# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shrv324
_database_code_depnum_ccdc_archive 'CCDC 1419916'
_audit_update_record             
;
2015-08-21 deposited with the CCDC.
2015-10-13 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         '(H4 N1 O1 +1), (C4 H6 N8 O5 1-), H2 O1'
_chemical_formula_sum            'C4 H8 N8 O6'
_chemical_formula_weight         264.18

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'

_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                   26.968(2)
_cell_length_b                   4.0185(3)
_cell_length_c                   18.7676(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.579(5)
_cell_angle_gamma                90
_cell_volume                     2005.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.161
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6713
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_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            9159
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.532
_diffrn_reflns_theta_max         26.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2031
_reflns_number_gt                1208
_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 v2010.3-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0845P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2031
_refine_ls_number_parameters     181
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1598
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.003
_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
N1 N 0.37753(10) 0.0723(7) 0.44977(14) 0.0320(7) Uani 1 1 d . . . . .
N2 N 0.38531(10) 0.0725(7) 0.52521(14) 0.0337(7) Uani 1 1 d . . . . .
C3 C 0.42430(12) -0.1148(8) 0.54530(17) 0.0292(7) Uani 1 1 d . . . . .
O4 O 0.44391(8) -0.2391(6) 0.48865(11) 0.0302(6) Uani 1 1 d . . . . .
C5 C 0.41208(11) -0.1113(8) 0.43067(16) 0.0255(7) Uani 1 1 d . . . . .
C6 C 0.41998(11) -0.1949(8) 0.35833(17) 0.0274(7) Uani 1 1 d . . . . .
N7 N 0.45621(10) -0.3888(7) 0.34654(14) 0.0344(7) Uani 1 1 d . . . . .
O8 O 0.45175(9) -0.4080(6) 0.27265(13) 0.0417(6) Uani 1 1 d . . . . .
N9 N 0.41172(10) -0.2144(7) 0.23756(15) 0.0354(7) Uani 1 1 d . . . . .
C10 C 0.39150(11) -0.0838(8) 0.29035(16) 0.0260(7) Uani 1 1 d . . . . .
N11 N 0.44627(11) -0.1884(8) 0.61106(16) 0.0466(9) Uani 1 1 d . . . . .
H11A H 0.4348 -0.1083 0.6476 0.056 Uiso 1 1 calc R U . . .
H11B H 0.4722 -0.3166 0.6177 0.056 Uiso 1 1 calc R U . . .
N12 N 0.35053(9) 0.1208(7) 0.28971(13) 0.0286(6) Uani 1 1 d . . . . .
N13 N 0.32639(10) 0.2106(7) 0.22591(14) 0.0285(6) Uani 1 1 d . . . . .
O14 O 0.28833(8) 0.3924(6) 0.22614(13) 0.0392(6) Uani 1 1 d . . . . .
O15 O 0.33972(9) 0.1271(6) 0.16811(12) 0.0405(6) Uani 1 1 d . . . . .
O1S O 0.28248(10) 0.6398(6) 0.42100(15) 0.0451(7) Uani 1 1 d . . . . .
H1S H 0.2910(14) 0.563(10) 0.471(2) 0.054 Uiso 1 1 d . U . . .
N2S N 0.27698(10) 0.3514(7) 0.37862(16) 0.0314(7) Uani 1 1 d D . . . .
H2SA H 0.3049(6) 0.234(6) 0.3836(18) 0.038 Uiso 1 1 d D U . . .
H2SB H 0.2486(6) 0.256(7) 0.3846(18) 0.038 Uiso 1 1 d D U . . .
H2SC H 0.2670(12) 0.422(8) 0.3341(6) 0.038 Uiso 1 1 d D U . . .
O3S O 0.30332(8) 0.5711(6) 0.05571(12) 0.0334(6) Uani 1 1 d D . . . .
H3SA H 0.3316(5) 0.663(7) 0.065(2) 0.040 Uiso 1 1 d D U . . .
H3SB H 0.3166(12) 0.450(6) 0.0901(11) 0.040 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.285(4) . ?
N1 N2 1.396(4) . ?
N2 C3 1.297(4) . ?
C3 N11 1.311(4) . ?
C3 O4 1.359(4) . ?
O4 C5 1.369(4) . ?
C5 C6 1.448(4) . ?
C6 N7 1.297(4) . ?
C6 C10 1.446(4) . ?
N7 O8 1.374(3) . ?
O8 N9 1.403(3) . ?
N9 C10 1.317(4) . ?
C10 N12 1.375(4) . ?
N11 H11A 0.8600 . ?
N11 H11B 0.8600 . ?
N12 N13 1.315(3) . ?
N13 O15 1.244(3) . ?
N13 O14 1.260(3) . ?
O1S N2S 1.400(4) . ?
O1S H1S 0.98(4) . ?
N2S H2SA 0.8800(11) . ?
N2S H2SB 0.8801(11) . ?
N2S H2SC 0.8801(11) . ?
O3S H3SA 0.8402(11) . ?
O3S H3SB 0.8402(11) . ?

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
C5 N1 N2 106.8(2) . . ?
C3 N2 N1 105.8(2) . . ?
N2 C3 N11 128.5(3) . . ?
N2 C3 O4 112.8(3) . . ?
N11 C3 O4 118.7(3) . . ?
C3 O4 C5 102.1(2) . . ?
N1 C5 O4 112.4(3) . . ?
N1 C5 C6 128.4(3) . . ?
O4 C5 C6 119.2(3) . . ?
N7 C6 C10 109.9(3) . . ?
N7 C6 C5 122.1(3) . . ?
C10 C6 C5 128.0(3) . . ?
C6 N7 O8 105.3(2) . . ?
N7 O8 N9 112.0(2) . . ?
C10 N9 O8 104.5(2) . . ?
N9 C10 N12 131.6(3) . . ?
N9 C10 C6 108.4(3) . . ?
N12 C10 C6 120.0(3) . . ?
C3 N11 H11A 120.0 . . ?
C3 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
N13 N12 C10 116.6(3) . . ?
O15 N13 O14 120.9(2) . . ?
O15 N13 N12 123.3(3) . . ?
O14 N13 N12 115.9(3) . . ?
N2S O1S H1S 106(2) . . ?
O1S N2S H2SA 112(2) . . ?
O1S N2S H2SB 107(2) . . ?
H2SA N2S H2SB 120(3) . . ?
O1S N2S H2SC 105(2) . . ?
H2SA N2S H2SC 113(3) . . ?
H2SB N2S H2SC 97(3) . . ?
H3SA O3S H3SB 81(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
C5 N1 N2 C3 -0.2(4) . . . . ?
N1 N2 C3 N11 179.4(4) . . . . ?
N1 N2 C3 O4 0.7(4) . . . . ?
N2 C3 O4 C5 -0.9(3) . . . . ?
N11 C3 O4 C5 -179.7(3) . . . . ?
N2 N1 C5 O4 -0.3(4) . . . . ?
N2 N1 C5 C6 179.0(3) . . . . ?
C3 O4 C5 N1 0.7(4) . . . . ?
C3 O4 C5 C6 -178.7(3) . . . . ?
N1 C5 C6 N7 -178.9(3) . . . . ?
O4 C5 C6 N7 0.3(5) . . . . ?
N1 C5 C6 C10 1.8(6) . . . . ?
O4 C5 C6 C10 -179.0(3) . . . . ?
C10 C6 N7 O8 -0.4(4) . . . . ?
C5 C6 N7 O8 -179.8(3) . . . . ?
C6 N7 O8 N9 1.0(3) . . . . ?
N7 O8 N9 C10 -1.2(3) . . . . ?
O8 N9 C10 N12 -178.2(3) . . . . ?
O8 N9 C10 C6 0.9(3) . . . . ?
N7 C6 C10 N9 -0.3(4) . . . . ?
C5 C6 C10 N9 179.0(3) . . . . ?
N7 C6 C10 N12 178.9(3) . . . . ?
C5 C6 C10 N12 -1.8(5) . . . . ?
N9 C10 N12 N13 -0.7(5) . . . . ?
C6 C10 N12 N13 -179.8(3) . . . . ?
C10 N12 N13 O15 -2.0(4) . . . . ?
C10 N12 N13 O14 178.6(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
N11 H11A N9 0.86 2.30 3.140(4) 167.2 6_556
N11 H11B N7 0.86 2.27 3.121(4) 170.3 5_646
O1S H1S O3S 0.98(4) 1.65(5) 2.637(3) 178(4) 6_566
N2S H2SA N1 0.8800(11) 2.234(17) 3.031(4) 150(3) .
N2S H2SB O3S 0.8801(11) 2.071(15) 2.892(4) 155(3) 4_545
N2S H2SC O14 0.8801(11) 2.20(2) 2.933(4) 140(3) .
O3S H3SA N2 0.8402(11) 2.04(2) 2.773(3) 146(3) 6_565
O3S H3SB O15 0.8402(11) 1.977(5) 2.812(3) 172(3) .

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.073

