# 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 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_7_a
_database_code_depnum_ccdc_archive 'CCDC 1945173'
loop_
_audit_author_name
_audit_author_address
'Qian Wang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2022-02-21 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 N3 O6, H3 O'
_chemical_formula_sum            'C5 H5 N3 O7'
_chemical_formula_weight         219.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   7.259(4)
_cell_length_b                   7.067(4)
_cell_length_c                   8.126(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.221(15)
_cell_angle_gamma                90
_cell_volume                     408.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    867
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.69

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_F_000             224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5586
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1606
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.555
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_point_group_measured_fraction_full 0.915
_reflns_number_total             864
_reflns_number_gt                628
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_max     0.832
_reflns_Friedel_fraction_full    0.840

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0663P)²+0.2715P] 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 202 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         864
_refine_ls_number_parameters     74
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.063
_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 0.4444(8) 0.5576(7) 0.1241(7) 0.0360(13) Uani 1 1 d . . . . .
C2 C 0.500000 0.6766(10) 0.000000 0.0323(17) Uani 1 2 d S T P . .
C3 C 0.4625(7) 0.3640(8) 0.0835(5) 0.0331(11) Uani 1 1 d D . . . .
N1 N 0.3753(7) 0.6225(7) 0.2630(6) 0.0397(12) Uani 1 1 d . . . . .
N2 N 0.500000 0.8617(9) 0.000000 0.0440(17) Uani 1 2 d S T P . .
H2A H 0.535827 0.922543 -0.079878 0.053 Uiso 0.5 1 calc R U P . .
H2B H 0.464173 0.922543 0.079878 0.053 Uiso 0.5 1 calc R U P . .
O1 O 0.3613(7) 0.7964(5) 0.2840(6) 0.0558(14) Uani 1 1 d . . . . .
O2 O 0.3253(7) 0.5059(6) 0.3582(5) 0.0524(12) Uani 1 1 d . . . . .
O3 O 0.4295(5) 0.2170(6) 0.1517(4) 0.0425(10) Uani 1 1 d . . . . .
O4 O 0.500000 0.1380(9) 0.500000 0.0680(19) Uani 1 2 d DS T P . .
H4A H 0.486(13) 0.180(7) 0.397(5) 0.102 Uiso 1 1 d D U . . .
H4B H 0.500000 0.018(4) 0.500000 0.102 Uiso 1 2 d DS U P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.052(3) 0.024(3) 0.033(3) -0.003(2) 0.011(2) 0.002(2)
C2 0.039(4) 0.023(5) 0.037(4) 0.000 0.012(3) 0.000
C3 0.042(3) 0.029(3) 0.029(3) -0.003(2) 0.006(2) 0.000(2)
N1 0.052(3) 0.033(3) 0.037(3) 0.000(2) 0.015(2) 0.002(2)
N2 0.062(4) 0.025(4) 0.047(4) 0.000 0.017(3) 0.000
O1 0.080(4) 0.029(3) 0.061(3) -0.011(2) 0.021(3) 0.003(2)
O2 0.082(3) 0.039(2) 0.043(2) 0.0042(19) 0.031(2) 0.010(2)
O3 0.071(2) 0.025(2) 0.035(2) 0.0057(19) 0.0173(16) -0.0010(19)
O4 0.111(5) 0.050(4) 0.048(4) 0.000 0.026(4) 0.000

_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 1.399(7) . ?
C1 C3 1.419(8) . ?
C1 C2 1.430(7) . ?
C2 N2 1.308(10) . ?
C3 O3 1.223(6) . ?
C3 C3 1.557(8) 2_655 ?
N1 O2 1.232(7) . ?
N1 O1 1.248(6) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
O4 H4A 0.88(2) . ?
O4 H4B 0.85(3) . ?
O4 H4A 0.88(2) 2_656 ?

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 C3 124.6(5) . . ?
N1 C1 C2 124.8(4) . . ?
C3 C1 C2 110.6(5) . . ?
N2 C2 C1 126.0(3) . 2_655 ?
N2 C2 C1 126.0(3) . . ?
C1 C2 C1 108.0(6) 2_655 . ?
O3 C3 C1 132.7(4) . . ?
O3 C3 C3 121.8(3) . 2_655 ?
C1 C3 C3 105.4(3) . 2_655 ?
O2 N1 O1 122.1(5) . . ?
O2 N1 C1 118.9(5) . . ?
O1 N1 C1 119.0(5) . . ?
C2 N2 H2A 120.0 . . ?
C2 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
H4A O4 H4B 110(4) . . ?
H4A O4 H4A 140(8) . 2_656 ?
H4B O4 H4A 110(4) . 2_656 ?

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 2.1(7) . . . . ?
C3 C1 C2 N2 180.0(3) . . . . ?
N1 C1 C2 C1 -177.9(7) . . . 2_655 ?
C3 C1 C2 C1 0.0(3) . . . 2_655 ?
N1 C1 C3 O3 -1.2(9) . . . . ?
C2 C1 C3 O3 -179.1(6) . . . . ?
N1 C1 C3 C3 177.9(6) . . . 2_655 ?
C2 C1 C3 C3 0.0(6) . . . 2_655 ?
C3 C1 N1 O2 -0.3(8) . . . . ?
C2 C1 N1 O2 177.4(5) . . . . ?
C3 C1 N1 O1 -178.3(6) . . . . ?
C2 C1 N1 O1 -0.6(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
N2 H2B O1 0.86 2.14 2.731(5) 125.4 . yes
N2 H2B O3 0.86 2.19 2.887(7) 138.1 1_565 yes
N2 H2A O1 0.86 2.14 2.731(5) 125.4 2_655 yes
N2 H2A O3 0.86 2.19 2.887(7) 138.1 2_665 yes
O4 H4A O2 0.88(2) 2.57(6) 3.021(8) 113(5) . yes
O4 H4A O3 0.88(2) 1.97(3) 2.832(4) 167(6) . yes
O4 H4B O1 0.85(3) 2.420(18) 3.038(7) 130.3(5) 1_545 yes
O4 H4B O1 0.85(3) 2.420(18) 3.038(7) 130.3(5) 2_646 yes

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.069

_shelx_res_file                  
;
TITL 7_a.res in C2
    7_a.res
    created by SHELXL-2018/3 at 11:25:32 on 26-Apr-2019
CELL 0.71073 7.2593 7.0668 8.1264 90.000 101.221 90.000
ZERR 2.00 0.0040 0.0037 0.0039 0.000 0.015 0.000
LATT -7
SYMM -x, y, -z
SFAC C  H  N  O
UNIT 10  10  6  14
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN -5
size 0.08 0.06 0.02
CONF
HTAB
HTAB N2 O1
EQIV $3 x, y+1, z
HTAB N2 O3_$3
EQIV $1 -x+1, y, -z
HTAB N2 O1_$1
EQIV $4 -x+1, y+1, -z
HTAB N2 O3_$4
HTAB O4 O2
HTAB O4 O3
EQIV $5 x, y-1, z
HTAB O4 O1_$5
EQIV $6 -x+1, y-1, -z+1
HTAB O4 O1_$6
dfix 1.53 0.01 c3 C3_$1
DFIX 0.85 O4 H4A O4 H4B
DFIX 1.39 H4A H4B
TEMP 23.000
WGHT    0.066300    0.271500
FVAR       1.58865
C1    1    0.444362    0.557630    0.124057    11.00000    0.05184    0.02432 =
         0.03308   -0.00258    0.01113    0.00217
C2    1    0.500000    0.676596    0.000000    10.50000    0.03909    0.02326 =
         0.03650    0.00000    0.01194    0.00000
C3    1    0.462508    0.364040    0.083493    11.00000    0.04178    0.02855 =
         0.02870   -0.00333    0.00589    0.00042
N1    3    0.375316    0.622513    0.262994    11.00000    0.05158    0.03266 =
         0.03739   -0.00017    0.01519    0.00225
N2    3    0.500000    0.861695    0.000000    10.50000    0.06216    0.02491 =
         0.04723    0.00000    0.01655    0.00000
AFIX  93
H2A   2    0.535827    0.922543   -0.079878    10.50000   -1.20000
H2B   2    0.464173    0.922543    0.079878    10.50000   -1.20000
AFIX   0
O1    4    0.361307    0.796443    0.284012    11.00000    0.08002    0.02912 =
         0.06125   -0.01092    0.02122    0.00341
O2    4    0.325345    0.505942    0.358175    11.00000    0.08230    0.03931 =
         0.04324    0.00423    0.03093    0.00979
O3    4    0.429533    0.217024    0.151723    11.00000    0.07136    0.02457 =
         0.03453    0.00574    0.01731   -0.00104
O4    4    0.500000    0.137994    0.500000    10.50000    0.11058    0.04974 =
         0.04783    0.00000    0.02556    0.00000
H4A   2    0.486431    0.180291    0.396987    11.00000   -1.50000
H4B   2    0.500000    0.017963    0.500000    10.50000   -1.50000
HKLF 4 1 1 0 0 0 1 0 0 0 1




REM  7_a.res in C2
REM wR2 = 0.1395, GooF = S = 1.060, Restrained GooF = 1.063 for all data
REM R1 = 0.0609 for 628 Fo > 4sig(Fo) and 0.0901 for all 864 data
REM 74 parameters refined using 5 restraints

END

WGHT      0.0676      0.2910

REM Instructions for potential hydrogen bonds
HTAB N2 O1_$1
HTAB N2 O3_$4
HTAB N2 O1
HTAB N2 O3_$3
HTAB O4 O2
HTAB O4 O3
HTAB O4 O1_$5
HTAB O4 O1_$6

REM Highest difference peak  0.230,  deepest hole -0.314,  1-sigma level  0.069
Q1    1   0.3018  1.0009  0.3830  11.00000  0.05    0.23
Q2    1   0.1428  0.9300  0.3526  11.00000  0.05    0.21
Q3    1   0.1694  0.5365  0.1215  11.00000  0.05    0.21
Q4    1   0.6482  0.8587  0.1441  11.00000  0.05    0.19
Q5    1   0.1163  0.6121  0.1814  11.00000  0.05    0.19
;
_shelx_res_checksum              54074
####################################################################### 
# 
# 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_Wq190425_1_a
_database_code_depnum_ccdc_archive 'CCDC 1945175'
loop_
_audit_author_name
_audit_author_address
'Qian Wang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2019-08-04 deposited with the CCDC.	2022-02-21 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 N3 O6, H4 N O'
_chemical_formula_sum            'C5 H6 N4 O7'
_chemical_formula_weight         234.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.2036(5)
_cell_length_b                   7.0213(5)
_cell_length_c                   8.3381(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.364(2)
_cell_angle_gamma                90
_cell_volume                     408.55(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2939
_cell_measurement_theta_min      2.92
_cell_measurement_theta_max      27.40

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6479
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4088
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.919
_diffrn_reflns_theta_max         27.402
_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 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             1794
_reflns_number_gt                1652
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_max     0.939
_reflns_Friedel_fraction_full    0.936

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0538P)²+0.0176P] 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 678 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1794
_refine_ls_number_parameters     149
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 0.7660(2) 0.3616(3) 0.4480(2) 0.0188(5) Uani 1 1 d . . . . .
C2 C 0.7161(3) 0.4803(3) 0.5712(2) 0.0206(5) Uani 1 1 d . . . . .
C3 C 0.7338(3) 0.6763(3) 0.5321(2) 0.0196(4) Uani 1 1 d . . . . .
C4 C 0.7964(3) 0.6774(3) 0.3662(2) 0.0195(4) Uani 1 1 d . . . . .
C5 C 0.8169(3) 0.4819(3) 0.3272(3) 0.0210(4) Uani 1 1 d . . . . .
N1 N 0.7667(2) 0.1769(3) 0.4478(2) 0.0267(4) Uani 1 1 d . . . . .
H1A H 0.800064 0.115966 0.369931 0.032 Uiso 1 1 calc R U . . .
H1B H 0.733896 0.115316 0.525594 0.032 Uiso 1 1 calc R U . . .
N2 N 0.6546(3) 0.4133(3) 0.7033(2) 0.0239(4) Uani 1 1 d . . . . .
N3 N 0.8785(2) 0.4169(3) 0.1927(2) 0.0251(4) Uani 1 1 d . . . . .
O1 O 0.7110(2) 0.8226(2) 0.60477(18) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.8202(2) 0.8234(3) 0.29533(17) 0.0284(4) Uani 1 1 d . . . . .
O3 O 0.6435(3) 0.2373(2) 0.7258(2) 0.0338(4) Uani 1 1 d . . . . .
O4 O 0.6039(3) 0.5297(2) 0.79750(19) 0.0334(4) Uani 1 1 d . . . . .
O5 O 0.9260(3) 0.5340(3) 0.0991(2) 0.0373(4) Uani 1 1 d . . . . .
O6 O 0.8891(3) 0.2417(2) 0.1703(3) 0.0364(5) Uani 1 1 d . . . . .
N4 N 0.2767(2) 0.3964(3) 0.04832(19) 0.0279(4) Uani 1 1 d . . . . .
H4B H 0.260962 0.346036 0.142026 0.042 Uiso 1 1 calc R U . . .
H4A H 0.201283 0.336408 -0.037562 0.042 Uiso 1 1 calc R U . . .
H4C H 0.246017 0.519391 0.044399 0.042 Uiso 1 1 calc R U . . .
O7 O 0.4682(2) 0.3765(4) 0.0422(2) 0.0482(6) Uani 1 1 d . . . . .
H7 H 0.474(5) 0.436(6) -0.074(4) 0.072 Uiso 1 1 d . U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0197(9) 0.0166(12) 0.0201(9) -0.0004(7) 0.0050(7) -0.0005(7)
C2 0.0271(10) 0.0144(11) 0.0213(10) 0.0012(8) 0.0082(8) -0.0001(8)
C3 0.0237(9) 0.0154(10) 0.0199(9) 0.0029(8) 0.0059(7) 0.0000(8)
C4 0.0235(9) 0.0167(10) 0.0183(8) -0.0018(8) 0.0054(7) 0.0010(8)
C5 0.0263(10) 0.0168(11) 0.0212(9) -0.0005(8) 0.0082(7) 0.0001(8)
N1 0.0352(10) 0.0143(10) 0.0315(10) -0.0014(7) 0.0098(8) 0.0005(7)
N2 0.0287(8) 0.0220(10) 0.0222(8) 0.0023(8) 0.0086(6) -0.0020(8)
N3 0.0272(8) 0.0272(11) 0.0226(8) -0.0031(9) 0.0096(6) 0.0045(9)
O1 0.0418(8) 0.0158(7) 0.0254(6) -0.0016(7) 0.0141(6) -0.0001(7)
O2 0.0441(8) 0.0170(7) 0.0267(7) 0.0033(7) 0.0137(6) 0.0003(7)
O3 0.0502(10) 0.0187(9) 0.0355(9) 0.0066(7) 0.0163(8) -0.0019(7)
O4 0.0502(10) 0.0261(9) 0.0301(8) -0.0021(8) 0.0219(7) -0.0034(8)
O5 0.0483(10) 0.0365(11) 0.0348(9) 0.0051(8) 0.0251(8) 0.0057(8)
O6 0.0495(11) 0.0247(9) 0.0383(9) -0.0075(8) 0.0174(8) 0.0071(8)
N4 0.0339(8) 0.0273(10) 0.0253(8) -0.0004(7) 0.0123(6) 0.0021(8)
O7 0.0340(9) 0.0755(17) 0.0379(9) 0.0166(10) 0.0140(7) -0.0019(10)

_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 1.297(3) . ?
C1 C5 1.430(3) . ?
C1 C2 1.436(3) . ?
C2 N2 1.369(3) . ?
C2 C3 1.427(3) . ?
C3 O1 1.224(3) . ?
C3 C4 1.558(3) . ?
C4 O2 1.216(3) . ?
C4 C5 1.427(3) . ?
C5 N3 1.382(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 O4 1.249(3) . ?
N2 O3 1.256(3) . ?
N3 O5 1.239(3) . ?
N3 O6 1.250(3) . ?
N4 O7 1.401(2) . ?
N4 H4B 0.8900 . ?
N4 H4A 0.8900 . ?
N4 H4C 0.8900 . ?
O7 H7 1.06(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C5 126.05(18) . . ?
N1 C1 C2 125.65(19) . . ?
C5 C1 C2 108.30(19) . . ?
N2 C2 C3 125.5(2) . . ?
N2 C2 C1 124.39(19) . . ?
C3 C2 C1 110.11(18) . . ?
O1 C3 C2 131.73(18) . . ?
O1 C3 C4 122.63(19) . . ?
C2 C3 C4 105.64(17) . . ?
O2 C4 C5 131.68(18) . . ?
O2 C4 C3 122.85(18) . . ?
C5 C4 C3 105.47(17) . . ?
N3 C5 C4 125.1(2) . . ?
N3 C5 C1 124.47(19) . . ?
C4 C5 C1 110.43(18) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
O4 N2 O3 120.7(2) . . ?
O4 N2 C2 119.0(2) . . ?
O3 N2 C2 120.3(2) . . ?
O5 N3 O6 121.5(2) . . ?
O5 N3 C5 119.1(2) . . ?
O6 N3 C5 119.4(2) . . ?
O7 N4 H4B 109.5 . . ?
O7 N4 H4A 109.5 . . ?
H4B N4 H4A 109.5 . . ?
O7 N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
N4 O7 H7 104.6(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -2.7(3) . . . . ?
C5 C1 C2 N2 178.05(18) . . . . ?
N1 C1 C2 C3 179.29(17) . . . . ?
C5 C1 C2 C3 0.0(2) . . . . ?
N2 C2 C3 O1 4.3(3) . . . . ?
C1 C2 C3 O1 -177.7(2) . . . . ?
N2 C2 C3 C4 -176.61(18) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
O1 C3 C4 O2 -2.6(3) . . . . ?
C2 C3 C4 O2 178.20(18) . . . . ?
O1 C3 C4 C5 176.93(18) . . . . ?
C2 C3 C4 C5 -2.3(2) . . . . ?
O2 C4 C5 N3 2.2(4) . . . . ?
C3 C4 C5 N3 -177.22(19) . . . . ?
O2 C4 C5 C1 -178.2(2) . . . . ?
C3 C4 C5 C1 2.4(2) . . . . ?
N1 C1 C5 N3 -1.3(3) . . . . ?
C2 C1 C5 N3 178.01(18) . . . . ?
N1 C1 C5 C4 179.14(17) . . . . ?
C2 C1 C5 C4 -1.6(2) . . . . ?
C3 C2 N2 O4 2.1(3) . . . . ?
C1 C2 N2 O4 -175.68(17) . . . . ?
C3 C2 N2 O3 179.6(2) . . . . ?
C1 C2 N2 O3 1.9(3) . . . . ?
C4 C5 N3 O5 2.3(3) . . . . ?
C1 C5 N3 O5 -177.24(17) . . . . ?
C4 C5 N3 O6 -179.3(2) . . . . ?
C1 C5 N3 O6 1.1(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
O7 H7 O4 1.06(4) 1.72(4) 2.695(2) 150(3) 1_554 yes
O7 H7 N2 1.06(4) 2.53(3) 3.425(3) 142(3) 1_554 yes
N4 H4C O6 0.89 2.39 3.090(3) 135.4 2_655 yes
N4 H4C O3 0.89 2.43 3.012(3) 123.6 2_656 yes
N4 H4A O5 0.89 2.32 3.038(3) 137.7 2_645 yes
N4 H4A O2 0.89 2.12 2.823(2) 135.5 2_645 yes
N4 H4B O4 0.89 2.43 2.911(3) 114.5 2_646 yes
N4 H4B O1 0.89 2.08 2.918(2) 157.3 2_646 yes

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041

_shelx_res_file                  
;
TITL Wq190425_1_a.res in P2(1)
    Wq190425_1_a.res
    created by SHELXL-2018/3 at 16:36:09 on 25-Apr-2019
CELL 0.71073 7.2036 7.0213 8.3381 90.000 104.364 90.000
ZERR 2.00 0.0005 0.0005 0.0005 0.000 0.002 0.000
LATT -1
SYMM -x, y+1/2, -z
SFAC C  H  N  O
UNIT 10  12  8  14
L.S. 10
omit -3  -4   1
ACTA
BOND $H
FMAP 2
PLAN -2
HTAB O7 O4_$5
HTAB O7 N2_$5
EQIV $5 x, y, z-1
HTAB N4 O6_$4
EQIV $4 -x+1, y+1/2, -z
HTAB N4 O3_$3
EQIV $3 -x+1, y+1/2, -z+1
HTAB N4 O5_$2
HTAB N4 O2_$2
EQIV $2 -x+1, y-1/2, -z
HTAB N4 O4_$1
HTAB N4 O1_$1
EQIV $1 -x+1, y-1/2, -z+1
size 0.20 0.20 0.01
CONF
TEMP 23.000
WGHT    0.053800    0.017600
FVAR       1.68344
C1    1    0.766036    0.361570    0.447969    11.00000    0.01968    0.01661 =
         0.02014   -0.00042    0.00500   -0.00047
C2    1    0.716103    0.480296    0.571199    11.00000    0.02712    0.01444 =
         0.02135    0.00120    0.00822   -0.00007
C3    1    0.733839    0.676280    0.532133    11.00000    0.02369    0.01538 =
         0.01987    0.00295    0.00591    0.00005
C4    1    0.796395    0.677385    0.366205    11.00000    0.02351    0.01673 =
         0.01828   -0.00176    0.00540    0.00103
C5    1    0.816936    0.481913    0.327245    11.00000    0.02635    0.01678 =
         0.02123   -0.00050    0.00822    0.00009
N1    3    0.766745    0.176883    0.447814    11.00000    0.03524    0.01429 =
         0.03151   -0.00140    0.00980    0.00047
AFIX  93
H1A   2    0.800064    0.115966    0.369931    11.00000   -1.20000
H1B   2    0.733896    0.115316    0.525594    11.00000   -1.20000
AFIX   0
N2    3    0.654627    0.413294    0.703350    11.00000    0.02870    0.02199 =
         0.02223    0.00235    0.00855   -0.00197
N3    3    0.878452    0.416900    0.192749    11.00000    0.02720    0.02722 =
         0.02265   -0.00306    0.00965    0.00445
O1    4    0.710992    0.822607    0.604768    11.00000    0.04179    0.01580 =
         0.02543   -0.00156    0.01410   -0.00010
O2    4    0.820181    0.823359    0.295328    11.00000    0.04411    0.01703 =
         0.02666    0.00330    0.01368    0.00029
O3    4    0.643478    0.237278    0.725804    11.00000    0.05020    0.01866 =
         0.03549    0.00658    0.01625   -0.00187
O4    4    0.603883    0.529705    0.797501    11.00000    0.05019    0.02614 =
         0.03009   -0.00212    0.02190   -0.00337
O5    4    0.926002    0.533966    0.099127    11.00000    0.04834    0.03647 =
         0.03480    0.00514    0.02515    0.00571
O6    4    0.889132    0.241696    0.170323    11.00000    0.04951    0.02469 =
         0.03829   -0.00750    0.01735    0.00713
N4    3    0.276665    0.396389    0.048322    11.00000    0.03387    0.02728 =
         0.02528   -0.00036    0.01234    0.00215
AFIX 137
H4B   2    0.260962    0.346036    0.142026    11.00000   -1.50000
H4A   2    0.201283    0.336408   -0.037562    11.00000   -1.50000
H4C   2    0.246017    0.519391    0.044399    11.00000   -1.50000
AFIX   0
O7    4    0.468239    0.376450    0.042186    11.00000    0.03398    0.07555 =
         0.03788    0.01661    0.01395   -0.00186
H7    2    0.473562    0.436035   -0.073694    11.00000   -1.50000
HKLF 4 1 1 0 0 0 1 0 0 0 1




REM  Wq190425_1_a.res in P2(1)
REM wR2 = 0.0799, GooF = S = 1.081, Restrained GooF = 1.081 for all data
REM R1 = 0.0300 for 1652 Fo > 4sig(Fo) and 0.0342 for all 1794 data
REM 149 parameters refined using 1 restraints

END

WGHT      0.0505      0.0177

REM Highest difference peak  0.240,  deepest hole -0.191,  1-sigma level  0.041
Q1    1   0.7492  0.6666  0.4408  11.00000  0.05    0.24
Q2    1   0.6890  0.5728  0.5400  11.00000  0.05    0.21
;
_shelx_res_checksum              8793
####################################################################### 
# 
# 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_WQ190515_a
_database_code_depnum_ccdc_archive 'CCDC 1945174'
loop_
_audit_author_name
_audit_author_address
'Qian Wang'
;Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-02-01 deposited with the CCDC.	2022-02-21 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 N3 O6, H2 O, H4 N'
_chemical_formula_sum            'C5 H8 N4 O7'
_chemical_formula_weight         236.15

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'
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'
H H 0.0000 0.0000 '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                   14.319(2)
_cell_length_b                   9.3621(14)
_cell_length_c                   6.8195(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     914.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3616
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      26.34

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.161
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6898
_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_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8811
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.599
_diffrn_reflns_theta_max         27.567
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2059
_reflns_number_gt                1622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.808
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.974

_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 APEX2'
_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)+(0.0488P)²+0.0719P] 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_abs_structure_details 
;
 Flack x determined using 571 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2059
_refine_ls_number_parameters     145
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.69381(18) 0.3671(3) 0.4337(4) 0.0245(6) Uani 1 1 d . . . . .
C2 C 0.63057(17) 0.4810(3) 0.4789(4) 0.0242(6) Uani 1 1 d . . . . .
C3 C 0.68413(18) 0.6049(3) 0.5268(5) 0.0257(6) Uani 1 1 d . . . . .
C4 C 0.78169(18) 0.5744(3) 0.5101(4) 0.0233(6) Uani 1 1 d . . . . .
C5 C 0.78784(18) 0.4145(3) 0.4485(4) 0.0238(6) Uani 1 1 d . . . . .
N1 N 0.66619(16) 0.2289(2) 0.3889(4) 0.0309(6) Uani 1 1 d . . . . .
N2 N 0.64640(15) 0.7363(2) 0.5788(4) 0.0305(6) Uani 1 1 d . . . . .
N3 N 0.53946(15) 0.4719(3) 0.4726(4) 0.0353(6) Uani 1 1 d . . . . .
H3A H 0.505802 0.545533 0.498974 0.042 Uiso 1 1 calc R U . . .
H3B H 0.513222 0.392355 0.441999 0.042 Uiso 1 1 calc R U . . .
O1 O 0.72594(14) 0.1401(2) 0.3351(4) 0.0465(7) Uani 1 1 d . . . . .
O2 O 0.58223(14) 0.1952(2) 0.4048(4) 0.0448(6) Uani 1 1 d . . . . .
O3 O 0.55949(14) 0.7496(2) 0.5864(4) 0.0454(6) Uani 1 1 d . . . . .
O4 O 0.69892(14) 0.8372(2) 0.6187(4) 0.0453(6) Uani 1 1 d . . . . .
O5 O 0.85160(13) 0.64631(19) 0.5360(4) 0.0339(5) Uani 1 1 d . . . . .
O6 O 0.86285(13) 0.3541(2) 0.4257(3) 0.0318(5) Uani 1 1 d . . . . .
N4 N 0.92187(17) 0.0627(3) 0.3217(4) 0.0359(6) Uani 1 1 d . . . . .
H4A H 0.980752 0.064753 0.276941 0.043 Uiso 1 1 d R U . . .
H4B H 0.918452 0.018453 0.446041 0.043 Uiso 1 1 d R U . . .
H4C H 0.889452 0.151953 0.328141 0.043 Uiso 1 1 d R U . . .
H4D H 0.889752 0.008153 0.230941 0.043 Uiso 1 1 d R U . . .
O7 O 0.89410(14) 0.9138(2) 0.6772(4) 0.0385(6) Uani 1 1 d . . . . .
H7A H 0.872370 0.826241 0.651394 0.046 Uiso 1 1 d R U . . .
H7B H 0.856670 0.978341 0.729894 0.046 Uiso 1 1 d R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0213(13) 0.0229(13) 0.0294(15) -0.0014(13) -0.0017(12) -0.0015(12)
C2 0.0187(13) 0.0289(15) 0.0249(12) 0.0038(11) 0.0014(13) 0.0002(12)
C3 0.0206(13) 0.0253(13) 0.0314(15) -0.0021(12) 0.0033(12) 0.0041(12)
C4 0.0235(14) 0.0224(14) 0.0239(14) -0.0022(12) -0.0003(11) 0.0002(11)
C5 0.0212(13) 0.0240(14) 0.0260(15) 0.0021(12) -0.0004(12) 0.0007(11)
N1 0.0263(13) 0.0262(13) 0.0402(16) -0.0005(13) -0.0056(12) -0.0027(11)
N2 0.0260(13) 0.0284(12) 0.0371(15) -0.0019(12) 0.0012(12) 0.0032(11)
N3 0.0207(12) 0.0331(14) 0.0520(15) -0.0023(12) -0.0022(12) 0.0015(11)
O1 0.0318(13) 0.0277(11) 0.0800(18) -0.0172(13) -0.0013(13) 0.0016(9)
O2 0.0262(11) 0.0352(11) 0.0731(17) -0.0039(13) 0.0011(12) -0.0105(9)
O3 0.0230(11) 0.0393(12) 0.0738(17) -0.0067(13) 0.0054(13) 0.0094(9)
O4 0.0325(12) 0.0284(11) 0.0750(18) -0.0133(12) -0.0002(13) -0.0018(10)
O5 0.0200(10) 0.0281(10) 0.0536(13) -0.0098(10) 0.0014(10) -0.0030(8)
O6 0.0211(10) 0.0269(10) 0.0474(13) -0.0045(10) 0.0031(9) 0.0028(8)
N4 0.0301(13) 0.0317(13) 0.0459(16) -0.0031(13) 0.0019(12) 0.0010(11)
O7 0.0313(11) 0.0268(11) 0.0574(14) -0.0103(10) -0.0010(11) -0.0013(9)

_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 1.387(3) . ?
C1 C5 1.421(3) . ?
C1 C2 1.432(4) . ?
C2 N3 1.308(3) . ?
C2 C3 1.428(4) . ?
C3 N2 1.389(3) . ?
C3 C4 1.430(4) . ?
C4 O5 1.219(3) . ?
C4 C5 1.557(4) . ?
C5 O6 1.224(3) . ?
N1 O2 1.248(3) . ?
N1 O1 1.248(3) . ?
N2 O4 1.238(3) . ?
N2 O3 1.252(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4A 0.8968 . ?
N4 H4B 0.9454 . ?
N4 H4C 0.9567 . ?
N4 H4D 0.9249 . ?
O7 H7A 0.8940 . ?
O7 H7B 0.8842 . ?

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 C5 125.2(2) . . ?
N1 C1 C2 124.2(2) . . ?
C5 C1 C2 110.6(2) . . ?
N3 C2 C3 126.6(3) . . ?
N3 C2 C1 125.1(3) . . ?
C3 C2 C1 108.3(2) . . ?
N2 C3 C2 124.6(2) . . ?
N2 C3 C4 125.2(3) . . ?
C2 C3 C4 110.1(2) . . ?
O5 C4 C3 132.8(2) . . ?
O5 C4 C5 121.6(2) . . ?
C3 C4 C5 105.6(2) . . ?
O6 C5 C1 132.7(3) . . ?
O6 C5 C4 121.9(2) . . ?
C1 C5 C4 105.4(2) . . ?
O2 N1 O1 121.1(2) . . ?
O2 N1 C1 119.5(2) . . ?
O1 N1 C1 119.4(2) . . ?
O4 N2 O3 121.3(2) . . ?
O4 N2 C3 119.7(2) . . ?
O3 N2 C3 119.0(2) . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
H4A N4 H4B 111.3 . . ?
H4A N4 H4C 117.0 . . ?
H4B N4 H4C 108.4 . . ?
H4A N4 H4D 104.6 . . ?
H4B N4 H4D 109.4 . . ?
H4C N4 H4D 105.8 . . ?
H7A O7 H7B 119.7 . . ?

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 N3 -4.2(5) . . . . ?
C5 C1 C2 N3 177.9(3) . . . . ?
N1 C1 C2 C3 177.1(3) . . . . ?
C5 C1 C2 C3 -0.8(4) . . . . ?
N3 C2 C3 N2 1.3(5) . . . . ?
C1 C2 C3 N2 -179.9(3) . . . . ?
N3 C2 C3 C4 -177.6(3) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
N2 C3 C4 O5 1.0(5) . . . . ?
C2 C3 C4 O5 179.9(3) . . . . ?
N2 C3 C4 C5 -179.9(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
N1 C1 C5 O6 1.1(5) . . . . ?
C2 C1 C5 O6 179.0(3) . . . . ?
N1 C1 C5 C4 -177.6(3) . . . . ?
C2 C1 C5 C4 0.2(3) . . . . ?
O5 C4 C5 O6 0.8(4) . . . . ?
C3 C4 C5 O6 -178.5(3) . . . . ?
O5 C4 C5 C1 179.7(3) . . . . ?
C3 C4 C5 C1 0.4(2) . . . . ?
C5 C1 N1 O2 170.8(3) . . . . ?
C2 C1 N1 O2 -6.8(5) . . . . ?
C5 C1 N1 O1 -8.5(5) . . . . ?
C2 C1 N1 O1 173.9(3) . . . . ?
C2 C3 N2 O4 179.7(3) . . . . ?
C4 C3 N2 O4 -1.5(5) . . . . ?
C2 C3 N2 O3 0.5(5) . . . . ?
C4 C3 N2 O3 179.3(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
N3 H3A O3 0.86 2.14 2.728(3) 124.8 . yes
N3 H3A O6 0.86 2.31 3.025(3) 141.1 4_465 yes
N3 H3B O2 0.86 2.11 2.702(3) 125.6 . yes
N3 H3B O5 0.86 2.43 2.941(3) 118.8 4_465 yes
N4 H4A O7 0.90 1.93 2.822(3) 175.1 2_764 yes
N4 H4B O7 0.95 1.89 2.826(4) 170.4 1_545 yes
N4 H4C O1 0.96 2.34 2.899(3) 116.4 . yes
N4 H4C O6 0.96 2.04 2.943(3) 156.2 . yes
N4 H4D O4 0.92 2.18 3.061(3) 158.3 3_644 yes
O7 H7A O5 0.89 1.88 2.751(3) 163.2 . yes
O7 H7B N1 0.88 2.61 3.396(3) 149.4 3_665 yes
O7 H7B O1 0.88 2.05 2.933(3) 175.2 3_665 yes
O7 H7B O2 0.88 2.51 3.076(3) 122.3 3_665 yes

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.046

_shelx_res_file                  
;
TITL WQ190515_a.res in Pca2(1)
    WQ190515_a.res
    created by SHELXL-2018/3 at 15:25:45 on 31-Jan-2022
CELL 0.71073 14.3190 9.3621 6.8195 90.000 90.000 90.000
ZERR 4.00 0.0021 0.0014 0.0009 0.000 0.000 0.000
LATT -1
SYMM -x, -y, z+1/2
SYMM -x+1/2, y, z+1/2
SYMM x+1/2, -y, z
SFAC C  N  O  H
UNIT 20  16  28  32
omit 0   1   0
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN -10
HTAB N3 O3
EQIV $1 x-1/2, -y+1, z
HTAB N3 O6_$1
HTAB N3 O2
HTAB N3 O5_$1
EQIV $2 -x+2, -y+1, z-1/2
HTAB N4 O7_$2
EQIV $3 x, y-1, z
HTAB N4 O7_$3
HTAB N4 O1
HTAB N4 O6
EQIV $4 -x+3/2, y-1, z-1/2
HTAB N4 O4_$4
HTAB O7 O5
EQIV $5 -x+3/2, y+1, z+1/2
HTAB O7 N1_$5
HTAB O7 O1_$5
HTAB O7 O2_$5
CONF
size 0.20 0.01 0.01
TEMP 23.000
WGHT    0.048800    0.071900
FVAR       0.83240
C1    1    0.693808    0.367126    0.433745    11.00000    0.02132    0.02288 =
         0.02936   -0.00143   -0.00167   -0.00152
C2    1    0.630571    0.481008    0.478866    11.00000    0.01867    0.02894 =
         0.02493    0.00377    0.00141    0.00019
C3    1    0.684127    0.604873    0.526843    11.00000    0.02056    0.02526 =
         0.03138   -0.00205    0.00334    0.00411
C4    1    0.781687    0.574401    0.510063    11.00000    0.02350    0.02242 =
         0.02388   -0.00221   -0.00029    0.00018
C5    1    0.787838    0.414493    0.448488    11.00000    0.02123    0.02400 =
         0.02605    0.00210   -0.00040    0.00071
N1    2    0.666192    0.228946    0.388868    11.00000    0.02631    0.02623 =
         0.04018   -0.00054   -0.00558   -0.00269
N2    2    0.646400    0.736265    0.578799    11.00000    0.02599    0.02841 =
         0.03706   -0.00195    0.00118    0.00319
N3    2    0.539462    0.471929    0.472560    11.00000    0.02068    0.03311 =
         0.05199   -0.00229   -0.00224    0.00151
AFIX  93
H3A   4    0.505802    0.545533    0.498974    11.00000   -1.20000
H3B   4    0.513222    0.392355    0.441999    11.00000   -1.20000
AFIX   0

O1    3    0.725936    0.140125    0.335109    11.00000    0.03179    0.02768 =
         0.07998   -0.01716   -0.00127    0.00160
O2    3    0.582230    0.195155    0.404757    11.00000    0.02619    0.03524 =
         0.07308   -0.00394    0.00106   -0.01050
O3    3    0.559489    0.749600    0.586354    11.00000    0.02302    0.03926 =
         0.07382   -0.00668    0.00544    0.00945
O4    3    0.698918    0.837158    0.618709    11.00000    0.03252    0.02843 =
         0.07497   -0.01327   -0.00015   -0.00180
O5    3    0.851598    0.646314    0.536036    11.00000    0.02000    0.02809 =
         0.05361   -0.00981    0.00136   -0.00300
O6    3    0.862848    0.354106    0.425661    11.00000    0.02114    0.02686 =
         0.04744   -0.00451    0.00310    0.00278
N4    2    0.921872    0.062731    0.321660    11.00000    0.03013    0.03167 =
         0.04588   -0.00310    0.00187    0.00100
AFIX   3
H4A   4    0.980752    0.064753    0.276941    11.00000   -1.20000
H4B   4    0.918452    0.018453    0.446041    11.00000   -1.20000
H4C   4    0.889452    0.151953    0.328141    11.00000   -1.20000
H4D   4    0.889752    0.008153    0.230941    11.00000   -1.20000
AFIX   0
O7    3    0.894103    0.913754    0.677250    11.00000    0.03131    0.02679 =
         0.05735   -0.01029   -0.00097   -0.00125
AFIX   3
H7A   4    0.872370    0.826241    0.651394    11.00000   -1.20000
H7B   4    0.856670    0.978341    0.729894    11.00000   -1.20000

AFIX   0
HKLF 4 1 1 0 0 0 1 0 0 0 1




REM  WQ190515_a.res in Pca2(1)
REM wR2 = 0.090667, GooF = S = 1.04280, Restrained GooF = 1.04253 for all data
REM R1 = 0.038243 for 1622 Fo > 4sig(Fo) and 0.062110 for all 2059 data
REM 145 parameters refined using 1 restraints

END

WGHT      0.0478      0.0811

REM Highest difference peak  0.162,  deepest hole -0.209,  1-sigma level  0.046
Q1    1   0.5056  0.5994  0.7082  11.00000  0.05    0.16
Q2    1   0.5487  0.7645  0.7973  11.00000  0.05    0.16
Q3    1   0.6818  0.8075  0.8630  11.00000  0.05    0.15
Q4    1   0.7195  0.6183  0.4673  11.00000  0.05    0.14
Q5    1   0.6641  0.4028  0.4903  11.00000  0.05    0.14
Q6    1   0.7836  0.4868  0.4970  11.00000  0.05    0.14
Q7    1   0.5801  0.3329  0.6416  11.00000  0.05    0.14
Q8    1   0.7869  0.7966  0.8306  11.00000  0.05    0.14
Q9    1   0.4306  0.5238  0.5181  11.00000  0.05    0.14
Q10   1   0.7314  0.3673  0.5038  11.00000  0.05    0.14
;
_shelx_res_checksum              99757
