# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2107863'
loop_
_audit_author_name
_audit_author_address
'Feng Yang'
;Nanjing University Of Science And Technology
China
;
_audit_update_record             
;
2021-09-06 deposited with the CCDC.	2022-06-15 downloaded from the CCDC.
;
_audit_creation_date             2021-09-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6394)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H3 N6 O2, H5 N2'
_chemical_formula_sum            'C2 H8 N8 O2'
_chemical_formula_weight         176.16
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.6249(5)
_cell_length_b                   24.182(3)
_cell_length_c                   15.487(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.123(6)
_cell_angle_gamma                90
_cell_volume                     1356.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6904
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      60.236
_cell_measurement_theta_min      2.949
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1372 before and 0.0961 after correction.
The Ratio of minimum to maximum transmission is 0.8300.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10727
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.317
_diffrn_reflns_theta_min         2.949
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.19937059999999998
_diffrn_source_voltage           69.71
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2546
_reflns_number_total             3004
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3004
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.064
_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)+(0.0637P)²+0.5350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1207
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.6287(4) 0.34771(5) 0.36597(7) 0.0279(3) Uani 1 1 d . . . . .
O2 O 1.0838(3) 0.28948(5) 0.60721(7) 0.0227(3) Uani 1 1 d . . . . .
N1 N 0.9085(6) 0.43030(7) 0.46854(11) 0.0347(4) Uani 1 1 d . . . . .
H1A H 0.704(9) 0.4374(12) 0.4390(19) 0.058(8) Uiso 1 1 d . . . . .
H1B H 0.899(8) 0.4513(12) 0.518(2) 0.060(8) Uiso 1 1 d . . . . .
N2 N 0.8802(4) 0.37462(6) 0.49511(9) 0.0234(3) Uani 1 1 d . . . . .
H2 H 0.966(6) 0.3646(9) 0.5480(15) 0.033(6) Uiso 1 1 d . . . . .
N3 N 0.6538(4) 0.23583(6) 0.42337(9) 0.0223(3) Uani 1 1 d . . . . .
N4 N 0.7333(4) 0.19108(6) 0.47197(9) 0.0257(3) Uani 1 1 d . . . . .
N5 N 0.8981(4) 0.20549(6) 0.54577(9) 0.0239(3) Uani 1 1 d . . . . .
N6 N 0.9248(4) 0.26064(6) 0.54423(8) 0.0185(3) Uani 1 1 d . . . . .
C1 C 0.7555(4) 0.33708(7) 0.44013(10) 0.0194(3) Uani 1 1 d . . . . .
C2 C 0.7746(4) 0.27931(7) 0.46928(9) 0.0184(3) Uani 1 1 d . . . . .
O3 O 0.8409(3) 0.49953(5) 0.88320(8) 0.0250(3) Uani 1 1 d . . . . .
O4 O 0.2146(3) 0.36209(5) 0.78237(7) 0.0228(3) Uani 1 1 d . . . . .
N7 N 0.7105(4) 0.41952(7) 1.00639(9) 0.0251(3) Uani 1 1 d . . . . .
H7A H 0.806(7) 0.4531(11) 1.0150(16) 0.042(7) Uiso 1 1 d . . . . .
H7B H 0.905(8) 0.3957(11) 1.0106(17) 0.049(7) Uiso 1 1 d . . . . .
N8 N 0.5906(4) 0.41729(6) 0.91873(8) 0.0206(3) Uani 1 1 d . . . . .
H8 H 0.463(6) 0.3899(9) 0.9035(13) 0.026(5) Uiso 1 1 d . . . . .
N9 N 0.5524(4) 0.48667(6) 0.71184(9) 0.0239(3) Uani 1 1 d . . . . .
N10 N 0.3943(4) 0.46426(6) 0.64015(9) 0.0272(3) Uani 1 1 d . . . . .
N11 N 0.2552(4) 0.41539(6) 0.65740(9) 0.0250(3) Uani 1 1 d . . . . .
N12 N 0.3246(4) 0.40659(5) 0.74206(8) 0.0189(3) Uani 1 1 d . . . . .
C3 C 0.6591(4) 0.45772(6) 0.86430(10) 0.0181(3) Uani 1 1 d . . . . .
C4 C 0.5096(4) 0.45014(6) 0.77514(10) 0.0183(3) Uani 1 1 d . . . . .
N13 N 0.6933(4) 0.27675(6) 0.75871(9) 0.0203(3) Uani 1 1 d . . . . .
H13A H 0.832(6) 0.2864(9) 0.7102(15) 0.032(6) Uiso 1 1 d . . . . .
H13B H 0.512(7) 0.3037(10) 0.7670(15) 0.043(7) Uiso 1 1 d . . . . .
H13C H 0.840(7) 0.2728(9) 0.8087(15) 0.036(6) Uiso 1 1 d . . . . .
N14 N 0.5319(4) 0.22365(6) 0.73562(9) 0.0214(3) Uani 1 1 d . . . . .
H14A H 0.387(6) 0.2132(9) 0.7817(15) 0.031(6) Uiso 1 1 d . . . . .
H14B H 0.377(6) 0.2325(9) 0.6915(15) 0.032(6) Uiso 1 1 d . . . . .
N15 N 0.8291(4) 0.59437(6) 0.74986(9) 0.0204(3) Uani 1 1 d . . . . .
H15A H 0.779(6) 0.6154(10) 0.7042(14) 0.032(6) Uiso 1 1 d . . . . .
H15B H 1.068(7) 0.5982(9) 0.7684(15) 0.039(6) Uiso 1 1 d . . . . .
H15C H 0.791(6) 0.5583(10) 0.7321(13) 0.029(5) Uiso 1 1 d . . . . .
N16 N 0.5757(4) 0.60858(6) 0.81590(9) 0.0215(3) Uani 1 1 d . . . . .
H16A H 0.615(6) 0.5844(9) 0.8603(14) 0.033(6) Uiso 1 1 d . . . . .
H16B H 0.642(7) 0.6431(10) 0.8325(14) 0.035(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2480(19) . ?
O2 N6 1.3147(16) . ?
N1 H1A 0.87(3) . ?
N1 H1B 0.92(3) . ?
N1 N2 1.413(2) . ?
N2 H2 0.90(2) . ?
N2 C1 1.313(2) . ?
N3 N4 1.343(2) . ?
N3 C2 1.334(2) . ?
N4 N5 1.3169(19) . ?
N5 N6 1.337(2) . ?
N6 C2 1.3419(19) . ?
C1 C2 1.469(2) . ?
O3 C3 1.236(2) . ?
O4 N12 1.3133(18) . ?
N7 H7A 0.89(3) . ?
N7 H7B 0.91(3) . ?
N7 N8 1.4110(18) . ?
N8 H8 0.84(2) . ?
N8 C3 1.320(2) . ?
N9 N10 1.3445(19) . ?
N9 C4 1.333(2) . ?
N10 N11 1.316(2) . ?
N11 N12 1.3429(19) . ?
N12 C4 1.340(2) . ?
C3 C4 1.476(2) . ?
N13 H13A 0.95(2) . ?
N13 H13B 0.94(3) . ?
N13 H13C 0.93(2) . ?
N13 N14 1.4503(19) . ?
N14 H14A 0.94(2) . ?
N14 H14B 0.89(2) . ?
N15 H15A 0.88(2) . ?
N15 H15B 0.91(3) . ?
N15 H15C 0.92(2) . ?
N15 N16 1.441(2) . ?
N16 H16A 0.91(2) . ?
N16 H16B 0.90(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 106(3) . . ?
N2 N1 H1A 105.7(19) . . ?
N2 N1 H1B 106.3(19) . . ?
N1 N2 H2 119.7(14) . . ?
C1 N2 N1 119.79(14) . . ?
C1 N2 H2 120.2(14) . . ?
C2 N3 N4 106.08(13) . . ?
N5 N4 N3 110.73(13) . . ?
N4 N5 N6 106.21(12) . . ?
O2 N6 N5 123.07(12) . . ?
O2 N6 C2 128.02(14) . . ?
N5 N6 C2 108.89(13) . . ?
O1 C1 N2 124.10(15) . . ?
O1 C1 C2 119.35(14) . . ?
N2 C1 C2 116.55(13) . . ?
N3 C2 N6 108.09(14) . . ?
N3 C2 C1 125.10(13) . . ?
N6 C2 C1 126.78(14) . . ?
H7A N7 H7B 106(2) . . ?
N8 N7 H7A 106.4(16) . . ?
N8 N7 H7B 104.8(17) . . ?
N7 N8 H8 116.7(14) . . ?
C3 N8 N7 121.84(14) . . ?
C3 N8 H8 121.4(14) . . ?
C4 N9 N10 106.41(14) . . ?
N11 N10 N9 110.43(13) . . ?
N10 N11 N12 106.33(13) . . ?
O4 N12 N11 123.01(13) . . ?
O4 N12 C4 128.22(13) . . ?
C4 N12 N11 108.76(13) . . ?
O3 C3 N8 124.44(14) . . ?
O3 C3 C4 119.81(14) . . ?
N8 C3 C4 115.73(14) . . ?
N9 C4 N12 108.06(13) . . ?
N9 C4 C3 123.85(14) . . ?
N12 C4 C3 128.05(14) . . ?
H13A N13 H13B 109(2) . . ?
H13A N13 H13C 112(2) . . ?
H13B N13 H13C 110(2) . . ?
N14 N13 H13A 104.0(13) . . ?
N14 N13 H13B 111.7(15) . . ?
N14 N13 H13C 109.2(14) . . ?
N13 N14 H14A 106.4(13) . . ?
N13 N14 H14B 102.2(14) . . ?
H14A N14 H14B 107(2) . . ?
H15A N15 H15B 111(2) . . ?
H15A N15 H15C 106.3(19) . . ?
H15B N15 H15C 108.7(19) . . ?
N16 N15 H15A 108.3(14) . . ?
N16 N15 H15B 112.2(15) . . ?
N16 N15 H15C 110.1(14) . . ?
N15 N16 H16A 107.3(14) . . ?
N15 N16 H16B 104.5(15) . . ?
H16A N16 H16B 110(2) . . ?

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
N2 H2 O2 0.90(2) 2.07(2) 2.7753(18) 134.3(19) . yes
N8 H8 O4 0.84(2) 2.16(2) 2.8083(18) 134.4(18) . yes
N13 H13A O2 0.95(2) 1.87(2) 2.8017(19) 168(2) . yes
N13 H13B O4 0.94(3) 1.80(3) 2.7297(19) 172(2) . yes
N15 H15A O1 0.88(2) 2.01(2) 2.7773(18) 144.2(19) 3_666 yes
N15 H15B N16 0.91(3) 1.97(3) 2.878(2) 176(2) 1_655 yes
N15 H15C N9 0.92(2) 1.96(2) 2.845(2) 160.9(19) . yes

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
O1 C1 C2 N3 -2.4(2) . . . . ?
O1 C1 C2 N6 175.21(15) . . . . ?
O2 N6 C2 N3 178.28(14) . . . . ?
O2 N6 C2 C1 0.3(3) . . . . ?
N1 N2 C1 O1 -6.1(3) . . . . ?
N1 N2 C1 C2 173.10(15) . . . . ?
N2 C1 C2 N3 178.36(15) . . . . ?
N2 C1 C2 N6 -4.0(2) . . . . ?
N3 N4 N5 N6 -0.06(18) . . . . ?
N4 N3 C2 N6 0.12(18) . . . . ?
N4 N3 C2 C1 178.10(15) . . . . ?
N4 N5 N6 O2 -178.40(14) . . . . ?
N4 N5 N6 C2 0.13(17) . . . . ?
N5 N6 C2 N3 -0.16(18) . . . . ?
N5 N6 C2 C1 -178.10(15) . . . . ?
C2 N3 N4 N5 -0.04(18) . . . . ?
O3 C3 C4 N9 -1.2(2) . . . . ?
O3 C3 C4 N12 176.22(16) . . . . ?
O4 N12 C4 N9 -177.81(15) . . . . ?
O4 N12 C4 C3 4.4(3) . . . . ?
N7 N8 C3 O3 2.6(3) . . . . ?
N7 N8 C3 C4 -178.72(14) . . . . ?
N8 C3 C4 N9 -179.95(15) . . . . ?
N8 C3 C4 N12 -2.5(2) . . . . ?
N9 N10 N11 N12 0.30(18) . . . . ?
N10 N9 C4 N12 -0.66(18) . . . . ?
N10 N9 C4 C3 177.22(14) . . . . ?
N10 N11 N12 O4 178.04(14) . . . . ?
N10 N11 N12 C4 -0.71(18) . . . . ?
N11 N12 C4 N9 0.86(18) . . . . ?
N11 N12 C4 C3 -176.90(15) . . . . ?
C4 N9 N10 N11 0.22(19) . . . . ?

_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_YF_069_a
_database_code_depnum_ccdc_archive 'CCDC 2111832'
loop_
_audit_author_name
_audit_author_address
'Feng Yang'
;Nanjing University Of Science And Technology
China
;
_audit_update_record             
;
2021-09-25 deposited with the CCDC.	2022-06-15 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         ' C2 H3 N6 O2, C H8 N5'
_chemical_formula_sum            'C3 H11 N11 O2'
_chemical_formula_weight         233.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3985(6)
_cell_length_b                   15.6955(12)
_cell_length_c                   7.4981(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.102(3)
_cell_angle_gamma                90
_cell_volume                     954.25(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4357
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      27.25

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.135
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6362
_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            9110
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.512
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2183
_reflns_number_gt                1653
_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)+(0.0605P)²+0.1695P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2183
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 -0.03774(18) 0.73471(9) 0.2613(2) 0.0285(3) Uani 1 1 d . . . . .
C2 C -0.00626(18) 0.64421(9) 0.30526(19) 0.0281(3) Uani 1 1 d . . . . .
O1 O 0.20583(15) 0.79684(8) 0.45346(19) 0.0492(4) Uani 1 1 d . . . . .
O2 O -0.11062(14) 0.58977(7) 0.23953(17) 0.0424(3) Uani 1 1 d . . . . .
N1 N 0.06162(17) 0.79936(8) 0.33339(19) 0.0336(3) Uani 1 1 d . . . . .
N2 N -0.0121(2) 0.87223(9) 0.2645(2) 0.0472(4) Uani 1 1 d . . . . .
N3 N -0.1534(2) 0.85044(10) 0.1516(2) 0.0492(4) Uani 1 1 d . . . . .
N4 N -0.17361(17) 0.76593(9) 0.14633(19) 0.0412(4) Uani 1 1 d . . . . .
N5 N 0.13891(16) 0.62758(8) 0.42175(19) 0.0316(3) Uani 1 1 d . . . . .
H5 H 0.205(2) 0.6666(12) 0.462(3) 0.038 Uiso 1 1 d . U . . .
N6 N 0.18764(17) 0.54482(8) 0.4823(2) 0.0364(3) Uani 1 1 d . . . . .
H6A H 0.128(2) 0.5296(11) 0.563(3) 0.044 Uiso 1 1 d . U . . .
H6B H 0.160(2) 0.5112(13) 0.388(3) 0.044 Uiso 1 1 d . U . . .
C3 C 0.61069(17) 0.52281(10) 0.8533(2) 0.0282(3) Uani 1 1 d . . . . .
N7 N 0.73167(18) 0.47487(10) 0.9500(2) 0.0388(4) Uani 1 1 d . . . . .
H7A H 0.805(2) 0.4968(12) 1.044(3) 0.047 Uiso 1 1 d . U . . .
H7B H 0.720(2) 0.4219(13) 0.937(3) 0.047 Uiso 1 1 d . U . . .
N8 N 0.49462(17) 0.48988(9) 0.71798(19) 0.0347(3) Uani 1 1 d . . . . .
H8 H 0.422(2) 0.5194(13) 0.661(3) 0.042 Uiso 1 1 d . U . . .
N9 N 0.49052(19) 0.40116(9) 0.6890(2) 0.0385(4) Uani 1 1 d . . . . .
H9A H 0.399(2) 0.3840(13) 0.696(3) 0.046 Uiso 1 1 d . U . . .
H9B H 0.500(2) 0.3936(12) 0.576(3) 0.046 Uiso 1 1 d . U . . .
N10 N 0.60558(17) 0.60539(9) 0.8919(2) 0.0351(3) Uani 1 1 d . . . . .
H10 H 0.676(2) 0.6270(12) 0.966(3) 0.042 Uiso 1 1 d . U . . .
N11 N 0.4907(2) 0.65794(10) 0.7710(2) 0.0417(4) Uani 1 1 d . . . . .
H11A H 0.544(2) 0.6996(13) 0.744(3) 0.050 Uiso 1 1 d . U . . .
H11B H 0.428(2) 0.6783(13) 0.837(3) 0.050 Uiso 1 1 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 N4 1.3315(19) . ?
C1 N1 1.3353(19) . ?
C1 C2 1.466(2) . ?
C2 O2 1.2313(18) . ?
C2 N5 1.3276(19) . ?
O1 N1 1.3079(18) . ?
N1 N2 1.3385(19) . ?
N2 N3 1.311(2) . ?
N3 N4 1.337(2) . ?
N5 N6 1.4015(18) . ?
N5 H5 0.83(2) . ?
N6 H6A 0.911(19) . ?
N6 H6B 0.87(2) . ?
C3 N8 1.316(2) . ?
C3 N7 1.319(2) . ?
C3 N10 1.331(2) . ?
N7 H7A 0.88(2) . ?
N7 H7B 0.84(2) . ?
N8 N9 1.408(2) . ?
N8 H8 0.80(2) . ?
N9 H9A 0.83(2) . ?
N9 H9B 0.88(2) . ?
N10 N11 1.406(2) . ?
N10 H10 0.78(2) . ?
N11 H11A 0.85(2) . ?
N11 H11B 0.87(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 N1 108.79(14) . . ?
N4 C1 C2 125.16(14) . . ?
N1 C1 C2 126.02(13) . . ?
O2 C2 N5 124.25(14) . . ?
O2 C2 C1 120.95(13) . . ?
N5 C2 C1 114.78(13) . . ?
O1 N1 C1 128.65(12) . . ?
O1 N1 N2 122.94(13) . . ?
C1 N1 N2 108.40(14) . . ?
N3 N2 N1 106.03(14) . . ?
N2 N3 N4 111.39(13) . . ?
C1 N4 N3 105.38(14) . . ?
C2 N5 N6 122.42(13) . . ?
C2 N5 H5 120.4(12) . . ?
N6 N5 H5 117.2(13) . . ?
N5 N6 H6A 107.1(11) . . ?
N5 N6 H6B 107.8(13) . . ?
H6A N6 H6B 107.8(17) . . ?
N8 C3 N7 120.62(15) . . ?
N8 C3 N10 119.39(14) . . ?
N7 C3 N10 119.99(14) . . ?
C3 N7 H7A 119.8(13) . . ?
C3 N7 H7B 116.9(14) . . ?
H7A N7 H7B 121.1(19) . . ?
C3 N8 N9 119.39(13) . . ?
C3 N8 H8 119.7(14) . . ?
N9 N8 H8 120.5(14) . . ?
N8 N9 H9A 107.3(14) . . ?
N8 N9 H9B 106.0(12) . . ?
H9A N9 H9B 109.4(18) . . ?
C3 N10 N11 119.12(13) . . ?
C3 N10 H10 121.2(14) . . ?
N11 N10 H10 118.3(14) . . ?
N10 N11 H11A 106.9(14) . . ?
N10 N11 H11B 105.4(13) . . ?
H11A N11 H11B 107.1(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C1 C2 O2 -2.3(2) . . . . ?
N1 C1 C2 O2 175.48(14) . . . . ?
N4 C1 C2 N5 179.07(14) . . . . ?
N1 C1 C2 N5 -3.1(2) . . . . ?
N4 C1 N1 O1 179.16(15) . . . . ?
C2 C1 N1 O1 1.1(3) . . . . ?
N4 C1 N1 N2 0.37(18) . . . . ?
C2 C1 N1 N2 -177.72(14) . . . . ?
O1 N1 N2 N3 -179.35(14) . . . . ?
C1 N1 N2 N3 -0.48(18) . . . . ?
N1 N2 N3 N4 0.41(19) . . . . ?
N1 C1 N4 N3 -0.12(17) . . . . ?
C2 C1 N4 N3 177.99(14) . . . . ?
N2 N3 N4 C1 -0.19(19) . . . . ?
O2 C2 N5 N6 -0.2(3) . . . . ?
C1 C2 N5 N6 178.39(14) . . . . ?
N7 C3 N8 N9 6.6(2) . . . . ?
N10 C3 N8 N9 -173.65(15) . . . . ?
N8 C3 N10 N11 -9.2(2) . . . . ?
N7 C3 N10 N11 170.62(16) . . . . ?

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
N5 H5 O1 0.83(2) 2.045(19) 2.7131(17) 137.5(16) . yes
N6 H6A O2 0.911(19) 2.416(19) 3.1517(19) 137.8(15) 3_566 yes
N6 H6A N2 0.911(19) 2.641(19) 3.292(2) 129.0(14) 4_576 yes
N6 H6B N2 0.87(2) 2.62(2) 3.393(2) 149.3(16) 2_545 yes
N6 H6B N3 0.87(2) 2.54(2) 3.201(2) 134.0(16) 2_545 yes
N7 H7A O2 0.88(2) 2.06(2) 2.8676(19) 152.9(17) 1_656 yes
N7 H7B O1 0.84(2) 2.16(2) 2.8998(19) 147.7(19) 2_646 yes
N8 H8 N6 0.80(2) 2.11(2) 2.8529(19) 155.3(19) . yes
N9 H9A O2 0.83(2) 2.62(2) 3.373(2) 151.2(18) 3_566 yes
N10 H10 O2 0.78(2) 2.41(2) 3.0493(18) 139.5(18) 1_656 yes
N10 H10 N4 0.78(2) 2.70(2) 3.404(2) 151.6(18) 1_656 yes
N11 H11B O1 0.87(2) 2.29(2) 3.131(2) 162.2(17) 4_576 yes

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_YF_079_a
_database_code_depnum_ccdc_archive 'CCDC 2119635'
loop_
_audit_author_name
_audit_author_address
'Feng Yang'
;Nanjing University Of Science And Technology
China
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-06-15 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         'C2 H3 N6 O2, H4 N'
_chemical_formula_sum            'C2 H7 N7 O2'
_chemical_formula_weight         161.15

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                   21.016(4)
_cell_length_b                   3.6758(7)
_cell_length_c                   8.0868(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     624.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4013
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.37

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.147
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6389
_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            5864
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.179
_diffrn_reflns_theta_max         27.398
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             1371
_reflns_number_gt                1265
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_max     0.921
_reflns_Friedel_fraction_full    0.962

_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)+(0.0581P)²+0.9412P] 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_abs_structure_details 
;
 Flack x determined using 501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1371
_refine_ls_number_parameters     118
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1353
_refine_ls_wR_factor_gt          0.1325
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.042
_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 0.6040(2) 0.2097(12) 0.3379(6) 0.0271(9) Uani 1 1 d . . . . .
C2 C 0.6262(2) 0.3705(12) 0.1783(5) 0.0243(9) Uani 1 1 d . . . . .
N1 N 0.63583(18) 0.1878(11) 0.4782(5) 0.0300(9) Uani 1 1 d . . . . .
N2 N 0.59764(18) 0.0259(11) 0.5905(5) 0.0291(9) Uani 1 1 d . . . . .
N3 N 0.5446(2) -0.0518(13) 0.5167(6) 0.0397(11) Uani 1 1 d . . . . .
N4 N 0.5450(2) 0.0596(12) 0.3600(5) 0.0356(10) Uani 1 1 d . . . . .
N5 N 0.58067(17) 0.3703(11) 0.0658(4) 0.0259(8) Uani 1 1 d . . . . .
H5 H 0.543860 0.281421 0.088642 0.031 Uiso 1 1 calc R U . . .
N6 N 0.5929(2) 0.5172(14) -0.0922(5) 0.0317(9) Uani 1 1 d . . . . .
H6A H 0.565(3) 0.670(17) -0.124(8) 0.038 Uiso 1 1 d . U . . .
H6B H 0.594(3) 0.347(17) -0.167(10) 0.038 Uiso 1 1 d . U . . .
O1 O 0.69252(16) 0.2958(10) 0.5174(5) 0.0379(9) Uani 1 1 d . . . . .
O2 O 0.67973(15) 0.4864(12) 0.1579(4) 0.0390(9) Uani 1 1 d . . . . .
N7 N 0.72268(18) 0.8654(12) 0.8291(6) 0.0340(9) Uani 1 1 d D . . . .
H7A H 0.712(2) 0.967(12) 0.752(4) 0.041 Uiso 1 1 d D U . . .
H7B H 0.7455(19) 0.709(10) 0.803(6) 0.041 Uiso 1 1 d D U . . .
H7C H 0.741(2) 0.997(11) 0.886(5) 0.041 Uiso 1 1 d D U . . .
H7D H 0.6945(18) 0.781(12) 0.875(5) 0.041 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 1.320(6) . ?
C1 N4 1.368(6) . ?
C1 C2 1.495(6) . ?
C2 O2 1.213(5) . ?
C2 N5 1.321(6) . ?
N1 O1 1.295(5) . ?
N1 N2 1.350(5) . ?
N2 N3 1.297(6) . ?
N3 N4 1.332(6) . ?
N5 N6 1.410(5) . ?
N5 H5 0.8600 . ?
N6 H6A 0.85(6) . ?
N6 H6B 0.87(7) . ?
N7 H7A 0.76(3) . ?
N7 H7B 0.78(3) . ?
N7 H7C 0.77(3) . ?
N7 H7D 0.76(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
N1 C1 N4 108.8(4) . . ?
N1 C1 C2 127.4(4) . . ?
N4 C1 C2 123.8(4) . . ?
O2 C2 N5 125.3(4) . . ?
O2 C2 C1 123.1(4) . . ?
N5 C2 C1 111.6(4) . . ?
O1 N1 C1 131.2(4) . . ?
O1 N1 N2 121.1(4) . . ?
C1 N1 N2 107.7(4) . . ?
N3 N2 N1 107.4(4) . . ?
N2 N3 N4 111.3(4) . . ?
N3 N4 C1 104.8(4) . . ?
C2 N5 N6 119.4(3) . . ?
C2 N5 H5 120.3 . . ?
N6 N5 H5 120.3 . . ?
N5 N6 H6A 114(4) . . ?
N5 N6 H6B 111(5) . . ?
H6A N6 H6B 107(6) . . ?
H7A N7 H7B 109(3) . . ?
H7A N7 H7C 109(3) . . ?
H7B N7 H7C 109(3) . . ?
H7A N7 H7D 111(3) . . ?
H7B N7 H7D 108(3) . . ?
H7C N7 H7D 110(3) . . ?

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 O2 4.1(8) . . . . ?
N4 C1 C2 O2 -176.2(5) . . . . ?
N1 C1 C2 N5 -175.6(4) . . . . ?
N4 C1 C2 N5 4.1(7) . . . . ?
N4 C1 N1 O1 -179.1(4) . . . . ?
C2 C1 N1 O1 0.6(8) . . . . ?
N4 C1 N1 N2 -0.3(5) . . . . ?
C2 C1 N1 N2 179.5(4) . . . . ?
O1 N1 N2 N3 -179.9(4) . . . . ?
C1 N1 N2 N3 1.1(5) . . . . ?
N1 N2 N3 N4 -1.5(6) . . . . ?
N2 N3 N4 C1 1.3(6) . . . . ?
N1 C1 N4 N3 -0.6(5) . . . . ?
C2 C1 N4 N3 179.6(4) . . . . ?
O2 C2 N5 N6 -0.6(7) . . . . ?
C1 C2 N5 N6 179.1(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
N5 H5 N3 0.86 2.12 2.908(5) 151.6 2_654 yes
N6 H6A N4 0.85(6) 2.53(6) 3.313(7) 155(5) 2_664 yes
N6 H6B N2 0.87(7) 2.29(8) 3.139(6) 165(6) 1_554 yes
N7 H7A O1 0.76(3) 2.28(3) 3.043(6) 172(5) 1_565 yes
N7 H7B O1 0.78(3) 2.65(4) 3.143(6) 123(4) 3_655 yes
N7 H7B O2 0.78(3) 2.12(3) 2.840(5) 153(4) 3_655 yes
N7 H7C O1 0.77(3) 2.07(3) 2.828(6) 167(5) 3_665 yes
N7 H7D N6 0.76(3) 2.36(3) 3.079(6) 157(4) 1_556 yes
N7 H7D O2 0.76(3) 2.55(4) 3.134(6) 134(4) 1_556 yes

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_YF_078_a
_database_code_depnum_ccdc_archive 'CCDC 2119636'
loop_
_audit_author_name
_audit_author_address
'Feng Yang'
;Nanjing University Of Science And Technology
China
;
_audit_update_record             
;
2021-11-02 deposited with the CCDC.	2022-06-15 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         'C2 H3 N6 O2, C H9 N6, H2 O'
_chemical_formula_sum            'C3 H14 N12 O3'
_chemical_formula_weight         266.26

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                   7.2673(5)
_cell_length_b                   7.5778(5)
_cell_length_c                   11.4906(7)
_cell_angle_alpha                99.301(2)
_cell_angle_beta                 99.086(2)
_cell_angle_gamma                113.948(2)
_cell_volume                     552.91(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5505
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.58

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6879
_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            8535
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.038
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2530
_reflns_number_gt                2144
_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)+(0.0611P)²+0.1266P] 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         2530
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 1.06481(19) 0.77352(18) 0.68141(11) 0.0258(3) Uani 1 1 d . . . . .
C2 C 1.04087(19) 0.79343(18) 0.55474(11) 0.0251(3) Uani 1 1 d . . . . .
C3 C 0.32084(19) 0.11528(19) 0.21755(11) 0.0258(3) Uani 1 1 d . . . . .
N1 N 0.94673(16) 0.61774(15) 0.72108(9) 0.0272(2) Uani 1 1 d . . . . .
N2 N 1.01945(19) 0.65606(18) 0.84112(10) 0.0356(3) Uani 1 1 d . . . . .
N3 N 1.1786(2) 0.83442(19) 0.87291(11) 0.0398(3) Uani 1 1 d . . . . .
N4 N 1.20938(18) 0.90998(17) 0.77636(10) 0.0347(3) Uani 1 1 d . . . . .
N5 N 0.86853(17) 0.65231(16) 0.47639(9) 0.0289(3) Uani 1 1 d . . . . .
H5 H 0.782095 0.560800 0.502580 0.035 Uiso 1 1 calc R U . . .
N6 N 0.8230(2) 0.64790(19) 0.35183(10) 0.0339(3) Uani 1 1 d . . . . .
H6A H 0.938(3) 0.671(3) 0.3305(17) 0.047(5) Uiso 1 1 d . . . . .
H6B H 0.801(3) 0.760(3) 0.3502(18) 0.065(6) Uiso 1 1 d . . . . .
N7 N 0.45796(18) 0.27951(17) 0.19855(9) 0.0315(3) Uani 1 1 d . . . . .
H7 H 0.558123 0.368341 0.257370 0.038 Uiso 1 1 calc R U . . .
N8 N 0.4360(2) 0.3056(2) 0.07900(10) 0.0364(3) Uani 1 1 d . . . . .
H8A H 0.448(3) 0.427(3) 0.0869(17) 0.049(5) Uiso 1 1 d . . . . .
H8B H 0.544(3) 0.297(3) 0.0512(18) 0.050(5) Uiso 1 1 d . . . . .
N9 N 0.17018(19) -0.02155(17) 0.12470(10) 0.0344(3) Uani 1 1 d . . . . .
H9 H 0.155268 -0.000250 0.053307 0.041 Uiso 1 1 calc R U . . .
N10 N 0.0352(2) -0.20240(19) 0.14558(12) 0.0392(3) Uani 1 1 d . . . . .
H10B H -0.084(3) -0.231(3) 0.105(2) 0.062(6) Uiso 1 1 d . . . . .
H10A H 0.076(3) -0.298(3) 0.117(2) 0.068(6) Uiso 1 1 d . . . . .
N11 N 0.33173(18) 0.08686(18) 0.32927(10) 0.0337(3) Uani 1 1 d . . . . .
H11 H 0.240295 -0.018664 0.342013 0.040 Uiso 1 1 calc R U . . .
N12 N 0.49444(18) 0.23134(19) 0.42620(10) 0.0325(3) Uani 1 1 d . . . . .
H12B H 0.575(3) 0.172(3) 0.4540(17) 0.050(5) Uiso 1 1 d . . . . .
H12A H 0.436(3) 0.251(3) 0.4848(18) 0.052(5) Uiso 1 1 d . . . . .
O1 O 0.78870(15) 0.44956(14) 0.65837(9) 0.0386(3) Uani 1 1 d . . . . .
O2 O 1.17377(14) 0.93270(14) 0.52791(9) 0.0338(2) Uani 1 1 d . . . . .
O3 O 0.5711(2) 0.30141(19) 0.83869(11) 0.0493(3) Uani 1 1 d . . . . .
H3A H 0.622(4) 0.337(4) 0.781(2) 0.071(7) Uiso 1 1 d . . . . .
H3B H 0.475(4) 0.190(4) 0.806(2) 0.069(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N4 1.3247(17) . ?
C1 N1 1.3464(16) . ?
C1 C2 1.4777(17) . ?
C2 O2 1.2302(15) . ?
C2 N5 1.3297(16) . ?
C3 N7 1.3188(17) . ?
C3 N9 1.3282(17) . ?
C3 N11 1.3311(15) . ?
N1 O1 1.3100(14) . ?
N1 N2 1.3349(15) . ?
N2 N3 1.3176(17) . ?
N3 N4 1.3373(16) . ?
N5 N6 1.4089(14) . ?
N5 H5 0.8600 . ?
N6 H6A 0.87(2) . ?
N6 H6B 0.93(2) . ?
N7 N8 1.4128(14) . ?
N7 H7 0.8600 . ?
N8 H8A 0.88(2) . ?
N8 H8B 0.91(2) . ?
N9 N10 1.4096(16) . ?
N9 H9 0.8600 . ?
N10 H10B 0.84(2) . ?
N10 H10A 0.92(2) . ?
N11 N12 1.4058(15) . ?
N11 H11 0.8600 . ?
N12 H12B 0.919(19) . ?
N12 H12A 0.88(2) . ?
O3 H3A 0.84(2) . ?
O3 H3B 0.82(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 N1 108.20(11) . . ?
N4 C1 C2 124.83(11) . . ?
N1 C1 C2 126.97(11) . . ?
O2 C2 N5 124.57(11) . . ?
O2 C2 C1 120.57(12) . . ?
N5 C2 C1 114.86(10) . . ?
N7 C3 N9 119.70(11) . . ?
N7 C3 N11 120.37(12) . . ?
N9 C3 N11 119.93(12) . . ?
O1 N1 N2 122.28(10) . . ?
O1 N1 C1 128.95(10) . . ?
N2 N1 C1 108.74(11) . . ?
N3 N2 N1 105.85(10) . . ?
N2 N3 N4 111.09(11) . . ?
C1 N4 N3 106.11(11) . . ?
C2 N5 N6 122.11(10) . . ?
C2 N5 H5 118.9 . . ?
N6 N5 H5 118.9 . . ?
N5 N6 H6A 105.1(12) . . ?
N5 N6 H6B 104.3(13) . . ?
H6A N6 H6B 106.4(18) . . ?
C3 N7 N8 118.24(11) . . ?
C3 N7 H7 120.9 . . ?
N8 N7 H7 120.9 . . ?
N7 N8 H8A 104.9(12) . . ?
N7 N8 H8B 107.7(12) . . ?
H8A N8 H8B 109.8(17) . . ?
C3 N9 N10 118.63(11) . . ?
C3 N9 H9 120.7 . . ?
N10 N9 H9 120.7 . . ?
N9 N10 H10B 106.2(15) . . ?
N9 N10 H10A 107.6(14) . . ?
H10B N10 H10A 110(2) . . ?
C3 N11 N12 119.23(11) . . ?
C3 N11 H11 120.4 . . ?
N12 N11 H11 120.4 . . ?
N11 N12 H12B 106.7(12) . . ?
N11 N12 H12A 105.6(13) . . ?
H12B N12 H12A 105.3(17) . . ?
H3A O3 H3B 104(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
N4 C1 C2 O2 9.0(2) . . . . ?
N1 C1 C2 O2 -171.21(12) . . . . ?
N4 C1 C2 N5 -170.82(12) . . . . ?
N1 C1 C2 N5 9.02(19) . . . . ?
N4 C1 N1 O1 -178.92(12) . . . . ?
C2 C1 N1 O1 1.2(2) . . . . ?
N4 C1 N1 N2 -0.75(15) . . . . ?
C2 C1 N1 N2 179.40(12) . . . . ?
O1 N1 N2 N3 178.91(12) . . . . ?
C1 N1 N2 N3 0.60(15) . . . . ?
N1 N2 N3 N4 -0.24(16) . . . . ?
N1 C1 N4 N3 0.58(15) . . . . ?
C2 C1 N4 N3 -179.56(12) . . . . ?
N2 N3 N4 C1 -0.21(16) . . . . ?
O2 C2 N5 N6 1.0(2) . . . . ?
C1 C2 N5 N6 -179.24(11) . . . . ?
N9 C3 N7 N8 1.43(19) . . . . ?
N11 C3 N7 N8 -178.02(12) . . . . ?
N7 C3 N9 N10 175.17(13) . . . . ?
N11 C3 N9 N10 -5.4(2) . . . . ?
N7 C3 N11 N12 -1.75(19) . . . . ?
N9 C3 N11 N12 178.80(12) . . . . ?

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
O3 H3A O1 0.84(2) 2.07(2) 2.8983(16) 171(2) . yes
N5 H5 N12 0.86 2.42 3.1256(16) 139.9 . yes
N5 H5 O1 0.86 2.10 2.7870(14) 136.4 . yes
N7 H7 N6 0.86 2.16 2.9758(16) 158.7 . yes
N9 H9 N3 0.86 2.31 2.9419(17) 130.4 1_444 yes
N11 H11 O2 0.86 2.32 2.9143(14) 126.8 1_445 yes
N6 H6A N1 0.87(2) 2.658(19) 3.1918(18) 120.9(15) 2_766 yes
N6 H6A N10 0.87(2) 2.552(19) 3.1442(17) 126.3(15) 1_665 yes
N6 H6A O1 0.87(2) 2.494(19) 3.2081(18) 140.0(16) 2_766 yes
N8 H8A O3 0.88(2) 2.16(2) 2.9988(19) 159.1(17) 2_666 yes
N12 H12B O2 0.919(19) 2.26(2) 3.1434(16) 160.0(16) 2_766 yes
N6 H6B O2 0.93(2) 2.44(2) 3.2434(17) 145.4(17) 2_776 yes
N8 H8B N3 0.91(2) 2.679(18) 3.375(2) 133.6(15) 2_766 yes
N8 H8B O3 0.91(2) 2.48(2) 3.0730(17) 122.4(14) 1_554 yes
N10 H10A N2 0.92(2) 2.66(2) 3.3285(18) 130.0(17) 2_656 yes
N10 H10A O3 0.92(2) 2.55(2) 3.225(2) 130.7(17) 2_656 yes
N12 H12A O2 0.88(2) 2.58(2) 3.0581(14) 115.4(15) 1_445 yes
O3 H3B N4 0.82(2) 2.14(2) 2.9343(17) 163(2) 1_445 yes

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_YF_075_a
_database_code_depnum_ccdc_archive 'CCDC 2115133'
loop_
_audit_author_name
_audit_author_address
'Feng Yang'
;Nanjing University Of Science And Technology
China
;
_audit_update_record             
;
2021-10-12 deposited with the CCDC.	2022-06-15 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         '2(C2 H4 N6 O2), 3(H2 O)'
_chemical_formula_sum            'C4 H14 N12 O7'
_chemical_formula_weight         342.27

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                   8.5771(4)
_cell_length_b                   8.9197(4)
_cell_length_c                   9.7491(5)
_cell_angle_alpha                70.6800(10)
_cell_angle_beta                 71.5520(10)
_cell_angle_gamma                77.6680(10)
_cell_volume                     662.73(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6745
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6692
_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            10488
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.297
_diffrn_reflns_theta_max         28.377
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3305
_reflns_number_gt                2833
_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)+(0.0654P)²+0.1471P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3305
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1020
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.59754(14) 0.64507(14) -0.14774(13) 0.0233(2) Uani 1 1 d . . . . .
C2 C 0.47794(15) 0.77695(15) -0.10206(13) 0.0252(2) Uani 1 1 d . . . . .
C3 C -0.06549(13) 0.80949(13) 0.60350(12) 0.0202(2) Uani 1 1 d . . . . .
C4 C 0.07580(14) 0.70526(13) 0.65542(13) 0.0216(2) Uani 1 1 d . . . . .
N1 N 0.61103(12) 0.58649(12) -0.26202(11) 0.0237(2) Uani 1 1 d . . . . .
N2 N 0.73770(14) 0.46929(14) -0.26540(14) 0.0339(3) Uani 1 1 d . . . . .
N3 N 0.79862(15) 0.45828(14) -0.15382(14) 0.0364(3) Uani 1 1 d . . . . .
N4 N 0.71478(14) 0.56554(14) -0.07950(13) 0.0311(2) Uani 1 1 d . . . . .
N5 N 0.36619(13) 0.84205(13) -0.18066(12) 0.0280(2) Uani 1 1 d . . . . .
H5 H 0.363959 0.807570 -0.252544 0.034 Uiso 1 1 calc R U . . .
N6 N 0.25165(14) 0.97004(14) -0.14082(12) 0.0315(3) Uani 1 1 d . . . . .
H6A H 0.220260 0.949906 -0.040925 0.047 Uiso 1 1 calc R U . . .
H6B H 0.163572 0.980923 -0.174449 0.047 Uiso 1 1 calc R U . . .
H6C H 0.298911 1.060001 -0.181948 0.047 Uiso 1 1 calc R U . . .
N7 N -0.12338(12) 0.80407(12) 0.49249(11) 0.0220(2) Uani 1 1 d . . . . .
N8 N -0.24853(13) 0.92226(13) 0.47542(13) 0.0293(2) Uani 1 1 d . . . . .
N9 N -0.26509(13) 0.99607(13) 0.57678(13) 0.0293(2) Uani 1 1 d . . . . .
N10 N -0.15464(13) 0.92905(12) 0.65754(12) 0.0258(2) Uani 1 1 d . . . . .
N11 N 0.15306(12) 0.60167(12) 0.57499(12) 0.0243(2) Uani 1 1 d . . . . .
H11 H 0.126542 0.605930 0.495654 0.029 Uiso 1 1 calc R U . . .
N12 N 0.27923(12) 0.48529(12) 0.62400(12) 0.0258(2) Uani 1 1 d . . . . .
H12A H 0.353254 0.533198 0.635638 0.039 Uiso 1 1 calc R U . . .
H12B H 0.328773 0.432239 0.555647 0.039 Uiso 1 1 calc R U . . .
H12C H 0.235151 0.417130 0.711588 0.039 Uiso 1 1 calc R U . . .
O1 O 0.52529(11) 0.63342(11) -0.36308(10) 0.0304(2) Uani 1 1 d . . . . .
O2 O 0.48354(15) 0.82257(15) 0.00051(13) 0.0494(3) Uani 1 1 d . . . . .
O3 O -0.07188(12) 0.70481(11) 0.40982(11) 0.0311(2) Uani 1 1 d . . . . .
O4 O 0.11704(12) 0.71662(12) 0.75975(11) 0.0356(2) Uani 1 1 d . . . . .
O5 O 0.52635(13) 0.79529(13) 0.28287(12) 0.0401(3) Uani 1 1 d G . . . .
H5A H 0.490536 0.793051 0.211720 0.060 Uiso 1 1 d G U . . .
H5B H 0.447949 0.848216 0.332939 0.060 Uiso 1 1 d G U . . .
O6 O 0.87026(14) 0.69990(14) 0.09264(13) 0.0433(3) Uani 1 1 d G . . . .
H6D H 0.975061 0.678245 0.070378 0.065 Uiso 1 1 d G U . . .
H6E H 0.840904 0.669400 0.031612 0.065 Uiso 1 1 d G U . . .
O7 O 0.91955(13) 0.06809(12) 0.84415(11) 0.0347(2) Uani 1 1 d G . . . .
H7A H 0.885991 0.024804 0.794723 0.052 Uiso 1 1 d G U . . .
H7B H 0.941695 0.159286 0.783811 0.052 Uiso 1 1 d G 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 N4 1.3279(16) . ?
C1 N1 1.3438(15) . ?
C1 C2 1.4753(17) . ?
C2 O2 1.2149(15) . ?
C2 N5 1.3325(15) . ?
C3 N10 1.3297(14) . ?
C3 N7 1.3435(15) . ?
C3 C4 1.4780(16) . ?
C4 O4 1.2170(14) . ?
C4 N11 1.3405(15) . ?
N1 O1 1.3194(13) . ?
N1 N2 1.3376(15) . ?
N2 N3 1.3165(17) . ?
N3 N4 1.3389(17) . ?
N5 N6 1.4115(14) . ?
N5 H5 0.8600 . ?
N6 H6A 0.8900 . ?
N6 H6B 0.8900 . ?
N6 H6C 0.8900 . ?
N7 O3 1.3070(13) . ?
N7 N8 1.3435(14) . ?
N8 N9 1.3160(16) . ?
N9 N10 1.3392(15) . ?
N11 N12 1.4129(13) . ?
N11 H11 0.8600 . ?
N12 H12A 0.8900 . ?
N12 H12B 0.8900 . ?
N12 H12C 0.8900 . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8500 . ?
O6 H6D 0.8500 . ?
O6 H6E 0.8501 . ?
O7 H7A 0.8500 . ?
O7 H7B 0.8500 . ?

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
N4 C1 N1 108.55(11) . . ?
N4 C1 C2 123.51(11) . . ?
N1 C1 C2 127.93(11) . . ?
O2 C2 N5 122.90(12) . . ?
O2 C2 C1 121.22(12) . . ?
N5 C2 C1 115.88(10) . . ?
N10 C3 N7 108.22(10) . . ?
N10 C3 C4 125.00(10) . . ?
N7 C3 C4 126.75(10) . . ?
O4 C4 N11 124.49(11) . . ?
O4 C4 C3 122.11(11) . . ?
N11 C4 C3 113.39(10) . . ?
O1 N1 N2 122.10(10) . . ?
O1 N1 C1 129.41(10) . . ?
N2 N1 C1 108.43(10) . . ?
N3 N2 N1 106.11(10) . . ?
N2 N3 N4 111.06(11) . . ?
C1 N4 N3 105.85(11) . . ?
C2 N5 N6 117.10(10) . . ?
C2 N5 H5 121.4 . . ?
N6 N5 H5 121.4 . . ?
N5 N6 H6A 109.5 . . ?
N5 N6 H6B 109.5 . . ?
H6A N6 H6B 109.5 . . ?
N5 N6 H6C 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
O3 N7 C3 128.38(10) . . ?
O3 N7 N8 122.86(10) . . ?
C3 N7 N8 108.76(10) . . ?
N9 N8 N7 105.73(10) . . ?
N8 N9 N10 111.23(10) . . ?
C3 N10 N9 106.06(10) . . ?
C4 N11 N12 118.24(10) . . ?
C4 N11 H11 120.9 . . ?
N12 N11 H11 120.9 . . ?
N11 N12 H12A 109.5 . . ?
N11 N12 H12B 109.5 . . ?
H12A N12 H12B 109.5 . . ?
N11 N12 H12C 109.5 . . ?
H12A N12 H12C 109.5 . . ?
H12B N12 H12C 109.5 . . ?
H5A O5 H5B 104.5 . . ?
H6D O6 H6E 104.5 . . ?
H7A O7 H7B 104.5 . . ?

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
N4 C1 C2 O2 1.7(2) . . . . ?
N1 C1 C2 O2 -176.99(13) . . . . ?
N4 C1 C2 N5 -178.76(11) . . . . ?
N1 C1 C2 N5 2.53(18) . . . . ?
N10 C3 C4 O4 3.78(18) . . . . ?
N7 C3 C4 O4 -178.23(11) . . . . ?
N10 C3 C4 N11 -175.09(10) . . . . ?
N7 C3 C4 N11 2.89(17) . . . . ?
N4 C1 N1 O1 -177.01(11) . . . . ?
C2 C1 N1 O1 1.9(2) . . . . ?
N4 C1 N1 N2 0.02(14) . . . . ?
C2 C1 N1 N2 178.89(11) . . . . ?
O1 N1 N2 N3 177.41(10) . . . . ?
C1 N1 N2 N3 0.12(14) . . . . ?
N1 N2 N3 N4 -0.21(14) . . . . ?
N1 C1 N4 N3 -0.14(14) . . . . ?
C2 C1 N4 N3 -179.07(11) . . . . ?
N2 N3 N4 C1 0.22(14) . . . . ?
O2 C2 N5 N6 0.39(19) . . . . ?
C1 C2 N5 N6 -179.12(10) . . . . ?
N10 C3 N7 O3 -179.73(10) . . . . ?
C4 C3 N7 O3 2.01(19) . . . . ?
N10 C3 N7 N8 0.73(13) . . . . ?
C4 C3 N7 N8 -177.53(10) . . . . ?
O3 N7 N8 N9 179.93(10) . . . . ?
C3 N7 N8 N9 -0.50(13) . . . . ?
N7 N8 N9 N10 0.09(13) . . . . ?
N7 C3 N10 N9 -0.65(13) . . . . ?
C4 C3 N10 N9 177.65(10) . . . . ?
N8 N9 N10 C3 0.35(13) . . . . ?
O4 C4 N11 N12 7.47(18) . . . . ?
C3 C4 N11 N12 -173.68(9) . . . . ?

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
N5 H5 O1 0.86 2.18 2.8384(13) 133.6 . yes
N5 H5 O4 0.86 2.38 2.8971(14) 119.0 1_554 yes
N6 H6A O7 0.89 1.89 2.7407(14) 159.7 2_666 yes
N6 H6B N8 0.89 2.67 3.0880(15) 109.9 2_575 yes
N6 H6B O7 0.89 2.04 2.8311(15) 146.9 1_464 yes
N6 H6C O5 0.89 1.98 2.8356(17) 159.9 2_675 yes
N6 H6C O6 0.89 2.56 3.0447(16) 114.9 2_675 yes
N11 H11 N2 0.86 2.42 3.0999(16) 136.4 2_665 yes
N11 H11 O3 0.86 2.04 2.7184(13) 135.6 . yes
N12 H12A O1 0.89 1.89 2.7722(13) 173.1 1_556 yes
N12 H12B O1 0.89 2.09 2.9543(14) 164.0 2_665 yes
N12 H12C O6 0.89 1.88 2.7655(16) 171.4 2_666 yes

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.051

