) 0.0354(8) Uani 1 1 d . . . . .
C3 C 0.9919(3) 0.4416(4) 0.19538(14) 0.0292(7) Uani 1 1 d . . . . .
C4 C 0.7017(3) 0.8859(4) 0.00370(13) 0.0254(7) Uani 1 1 d . . . . .
C5 C 0.6595(3) 0.7918(4) 0.06271(13) 0.0231(6) Uani 1 1 d . . . . .
N1 N 0.9047(2) 0.5060(3) 0.14243(11) 0.0229(5) Uani 1 1 d . . . . .
N2 N 0.9190(3) 0.4100(4) 0.08110(12) 0.0312(6) Uani 1 1 d . . . . .
N3 N 1.1768(3) 0.3722(5) 0.26101(13) 0.0469(8) Uani 1 1 d . . . . .
N4 N 0.9427(3) 0.4036(4) 0.25321(12) 0.0400(7) Uani 1 1 d . . . . .
N5 N 1.2266(3) 0.4491(5) 0.14930(13) 0.0424(7) Uani 1 1 d . . . . .
N6 N 1.3503(3) 0.4144(5) 0.16683(13) 0.0406(7) Uani 1 1 d . . . . .
N7 N 1.4633(3) 0.3866(5) 0.17428(14) 0.0551(9) Uani 1 1 d . . . . .
N8 N 0.7352(2) 0.7686(3) 0.12312(10) 0.0233(5) Uani 1 1 d . . . . .
N9 N 0.7835(2) 0.9391(4) 0.15531(11) 0.0247(6) Uani 1 1 d . . . . .
N10 N 0.6075(3) 0.8586(4) -0.04350(12) 0.0365(7) Uani 1 1 d . . . . .
N11 N 0.5409(3) 0.7083(4) 0.05212(12) 0.0337(6) Uani 1 1 d . . . . .
N12 N 0.8245(3) 0.9885(4) 0.00067(11) 0.0339(6) Uani 1 1 d . . . . .
N13 N 0.8476(3) 1.0627(4) -0.05494(13) 0.0388(7) Uani 1 1 d . . . . .
N14 N 0.8851(4) 1.1362(5) -0.10057(15) 0.0590(9) Uani 1 1 d . . . . .
O1 O 0.8373(2) 0.4561(3) 0.03674(10) 0.0395(6) Uani 1 1 d . . . . .
O2 O 1.0120(2) 0.2899(4) 0.07805(11) 0.0482(7) Uani 1 1 d . . . . .
O3 O 1.0556(2) 0.3643(4) 0.29485(11) 0.0522(7) Uani 1 1 d . . . . .
O4 O 0.8623(2) 0.9142(3) 0.20339(9) 0.0331(5) Uani 1 1 d . . . . .
O5 O 0.7413(2) 1.0994(3) 0.13262(9) 0.0311(5) Uani 1 1 d . . . . .
O6 O 0.5063(2) 0.7448(3) -0.01385(11) 0.0413(6) 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
C1 N8 1.447(3) . ?
C1 N1 1.458(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N3 1.296(4) . ?
C2 N5 1.390(4) . ?
C2 C3 1.428(4) . ?
C3 N4 1.306(4) . ?
C3 N1 1.397(4) . ?
C4 N10 1.300(4) . ?
C4 N12 1.379(4) . ?
C4 C5 1.421(4) . ?
C5 N11 1.288(4) . ?
C5 N8 1.399(3) . ?
N1 N2 1.404(3) . ?
N2 O1 1.205(3) . ?
N2 O2 1.210(3) . ?
N3 O3 1.391(3) . ?
N4 O3 1.373(3) . ?
N5 N6 1.258(4) . ?
N6 N7 1.117(4) . ?
N8 N9 1.377(3) . ?
N9 O4 1.216(3) . ?
N9 O5 1.223(3) . ?
N10 O6 1.399(3) . ?
N11 O6 1.376(3) . ?
N12 N13 1.255(3) . ?
N13 N14 1.118(4) . ?

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
N8 C1 N1 112.7(2) . . ?
N8 C1 H1A 109.0 . . ?
N1 C1 H1A 109.0 . . ?
N8 C1 H1B 109.0 . . ?
N1 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
N3 C2 N5 124.8(3) . . ?
N3 C2 C3 109.5(3) . . ?
N5 C2 C3 125.6(3) . . ?
N4 C3 N1 120.3(3) . . ?
N4 C3 C2 108.8(3) . . ?
N1 C3 C2 130.6(3) . . ?
N10 C4 N12 128.1(3) . . ?
N10 C4 C5 109.2(3) . . ?
N12 C4 C5 122.7(2) . . ?
N11 C5 N8 121.6(3) . . ?
N11 C5 C4 110.1(2) . . ?
N8 C5 C4 127.9(3) . . ?
C3 N1 N2 116.7(2) . . ?
C3 N1 C1 120.9(2) . . ?
N2 N1 C1 114.3(2) . . ?
O1 N2 O2 126.6(3) . . ?
O1 N2 N1 116.5(2) . . ?
O2 N2 N1 116.9(3) . . ?
C2 N3 O3 104.9(2) . . ?
C3 N4 O3 105.3(3) . . ?
N6 N5 C2 112.6(3) . . ?
N7 N6 N5 171.3(3) . . ?
N9 N8 C5 118.1(2) . . ?
N9 N8 C1 118.4(2) . . ?
C5 N8 C1 123.5(2) . . ?
O4 N9 O5 127.0(2) . . ?
O4 N9 N8 116.7(2) . . ?
O5 N9 N8 116.2(2) . . ?
C4 N10 O6 104.4(2) . . ?
C5 N11 O6 105.0(2) . . ?
N13 N12 C4 115.4(3) . . ?
N14 N13 N12 170.5(4) . . ?
N4 O3 N3 111.4(2) . . ?
N11 O6 N10 111.3(2) . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.057

