# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shr27
_database_code_depnum_ccdc_archive 'CCDC 1440221'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;
_audit_creation_date             2015-08-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H2 N8 O8'
_chemical_formula_sum            'C4 H2 N8 O8'
_chemical_formula_weight         290.14
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.7252(7)
_cell_length_b                   8.3018(6)
_cell_length_c                   11.0809(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.203(3)
_cell_angle_gamma                90
_cell_volume                     947.44(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.703
_cell_measurement_theta_min      3.112
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0573 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.9583.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.034
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23787
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.759
_diffrn_reflns_theta_min         3.112
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2052
_reflns_number_total             2453
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²+0.4615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0743
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.95556(8) 0.24092(10) 0.61607(8) 0.01297(19) Uani 1 1 d . . . . .
O2 O 0.64607(9) 0.73438(10) 0.30060(8) 0.01305(19) Uani 1 1 d . . . . .
O3 O 1.00101(8) 0.50815(11) 0.63328(8) 0.01312(19) Uani 1 1 d . . . . .
O4 O 0.52396(9) 0.36847(11) 0.43277(8) 0.01432(19) Uani 1 1 d . . . . .
O5 O 0.44567(9) 0.13077(11) 0.36996(9) 0.0169(2) Uani 1 1 d . . . . .
O6 O 0.65055(9) 0.47291(11) 0.24264(8) 0.0155(2) Uani 1 1 d . . . . .
O7 O 0.76107(8) 0.58319(11) 0.71077(8) 0.01425(19) Uani 1 1 d . . . . .
O8 O 0.87245(9) 0.78269(12) 0.81682(8) 0.0182(2) Uani 1 1 d . . . . .
N1 N 0.92146(10) 0.40448(12) 0.58442(9) 0.0104(2) Uani 1 1 d . . . . .
N2 N 0.85305(10) 0.14625(13) 0.55134(10) 0.0127(2) Uani 1 1 d . . . . .
N3 N 0.68346(10) 0.57015(12) 0.32825(9) 0.0108(2) Uani 1 1 d . . . . .
N4 N 0.69332(10) 0.82150(13) 0.40950(10) 0.0126(2) Uani 1 1 d . . . . .
N5 N 0.65572(10) 0.17336(13) 0.40286(10) 0.0115(2) Uani 1 1 d . . . . .
H5 H 0.6567(15) 0.069(2) 0.3997(15) 0.017(4) Uiso 1 1 d . . . . .
N6 N 0.53324(10) 0.22914(13) 0.40392(9) 0.0111(2) Uani 1 1 d . . . . .
N7 N 0.82748(11) 0.78385(14) 0.61044(10) 0.0126(2) Uani 1 1 d . . . . .
H7 H 0.8378(17) 0.886(2) 0.6179(16) 0.024(4) Uiso 1 1 d . . . . .
N8 N 0.81835(10) 0.71140(13) 0.72042(10) 0.0122(2) Uani 1 1 d . . . . .
C1 C 0.76501(11) 0.24376(15) 0.48368(11) 0.0102(2) Uani 1 1 d . . . . .
C2 C 0.80432(11) 0.40812(15) 0.50194(11) 0.0100(2) Uani 1 1 d . . . . .
C3 C 0.75066(11) 0.56079(15) 0.44904(11) 0.0101(2) Uani 1 1 d . . . . .
C4 C 0.75642(11) 0.72107(15) 0.49556(11) 0.0106(2) 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
O1 N1 1.4244(13) . ?
O1 N2 1.3787(13) . ?
O2 N3 1.4301(13) . ?
O2 N4 1.3765(13) . ?
O3 N1 1.2264(13) . ?
O4 N6 1.2115(14) . ?
O5 N6 1.2220(14) . ?
O6 N3 1.2203(13) . ?
O7 N8 1.2187(14) . ?
O8 N8 1.2173(14) . ?
N1 C2 1.3318(15) . ?
N2 C1 1.3091(16) . ?
N3 C3 1.3337(15) . ?
N4 C4 1.3048(16) . ?
N5 H5 0.870(18) . ?
N5 N6 1.3960(14) . ?
N5 C1 1.3899(15) . ?
N7 H7 0.854(19) . ?
N7 N8 1.3867(15) . ?
N7 C4 1.3898(15) . ?
C1 C2 1.4258(17) . ?
C2 C3 1.4467(17) . ?
C3 C4 1.4221(17) . ?

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
N2 O1 N1 107.61(8) . . ?
N4 O2 N3 107.49(8) . . ?
O3 N1 O1 117.46(9) . . ?
O3 N1 C2 133.93(11) . . ?
C2 N1 O1 108.59(9) . . ?
C1 N2 O1 106.77(10) . . ?
O6 N3 O2 117.46(9) . . ?
O6 N3 C3 134.40(11) . . ?
C3 N3 O2 108.13(9) . . ?
C4 N4 O2 107.10(10) . . ?
N6 N5 H5 110.7(11) . . ?
C1 N5 H5 115.4(11) . . ?
C1 N5 N6 118.78(10) . . ?
O4 N6 O5 127.35(11) . . ?
O4 N6 N5 117.75(10) . . ?
O5 N6 N5 114.83(10) . . ?
N8 N7 H7 112.5(11) . . ?
N8 N7 C4 119.15(10) . . ?
C4 N7 H7 118.9(11) . . ?
O7 N8 N7 117.34(10) . . ?
O8 N8 O7 127.36(11) . . ?
O8 N8 N7 115.28(11) . . ?
N2 C1 N5 116.93(11) . . ?
N2 C1 C2 111.90(11) . . ?
N5 C1 C2 131.05(11) . . ?
N1 C2 C1 105.11(10) . . ?
N1 C2 C3 119.36(11) . . ?
C1 C2 C3 135.44(11) . . ?
N3 C3 C2 120.01(11) . . ?
N3 C3 C4 105.42(10) . . ?
C4 C3 C2 134.49(11) . . ?
N4 C4 N7 118.02(11) . . ?
N4 C4 C3 111.82(11) . . ?
N7 C4 C3 129.80(11) . . ?

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
N5 H5 N4 0.870(18) 2.086(18) 2.9469(15) 169.9(15) 1_545

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C2 C1 0.68(12) . . . . ?
O1 N1 C2 C3 -176.34(9) . . . . ?
O1 N2 C1 N5 175.47(10) . . . . ?
O1 N2 C1 C2 -0.90(13) . . . . ?
O2 N3 C3 C2 -178.10(10) . . . . ?
O2 N3 C3 C4 -0.91(12) . . . . ?
O2 N4 C4 N7 172.00(10) . . . . ?
O2 N4 C4 C3 -1.89(14) . . . . ?
O3 N1 C2 C1 179.27(12) . . . . ?
O3 N1 C2 C3 2.2(2) . . . . ?
O6 N3 C3 C2 1.5(2) . . . . ?
O6 N3 C3 C4 178.68(13) . . . . ?
N1 O1 N2 C1 1.29(12) . . . . ?
N1 C2 C3 N3 141.05(12) . . . . ?
N1 C2 C3 C4 -35.2(2) . . . . ?
N2 O1 N1 O3 179.90(9) . . . . ?
N2 O1 N1 C2 -1.25(12) . . . . ?
N2 C1 C2 N1 0.13(14) . . . . ?
N2 C1 C2 C3 176.44(13) . . . . ?
N3 O2 N4 C4 1.26(12) . . . . ?
N3 C3 C4 N4 1.80(14) . . . . ?
N3 C3 C4 N7 -171.18(12) . . . . ?
N4 O2 N3 O6 -179.83(10) . . . . ?
N4 O2 N3 C3 -0.15(12) . . . . ?
N5 C1 C2 N1 -175.58(12) . . . . ?
N5 C1 C2 C3 0.7(2) . . . . ?
N6 N5 C1 N2 130.96(12) . . . . ?
N6 N5 C1 C2 -53.51(18) . . . . ?
N8 N7 C4 N4 134.59(12) . . . . ?
N8 N7 C4 C3 -52.79(18) . . . . ?
C1 N5 N6 O4 28.89(16) . . . . ?
C1 N5 N6 O5 -153.97(11) . . . . ?
C1 C2 C3 N3 -34.9(2) . . . . ?
C1 C2 C3 C4 148.94(14) . . . . ?
C2 C3 C4 N4 178.39(13) . . . . ?
C2 C3 C4 N7 5.4(2) . . . . ?
C4 N7 N8 O7 9.22(16) . . . . ?
C4 N7 N8 O8 -172.68(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shrv345
_database_code_depnum_ccdc_archive 'CCDC 1440222'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 N8 O8, 2(H4 N)'
_chemical_formula_sum            'C4 H8 N10 O8'
_chemical_formula_weight         324.20

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7692(7)
_cell_length_b                   7.3210(10)
_cell_length_c                   8.4065(10)
_cell_angle_alpha                64.804(4)
_cell_angle_beta                 87.429(4)
_cell_angle_gamma                67.479(4)
_cell_volume                     293.79(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2296
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      30.79

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_F_000             166
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.093
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.7072
_exptl_absorpt_correction_T_max  0.7461

_diffrn_ambient_temperature      296(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 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3483
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  0.0116
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.249
_diffrn_reflns_theta_max         30.788
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             1612
_reflns_number_gt                1480
_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 APEX2 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_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)+(0.0532P)²+0.0634P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1612
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.33942(16) 0.29293(14) 1.01489(10) 0.0340(2) Uani 1 1 d . . . . .
O2 O 0.19105(16) 0.15425(13) 0.88129(10) 0.03065(19) Uani 1 1 d . . . . .
N3 N 0.31875(15) 0.26023(13) 0.88139(10) 0.02242(18) Uani 1 1 d . . . . .
N4 N 0.43069(16) 0.34290(15) 0.74723(11) 0.02578(19) Uani 1 1 d . . . . .
C5 C 0.35869(17) 0.32889(15) 0.59936(12) 0.02070(19) Uani 1 1 d . . . . .
N6 N 0.52898(15) 0.23104(13) 0.51881(11) 0.02361(19) Uani 1 1 d . . . . .
O7 O 0.76307(14) 0.13156(14) 0.54419(12) 0.0361(2) Uani 1 1 d . . . . .
O8 O 0.39809(14) 0.26431(12) 0.36085(10) 0.02767(18) Uani 1 1 d . . . . .
N9 N 0.14664(16) 0.38988(15) 0.34910(12) 0.0268(2) Uani 1 1 d . . . . .
C10 C 0.12239(16) 0.43057(15) 0.48766(12) 0.02137(19) Uani 1 1 d . . . . .
N1S N 0.1438(2) 0.78149(18) 0.85783(15) 0.0329(2) Uani 1 1 d . . . . .
H1S H 0.035(3) 0.809(3) 0.924(2) 0.039 Uiso 1 1 d . U . . .
H2S H 0.200(3) 0.636(3) 0.891(2) 0.039 Uiso 1 1 d . U . . .
H3S H 0.266(3) 0.811(3) 0.881(2) 0.039 Uiso 1 1 d . U . . .
H4S H 0.092(3) 0.841(3) 0.742(2) 0.039 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.2623(11) . ?
O2 N3 1.2583(11) . ?
N3 N4 1.3070(12) . ?
N4 C5 1.3841(12) . ?
C5 N6 1.3233(12) . ?
C5 C10 1.4271(12) . ?
N6 O7 1.2410(11) . ?
N6 O8 1.4375(11) . ?
O8 N9 1.3687(11) . ?
N9 C10 1.3092(12) . ?
C10 C10 1.4575(17) 2_566 ?
N1S H1S 0.841(18) . ?
N1S H2S 0.899(17) . ?
N1S H3S 0.862(18) . ?
N1S H4S 0.888(18) . ?

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
O2 N3 O1 119.63(8) . . ?
O2 N3 N4 123.08(8) . . ?
O1 N3 N4 117.28(9) . . ?
N3 N4 C5 111.53(8) . . ?
N6 C5 N4 121.21(9) . . ?
N6 C5 C10 105.69(8) . . ?
N4 C5 C10 132.44(9) . . ?
O7 N6 C5 135.57(9) . . ?
O7 N6 O8 116.56(8) . . ?
C5 N6 O8 107.78(7) . . ?
N9 O8 N6 108.04(7) . . ?
C10 N9 O8 106.71(8) . . ?
N9 C10 C5 111.74(8) . . ?
N9 C10 C10 120.97(10) . 2_566 ?
C5 C10 C10 127.27(10) . 2_566 ?
H1S N1S H2S 105.7(15) . . ?
H1S N1S H3S 107.0(16) . . ?
H2S N1S H3S 109.4(15) . . ?
H1S N1S H4S 118.0(17) . . ?
H2S N1S H4S 103.5(14) . . ?
H3S N1S H4S 112.7(15) . . ?

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
O2 N3 N4 C5 9.31(13) . . . . ?
O1 N3 N4 C5 -169.68(8) . . . . ?
N3 N4 C5 N6 -124.86(10) . . . . ?
N3 N4 C5 C10 65.93(13) . . . . ?
N4 C5 N6 O7 2.46(17) . . . . ?
C10 C5 N6 O7 174.21(11) . . . . ?
N4 C5 N6 O8 -173.91(8) . . . . ?
C10 C5 N6 O8 -2.16(10) . . . . ?
O7 N6 O8 N9 -175.55(8) . . . . ?
C5 N6 O8 N9 1.61(10) . . . . ?
N6 O8 N9 C10 -0.26(10) . . . . ?
O8 N9 C10 C5 -1.11(11) . . . . ?
O8 N9 C10 C10 177.45(11) . . . 2_566 ?
N6 C5 C10 N9 2.14(11) . . . . ?
N4 C5 C10 N9 172.56(10) . . . . ?
N6 C5 C10 C10 -176.32(12) . . . 2_566 ?
N4 C5 C10 C10 -5.9(2) . . . 2_566 ?

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
N1S H1S O1 0.841(18) 2.508(17) 3.1005(14) 128.3(14) 2_567
N1S H1S O2 0.841(18) 2.092(18) 2.9266(13) 171.6(17) 2_567
N1S H1S N3 0.841(18) 2.625(18) 3.3985(14) 153.5(14) 2_567
N1S H2S O1 0.899(17) 2.083(17) 2.9716(14) 169.6(14) .
N1S H2S N3 0.899(17) 2.605(17) 3.4705(14) 161.8(13) .
N1S H3S O1 0.862(18) 2.194(18) 2.9793(14) 151.4(15) 2_667
N1S H3S O2 0.862(18) 2.386(17) 2.9315(13) 121.6(14) 1_565
N1S H4S O7 0.888(18) 2.251(17) 2.9662(14) 137.4(14) 1_465
N1S H4S O7 0.888(18) 2.465(18) 3.2223(15) 143.4(14) 2_666

_refine_diff_density_max         0.369
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.048


# start Validation Reply Form
_vrf_PLAT015_shrv345             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
