# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1828849'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2018-03-11 deposited with the CCDC.	2019-07-09 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 N2 O2, 1.786(H2 O2), 0.214(H2 O)'
_chemical_formula_sum            'C4 H10 N2 O5.786'
_chemical_formula_weight         178.72

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5006(8)
_cell_length_b                   5.8258(8)
_cell_length_c                   6.5611(9)
_cell_angle_alpha                76.395(2)
_cell_angle_beta                 67.816(2)
_cell_angle_gamma                79.145(2)
_cell_volume                     188.07(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1537
_cell_measurement_theta_min      3.409
_cell_measurement_theta_max      30.461

_exptl_crystal_description       nugget
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             94
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9498
_exptl_absorpt_correction_T_max  0.9824
_exptl_absorpt_process_details   'SADABS (bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1974
_diffrn_reflns_av_R_equivalents  0.0085
_diffrn_reflns_av_sigmaI/netI    0.0094
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         28.00
_reflns_number_total             909
_reflns_number_gt                837
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0544P)²+0.0529P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         909
_refine_ls_number_parameters     100
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5205(2) 0.78638(18) 0.25672(18) 0.0490(3) Uani 1 1 d . . .
N1 N 0.30220(18) 0.35587(16) 0.06518(16) 0.0310(3) Uani 1 1 d . . .
C1 C 0.5159(2) 0.65578(19) 0.1331(2) 0.0310(3) Uani 1 1 d . . .
C2 C 0.2896(2) 0.5080(2) 0.21518(19) 0.0325(3) Uani 1 1 d . . .
H10 H 0.174(4) 0.260(3) 0.108(3) 0.050(4) Uiso 1 1 d . . .
H21 H 0.288(3) 0.413(3) 0.361(3) 0.047(4) Uiso 1 1 d . . .
H22 H 0.130(3) 0.618(3) 0.241(3) 0.044(4) Uiso 1 1 d . . .
O2 O 0.1095(3) 0.9540(3) 0.6021(3) 0.0413(5) Uani 0.548(3) 1 d PD A 1
O3 O 0.2103(6) 0.8630(5) 0.7851(4) 0.0412(6) Uani 0.548(3) 1 d PD A 1
O4 O 0.2498(6) 0.7728(6) 0.6698(5) 0.0358(9) Uani 0.345(5) 1 d PD B 2
O5 O 0.0971(6) 0.9763(8) 0.7570(7) 0.0447(11) Uani 0.345(5) 1 d PD B 2
H1 H 0.260(5) 0.851(3) 0.514(4) 0.081(7) Uiso 0.893(6) 1 d PD . .
H2 H 0.242(4) 1.024(3) 0.790(5) 0.082(7) Uiso 0.893(6) 1 d PD . .
O6 O 0.174(2) 0.876(2) 0.7273(18) 0.016(3) Uiso 0.107(6) 1 d P C 3
H3 H 0.2665 0.8523 0.6048 0.024 Uiso 0.107(6) 1 c PR C 3
H4 H 0.2600 0.9695 0.7334 0.024 Uiso 0.107(6) 1 c PR C 3


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2452(14) . ?
N1 C1 1.3159(15) 2_665 ?
N1 C2 1.4473(14) . ?
N1 H10 0.90(2) . ?
C1 C2 1.5032(15) . ?
C2 H21 0.987(18) . ?
C2 H22 0.966(17) . ?
O2 O3 1.457(3) . ?
O2 H1 0.995(18) . ?
O3 H2 0.994(18) . ?
O4 O5 1.421(5) . ?
O4 H1 1.003(18) . ?
O5 H2 1.000(19) . ?
O6 H3 0.8000 . ?
O6 H4 0.8000 . ?

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
C1 N1 C2 126.14(9) 2_665 . ?
C1 N1 H10 115.5(11) 2_665 . ?
C2 N1 H10 118.3(11) . . ?
O1 C1 N1 122.89(10) . 2_665 ?
O1 C1 C2 117.93(10) . . ?
N1 C1 C2 119.17(10) 2_665 . ?
N1 C2 C1 114.64(9) . . ?
N1 C2 H21 110.6(9) . . ?
C1 C2 H21 106.4(10) . . ?
N1 C2 H22 110.6(9) . . ?
C1 C2 H22 106.4(10) . . ?
H21 C2 H22 107.9(14) . . ?
O3 O2 H1 86.4(10) . . ?
O2 O3 H2 92.7(12) . . ?
O5 O4 H1 91.4(10) . . ?
O4 O5 H2 94.7(11) . . ?
H3 O6 H4 96.2 . . ?

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
H1 O2 O3 H2 119(2) . . . . ?
H1 O4 O5 H2 -109(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
O2 H1 O1 0.995(18) 1.82(2) 2.746(2) 153.1(14) .
O4 H1 O1 1.003(18) 1.82(2) 2.543(3) 125.9(10) .
O3 H2 O1 0.994(18) 1.76(2) 2.647(3) 146.3(16) 2_676
O5 H2 O1 1.000(19) 1.76(2) 2.690(3) 152.6(18) 2_676
O6 H3 O1 0.80 2.26 3.062(13) 179.0 .
O6 H4 O1 0.80 2.06 2.857(10) 178.9 2_676
N1 H10 O2 0.90(2) 2.233(19) 3.018(2) 145.5(15) 2_566
N1 H10 O3 0.90(2) 2.17(2) 3.035(3) 161.9(15) 2_566
N1 H10 O4 0.90(2) 2.252(19) 3.010(3) 141.7(14) 2_566
N1 H10 O5 0.90(2) 2.03(2) 2.921(3) 171.7(16) 2_566
N1 H10 O6 0.90(2) 2.02(2) 2.886(9) 160.9(16) 2_566

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_16per09
_database_code_depnum_ccdc_archive 'CCDC 1828852'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2018-03-11 deposited with the CCDC.	2019-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H10 N2 O2, 2(H2 O2)'
_chemical_formula_sum            'C6 H14 N2 O6'
_chemical_formula_weight         210.19

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1 '
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.439(2)
_cell_length_b                   8.215(2)
_cell_length_c                   8.298(2)
_cell_angle_alpha                97.332(4)
_cell_angle_beta                 104.578(4)
_cell_angle_gamma                104.053(4)
_cell_volume                     466.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3310
_cell_measurement_theta_min      2.589
_cell_measurement_theta_max      30.609

_exptl_crystal_description       nugget
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9737
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4702
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         25.03
_reflns_number_total             1610
_reflns_number_gt                1340
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0960P)²+0.2098P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1610
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1594
_refine_ls_wR_factor_gt          0.1517
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5063(2) -0.0951(2) 0.6666(2) 0.0238(5) Uani 1 1 d . . .
O2 O 1.0291(3) 0.4907(2) 0.7155(2) 0.0242(5) Uani 1 1 d . . .
N1 N 0.8178(3) 0.0508(3) 0.7124(3) 0.0194(5) Uani 1 1 d . . .
H1 H 0.848(4) -0.041(4) 0.687(4) 0.026(8) Uiso 1 1 d . . .
N2 N 0.7273(3) 0.3501(3) 0.7078(3) 0.0207(5) Uani 1 1 d . . .
H2 H 0.688(5) 0.434(5) 0.688(4) 0.031(8) Uiso 1 1 d . . .
C1 C 0.6369(4) 0.0425(3) 0.7021(3) 0.0189(6) Uani 1 1 d . . .
C2 C 0.5854(3) 0.2071(3) 0.7340(3) 0.0204(6) Uani 1 1 d . . .
H21 H 0.4581 0.1940 0.6492 0.024 Uiso 1 1 calc R . .
C3 C 0.5600(4) 0.2421(3) 0.9098(4) 0.0272(6) Uani 1 1 d . . .
H3A H 0.5170 0.3453 0.9238 0.041 Uiso 1 1 calc R . .
H3B H 0.6838 0.2591 0.9961 0.041 Uiso 1 1 calc R . .
H3C H 0.4627 0.1443 0.9230 0.041 Uiso 1 1 calc R . .
C4 C 0.9097(4) 0.3602(3) 0.7259(3) 0.0189(6) Uani 1 1 d . . .
C5 C 0.9786(3) 0.2087(3) 0.7669(3) 0.0196(6) Uani 1 1 d . . .
H51 H 1.0729 0.1961 0.7024 0.023 Uiso 1 1 calc R . .
C6 C 1.0846(4) 0.2398(3) 0.9550(3) 0.0246(6) Uani 1 1 d . . .
H6A H 1.1355 0.1432 0.9788 0.037 Uiso 1 1 calc R . .
H6B H 0.9946 0.2509 1.0213 0.037 Uiso 1 1 calc R . .
H6C H 1.1920 0.3454 0.9864 0.037 Uiso 1 1 calc R . .
O3 O 0.3380(3) 0.4699(2) 0.6022(2) 0.0276(5) Uani 1 1 d . . .
O4 O 0.5058(3) 0.5883(2) 0.7317(2) 0.0250(5) Uani 1 1 d . . .
H3 H 0.246(5) 0.480(4) 0.647(5) 0.039(9) Uiso 1 1 d . . .
H4 H 0.496(6) 0.668(5) 0.692(5) 0.049(12) Uiso 1 1 d . . .
O5 O 0.9972(3) 0.7870(3) 0.6207(2) 0.0290(5) Uani 1 1 d . . .
O6 O 1.1698(3) 0.8968(2) 0.7497(3) 0.0323(5) Uani 1 1 d . . .
H5 H 0.983(5) 0.682(5) 0.644(4) 0.042(9) Uiso 1 1 d . . .
H6 H 1.257(6) 0.882(5) 0.691(5) 0.057(11) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.243(3) . ?
O2 C4 1.243(3) . ?
N1 C1 1.312(3) . ?
N1 C5 1.463(3) . ?
N1 H1 0.86(3) . ?
N2 C4 1.308(3) . ?
N2 C2 1.456(3) . ?
N2 H2 0.83(4) . ?
C1 C2 1.502(4) . ?
C2 C3 1.518(4) . ?
C2 H21 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.503(3) . ?
C5 C6 1.518(4) . ?
C5 H51 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
O3 O4 1.458(3) . ?
O3 H3 0.87(4) . ?
O4 H4 0.78(4) . ?
O5 O6 1.452(3) . ?
O5 H5 0.89(4) . ?
O6 H6 0.93(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 124.9(2) . . ?
C1 N1 H1 120(2) . . ?
C5 N1 H1 116(2) . . ?
C4 N2 C2 125.4(2) . . ?
C4 N2 H2 119(2) . . ?
C2 N2 H2 115(2) . . ?
O1 C1 N1 123.1(2) . . ?
O1 C1 C2 118.6(2) . . ?
N1 C1 C2 118.3(2) . . ?
N2 C2 C1 111.3(2) . . ?
N2 C2 C3 111.4(2) . . ?
C1 C2 C3 111.3(2) . . ?
N2 C2 H21 107.5 . . ?
C1 C2 H21 107.5 . . ?
C3 C2 H21 107.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 N2 123.1(2) . . ?
O2 C4 C5 118.7(2) . . ?
N2 C4 C5 118.2(2) . . ?
N1 C5 C4 111.1(2) . . ?
N1 C5 C6 111.8(2) . . ?
C4 C5 C6 110.3(2) . . ?
N1 C5 H51 107.8 . . ?
C4 C5 H51 107.8 . . ?
C6 C5 H51 107.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 O3 H3 100(2) . . ?
O3 O4 H4 95(3) . . ?
O6 O5 H5 106(2) . . ?
O5 O6 H6 96(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
H3 O3 O4 H4 -88(4) . . . . ?
H5 O5 O6 H6 89(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O5 0.86(3) 2.09(4) 2.924(3) 163(3) 1_545
N2 H2 O4 0.83(4) 2.13(4) 2.866(3) 147(3) .
O3 H3 O2 0.87(4) 1.86(4) 2.726(3) 173(3) 1_455
O4 H4 O1 0.78(4) 1.97(4) 2.723(3) 162(4) 1_565
O5 H5 O2 0.89(4) 1.83(4) 2.698(3) 164(3) .
O6 H6 O1 0.93(5) 1.88(5) 2.747(3) 154(4) 1_665

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_z_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1828850'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2018-03-11 deposited with the CCDC.	2019-07-09 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 N2 O2, 2(H2 O2)'
_chemical_formula_sum            'C4 H10 N2 O6'
_chemical_formula_weight         182.14

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.654(3)
_cell_length_b                   5.802(3)
_cell_length_c                   6.648(3)
_cell_angle_alpha                76.505(8)
_cell_angle_beta                 66.440(7)
_cell_angle_gamma                79.984(8)
_cell_volume                     193.57(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    991
_cell_measurement_theta_min      3.400
_cell_measurement_theta_max      29.260

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             96
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9639
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      230(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            1848
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         26.99
_reflns_number_total             850
_reflns_number_gt                698
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.0259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         850
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5166(3) 0.7895(2) 0.2514(2) 0.0659(4) Uani 1 1 d . . .
N1 N 0.3065(2) 0.3542(2) 0.0669(2) 0.0453(4) Uani 1 1 d . . .
H1 H 0.191(5) 0.270(4) 0.103(3) 0.066(5) Uiso 1 1 d . . .
C1 C 0.5138(3) 0.6572(3) 0.1302(2) 0.0435(4) Uani 1 1 d . . .
C2 C 0.2922(3) 0.5065(3) 0.2149(3) 0.0464(4) Uani 1 1 d . . .
H21 H 0.281(4) 0.416(3) 0.365(3) 0.059(5) Uiso 1 1 d . . .
H22 H 0.139(4) 0.613(4) 0.241(3) 0.064(5) Uiso 1 1 d . . .
O2 O 0.1170(4) 0.9524(5) 0.6117(5) 0.0619(10) Uani 0.576(6) 1 d P . .
O3 O 0.2126(6) 0.8599(5) 0.7862(4) 0.0613(10) Uani 0.576(6) 1 d P . .
O4 O 0.2400(6) 0.7722(6) 0.6744(6) 0.0545(12) Uani 0.424(6) 1 d P . .
O5 O 0.1042(6) 0.9913(9) 0.7368(9) 0.0702(13) Uani 0.424(6) 1 d P . .
H2 H 0.267(7) 0.846(5) 0.521(5) 0.102(8) Uiso 1 1 d . . .
H3 H 0.245(6) 1.007(6) 0.784(5) 0.102(8) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2416(17) . ?
N1 C1 1.306(2) 2_665 ?
N1 C2 1.4390(18) . ?
N1 H1 0.81(3) . ?
C1 C2 1.497(2) . ?
C2 H21 1.000(19) . ?
C2 H22 0.95(2) . ?
O2 O3 1.426(5) . ?
O2 H2 1.02(3) . ?
O3 H3 0.90(3) . ?
O4 O5 1.424(6) . ?
O4 H2 0.97(3) . ?
O5 H3 0.99(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
C1 N1 C2 126.42(12) 2_665 . ?
C1 N1 H1 114.5(14) 2_665 . ?
C2 N1 H1 119.0(14) . . ?
O1 C1 N1 123.01(13) . 2_665 ?
O1 C1 C2 117.94(13) . . ?
N1 C1 C2 119.04(12) 2_665 . ?
N1 C2 C1 114.51(12) . . ?
N1 C2 H21 112.6(10) . . ?
C1 C2 H21 106.9(11) . . ?
N1 C2 H22 110.4(11) . . ?
C1 C2 H22 106.5(12) . . ?
H21 C2 H22 105.3(16) . . ?
O3 O2 H2 85.0(17) . . ?
O2 O3 H3 90(2) . . ?
O5 O4 H2 87.6(18) . . ?
O4 O5 H3 87.3(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C2 C1 -2.1(3) 2_665 . . . ?
O1 C1 C2 N1 -178.59(13) . . . . ?
N1 C1 C2 N1 2.0(2) 2_665 . . . ?
H2 O2 O3 H3 118(3) . . . . ?
H2 O4 O5 H3 -114(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 1.02(3) 1.85(3) 2.779(3) 150(3) .
O4 H2 O1 0.97(3) 1.85(3) 2.602(4) 133(3) .
O3 H3 O1 0.90(3) 1.86(3) 2.662(3) 148(3) 2_676
O5 H3 O1 0.99(3) 1.86(3) 2.711(4) 143(3) 2_676
N1 H1 O2 0.81(3) 2.30(2) 3.013(3) 147.5(19) 2_566
N1 H1 O3 0.81(3) 2.30(3) 3.085(3) 162.2(19) 2_566
N1 H1 O4 0.81(3) 2.31(2) 2.999(3) 143.2(19) 2_566
N1 H1 O5 0.81(3) 2.22(3) 3.015(4) 168.3(19) 2_566

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.043
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1828851'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2018-03-11 deposited with the CCDC.	2019-07-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H10 N2 O2, H2 O2'
_chemical_formula_sum            'C6 H12 N2 O4'
_chemical_formula_weight         176.18

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

loop_
_symmetry_equiv_pos_as_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                   8.2527(13)
_cell_length_b                   6.6341(10)
_cell_length_c                   15.034(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.847(2)
_cell_angle_gamma                90.00
_cell_volume                     811.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3885
_cell_measurement_theta_min      2.644
_cell_measurement_theta_max      30.460

_exptl_crystal_description       nugget
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9705
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         .
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7903
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         27.99
_reflns_number_total             1955
_reflns_number_gt                1740
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0642P)²+0.1056P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1955
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.42668(10) 0.19595(12) 0.77294(6) 0.0209(2) Uani 1 1 d . . .
N2 N 0.72875(10) 0.23574(13) 0.88723(6) 0.0213(2) Uani 1 1 d . . .
O3 O 0.29931(8) 0.13071(12) 0.89186(5) 0.0267(2) Uani 1 1 d . . .
O4 O 0.85776(9) 0.30184(13) 0.76954(5) 0.0292(2) Uani 1 1 d . . .
C1 C 0.28091(13) 0.15240(18) 0.70573(7) 0.0281(2) Uani 1 1 d . . .
C2 C 0.88280(12) 0.23505(18) 0.95188(7) 0.0277(2) Uani 1 1 d . . .
C3 C 0.42406(11) 0.18114(14) 0.86106(7) 0.0201(2) Uani 1 1 d . . .
C4 C 0.72933(12) 0.27132(15) 0.80036(7) 0.0209(2) Uani 1 1 d . . .
C5 C 0.56689(12) 0.27331(16) 0.73657(7) 0.0223(2) Uani 1 1 d . . .
C6 C 0.57917(12) 0.23014(16) 0.92607(7) 0.0226(2) Uani 1 1 d . . .
H11 H 0.1876(17) 0.130(2) 0.7356(10) 0.040(4) Uiso 1 1 d . . .
H12 H 0.3017(16) 0.034(2) 0.6704(9) 0.039(4) Uiso 1 1 d . . .
H13 H 0.2568(17) 0.270(2) 0.6651(10) 0.039(4) Uiso 1 1 d . . .
H21 H 0.8825(18) 0.127(2) 0.9949(10) 0.046(4) Uiso 1 1 d . . .
H22 H 0.9699(18) 0.216(2) 0.9207(10) 0.043(4) Uiso 1 1 d . . .
H23 H 0.8954(18) 0.361(3) 0.9835(10) 0.047(4) Uiso 1 1 d . . .
H51 H 0.5812(16) 0.191(2) 0.6863(10) 0.031(3) Uiso 1 1 d . . .
H52 H 0.5446(15) 0.410(2) 0.7164(8) 0.030(3) Uiso 1 1 d . . .
H61 H 0.5900(16) 0.125(2) 0.9725(9) 0.035(3) Uiso 1 1 d . . .
H62 H 0.5612(15) 0.360(2) 0.9507(9) 0.031(3) Uiso 1 1 d . . .
O1 O 0.91726(9) 0.21935(14) 0.60465(6) 0.0335(2) Uani 1 1 d . . .
O2 O 0.75230(10) 0.20346(14) 0.55042(6) 0.0348(2) Uani 1 1 d . . .
H1 H 0.8900(18) 0.254(2) 0.6559(11) 0.047(4) Uiso 1 1 d . . .
H2 H 0.7675(17) 0.262(2) 0.5008(11) 0.042(4) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.3323(13) . ?
N1 C5 1.4552(12) . ?
N1 C1 1.4615(12) . ?
N2 C4 1.3280(13) . ?
N2 C6 1.4535(12) . ?
N2 C2 1.4622(12) . ?
O3 C3 1.2447(11) . ?
O4 C4 1.2437(12) . ?
C1 H11 0.967(15) . ?
C1 H12 0.980(15) . ?
C1 H13 0.989(15) . ?
C2 H21 0.966(16) . ?
C2 H22 0.931(15) . ?
C2 H23 0.956(17) . ?
C3 C6 1.5072(13) . ?
C4 C5 1.5090(13) . ?
C5 H51 0.956(14) . ?
C5 H52 0.966(14) . ?
C6 H61 0.979(14) . ?
C6 H62 0.958(14) . ?
O1 O2 1.4661(11) . ?
O1 H1 0.870(16) . ?
O2 H2 0.869(16) . ?

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
C3 N1 C5 123.29(8) . . ?
C3 N1 C1 121.43(8) . . ?
C5 N1 C1 115.04(8) . . ?
C4 N2 C6 123.08(8) . . ?
C4 N2 C2 120.35(8) . . ?
C6 N2 C2 115.75(8) . . ?
N1 C1 H11 109.6(9) . . ?
N1 C1 H12 109.5(8) . . ?
H11 C1 H12 110.8(12) . . ?
N1 C1 H13 109.0(9) . . ?
H11 C1 H13 108.5(12) . . ?
H12 C1 H13 109.4(11) . . ?
N2 C2 H21 110.3(9) . . ?
N2 C2 H22 108.9(9) . . ?
H21 C2 H22 109.1(13) . . ?
N2 C2 H23 109.6(9) . . ?
H21 C2 H23 108.9(13) . . ?
H22 C2 H23 110.0(13) . . ?
O3 C3 N1 123.02(9) . . ?
O3 C3 C6 118.79(9) . . ?
N1 C3 C6 118.19(8) . . ?
O4 C4 N2 122.81(9) . . ?
O4 C4 C5 118.87(9) . . ?
N2 C4 C5 118.31(8) . . ?
N1 C5 C4 115.80(8) . . ?
N1 C5 H51 108.1(8) . . ?
C4 C5 H51 106.3(8) . . ?
N1 C5 H52 109.2(7) . . ?
C4 C5 H52 108.0(7) . . ?
H51 C5 H52 109.3(11) . . ?
N2 C6 C3 115.50(8) . . ?
N2 C6 H61 108.9(8) . . ?
C3 C6 H61 105.9(8) . . ?
N2 C6 H62 109.3(8) . . ?
C3 C6 H62 105.9(8) . . ?
H61 C6 H62 111.4(12) . . ?
O2 O1 H1 99.0(10) . . ?
O1 O2 H2 100.8(10) . . ?

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
H1 O1 O2 H2 136.8(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.870(16) 1.802(16) 2.6649(11) 171.4(15) .
O2 H2 O3 0.869(16) 1.845(16) 2.7128(12) 175.9(15) 4_665

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.045
