# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_mo_d8v18858_0m
_database_code_depnum_ccdc_archive 'CCDC 1877493'
loop_
_audit_author_name
_audit_author_address
'Yupeng Cao'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2018-11-07 deposited with the CCDC.	2019-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        DNAMBO
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H10 N10 O6'
_chemical_formula_weight         306.23

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                   11.0337(7)
_cell_length_b                   11.2495(6)
_cell_length_c                   9.7684(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.107(2)
_cell_angle_gamma                90
_cell_volume                     1170.59(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7836
_cell_measurement_theta_min      5.267
_cell_measurement_theta_max      54.932

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.155
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6680
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10651
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.633
_diffrn_reflns_theta_max         25.980
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1134
_reflns_number_gt                1061
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0389P)²+0.6628P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.027(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1134
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
N1 N 0.09908(10) 0.60566(9) 0.36991(11) 0.0347(3) Uani 1 1 d . . . . .
N2 N 0.16258(10) 0.43107(8) 0.47861(10) 0.0280(3) Uani 1 1 d . . . . .
N3 N 0.30659(10) 0.52648(9) 0.68604(11) 0.0321(3) Uani 1 1 d . . . . .
N4 N 0.35177(10) 0.42451(9) 0.75054(11) 0.0299(3) Uani 1 1 d . . . . .
N6 N 0.58420(12) 0.29466(10) 0.09105(13) 0.0357(3) Uani 1 1 d . . . . .
O1 O 0.19089(9) 0.62566(7) 0.50011(9) 0.0373(3) Uani 1 1 d . . . . .
O2 O 0.33032(9) 0.32553(8) 0.69550(10) 0.0405(3) Uani 1 1 d . . . . .
O3 O 0.42038(10) 0.43813(9) 0.87299(10) 0.0428(3) Uani 1 1 d . . . . .
C1 C 0.08748(10) 0.49063(10) 0.36578(12) 0.0249(3) Uani 1 1 d . . . . .
C2 C 0.22319(10) 0.51773(10) 0.55741(12) 0.0261(3) Uani 1 1 d . . . . .
C3 C 0.0000 0.42240(15) 0.2500 0.0289(4) Uani 1 2 d S T P . .
H3 H 0.0516(15) 0.3721(14) 0.2077(16) 0.041(4) Uiso 1 1 d . . . . .
H6A H 0.530(2) 0.3369(19) 0.021(2) 0.075(6) Uiso 1 1 d . . . . .
H6B H 0.6203(19) 0.345(2) 0.159(2) 0.070(6) Uiso 1 1 d . . . . .
H6C H 0.5324(19) 0.238(2) 0.127(2) 0.074(6) Uiso 1 1 d . . . . .
H6D H 0.631(2) 0.244(2) 0.068(2) 0.091(8) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0372(6) 0.0264(6) 0.0312(6) -0.0015(4) -0.0078(4) 0.0004(4)
N2 0.0313(5) 0.0233(5) 0.0248(5) 0.0003(4) -0.0009(4) -0.0012(4)
N3 0.0357(6) 0.0254(6) 0.0286(6) -0.0034(4) -0.0033(4) 0.0016(4)
N4 0.0282(5) 0.0298(6) 0.0279(5) -0.0031(4) 0.0003(4) 0.0018(4)
N6 0.0409(7) 0.0254(6) 0.0368(7) -0.0025(5) 0.0029(5) 0.0001(5)
O1 0.0432(5) 0.0224(5) 0.0352(5) -0.0025(3) -0.0095(4) 0.0001(4)
O2 0.0450(6) 0.0256(5) 0.0415(6) -0.0045(4) -0.0053(4) 0.0039(4)
O3 0.0466(6) 0.0420(6) 0.0286(5) -0.0025(4) -0.0105(4) 0.0058(4)
C1 0.0253(6) 0.0234(6) 0.0240(6) -0.0001(4) 0.0030(4) 0.0010(4)
C2 0.0271(6) 0.0227(6) 0.0267(6) -0.0015(4) 0.0038(5) 0.0013(4)
C3 0.0315(9) 0.0228(8) 0.0272(9) 0.000 -0.0016(7) 0.000

_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 C1 1.3000(15) . ?
N1 O1 1.4223(13) . ?
N2 C2 1.3122(15) . ?
N2 C1 1.3690(15) . ?
N3 N4 1.3407(14) . ?
N3 C2 1.3537(15) . ?
N4 O2 1.2323(13) . ?
N4 O3 1.2471(14) . ?
N6 H6A 0.92(2) . ?
N6 H6B 0.88(2) . ?
N6 H6C 0.99(2) . ?
N6 H6D 0.84(3) . ?
O1 C2 1.3455(14) . ?
C1 C3 1.4936(14) . ?
C3 C1 1.4936(14) 2 ?
C3 H3 0.968(15) . ?

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 O1 103.09(9) . . ?
C2 N2 C1 102.57(9) . . ?
N4 N3 C2 116.97(10) . . ?
O2 N4 O3 121.94(10) . . ?
O2 N4 N3 124.22(10) . . ?
O3 N4 N3 113.83(10) . . ?
H6A N6 H6B 107.7(19) . . ?
H6A N6 H6C 106.1(16) . . ?
H6B N6 H6C 109.9(16) . . ?
H6A N6 H6D 119(2) . . ?
H6B N6 H6D 117(2) . . ?
H6C N6 H6D 96(2) . . ?
C2 O1 N1 106.20(9) . . ?
N1 C1 N2 115.35(10) . . ?
N1 C1 C3 125.03(11) . . ?
N2 C1 C3 119.62(10) . . ?
N2 C2 O1 112.77(10) . . ?
N2 C2 N3 135.87(11) . . ?
O1 C2 N3 111.27(10) . . ?
C1 C3 C1 118.15(14) . 2 ?
C1 C3 H3 106.7(9) . . ?
C1 C3 H3 108.2(9) 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
C2 N3 N4 O2 6.27(18) . . . . ?
C2 N3 N4 O3 -174.72(11) . . . . ?
C1 N1 O1 C2 0.33(13) . . . . ?
O1 N1 C1 N2 -0.63(14) . . . . ?
O1 N1 C1 C3 179.09(9) . . . . ?
C2 N2 C1 N1 0.66(14) . . . . ?
C2 N2 C1 C3 -179.07(9) . . . . ?
C1 N2 C2 O1 -0.40(13) . . . . ?
C1 N2 C2 N3 175.83(14) . . . . ?
N1 O1 C2 N2 0.06(14) . . . . ?
N1 O1 C2 N3 -177.12(9) . . . . ?
N4 N3 C2 N2 7.5(2) . . . . ?
N4 N3 C2 O1 -176.21(10) . . . . ?
N1 C1 C3 C1 -4.30(9) . . . 2 ?
N2 C1 C3 C1 175.41(11) . . . 2 ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-4

_shelx_res_file                  
; 
TITL mo_d8v18858_0m_a.res in C2/c 
CELL 0.71073 11.0337 11.2495 9.7684 90 105.107 90 
ZERR 4 0.0007 0.0006 0.0006 0 0.002 0 
LATT 7 
SYMM -X,+Y,0.5-Z 
SFAC C  H  N  O 
UNIT 20 40 40 24 
OMIT  -3.00  52.00 
L.S. 9 
ACTA 
BOND $H 
FMAP 2 
PLAN 20 
LIST 4 
htab 
conf 
mpla 
wpdb -1 
size 0.18 0.15 0.12 
TEMP 23 
WGHT    0.038900    0.662800 
EXTI    0.026824 
FVAR       1.25693 
N1    3    0.099080    0.605664    0.369908    11.00000    0.03720    0.02641 = 
         0.03121   -0.00145   -0.00777    0.00044 
N2    3    0.162579    0.431070    0.478607    11.00000    0.03131    0.02329 = 
         0.02483    0.00025   -0.00090   -0.00124 
N3    3    0.306591    0.526478    0.686041    11.00000    0.03572    0.02537 = 
         0.02857   -0.00344   -0.00330    0.00155 
N4    3    0.351766    0.424512    0.750543    11.00000    0.02816    0.02983 = 
         0.02788   -0.00306    0.00028    0.00182 
N6    3    0.584200    0.294659    0.091054    11.00000    0.04093    0.02541 = 
         0.03680   -0.00254    0.00287    0.00007 
O1    4    0.190888    0.625656    0.500113    11.00000    0.04321    0.02237 = 
         0.03517   -0.00246   -0.00950    0.00005 
O2    4    0.330325    0.325533    0.695500    11.00000    0.04502    0.02557 = 
         0.04150   -0.00448   -0.00530    0.00387 
O3    4    0.420376    0.438130    0.872990    11.00000    0.04656    0.04199 = 
         0.02859   -0.00245   -0.01050    0.00581 
C1    1    0.087476    0.490631    0.365784    11.00000    0.02525    0.02339 = 
         0.02404   -0.00012    0.00297    0.00102 
C2    1    0.223192    0.517729    0.557410    11.00000    0.02713    0.02274 = 
         0.02672   -0.00149    0.00375    0.00126 
C3    1    0.000000    0.422399    0.250000    10.50000    0.03153    0.02282 = 
         0.02715    0.00000   -0.00160    0.00000 
H3    2    0.051555    0.372141    0.207704    11.00000    0.04113 
H6A   2    0.529710    0.336863    0.021106    11.00000    0.07491 
H6B   2    0.620312    0.345258    0.158723    11.00000    0.06951 
H6C   2    0.532400    0.237521    0.127487    11.00000    0.07407 
H6D   2    0.630788    0.243744    0.067915    11.00000    0.09056 
HKLF 4 
  
REM  mo_d8v18858_0m_a.res in C2/c 
REM R1 =  0.0295 for    1061 Fo > 4sig(Fo)  and  0.0317 for all    1134 data 
REM    117 parameters refined using      0 restraints 
  
END 
  
WGHT      0.0389      0.6660 
  
REM Instructions for potential hydrogen bonds 
EQIV $1 -x+1/2, -y+1/2, -z+1 
HTAB C3 O2_$1 
EQIV $2 x, y, z-1 
HTAB N6 O3_$2 
EQIV $3 -x+1, -y+1, -z+1 
HTAB N6 N3_$3 
HTAB N6 O3_$3 
EQIV $4 -x+1/2, y-1/2, -z+1/2 
HTAB N6 N1_$4 
EQIV $5 x+1/2, -y+1/2, z-1/2 
HTAB N6 N2_$5 
HTAB N6 O2_$5 
  
REM Highest difference peak  0.237,  deepest hole -0.177,  1-sigma level  0.033 
Q1    1   0.0459  0.4606  0.3066  11.00000  0.05    0.24 
Q2    1   0.0605  0.5559  0.3940  11.00000  0.05    0.16 
Q3    1   0.1186  0.5480  0.3418  11.00000  0.05    0.15 
Q4    1   0.2775  0.5119  0.6140  11.00000  0.05    0.15 
Q5    1   0.1451  0.3701  0.5004  11.00000  0.05    0.14 
Q6    1   0.0000  0.3610  0.2500  10.50000  0.05    0.14 
Q7    1   0.1768  0.5779  0.5457  11.00000  0.05    0.13 
Q8    1   0.3057  0.5873  0.7286  11.00000  0.05    0.13 
Q9    1   0.1346  0.4539  0.4106  11.00000  0.05    0.12 
Q10   1   0.2215  0.4684  0.5076  11.00000  0.05    0.11 
Q11   1   0.1460  0.6239  0.4249  11.00000  0.05    0.11 
Q12   1   0.4404  0.3665  0.8881  11.00000  0.05    0.11 
Q13   1   0.3255  0.4879  0.7050  11.00000  0.05    0.11 
Q14   1   0.2396  0.5722  0.5009  11.00000  0.05    0.10 
Q15   1   0.0668  0.6565  0.3123  11.00000  0.05    0.10 
Q16   1   0.4228  0.5350  0.9043  11.00000  0.05    0.09 
Q17   1   0.2960  0.3492  0.7496  11.00000  0.05    0.08 
Q18   1   0.2224  0.6706  0.5349  11.00000  0.05    0.07 
Q19   1   0.3787  0.2593  0.7537  11.00000  0.05    0.07 
Q20   1   0.3586  0.3957  0.9495  11.00000  0.05    0.07 
;
_shelx_res_checksum              82595
