# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2008004'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Stadnicka'
;Jagiellonian University Cracow
Poland
;
_audit_update_record             
;
2020-06-04 deposited with the CCDC.	2024-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'2-ammonio-3-hydroxypropanoate - 5-(hydroxyimino)pyrimidine-2,4,6(1H,3H,5H)-trione (1:1) dihydrate'
_chemical_name_common            
;
L-serinium violurate dihydrate <1/1/2>
;
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C4 H3 N3 O4, C3 H7 N O3, 2(H2 O)
;
_chemical_formula_sum            'C7 H14 N4 O9'
_chemical_formula_weight         298.22

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   6.2773(2)
_cell_length_b                   12.2828(3)
_cell_length_c                   15.5226(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1196.84(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    18258
_cell_measurement_theta_min      3.0930
_cell_measurement_theta_max      26.8960

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.58441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_reflns_number            58263
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.501
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2733
_reflns_number_gt                2480
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_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       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_solution    'SIR-92 (ALTOMARE et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0350P)²+0.3158P] 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 976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2733
_refine_ls_number_parameters     223
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0805
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_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
N1A N 0.2180(4) 0.08031(15) 0.39206(11) 0.0300(4) Uani 1 1 d D . . . .
H1A H 0.218(4) 0.0116(11) 0.4022(16) 0.036 Uiso 1 1 d D U . . .
C2A C 0.1961(4) 0.11499(17) 0.30832(13) 0.0269(4) Uani 1 1 d . . . . .
O2A O 0.1949(3) 0.05104(12) 0.24804(10) 0.0357(4) Uani 1 1 d . . . . .
N3A N 0.1741(3) 0.22426(14) 0.29575(12) 0.0305(4) Uani 1 1 d D . . . .
H3A H 0.154(5) 0.246(2) 0.2442(10) 0.037 Uiso 1 1 d D U . . .
C4A C 0.1770(4) 0.30426(18) 0.35765(15) 0.0308(5) Uani 1 1 d . . . . .
O4A O 0.1537(3) 0.39875(13) 0.33838(12) 0.0439(5) Uani 1 1 d . . . . .
C5A C 0.2072(4) 0.26407(18) 0.44726(14) 0.0306(5) Uani 1 1 d . . . . .
C6A C 0.2188(4) 0.1449(2) 0.46396(14) 0.0310(5) Uani 1 1 d . . . . .
O6A O 0.2307(3) 0.10459(15) 0.53529(10) 0.0435(5) Uani 1 1 d . . . . .
N5A N 0.2232(8) 0.3129(4) 0.5222(3) 0.0314(13) Uani 0.584(6) 1 d . . P A 1
O5A O 0.2144(6) 0.4220(3) 0.51307(19) 0.0354(9) Uani 0.584(6) 1 d . . P A 1
H5A H 0.2215 0.4509 0.5606 0.042 Uiso 0.584(6) 1 calc R U P A 1
N5A1 N 0.2109(10) 0.3535(6) 0.4944(4) 0.0265(14) Uani 0.416(6) 1 d . . P A 2
O5A1 O 0.2355(8) 0.3294(3) 0.5785(3) 0.0358(13) Uani 0.416(6) 1 d . . P A 2
H5A1 H 0.1903 0.2678 0.5878 0.043 Uiso 0.416(6) 1 calc R U P A 2
C1B C -0.1058(4) 0.28607(17) 0.08691(13) 0.0278(4) Uani 1 1 d . . . . .
O1B O 0.0659(3) 0.29679(13) 0.12686(11) 0.0347(4) Uani 1 1 d . . . . .
O2B O -0.2244(3) 0.36118(13) 0.06122(11) 0.0409(4) Uani 1 1 d . . . . .
C2B C -0.1845(4) 0.17042(16) 0.06816(13) 0.0273(4) Uani 1 1 d . . . . .
H2B H -0.2338 0.1671 0.0083 0.033 Uiso 1 1 calc R U . . .
N1B N -0.0068(3) 0.09102(15) 0.07951(12) 0.0294(4) Uani 1 1 d . . . . .
H1B1 H 0.1005 0.1089 0.0448 0.044 Uiso 1 1 calc R U . . .
H1B2 H 0.0376 0.0924 0.1340 0.044 Uiso 1 1 calc R U . . .
H1B3 H -0.0525 0.0244 0.0666 0.044 Uiso 1 1 calc R U . . .
C3B C -0.3690(4) 0.1406(2) 0.12734(16) 0.0350(5) Uani 1 1 d . . . . .
H3B1 H -0.4826 0.1935 0.1207 0.042 Uiso 1 1 calc R U . . .
H3B2 H -0.4245 0.0697 0.1113 0.042 Uiso 1 1 calc R U . . .
O3B O -0.3019(3) 0.13827(14) 0.21416(11) 0.0406(4) Uani 1 1 d D . . . .
H7B H -0.323(5) 0.1991(14) 0.2338(18) 0.049 Uiso 1 1 d D U . . .
O1W O -0.2881(4) -0.01185(14) 0.34547(11) 0.0444(5) Uani 1 1 d D . . . .
H11W H -0.194(4) -0.059(2) 0.350(2) 0.053 Uiso 1 1 d D U . . .
H12W H -0.289(6) 0.012(2) 0.2961(8) 0.053 Uiso 1 1 d D U . . .
O2W O -0.3482(4) 0.33272(16) 0.28881(13) 0.0506(5) Uani 1 1 d D . . . .
H21W H -0.327(6) 0.3919(12) 0.2659(18) 0.061 Uiso 1 1 d D U . . .
H22W H -0.309(6) 0.335(3) 0.3393(9) 0.061 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
N1A C6A 1.369(3) . ?
N1A C2A 1.375(3) . ?
N1A H1A 0.859(13) . ?
C2A O2A 1.222(2) . ?
C2A N3A 1.363(3) . ?
N3A C4A 1.375(3) . ?
N3A H3A 0.855(13) . ?
C4A O4A 1.207(3) . ?
C4A C5A 1.488(3) . ?
C5A N5A 1.313(5) . ?
C5A N5A1 1.321(7) . ?
C5A C6A 1.489(3) . ?
C6A O6A 1.215(3) . ?
N5A O5A 1.348(5) . ?
O5A H5A 0.8200 . ?
N5A1 O5A1 1.347(7) . ?
O5A1 H5A1 0.8200 . ?
C1B O1B 1.250(3) . ?
C1B O2B 1.251(3) . ?
C1B C2B 1.532(3) . ?
C2B N1B 1.492(3) . ?
C2B C3B 1.523(3) . ?
C2B H2B 0.9800 . ?
N1B H1B1 0.8900 . ?
N1B H1B2 0.8900 . ?
N1B H1B3 0.8900 . ?
C3B O3B 1.412(3) . ?
C3B H3B1 0.9700 . ?
C3B H3B2 0.9700 . ?
O3B H7B 0.818(13) . ?
O1W H11W 0.827(11) . ?
O1W H12W 0.820(6) . ?
O2W H21W 0.8200(14) . ?
O2W H22W 0.822(10) . ?

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
C6A N1A C2A 126.27(19) . . ?
C6A N1A H1A 114.9(17) . . ?
C2A N1A H1A 118.5(17) . . ?
O2A C2A N3A 121.51(19) . . ?
O2A C2A N1A 121.71(19) . . ?
N3A C2A N1A 116.78(18) . . ?
C2A N3A C4A 127.04(19) . . ?
C2A N3A H3A 117.6(19) . . ?
C4A N3A H3A 115.4(19) . . ?
O4A C4A N3A 120.8(2) . . ?
O4A C4A C5A 124.5(2) . . ?
N3A C4A C5A 114.70(19) . . ?
N5A C5A C4A 133.3(3) . . ?
N5A1 C5A C4A 104.2(4) . . ?
N5A C5A C6A 106.9(3) . . ?
N5A1 C5A C6A 136.1(4) . . ?
C4A C5A C6A 119.70(18) . . ?
O6A C6A N1A 120.5(2) . . ?
O6A C6A C5A 124.2(2) . . ?
N1A C6A C5A 115.31(19) . . ?
C5A N5A O5A 110.9(4) . . ?
N5A O5A H5A 109.5 . . ?
C5A N5A1 O5A1 110.8(6) . . ?
N5A1 O5A1 H5A1 109.5 . . ?
O1B C1B O2B 126.4(2) . . ?
O1B C1B C2B 118.03(19) . . ?
O2B C1B C2B 115.5(2) . . ?
N1B C2B C3B 109.89(17) . . ?
N1B C2B C1B 110.04(18) . . ?
C3B C2B C1B 110.71(18) . . ?
N1B C2B H2B 108.7 . . ?
C3B C2B H2B 108.7 . . ?
C1B C2B H2B 108.7 . . ?
C2B N1B H1B1 109.5 . . ?
C2B N1B H1B2 109.5 . . ?
H1B1 N1B H1B2 109.5 . . ?
C2B N1B H1B3 109.5 . . ?
H1B1 N1B H1B3 109.5 . . ?
H1B2 N1B H1B3 109.5 . . ?
O3B C3B C2B 110.69(19) . . ?
O3B C3B H3B1 109.5 . . ?
C2B C3B H3B1 109.5 . . ?
O3B C3B H3B2 109.5 . . ?
C2B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 108.1 . . ?
C3B O3B H7B 107(2) . . ?
H11W O1W H12W 110(3) . . ?
H21W O2W H22W 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
C6A N1A C2A O2A -179.2(2) . . . . ?
C6A N1A C2A N3A 0.3(4) . . . . ?
O2A C2A N3A C4A -178.7(2) . . . . ?
N1A C2A N3A C4A 1.9(4) . . . . ?
C2A N3A C4A O4A -179.3(2) . . . . ?
C2A N3A C4A C5A -0.2(3) . . . . ?
O4A C4A C5A N5A -2.6(5) . . . . ?
N3A C4A C5A N5A 178.3(4) . . . . ?
O4A C4A C5A N5A1 -2.6(4) . . . . ?
N3A C4A C5A N5A1 178.2(3) . . . . ?
O4A C4A C5A C6A 175.7(2) . . . . ?
N3A C4A C5A C6A -3.5(3) . . . . ?
C2A N1A C6A O6A 177.0(2) . . . . ?
C2A N1A C6A C5A -3.7(4) . . . . ?
N5A C5A C6A O6A 3.1(4) . . . . ?
N5A1 C5A C6A O6A 2.1(6) . . . . ?
C4A C5A C6A O6A -175.5(2) . . . . ?
N5A C5A C6A N1A -176.1(3) . . . . ?
N5A1 C5A C6A N1A -177.2(4) . . . . ?
C4A C5A C6A N1A 5.2(3) . . . . ?
C4A C5A N5A O5A -1.7(6) . . . . ?
C6A C5A N5A O5A 179.9(3) . . . . ?
C4A C5A N5A1 O5A1 179.4(4) . . . . ?
C6A C5A N5A1 O5A1 1.5(8) . . . . ?
O1B C1B C2B N1B -16.5(3) . . . . ?
O2B C1B C2B N1B 164.57(19) . . . . ?
O1B C1B C2B C3B 105.1(2) . . . . ?
O2B C1B C2B C3B -73.8(2) . . . . ?
N1B C2B C3B O3B 57.8(2) . . . . ?
C1B C2B C3B O3B -64.0(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
N1A H1A O2B 0.859(13) 1.933(14) 2.788(2) 173(2) 4_545
N3A H3A O1B 0.855(13) 2.001(14) 2.851(2) 172(3) .
O5A H5A O1W 0.82 1.64 2.458(4) 174.6 3_556
O5A1 H5A1 O6A 0.82 2.18 2.841(4) 137.9 .
O5A1 H5A1 O2W 0.82 2.29 2.912(5) 132.8 3_556
C2B H2B O1B 0.98 2.49 3.432(3) 162.2 3_455
N1B H1B1 O2B 0.89 2.01 2.874(3) 162.4 3
N1B H1B2 O2A 0.89 2.09 2.948(2) 161.4 .
N1B H1B3 O4A 0.89 2.23 2.838(2) 125.4 4_545
N1B H1B3 O6A 0.89 2.61 3.041(3) 110.5 2_554
N1B H1B3 O5A 0.89 2.04 2.842(4) 150.0 4_545
N1B H1B3 N5A1 0.89 2.51 3.386(8) 169.2 4_545
O3B H7B O2W 0.818(13) 1.857(14) 2.670(3) 173(3) .
O1W H11W O1B 0.827(11) 1.982(16) 2.767(2) 158(3) 4_545
O1W H12W O4A 0.820(6) 2.65(3) 3.172(3) 123(3) 4_545
O1W H12W O3B 0.820(6) 2.009(16) 2.750(2) 150(3) .
O2W H21W O2A 0.8200(14) 2.135(14) 2.906(3) 157(3) 4
O2W H22W O6A 0.822(10) 2.100(16) 2.880(3) 159(3) 3_456
O2W H22W O5A1 0.822(10) 2.40(3) 2.912(5) 121(3) 3_456

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.044



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2008006'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Stadnicka'
;Jagiellonian University Cracow
Poland
;
_audit_update_record             
;
2020-06-04 deposited with the CCDC.	2024-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
2-azaniumyl-3-(2,3-dihydro-1H-inden-2-yl)propanoate-5-
(hydroxyimino)-1,3-diazinane-2,4,6-trione (1/1)
;
_chemical_name_common            
;
tryptophanium violurate co-crystal
;
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C11 H12 N2 O2, C4 H3 N3 O4
;
_chemical_formula_sum            'C15 H15 N5 O6'
_chemical_formula_weight         361.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   5.57110(10)
_cell_length_b                   7.65960(10)
_cell_length_c                   35.1063(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1498.07(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7936
_cell_measurement_theta_min      2.5220
_cell_measurement_theta_max      75.9200

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.081
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75427
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14377
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.517
_diffrn_reflns_theta_max         69.949
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2841
_reflns_number_gt                2754
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.995

_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       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0414P)²+0.3078P] 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 1064 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(6)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2841
_refine_ls_number_parameters     269
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_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
N1A N 0.1401(4) 0.2622(3) 0.54965(5) 0.0344(4) Uani 1 1 d D . . . .
H1A H 0.180(6) 0.223(4) 0.5275(6) 0.068(10) Uiso 1 1 d D . . . .
C2A C -0.0718(4) 0.3524(3) 0.55003(6) 0.0316(5) Uani 1 1 d . . . . .
O2A O -0.1939(3) 0.3761(2) 0.52198(4) 0.0452(4) Uani 1 1 d . . . . .
N3A N -0.1396(4) 0.4180(3) 0.58491(5) 0.0349(4) Uani 1 1 d D . . . .
H3A H -0.269(3) 0.478(3) 0.5851(8) 0.042 Uiso 1 1 d D U . . .
C4A C -0.0220(5) 0.4056(3) 0.61892(6) 0.0364(5) Uani 1 1 d . . . . .
O4A O -0.1065(4) 0.4735(3) 0.64730(5) 0.0507(5) Uani 1 1 d . . . . .
C5A C 0.2036(5) 0.3047(3) 0.61728(7) 0.0387(6) Uani 1 1 d . . . . .
N5A N 0.2907(6) 0.3122(4) 0.65307(17) 0.0279(10) Uani 0.667(8) 1 d . . P A 1
O5A O 0.4956(7) 0.2259(3) 0.65497(10) 0.0336(10) Uani 0.667(8) 1 d . . P A 1
H5A H 0.5450 0.2269 0.6770 0.040 Uiso 0.667(8) 1 calc R U P A 1
N5A1 N 0.3836(16) 0.2419(8) 0.6387(2) 0.0224(18) Uani 0.333(8) 1 d . . P A 2
O5A1 O 0.3372(10) 0.3054(6) 0.6745(2) 0.0297(16) Uani 0.333(8) 1 d . . P A 2
H5A1 H 0.4411 0.2713 0.6893 0.036 Uiso 0.333(8) 1 calc R U P A 2
C6A C 0.2852(4) 0.2284(3) 0.58067(7) 0.0371(5) Uani 1 1 d . . . . .
O6A O 0.4672(3) 0.1443(3) 0.57680(7) 0.0556(5) Uani 1 1 d . . . . .
C1B C 1.0351(4) 0.3500(3) 0.94107(6) 0.0334(5) Uani 1 1 d . . . . .
H1B H 1.1650 0.3923 0.9549 0.040 Uiso 1 1 calc R U . . .
C2B C 0.8536(5) 0.2581(3) 0.95840(6) 0.0387(5) Uani 1 1 d . . . . .
H2B H 0.8609 0.2382 0.9845 0.046 Uiso 1 1 calc R U . . .
C3B C 0.6581(5) 0.1937(3) 0.93772(7) 0.0374(5) Uani 1 1 d . . . . .
H3B H 0.5381 0.1320 0.9503 0.045 Uiso 1 1 calc R U . . .
C4B C 0.6405(4) 0.2205(3) 0.89877(6) 0.0299(5) Uani 1 1 d . . . . .
H4B H 0.5105 0.1769 0.8851 0.036 Uiso 1 1 calc R U . . .
C5B C 0.8218(4) 0.3141(3) 0.88035(5) 0.0241(4) Uani 1 1 d . . . . .
C6B C 1.0170(4) 0.3774(3) 0.90199(6) 0.0268(4) Uani 1 1 d . . . . .
N7B N 1.1644(3) 0.4689(3) 0.87789(5) 0.0318(4) Uani 1 1 d D . . . .
H7B H 1.295(3) 0.524(3) 0.8837(7) 0.038 Uiso 1 1 d D U . . .
C8B C 1.0687(4) 0.4637(3) 0.84206(6) 0.0300(5) Uani 1 1 d . . . . .
H8B H 1.147(5) 0.532(3) 0.8215(7) 0.036 Uiso 1 1 d . U . . .
C9B C 0.8605(4) 0.3704(3) 0.84185(5) 0.0252(4) Uani 1 1 d . . . . .
C10B C 0.6980(4) 0.3605(3) 0.80780(6) 0.0288(5) Uani 1 1 d . . . . .
H10A H 0.7682 0.4318 0.7879 0.035 Uiso 1 1 calc R U . . .
H10B H 0.5466 0.4143 0.8148 0.035 Uiso 1 1 calc R U . . .
C11B C 0.6417(4) 0.1813(3) 0.79058(5) 0.0234(4) Uani 1 1 d . . . . .
H11B H 0.5351 0.1168 0.8078 0.028 Uiso 1 1 calc R U . . .
N11B N 0.8650(3) 0.0774(2) 0.78381(5) 0.0248(4) Uani 1 1 d . . . . .
H11A H 0.8264 -0.0256 0.7738 0.037 Uiso 1 1 calc R U . . .
H11C H 0.9602 0.1349 0.7678 0.037 Uiso 1 1 calc R U . . .
H11D H 0.9413 0.0612 0.8058 0.037 Uiso 1 1 calc R U . . .
C12B C 0.5109(4) 0.2180(3) 0.75304(6) 0.0251(4) Uani 1 1 d . . . . .
O12B O 0.6397(3) 0.2181(2) 0.72367(4) 0.0389(4) Uani 1 1 d . . . . .
O13B O 0.2940(3) 0.2565(2) 0.75479(5) 0.0352(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C2A 1.367(3) . ?
N1A C6A 1.381(3) . ?
N1A H1A 0.863(13) . ?
C2A O2A 1.211(3) . ?
C2A N3A 1.377(3) . ?
N3A C4A 1.365(3) . ?
N3A H3A 0.856(13) . ?
C4A O4A 1.219(3) . ?
C4A C5A 1.477(4) . ?
C5A N5A1 1.342(10) . ?
C5A N5A 1.348(6) . ?
C5A C6A 1.483(4) . ?
N5A O5A 1.320(6) . ?
O5A H5A 0.8200 . ?
N5A1 O5A1 1.373(10) . ?
O5A1 H5A1 0.8200 . ?
C6A O6A 1.209(3) . ?
C1B C2B 1.375(4) . ?
C1B C6B 1.392(3) . ?
C1B H1B 0.9300 . ?
C2B C3B 1.399(4) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.386(3) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.397(3) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.412(3) . ?
C5B C9B 1.435(3) . ?
C6B N7B 1.371(3) . ?
N7B C8B 1.367(3) . ?
N7B H7B 0.864(13) . ?
C8B C9B 1.362(3) . ?
C8B H8B 0.99(3) . ?
C9B C10B 1.502(3) . ?
C10B C11B 1.532(3) . ?
C10B H10A 0.9700 . ?
C10B H10B 0.9700 . ?
C11B N11B 1.496(3) . ?
C11B C12B 1.532(3) . ?
C11B H11B 0.9800 . ?
N11B H11A 0.8900 . ?
N11B H11C 0.8900 . ?
N11B H11D 0.8900 . ?
C12B O13B 1.245(3) . ?
C12B O12B 1.256(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
C2A N1A C6A 126.3(2) . . ?
C2A N1A H1A 114(2) . . ?
C6A N1A H1A 119(2) . . ?
O2A C2A N1A 123.6(2) . . ?
O2A C2A N3A 121.0(2) . . ?
N1A C2A N3A 115.46(19) . . ?
C4A N3A C2A 128.4(2) . . ?
C4A N3A H3A 115.8(19) . . ?
C2A N3A H3A 115.7(19) . . ?
O4A C4A N3A 120.0(2) . . ?
O4A C4A C5A 125.7(2) . . ?
N3A C4A C5A 114.3(2) . . ?
N5A1 C5A C4A 143.3(3) . . ?
N5A C5A C4A 104.4(2) . . ?
N5A1 C5A C6A 96.6(3) . . ?
N5A C5A C6A 135.6(3) . . ?
C4A C5A C6A 120.05(19) . . ?
O5A N5A C5A 109.7(5) . . ?
N5A O5A H5A 109.5 . . ?
C5A N5A1 O5A1 104.2(7) . . ?
N5A1 O5A1 H5A1 109.5 . . ?
O6A C6A N1A 120.2(3) . . ?
O6A C6A C5A 124.4(2) . . ?
N1A C6A C5A 115.5(2) . . ?
C2B C1B C6B 117.4(2) . . ?
C2B C1B H1B 121.3 . . ?
C6B C1B H1B 121.3 . . ?
C1B C2B C3B 121.6(2) . . ?
C1B C2B H2B 119.2 . . ?
C3B C2B H2B 119.2 . . ?
C4B C3B C2B 121.0(2) . . ?
C4B C3B H3B 119.5 . . ?
C2B C3B H3B 119.5 . . ?
C3B C4B C5B 118.8(2) . . ?
C3B C4B H4B 120.6 . . ?
C5B C4B H4B 120.6 . . ?
C4B C5B C6B 118.94(19) . . ?
C4B C5B C9B 134.3(2) . . ?
C6B C5B C9B 106.72(19) . . ?
N7B C6B C1B 129.9(2) . . ?
N7B C6B C5B 107.74(18) . . ?
C1B C6B C5B 122.3(2) . . ?
C8B N7B C6B 108.61(18) . . ?
C8B N7B H7B 124.1(18) . . ?
C6B N7B H7B 127.3(18) . . ?
C9B C8B N7B 110.65(19) . . ?
C9B C8B H8B 130.3(15) . . ?
N7B C8B H8B 118.8(15) . . ?
C8B C9B C5B 106.27(18) . . ?
C8B C9B C10B 123.00(18) . . ?
C5B C9B C10B 130.08(19) . . ?
C9B C10B C11B 118.88(16) . . ?
C9B C10B H10A 107.6 . . ?
C11B C10B H10A 107.6 . . ?
C9B C10B H10B 107.6 . . ?
C11B C10B H10B 107.6 . . ?
H10A C10B H10B 107.0 . . ?
N11B C11B C10B 111.66(17) . . ?
N11B C11B C12B 110.87(16) . . ?
C10B C11B C12B 105.82(16) . . ?
N11B C11B H11B 109.5 . . ?
C10B C11B H11B 109.5 . . ?
C12B C11B H11B 109.5 . . ?
C11B N11B H11A 109.5 . . ?
C11B N11B H11C 109.5 . . ?
H11A N11B H11C 109.5 . . ?
C11B N11B H11D 109.5 . . ?
H11A N11B H11D 109.5 . . ?
H11C N11B H11D 109.5 . . ?
O13B C12B O12B 126.5(2) . . ?
O13B C12B C11B 117.55(19) . . ?
O12B C12B C11B 115.77(18) . . ?

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
C6A N1A C2A O2A -178.9(2) . . . . ?
C6A N1A C2A N3A 1.7(3) . . . . ?
O2A C2A N3A C4A -178.9(2) . . . . ?
N1A C2A N3A C4A 0.6(3) . . . . ?
C2A N3A C4A O4A 179.2(2) . . . . ?
C2A N3A C4A C5A -1.6(3) . . . . ?
O4A C4A C5A N5A1 3.1(6) . . . . ?
N3A C4A C5A N5A1 -176.1(5) . . . . ?
O4A C4A C5A N5A -2.0(3) . . . . ?
N3A C4A C5A N5A 178.8(2) . . . . ?
O4A C4A C5A C6A 179.8(2) . . . . ?
N3A C4A C5A C6A 0.5(3) . . . . ?
C4A C5A N5A O5A -179.7(2) . . . . ?
C6A C5A N5A O5A -1.9(4) . . . . ?
C4A C5A N5A1 O5A1 -4.2(7) . . . . ?
C6A C5A N5A1 O5A1 178.7(4) . . . . ?
C2A N1A C6A O6A 178.8(2) . . . . ?
C2A N1A C6A C5A -2.5(3) . . . . ?
N5A1 C5A C6A O6A -2.1(4) . . . . ?
N5A C5A C6A O6A 2.4(4) . . . . ?
C4A C5A C6A O6A 179.9(2) . . . . ?
N5A1 C5A C6A N1A 179.2(3) . . . . ?
N5A C5A C6A N1A -176.3(3) . . . . ?
C4A C5A C6A N1A 1.3(3) . . . . ?
C6B C1B C2B C3B 0.2(4) . . . . ?
C1B C2B C3B C4B 0.0(4) . . . . ?
C2B C3B C4B C5B -0.3(3) . . . . ?
C3B C4B C5B C6B 0.3(3) . . . . ?
C3B C4B C5B C9B -177.9(2) . . . . ?
C2B C1B C6B N7B 177.2(2) . . . . ?
C2B C1B C6B C5B -0.2(3) . . . . ?
C4B C5B C6B N7B -177.97(19) . . . . ?
C9B C5B C6B N7B 0.7(2) . . . . ?
C4B C5B C6B C1B -0.1(3) . . . . ?
C9B C5B C6B C1B 178.6(2) . . . . ?
C1B C6B N7B C8B -178.1(2) . . . . ?
C5B C6B N7B C8B -0.4(2) . . . . ?
C6B N7B C8B C9B 0.0(3) . . . . ?
N7B C8B C9B C5B 0.4(2) . . . . ?
N7B C8B C9B C10B 172.06(18) . . . . ?
C4B C5B C9B C8B 177.7(2) . . . . ?
C6B C5B C9B C8B -0.7(2) . . . . ?
C4B C5B C9B C10B 6.9(4) . . . . ?
C6B C5B C9B C10B -171.49(19) . . . . ?
C8B C9B C10B C11B 121.5(2) . . . . ?
C5B C9B C10B C11B -69.1(3) . . . . ?
C9B C10B C11B N11B -49.7(2) . . . . ?
C9B C10B C11B C12B -170.43(18) . . . . ?
N11B C11B C12B O13B 159.50(18) . . . . ?
C10B C11B C12B O13B -79.3(2) . . . . ?
N11B C11B C12B O12B -25.4(3) . . . . ?
C10B C11B C12B O12B 95.8(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
N1A H1A O2A 0.863(13) 2.022(14) 2.881(3) 174(3) 4_556
O5A H5A O12B 0.82 1.72 2.543(4) 176.7 .
O5A1 H5A1 O12B 0.82 1.69 2.504(8) 172.9 .
O5A1 H5A1 O13B 0.82 2.44 2.854(8) 111.9 .
N7B H7B O5A 0.864(13) 2.37(2) 2.966(3) 127(2) 3_756
N7B H7B N5A1 0.864(13) 2.57(2) 3.324(9) 146(2) 3_756
N7B H7B O6A 0.864(13) 2.128(16) 2.923(3) 153(2) 3_756
C8B H8B O5A 0.99(3) 2.62(3) 3.153(4) 113.8(17) 3_756
C8B H8B O12B 0.99(3) 2.44(3) 3.429(3) 174(2) 3_756
C10B H10B O5A 0.97 2.62 3.272(3) 124.5 3_656
C11B H11B O5A1 0.98 2.57 3.131(5) 116.8 3_646
N11B H11D O4A 0.89 2.00 2.880(2) 168.4 3_646
N11B H11A O13B 0.89 2.06 2.944(2) 171.5 3_646
N11B H11C O13B 0.89 2.13 2.938(2) 150.7 1_655

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2008008'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Stadnicka'
;Jagiellonian University Cracow
Poland
;
_audit_update_record             
;
2020-06-04 deposited with the CCDC.	2024-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
2-azaniumyl-3-(1H-imidazol-3-ium-5-yl)propanoate 
[(2,4,6-trioxo-1,3-diazinan-5-ylidene)amino]oxidanide dihydrate
;
_chemical_name_common            
;
L-histidinum violurate dihydrate <1/1/2>
;
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C4 H2 N3 O4, C6 H10 N3 O2, H2 O
;
_chemical_formula_sum            'C10 H14 N6 O7'
_chemical_formula_weight         330.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   5.09210(10)
_cell_length_b                   36.4707(4)
_cell_length_c                   7.54320(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.4630(10)
_cell_angle_gamma                90
_cell_volume                     1320.82(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16015
_cell_measurement_theta_min      2.4240
_cell_measurement_theta_max      77.1530

_exptl_crystal_description       plate
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.234
_shelx_estimated_absorpt_T_min   0.856
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.26a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            34683
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.423
_diffrn_reflns_theta_max         69.000
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4856
_reflns_number_gt                4707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.964
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    0.993

_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       'CrysAlisPro 1.171.40.26a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.26a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.26a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0541P)²+0.3213P] 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 2100 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(7)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4856
_refine_ls_number_parameters     470
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0932
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.089
_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
N1A N 0.5937(6) 0.71482(9) 0.6834(4) 0.0320(7) Uani 1 1 d D . . . .
H1A H 0.426(4) 0.7185(12) 0.610(5) 0.038 Uiso 1 1 d D U . . .
C2A C 0.7041(7) 0.74279(10) 0.8046(5) 0.0285(7) Uani 1 1 d . . . . .
O2A O 0.5778(5) 0.77099(7) 0.8065(4) 0.0384(6) Uani 1 1 d . . . . .
N3A N 0.9712(6) 0.73737(8) 0.9264(4) 0.0302(6) Uani 1 1 d D . . . .
H3A H 1.036(8) 0.7553(8) 1.002(5) 0.036 Uiso 1 1 d D U . . .
C4A C 1.1312(7) 0.70662(10) 0.9326(5) 0.0272(7) Uani 1 1 d . . . . .
O4A O 1.3718(5) 0.70584(7) 1.0470(4) 0.0349(6) Uani 1 1 d . . . . .
C5A C 1.0021(7) 0.67734(9) 0.8053(5) 0.0273(7) Uani 1 1 d . . . . .
N5A N 1.1659(6) 0.64791(8) 0.8220(4) 0.0310(6) Uani 1 1 d . . . . .
O5A O 1.0759(6) 0.61992(7) 0.7237(4) 0.0441(7) Uani 1 1 d . . . . .
C6A C 0.7186(7) 0.68117(10) 0.6745(5) 0.0318(8) Uani 1 1 d . . . . .
O6A O 0.5883(6) 0.65833(9) 0.5640(5) 0.0584(9) Uani 1 1 d . . . . .
N1B N 0.9845(6) 0.28437(8) 0.4509(4) 0.0307(6) Uani 1 1 d D . . . .
H1B H 0.819(4) 0.2812(12) 0.374(5) 0.037 Uiso 1 1 d D U . . .
C2B C 1.0912(7) 0.25719(9) 0.5779(5) 0.0277(7) Uani 1 1 d . . . . .
O2B O 0.9619(5) 0.22882(7) 0.5807(4) 0.0397(6) Uani 1 1 d . . . . .
N3B N 1.3553(6) 0.26294(8) 0.7006(4) 0.0307(6) Uani 1 1 d D . . . .
H3B H 1.420(9) 0.2460(9) 0.783(5) 0.037 Uiso 1 1 d D U . . .
C4B C 1.5129(6) 0.29365(9) 0.7055(5) 0.0267(7) Uani 1 1 d . . . . .
O4B O 1.7512(5) 0.29509(7) 0.8252(4) 0.0359(6) Uani 1 1 d . . . . .
C5B C 1.3907(7) 0.32200(9) 0.5700(5) 0.0260(7) Uani 1 1 d . . . . .
N5B N 1.5571(6) 0.35130(8) 0.5871(4) 0.0343(7) Uani 1 1 d . . . . .
O5B O 1.4725(6) 0.37840(8) 0.4780(4) 0.0457(7) Uani 1 1 d . . . . .
C6B C 1.1126(7) 0.31717(10) 0.4337(5) 0.0277(7) Uani 1 1 d . . . . .
O6B O 0.9901(5) 0.33842(7) 0.3096(4) 0.0420(7) Uani 1 1 d . . . . .
N1C N 0.5050(6) 0.38475(9) 0.0279(4) 0.0324(6) Uani 1 1 d D . . . .
H1C H 0.670(5) 0.3900(12) 0.100(5) 0.039 Uiso 1 1 d D U . . .
C2C C 0.3702(8) 0.35373(10) 0.0290(5) 0.0344(8) Uani 1 1 d . . . . .
H2C H 0.4371 0.3339 0.1089 0.041 Uiso 1 1 calc R U . . .
N3C N 0.1235(6) 0.35594(8) -0.1037(5) 0.0339(7) Uani 1 1 d D . . . .
H3C H -0.001(7) 0.3390(9) -0.134(6) 0.041 Uiso 1 1 d D U . . .
C4C C 0.0984(7) 0.38887(10) -0.1922(5) 0.0325(7) Uani 1 1 d . . . . .
H4C H -0.0552 0.3971 -0.2905 0.039 Uiso 1 1 calc R U . . .
C5C C 0.3388(7) 0.40750(9) -0.1104(5) 0.0286(7) Uani 1 1 d . . . . .
C6C C 0.4222(8) 0.44496(10) -0.1510(5) 0.0336(8) Uani 1 1 d . . . . .
H6C1 H 0.2810 0.4542 -0.2632 0.040 Uiso 1 1 calc R U . . .
H6C2 H 0.5950 0.4431 -0.1781 0.040 Uiso 1 1 calc R U . . .
C7C C 0.4621(6) 0.47282(9) 0.0083(5) 0.0265(7) Uani 1 1 d . . . . .
H7C H 0.623(8) 0.4669(11) 0.127(6) 0.032 Uiso 1 1 d . U . . .
N7C N 0.2198(6) 0.47366(8) 0.0754(4) 0.0320(6) Uani 1 1 d . . . . .
H7C1 H 0.2501 0.4901 0.1675 0.048 Uiso 1 1 calc R U . . .
H7C2 H 0.0676 0.4798 -0.0192 0.048 Uiso 1 1 calc R U . . .
H7C3 H 0.1963 0.4516 0.1183 0.048 Uiso 1 1 calc R U . . .
C8C C 0.5107(7) 0.51129(9) -0.0578(5) 0.0298(7) Uani 1 1 d . . . . .
O82C O 0.3286(6) 0.53453(8) -0.0789(5) 0.0533(8) Uani 1 1 d . . . . .
O81C O 0.7380(5) 0.51556(7) -0.0874(4) 0.0350(6) Uani 1 1 d . . . . .
N1D N -0.1023(7) 0.58812(10) 0.0837(4) 0.0403(7) Uani 1 1 d D . . . .
H1D H -0.090(10) 0.5653(6) 0.054(7) 0.048 Uiso 1 1 d D U . . .
C2D C -0.3208(9) 0.60886(11) 0.0153(6) 0.0419(9) Uani 1 1 d . . . . .
H2D H -0.4846 0.6025 -0.0797 0.050 Uiso 1 1 calc R U . . .
N3D N -0.2705(7) 0.63955(9) 0.1015(5) 0.0376(7) Uani 1 1 d D . . . .
H3D H -0.372(8) 0.6589(8) 0.089(7) 0.045 Uiso 1 1 d D U . . .
C4D C 0.0030(9) 0.63938(11) 0.2407(6) 0.0418(9) Uani 1 1 d . . . . .
H4D H 0.0906 0.6581 0.3230 0.050 Uiso 1 1 calc R U . . .
C5D C 0.1029(7) 0.60579(9) 0.2242(5) 0.0285(7) Uani 1 1 d . . . . .
C6D C 0.3795(7) 0.58899(10) 0.3228(5) 0.0311(7) Uani 1 1 d . . . . .
H6D1 H 0.5178 0.6083 0.3591 0.037 Uiso 1 1 calc R U . . .
H6D2 H 0.4279 0.5731 0.2353 0.037 Uiso 1 1 calc R U . . .
C7D C 0.3952(7) 0.56660(10) 0.4989(5) 0.0275(7) Uani 1 1 d . . . . .
H7D H 0.322(8) 0.5797(11) 0.580(6) 0.033 Uiso 1 1 d . U . . .
N7D N 0.6967(6) 0.56088(8) 0.6065(4) 0.0310(6) Uani 1 1 d . . . . .
H7D1 H 0.7795 0.5825 0.6396 0.046 Uiso 1 1 calc R U . . .
H7D2 H 0.7139 0.5477 0.7091 0.046 Uiso 1 1 calc R U . . .
H7D3 H 0.7766 0.5490 0.5349 0.046 Uiso 1 1 calc R U . . .
C8D C 0.2513(7) 0.52977(10) 0.4414(5) 0.0290(7) Uani 1 1 d . . . . .
O81D O 0.3990(5) 0.50328(7) 0.4318(4) 0.0439(7) Uani 1 1 d . . . . .
O82D O -0.0078(5) 0.52939(8) 0.3970(4) 0.0419(6) Uani 1 1 d . . . . .
O1W O 1.0115(5) 0.41458(8) 0.2419(4) 0.0374(6) Uani 1 1 d D . . . .
H11W H 0.957(10) 0.4268(13) 0.324(7) 0.045 Uiso 1 1 d D U . . .
H12W H 1.106(9) 0.3981(13) 0.292(7) 0.045 Uiso 1 1 d D U . . .
O21W O 0.858(2) 0.4590(4) 0.4824(10) 0.048(3) Uani 0.61(4) 1 d D . P . .
O22W O 0.767(4) 0.4439(6) 0.4817(16) 0.052(4) Uani 0.39(4) 1 d D . P . .
H211 H 0.92(2) 0.4794(13) 0.466(14) 0.063 Uiso 0.61(4) 1 d D U P . .
H221 H 0.66(3) 0.425(4) 0.50(2) 0.063 Uiso 0.39(4) 1 d . U P . .
H222 H 0.702(6) 0.4646(8) 0.480(9) 0.063 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
N1A C2A 1.360(5) . ?
N1A C6A 1.394(5) . ?
N1A H1A 0.859(15) . ?
C2A O2A 1.216(4) . ?
C2A N3A 1.379(4) . ?
N3A C4A 1.378(5) . ?
N3A H3A 0.856(15) . ?
C4A O4A 1.242(4) . ?
C4A C5A 1.440(5) . ?
C5A N5A 1.339(4) . ?
C5A C6A 1.459(5) . ?
N5A O5A 1.255(4) . ?
C6A O6A 1.208(5) . ?
N1B C2B 1.359(5) . ?
N1B C6B 1.389(5) . ?
N1B H1B 0.857(9) . ?
C2B O2B 1.230(4) . ?
C2B N3B 1.371(4) . ?
N3B C4B 1.371(5) . ?
N3B H3B 0.860(15) . ?
C4B O4B 1.249(4) . ?
C4B C5B 1.441(5) . ?
C5B N5B 1.343(4) . ?
C5B C6B 1.457(4) . ?
N5B O5B 1.266(4) . ?
C6B O6B 1.215(4) . ?
N1C C2C 1.325(5) . ?
N1C C5C 1.380(4) . ?
N1C H1C 0.857(15) . ?
C2C N3C 1.322(5) . ?
C2C H2C 0.9300 . ?
N3C C4C 1.359(5) . ?
N3C H3C 0.861(15) . ?
C4C C5C 1.356(5) . ?
C4C H4C 0.9300 . ?
C5C C6C 1.493(5) . ?
C6C C7C 1.535(5) . ?
C6C H6C1 0.9700 . ?
C6C H6C2 0.9700 . ?
C7C N7C 1.482(4) . ?
C7C C8C 1.536(5) . ?
C7C H7C 1.01(4) . ?
N7C H7C1 0.8900 . ?
N7C H7C2 0.8900 . ?
N7C H7C3 0.8900 . ?
C8C O82C 1.227(4) . ?
C8C O81C 1.259(4) . ?
N1D C2D 1.301(6) . ?
N1D C5D 1.376(5) . ?
N1D H1D 0.870(15) . ?
C2D N3D 1.277(6) . ?
C2D H2D 0.9300 . ?
N3D C4D 1.438(5) . ?
N3D H3D 0.859(15) . ?
C4D C5D 1.348(5) . ?
C4D H4D 0.9300 . ?
C5D C6D 1.488(5) . ?
C6D C7D 1.539(5) . ?
C6D H6D1 0.9700 . ?
C6D H6D2 0.9700 . ?
C7D N7D 1.493(4) . ?
C7D C8D 1.522(5) . ?
C7D H7D 0.94(4) . ?
N7D H7D1 0.8900 . ?
N7D H7D2 0.8900 . ?
N7D H7D3 0.8900 . ?
C8D O81D 1.242(4) . ?
C8D O82D 1.248(4) . ?
O1W H11W 0.88(5) . ?
O1W H12W 0.78(4) . ?
O21W O22W 0.720(14) . ?
O21W H211 0.825(16) . ?
O21W H222 0.817(15) . ?
O22W H221 0.91(16) . ?
O22W H222 0.823(15) . ?

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
C2A N1A C6A 126.8(3) . . ?
C2A N1A H1A 114(3) . . ?
C6A N1A H1A 119(3) . . ?
O2A C2A N1A 122.7(3) . . ?
O2A C2A N3A 121.4(3) . . ?
N1A C2A N3A 115.8(3) . . ?
C2A N3A C4A 125.5(3) . . ?
C2A N3A H3A 114(3) . . ?
C4A N3A H3A 120(3) . . ?
O4A C4A N3A 118.5(3) . . ?
O4A C4A C5A 124.9(3) . . ?
N3A C4A C5A 116.6(3) . . ?
N5A C5A C4A 113.6(3) . . ?
N5A C5A C6A 125.8(3) . . ?
C4A C5A C6A 120.6(3) . . ?
O5A N5A C5A 120.2(3) . . ?
O6A C6A N1A 119.1(3) . . ?
O6A C6A C5A 126.3(3) . . ?
N1A C6A C5A 114.6(3) . . ?
C2B N1B C6B 127.2(3) . . ?
C2B N1B H1B 117(3) . . ?
C6B N1B H1B 116(3) . . ?
O2B C2B N1B 122.3(3) . . ?
O2B C2B N3B 121.8(3) . . ?
N1B C2B N3B 115.8(3) . . ?
C4B N3B C2B 125.2(3) . . ?
C4B N3B H3B 119(3) . . ?
C2B N3B H3B 115(3) . . ?
O4B C4B N3B 118.2(3) . . ?
O4B C4B C5B 124.6(3) . . ?
N3B C4B C5B 117.2(3) . . ?
N5B C5B C4B 113.2(3) . . ?
N5B C5B C6B 126.7(3) . . ?
C4B C5B C6B 120.1(3) . . ?
O5B N5B C5B 119.4(3) . . ?
O6B C6B N1B 119.0(3) . . ?
O6B C6B C5B 126.5(3) . . ?
N1B C6B C5B 114.5(3) . . ?
C2C N1C C5C 109.2(3) . . ?
C2C N1C H1C 126(3) . . ?
C5C N1C H1C 125(3) . . ?
N3C C2C N1C 107.9(3) . . ?
N3C C2C H2C 126.1 . . ?
N1C C2C H2C 126.1 . . ?
C2C N3C C4C 109.6(3) . . ?
C2C N3C H3C 126(3) . . ?
C4C N3C H3C 124(3) . . ?
C5C C4C N3C 107.2(3) . . ?
C5C C4C H4C 126.4 . . ?
N3C C4C H4C 126.4 . . ?
C4C C5C N1C 106.1(3) . . ?
C4C C5C C6C 129.8(3) . . ?
N1C C5C C6C 124.1(3) . . ?
C5C C6C C7C 114.7(3) . . ?
C5C C6C H6C1 108.6 . . ?
C7C C6C H6C1 108.6 . . ?
C5C C6C H6C2 108.6 . . ?
C7C C6C H6C2 108.6 . . ?
H6C1 C6C H6C2 107.6 . . ?
N7C C7C C6C 111.9(3) . . ?
N7C C7C C8C 109.5(3) . . ?
C6C C7C C8C 110.1(3) . . ?
N7C C7C H7C 103(2) . . ?
C6C C7C H7C 114(2) . . ?
C8C C7C H7C 108(2) . . ?
C7C N7C H7C1 109.5 . . ?
C7C N7C H7C2 109.5 . . ?
H7C1 N7C H7C2 109.5 . . ?
C7C N7C H7C3 109.5 . . ?
H7C1 N7C H7C3 109.5 . . ?
H7C2 N7C H7C3 109.5 . . ?
O82C C8C O81C 126.2(3) . . ?
O82C C8C C7C 118.5(3) . . ?
O81C C8C C7C 115.3(3) . . ?
C2D N1D C5D 111.3(4) . . ?
C2D N1D H1D 125(3) . . ?
C5D N1D H1D 123(3) . . ?
N3D C2D N1D 107.9(4) . . ?
N3D C2D H2D 126.1 . . ?
N1D C2D H2D 126.1 . . ?
C2D N3D C4D 110.4(3) . . ?
C2D N3D H3D 131(3) . . ?
C4D N3D H3D 119(3) . . ?
C5D C4D N3D 103.9(3) . . ?
C5D C4D H4D 128.1 . . ?
N3D C4D H4D 128.1 . . ?
C4D C5D N1D 106.5(3) . . ?
C4D C5D C6D 130.7(3) . . ?
N1D C5D C6D 122.8(3) . . ?
C5D C6D C7D 114.7(3) . . ?
C5D C6D H6D1 108.6 . . ?
C7D C6D H6D1 108.6 . . ?
C5D C6D H6D2 108.6 . . ?
C7D C6D H6D2 108.6 . . ?
H6D1 C6D H6D2 107.6 . . ?
N7D C7D C8D 110.0(3) . . ?
N7D C7D C6D 107.0(3) . . ?
C8D C7D C6D 109.9(3) . . ?
N7D C7D H7D 106(3) . . ?
C8D C7D H7D 112(3) . . ?
C6D C7D H7D 112(2) . . ?
C7D N7D H7D1 109.5 . . ?
C7D N7D H7D2 109.5 . . ?
H7D1 N7D H7D2 109.5 . . ?
C7D N7D H7D3 109.5 . . ?
H7D1 N7D H7D3 109.5 . . ?
H7D2 N7D H7D3 109.5 . . ?
O81D C8D O82D 125.6(3) . . ?
O81D C8D C7D 117.4(3) . . ?
O82D C8D C7D 116.9(3) . . ?
H11W O1W H12W 110(5) . . ?
O22W O21W H211 162(7) . . ?
O22W O21W H222 64.4(16) . . ?
H211 O21W H222 99(7) . . ?
O21W O22W H221 169(10) . . ?
O21W O22W H222 63.5(17) . . ?
H221 O22W H222 115(9) . . ?

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
C6A N1A C2A O2A -177.9(4) . . . . ?
C6A N1A C2A N3A 2.3(5) . . . . ?
O2A C2A N3A C4A -179.0(4) . . . . ?
N1A C2A N3A C4A 0.7(5) . . . . ?
C2A N3A C4A O4A 178.3(3) . . . . ?
C2A N3A C4A C5A -2.5(5) . . . . ?
O4A C4A C5A N5A 0.9(5) . . . . ?
N3A C4A C5A N5A -178.3(3) . . . . ?
O4A C4A C5A C6A -179.3(3) . . . . ?
N3A C4A C5A C6A 1.6(5) . . . . ?
C4A C5A N5A O5A 177.6(3) . . . . ?
C6A C5A N5A O5A -2.2(6) . . . . ?
C2A N1A C6A O6A 176.6(4) . . . . ?
C2A N1A C6A C5A -3.0(5) . . . . ?
N5A C5A C6A O6A 1.1(6) . . . . ?
C4A C5A C6A O6A -178.7(4) . . . . ?
N5A C5A C6A N1A -179.2(3) . . . . ?
C4A C5A C6A N1A 0.9(5) . . . . ?
C6B N1B C2B O2B -179.2(4) . . . . ?
C6B N1B C2B N3B -0.6(5) . . . . ?
O2B C2B N3B C4B 179.6(3) . . . . ?
N1B C2B N3B C4B 1.0(5) . . . . ?
C2B N3B C4B O4B -179.9(3) . . . . ?
C2B N3B C4B C5B -0.3(5) . . . . ?
O4B C4B C5B N5B -1.6(5) . . . . ?
N3B C4B C5B N5B 178.9(3) . . . . ?
O4B C4B C5B C6B 178.7(3) . . . . ?
N3B C4B C5B C6B -0.9(5) . . . . ?
C4B C5B N5B O5B -179.0(3) . . . . ?
C6B C5B N5B O5B 0.7(6) . . . . ?
C2B N1B C6B O6B 178.7(4) . . . . ?
C2B N1B C6B C5B -0.5(5) . . . . ?
N5B C5B C6B O6B 2.4(6) . . . . ?
C4B C5B C6B O6B -177.9(4) . . . . ?
N5B C5B C6B N1B -178.5(3) . . . . ?
C4B C5B C6B N1B 1.2(5) . . . . ?
C5C N1C C2C N3C -0.1(4) . . . . ?
N1C C2C N3C C4C 0.1(4) . . . . ?
C2C N3C C4C C5C 0.0(4) . . . . ?
N3C C4C C5C N1C 0.0(4) . . . . ?
N3C C4C C5C C6C -179.4(4) . . . . ?
C2C N1C C5C C4C 0.1(4) . . . . ?
C2C N1C C5C C6C 179.5(3) . . . . ?
C4C C5C C6C C7C 114.1(4) . . . . ?
N1C C5C C6C C7C -65.2(4) . . . . ?
C5C C6C C7C N7C -50.8(4) . . . . ?
C5C C6C C7C C8C -172.8(3) . . . . ?
N7C C7C C8C O82C -12.6(5) . . . . ?
C6C C7C C8C O82C 110.9(4) . . . . ?
N7C C7C C8C O81C 168.2(3) . . . . ?
C6C C7C C8C O81C -68.3(4) . . . . ?
C5D N1D C2D N3D 0.7(5) . . . . ?
N1D C2D N3D C4D -0.6(5) . . . . ?
C2D N3D C4D C5D 0.3(4) . . . . ?
N3D C4D C5D N1D 0.1(4) . . . . ?
N3D C4D C5D C6D 177.1(3) . . . . ?
C2D N1D C5D C4D -0.4(4) . . . . ?
C2D N1D C5D C6D -177.8(3) . . . . ?
C4D C5D C6D C7D 93.5(5) . . . . ?
N1D C5D C6D C7D -89.8(4) . . . . ?
C5D C6D C7D N7D -164.7(3) . . . . ?
C5D C6D C7D C8D 75.9(4) . . . . ?
N7D C7D C8D O81D -23.1(4) . . . . ?
C6D C7D C8D O81D 94.4(4) . . . . ?
N7D C7D C8D O82D 161.1(3) . . . . ?
C6D C7D C8D O82D -81.4(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
N1A H1A O2B 0.859(15) 2.054(16) 2.912(4) 175(4) 2_656
N3A H3A O4B 0.856(15) 2.011(17) 2.859(4) 171(4) 2_857
N1B H1B O2A 0.857(9) 2.059(10) 2.916(4) 177(4) 2_646
N1C H1C O6B 0.857(15) 2.64(4) 3.158(4) 120(3) .
N1C H1C O1W 0.857(15) 1.932(19) 2.769(4) 165(4) .
C2C H2C O2A 0.93 2.39 3.240(4) 151.9 2_646
N3C H3C O4B 0.861(15) 1.997(17) 2.851(4) 171(4) 1_354
N3C H3C N5B 0.861(15) 2.55(4) 3.050(4) 118(4) 1_354
C4C H4C N5B 0.93 2.52 3.031(5) 115.3 1_354
C4C H4C O5B 0.93 2.55 3.348(4) 144.1 1_354
C4C H4C O22W 0.93 2.38 3.188(14) 145.6 1_454
C6C H6C1 O21W 0.97 2.37 3.296(8) 160.5 1_454
C7C H7C O21W 1.01(4) 2.56(4) 3.508(7) 155(3) .
C7C H7C O22W 1.01(4) 2.67(4) 3.547(12) 145(3) .
N7C H7C3 O1W 0.89 2.04 2.870(4) 154.5 1_455
N7C H7C1 O81D 0.89 1.94 2.755(4) 150.9 .
N7C H7C2 O81C 0.89 2.05 2.803(4) 141.6 1_455
N1D H1D O81C 0.870(15) 2.14(3) 2.938(4) 153(4) 1_455
C2D H2D N5A 0.93 2.36 2.906(5) 117.0 1_354
C2D H2D O5A 0.93 2.32 3.152(5) 148.1 1_354
C2D H2D O82C 0.93 2.65 3.193(5) 117.5 1_455
N3D H3D O4A 0.859(15) 2.113(16) 2.972(4) 178(5) 1_354
C4D H4D O6A 0.93 2.58 3.235(5) 127.8 .
C6D H6D1 O6A 0.97 2.34 3.090(5) 133.7 .
C6D H6D2 O82C 0.97 2.66 3.559(5) 155.2 .
C7D H7D O5A 0.94(4) 2.41(4) 3.337(4) 167(3) 1_455
N7D H7D1 O5A 0.89 1.98 2.830(4) 160.3 .
N7D H7D2 O81C 0.89 1.90 2.790(4) 174.3 1_556
N7D H7D3 O82D 0.89 1.89 2.768(4) 170.8 1_655
O1W H11W O21W 0.88(5) 1.86(5) 2.733(8) 171(5) .
O1W H11W O22W 0.88(5) 1.88(5) 2.734(13) 165(5) .
O1W H12W O5B 0.78(4) 2.06(5) 2.763(4) 150(5) .
O1W H12W O6B 0.78(4) 2.27(5) 2.833(4) 129(4) .
O21W H211 O81D 0.825(16) 2.70(7) 3.323(18) 133(8) 1_655
O21W H211 O82D 0.825(16) 1.97(3) 2.787(18) 171(10) 1_655
O22W H221 O5B 0.91(16) 1.94(16) 2.81(3) 159(14) 1_455
O21W H222 O81D 0.817(15) 2.031(17) 2.762(7) 149(3) .
O22W H222 O81D 0.823(15) 2.031(17) 2.805(11) 156(3) .

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.039



####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2008007'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Stadnicka'
;Jagiellonian University Cracow
Poland
;
_audit_update_record             
;
2020-06-04 deposited with the CCDC.	2024-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
2,6-bis(azaniumyl)hexanoate [(2,4,6-trioxo-1,3-diazinan-5-ylidene)
amino]oxidanide-water (1/1/2)
;
_chemical_name_common            
;
l-lysinium violurate dihydrate <1/1/2>
;
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C4 H2 N3 O4, C5 H15 N2 O2, H2 O
;
_chemical_formula_sum            'C10 H19 N5 O7'
_chemical_formula_weight         321.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   5.03472(3)
_cell_length_b                   10.34570(6)
_cell_length_c                   14.35285(9)
_cell_angle_alpha                108.7195(6)
_cell_angle_beta                 93.0287(5)
_cell_angle_gamma                97.0239(5)
_cell_volume                     699.365(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    41320
_cell_measurement_theta_min      3.2500
_cell_measurement_theta_max      77.2290

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.117
_shelx_estimated_absorpt_T_min   0.791
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            55829
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.267
_diffrn_reflns_theta_max         71.963
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             5297
_reflns_number_gt                5190
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_max     0.928
_reflns_Friedel_fraction_full    0.956

_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (Macrae, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_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)+(0.0543P)²+0.1341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0025(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2449 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5297
_refine_ls_number_parameters     476
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0813
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.068
_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
N1A N -0.1080(4) 0.9107(2) 0.76764(14) 0.0147(4) Uani 1 1 d D . . . .
H1A H -0.101(7) 0.838(2) 0.785(2) 0.018 Uiso 1 1 d D U . . .
C2A C -0.2858(5) 0.9996(2) 0.80607(17) 0.0141(5) Uani 1 1 d . . . . .
O2A O -0.4177(4) 0.98960(17) 0.87331(12) 0.0186(4) Uani 1 1 d . . . . .
N3A N -0.3066(4) 1.1010(2) 0.76462(14) 0.0141(4) Uani 1 1 d D . . . .
H3A H -0.420(5) 1.157(3) 0.788(2) 0.017 Uiso 1 1 d D U . . .
C4A C -0.1688(5) 1.1184(2) 0.68794(16) 0.0119(4) Uani 1 1 d . . . . .
O4A O -0.2106(3) 1.21272(16) 0.65626(11) 0.0142(3) Uani 1 1 d . . . . .
C5A C 0.0177(5) 1.0216(2) 0.64929(16) 0.0131(5) Uani 1 1 d . . . . .
N5A N 0.1429(5) 1.0380(2) 0.57333(16) 0.0198(5) Uani 1 1 d D . . . .
O5A O 0.3055(4) 0.95803(19) 0.53400(14) 0.0160(4) Uani 0.8714 1 d . . P . .
O5A' O 0.214(3) 1.1374(10) 0.5461(9) 0.019(3) Uiso 0.1286 1 d D . P . .
C6A C 0.0467(5) 0.9128(2) 0.69118(17) 0.0133(5) Uani 1 1 d . . . . .
O6A O 0.1953(4) 0.82444(17) 0.66407(12) 0.0172(4) Uani 1 1 d . . . . .
N1B N 0.2104(4) 0.5869(2) 0.71859(14) 0.0139(4) Uani 1 1 d D . . . .
H1B H 0.206(6) 0.656(2) 0.697(2) 0.017 Uiso 1 1 d D U . . .
C2B C 0.3909(5) 0.4991(2) 0.68064(16) 0.0132(5) Uani 1 1 d . . . . .
O2B O 0.5216(4) 0.50863(18) 0.61329(13) 0.0182(4) Uani 1 1 d . . . . .
N3B N 0.4140(4) 0.3986(2) 0.72302(14) 0.0133(4) Uani 1 1 d D . . . .
H3B H 0.524(5) 0.340(3) 0.700(2) 0.016 Uiso 1 1 d D U . . .
C4B C 0.2769(5) 0.3815(2) 0.80000(16) 0.0118(4) Uani 1 1 d . . . . .
O4B O 0.3185(3) 0.28772(16) 0.83211(12) 0.0143(3) Uani 1 1 d . . . . .
C5B C 0.0877(5) 0.4773(2) 0.83752(16) 0.0120(5) Uani 1 1 d . . . . .
N5B N -0.0325(4) 0.46130(19) 0.91501(14) 0.0131(4) Uani 1 1 d . . . . .
O5B O -0.2051(3) 0.53972(17) 0.95122(12) 0.0154(3) Uani 1 1 d . . . . .
C6B C 0.0536(5) 0.5841(2) 0.79394(16) 0.0122(4) Uani 1 1 d . . . . .
O6B O -0.0998(4) 0.67019(17) 0.81895(12) 0.0160(4) Uani 1 1 d . . . . .
N1C N 0.6716(4) 0.0969(2) 0.44538(14) 0.0143(4) Uani 1 1 d D . . . .
H1C1 H 0.518(4) 0.052(3) 0.456(2) 0.017 Uiso 1 1 d D U . . .
H1C2 H 0.749(6) 0.043(3) 0.3958(17) 0.017 Uiso 1 1 d D U . . .
H1C3 H 0.798(5) 0.112(3) 0.4963(16) 0.017 Uiso 1 1 d D U . . .
C2C C 0.6044(6) 0.2183(3) 0.4207(2) 0.0164(6) Uani 0.8778 1 d . . P A 1
H2C1 H 0.4854 0.2674 0.4684 0.020 Uiso 0.8778 1 calc R U P A 1
H2C2 H 0.5074 0.1876 0.3537 0.020 Uiso 0.8778 1 calc R U P A 1
C3C C 0.8594(6) 0.3147(3) 0.4243(2) 0.0168(6) Uani 0.8778 1 d . . P A 1
H3C1 H 0.9918 0.2606 0.3872 0.020 Uiso 0.8778 1 calc R U P A 1
H3C2 H 0.9373 0.3582 0.4939 0.020 Uiso 0.8778 1 calc R U P A 1
C3C' C 0.618(4) 0.295(2) 0.3841(14) 0.017(4) Uiso 0.1222 1 d . . P A 2
H3C3 H 0.4724 0.3213 0.4271 0.021 Uiso 0.1222 1 calc R U P A 2
H3C4 H 0.5378 0.2364 0.3172 0.021 Uiso 0.1222 1 calc R U P A 2
C2C' C 0.808(5) 0.224(2) 0.4267(14) 0.019(4) Uiso 0.1222 1 d . . P A 2
H2C3 H 0.9005 0.2894 0.4898 0.023 Uiso 0.1222 1 calc R U P A 2
H2C4 H 0.9471 0.1965 0.3808 0.023 Uiso 0.1222 1 calc R U P A 2
C4C C 0.8112(6) 0.4280(3) 0.3809(2) 0.0244(6) Uani 1 1 d D . . . .
H4C1 H 0.757(7) 0.382(3) 0.3117(12) 0.029 Uiso 1 1 d D U . . .
H4C2 H 0.635(4) 0.456(3) 0.399(2) 0.029 Uiso 1 1 d D U . . .
C5C C 1.0401(6) 0.5450(3) 0.41516(18) 0.0216(5) Uani 1 1 d . . . . .
H5C1 H 1.2106 0.5057 0.4078 0.026 Uiso 1 1 calc R U . . .
H5C2 H 1.0329 0.5934 0.4865 0.026 Uiso 1 1 calc R U . . .
C6C C 1.0478(5) 0.6506(2) 0.36218(16) 0.0143(5) Uani 1 1 d . . . . .
H6C H 1.1965 0.7272 0.3969 0.017 Uiso 1 1 calc R U . . .
N6C N 0.7925(4) 0.71078(19) 0.36640(14) 0.0133(4) Uani 1 1 d D . . . .
H6C1 H 0.656(5) 0.655(3) 0.3234(18) 0.016 Uiso 1 1 d D U . . .
H6C2 H 0.738(6) 0.730(3) 0.4277(13) 0.016 Uiso 1 1 d D U . . .
H6C3 H 0.815(6) 0.789(2) 0.350(2) 0.016 Uiso 1 1 d D U . . .
C7C C 1.1080(5) 0.5898(2) 0.25395(16) 0.0136(4) Uani 1 1 d . . . . .
O72C O 0.9299(3) 0.57641(17) 0.18676(12) 0.0158(3) Uani 1 1 d . . . . .
O71C O 1.3391(4) 0.55576(19) 0.24261(12) 0.0209(4) Uani 1 1 d . . . . .
N1D N 1.4197(4) 0.4226(2) 0.04826(14) 0.0133(4) Uani 1 1 d D . . . .
H1D1 H 1.555(5) 0.462(3) 0.023(2) 0.016 Uiso 1 1 d D U . . .
H1D2 H 1.267(4) 0.407(3) 0.0059(18) 0.016 Uiso 1 1 d D U . . .
H1D3 H 1.407(6) 0.484(2) 0.1096(13) 0.016 Uiso 1 1 d D U . . .
C2D C 1.4700(5) 0.2883(2) 0.05795(17) 0.0143(5) Uani 1 1 d . . . . .
H2D1 H 1.6117 0.3046 0.1126 0.017 Uiso 1 1 calc R U . . .
H2D2 H 1.5332 0.2307 -0.0039 0.017 Uiso 1 1 calc R U . . .
C3D C 1.2134(5) 0.2136(2) 0.07847(18) 0.0172(5) Uani 1 1 d . . . . .
H3D1 H 1.0796 0.1881 0.0201 0.021 Uiso 1 1 calc R U . . .
H3D2 H 1.1385 0.2766 0.1351 0.021 Uiso 1 1 calc R U . . .
C4D C 1.2603(5) 0.0837(2) 0.10164(18) 0.0163(5) Uani 1 1 d . . . . .
H4D1 H 1.3823 0.1097 0.1632 0.020 Uiso 1 1 calc R U . . .
H4D2 H 1.3482 0.0238 0.0474 0.020 Uiso 1 1 calc R U . . .
C5D C 0.9956(5) 0.0041(2) 0.11400(17) 0.0156(5) Uani 1 1 d . . . . .
H5D1 H 0.8754 -0.0220 0.0520 0.019 Uiso 1 1 calc R U . . .
H5D2 H 0.9070 0.0655 0.1673 0.019 Uiso 1 1 calc R U . . .
C6D C 1.0306(5) -0.1265(2) 0.13898(17) 0.0139(5) Uani 1 1 d . . . . .
H6D H 1.1452 -0.1823 0.0916 0.017 Uiso 1 1 calc R U . . .
N6D N 0.7608(4) -0.20885(19) 0.13034(14) 0.0128(4) Uani 1 1 d D . . . .
H6D1 H 0.782(6) -0.283(2) 0.149(2) 0.015 Uiso 1 1 d D U . . .
H6D2 H 0.660(5) -0.159(3) 0.1758(17) 0.015 Uiso 1 1 d D U . . .
H6D3 H 0.680(6) -0.228(3) 0.0677(13) 0.015 Uiso 1 1 d D U . . .
C7D C 1.1626(5) -0.0891(2) 0.24545(16) 0.0136(4) Uani 1 1 d . . . . .
O72D O 1.0088(3) -0.06305(17) 0.31311(12) 0.0160(3) Uani 1 1 d . . . . .
O71D O 1.4118(4) -0.08268(19) 0.25718(12) 0.0210(4) Uani 1 1 d . . . . .
O1W O 0.5992(4) 0.74207(18) 0.54580(12) 0.0172(4) Uani 1 1 d D . . . .
H1W1 H 0.480(5) 0.792(3) 0.568(2) 0.021 Uiso 1 1 d D U . . .
H1W2 H 0.566(7) 0.673(2) 0.565(2) 0.021 Uiso 1 1 d D U . . .
O2W O -0.4939(4) 0.75554(17) 0.94360(12) 0.0162(4) Uani 1 1 d D . . . .
H2W1 H -0.379(5) 0.710(3) 0.913(2) 0.019 Uiso 1 1 d D U . . .
H2W2 H -0.478(7) 0.824(2) 0.923(2) 0.019 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
N1A C2A 1.370(3) . ?
N1A C6A 1.383(3) . ?
N1A H1A 0.873(14) . ?
C2A O2A 1.224(3) . ?
C2A N3A 1.373(3) . ?
N3A C4A 1.379(3) . ?
N3A H3A 0.868(14) . ?
C4A O4A 1.236(3) . ?
C4A C5A 1.456(3) . ?
C5A N5A 1.334(3) . ?
C5A C6A 1.454(3) . ?
N5A O5A' 1.233(6) . ?
N5A O5A 1.261(3) . ?
C6A O6A 1.232(3) . ?
N1B C2B 1.373(3) . ?
N1B C6B 1.378(3) . ?
N1B H1B 0.872(14) . ?
C2B O2B 1.221(3) . ?
C2B N3B 1.376(3) . ?
N3B C4B 1.380(3) . ?
N3B H3B 0.870(14) . ?
C4B O4B 1.235(3) . ?
C4B C5B 1.456(3) . ?
C5B N5B 1.340(3) . ?
C5B C6B 1.457(3) . ?
N5B O5B 1.278(3) . ?
C6B O6B 1.229(3) . ?
N1C C2C 1.481(3) . ?
N1C C2C' 1.51(2) . ?
N1C H1C1 0.897(14) . ?
N1C H1C2 0.892(14) . ?
N1C H1C3 0.903(14) . ?
C2C C3C 1.514(4) . ?
C2C H2C1 0.9900 . ?
C2C H2C2 0.9900 . ?
C3C C4C 1.531(3) . ?
C3C H3C1 0.9900 . ?
C3C H3C2 0.9900 . ?
C3C' C2C' 1.50(3) . ?
C3C' C4C 1.60(2) . ?
C3C' H3C3 0.9900 . ?
C3C' H3C4 0.9900 . ?
C2C' H2C3 0.9900 . ?
C2C' H2C4 0.9900 . ?
C4C C5C 1.500(4) . ?
C4C H4C1 0.960(14) . ?
C4C H4C2 0.990(14) . ?
C5C C6C 1.516(3) . ?
C5C H5C1 0.9900 . ?
C5C H5C2 0.9900 . ?
C6C N6C 1.491(3) . ?
C6C C7C 1.539(3) . ?
C6C H6C 1.0000 . ?
N6C H6C1 0.901(14) . ?
N6C H6C2 0.903(14) . ?
N6C H6C3 0.904(14) . ?
C7C O72C 1.243(3) . ?
C7C O71C 1.260(3) . ?
N1D C2D 1.490(3) . ?
N1D H1D1 0.900(14) . ?
N1D H1D2 0.918(14) . ?
N1D H1D3 0.915(14) . ?
C2D C3D 1.514(3) . ?
C2D H2D1 0.9900 . ?
C2D H2D2 0.9900 . ?
C3D C4D 1.526(3) . ?
C3D H3D1 0.9900 . ?
C3D H3D2 0.9900 . ?
C4D C5D 1.529(3) . ?
C4D H4D1 0.9900 . ?
C4D H4D2 0.9900 . ?
C5D C6D 1.532(3) . ?
C5D H5D1 0.9900 . ?
C5D H5D2 0.9900 . ?
C6D N6D 1.489(3) . ?
C6D C7D 1.542(3) . ?
C6D H6D 1.0000 . ?
N6D H6D1 0.908(14) . ?
N6D H6D2 0.913(14) . ?
N6D H6D3 0.916(14) . ?
C7D O71D 1.247(3) . ?
C7D O72D 1.256(3) . ?
O1W H1W1 0.848(14) . ?
O1W H1W2 0.844(14) . ?
O2W H2W1 0.844(14) . ?
O2W H2W2 0.841(14) . ?

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
C2A N1A C6A 126.3(2) . . ?
C2A N1A H1A 120(2) . . ?
C6A N1A H1A 113(2) . . ?
O2A C2A N1A 122.2(2) . . ?
O2A C2A N3A 121.9(2) . . ?
N1A C2A N3A 115.9(2) . . ?
C2A N3A C4A 125.7(2) . . ?
C2A N3A H3A 116(2) . . ?
C4A N3A H3A 118(2) . . ?
O4A C4A N3A 119.0(2) . . ?
O4A C4A C5A 124.4(2) . . ?
N3A C4A C5A 116.6(2) . . ?
N5A C5A C6A 124.9(2) . . ?
N5A C5A C4A 115.5(2) . . ?
C6A C5A C4A 119.6(2) . . ?
O5A' N5A O5A 100.9(7) . . ?
O5A' N5A C5A 134.6(6) . . ?
O5A N5A C5A 120.1(2) . . ?
O6A C6A N1A 118.6(2) . . ?
O6A C6A C5A 125.4(2) . . ?
N1A C6A C5A 116.0(2) . . ?
C2B N1B C6B 126.7(2) . . ?
C2B N1B H1B 116(2) . . ?
C6B N1B H1B 117(2) . . ?
O2B C2B N1B 122.4(2) . . ?
O2B C2B N3B 122.0(2) . . ?
N1B C2B N3B 115.6(2) . . ?
C2B N3B C4B 125.7(2) . . ?
C2B N3B H3B 118(2) . . ?
C4B N3B H3B 116(2) . . ?
O4B C4B N3B 119.3(2) . . ?
O4B C4B C5B 124.3(2) . . ?
N3B C4B C5B 116.5(2) . . ?
N5B C5B C4B 114.64(19) . . ?
N5B C5B C6B 125.5(2) . . ?
C4B C5B C6B 119.7(2) . . ?
O5B N5B C5B 118.53(19) . . ?
O6B C6B N1B 118.6(2) . . ?
O6B C6B C5B 125.7(2) . . ?
N1B C6B C5B 115.8(2) . . ?
C2C N1C H1C1 108(2) . . ?
C2C' N1C H1C1 147(2) . . ?
C2C N1C H1C2 110(2) . . ?
C2C' N1C H1C2 90(2) . . ?
H1C1 N1C H1C2 112(3) . . ?
C2C N1C H1C3 117.9(19) . . ?
C2C' N1C H1C3 89(2) . . ?
H1C1 N1C H1C3 109(3) . . ?
H1C2 N1C H1C3 101(3) . . ?
N1C C2C C3C 109.8(2) . . ?
N1C C2C H2C1 109.7 . . ?
C3C C2C H2C1 109.7 . . ?
N1C C2C H2C2 109.7 . . ?
C3C C2C H2C2 109.7 . . ?
H2C1 C2C H2C2 108.2 . . ?
C2C C3C C4C 112.7(2) . . ?
C2C C3C H3C1 109.1 . . ?
C4C C3C H3C1 109.1 . . ?
C2C C3C H3C2 109.1 . . ?
C4C C3C H3C2 109.1 . . ?
H3C1 C3C H3C2 107.8 . . ?
C2C' C3C' C4C 101.9(15) . . ?
C2C' C3C' H3C3 111.4 . . ?
C4C C3C' H3C3 111.4 . . ?
C2C' C3C' H3C4 111.4 . . ?
C4C C3C' H3C4 111.4 . . ?
H3C3 C3C' H3C4 109.3 . . ?
C3C' C2C' N1C 113.2(17) . . ?
C3C' C2C' H2C3 108.9 . . ?
N1C C2C' H2C3 108.9 . . ?
C3C' C2C' H2C4 108.9 . . ?
N1C C2C' H2C4 108.9 . . ?
H2C3 C2C' H2C4 107.8 . . ?
C5C C4C C3C 110.5(2) . . ?
C5C C4C C3C' 156.6(7) . . ?
C5C C4C H4C1 121(2) . . ?
C3C C4C H4C1 106(2) . . ?
C3C' C4C H4C1 79(2) . . ?
C5C C4C H4C2 113(2) . . ?
C3C C4C H4C2 108.0(19) . . ?
C3C' C4C H4C2 72(2) . . ?
H4C1 C4C H4C2 96(3) . . ?
C4C C5C C6C 116.1(2) . . ?
C4C C5C H5C1 108.3 . . ?
C6C C5C H5C1 108.3 . . ?
C4C C5C H5C2 108.3 . . ?
C6C C5C H5C2 108.3 . . ?
H5C1 C5C H5C2 107.4 . . ?
N6C C6C C5C 111.60(19) . . ?
N6C C6C C7C 109.90(19) . . ?
C5C C6C C7C 112.01(19) . . ?
N6C C6C H6C 107.7 . . ?
C5C C6C H6C 107.7 . . ?
C7C C6C H6C 107.7 . . ?
C6C N6C H6C1 114.0(19) . . ?
C6C N6C H6C2 109.9(19) . . ?
H6C1 N6C H6C2 108(3) . . ?
C6C N6C H6C3 110.8(19) . . ?
H6C1 N6C H6C3 105(3) . . ?
H6C2 N6C H6C3 109(3) . . ?
O72C C7C O71C 126.0(2) . . ?
O72C C7C C6C 119.0(2) . . ?
O71C C7C C6C 115.0(2) . . ?
C2D N1D H1D1 112.5(19) . . ?
C2D N1D H1D2 108.5(18) . . ?
H1D1 N1D H1D2 108(3) . . ?
C2D N1D H1D3 109.2(18) . . ?
H1D1 N1D H1D3 106(3) . . ?
H1D2 N1D H1D3 113(3) . . ?
N1D C2D C3D 109.74(19) . . ?
N1D C2D H2D1 109.7 . . ?
C3D C2D H2D1 109.7 . . ?
N1D C2D H2D2 109.7 . . ?
C3D C2D H2D2 109.7 . . ?
H2D1 C2D H2D2 108.2 . . ?
C2D C3D C4D 112.1(2) . . ?
C2D C3D H3D1 109.2 . . ?
C4D C3D H3D1 109.2 . . ?
C2D C3D H3D2 109.2 . . ?
C4D C3D H3D2 109.2 . . ?
H3D1 C3D H3D2 107.9 . . ?
C3D C4D C5D 111.2(2) . . ?
C3D C4D H4D1 109.4 . . ?
C5D C4D H4D1 109.4 . . ?
C3D C4D H4D2 109.4 . . ?
C5D C4D H4D2 109.4 . . ?
H4D1 C4D H4D2 108.0 . . ?
C4D C5D C6D 113.5(2) . . ?
C4D C5D H5D1 108.9 . . ?
C6D C5D H5D1 108.9 . . ?
C4D C5D H5D2 108.9 . . ?
C6D C5D H5D2 108.9 . . ?
H5D1 C5D H5D2 107.7 . . ?
N6D C6D C5D 108.72(18) . . ?
N6D C6D C7D 108.84(18) . . ?
C5D C6D C7D 110.71(18) . . ?
N6D C6D H6D 109.5 . . ?
C5D C6D H6D 109.5 . . ?
C7D C6D H6D 109.5 . . ?
C6D N6D H6D1 108.2(19) . . ?
C6D N6D H6D2 109.2(19) . . ?
H6D1 N6D H6D2 104(3) . . ?
C6D N6D H6D3 108.8(19) . . ?
H6D1 N6D H6D3 116(3) . . ?
H6D2 N6D H6D3 110(3) . . ?
O71D C7D O72D 125.9(2) . . ?
O71D C7D C6D 117.6(2) . . ?
O72D C7D C6D 116.5(2) . . ?
H1W1 O1W H1W2 105(3) . . ?
H2W1 O2W H2W2 101(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
C6A N1A C2A O2A 179.1(2) . . . . ?
C6A N1A C2A N3A -1.0(4) . . . . ?
O2A C2A N3A C4A -179.0(2) . . . . ?
N1A C2A N3A C4A 1.1(4) . . . . ?
C2A N3A C4A O4A 178.6(2) . . . . ?
C2A N3A C4A C5A -1.1(4) . . . . ?
O4A C4A C5A N5A -1.4(4) . . . . ?
N3A C4A C5A N5A 178.2(2) . . . . ?
O4A C4A C5A C6A -178.8(2) . . . . ?
N3A C4A C5A C6A 0.8(3) . . . . ?
C6A C5A N5A O5A' -153.5(10) . . . . ?
C4A C5A N5A O5A' 29.3(10) . . . . ?
C6A C5A N5A O5A -1.9(4) . . . . ?
C4A C5A N5A O5A -179.1(2) . . . . ?
C2A N1A C6A O6A -179.1(2) . . . . ?
C2A N1A C6A C5A 0.8(4) . . . . ?
N5A C5A C6A O6A 2.1(4) . . . . ?
C4A C5A C6A O6A 179.2(2) . . . . ?
N5A C5A C6A N1A -177.8(2) . . . . ?
C4A C5A C6A N1A -0.7(3) . . . . ?
C6B N1B C2B O2B 179.8(2) . . . . ?
C6B N1B C2B N3B 0.2(4) . . . . ?
O2B C2B N3B C4B 179.1(2) . . . . ?
N1B C2B N3B C4B -1.3(4) . . . . ?
C2B N3B C4B O4B -179.2(2) . . . . ?
C2B N3B C4B C5B 1.4(4) . . . . ?
O4B C4B C5B N5B 3.4(3) . . . . ?
N3B C4B C5B N5B -177.2(2) . . . . ?
O4B C4B C5B C6B -179.8(2) . . . . ?
N3B C4B C5B C6B -0.4(3) . . . . ?
C4B C5B N5B O5B -178.77(19) . . . . ?
C6B C5B N5B O5B 4.6(4) . . . . ?
C2B N1B C6B O6B -179.6(2) . . . . ?
C2B N1B C6B C5B 0.7(4) . . . . ?
N5B C5B C6B O6B -3.8(4) . . . . ?
C4B C5B C6B O6B 179.8(2) . . . . ?
N5B C5B C6B N1B 175.9(2) . . . . ?
C4B C5B C6B N1B -0.6(3) . . . . ?
C2C' N1C C2C C3C -6.2(12) . . . . ?
N1C C2C C3C C4C 169.1(2) . . . . ?
C4C C3C' C2C' N1C 175.7(11) . . . . ?
C2C N1C C2C' C3C' -11.8(9) . . . . ?
C2C C3C C4C C5C 161.4(2) . . . . ?
C2C C3C C4C C3C' -7.1(9) . . . . ?
C2C' C3C' C4C C5C -35(3) . . . . ?
C2C' C3C' C4C C3C -6.5(8) . . . . ?
C3C C4C C5C C6C 168.1(2) . . . . ?
C3C' C4C C5C C6C -169.9(18) . . . . ?
C4C C5C C6C N6C 55.8(3) . . . . ?
C4C C5C C6C C7C -67.9(3) . . . . ?
N6C C6C C7C O72C -11.7(3) . . . . ?
C5C C6C C7C O72C 112.9(2) . . . . ?
N6C C6C C7C O71C 169.35(19) . . . . ?
C5C C6C C7C O71C -66.0(3) . . . . ?
N1D C2D C3D C4D -173.00(18) . . . . ?
C2D C3D C4D C5D -175.50(19) . . . . ?
C3D C4D C5D C6D -179.12(18) . . . . ?
C4D C5D C6D N6D -169.33(18) . . . . ?
C4D C5D C6D C7D 71.2(3) . . . . ?
N6D C6D C7D O71D 146.1(2) . . . . ?
C5D C6D C7D O71D -94.5(2) . . . . ?
N6D C6D C7D O72D -36.4(3) . . . . ?
C5D C6D C7D O72D 83.1(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
N1A H1A O6B 0.873(14) 1.945(14) 2.817(3) 177(3) .
N3A H3A O4B 0.868(14) 1.983(14) 2.849(2) 175(3) 1_465
N1B H1B O6A 0.872(14) 1.948(15) 2.816(2) 173(3) .
N3B H3B O4A 0.870(14) 1.975(14) 2.843(3) 176(3) 1_645
N1C H1C1 N5A 0.897(14) 2.61(2) 3.416(3) 149(3) 1_545
N1C H1C1 O5A 0.897(14) 1.978(19) 2.802(3) 152(3) 1_545
N1C H1C1 O5A' 0.897(14) 2.14(3) 2.789(13) 128(3) 1_545
N1C H1C2 O72D 0.892(14) 2.002(16) 2.870(3) 164(3) .
N1C H1C2 O71D 0.892(14) 2.44(3) 2.876(3) 110(2) 1_455
N1C H1C3 O4A 0.903(14) 2.20(2) 2.874(2) 131(2) 1_645
N1C H1C3 N5A 0.903(14) 2.342(19) 3.160(3) 151(3) 1_645
N1C H1C3 O5A' 0.903(14) 2.13(2) 2.938(14) 148(3) 1_645
C2C H2C1 O5A' 0.99 2.37 2.957(10) 117.6 1_545
C2C' H2C4 O72D 0.99 2.61 3.21(2) 118.8 .
C6C H6C O5A 1.00 2.53 3.392(3) 143.6 1_655
N6C H6C1 O71C 0.901(14) 1.895(15) 2.791(3) 172(3) 1_455
N6C H6C2 O1W 0.903(14) 1.840(15) 2.736(2) 171(3) .
N6C H6C3 O72D 0.904(14) 1.950(18) 2.803(2) 157(3) 1_565
N1D H1D1 N5B 0.900(14) 2.657(18) 3.494(3) 155(2) 1_754
N1D H1D1 O5B 0.900(14) 1.900(15) 2.789(3) 170(3) 1_754
N1D H1D2 O4B 0.918(14) 2.45(3) 2.952(2) 115(2) 1_654
N1D H1D2 N5B 0.918(14) 2.182(18) 3.042(3) 156(3) 1_654
N1D H1D3 O71C 0.915(14) 1.880(16) 2.763(2) 161(3) .
C2D H2D2 O2A 0.99 2.60 3.496(3) 150.3 1_744
N6D H6D1 O72C 0.908(14) 1.920(16) 2.804(2) 164(3) 1_545
N6D H6D2 O71D 0.913(14) 1.830(15) 2.735(3) 171(3) 1_455
N6D H6D3 O5B 0.916(14) 2.60(3) 3.044(2) 110(2) 1_644
N6D H6D3 O2W 0.916(14) 1.890(15) 2.802(3) 173(3) 1_644
O1W H1W1 O5A 0.848(14) 2.19(2) 2.869(3) 137(3) .
O1W H1W1 O6A 0.848(14) 2.03(2) 2.758(2) 144(3) .
O1W H1W2 O2B 0.844(14) 2.028(15) 2.870(2) 175(3) .
O2W H2W1 O5B 0.844(14) 2.27(3) 2.836(2) 125(3) .
O2W H2W1 O6B 0.844(14) 1.985(19) 2.776(2) 156(3) .
O2W H2W2 O2A 0.841(14) 2.059(15) 2.900(2) 177(3) .

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2008005'
loop_
_audit_author_name
_audit_author_address
'Katarzyna Stadnicka'
;Jagiellonian University Cracow
Poland
;
_audit_update_record             
;
2020-06-04 deposited with the CCDC.	2024-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
2-azaniumyl-3-(4-hydroxyphenyl)propanoate-5-(hydroxyimino)
-1,3-diazinane-2-,4,6-trione-water (1/1/3)
;
_chemical_name_common            
;
l-tyrosine-violuric acid trihydrate <1/1/3>
;
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C4 H3 N3 O4, C9 H11 N O3, 3(H2 O)
;
_chemical_formula_sum            'C13 H20 N4 O10'
_chemical_formula_weight         392.33

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   6.7731(2)
_cell_length_b                   14.3180(3)
_cell_length_c                   17.8700(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1732.98(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    24901
_cell_measurement_theta_min      1.8280
_cell_measurement_theta_max      31.4940

_exptl_crystal_description       needle
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.130
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.54533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.26a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            63253
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.823
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3981
_reflns_number_gt                3667
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro 1.171.40.26a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.26a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.26a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae, 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0456P)²+0.3779P] 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 1487 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 rm
_refine_ls_number_reflns         3981
_refine_ls_number_parameters     274
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0792
_refine_ls_wR_factor_gt          0.0771
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_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
N1A N 0.4908(3) 1.22829(11) 0.36579(9) 0.0169(4) Uani 1 1 d D . . . .
H1A H 0.512(4) 1.2859(10) 0.3802(13) 0.020 Uiso 1 1 d D U . . .
C2A C 0.4686(3) 1.21500(13) 0.28964(11) 0.0143(4) Uani 1 1 d . . . . .
O2A O 0.4856(3) 1.27805(9) 0.24517(8) 0.0198(3) Uani 1 1 d . . . . .
N3A N 0.4243(3) 1.12519(11) 0.26721(9) 0.0136(3) Uani 1 1 d D . . . .
H3A H 0.413(4) 1.1158(17) 0.2188(7) 0.016 Uiso 1 1 d D U . . .
C4A C 0.4057(3) 1.04861(14) 0.31229(11) 0.0135(4) Uani 1 1 d . . . . .
O4A O 0.3622(2) 0.97262(9) 0.28606(8) 0.0161(3) Uani 1 1 d . . . . .
C5A C 0.4457(3) 1.06441(14) 0.39338(10) 0.0138(4) Uani 1 1 d . . . . .
N5A N 0.4526(3) 0.98673(12) 0.43115(9) 0.0157(3) Uani 1 1 d . . . . .
O5A O 0.4979(2) 0.99642(10) 0.50423(7) 0.0188(3) Uani 1 1 d D . . . .
H5A H 0.503(4) 0.9415(7) 0.5209(13) 0.023 Uiso 1 1 d D U . . .
C6A C 0.4783(3) 1.16138(14) 0.42095(11) 0.0172(4) Uani 1 1 d . . . . .
O6A O 0.4936(3) 1.18267(10) 0.48641(8) 0.0262(4) Uani 1 1 d . . . . .
C1B C 0.4576(3) 0.34541(13) 0.69278(11) 0.0146(4) Uani 1 1 d . . . . .
O1B O 0.4831(3) 0.25924(9) 0.72483(8) 0.0189(3) Uani 1 1 d D . . . .
H1B H 0.520(4) 0.2192(14) 0.6934(11) 0.023 Uiso 1 1 d D U . . .
C2B C 0.4746(3) 0.35944(13) 0.61559(11) 0.0147(4) Uani 1 1 d . . . . .
H2B H 0.5035 0.3085 0.5833 0.018 Uiso 1 1 calc R U . . .
C3B C 0.4488(3) 0.44891(14) 0.58653(11) 0.0152(4) Uani 1 1 d . . . . .
H3B H 0.4608 0.4586 0.5341 0.018 Uiso 1 1 calc R U . . .
C4B C 0.4056(3) 0.52464(13) 0.63297(11) 0.0141(4) Uani 1 1 d . . . . .
C5B C 0.3880(3) 0.50863(14) 0.70934(11) 0.0158(4) Uani 1 1 d . . . . .
H5B H 0.3576 0.5594 0.7416 0.019 Uiso 1 1 calc R U . . .
C6B C 0.4141(3) 0.41989(14) 0.73970(11) 0.0166(4) Uani 1 1 d . . . . .
H6B H 0.4021 0.4104 0.7921 0.020 Uiso 1 1 calc R U . . .
C7B C 0.3771(3) 0.62153(14) 0.60096(12) 0.0157(4) Uani 1 1 d . . . . .
H7B1 H 0.3154 0.6618 0.6395 0.019 Uiso 1 1 calc R U . . .
H7B2 H 0.2852 0.6179 0.5580 0.019 Uiso 1 1 calc R U . . .
C8B C 0.5706(3) 0.66670(13) 0.57503(10) 0.0124(4) Uani 1 1 d . . . . .
H8B H 0.6382 0.6226 0.5400 0.015 Uiso 1 1 calc R U . . .
N8B N 0.7048(2) 0.68496(11) 0.63933(9) 0.0118(3) Uani 1 1 d . . . . .
H8B1 H 0.8182 0.7117 0.6224 0.018 Uiso 1 1 calc R U . . .
H8B2 H 0.6445 0.7242 0.6722 0.018 Uiso 1 1 calc R U . . .
H8B3 H 0.7337 0.6301 0.6626 0.018 Uiso 1 1 calc R U . . .
C9B C 0.5252(3) 0.75733(12) 0.53239(10) 0.0119(4) Uani 1 1 d . . . . .
O92B O 0.5273(2) 0.83311(9) 0.56874(8) 0.0156(3) Uani 1 1 d . . . . .
O91B O 0.4823(2) 0.74808(9) 0.46496(7) 0.0164(3) Uani 1 1 d . . . . .
O1W O 0.6447(2) 0.60611(10) 0.38629(9) 0.0183(3) Uani 1 1 d D . . . .
H11W H 0.587(4) 0.6446(15) 0.4142(13) 0.022 Uiso 1 1 d D U . . .
H12W H 0.762(2) 0.6203(18) 0.3920(15) 0.022 Uiso 1 1 d D U . . .
O2W O 0.4997(3) 0.42513(10) 0.36350(8) 0.0262(4) Uani 1 1 d D . . . .
H21W H 0.532(5) 0.424(2) 0.3180(8) 0.031 Uiso 1 1 d D U . . .
H22W H 0.553(4) 0.4732(14) 0.3817(15) 0.031 Uiso 1 1 d D U . . .
O3W O 0.5925(3) 0.12475(12) 0.63148(9) 0.0271(4) Uani 1 1 d D . . . .
H31W H 0.561(4) 0.121(2) 0.5869(8) 0.033 Uiso 1 1 d D U . . .
H32W H 0.712(2) 0.111(2) 0.6289(16) 0.033 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
N1A C6A 1.377(2) . ?
N1A C2A 1.382(3) . ?
N1A H1A 0.877(12) . ?
C2A O2A 1.208(2) . ?
C2A N3A 1.380(2) . ?
N3A C4A 1.366(2) . ?
N3A H3A 0.880(12) . ?
C4A O4A 1.221(2) . ?
C4A C5A 1.491(3) . ?
C5A N5A 1.302(3) . ?
C5A C6A 1.490(3) . ?
N5A O5A 1.349(2) . ?
O5A H5A 0.841(3) . ?
C6A O6A 1.213(2) . ?
C1B O1B 1.371(2) . ?
C1B C6B 1.388(3) . ?
C1B C2B 1.399(3) . ?
O1B H1B 0.840(13) . ?
C2B C3B 1.393(3) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.396(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.389(3) . ?
C4B C7B 1.513(3) . ?
C5B C6B 1.393(3) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.533(3) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B N8B 1.488(2) . ?
C8B C9B 1.536(3) . ?
C8B H8B 1.0000 . ?
N8B H8B1 0.9100 . ?
N8B H8B2 0.9100 . ?
N8B H8B3 0.9100 . ?
C9B O91B 1.246(2) . ?
C9B O92B 1.265(2) . ?
O1W H11W 0.839(13) . ?
O1W H12W 0.829(13) . ?
O2W H21W 0.842(13) . ?
O2W H22W 0.841(13) . ?
O3W H31W 0.828(13) . ?
O3W H32W 0.834(13) . ?

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
C6A N1A C2A 127.02(16) . . ?
C6A N1A H1A 117.0(16) . . ?
C2A N1A H1A 116.0(16) . . ?
O2A C2A N3A 121.74(18) . . ?
O2A C2A N1A 122.29(18) . . ?
N3A C2A N1A 115.97(16) . . ?
C4A N3A C2A 126.62(17) . . ?
C4A N3A H3A 116.7(16) . . ?
C2A N3A H3A 116.6(16) . . ?
O4A C4A N3A 120.74(18) . . ?
O4A C4A C5A 123.50(17) . . ?
N3A C4A C5A 115.75(17) . . ?
N5A C5A C6A 128.28(17) . . ?
N5A C5A C4A 112.37(17) . . ?
C6A C5A C4A 119.31(16) . . ?
C5A N5A O5A 114.98(16) . . ?
N5A O5A H5A 104.8(17) . . ?
O6A C6A N1A 120.67(18) . . ?
O6A C6A C5A 124.45(18) . . ?
N1A C6A C5A 114.88(16) . . ?
O1B C1B C6B 117.75(17) . . ?
O1B C1B C2B 122.07(17) . . ?
C6B C1B C2B 120.18(17) . . ?
C1B O1B H1B 111.8(17) . . ?
C3B C2B C1B 119.30(18) . . ?
C3B C2B H2B 120.3 . . ?
C1B C2B H2B 120.3 . . ?
C2B C3B C4B 121.24(18) . . ?
C2B C3B H3B 119.4 . . ?
C4B C3B H3B 119.4 . . ?
C5B C4B C3B 118.27(18) . . ?
C5B C4B C7B 120.79(18) . . ?
C3B C4B C7B 120.93(18) . . ?
C4B C5B C6B 121.50(19) . . ?
C4B C5B H5B 119.3 . . ?
C6B C5B H5B 119.3 . . ?
C1B C6B C5B 119.50(18) . . ?
C1B C6B H6B 120.2 . . ?
C5B C6B H6B 120.2 . . ?
C4B C7B C8B 113.08(16) . . ?
C4B C7B H7B1 109.0 . . ?
C8B C7B H7B1 109.0 . . ?
C4B C7B H7B2 109.0 . . ?
C8B C7B H7B2 109.0 . . ?
H7B1 C7B H7B2 107.8 . . ?
N8B C8B C7B 111.29(16) . . ?
N8B C8B C9B 110.90(15) . . ?
C7B C8B C9B 109.60(15) . . ?
N8B C8B H8B 108.3 . . ?
C7B C8B H8B 108.3 . . ?
C9B C8B H8B 108.3 . . ?
C8B N8B H8B1 109.5 . . ?
C8B N8B H8B2 109.5 . . ?
H8B1 N8B H8B2 109.5 . . ?
C8B N8B H8B3 109.5 . . ?
H8B1 N8B H8B3 109.5 . . ?
H8B2 N8B H8B3 109.5 . . ?
O91B C9B O92B 126.17(16) . . ?
O91B C9B C8B 115.88(16) . . ?
O92B C9B C8B 117.90(15) . . ?
H11W O1W H12W 102(3) . . ?
H21W O2W H22W 107(3) . . ?
H31W O3W H32W 101(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
C6A N1A C2A O2A -178.7(2) . . . . ?
C6A N1A C2A N3A 1.7(3) . . . . ?
O2A C2A N3A C4A 178.6(2) . . . . ?
N1A C2A N3A C4A -1.8(3) . . . . ?
C2A N3A C4A O4A 178.62(19) . . . . ?
C2A N3A C4A C5A -2.6(3) . . . . ?
O4A C4A C5A N5A 7.8(3) . . . . ?
N3A C4A C5A N5A -170.96(17) . . . . ?
O4A C4A C5A C6A -174.07(19) . . . . ?
N3A C4A C5A C6A 7.2(3) . . . . ?
C6A C5A N5A O5A -1.0(3) . . . . ?
C4A C5A N5A O5A 176.91(17) . . . . ?
C2A N1A C6A O6A -177.3(2) . . . . ?
C2A N1A C6A C5A 2.8(3) . . . . ?
N5A C5A C6A O6A -9.3(4) . . . . ?
C4A C5A C6A O6A 172.8(2) . . . . ?
N5A C5A C6A N1A 170.6(2) . . . . ?
C4A C5A C6A N1A -7.2(3) . . . . ?
O1B C1B C2B C3B -179.43(19) . . . . ?
C6B C1B C2B C3B 0.4(3) . . . . ?
C1B C2B C3B C4B -0.2(3) . . . . ?
C2B C3B C4B C5B -0.2(3) . . . . ?
C2B C3B C4B C7B -179.80(19) . . . . ?
C3B C4B C5B C6B 0.5(3) . . . . ?
C7B C4B C5B C6B -179.92(18) . . . . ?
O1B C1B C6B C5B 179.70(19) . . . . ?
C2B C1B C6B C5B -0.2(3) . . . . ?
C4B C5B C6B C1B -0.3(3) . . . . ?
C5B C4B C7B C8B 107.6(2) . . . . ?
C3B C4B C7B C8B -72.8(2) . . . . ?
C4B C7B C8B N8B -65.8(2) . . . . ?
C4B C7B C8B C9B 171.14(16) . . . . ?
N8B C8B C9B O91B 153.40(18) . . . . ?
C7B C8B C9B O91B -83.3(2) . . . . ?
N8B C8B C9B O92B -29.2(2) . . . . ?
C7B C8B C9B O92B 94.1(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
N1A H1A O2W 0.877(12) 2.017(16) 2.819(2) 151(2) 1_565
N3A H3A O1W 0.880(12) 1.922(13) 2.796(2) 172(2) 3_655
O5A H5A O92B 0.841(3) 1.780(5) 2.6146(19) 171(3) .
O1B H1B O3W 0.840(13) 1.816(13) 2.653(2) 175(3) .
C2B H2B O6A 0.95 2.50 3.428(2) 165.5 1_545
C8B H8B N5A 1.00 2.69 3.396(3) 127.5 4_566
N8B H8B1 O91B 0.91 2.00 2.815(2) 148.1 4_566
N8B H8B2 O1B 0.91 2.09 2.940(2) 154.3 3_656
N8B H8B3 O4A 0.91 1.94 2.829(2) 165.3 4_566
O1W H11W O91B 0.839(13) 1.877(14) 2.705(2) 169(3) .
O1W H12W O92B 0.829(13) 2.039(14) 2.849(2) 166(3) 4_566
O2W H21W O2A 0.842(13) 2.48(3) 2.986(2) 120(2) 1_545
O2W H21W O4A 0.842(13) 2.113(16) 2.912(2) 158(3) 3_645
O2W H22W O1W 0.841(13) 2.004(16) 2.801(2) 158(3) .
O3W H31W O5A 0.828(13) 2.35(2) 2.993(2) 135(2) 1_545
O3W H31W O6A 0.828(13) 2.053(18) 2.803(2) 150(3) 1_545
O3W H32W O2W 0.834(13) 2.021(14) 2.850(3) 173(3) 4_556

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.042



