# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
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data_mo_dm16032_0m
_database_code_depnum_ccdc_archive 'CCDC 1476973'
_audit_update_record             
;
2016-04-28 deposited with the CCDC.
2016-06-17 downloaded from the CCDC.
;
_audit_creation_date             2016-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C3 N8 O3, 2(H4 N O)'
_chemical_formula_sum            'C3 H8 N10 O5'
_chemical_formula_weight         264.19
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1300(12)
_cell_length_b                   8.1314(14)
_cell_length_c                   9.0571(15)
_cell_angle_alpha                83.381(3)
_cell_angle_beta                 71.653(3)
_cell_angle_gamma                72.486(3)
_cell_volume                     475.18(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2286
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0450 before and 0.0257 after correction.
The Ratio of minimum to maximum transmission is 0.8949.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4859
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.611
_diffrn_reflns_theta_min         2.370
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2472
_reflns_number_total             2893
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²+0.0736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1034
_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 -0.37079(13) -0.05443(10) 0.60940(9) 0.01818(18) Uani 1 1 d . . . . .
O2 O -0.49444(13) -0.49797(11) 0.76442(9) 0.01882(18) Uani 1 1 d . . . . .
O3 O -0.35467(13) -0.72406(10) 0.61676(10) 0.01819(18) Uani 1 1 d . . . . .
N1 N -0.41190(15) -0.21237(12) 0.65752(11) 0.01644(19) Uani 1 1 d . . . . .
N2 N -0.23199(15) -0.06350(12) 0.46403(11) 0.01675(19) Uani 1 1 d . . . . .
N3 N 0.04805(14) -0.17062(12) 0.16816(11) 0.01586(19) Uani 1 1 d . . . . .
N4 N 0.16534(15) -0.26723(12) 0.04383(11) 0.0169(2) Uani 1 1 d . . . . .
N5 N 0.13928(15) -0.42249(13) 0.06825(11) 0.0174(2) Uani 1 1 d . . . . .
N6 N 0.00474(15) -0.43170(12) 0.20881(11) 0.01657(19) Uani 1 1 d . . . . .
N7 N -0.27697(14) -0.48677(12) 0.52140(11) 0.01498(19) Uani 1 1 d . . . . .
N8 N -0.37934(14) -0.56594(12) 0.63814(11) 0.01409(18) Uani 1 1 d . . . . .
C1 C -0.29953(16) -0.31562(14) 0.54099(12) 0.0139(2) Uani 1 1 d . . . . .
C2 C -0.18811(16) -0.22059(14) 0.41946(12) 0.0140(2) Uani 1 1 d . . . . .
C3 C -0.04785(16) -0.27534(13) 0.26716(12) 0.0136(2) Uani 1 1 d . . . . .
O4 O 0.46174(15) 0.13032(11) -0.12039(10) 0.02103(19) Uani 1 1 d . . . . .
H4 H 0.516(3) 0.183(3) -0.202(2) 0.042(5) Uiso 1 1 d . . . . .
N9 N 0.41749(16) 0.23769(13) 0.00494(11) 0.0169(2) Uani 1 1 d . . . . .
H9A H 0.535(3) 0.240(2) 0.020(2) 0.029(4) Uiso 1 1 d . . . . .
H9B H 0.342(3) 0.190(3) 0.090(3) 0.046(5) Uiso 1 1 d . . . . .
H9C H 0.344(3) 0.344(2) -0.0092(19) 0.023(4) Uiso 1 1 d . . . . .
O5 O 0.06936(13) 0.14008(11) 0.21361(11) 0.0218(2) Uani 1 1 d . . . . .
H5 H 0.044(3) 0.053(3) 0.209(2) 0.037(5) Uiso 1 1 d . . . . .
N10 N -0.12674(15) 0.25280(12) 0.27691(12) 0.01545(19) Uani 1 1 d . . . . .
H10A H -0.207(2) 0.258(2) 0.2198(19) 0.023(4) Uiso 1 1 d . . . . .
H10B H -0.109(3) 0.358(2) 0.274(2) 0.028(4) Uiso 1 1 d . . . . .
H10C H -0.182(3) 0.220(2) 0.372(2) 0.035(5) 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 N1 1.3936(13) . ?
O1 N2 1.3698(12) . ?
O2 N8 1.2525(12) . ?
O3 N8 1.2734(12) . ?
N1 C1 1.3145(14) . ?
N2 C2 1.3004(14) . ?
N3 N4 1.3417(13) . ?
N3 C3 1.3361(14) . ?
N4 N5 1.3146(14) . ?
N5 N6 1.3412(13) . ?
N6 C3 1.3340(14) . ?
N7 N8 1.3058(13) . ?
N7 C1 1.3779(14) . ?
C1 C2 1.4362(15) . ?
C2 C3 1.4513(15) . ?
O4 H4 0.86(2) . ?
O4 N9 1.4098(12) . ?
N9 H9A 0.893(18) . ?
N9 H9B 0.91(2) . ?
N9 H9C 0.887(17) . ?
O5 H5 0.79(2) . ?
O5 N10 1.4032(12) . ?
N10 H10A 0.874(17) . ?
N10 H10B 0.896(18) . ?
N10 H10C 0.87(2) . ?

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 111.40(8) . . ?
C1 N1 O1 104.84(9) . . ?
C2 N2 O1 105.96(9) . . ?
C3 N3 N4 104.79(9) . . ?
N5 N4 N3 109.25(9) . . ?
N4 N5 N6 109.71(9) . . ?
C3 N6 N5 104.60(9) . . ?
N8 N7 C1 116.52(9) . . ?
O2 N8 O3 120.03(9) . . ?
O2 N8 N7 124.94(10) . . ?
O3 N8 N7 115.03(9) . . ?
N1 C1 N7 131.36(10) . . ?
N1 C1 C2 108.72(9) . . ?
N7 C1 C2 119.92(9) . . ?
N2 C2 C1 109.06(9) . . ?
N2 C2 C3 121.04(10) . . ?
C1 C2 C3 129.90(10) . . ?
N3 C3 C2 122.35(10) . . ?
N6 C3 N3 111.66(9) . . ?
N6 C3 C2 125.98(10) . . ?
N9 O4 H4 106.0(13) . . ?
O4 N9 H9A 109.6(11) . . ?
O4 N9 H9B 106.0(13) . . ?
O4 N9 H9C 112.8(11) . . ?
H9A N9 H9B 110.2(17) . . ?
H9A N9 H9C 109.8(15) . . ?
H9B N9 H9C 108.4(16) . . ?
N10 O5 H5 102.6(14) . . ?
O5 N10 H10A 110.9(11) . . ?
O5 N10 H10B 106.4(11) . . ?
O5 N10 H10C 110.4(12) . . ?
H10A N10 H10B 107.3(15) . . ?
H10A N10 H10C 110.0(16) . . ?
H10B N10 H10C 111.8(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
O4 H4 O3 0.86(2) 1.81(2) 2.6654(12) 174.7(19) 1_664
N9 H9B O5 0.91(2) 2.05(2) 2.8723(14) 150.1(18) .
N9 H9C N5 0.887(17) 2.052(17) 2.8722(15) 153.2(15) 1_565
O5 H5 N3 0.79(2) 1.89(2) 2.6619(14) 167(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
O1 N1 C1 N7 -179.87(11) . . . . ?
O1 N1 C1 C2 -0.10(12) . . . . ?
O1 N2 C2 C1 -0.98(12) . . . . ?
O1 N2 C2 C3 178.41(9) . . . . ?
N1 O1 N2 C2 0.95(12) . . . . ?
N1 C1 C2 N2 0.71(13) . . . . ?
N1 C1 C2 C3 -178.60(11) . . . . ?
N2 O1 N1 C1 -0.51(12) . . . . ?
N2 C2 C3 N3 2.42(17) . . . . ?
N2 C2 C3 N6 -178.71(10) . . . . ?
N3 N4 N5 N6 -0.04(12) . . . . ?
N4 N3 C3 N6 -0.27(12) . . . . ?
N4 N3 C3 C2 178.75(10) . . . . ?
N4 N5 N6 C3 -0.12(12) . . . . ?
N5 N6 C3 N3 0.24(12) . . . . ?
N5 N6 C3 C2 -178.73(10) . . . . ?
N7 C1 C2 N2 -179.50(10) . . . . ?
N7 C1 C2 C3 1.19(17) . . . . ?
N8 N7 C1 N1 -1.79(18) . . . . ?
N8 N7 C1 C2 178.47(9) . . . . ?
C1 N7 N8 O2 -0.04(16) . . . . ?
C1 N7 N8 O3 -179.72(9) . . . . ?
C1 C2 C3 N3 -178.34(10) . . . . ?
C1 C2 C3 N6 0.53(19) . . . . ?
C3 N3 N4 N5 0.18(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
