# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1839449'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H8 N5 O2.50'
_chemical_formula_weight         202.18

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                   20.6228(16)
_cell_length_b                   4.8896(3)
_cell_length_c                   17.0577(13)
_cell_angle_alpha                90
_cell_angle_beta                 113.615(3)
_cell_angle_gamma                90
_cell_volume                     1576.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2521
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.36

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.032
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    0.134
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6483
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7553
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.634
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1603
_reflns_number_gt                1100
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0438P)²+1.5392P] 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         1603
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.38874(8) 0.8259(3) 0.15227(10) 0.0208(4) Uani 1 1 d . . . . .
O2 O 0.34129(8) 1.0124(3) 0.23697(10) 0.0167(4) Uani 1 1 d . . . . .
N3 N 0.09253(10) 1.3388(4) 0.00444(12) 0.0150(5) Uani 1 1 d . . . . .
N9 N 0.01323(10) 1.2597(4) 0.07706(11) 0.0143(4) Uani 1 1 d . . . . .
N1 N 0.19388(10) 1.0572(4) 0.04815(11) 0.0143(4) Uani 1 1 d . . . . .
N6 N 0.21650(10) 0.7204(4) 0.15291(13) 0.0144(4) Uani 1 1 d . . . . .
N7 N 0.07542(10) 0.9169(4) 0.16027(12) 0.0143(4) Uani 1 1 d . . . . .
C6 C 0.17497(11) 0.9215(4) 0.10655(14) 0.0140(5) Uani 1 1 d . . . . .
C62 C 0.34161(12) 0.8464(4) 0.18068(14) 0.0141(5) Uani 1 1 d . . . . .
C5 C 0.11207(11) 1.0022(4) 0.11284(14) 0.0133(5) Uani 1 1 d . . . . .
C4 C 0.07199(11) 1.2115(4) 0.06209(14) 0.0123(5) Uani 1 1 d . . . . .
C61 C 0.28057(11) 0.6441(5) 0.14296(15) 0.0141(5) Uani 1 1 d . . . . .
H61A H 0.2694 0.6228 0.0812 0.017 Uiso 1 1 calc R U . . .
H61B H 0.2964 0.4638 0.1704 0.017 Uiso 1 1 calc R U . . .
C8 C 0.01779(12) 1.0764(4) 0.13701(14) 0.0149(5) Uani 1 1 d . . . . .
H8 H -0.0165 1.0604 0.1609 0.018 Uiso 1 1 calc R U . . .
C2 C 0.15278(12) 1.2507(5) 0.00077(14) 0.0155(5) Uani 1 1 d . . . . .
H2 H 0.1670 1.3362 -0.0398 0.019 Uiso 1 1 calc R U . . .
H7 H 0.0875(13) 0.783(6) 0.1975(17) 0.026(7) Uiso 1 1 d . . . . .
H3 H 0.0644(15) 1.467(6) -0.0296(18) 0.034(8) Uiso 1 1 d . . . . .
H6 H 0.2047(12) 0.647(5) 0.1919(15) 0.014(6) Uiso 1 1 d . . . . .
O1W O 0.5000 1.1510(5) 0.2500 0.0222(6) Uani 1 2 d S T P . .
H1W H 0.4603(15) 1.041(6) 0.2155(19) 0.052(9) 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 C62 1.252(3) . ?
O2 C62 1.259(3) . ?
N3 C2 1.340(3) . ?
N3 C4 1.366(3) . ?
N9 C8 1.334(3) . ?
N9 C4 1.355(3) . ?
N1 C2 1.311(3) . ?
N1 C6 1.377(3) . ?
N6 C6 1.335(3) . ?
N6 C61 1.447(3) . ?
N7 C8 1.342(3) . ?
N7 C5 1.375(3) . ?
C6 C5 1.400(3) . ?
C62 C61 1.526(3) . ?
C5 C4 1.381(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 N3 C4 116.6(2) . . ?
C8 N9 C4 103.53(18) . . ?
C2 N1 C6 119.57(19) . . ?
C6 N6 C61 121.3(2) . . ?
C8 N7 C5 106.29(19) . . ?
N6 C6 N1 118.9(2) . . ?
N6 C6 C5 123.8(2) . . ?
N1 C6 C5 117.32(19) . . ?
O1 C62 O2 126.1(2) . . ?
O1 C62 C61 114.96(19) . . ?
O2 C62 C61 118.94(19) . . ?
N7 C5 C4 105.16(19) . . ?
N7 C5 C6 134.8(2) . . ?
C4 C5 C6 120.1(2) . . ?
N9 C4 N3 127.9(2) . . ?
N9 C4 C5 111.49(19) . . ?
N3 C4 C5 120.6(2) . . ?
N6 C61 C62 114.92(18) . . ?
N9 C8 N7 113.5(2) . . ?
N1 C2 N3 125.9(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
N7 H7 O2 0.87(3) 1.96(3) 2.743(3) 148(2) 4_545
N7 H7 O1W 0.87(3) 2.40(3) 2.891(2) 116(2) 3_445
N3 H3 N9 0.89(3) 1.99(3) 2.849(3) 161(2) 5_585
N6 H6 O2 0.87(2) 1.93(2) 2.789(3) 168(2) 4_545
O1W H1W O1 0.96(3) 1.78(3) 2.740(2) 178(3) .
O1W H1W O2 0.96(3) 2.63(3) 3.2617(16) 124(2) .

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.066

_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_2
_database_code_depnum_ccdc_archive 'CCDC 1839450'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H11 Cl2 N5 O3'
_chemical_formula_weight         284.11

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'
Cl Cl 0.1484 0.1585 '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                   10.3324(12)
_cell_length_b                   16.4608(18)
_cell_length_c                   6.4735(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.758(4)
_cell_angle_gamma                90
_cell_volume                     1100.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      30.53

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    0.595
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6778
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25540
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.327
_diffrn_reflns_theta_max         30.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3355
_reflns_number_gt                3111
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0377P)²+2.5626P] 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         3355
_refine_ls_number_parameters     180
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_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
Cl1 Cl 0.43449(4) -0.12466(3) 0.76563(7) 0.00921(11) Uani 1 1 d . . . . .
Cl2 Cl 1.13000(4) 0.03225(3) 0.74766(7) 0.01203(11) Uani 1 1 d . . . . .
N9 N 0.50914(16) 0.18738(10) 0.7254(3) 0.0095(3) Uani 1 1 d . . . . .
O2 O 0.92698(15) -0.23084(10) 0.9079(3) 0.0175(3) Uani 1 1 d . . . . .
N1 N 0.83608(16) 0.06162(10) 0.7332(3) 0.0095(3) Uani 1 1 d . . . . .
C61 C 0.84090(18) -0.10895(11) 0.7628(3) 0.0107(3) Uani 1 1 d . . . . .
H61A H 0.9089 -0.0782 0.8385 0.013 Uiso 1 1 calc R U . . .
H61B H 0.8712 -0.1183 0.6203 0.013 Uiso 1 1 calc R U . . .
N6 N 0.72203(15) -0.06146(10) 0.7562(3) 0.0089(3) Uani 1 1 d . . . . .
C6 C 0.72285(17) 0.01839(11) 0.7423(3) 0.0078(3) Uani 1 1 d . . . . .
O1 O 0.71376(15) -0.21582(10) 0.9140(3) 0.0172(3) Uani 1 1 d . . . . .
N3 N 0.74361(16) 0.19346(10) 0.7227(3) 0.0111(3) Uani 1 1 d . . . . .
N7 N 0.48109(15) 0.05580(10) 0.7395(3) 0.0082(3) Uani 1 1 d . . . . .
C5 C 0.61314(17) 0.06992(11) 0.7384(3) 0.0076(3) Uani 1 1 d . . . . .
C4 C 0.63004(17) 0.15326(11) 0.7289(3) 0.0083(3) Uani 1 1 d . . . . .
C62 C 0.8195(2) -0.18997(12) 0.8684(3) 0.0122(4) Uani 1 1 d . . . . .
C2 C 0.84259(19) 0.14420(12) 0.7244(3) 0.0117(3) Uani 1 1 d . . . . .
H2 H 0.9263 0.1679 0.7191 0.014 Uiso 1 1 calc R U . . .
C8 C 0.42162(18) 0.12784(11) 0.7312(3) 0.0097(3) Uani 1 1 d . . . . .
H8 H 0.3305 0.1355 0.7295 0.012 Uiso 1 1 calc R U . . .
O1W O 1.12338(15) -0.15549(10) 0.7700(3) 0.0254(4) Uani 1 1 d D . . . .
H1W2 H 1.141(3) -0.1020(5) 0.768(5) 0.030 Uiso 1 1 d D U . . .
H1W1 H 1.202(4) -0.182(2) 0.771(5) 0.030 Uiso 1 1 d D U . . .
H7 H 0.448(4) 0.006(2) 0.739(6) 0.037(10) Uiso 1 1 d . . . . .
H6 H 0.650(3) -0.085(2) 0.763(5) 0.020(7) Uiso 1 1 d . . . . .
H9 H 0.494(3) 0.238(2) 0.721(5) 0.028(8) Uiso 1 1 d . . . . .
H1 H 0.906(3) 0.041(2) 0.725(5) 0.027(8) Uiso 1 1 d . . . . .
H2A H 1.016(5) -0.194(3) 0.861(7) 0.064(14) 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
N9 C8 1.334(2) . ?
N9 C4 1.370(2) . ?
O2 C62 1.321(2) . ?
N1 C2 1.362(2) . ?
N1 C6 1.371(2) . ?
C61 N6 1.456(2) . ?
C61 C62 1.516(3) . ?
N6 C6 1.318(2) . ?
C6 C5 1.416(2) . ?
O1 C62 1.212(3) . ?
N3 C2 1.305(2) . ?
N3 C4 1.348(2) . ?
N7 C8 1.336(2) . ?
N7 C5 1.384(2) . ?
C5 C4 1.384(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
C8 N9 C4 108.46(16) . . ?
C2 N1 C6 124.21(17) . . ?
N6 C61 C62 110.93(16) . . ?
C6 N6 C61 122.10(16) . . ?
N6 C6 N1 121.79(17) . . ?
N6 C6 C5 126.38(17) . . ?
N1 C6 C5 111.82(16) . . ?
C2 N3 C4 112.15(16) . . ?
C8 N7 C5 107.67(15) . . ?
N7 C5 C4 106.95(16) . . ?
N7 C5 C6 133.50(17) . . ?
C4 C5 C6 119.54(16) . . ?
N3 C4 N9 126.32(17) . . ?
N3 C4 C5 126.73(17) . . ?
N9 C4 C5 106.95(16) . . ?
O1 C62 O2 122.13(19) . . ?
O1 C62 C61 123.79(18) . . ?
O2 C62 C61 114.07(17) . . ?
N3 C2 N1 125.54(18) . . ?
N9 C8 N7 109.96(17) . . ?

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
C61 H61A Cl2 0.99 2.98 3.787(2) 138.9 .
C61 H61A Cl2 0.99 2.82 3.421(2) 119.9 3_757
C61 H61B Cl2 0.99 2.77 3.554(2) 136.4 3_756
C2 H2 O2 0.95 2.40 3.269(2) 151.1 2_756
C8 H8 Cl2 0.95 2.68 3.402(2) 132.9 1_455
O1W H1W2 Cl2 0.900(2) 2.218(9) 3.0945(18) 165(3) .
O1W H1W1 Cl1 0.92(4) 2.58(4) 3.2549(17) 130(3) 1_655
O1W H1W1 N3 0.92(4) 2.13(4) 2.841(2) 134(3) 2_746
N7 H7 Cl1 0.88(4) 2.17(4) 3.0143(17) 161(3) .
N6 H6 Cl1 0.85(3) 2.32(3) 3.1492(17) 168(3) .
N9 H9 Cl1 0.85(4) 2.38(4) 3.1487(17) 151(3) 2_656
N9 H9 O1 0.85(4) 2.43(3) 2.933(2) 119(3) 2_656
N1 H1 Cl2 0.80(4) 2.33(4) 3.0753(17) 157(3) .
O2 H2A O1W 1.15(5) 1.41(5) 2.550(2) 170(4) .

_refine_diff_density_max         1.114
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.103

_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_3
_database_code_depnum_ccdc_archive 'CCDC 1839451'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-07-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H12 N6 O4'
_chemical_formula_weight         268.25

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   4.7539(4)
_cell_length_b                   11.6942(9)
_cell_length_c                   10.3125(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.378(3)
_cell_angle_gamma                90
_cell_volume                     563.92(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6631
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.29

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.031
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7148
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9238
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.658
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2790
_reflns_number_gt                2663
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0418P)²+0.1246P] 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       0.024(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   -0.2(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2790
_refine_ls_number_parameters     198
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
N3 N 0.7541(4) 0.05824(14) 0.80819(16) 0.0128(3) Uani 1 1 d . . . . .
O2 O 1.6958(3) -0.66817(12) 0.76003(14) 0.0153(3) Uani 1 1 d . . . . .
O3 O 1.5001(3) -0.77552(12) 0.90071(14) 0.0153(3) Uani 1 1 d . . . . .
N7 N 0.6450(4) -0.08663(15) 0.50604(16) 0.0134(3) Uani 1 1 d . . . . .
O1 O 1.0029(3) -0.40154(13) 0.79385(16) 0.0216(3) Uani 1 1 d . . . . .
N63 N 1.4528(3) -0.47327(13) 0.83372(16) 0.0118(3) Uani 1 1 d . . . . .
N1 N 1.1210(3) -0.08465(15) 0.83316(16) 0.0140(3) Uani 1 1 d . . . . .
C6 C 1.0320(4) -0.12550(16) 0.71034(19) 0.0112(4) Uani 1 1 d . . . . .
N6 N 1.1716(4) -0.21354(13) 0.66608(17) 0.0128(3) Uani 1 1 d . . . . .
C65 C 1.5421(4) -0.68004(16) 0.84269(18) 0.0116(4) Uani 1 1 d . . . . .
C61 C 1.3854(4) -0.28083(16) 0.7491(2) 0.0134(4) Uani 1 1 d . . . . .
H61A H 1.4693 -0.2353 0.8275 0.016 Uiso 1 1 calc R U . . .
H61B H 1.5405 -0.2997 0.7002 0.016 Uiso 1 1 calc R U . . .
C4 C 0.6617(4) 0.01759(16) 0.68453(18) 0.0118(4) Uani 1 1 d . . . . .
C2 C 0.9827(4) 0.00447(17) 0.87308(18) 0.0139(4) Uani 1 1 d . . . . .
H2 H 1.0574 0.0329 0.9586 0.017 Uiso 1 1 calc R U . . .
C64 C 1.3777(4) -0.58126(17) 0.88716(18) 0.0129(4) Uani 1 1 d . . . . .
H64A H 1.1702 -0.5949 0.8588 0.015 Uiso 1 1 calc R U . . .
H64B H 1.4178 -0.5772 0.9846 0.015 Uiso 1 1 calc R U . . .
N9 N 0.4310(4) 0.05600(14) 0.59585(16) 0.0140(3) Uani 1 1 d . . . . .
C5 C 0.7967(4) -0.07118(16) 0.63154(18) 0.0116(4) Uani 1 1 d . . . . .
C62 C 1.2608(4) -0.39155(16) 0.79379(18) 0.0117(4) Uani 1 1 d . . . . .
C8 C 0.4310(4) -0.00947(17) 0.49057(19) 0.0145(4) Uani 1 1 d . . . . .
H8 H 0.2933 -0.0025 0.4119 0.017 Uiso 1 1 calc R U . . .
O1W O 0.9359(3) -0.25869(13) 0.39663(14) 0.0152(3) Uani 1 1 d . . . . .
H63 H 1.636(6) -0.461(2) 0.830(2) 0.018(6) Uiso 1 1 d . . . . .
H1W H 0.832(7) -0.320(3) 0.384(3) 0.028(8) Uiso 1 1 d . . . . .
H6 H 1.110(6) -0.241(3) 0.588(3) 0.023(7) Uiso 1 1 d . . . . .
H3 H 1.604(9) -0.838(4) 0.867(4) 0.064(11) Uiso 1 1 d . . . . .
H7 H 0.690(7) -0.136(3) 0.452(3) 0.032(8) Uiso 1 1 d . . . . .
H2W H 1.044(6) -0.247(2) 0.340(3) 0.018(6) 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
N3 C2 1.328(3) . ?
N3 C4 1.358(3) . ?
O2 C65 1.226(2) . ?
O3 C65 1.299(2) . ?
N7 C8 1.347(3) . ?
N7 C5 1.375(3) . ?
O1 C62 1.232(2) . ?
N63 C62 1.334(2) . ?
N63 C64 1.448(2) . ?
N1 C2 1.336(3) . ?
N1 C6 1.349(2) . ?
C6 N6 1.349(2) . ?
C6 C5 1.410(3) . ?
N6 C61 1.439(2) . ?
C65 C64 1.512(3) . ?
C61 C62 1.529(3) . ?
C4 N9 1.371(2) . ?
C4 C5 1.384(2) . ?
N9 C8 1.329(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 N3 C4 113.86(16) . . ?
C8 N7 C5 106.28(17) . . ?
C62 N63 C64 122.70(16) . . ?
C2 N1 C6 118.49(16) . . ?
N1 C6 N6 119.86(17) . . ?
N1 C6 C5 117.65(17) . . ?
N6 C6 C5 122.46(18) . . ?
C6 N6 C61 123.65(17) . . ?
O2 C65 O3 125.29(18) . . ?
O2 C65 C64 121.99(17) . . ?
O3 C65 C64 112.72(16) . . ?
N6 C61 C62 111.84(15) . . ?
N3 C4 N9 126.60(17) . . ?
N3 C4 C5 122.62(17) . . ?
N9 C4 C5 110.78(17) . . ?
N3 C2 N1 128.14(17) . . ?
N63 C64 C65 112.00(15) . . ?
C8 N9 C4 103.79(16) . . ?
N7 C5 C4 105.56(17) . . ?
N7 C5 C6 135.27(18) . . ?
C4 C5 C6 119.12(17) . . ?
O1 C62 N63 123.88(18) . . ?
O1 C62 C61 121.34(17) . . ?
N63 C62 C61 114.77(16) . . ?
N9 C8 N7 113.60(17) . . ?

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
C61 H61B O1 0.99 2.53 3.215(2) 125.8 1_655
C64 H64A O2 0.99 2.46 3.425(2) 166.1 1_455
C64 H64B N1 0.99 2.62 3.395(3) 135.2 2_847
C8 H8 O2 0.95 2.63 3.150(2) 114.7 2_756
C8 H8 O1 0.95 2.61 3.503(2) 157.1 2_656
N63 H63 O1 0.89(3) 1.97(3) 2.846(2) 166(2) 1_655
O1W H1W N9 0.86(3) 1.95(3) 2.791(2) 163(3) 2_646
N6 H6 O1W 0.87(3) 2.01(3) 2.852(2) 164(3) .
O3 H3 N3 0.98(4) 1.58(4) 2.562(2) 177(4) 1_645
N7 H7 O2 0.86(3) 2.61(3) 3.076(2) 115(3) 2_756
N7 H7 O1W 0.86(3) 2.00(3) 2.792(2) 154(3) .
O1W H2W O2 0.85(3) 1.98(3) 2.796(2) 160(3) 2_856

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

