# 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 2018

####################################################################### 
# 
# 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_dm16632_0m
_database_code_depnum_ccdc_archive 'CCDC 1524793'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2018-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H12 N6 O6'
_chemical_formula_weight         288.24

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.9409(13)
_cell_length_b                   5.1266(10)
_cell_length_c                   16.585(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.805(3)
_cell_angle_gamma                90
_cell_volume                     583.18(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    1270
_cell_measurement_theta_min      4.971
_cell_measurement_theta_max      54.569

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5855
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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            3646
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.485
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1082
_reflns_number_gt                792
_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)+(0.0530P)²+0.0167P] 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     SHELXL
_refine_ls_extinction_coef       0.018(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1082
_refine_ls_number_parameters     105
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.010
_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 0.4312(3) 0.9013(4) 0.10533(11) 0.0214(5) Uani 1 1 d . . . . .
N2 N 0.3506(2) 0.7262(3) 0.04801(11) 0.0214(5) Uani 1 1 d . . . . .
N3 N 0.6803(2) 0.6938(3) 0.07061(11) 0.0196(5) Uani 1 1 d . . . . .
O1 O 0.6855(2) 0.7197(3) 0.27810(10) 0.0338(5) Uani 1 1 d . . . . .
O2 O 0.9047(2) 1.0338(3) 0.31653(9) 0.0281(4) Uani 1 1 d . . . . .
H2 H 0.9166 0.9556 0.3615 0.042 Uiso 1 1 calc R U . . .
O3 O 0.9548(2) 0.7508(3) 0.45107(10) 0.0288(4) Uani 1 1 d D . . . .
C1 C 0.5072(3) 0.6052(4) 0.02974(13) 0.0180(5) Uani 1 1 d . . . . .
C2 C 0.6251(3) 0.8783(4) 0.11836(13) 0.0196(5) Uani 1 1 d . . . . .
C3 C 0.7569(3) 1.0328(4) 0.17968(13) 0.0222(5) Uani 1 1 d . . . . .
H3A H 0.7046 1.2118 0.1821 0.027 Uiso 1 1 calc R U . . .
H3B H 0.8870 1.0452 0.1625 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7769(3) 0.9107(4) 0.26313(13) 0.0221(5) Uani 1 1 d . . . . .
H1 H 0.364(3) 1.001(4) 0.1298(14) 0.022(6) Uiso 1 1 d . . . . .
H3C H 0.886(7) 0.797(10) 0.487(3) 0.18(2) Uiso 1 1 d D . . . .
H3D H 1.067(3) 0.773(6) 0.479(2) 0.080(12) Uiso 1 1 d 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 C2 1.335(3) . ?
N1 N2 1.364(2) . ?
N1 H1 0.84(2) . ?
N2 C1 1.326(3) . ?
N3 C2 1.327(3) . ?
N3 C1 1.363(2) . ?
O1 C4 1.213(3) . ?
O2 C4 1.315(2) . ?
O2 H2 0.8400 . ?
O3 H3C 0.85(2) . ?
O3 H3D 0.852(18) . ?
C1 C1 1.455(4) 3_665 ?
C2 C3 1.488(3) . ?
C3 C4 1.506(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?

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
C2 N1 N2 110.53(18) . . ?
C2 N1 H1 126.8(15) . . ?
N2 N1 H1 122.6(15) . . ?
C1 N2 N1 101.77(16) . . ?
C2 N3 C1 102.78(16) . . ?
C4 O2 H2 109.5 . . ?
H3C O3 H3D 98(4) . . ?
N2 C1 N3 114.90(18) . . ?
N2 C1 C1 121.9(2) . 3_665 ?
N3 C1 C1 123.2(2) . 3_665 ?
N3 C2 N1 110.00(18) . . ?
N3 C2 C3 125.72(18) . . ?
N1 C2 C3 124.3(2) . . ?
C2 C3 C4 111.58(17) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
O1 C4 O2 124.7(2) . . ?
O1 C4 C3 123.09(19) . . ?
O2 C4 C3 112.17(18) . . ?

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 N1 N2 C1 0.0(2) . . . . ?
N1 N2 C1 N3 -0.8(2) . . . . ?
N1 N2 C1 C1 179.4(2) . . . 3_665 ?
C2 N3 C1 N2 1.3(2) . . . . ?
C2 N3 C1 C1 -178.9(2) . . . 3_665 ?
C1 N3 C2 N1 -1.2(2) . . . . ?
C1 N3 C2 C3 176.91(19) . . . . ?
N2 N1 C2 N3 0.8(2) . . . . ?
N2 N1 C2 C3 -177.35(18) . . . . ?
N3 C2 C3 C4 -93.2(2) . . . . ?
N1 C2 C3 C4 84.6(2) . . . . ?
C2 C3 C4 O1 -4.5(3) . . . . ?
C2 C3 C4 O2 175.06(18) . . . . ?

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
O3 H3D N2 0.852(18) 2.118(19) 2.966(2) 173(3) 4_676
O3 H3C N3 0.85(2) 2.14(3) 2.966(2) 164(5) 4_576
N1 H1 O1 0.84(2) 1.97(3) 2.745(2) 154(2) 2_655
C3 H3B O3 0.99 2.55 3.360(3) 139.0 2_755
O2 H2 O3 0.84 1.80 2.639(2) 172.2 .
O3 H3D N2 0.852(18) 2.118(19) 2.966(2) 173(3) 4_676
O3 H3C N3 0.85(2) 2.14(3) 2.966(2) 164(5) 4_576
N1 H1 O1 0.84(2) 1.97(3) 2.745(2) 154(2) 2_655
C3 H3B O3 0.99 2.55 3.360(3) 139.0 2_755
O2 H2 O3 0.84 1.80 2.639(2) 172.2 .

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_dm16640_0m
_database_code_depnum_ccdc_archive 'CCDC 1524802'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2018-01-17 downloaded from the CCDC.
;
_audit_creation_date             2016-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H2 N12 O12, 2(H2 O)'
_chemical_formula_sum            'C6 H6 N12 O14'
_chemical_formula_weight         470.23
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   11.8413(13)
_cell_length_b                   10.4440(11)
_cell_length_c                   13.8220(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.458(2)
_cell_angle_gamma                90
_cell_volume                     1708.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2576
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0418 before and 0.0357 after correction.
The Ratio of minimum to maximum transmission is 0.9298.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8561
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.740
_diffrn_reflns_theta_min         2.601
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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                2087
_reflns_number_total             2652
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2652
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.015
_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)+(0.0489P)²+0.7942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0953
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_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 0.64587(9) 0.42607(10) 0.19835(7) 0.0312(2) Uani 1 1 d . . . . .
O2 O 0.80386(9) 0.33027(10) 0.16679(7) 0.0340(2) Uani 1 1 d . . . . .
O3 O 0.91888(8) 0.41935(10) 0.36003(9) 0.0392(3) Uani 1 1 d . . . . .
O4 O 0.91266(9) 0.21208(10) 0.34394(8) 0.0372(3) Uani 1 1 d . . . . .
O5 O 0.70565(9) 0.14530(9) 0.41650(7) 0.0303(2) Uani 1 1 d . . . . .
O6 O 0.64459(10) 0.14939(10) 0.26685(7) 0.0356(2) Uani 1 1 d . . . . .
N1 N 0.58085(8) 0.38328(9) 0.42812(7) 0.0179(2) Uani 1 1 d . . . . .
N2 N 0.62843(8) 0.58230(10) 0.46115(7) 0.0193(2) Uani 1 1 d . . . . .
H2 H 0.6265(16) 0.6630(19) 0.4836(14) 0.041(5) Uiso 1 1 d . . . . .
N3 N 0.71344(9) 0.53715(9) 0.40808(7) 0.0198(2) Uani 1 1 d . . . . .
N4 N 0.73036(9) 0.36604(10) 0.21983(7) 0.0212(2) Uani 1 1 d . . . . .
N5 N 0.87123(9) 0.31827(10) 0.34736(8) 0.0239(2) Uani 1 1 d . . . . .
N6 N 0.69327(9) 0.19420(10) 0.33733(7) 0.0217(2) Uani 1 1 d . . . . .
C1 C 0.55111(9) 0.49076(11) 0.47274(8) 0.0170(2) Uani 1 1 d . . . . .
C2 C 0.68076(9) 0.41778(10) 0.39086(8) 0.0161(2) Uani 1 1 d . . . . .
C3 C 0.74331(10) 0.32818(10) 0.32780(8) 0.0168(2) Uani 1 1 d . . . . .
O7 O 0.90607(9) 0.68773(9) 0.46379(8) 0.0293(2) Uani 1 1 d . . . . .
H7A H 0.8610(19) 0.630(2) 0.4383(15) 0.055(6) Uiso 1 1 d . . . . .
H7B H 0.959(2) 0.702(2) 0.4325(19) 0.076(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 N4 1.2112(14) . ?
O2 N4 1.2112(14) . ?
O3 N5 1.2077(15) . ?
O4 N5 1.2141(14) . ?
O5 N6 1.2132(14) . ?
O6 N6 1.2131(14) . ?
N1 C1 1.3324(14) . ?
N1 C2 1.3512(14) . ?
N2 H2 0.90(2) . ?
N2 N3 1.3458(14) . ?
N2 C1 1.3362(15) . ?
N3 C2 1.3252(14) . ?
N4 C3 1.5476(15) . ?
N5 C3 1.5354(16) . ?
N6 C3 1.5265(15) . ?
C1 C1 1.455(2) 5_666 ?
C2 C3 1.4889(15) . ?
O7 H7A 0.87(2) . ?
O7 H7B 0.79(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 101.30(9) . . ?
N3 N2 H2 122.9(13) . . ?
C1 N2 H2 127.3(12) . . ?
C1 N2 N3 109.81(9) . . ?
C2 N3 N2 102.03(9) . . ?
O1 N4 C3 115.45(9) . . ?
O2 N4 O1 127.80(11) . . ?
O2 N4 C3 116.73(10) . . ?
O3 N5 O4 128.05(12) . . ?
O3 N5 C3 114.95(10) . . ?
O4 N5 C3 116.91(10) . . ?
O5 N6 O6 127.29(11) . . ?
O5 N6 C3 115.18(10) . . ?
O6 N6 C3 117.51(10) . . ?
N1 C1 N2 110.94(10) . . ?
N1 C1 C1 125.78(13) . 5_666 ?
N2 C1 C1 123.28(13) . 5_666 ?
N1 C2 C3 120.60(10) . . ?
N3 C2 N1 115.91(10) . . ?
N3 C2 C3 123.31(10) . . ?
N5 C3 N4 105.08(9) . . ?
N6 C3 N4 106.75(8) . . ?
N6 C3 N5 107.84(9) . . ?
C2 C3 N4 111.43(9) . . ?
C2 C3 N5 116.27(9) . . ?
C2 C3 N6 109.00(9) . . ?
H7A O7 H7B 113(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
N2 H2 O7 0.90(2) 1.77(2) 2.6520(14) 167.8(19) 7_666
O7 H7A N3 0.87(2) 2.03(2) 2.8600(15) 158(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 N4 C3 N5 -152.21(10) . . . . ?
O1 N4 C3 N6 93.43(12) . . . . ?
O1 N4 C3 C2 -25.48(14) . . . . ?
O2 N4 C3 N5 29.30(13) . . . . ?
O2 N4 C3 N6 -85.06(12) . . . . ?
O2 N4 C3 C2 156.03(11) . . . . ?
O3 N5 C3 N4 79.55(12) . . . . ?
O3 N5 C3 N6 -166.85(11) . . . . ?
O3 N5 C3 C2 -44.15(15) . . . . ?
O4 N5 C3 N4 -97.24(12) . . . . ?
O4 N5 C3 N6 16.36(14) . . . . ?
O4 N5 C3 C2 139.07(11) . . . . ?
O5 N6 C3 N4 173.78(10) . . . . ?
O5 N6 C3 N5 61.30(12) . . . . ?
O5 N6 C3 C2 -65.75(13) . . . . ?
O6 N6 C3 N4 -7.38(14) . . . . ?
O6 N6 C3 N5 -119.86(11) . . . . ?
O6 N6 C3 C2 113.09(12) . . . . ?
N1 C2 C3 N4 103.24(12) . . . . ?
N1 C2 C3 N5 -136.41(11) . . . . ?
N1 C2 C3 N6 -14.32(14) . . . . ?
N2 N3 C2 N1 0.54(13) . . . . ?
N2 N3 C2 C3 175.54(10) . . . . ?
N3 N2 C1 N1 -0.37(13) . . . . ?
N3 N2 C1 C1 179.67(13) . . . 5_666 ?
N3 C2 C3 N4 -71.53(14) . . . . ?
N3 C2 C3 N5 48.82(15) . . . . ?
N3 C2 C3 N6 170.91(10) . . . . ?
C1 N1 C2 N3 -0.75(13) . . . . ?
C1 N1 C2 C3 -175.89(10) . . . . ?
C1 N2 N3 C2 -0.10(12) . . . . ?
C2 N1 C1 N2 0.64(12) . . . . ?
C2 N1 C1 C1 -179.40(14) . . . 5_666 ?

_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_dm16641
_database_code_depnum_ccdc_archive 'CCDC 1524803'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2018-01-17 downloaded from the CCDC.
;
_audit_creation_date             2016-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 N8 O6'
_chemical_formula_sum            'C3 N8 O6'
_chemical_formula_weight         244.11
_chemical_absolute_configuration rmad
_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'
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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.7188(10)
_cell_length_b                   16.867(2)
_cell_length_c                   6.4384(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     838.24(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2320
_cell_measurement_temperature    130
_cell_measurement_theta_max      29.00
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0504 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.9386.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8443
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.475
_diffrn_reflns_theta_min         2.415
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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         0.704
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2172
_reflns_number_total             2549
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 807 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.023
_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)+(0.0366P)²+0.0940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0776
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     dual
_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 0.1863(2) 0.53972(9) 0.8606(2) 0.0286(4) Uani 1 1 d . . . . .
O2 O 0.1924(2) 0.50210(9) 0.5365(3) 0.0294(3) Uani 1 1 d . . . . .
O3 O 0.5074(2) 0.58935(9) 0.3794(2) 0.0261(3) Uani 1 1 d . . . . .
O4 O 0.2691(3) 0.63941(11) 0.2560(2) 0.0365(4) Uani 1 1 d . . . . .
O5 O 0.0047(2) 0.66337(10) 0.6525(3) 0.0333(4) Uani 1 1 d . . . . .
O6 O 0.1890(2) 0.75442(9) 0.5566(2) 0.0295(4) Uani 1 1 d . . . . .
N1 N 0.5552(2) 0.60074(11) 0.8292(3) 0.0204(3) Uani 1 1 d . . . . .
N2 N 0.4477(2) 0.72585(10) 0.8513(3) 0.0218(4) Uani 1 1 d . . . . .
N3 N 0.5855(2) 0.72371(11) 0.9783(3) 0.0244(4) Uani 1 1 d . . . . .
N4 N 0.7816(2) 0.62117(10) 1.0697(3) 0.0211(4) Uani 1 1 d . . . . .
N5 N 0.8906(2) 0.59811(12) 1.1602(3) 0.0293(4) Uani 1 1 d . . . . .
N6 N 0.2190(2) 0.54839(10) 0.6772(3) 0.0201(3) Uani 1 1 d . . . . .
N7 N 0.3646(2) 0.61895(10) 0.3947(3) 0.0209(3) Uani 1 1 d . . . . .
N8 N 0.1483(2) 0.68791(10) 0.6092(3) 0.0223(4) Uani 1 1 d . . . . .
C1 C 0.6415(3) 0.64946(12) 0.9559(3) 0.0194(4) Uani 1 1 d . . . . .
C2 C 0.4352(3) 0.65244(12) 0.7685(3) 0.0166(4) Uani 1 1 d . . . . .
C3 C 0.2979(2) 0.62882(11) 0.6187(3) 0.0168(3) 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 N6 1.216(2) . ?
O2 N6 1.213(2) . ?
O3 N7 1.215(2) . ?
O4 N7 1.208(2) . ?
O5 N8 1.215(2) . ?
O6 N8 1.213(2) . ?
N1 C1 1.336(3) . ?
N1 C2 1.331(3) . ?
N2 N3 1.342(3) . ?
N2 C2 1.352(3) . ?
N3 C1 1.333(3) . ?
N4 N5 1.095(2) . ?
N4 C1 1.390(3) . ?
N6 C3 1.534(2) . ?
N7 C3 1.540(3) . ?
N8 C3 1.527(2) . ?
C2 C3 1.488(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
C2 N1 C1 97.07(17) . . ?
N3 N2 C2 105.79(17) . . ?
C1 N3 N2 102.49(17) . . ?
N5 N4 C1 179.1(2) . . ?
O1 N6 C3 115.28(16) . . ?
O2 N6 O1 127.74(18) . . ?
O2 N6 C3 116.95(16) . . ?
O3 N7 C3 115.07(16) . . ?
O4 N7 O3 127.69(19) . . ?
O4 N7 C3 117.22(17) . . ?
O5 N8 C3 117.29(17) . . ?
O6 N8 O5 127.97(18) . . ?
O6 N8 C3 114.74(16) . . ?
N1 C1 N4 119.88(19) . . ?
N3 C1 N1 118.85(19) . . ?
N3 C1 N4 121.18(19) . . ?
N1 C2 N2 115.79(18) . . ?
N1 C2 C3 120.72(18) . . ?
N2 C2 C3 123.49(18) . . ?
N6 C3 N7 105.47(14) . . ?
N8 C3 N6 106.66(14) . . ?
N8 C3 N7 106.61(15) . . ?
C2 C3 N6 111.13(15) . . ?
C2 C3 N7 113.46(16) . . ?
C2 C3 N8 112.97(16) . . ?

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 N6 C3 N7 167.67(16) . . . . ?
O1 N6 C3 N8 -79.2(2) . . . . ?
O1 N6 C3 C2 44.3(2) . . . . ?
O2 N6 C3 N7 -14.2(2) . . . . ?
O2 N6 C3 N8 98.90(19) . . . . ?
O2 N6 C3 C2 -137.57(18) . . . . ?
O3 N7 C3 N6 -83.68(19) . . . . ?
O3 N7 C3 N8 163.18(16) . . . . ?
O3 N7 C3 C2 38.2(2) . . . . ?
O4 N7 C3 N6 94.7(2) . . . . ?
O4 N7 C3 N8 -18.5(2) . . . . ?
O4 N7 C3 C2 -143.46(19) . . . . ?
O5 N8 C3 N6 2.0(2) . . . . ?
O5 N8 C3 N7 114.35(19) . . . . ?
O5 N8 C3 C2 -120.4(2) . . . . ?
O6 N8 C3 N6 -177.34(16) . . . . ?
O6 N8 C3 N7 -65.0(2) . . . . ?
O6 N8 C3 C2 60.3(2) . . . . ?
N1 C2 C3 N6 45.8(2) . . . . ?
N1 C2 C3 N7 -72.9(2) . . . . ?
N1 C2 C3 N8 165.62(18) . . . . ?
N2 N3 C1 N1 -0.8(3) . . . . ?
N2 N3 C1 N4 -177.40(18) . . . . ?
N2 C2 C3 N6 -134.25(19) . . . . ?
N2 C2 C3 N7 107.1(2) . . . . ?
N2 C2 C3 N8 -14.4(3) . . . . ?
N3 N2 C2 N1 -0.4(2) . . . . ?
N3 N2 C2 C3 179.63(18) . . . . ?
C1 N1 C2 N2 -0.1(2) . . . . ?
C1 N1 C2 C3 179.92(18) . . . . ?
C2 N1 C1 N3 0.5(2) . . . . ?
C2 N1 C1 N4 177.19(19) . . . . ?
C2 N2 N3 C1 0.6(2) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
