# 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_Yr201117_2_a
_audit_block_doi                 10.5517/ccdc.csd.cc26nh6l
_database_code_depnum_ccdc_archive 'CCDC 2045479'
loop_
_audit_author_name
_audit_author_address
'rui yang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-11-20 deposited with the CCDC.	2021-05-25 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 H2 N9 O4, H4 N'
_chemical_formula_sum            'C5 H6 N10 O4'
_chemical_formula_weight         270.20

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.2548(13)
_cell_length_b                   10.4530(17)
_cell_length_c                   13.508(2)
_cell_angle_alpha                93.199(5)
_cell_angle_beta                 99.554(4)
_cell_angle_gamma                106.901(4)
_cell_volume                     1093.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4561
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.00

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6711
_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            15368
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.423
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4980
_reflns_number_gt                2573
_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)+(0.0825P)²+0.5691P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4980
_refine_ls_number_parameters     367
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.1897
_refine_ls_wR_factor_gt          0.1551
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.020
_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 0.2416(4) 0.7903(4) 0.1180(3) 0.0540(9) Uani 1 1 d . U . . .
C2 C 0.1986(4) 0.6842(4) 0.0379(3) 0.0600(9) Uani 1 1 d . U . . .
C3 C 0.2425(5) 0.5600(4) 0.0332(3) 0.0648(10) Uani 1 1 d . U . . .
C4 C 0.3095(5) 0.3900(5) 0.0749(4) 0.0751(12) Uani 1 1 d . . . . .
C5 C 0.3510(6) 0.2794(5) 0.1254(4) 0.0908(14) Uani 1 1 d . . . . .
H5A H 0.416977 0.312848 0.192967 0.109 Uiso 1 1 calc R U . . .
H5B H 0.245529 0.210863 0.130785 0.109 Uiso 1 1 calc R U . . .
C6 C 0.1232(4) 0.6549(3) 0.5869(2) 0.0364(7) Uani 1 1 d . . . . .
C7 C 0.2204(3) 0.5739(3) 0.6355(2) 0.0360(7) Uani 1 1 d . . . . .
C8 C 0.1630(3) 0.4492(3) 0.6794(2) 0.0340(7) Uani 1 1 d . . . . .
C9 C 0.1739(4) 0.2755(3) 0.7429(2) 0.0395(7) Uani 1 1 d . . . . .
C10 C 0.2144(5) 0.1582(3) 0.7858(3) 0.0547(9) Uani 1 1 d . . . . .
H10A H 0.163899 0.139710 0.845430 0.066 Uiso 1 1 calc R U . . .
H10B H 0.338252 0.177360 0.805289 0.066 Uiso 1 1 calc R U . . .
N1 N 0.1716(4) 0.8829(4) 0.0878(3) 0.0727(9) Uani 1 1 d . . . . .
N2 N 0.1047(5) 0.7128(4) -0.0402(3) 0.0849(11) Uani 1 1 d . . . . .
N3 N 0.2892(4) 0.4972(3) 0.1156(2) 0.0638(8) Uani 1 1 d . . . . .
N4 N 0.2354(6) 0.4962(4) -0.0531(3) 0.0993(13) Uani 1 1 d . . . . .
N5 N 0.4492(8) 0.2232(6) 0.0675(5) 0.154(2) Uani 1 1 d . . . . .
N6 N 0.5188(7) 0.1507(6) 0.1100(5) 0.141(2) Uani 1 1 d . . . . .
N7 N 0.5834(8) 0.0723(7) 0.1307(7) 0.185(3) Uani 1 1 d . . . . .
N8 N 0.3391(3) 0.7817(3) 0.2085(2) 0.0496(7) Uani 1 1 d . . . . .
N9 N 0.3588(3) 0.8754(3) 0.2815(2) 0.0489(7) Uani 1 1 d . . . . .
N10 N 0.2313(3) 0.7581(3) 0.5580(2) 0.0511(7) Uani 1 1 d . . . . .
N11 N 0.3834(3) 0.6275(3) 0.6341(2) 0.0527(7) Uani 1 1 d . . . . .
N12 N 0.2739(3) 0.3783(2) 0.71357(18) 0.0378(6) Uani 1 1 d . . . . .
N13 N 0.0048(3) 0.3941(3) 0.6873(2) 0.0503(7) Uani 1 1 d . . . . .
N14 N 0.1413(5) 0.0371(3) 0.7065(2) 0.0675(9) Uani 1 1 d . U . . .
N15 N 0.0573(6) -0.0569(4) 0.7345(3) 0.0805(10) Uani 1 1 d . U . . .
N16 N -0.0292(7) -0.1587(5) 0.7494(3) 0.1172(16) Uani 1 1 d . U . . .
N17 N -0.0532(3) 0.6165(2) 0.57624(19) 0.0387(6) Uani 1 1 d . . . . .
N18 N -0.1303(3) 0.7000(2) 0.53569(19) 0.0382(6) Uani 1 1 d . . . . .
O1 O 0.0859(4) 0.8350(4) -0.0112(2) 0.0938(10) Uani 1 1 d . . . . .
O2 O 0.2812(5) 0.3816(3) -0.0258(2) 0.0972(10) Uani 1 1 d . . . . .
O3 O 0.4347(3) 0.8583(2) 0.36640(18) 0.0606(7) Uani 1 1 d . . . . .
O4 O 0.3059(3) 0.9742(2) 0.2731(2) 0.0668(7) Uani 1 1 d . . . . .
O5 O 0.3943(3) 0.7410(2) 0.5871(2) 0.0639(7) Uani 1 1 d . . . . .
O6 O 0.0101(3) 0.2761(2) 0.73022(18) 0.0532(6) Uani 1 1 d . . . . .
O7 O -0.2900(3) 0.6658(2) 0.52668(18) 0.0542(6) Uani 1 1 d . . . . .
O8 O -0.0514(3) 0.8084(2) 0.50703(17) 0.0481(6) Uani 1 1 d . . . . .
N19 N 0.3621(3) 0.5661(3) 0.3470(2) 0.0511(8) Uani 1 1 d D . . . .
H19A H 0.346(4) 0.557(3) 0.2870(14) 0.077 Uiso 1 1 d D U . . .
H19B H 0.279(3) 0.525(3) 0.366(2) 0.077 Uiso 1 1 d D U . . .
H19C H 0.437(3) 0.535(3) 0.368(2) 0.077 Uiso 1 1 d D U . . .
H19D H 0.391(4) 0.643(2) 0.367(2) 0.077 Uiso 1 1 d D U . . .
N20 N 0.7333(3) 0.9768(2) 0.5154(2) 0.0446(7) Uani 1 1 d D . . . .
H20A H 0.780(3) 1.058(2) 0.500(2) 0.067 Uiso 1 1 d D U . . .
H20B H 0.708(3) 0.980(3) 0.5763(15) 0.067 Uiso 1 1 d D U . . .
H20C H 0.801(3) 0.926(2) 0.511(2) 0.067 Uiso 1 1 d D U . . .
H20D H 0.633(3) 0.939(3) 0.4709(18) 0.067 Uiso 1 1 d D 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
C1 N1 1.314(5) . ?
C1 N8 1.370(4) . ?
C1 C2 1.428(5) . ?
C2 N2 1.304(5) . ?
C2 C3 1.447(6) . ?
C3 N4 1.294(5) . ?
C3 N3 1.380(5) . ?
C4 N3 1.287(5) . ?
C4 O2 1.335(5) . ?
C4 C5 1.469(6) . ?
C5 N5 1.432(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N10 1.310(4) . ?
C6 N17 1.374(4) . ?
C6 C7 1.439(4) . ?
C7 N11 1.302(4) . ?
C7 C8 1.448(4) . ?
C8 N13 1.290(4) . ?
C8 N12 1.377(3) . ?
C9 N12 1.278(4) . ?
C9 O6 1.336(3) . ?
C9 C10 1.485(4) . ?
C10 N14 1.518(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N1 O1 1.395(4) . ?
N2 O1 1.375(5) . ?
N4 O2 1.407(5) . ?
N5 N6 1.194(7) . ?
N6 N7 1.125(7) . ?
N8 N9 1.305(4) . ?
N9 O4 1.237(3) . ?
N9 O3 1.261(3) . ?
N10 O5 1.403(3) . ?
N11 O5 1.364(3) . ?
N13 O6 1.401(3) . ?
N14 N15 1.149(5) . ?
N15 N16 1.146(5) . ?
N17 N18 1.315(3) . ?
N18 O7 1.244(3) . ?
N18 O8 1.250(3) . ?
N19 H19A 0.794(18) . ?
N19 H19B 0.791(19) . ?
N19 H19C 0.804(19) . ?
N19 H19D 0.788(19) . ?
N20 H20A 0.878(18) . ?
N20 H20B 0.883(18) . ?
N20 H20C 0.881(18) . ?
N20 H20D 0.905(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
N1 C1 N8 131.3(3) . . ?
N1 C1 C2 108.9(3) . . ?
N8 C1 C2 119.8(3) . . ?
N2 C2 C1 109.4(4) . . ?
N2 C2 C3 120.1(4) . . ?
C1 C2 C3 130.5(3) . . ?
N4 C3 N3 114.3(4) . . ?
N4 C3 C2 120.4(4) . . ?
N3 C3 C2 125.3(3) . . ?
N3 C4 O2 112.7(4) . . ?
N3 C4 C5 128.1(4) . . ?
O2 C4 C5 119.2(4) . . ?
N5 C5 C4 108.9(4) . . ?
N5 C5 H5A 109.9 . . ?
C4 C5 H5A 109.9 . . ?
N5 C5 H5B 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
N10 C6 N17 131.3(3) . . ?
N10 C6 C7 108.2(2) . . ?
N17 C6 C7 120.5(2) . . ?
N11 C7 C6 109.6(2) . . ?
N11 C7 C8 120.1(2) . . ?
C6 C7 C8 130.3(2) . . ?
N13 C8 N12 114.8(3) . . ?
N13 C8 C7 123.2(2) . . ?
N12 C8 C7 122.0(2) . . ?
N12 C9 O6 113.3(2) . . ?
N12 C9 C10 129.3(3) . . ?
O6 C9 C10 117.4(3) . . ?
C9 C10 N14 108.7(3) . . ?
C9 C10 H10A 110.0 . . ?
N14 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
N14 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
C1 N1 O1 104.9(3) . . ?
C2 N2 O1 105.6(3) . . ?
C4 N3 C3 103.0(3) . . ?
C3 N4 O2 103.1(3) . . ?
N6 N5 C5 115.0(6) . . ?
N7 N6 N5 166.0(9) . . ?
N9 N8 C1 116.4(3) . . ?
O4 N9 O3 119.6(3) . . ?
O4 N9 N8 125.1(3) . . ?
O3 N9 N8 115.2(3) . . ?
C6 N10 O5 105.1(2) . . ?
C7 N11 O5 105.7(2) . . ?
C9 N12 C8 102.4(2) . . ?
C8 N13 O6 102.9(2) . . ?
N15 N14 C10 114.1(3) . . ?
N16 N15 N14 170.7(4) . . ?
N18 N17 C6 116.2(2) . . ?
O7 N18 O8 120.4(2) . . ?
O7 N18 N17 116.3(2) . . ?
O8 N18 N17 123.3(2) . . ?
N2 O1 N1 111.3(3) . . ?
C4 O2 N4 106.9(3) . . ?
N11 O5 N10 111.3(2) . . ?
C9 O6 N13 106.5(2) . . ?
H19A N19 H19B 111(2) . . ?
H19A N19 H19C 108.2(19) . . ?
H19B N19 H19C 107.0(19) . . ?
H19A N19 H19D 110.0(19) . . ?
H19B N19 H19D 112(2) . . ?
H19C N19 H19D 109(2) . . ?
H20A N20 H20B 110.7(17) . . ?
H20A N20 H20C 111.5(17) . . ?
H20B N20 H20C 110.9(17) . . ?
H20A N20 H20D 107.9(16) . . ?
H20B N20 H20D 107.5(17) . . ?
H20C N20 H20D 108.1(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 0.5(4) . . . . ?
N8 C1 C2 N2 179.5(3) . . . . ?
N1 C1 C2 C3 -179.5(4) . . . . ?
N8 C1 C2 C3 -0.5(6) . . . . ?
N2 C2 C3 N4 20.5(6) . . . . ?
C1 C2 C3 N4 -159.6(4) . . . . ?
N2 C2 C3 N3 -157.6(4) . . . . ?
C1 C2 C3 N3 22.3(6) . . . . ?
N3 C4 C5 N5 -149.1(5) . . . . ?
O2 C4 C5 N5 33.9(6) . . . . ?
N10 C6 C7 N11 -0.8(4) . . . . ?
N17 C6 C7 N11 178.0(3) . . . . ?
N10 C6 C7 C8 -179.2(3) . . . . ?
N17 C6 C7 C8 -0.4(5) . . . . ?
N11 C7 C8 N13 176.8(3) . . . . ?
C6 C7 C8 N13 -5.0(5) . . . . ?
N11 C7 C8 N12 -5.2(4) . . . . ?
C6 C7 C8 N12 173.1(3) . . . . ?
N12 C9 C10 N14 -106.5(4) . . . . ?
O6 C9 C10 N14 72.1(4) . . . . ?
N8 C1 N1 O1 -179.2(3) . . . . ?
C2 C1 N1 O1 -0.3(4) . . . . ?
C1 C2 N2 O1 -0.4(4) . . . . ?
C3 C2 N2 O1 179.6(3) . . . . ?
O2 C4 N3 C3 0.7(4) . . . . ?
C5 C4 N3 C3 -176.5(4) . . . . ?
N4 C3 N3 C4 -0.4(5) . . . . ?
C2 C3 N3 C4 177.8(4) . . . . ?
N3 C3 N4 O2 0.0(5) . . . . ?
C2 C3 N4 O2 -178.3(3) . . . . ?
C4 C5 N5 N6 166.2(6) . . . . ?
C5 N5 N6 N7 157(2) . . . . ?
N1 C1 N8 N9 5.4(5) . . . . ?
C2 C1 N8 N9 -173.3(3) . . . . ?
C1 N8 N9 O4 -4.7(4) . . . . ?
C1 N8 N9 O3 173.5(3) . . . . ?
N17 C6 N10 O5 -178.0(3) . . . . ?
C7 C6 N10 O5 0.7(3) . . . . ?
C6 C7 N11 O5 0.5(3) . . . . ?
C8 C7 N11 O5 179.1(3) . . . . ?
O6 C9 N12 C8 -0.1(3) . . . . ?
C10 C9 N12 C8 178.5(3) . . . . ?
N13 C8 N12 C9 0.1(3) . . . . ?
C7 C8 N12 C9 -178.1(3) . . . . ?
N12 C8 N13 O6 -0.1(3) . . . . ?
C7 C8 N13 O6 178.1(3) . . . . ?
C9 C10 N14 N15 -128.6(4) . . . . ?
N10 C6 N17 N18 -4.9(5) . . . . ?
C7 C6 N17 N18 176.6(3) . . . . ?
C6 N17 N18 O7 -179.5(2) . . . . ?
C6 N17 N18 O8 0.5(4) . . . . ?
C2 N2 O1 N1 0.2(4) . . . . ?
C1 N1 O1 N2 0.1(4) . . . . ?
N3 C4 O2 N4 -0.7(5) . . . . ?
C5 C4 O2 N4 176.8(4) . . . . ?
C3 N4 O2 C4 0.4(5) . . . . ?
C7 N11 O5 N10 -0.1(4) . . . . ?
C6 N10 O5 N11 -0.4(3) . . . . ?
N12 C9 O6 N13 0.0(3) . . . . ?
C10 C9 O6 N13 -178.8(3) . . . . ?
C8 N13 O6 C9 0.0(3) . . . . ?

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
C5 H5A N11 0.97 2.55 3.514(6) 170.5 2_666 yes
C5 H5B N16 0.97 2.57 3.360(7) 138.8 2_556 yes
C10 H10B N8 0.97 2.61 3.542(4) 160.6 2_666 yes
N19 H19A N3 0.794(18) 2.298(19) 3.086(4) 171(3) . yes
N19 H19A N8 0.794(18) 2.64(3) 3.036(4) 113(2) . yes
N19 H19B N17 0.791(19) 2.295(19) 3.080(4) 172(3) 2_566 yes
N19 H19B O7 0.791(19) 2.54(3) 3.017(3) 120(3) 2_566 yes
N19 H19C N11 0.804(19) 2.55(2) 3.305(4) 156(3) 2_666 yes
N19 H19D O3 0.788(19) 2.17(2) 2.925(4) 159(3) . yes
N20 H20A N10 0.878(18) 2.13(2) 2.946(3) 153(2) 2_676 yes
N20 H20A O8 0.878(18) 2.29(2) 2.990(3) 137(2) 2_676 yes
N20 H20B N9 0.883(18) 2.60(2) 3.376(4) 146(2) 2_676 yes
N20 H20B O3 0.883(18) 2.48(2) 3.043(3) 122(2) 2_676 yes
N20 H20B O4 0.883(18) 2.092(19) 2.961(4) 168(3) 2_676 yes
N20 H20C N18 0.881(18) 2.61(2) 3.405(3) 150(2) 1_655 yes
N20 H20C O7 0.881(18) 2.63(2) 3.215(3) 125(2) 1_655 yes
N20 H20C O8 0.881(18) 1.972(18) 2.852(3) 177(3) 1_655 yes
N20 H20D O3 0.905(18) 1.920(19) 2.822(4) 174(2) . yes

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_YR201205
_database_code_depnum_ccdc_archive 'CCDC 2048721'
loop_
_audit_author_name
_audit_author_address
'rui yang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2020-12-07 deposited with the CCDC.	2021-05-25 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 N8 O2'
_chemical_formula_sum            'C5 H4 N8 O2'
_chemical_formula_weight         208.16

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   19.831(2)
_cell_length_b                   5.3577(5)
_cell_length_c                   7.8562(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     834.71(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3282
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      27.47

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.135
_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  0.6510
_exptl_absorpt_correction_T_max  0.7457
_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            6956
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.308
_diffrn_reflns_theta_max         28.253
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             1987
_reflns_number_gt                1477
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_max     0.923
_reflns_Friedel_fraction_full    0.968

_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)+(0.0555P)²+0.1736P] 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_abs_structure_details 
;
 Flack x determined using 510 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1987
_refine_ls_number_parameters     136
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.094
_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 0.22464(17) 0.8194(7) 0.1236(5) 0.0373(8) Uani 1 1 d . . . . .
C2 C 0.25161(17) 0.6144(6) 0.2189(5) 0.0356(8) Uani 1 1 d . . . . .
C3 C 0.32180(17) 0.5535(6) 0.2546(5) 0.0360(8) Uani 1 1 d . . . . .
C4 C 0.40479(17) 0.3820(6) 0.3613(5) 0.0396(8) Uani 1 1 d . . . . .
C5 C 0.45473(17) 0.2330(8) 0.4613(6) 0.0485(10) Uani 1 1 d . . . . .
H5C H 0.431613 0.101496 0.522898 0.058 Uiso 1 1 calc R U . . .
H5D H 0.477077 0.339818 0.543439 0.058 Uiso 1 1 calc R U . . .
N1 N 0.15888(15) 0.8090(6) 0.1328(4) 0.0476(8) Uani 1 1 d . . . . .
N2 N 0.20262(14) 0.4835(6) 0.2831(5) 0.0455(8) Uani 1 1 d . . . . .
N3 N 0.37052(14) 0.6885(6) 0.1972(5) 0.0512(9) Uani 1 1 d . . . . .
N4 N 0.34059(13) 0.3567(5) 0.3569(4) 0.0362(7) Uani 1 1 d . . . . .
N5 N 0.25939(17) 0.9946(6) 0.0389(5) 0.0486(8) Uani 1 1 d . . . . .
H5A H 0.238321 1.111061 -0.014447 0.058 Uiso 1 1 calc R U . . .
H5B H 0.302738 0.990499 0.037990 0.058 Uiso 1 1 calc R U . . .
N6 N 0.50588(16) 0.1211(7) 0.3438(5) 0.0563(9) Uani 1 1 d . U . . .
N7 N 0.53993(18) -0.0253(8) 0.4088(6) 0.0636(10) Uani 1 1 d . U . . .
N8 N 0.5784(2) -0.1681(9) 0.4545(7) 0.0913(15) Uani 1 1 d . U . . .
O1 O 0.14474(12) 0.5978(5) 0.2320(4) 0.0531(8) Uani 1 1 d . . . . .
O2 O 0.42788(11) 0.5734(5) 0.2696(4) 0.0548(8) 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 1.307(5) . ?
C1 N5 1.341(5) . ?
C1 C2 1.433(5) . ?
C2 N2 1.300(5) . ?
C2 C3 1.457(5) . ?
C3 N3 1.288(5) . ?
C3 N4 1.378(5) . ?
C4 N4 1.281(4) . ?
C4 O2 1.334(5) . ?
C4 C5 1.495(5) . ?
C5 N6 1.497(5) . ?
C5 H5C 0.9700 . ?
C5 H5D 0.9700 . ?
N1 O1 1.402(5) . ?
N2 O1 1.361(4) . ?
N3 O2 1.414(4) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 N7 1.154(5) . ?
N7 N8 1.139(5) . ?

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 N5 124.7(3) . . ?
N1 C1 C2 108.1(3) . . ?
N5 C1 C2 127.1(3) . . ?
N2 C2 C1 109.7(3) . . ?
N2 C2 C3 121.2(3) . . ?
C1 C2 C3 129.0(3) . . ?
N3 C3 N4 115.6(3) . . ?
N3 C3 C2 121.6(3) . . ?
N4 C3 C2 122.8(3) . . ?
N4 C4 O2 114.1(3) . . ?
N4 C4 C5 128.0(3) . . ?
O2 C4 C5 117.8(3) . . ?
C4 C5 N6 109.8(4) . . ?
C4 C5 H5C 109.7 . . ?
N6 C5 H5C 109.7 . . ?
C4 C5 H5D 109.7 . . ?
N6 C5 H5D 109.7 . . ?
H5C C5 H5D 108.2 . . ?
C1 N1 O1 105.3(3) . . ?
C2 N2 O1 105.9(3) . . ?
C3 N3 O2 102.6(3) . . ?
C4 N4 C3 101.7(3) . . ?
C1 N5 H5A 120.0 . . ?
C1 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
N7 N6 C5 113.3(4) . . ?
N8 N7 N6 171.2(6) . . ?
N2 O1 N1 111.0(2) . . ?
C4 O2 N3 106.0(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 N2 0.3(4) . . . . ?
N5 C1 C2 N2 -179.9(4) . . . . ?
N1 C1 C2 C3 -176.2(4) . . . . ?
N5 C1 C2 C3 3.6(6) . . . . ?
N2 C2 C3 N3 -177.0(4) . . . . ?
C1 C2 C3 N3 -0.9(6) . . . . ?
N2 C2 C3 N4 0.1(6) . . . . ?
C1 C2 C3 N4 176.2(4) . . . . ?
N4 C4 C5 N6 123.2(4) . . . . ?
O2 C4 C5 N6 -60.0(5) . . . . ?
N5 C1 N1 O1 179.7(3) . . . . ?
C2 C1 N1 O1 -0.5(4) . . . . ?
C1 C2 N2 O1 0.1(4) . . . . ?
C3 C2 N2 O1 176.9(3) . . . . ?
N4 C3 N3 O2 -0.8(5) . . . . ?
C2 C3 N3 O2 176.5(3) . . . . ?
O2 C4 N4 C3 -0.9(4) . . . . ?
C5 C4 N4 C3 176.0(4) . . . . ?
N3 C3 N4 C4 1.1(5) . . . . ?
C2 C3 N4 C4 -176.2(3) . . . . ?
C4 C5 N6 N7 -169.3(4) . . . . ?
C2 N2 O1 N1 -0.4(4) . . . . ?
C1 N1 O1 N2 0.5(4) . . . . ?
N4 C4 O2 N3 0.5(5) . . . . ?
C5 C4 O2 N3 -176.7(3) . . . . ?
C3 N3 O2 C4 0.2(4) . . . . ?

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
C5 H5C N1 0.97 2.53 3.471(5) 162.5 3_545 yes
C5 H5D O2 0.97 2.63 3.516(5) 151.8 2_665 yes
N5 H5A N4 0.86 2.28 3.121(4) 165.4 3_564 yes
N5 H5B N3 0.86 2.45 3.015(4) 124.2 . yes
N5 H5B N8 0.86 2.62 3.413(6) 152.9 2_664 yes

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.047

