# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ia304
_database_code_depnum_ccdc_archive 'CCDC 1997338'
loop_
_audit_author_name
_audit_author_address
'Eric C. Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N4 O2, H2 O'
_chemical_formula_sum            'C7 H10 N4 O3'
_chemical_formula_weight         198.19

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   4.4720(2)
_cell_length_b                   15.3544(5)
_cell_length_c                   13.1342(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.953(2)
_cell_angle_gamma                90
_cell_volume                     893.18(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5939
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      28.13

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.668
_exptl_crystal_size_mid          0.376
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9179
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            12776
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.052
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2214
_reflns_number_gt                1959
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The H atoms of the methyl group C6 were allowed to rotate with a fixed angle
around the C---C bonds to best fit the experimental electron density (HFIX 137
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(C).

The methyl group C5 shows rotational disorder with two positions rotated from
each other by 60 degrees. The H atoms of the methyl group were allowed to rotate
with a fixed angle around the C---C bond to best fit the experimental electron
density (HFIX 123 in the SHELXL program (Sheldrick, 2015)), with
Uiso(H) set to 1.5 Ueq(C).

The nitrogen-bound H atom was located on the difference Fourier map and refined
freely.

The H atoms of the water molecule O3 were located on a difference Fourier map
and refined with the O---H bond length and the H---O---H bond angle restrained
to 0.84 Å and 109 ° respectively. One of the H atoms is disordered over
positions H3B and H3C.

A reflection with large difference between its observed and calculated
intensities was omitted. This is due to obstruction by the beam stop.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+0.6489P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2214
_refine_ls_number_parameters     146
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.172
_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
O1 O -0.1772(3) 0.24269(9) 0.20394(10) 0.0343(3) Uani 1 1 d . . . . .
O2 O 0.1630(3) 0.48808(8) 0.38026(10) 0.0326(3) Uani 1 1 d . . . . .
O3 O 0.7597(4) 0.04577(9) 0.52718(14) 0.0469(4) Uani 1 1 d D . . . .
N1 N 0.2210(3) 0.22599(9) 0.32961(11) 0.0239(3) Uani 1 1 d . . . . .
N2 N -0.0010(3) 0.36462(9) 0.29202(10) 0.0235(3) Uani 1 1 d . . . . .
N3 N 0.6271(3) 0.36802(9) 0.50614(11) 0.0242(3) Uani 1 1 d . . . . .
N4 N 0.6416(3) 0.22596(9) 0.46931(11) 0.0258(3) Uani 1 1 d . . . . .
C1 C 0.3985(4) 0.35254(10) 0.42625(12) 0.0220(3) Uani 1 1 d . . . . .
C2 C 0.4142(3) 0.26519(10) 0.40612(12) 0.0218(3) Uani 1 1 d . . . . .
C3 C 0.0040(4) 0.27491(11) 0.27119(12) 0.0244(3) Uani 1 1 d . . . . .
C4 C 0.1881(4) 0.40881(10) 0.36886(12) 0.0230(3) Uani 1 1 d . . . . .
C5 C 0.2382(5) 0.13235(11) 0.31054(16) 0.0361(4) Uani 1 1 d . . . . .
H5A H 0.083643 0.116084 0.253357 0.054 Uiso 0.5 1 calc R U P . .
H5B H 0.438426 0.117932 0.293062 0.054 Uiso 0.5 1 calc R U P . .
H5C H 0.204007 0.100308 0.372423 0.054 Uiso 0.5 1 calc R U P . .
H5D H 0.400407 0.106799 0.359204 0.054 Uiso 0.5 1 calc R U P . .
H5E H 0.045625 0.104950 0.319499 0.054 Uiso 0.5 1 calc R U P . .
H5F H 0.280044 0.122575 0.240138 0.054 Uiso 0.5 1 calc R U P . .
C6 C -0.2199(4) 0.41697(12) 0.22362(14) 0.0328(4) Uani 1 1 d . . . . .
H6A H -0.129331 0.434910 0.163127 0.049 Uiso 1 1 calc R U . . .
H6B H -0.275208 0.468745 0.260475 0.049 Uiso 1 1 calc R U . . .
H6C H -0.400992 0.382105 0.201744 0.049 Uiso 1 1 calc R U . . .
C7 C 0.7619(4) 0.29102(11) 0.52861(13) 0.0262(4) Uani 1 1 d . . . . .
H7 H 0.927140 0.283558 0.581679 0.031 Uiso 1 1 calc R U . . .
H3 H 0.672(5) 0.4219(15) 0.5376(17) 0.036(6) Uiso 1 1 d . . . . .
H3A H 0.747(6) 0.0971(8) 0.505(2) 0.061(8) Uiso 1 1 d D . . . .
H3B H 0.597(5) 0.022(2) 0.503(3) 0.048(15) Uiso 0.61(5) 1 d D . P . .
H3C H 0.893(15) 0.022(3) 0.498(6) 0.08(4) Uiso 0.39(5) 1 d D . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.218(2) . ?
O2 C4 1.233(2) . ?
O3 H3A 0.841(10) . ?
O3 H3B 0.838(10) . ?
O3 H3C 0.839(10) . ?
N1 C2 1.370(2) . ?
N1 C3 1.374(2) . ?
N1 C5 1.463(2) . ?
N2 C4 1.399(2) . ?
N2 C3 1.405(2) . ?
N2 C6 1.473(2) . ?
N3 C7 1.341(2) . ?
N3 C1 1.380(2) . ?
N3 H3 0.93(2) . ?
N4 C7 1.333(2) . ?
N4 C2 1.361(2) . ?
C1 C2 1.371(2) . ?
C1 C4 1.415(2) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5 H5D 0.9800 . ?
C5 H5E 0.9800 . ?
C5 H5F 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7 0.9500 . ?

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
H3A O3 H3B 105(2) . . ?
H3A O3 H3C 106(2) . . ?
H3B O3 H3C 105(7) . . ?
C2 N1 C3 119.61(13) . . ?
C2 N1 C5 120.95(14) . . ?
C3 N1 C5 119.42(14) . . ?
C4 N2 C3 126.27(13) . . ?
C4 N2 C6 117.37(14) . . ?
C3 N2 C6 116.32(13) . . ?
C7 N3 C1 106.17(14) . . ?
C7 N3 H3 128.3(13) . . ?
C1 N3 H3 125.5(13) . . ?
C7 N4 C2 103.39(13) . . ?
C2 C1 N3 105.24(14) . . ?
C2 C1 C4 122.85(14) . . ?
N3 C1 C4 131.87(15) . . ?
N4 C2 N1 126.50(14) . . ?
N4 C2 C1 111.67(14) . . ?
N1 C2 C1 121.82(14) . . ?
O1 C3 N1 122.04(16) . . ?
O1 C3 N2 120.83(15) . . ?
N1 C3 N2 117.13(14) . . ?
O2 C4 N2 120.66(14) . . ?
O2 C4 C1 127.06(15) . . ?
N2 C4 C1 112.27(14) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
H5D C5 H5E 109.5 . . ?
H5D C5 H5F 109.5 . . ?
H5E C5 H5F 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 N3 113.53(14) . . ?
N4 C7 H7 123.2 . . ?
N3 C7 H7 123.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N3 C1 C2 -0.13(18) . . . . ?
C7 N3 C1 C4 -177.84(18) . . . . ?
C7 N4 C2 N1 179.51(16) . . . . ?
C7 N4 C2 C1 0.47(19) . . . . ?
C3 N1 C2 N4 -179.18(16) . . . . ?
C5 N1 C2 N4 2.1(3) . . . . ?
C3 N1 C2 C1 -0.2(2) . . . . ?
C5 N1 C2 C1 -178.94(16) . . . . ?
N3 C1 C2 N4 -0.22(19) . . . . ?
C4 C1 C2 N4 177.75(15) . . . . ?
N3 C1 C2 N1 -179.31(14) . . . . ?
C4 C1 C2 N1 -1.3(3) . . . . ?
C2 N1 C3 O1 -178.29(16) . . . . ?
C5 N1 C3 O1 0.4(3) . . . . ?
C2 N1 C3 N2 1.8(2) . . . . ?
C5 N1 C3 N2 -179.44(16) . . . . ?
C4 N2 C3 O1 177.96(16) . . . . ?
C6 N2 C3 O1 -4.3(2) . . . . ?
C4 N2 C3 N1 -2.2(2) . . . . ?
C6 N2 C3 N1 175.57(15) . . . . ?
C3 N2 C4 O2 -179.88(16) . . . . ?
C6 N2 C4 O2 2.4(2) . . . . ?
C3 N2 C4 C1 0.7(2) . . . . ?
C6 N2 C4 C1 -177.01(15) . . . . ?
C2 C1 C4 O2 -178.31(18) . . . . ?
N3 C1 C4 O2 -0.9(3) . . . . ?
C2 C1 C4 N2 1.1(2) . . . . ?
N3 C1 C4 N2 178.44(16) . . . . ?
C2 N4 C7 N3 -0.6(2) . . . . ?
C1 N3 C7 N4 0.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 O2 0.93(2) 1.84(2) 2.7572(18) 165(2) 3_666 yes
O3 H3A N4 0.841(10) 2.071(11) 2.898(2) 167(3) . yes
O3 H3B O3 0.838(10) 1.898(12) 2.724(3) 168(4) 3_656 yes
C5 H5A O1 0.98 2.31 2.750(2) 106 . yes
C6 H6B O2 0.98 2.36 2.717(2) 101 . yes
C7 H7 O1 0.95 2.26 3.204(2) 176 4_766 yes

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_ia360
_database_code_depnum_ccdc_archive 'CCDC 1997340'
loop_
_audit_author_name
_audit_author_address
'Eric C. Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 Cl N8 Na O10'
_chemical_formula_sum            'C14 H20 Cl N8 Na O10'
_chemical_formula_weight         518.82

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'
Cl Cl 0.1484 0.1585 '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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   20.7314(7)
_cell_length_b                   9.6579(3)
_cell_length_c                   10.6217(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.531(2)
_cell_angle_gamma                90
_cell_volume                     2124.62(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.563
_exptl_crystal_size_mid          0.486
_exptl_crystal_size_min          0.306
_exptl_absorpt_coefficient_mu    0.273
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9370
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            19274
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.967
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2644
_reflns_number_gt                2313
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The H atoms of the methyl groups were allowed to rotate with a fixed angle
around the C---C bonds to best fit the experimental electron density (HFIX 137
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(C).

The nitrogen-bound H atom was located on the difference Fourier map and refined
freely.

The H atoms of the water molecules were located on a difference Fourier map and
refined with the O---H bond lengths and the H---O---H bond angles restrained to
0.84 Å and 109 ° respectively.

The structure contains a coordinated CLO₄ ion which is disordered around a 2-
fold rotational axis. The Cl---O bond lengths were all restrained to the same
value.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+1.5510P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2644
_refine_ls_number_parameters     191
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Na1 Na 0.500000 0.84453(8) 0.250000 0.02707(17) Uani 1 2 d S T P . .
O3 O 0.55160(5) 0.74195(13) 0.41963(9) 0.0383(3) Uani 1 1 d D . . . .
O11 O 0.40776(5) 0.81078(10) 0.36218(9) 0.0313(2) Uani 1 1 d . . . . .
O12 O 0.33276(4) 0.41508(9) 0.54243(8) 0.0282(2) Uani 1 1 d . . . . .
N11 N 0.34310(5) 0.83782(10) 0.52685(9) 0.0219(2) Uani 1 1 d . . . . .
N12 N 0.37004(4) 0.61485(10) 0.45233(9) 0.0209(2) Uani 1 1 d . . . . .
N13 N 0.26360(5) 0.60686(11) 0.72127(9) 0.0221(2) Uani 1 1 d . . . . .
N14 N 0.27304(5) 0.83672(11) 0.70528(10) 0.0237(2) Uani 1 1 d . . . . .
C11 C 0.30288(5) 0.63293(12) 0.62235(10) 0.0199(2) Uani 1 1 d . . . . .
C12 C 0.30780(5) 0.77356(12) 0.61572(10) 0.0196(2) Uani 1 1 d . . . . .
C13 C 0.37568(5) 0.75841(13) 0.44307(11) 0.0218(2) Uani 1 1 d . . . . .
C14 C 0.33487(5) 0.54236(12) 0.54021(10) 0.0202(2) Uani 1 1 d . . . . .
C15 C 0.35052(7) 0.98832(13) 0.52687(14) 0.0331(3) Uani 1 1 d . . . . .
H15A H 0.381624 1.014961 0.464383 0.050 Uiso 1 1 calc R U . . .
H15B H 0.366191 1.019191 0.610633 0.050 Uiso 1 1 calc R U . . .
H15C H 0.308718 1.031724 0.505622 0.050 Uiso 1 1 calc R U . . .
C16 C 0.40638(6) 0.53453(14) 0.36192(12) 0.0289(3) Uani 1 1 d . . . . .
H16A H 0.398817 0.573154 0.277229 0.043 Uiso 1 1 calc R U . . .
H16B H 0.392023 0.437873 0.362634 0.043 Uiso 1 1 calc R U . . .
H16C H 0.452572 0.538961 0.385532 0.043 Uiso 1 1 calc R U . . .
C17 C 0.24754(6) 0.73059(12) 0.76673(11) 0.0247(2) Uani 1 1 d . . . . .
H17 H 0.220592 0.742014 0.836046 0.030 Uiso 1 1 calc R U . . .
H3A H 0.5871(6) 0.706(2) 0.4358(19) 0.061(6) Uiso 1 1 d D . . . .
H3B H 0.5333(9) 0.746(2) 0.4876(13) 0.062(6) Uiso 1 1 d D . . . .
H13 H 0.2501(8) 0.5195(18) 0.7492(17) 0.041(5) Uiso 1 1 d . . . . .
Cl2 Cl 0.50865(14) 1.20039(6) 0.2498(5) 0.0306(5) Uani 0.5 1 d D . P A -1
O21 O 0.4732(2) 1.0844(3) 0.2872(3) 0.0834(11) Uani 0.5 1 d D . P A -1
O22 O 0.4733(4) 1.2755(9) 0.1565(7) 0.080(2) Uani 0.5 1 d D . P A -1
O23 O 0.56921(15) 1.1612(4) 0.2002(3) 0.0663(8) Uani 0.5 1 d D . P A -1
O24 O 0.5225(3) 1.2882(5) 0.3557(5) 0.0310(8) Uani 0.5 1 d D . P A -1


_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
Na1 O3 2.2808(11) 2_655 ?
Na1 O3 2.2808(11) . ?
Na1 O11 2.3203(9) . ?
Na1 O11 2.3203(9) 2_655 ?
Na1 O21 2.419(3) . ?
O3 H3A 0.827(9) . ?
O3 H3B 0.831(9) . ?
O11 C13 1.2193(14) . ?
O12 C14 1.2302(15) . ?
N11 C12 1.3685(14) . ?
N11 C13 1.3745(15) . ?
N11 C15 1.4617(16) . ?
N12 C13 1.3953(16) . ?
N12 C14 1.3977(14) . ?
N12 C16 1.4681(14) . ?
N13 C17 1.3365(15) . ?
N13 C11 1.3807(14) . ?
N13 H13 0.942(17) . ?
N14 C17 1.3367(16) . ?
N14 C12 1.3627(14) . ?
C11 C12 1.3640(16) . ?
C11 C14 1.4203(15) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17 0.9500 . ?
Cl2 O22 1.407(8) . ?
Cl2 O21 1.407(3) . ?
Cl2 O24 1.428(6) . ?
Cl2 O23 1.433(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Na1 O3 128.51(7) 2_655 . ?
O3 Na1 O11 88.64(4) 2_655 . ?
O3 Na1 O11 84.36(4) . . ?
O3 Na1 O11 84.36(4) 2_655 2_655 ?
O3 Na1 O11 88.64(4) . 2_655 ?
O11 Na1 O11 163.85(6) . 2_655 ?
O3 Na1 O21 116.21(11) 2_655 . ?
O3 Na1 O21 112.97(10) . . ?
O11 Na1 O21 81.37(8) . . ?
O11 Na1 O21 114.78(9) 2_655 . ?
Na1 O3 H3A 136.9(14) . . ?
Na1 O3 H3B 116.7(14) . . ?
H3A O3 H3B 106.0(17) . . ?
C13 O11 Na1 155.18(9) . . ?
C12 N11 C13 119.12(10) . . ?
C12 N11 C15 120.69(10) . . ?
C13 N11 C15 120.01(10) . . ?
C13 N12 C14 126.34(9) . . ?
C13 N12 C16 115.59(9) . . ?
C14 N12 C16 118.05(10) . . ?
C17 N13 C11 106.06(10) . . ?
C17 N13 H13 127.3(11) . . ?
C11 N13 H13 126.6(11) . . ?
C17 N14 C12 103.32(10) . . ?
C12 C11 N13 105.59(10) . . ?
C12 C11 C14 122.93(10) . . ?
N13 C11 C14 131.47(11) . . ?
N14 C12 C11 111.51(10) . . ?
N14 C12 N11 126.43(10) . . ?
C11 C12 N11 122.05(10) . . ?
O11 C13 N11 121.58(11) . . ?
O11 C13 N12 120.79(11) . . ?
N11 C13 N12 117.63(10) . . ?
O12 C14 N12 122.22(10) . . ?
O12 C14 C11 125.86(10) . . ?
N12 C14 C11 111.92(10) . . ?
N11 C15 H15A 109.5 . . ?
N11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N12 C16 H16A 109.5 . . ?
N12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N13 C17 N14 113.51(10) . . ?
N13 C17 H17 123.2 . . ?
N14 C17 H17 123.2 . . ?
O22 Cl2 O21 110.3(5) . . ?
O22 Cl2 O24 109.2(2) . . ?
O21 Cl2 O24 109.9(4) . . ?
O22 Cl2 O23 108.4(5) . . ?
O21 Cl2 O23 111.7(3) . . ?
O24 Cl2 O23 107.3(3) . . ?
Cl2 O21 Na1 126.1(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
C17 N13 C11 C12 0.17(13) . . . . ?
C17 N13 C11 C14 179.13(12) . . . . ?
C17 N14 C12 C11 0.54(13) . . . . ?
C17 N14 C12 N11 179.50(11) . . . . ?
N13 C11 C12 N14 -0.45(13) . . . . ?
C14 C11 C12 N14 -179.52(10) . . . . ?
N13 C11 C12 N11 -179.47(10) . . . . ?
C14 C11 C12 N11 1.46(17) . . . . ?
C13 N11 C12 N14 179.86(11) . . . . ?
C15 N11 C12 N14 4.76(18) . . . . ?
C13 N11 C12 C11 -1.28(16) . . . . ?
C15 N11 C12 C11 -176.38(11) . . . . ?
Na1 O11 C13 N11 127.66(19) . . . . ?
Na1 O11 C13 N12 -53.3(3) . . . . ?
C12 N11 C13 O11 179.99(11) . . . . ?
C15 N11 C13 O11 -4.88(18) . . . . ?
C12 N11 C13 N12 0.95(15) . . . . ?
C15 N11 C13 N12 176.08(11) . . . . ?
C14 N12 C13 O11 -179.92(11) . . . . ?
C16 N12 C13 O11 1.72(16) . . . . ?
C14 N12 C13 N11 -0.87(17) . . . . ?
C16 N12 C13 N11 -179.23(10) . . . . ?
C13 N12 C14 O12 -179.50(11) . . . . ?
C16 N12 C14 O12 -1.18(16) . . . . ?
C13 N12 C14 C11 0.95(15) . . . . ?
C16 N12 C14 C11 179.27(10) . . . . ?
C12 C11 C14 O12 179.26(11) . . . . ?
N13 C11 C14 O12 0.5(2) . . . . ?
C12 C11 C14 N12 -1.20(15) . . . . ?
N13 C11 C14 N12 179.99(11) . . . . ?
C11 N13 C17 N14 0.17(14) . . . . ?
C12 N14 C17 N13 -0.43(14) . . . . ?
O22 Cl2 O21 Na1 112.6(5) . . . . ?
O24 Cl2 O21 Na1 -127.0(4) . . . . ?
O23 Cl2 O21 Na1 -8.0(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3A O12 0.827(9) 2.034(10) 2.8503(14) 169(2) 5_666 yes
O3 H3B O24 0.831(9) 2.095(12) 2.910(5) 167(2) 5_676 yes
O3 H3B O22 0.831(9) 2.237(13) 3.059(8) 170(2) 6_576 yes
O3 H3B O23 0.831(9) 2.512(18) 3.130(3) 131.9(18) 6_576 yes
N13 H13 N14 0.942(17) 1.897(18) 2.8363(15) 175.2(16) 4_546 yes
C15 H15A O11 0.98 2.33 2.7553(17) 106 . yes
C15 H15A O23 0.98 2.50 3.425(3) 157 2_655 yes
C16 H16B O12 0.98 2.33 2.7559(15) 106 . yes
C17 H17 O12 0.95 2.41 3.2176(14) 143 4_556 yes

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.045

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ia333
_database_code_depnum_ccdc_archive 'CCDC 1997339'
loop_
_audit_author_name
_audit_author_address
'Eric C. Hosten'
;Nelson Mandela University
South Africa
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 N2, C7 H8 N4 O2, 2(H2 O)'
_chemical_formula_sum            'C19 H20 N6 O4'
_chemical_formula_weight         396.41

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

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

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

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

_cell_length_a                   9.3613(4)
_cell_length_b                   7.0465(3)
_cell_length_c                   14.5134(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.023(2)
_cell_angle_gamma                90
_cell_volume                     932.74(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5296
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.72

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.634
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8799
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            15674
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.233
_diffrn_reflns_theta_max         28.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             4419
_reflns_number_gt                3618
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_max     0.884
_reflns_Friedel_fraction_full    0.942

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (Hübschle, 2011)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material  
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'

_refine_special_details          
;
Carbon-bound H atoms were placed in calculated positions and were included in
the refinement in the riding model approximation, with Uiso(H) set to
1.2 Ueq(C).

The H atoms of the methyl groups were allowed to rotate with a fixed angle
around the C---C bonds to best fit the experimental electron density (HFIX 137
in the SHELXL program (Sheldrick, 2015)), with Uiso(H) set to
1.5Ueq(C).

The nitrogen-bound H atom was located on the difference Fourier map and refined
with the N---H bond length restrained to 0.88 Å.

The H atoms of the water molecules were located on a difference Fourier map and
refined with the O---H bond lengths and the H---O---H bond angles restrained to
0.84 Å and 109 ° respectively.

A reflection with large difference between its observed and calculated
intensities was omitted. This is due to obstruction by the beam stop.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_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 1327 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 unk
_refine_ls_number_reflns         4419
_refine_ls_number_parameters     284
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.023
_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
O3 O 0.8552(2) 0.5566(3) -0.01078(12) 0.0469(5) Uani 1 1 d D . . . .
O4 O 0.01768(18) 0.3064(3) 0.11489(13) 0.0382(4) Uani 1 1 d D . . . .
O11 O 0.62000(18) 0.6553(3) 0.06992(11) 0.0391(4) Uani 1 1 d . . . . .
O12 O 0.74047(16) 0.6187(3) 0.39313(11) 0.0346(4) Uani 1 1 d . . . . .
N11 N 0.43720(19) 0.5845(3) 0.14235(12) 0.0273(4) Uani 1 1 d . . . . .
N12 N 0.67763(19) 0.6384(3) 0.23102(12) 0.0268(4) Uani 1 1 d . . . . .
N13 N 0.41567(19) 0.5184(3) 0.37795(12) 0.0262(4) Uani 1 1 d D . . . .
N14 N 0.26167(18) 0.4973(3) 0.23572(12) 0.0273(4) Uani 1 1 d . . . . .
N21 N 0.52308(18) 0.5188(3) 0.57492(12) 0.0261(4) Uani 1 1 d . . . . .
N22 N 0.22956(18) 0.6029(3) 0.53049(11) 0.0277(4) Uani 1 1 d . . . . .
C11 C 0.3977(2) 0.5481(3) 0.22670(14) 0.0244(5) Uani 1 1 d . . . . .
C12 C 0.5805(2) 0.6272(3) 0.14379(16) 0.0283(5) Uani 1 1 d . . . . .
C13 C 0.6453(2) 0.6069(3) 0.32076(15) 0.0256(5) Uani 1 1 d . . . . .
C14 C 0.4952(2) 0.5615(3) 0.31171(14) 0.0228(5) Uani 1 1 d . . . . .
C15 C 0.3306(3) 0.5778(4) 0.05201(15) 0.0384(6) Uani 1 1 d . . . . .
H15A H 0.339580 0.692638 0.015635 0.058 Uiso 1 1 calc R U . . .
H15B H 0.231432 0.570415 0.063306 0.058 Uiso 1 1 calc R U . . .
H15C H 0.349242 0.465876 0.016387 0.058 Uiso 1 1 calc R U . . .
C16 C 0.8298(2) 0.6835(4) 0.22964(17) 0.0366(6) Uani 1 1 d . . . . .
H16A H 0.876886 0.571475 0.209556 0.055 Uiso 1 1 calc R U . . .
H16B H 0.882721 0.721393 0.293151 0.055 Uiso 1 1 calc R U . . .
H16C H 0.831693 0.787875 0.185294 0.055 Uiso 1 1 calc R U . . .
C17 C 0.2796(2) 0.4818(4) 0.32956(16) 0.0299(5) Uani 1 1 d . . . . .
H17 H 0.202369 0.447840 0.359036 0.036 Uiso 1 1 calc R U . . .
C21 C 0.4559(3) 0.6097(4) 0.81408(15) 0.0305(5) Uani 1 1 d . . . . .
H21 H 0.507584 0.609970 0.878415 0.037 Uiso 1 1 calc R U . . .
C22 C 0.3127(3) 0.6556(3) 0.79157(15) 0.0308(5) Uani 1 1 d . . . . .
H22 H 0.264920 0.689450 0.840422 0.037 Uiso 1 1 calc R U . . .
C211 C 0.4558(2) 0.5623(3) 0.64640(14) 0.0221(5) Uani 1 1 d . . . . .
C212 C 0.5309(2) 0.5603(3) 0.74151(15) 0.0263(5) Uani 1 1 d . . . . .
C213 C 0.6799(2) 0.5061(4) 0.76266(17) 0.0309(5) Uani 1 1 d . . . . .
H213 H 0.734007 0.500718 0.826400 0.037 Uiso 1 1 calc R U . . .
C214 C 0.7448(2) 0.4618(4) 0.69089(17) 0.0330(6) Uani 1 1 d . . . . .
H214 H 0.844941 0.424684 0.703776 0.040 Uiso 1 1 calc R U . . .
C215 C 0.6630(2) 0.4712(3) 0.59786(17) 0.0307(5) Uani 1 1 d . . . . .
H215 H 0.710642 0.441701 0.548341 0.037 Uiso 1 1 calc R U . . .
C221 C 0.3016(2) 0.6082(3) 0.62208(14) 0.0225(5) Uani 1 1 d . . . . .
C222 C 0.2312(2) 0.6544(3) 0.69583(15) 0.0254(5) Uani 1 1 d . . . . .
C223 C 0.0799(2) 0.6940(3) 0.67086(16) 0.0299(5) Uani 1 1 d . . . . .
H223 H 0.028218 0.724817 0.718190 0.036 Uiso 1 1 calc R U . . .
C224 C 0.0083(2) 0.6877(4) 0.57793(17) 0.0321(6) Uani 1 1 d . . . . .
H224 H -0.093775 0.713734 0.559522 0.038 Uiso 1 1 calc R U . . .
C225 C 0.0881(2) 0.6420(4) 0.51047(16) 0.0310(5) Uani 1 1 d . . . . .
H225 H 0.037270 0.638868 0.445975 0.037 Uiso 1 1 calc R U . . .
H3A H 0.783(3) 0.589(6) 0.010(2) 0.095(13) Uiso 1 1 d D . . . .
H3B H 0.916(2) 0.490(4) 0.0280(17) 0.054(9) Uiso 1 1 d D . . . .
H4A H 0.094(2) 0.359(4) 0.1490(19) 0.058(10) Uiso 1 1 d D . . . .
H4B H 0.055(3) 0.226(4) 0.084(2) 0.061(10) Uiso 1 1 d D . . . .
H13 H 0.443(3) 0.522(6) 0.4413(10) 0.080(11) Uiso 1 1 d 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
O3 H3A 0.830(13) . ?
O3 H3B 0.844(13) . ?
O4 H4A 0.855(13) . ?
O4 H4B 0.844(13) . ?
O11 C12 1.227(2) . ?
O12 C13 1.218(3) . ?
N11 C12 1.370(3) . ?
N11 C11 1.380(2) . ?
N11 C15 1.459(3) . ?
N12 C12 1.385(3) . ?
N12 C13 1.420(3) . ?
N12 C16 1.464(3) . ?
N13 C17 1.334(3) . ?
N13 C14 1.376(2) . ?
N13 H13 0.897(13) . ?
N14 C17 1.339(3) . ?
N14 C11 1.358(3) . ?
N21 C215 1.321(3) . ?
N21 C211 1.364(2) . ?
N22 C225 1.319(3) . ?
N22 C221 1.349(3) . ?
C11 C14 1.363(3) . ?
C13 C14 1.418(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17 0.9500 . ?
C21 C22 1.346(3) . ?
C21 C212 1.434(3) . ?
C21 H21 0.9500 . ?
C22 C222 1.427(3) . ?
C22 H22 0.9500 . ?
C211 C212 1.401(3) . ?
C211 C221 1.443(3) . ?
C212 C213 1.412(3) . ?
C213 C214 1.355(3) . ?
C213 H213 0.9500 . ?
C214 C215 1.396(3) . ?
C214 H214 0.9500 . ?
C215 H215 0.9500 . ?
C221 C222 1.416(3) . ?
C222 C223 1.409(3) . ?
C223 C224 1.365(3) . ?
C223 H223 0.9500 . ?
C224 C225 1.397(3) . ?
C224 H224 0.9500 . ?
C225 H225 0.9500 . ?

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
H3A O3 H3B 113(3) . . ?
H4A O4 H4B 102(2) . . ?
C12 N11 C11 118.95(17) . . ?
C12 N11 C15 119.33(17) . . ?
C11 N11 C15 121.72(17) . . ?
C12 N12 C13 126.72(17) . . ?
C12 N12 C16 116.15(17) . . ?
C13 N12 C16 117.12(18) . . ?
C17 N13 C14 106.12(18) . . ?
C17 N13 H13 124(2) . . ?
C14 N13 H13 130(2) . . ?
C17 N14 C11 102.37(17) . . ?
C215 N21 C211 117.86(18) . . ?
C225 N22 C221 117.75(17) . . ?
N14 C11 C14 112.49(17) . . ?
N14 C11 N11 125.38(18) . . ?
C14 C11 N11 122.13(18) . . ?
O11 C12 N11 120.6(2) . . ?
O11 C12 N12 121.64(19) . . ?
N11 C12 N12 117.75(17) . . ?
O12 C13 C14 127.78(18) . . ?
O12 C13 N12 120.99(18) . . ?
C14 C13 N12 111.23(18) . . ?
C11 C14 N13 105.06(17) . . ?
C11 C14 C13 123.16(17) . . ?
N13 C14 C13 131.76(19) . . ?
N11 C15 H15A 109.5 . . ?
N11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N12 C16 H16A 109.5 . . ?
N12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N13 C17 N14 113.95(19) . . ?
N13 C17 H17 123.0 . . ?
N14 C17 H17 123.0 . . ?
C22 C21 C212 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C212 C21 H21 119.8 . . ?
C21 C22 C222 121.33(18) . . ?
C21 C22 H22 119.3 . . ?
C222 C22 H22 119.3 . . ?
N21 C211 C212 122.13(18) . . ?
N21 C211 C221 118.16(17) . . ?
C212 C211 C221 119.70(16) . . ?
C211 C212 C213 117.97(18) . . ?
C211 C212 C21 120.06(19) . . ?
C213 C212 C21 122.0(2) . . ?
C214 C213 C212 119.2(2) . . ?
C214 C213 H213 120.4 . . ?
C212 C213 H213 120.4 . . ?
C213 C214 C215 119.3(2) . . ?
C213 C214 H214 120.4 . . ?
C215 C214 H214 120.4 . . ?
N21 C215 C214 123.56(19) . . ?
N21 C215 H215 118.2 . . ?
C214 C215 H215 118.2 . . ?
N22 C221 C222 122.46(18) . . ?
N22 C221 C211 119.03(16) . . ?
C222 C221 C211 118.50(17) . . ?
C223 C222 C221 117.63(19) . . ?
C223 C222 C22 122.39(18) . . ?
C221 C222 C22 119.97(18) . . ?
C224 C223 C222 119.29(19) . . ?
C224 C223 H223 120.4 . . ?
C222 C223 H223 120.4 . . ?
C223 C224 C225 118.6(2) . . ?
C223 C224 H224 120.7 . . ?
C225 C224 H224 120.7 . . ?
N22 C225 C224 124.3(2) . . ?
N22 C225 H225 117.9 . . ?
C224 C225 H225 117.9 . . ?

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
C17 N14 C11 C14 0.5(2) . . . . ?
C17 N14 C11 N11 -179.1(2) . . . . ?
C12 N11 C11 N14 -177.5(2) . . . . ?
C15 N11 C11 N14 2.3(3) . . . . ?
C12 N11 C11 C14 3.0(3) . . . . ?
C15 N11 C11 C14 -177.3(2) . . . . ?
C11 N11 C12 O11 178.0(2) . . . . ?
C15 N11 C12 O11 -1.7(4) . . . . ?
C11 N11 C12 N12 -2.4(3) . . . . ?
C15 N11 C12 N12 177.9(2) . . . . ?
C13 N12 C12 O11 -179.2(2) . . . . ?
C16 N12 C12 O11 -0.6(3) . . . . ?
C13 N12 C12 N11 1.2(3) . . . . ?
C16 N12 C12 N11 179.7(2) . . . . ?
C12 N12 C13 O12 179.2(2) . . . . ?
C16 N12 C13 O12 0.6(3) . . . . ?
C12 N12 C13 C14 -0.4(3) . . . . ?
C16 N12 C13 C14 -179.0(2) . . . . ?
N14 C11 C14 N13 -0.5(3) . . . . ?
N11 C11 C14 N13 179.1(2) . . . . ?
N14 C11 C14 C13 178.1(2) . . . . ?
N11 C11 C14 C13 -2.4(3) . . . . ?
C17 N13 C14 C11 0.3(3) . . . . ?
C17 N13 C14 C13 -178.1(2) . . . . ?
O12 C13 C14 C11 -178.6(2) . . . . ?
N12 C13 C14 C11 1.0(3) . . . . ?
O12 C13 C14 N13 -0.4(4) . . . . ?
N12 C13 C14 N13 179.1(2) . . . . ?
C14 N13 C17 N14 0.0(3) . . . . ?
C11 N14 C17 N13 -0.3(3) . . . . ?
C212 C21 C22 C222 0.8(4) . . . . ?
C215 N21 C211 C212 1.0(3) . . . . ?
C215 N21 C211 C221 -177.9(2) . . . . ?
N21 C211 C212 C213 -1.8(3) . . . . ?
C221 C211 C212 C213 177.1(2) . . . . ?
N21 C211 C212 C21 179.1(2) . . . . ?
C221 C211 C212 C21 -2.0(3) . . . . ?
C22 C21 C212 C211 0.9(3) . . . . ?
C22 C21 C212 C213 -178.1(2) . . . . ?
C211 C212 C213 C214 1.2(3) . . . . ?
C21 C212 C213 C214 -179.7(2) . . . . ?
C212 C213 C214 C215 0.1(4) . . . . ?
C211 N21 C215 C214 0.5(3) . . . . ?
C213 C214 C215 N21 -1.0(4) . . . . ?
C225 N22 C221 C222 -0.3(3) . . . . ?
C225 N22 C221 C211 178.7(2) . . . . ?
N21 C211 C221 N22 1.3(3) . . . . ?
C212 C211 C221 N22 -177.6(2) . . . . ?
N21 C211 C221 C222 -179.7(2) . . . . ?
C212 C211 C221 C222 1.4(3) . . . . ?
N22 C221 C222 C223 0.6(3) . . . . ?
C211 C221 C222 C223 -178.4(2) . . . . ?
N22 C221 C222 C22 179.3(2) . . . . ?
C211 C221 C222 C22 0.3(3) . . . . ?
C21 C22 C222 C223 177.2(2) . . . . ?
C21 C22 C222 C221 -1.4(4) . . . . ?
C221 C222 C223 C224 -0.4(3) . . . . ?
C22 C222 C223 C224 -179.0(2) . . . . ?
C222 C223 C224 C225 -0.1(4) . . . . ?
C221 N22 C225 C224 -0.3(4) . . . . ?
C223 C224 C225 N22 0.4(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
_geom_hbond_publ_flag
O3 H3A O11 0.830(13) 1.977(14) 2.805(2) 175(3) . yes
O3 H3B O4 0.844(13) 1.907(15) 2.738(3) 168(3) 1_655 yes
O4 H4A N14 0.855(13) 2.028(13) 2.880(3) 174(3) . yes
O4 H4B O3 0.844(13) 1.916(14) 2.758(3) 176(3) 2_645 yes
N13 H13 N21 0.897(13) 1.916(14) 2.809(3) 173(3) . yes
C15 H15B N14 0.98 2.51 2.936(3) 106 . yes
C15 H15C O11 0.98 2.57 3.546(3) 175 2_645 yes
C16 H16B O12 0.98 2.30 2.726(3) 106 . yes
C213 H213 O3 0.95 2.41 3.347(3) 168 1_556 yes

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039

