# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1528430'
_audit_update_record             
;
2017-01-19 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 Cl N4 O5 S'
_chemical_formula_weight         321.72

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9000(14)
_cell_length_b                   9.831(2)
_cell_length_c                   10.739(2)
_cell_angle_alpha                96.01(3)
_cell_angle_beta                 106.05(3)
_cell_angle_gamma                102.06(3)
_cell_volume                     674.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             330
_exptl_absorpt_coefficient_mu    0.463
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9131
_exptl_absorpt_correction_T_max  0.9552
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ;Nonius
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2702
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.39
_reflns_number_total             2477
_reflns_number_gt                1629
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2477
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.1884
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.9537(3) 1.26781(19) 1.51597(13) 0.0793(6) Uani 1 1 d . . .
N1 N 0.5840(7) 0.7529(4) 0.5853(4) 0.0455(10) Uani 1 1 d . . .
C1 C 0.6272(8) 0.7579(5) 0.7115(5) 0.0455(12) Uani 1 1 d . . .
H1B H 0.6303 0.6819 0.7562 0.055 Uiso 1 1 calc R . .
C2 C 0.6470(9) 0.9690(5) 0.6633(4) 0.0477(13) Uani 1 1 d . . .
H2A H 0.6685 1.0667 0.6734 0.057 Uiso 1 1 calc R . .
N2 N 0.5946(7) 0.8842(4) 0.5515(4) 0.0495(11) Uani 1 1 d . . .
C3 C 0.7436(8) 1.0608(5) 0.9436(4) 0.0401(11) Uani 1 1 d . . .
H3A H 0.7296 1.1247 0.8857 0.048 Uiso 1 1 calc R . .
N3 N 0.6660(6) 0.8928(3) 0.7642(3) 0.0354(9) Uani 1 1 d . . .
N4 N 0.7169(6) 0.9315(4) 0.9006(3) 0.0397(10) Uani 1 1 d . . .
C4 C 0.7968(7) 1.1096(4) 1.0858(4) 0.0356(10) Uani 1 1 d . . .
C5 C 0.8355(9) 1.2520(5) 1.1317(5) 0.0507(14) Uani 1 1 d . . .
H5A H 0.8293 1.3148 1.0725 0.061 Uiso 1 1 calc R . .
C6 C 0.8834(9) 1.3027(6) 1.2645(5) 0.0575(15) Uani 1 1 d . . .
H6A H 0.9099 1.3987 1.2956 0.069 Uiso 1 1 calc R . .
C7 C 0.8905(8) 1.2080(6) 1.3486(5) 0.0491(13) Uani 1 1 d . . .
C8 C 0.8494(9) 1.0651(6) 1.3068(5) 0.0514(13) Uani 1 1 d . . .
H8A H 0.8537 1.0029 1.3665 0.062 Uiso 1 1 calc R . .
C9 C 0.8012(8) 1.0156(5) 1.1727(5) 0.0442(12) Uani 1 1 d . . .
H9A H 0.7719 0.9192 1.1418 0.053 Uiso 1 1 calc R . .
S S 0.3709(2) 0.60567(11) 0.23876(10) 0.0348(3) Uani 1 1 d . . .
O1 O 0.5483(6) 0.7115(3) 0.2137(4) 0.0624(11) Uani 1 1 d . . .
O2 O 0.2974(6) 0.4876(3) 0.1333(3) 0.0531(10) Uani 1 1 d . . .
O3 O 0.2238(6) 0.6882(4) 0.2423(3) 0.0513(9) Uani 1 1 d . . .
O4 O 0.4508(6) 0.5603(3) 0.3625(3) 0.0575(11) Uani 1 1 d . . .
H4A H 0.5783 0.5927 0.4071 0.069 Uiso 1 1 d R . .
OW O 0.8015(6) 0.6065(5) 0.1287(4) 0.0834(14) Uani 1 1 d . . .
HWD H 0.7995 0.6095 0.2077 0.100 Uiso 1 1 d R . .
HWA H 0.8780 0.6847 0.1245 0.100 Uiso 1 1 d R . .


_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
Cl C7 1.733(5) . ?
N1 C1 1.298(6) . ?
N1 N2 1.370(5) . ?
C1 N3 1.327(6) . ?
C1 H1B 0.9300 . ?
C2 N2 1.301(6) . ?
C2 N3 1.372(5) . ?
C2 H2A 0.9300 . ?
C3 N4 1.264(6) . ?
C3 C4 1.470(6) . ?
C3 H3A 0.9300 . ?
N3 N4 1.400(5) . ?
C4 C5 1.378(6) . ?
C4 C9 1.379(6) . ?
C5 C6 1.384(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.362(7) . ?
C6 H6A 0.9300 . ?
C7 C8 1.374(7) . ?
C8 C9 1.394(6) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
S O2 1.432(3) . ?
S O3 1.432(4) . ?
S O4 1.446(3) . ?
S O1 1.537(4) . ?
O4 H4A 0.8500 . ?
OW HWD 0.8500 . ?
OW HWA 0.8500 . ?

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 N2 112.1(4) . . ?
N1 C1 N3 106.4(4) . . ?
N1 C1 H1B 126.8 . . ?
N3 C1 H1B 126.8 . . ?
N2 C2 N3 109.8(4) . . ?
N2 C2 H2A 125.1 . . ?
N3 C2 H2A 125.1 . . ?
C2 N2 N1 104.2(4) . . ?
N4 C3 C4 119.5(4) . . ?
N4 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C1 N3 C2 107.5(4) . . ?
C1 N3 N4 119.6(4) . . ?
C2 N3 N4 132.9(3) . . ?
C3 N4 N3 116.3(4) . . ?
C5 C4 C9 119.9(4) . . ?
C5 C4 C3 118.8(4) . . ?
C9 C4 C3 121.3(4) . . ?
C4 C5 C6 120.9(5) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C7 C6 C5 118.2(5) . . ?
C7 C6 H6A 120.9 . . ?
C5 C6 H6A 120.9 . . ?
C6 C7 C8 122.8(5) . . ?
C6 C7 Cl 119.5(4) . . ?
C8 C7 Cl 117.7(4) . . ?
C7 C8 C9 118.4(5) . . ?
C7 C8 H8A 120.8 . . ?
C9 C8 H8A 120.8 . . ?
C4 C9 C8 119.9(5) . . ?
C4 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
O2 S O3 114.3(2) . . ?
O2 S O4 110.15(19) . . ?
O3 S O4 112.8(2) . . ?
O2 S O1 108.0(2) . . ?
O3 S O1 102.2(2) . . ?
O4 S O1 108.9(2) . . ?
S O4 H4A 119.5 . . ?
HWD OW HWA 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C1 N3 0.4(6) . . . . ?
N3 C2 N2 N1 -0.8(6) . . . . ?
C1 N1 N2 C2 0.2(6) . . . . ?
N1 C1 N3 C2 -0.9(6) . . . . ?
N1 C1 N3 N4 179.7(4) . . . . ?
N2 C2 N3 C1 1.1(6) . . . . ?
N2 C2 N3 N4 -179.6(5) . . . . ?
C4 C3 N4 N3 179.8(4) . . . . ?
C1 N3 N4 C3 -177.2(5) . . . . ?
C2 N3 N4 C3 3.5(8) . . . . ?
N4 C3 C4 C5 176.8(5) . . . . ?
N4 C3 C4 C9 -5.5(8) . . . . ?
C9 C4 C5 C6 1.4(9) . . . . ?
C3 C4 C5 C6 179.1(5) . . . . ?
C4 C5 C6 C7 -0.2(9) . . . . ?
C5 C6 C7 C8 -1.0(9) . . . . ?
C5 C6 C7 Cl 179.1(4) . . . . ?
C6 C7 C8 C9 0.9(9) . . . . ?
Cl C7 C8 C9 -179.2(4) . . . . ?
C5 C4 C9 C8 -1.5(8) . . . . ?
C3 C4 C9 C8 -179.1(5) . . . . ?
C7 C8 C9 C4 0.4(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.39
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.093
####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1524378'
_audit_update_record             
;
2016-12-24 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N8 O8 S'
_chemical_formula_weight         510.50

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   Cc

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.7700(14)
_cell_length_b                   20.084(4)
_cell_length_c                   16.848(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.50(3)
_cell_angle_gamma                90.00
_cell_volume                     2244.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       stick
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9595
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            4459
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_sigmaI/netI    0.0942
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.40
_reflns_number_total             2266
_reflns_number_gt                1466
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0410P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.38(18)
_refine_ls_number_reflns         2266
_refine_ls_number_parameters     316
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.1316(3) 0.12493(9) 0.78333(12) 0.0375(4) Uani 1 1 d . . .
O1 O 0.5833(8) 0.0129(3) 1.5558(3) 0.0606(16) Uani 1 1 d . . .
H1A H 0.6032 0.0383 1.5948 0.091 Uiso 1 1 calc R . .
N1 N 0.3226(9) 0.1734(3) 0.9988(4) 0.0461(16) Uani 1 1 d . . .
H1B H 0.2968 0.1659 0.9476 0.055 Uiso 1 1 calc R . .
C1 C 0.3509(10) 0.1275(5) 1.0528(4) 0.0467(18) Uani 1 1 d . . .
H1C H 0.3471 0.0819 1.0432 0.056 Uiso 1 1 calc R . .
N2 N 0.3379(10) 0.2350(3) 1.0318(4) 0.0530(18) Uani 1 1 d . . .
C2 C 0.3744(11) 0.2233(4) 1.1098(5) 0.0497(19) Uani 1 1 d . . .
H2B H 0.3897 0.2562 1.1495 0.060 Uiso 1 1 calc R . .
O2 O -0.1873(8) -0.2372(3) 0.5106(3) 0.0592(15) Uani 1 1 d . . .
H2C H -0.2120 -0.2165 0.4657 0.071 Uiso 1 1 d R . .
O3 O -0.0166(12) 0.1724(3) 0.7460(5) 0.114(3) Uani 1 1 d . . .
N3 N 0.3870(8) 0.1572(3) 1.1253(3) 0.0376(14) Uani 1 1 d . . .
C3 C 0.4632(10) 0.1518(3) 1.2622(4) 0.0398(17) Uani 1 1 d . . .
H3B H 0.4703 0.1980 1.2614 0.048 Uiso 1 1 calc R . .
O4 O 0.2893(11) 0.1569(4) 0.8421(4) 0.101(3) Uani 1 1 d . . .
N4 N 0.4223(9) 0.1197(3) 1.1969(3) 0.0437(14) Uani 1 1 d . . .
C4 C 0.4991(10) 0.1165(4) 1.3385(4) 0.0382(17) Uani 1 1 d . . .
O5 O 0.0241(12) 0.0788(3) 0.8219(5) 0.115(3) Uani 1 1 d . . .
C5 C 0.5373(11) 0.1496(3) 1.4115(4) 0.0434(18) Uani 1 1 d . . .
H5B H 0.5444 0.1958 1.4110 0.052 Uiso 1 1 calc R . .
N5 N 0.1065(9) -0.0764(3) 1.0682(4) 0.0461(16) Uani 1 1 d . . .
H5A H 0.1316 -0.0834 1.1196 0.055 Uiso 1 1 calc R . .
O6 O 0.2284(10) 0.0931(5) 0.7252(4) 0.104(3) Uani 1 1 d . . .
C6 C 0.5656(11) 0.1179(4) 1.4850(4) 0.0462(19) Uani 1 1 d . . .
H6B H 0.5886 0.1421 1.5330 0.055 Uiso 1 1 calc R . .
N6 N 0.0868(10) -0.0150(3) 1.0327(4) 0.0490(17) Uani 1 1 d . . .
C7 C 0.5589(11) 0.0490(4) 1.4857(4) 0.0451(18) Uani 1 1 d . . .
N7 N 0.0457(8) -0.0933(3) 0.9407(3) 0.0373(14) Uani 1 1 d . . .
C8 C 0.5241(12) 0.0127(3) 1.4141(5) 0.054(2) Uani 1 1 d . . .
H8A H 0.5196 -0.0335 1.4152 0.064 Uiso 1 1 calc R . .
N8 N 0.0094(9) -0.1311(3) 0.8703(3) 0.0416(14) Uani 1 1 d . . .
C9 C 0.4967(11) 0.0459(4) 1.3422(4) 0.0489(19) Uani 1 1 d . . .
H9A H 0.4759 0.0216 1.2942 0.059 Uiso 1 1 calc R . .
C10 C 0.0818(11) -0.1232(5) 1.0128(4) 0.0468(18) Uani 1 1 d . . .
H10A H 0.0881 -0.1689 1.0221 0.056 Uiso 1 1 calc R . .
C11 C 0.0495(12) -0.0266(4) 0.9562(4) 0.0465(19) Uani 1 1 d . . .
H11A H 0.0280 0.0063 0.9165 0.056 Uiso 1 1 calc R . .
C12 C -0.0166(11) -0.0990(4) 0.8034(5) 0.0419(18) Uani 1 1 d . . .
H12A H -0.0106 -0.0528 0.8037 0.050 Uiso 1 1 calc R . .
C13 C -0.0556(10) -0.1349(4) 0.7270(4) 0.0390(17) Uani 1 1 d . . .
C14 C -0.0637(11) -0.2034(3) 0.7253(4) 0.0451(18) Uani 1 1 d . . .
H14A H -0.0410 -0.2274 0.7735 0.054 Uiso 1 1 calc R . .
C15 C -0.1054(11) -0.2363(4) 0.6522(5) 0.052(2) Uani 1 1 d . . .
H15A H -0.1080 -0.2826 0.6514 0.063 Uiso 1 1 calc R . .
C16 C -0.1435(11) -0.2014(4) 0.5796(4) 0.0439(18) Uani 1 1 d . . .
C17 C -0.1347(11) -0.1344(4) 0.5816(4) 0.0427(18) Uani 1 1 d . . .
H17A H -0.1573 -0.1106 0.5333 0.051 Uiso 1 1 calc R . .
C18 C -0.0925(11) -0.1007(3) 0.6545(4) 0.0441(18) Uani 1 1 d . . .
H18A H -0.0890 -0.0544 0.6547 0.053 Uiso 1 1 calc R . .
OW1 O 0.6124(9) 0.0866(4) 1.6870(4) 0.085(2) Uani 1 1 d . . .
HW1A H 0.6048 0.1287 1.6825 0.102 Uiso 1 1 d R . .
HW1B H 0.6282 0.0686 1.7335 0.102 Uiso 1 1 d R . .
OW2 O -0.2950(10) 0.1643(4) 0.8778(3) 0.086(2) Uani 1 1 d . . .
HW2C H -0.1995 0.1481 0.8579 0.104 Uiso 1 1 d R . .
HW2D H -0.3134 0.1380 0.9152 0.104 Uiso 1 1 d R . .


_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
S O5 1.415(6) . ?
S O6 1.432(6) . ?
S O3 1.435(6) . ?
S O4 1.453(6) . ?
O1 C7 1.368(8) . ?
O1 H1A 0.8200 . ?
N1 C1 1.282(10) . ?
N1 N2 1.352(8) . ?
N1 H1B 0.8600 . ?
C1 N3 1.338(9) . ?
C1 H1C 0.9300 . ?
N2 C2 1.310(10) . ?
C2 N3 1.354(9) . ?
C2 H2B 0.9300 . ?
O2 C16 1.349(8) . ?
O2 H2C 0.8499 . ?
N3 N4 1.401(8) . ?
C3 N4 1.258(8) . ?
C3 C4 1.446(10) . ?
C3 H3B 0.9300 . ?
C4 C5 1.376(9) . ?
C4 C9 1.421(10) . ?
C5 C6 1.370(10) . ?
C5 H5B 0.9300 . ?
N5 C10 1.311(10) . ?
N5 N6 1.365(8) . ?
N5 H5A 0.8600 . ?
C6 C7 1.385(11) . ?
C6 H6B 0.9300 . ?
N6 C11 1.285(9) . ?
C7 C8 1.389(9) . ?
N7 C10 1.333(9) . ?
N7 C11 1.363(8) . ?
N7 N8 1.390(8) . ?
C8 C9 1.362(10) . ?
C8 H8A 0.9300 . ?
N8 C12 1.279(9) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.453(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.377(10) . ?
C13 C18 1.381(9) . ?
C14 C15 1.377(10) . ?
C14 H14A 0.9300 . ?
C15 C16 1.389(9) . ?
C15 H15A 0.9300 . ?
C16 C17 1.346(10) . ?
C17 C18 1.381(10) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
OW1 HW1A 0.8502 . ?
OW1 HW1B 0.8501 . ?
OW2 HW2C 0.8500 . ?
OW2 HW2D 0.8499 . ?

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
O5 S O6 111.6(5) . . ?
O5 S O3 104.9(5) . . ?
O6 S O3 111.8(5) . . ?
O5 S O4 110.6(5) . . ?
O6 S O4 106.8(4) . . ?
O3 S O4 111.1(5) . . ?
C7 O1 H1A 109.5 . . ?
C1 N1 N2 112.2(6) . . ?
C1 N1 H1B 123.9 . . ?
N2 N1 H1B 123.9 . . ?
N1 C1 N3 107.6(8) . . ?
N1 C1 H1C 126.2 . . ?
N3 C1 H1C 126.2 . . ?
C2 N2 N1 103.4(6) . . ?
N2 C2 N3 111.2(7) . . ?
N2 C2 H2B 124.4 . . ?
N3 C2 H2B 124.4 . . ?
C16 O2 H2C 118.6 . . ?
C1 N3 C2 105.5(7) . . ?
C1 N3 N4 121.0(6) . . ?
C2 N3 N4 133.4(6) . . ?
N4 C3 C4 119.7(7) . . ?
N4 C3 H3B 120.1 . . ?
C4 C3 H3B 120.1 . . ?
C3 N4 N3 116.6(7) . . ?
C5 C4 C9 116.4(7) . . ?
C5 C4 C3 121.8(7) . . ?
C9 C4 C3 121.8(6) . . ?
C6 C5 C4 123.5(7) . . ?
C6 C5 H5B 118.3 . . ?
C4 C5 H5B 118.3 . . ?
C10 N5 N6 110.4(6) . . ?
C10 N5 H5A 124.8 . . ?
N6 N5 H5A 124.8 . . ?
C5 C6 C7 118.2(7) . . ?
C5 C6 H6B 120.9 . . ?
C7 C6 H6B 120.9 . . ?
C11 N6 N5 105.0(6) . . ?
O1 C7 C6 122.7(7) . . ?
O1 C7 C8 116.2(6) . . ?
C6 C7 C8 121.1(7) . . ?
C10 N7 C11 106.0(6) . . ?
C10 N7 N8 120.0(6) . . ?
C11 N7 N8 133.9(6) . . ?
C9 C8 C7 119.1(7) . . ?
C9 C8 H8A 120.5 . . ?
C7 C8 H8A 120.5 . . ?
C12 N8 N7 116.6(6) . . ?
C8 C9 C4 121.7(7) . . ?
C8 C9 H9A 119.1 . . ?
C4 C9 H9A 119.1 . . ?
N5 C10 N7 107.4(7) . . ?
N5 C10 H10A 126.3 . . ?
N7 C10 H10A 126.3 . . ?
N6 C11 N7 111.2(6) . . ?
N6 C11 H11A 124.4 . . ?
N7 C11 H11A 124.4 . . ?
N8 C12 C13 120.0(7) . . ?
N8 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C14 C13 C18 118.7(7) . . ?
C14 C13 C12 120.9(7) . . ?
C18 C13 C12 120.4(7) . . ?
C13 C14 C15 119.9(7) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 C16 120.9(7) . . ?
C14 C15 H15A 119.5 . . ?
C16 C15 H15A 119.5 . . ?
C17 C16 O2 123.7(7) . . ?
C17 C16 C15 118.9(7) . . ?
O2 C16 C15 117.4(7) . . ?
C16 C17 C18 120.8(7) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C13 C18 C17 120.7(7) . . ?
C13 C18 H18A 119.6 . . ?
C17 C18 H18A 119.6 . . ?
HW1A OW1 HW1B 120.0 . . ?
HW2C OW2 HW2D 106.9 . . ?

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
N2 N1 C1 N3 0.0(8) . . . . ?
C1 N1 N2 C2 -1.0(8) . . . . ?
N1 N2 C2 N3 1.6(8) . . . . ?
N1 C1 N3 C2 1.0(8) . . . . ?
N1 C1 N3 N4 179.4(6) . . . . ?
N2 C2 N3 C1 -1.7(8) . . . . ?
N2 C2 N3 N4 -179.9(7) . . . . ?
C4 C3 N4 N3 179.2(6) . . . . ?
C1 N3 N4 C3 177.1(6) . . . . ?
C2 N3 N4 C3 -4.9(11) . . . . ?
N4 C3 C4 C5 -177.7(7) . . . . ?
N4 C3 C4 C9 2.3(11) . . . . ?
C9 C4 C5 C6 -2.2(11) . . . . ?
C3 C4 C5 C6 177.8(7) . . . . ?
C4 C5 C6 C7 1.2(11) . . . . ?
C10 N5 N6 C11 0.2(8) . . . . ?
C5 C6 C7 O1 -179.3(6) . . . . ?
C5 C6 C7 C8 -0.1(12) . . . . ?
O1 C7 C8 C9 179.4(7) . . . . ?
C6 C7 C8 C9 0.2(12) . . . . ?
C10 N7 N8 C12 -177.5(6) . . . . ?
C11 N7 N8 C12 4.5(11) . . . . ?
C7 C8 C9 C4 -1.2(12) . . . . ?
C5 C4 C9 C8 2.1(11) . . . . ?
C3 C4 C9 C8 -177.9(7) . . . . ?
N6 N5 C10 N7 0.0(8) . . . . ?
C11 N7 C10 N5 -0.3(8) . . . . ?
N8 N7 C10 N5 -178.7(6) . . . . ?
N5 N6 C11 N7 -0.4(8) . . . . ?
C10 N7 C11 N6 0.4(8) . . . . ?
N8 N7 C11 N6 178.6(7) . . . . ?
N7 N8 C12 C13 -179.9(6) . . . . ?
N8 C12 C13 C14 -0.5(11) . . . . ?
N8 C12 C13 C18 177.2(7) . . . . ?
C18 C13 C14 C15 0.9(11) . . . . ?
C12 C13 C14 C15 178.5(7) . . . . ?
C13 C14 C15 C16 -1.3(12) . . . . ?
C14 C15 C16 C17 1.5(12) . . . . ?
C14 C15 C16 O2 -178.6(7) . . . . ?
O2 C16 C17 C18 178.8(7) . . . . ?
C15 C16 C17 C18 -1.3(12) . . . . ?
C14 C13 C18 C17 -0.7(11) . . . . ?
C12 C13 C18 C17 -178.4(7) . . . . ?
C16 C17 C18 C13 0.9(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.40
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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 1524379'
_audit_update_record             
;
2016-12-24 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 N5 O5'
_chemical_formula_weight         269.23

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/C

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.1440(14)
_cell_length_b                   18.168(4)
_cell_length_c                   9.3760(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.84(3)
_cell_angle_gamma                90.00
_cell_volume                     1176.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       stick
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2275
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         25.37
_reflns_number_total             2108
_reflns_number_gt                1381
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2108
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1022
_refine_ls_R_factor_gt           0.0661
_refine_ls_wR_factor_ref         0.1848
_refine_ls_wR_factor_gt          0.1644
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6544(4) 0.22135(12) 0.3094(3) 0.0513(7) Uani 1 1 d . . .
H1A H 0.7222 0.1909 0.3636 0.077 Uiso 1 1 calc R . .
N1 N 0.7422(4) 0.74245(15) 0.5785(3) 0.0462(8) Uani 1 1 d . . .
H1B H 0.7168 0.7883 0.5602 0.055 Uiso 1 1 calc R . .
C1 C 0.6862(5) 0.69024(18) 0.4838(4) 0.0418(8) Uani 1 1 d . . .
H1C H 0.6123 0.6958 0.3872 0.050 Uiso 1 1 calc R . .
N2 N 0.8462(4) 0.71604(16) 0.7107(3) 0.0514(8) Uani 1 1 d . . .
C2 C 0.8530(5) 0.64546(19) 0.6900(4) 0.0461(9) Uani 1 1 d . . .
H2B H 0.9169 0.6120 0.7610 0.055 Uiso 1 1 calc R . .
C3 C 0.7846(4) 0.50364(18) 0.5485(4) 0.0380(8) Uani 1 1 d . . .
H3A H 0.8523 0.5087 0.6469 0.046 Uiso 1 1 calc R . .
N3 N 0.7532(4) 0.62700(13) 0.5493(3) 0.0340(6) Uani 1 1 d . . .
N4 N 0.7198(4) 0.56016(14) 0.4748(3) 0.0391(7) Uani 1 1 d . . .
C4 C 0.7562(4) 0.43127(17) 0.4840(3) 0.0360(8) Uani 1 1 d . . .
C5 C 0.8343(5) 0.37054(17) 0.5683(4) 0.0416(8) Uani 1 1 d . . .
H5A H 0.9074 0.3776 0.6648 0.050 Uiso 1 1 calc R . .
C6 C 0.8062(5) 0.30012(17) 0.5125(3) 0.0381(8) Uani 1 1 d . . .
H6A H 0.8613 0.2601 0.5700 0.046 Uiso 1 1 calc R . .
C7 C 0.6941(4) 0.28964(17) 0.3689(3) 0.0347(7) Uani 1 1 d . . .
C8 C 0.6213(5) 0.34977(18) 0.2833(3) 0.0392(8) Uani 1 1 d . . .
H8A H 0.5513 0.3427 0.1861 0.047 Uiso 1 1 calc R . .
C9 C 0.6495(5) 0.41937(18) 0.3381(4) 0.0390(8) Uani 1 1 d . . .
H9A H 0.5979 0.4592 0.2786 0.047 Uiso 1 1 calc R . .
N5 N 0.8113(5) 0.06016(16) 0.4960(4) 0.0497(8) Uani 1 1 d . . .
O2 O 0.8827(4) 0.12267(13) 0.4928(3) 0.0656(9) Uani 1 1 d . . .
O3 O 0.6725(4) 0.04059(16) 0.3934(3) 0.0752(10) Uani 1 1 d . . .
O4 O 0.8832(4) 0.01885(14) 0.6010(3) 0.0560(7) Uani 1 1 d . . .
OW O 0.3261(4) 0.11481(13) 0.4136(4) 0.0720(9) Uani 1 1 d . . .
HWA H 0.2688 0.1308 0.4764 0.086 Uiso 1 1 d R . .
HWB H 0.3006 0.0720 0.3771 0.086 Uiso 1 1 d R . .


_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 C7 1.360(4) . ?
O1 H1A 0.8200 . ?
N1 C1 1.291(4) . ?
N1 N2 1.358(4) . ?
N1 H1B 0.8600 . ?
C1 N3 1.333(4) . ?
C1 H1C 0.9300 . ?
N2 C2 1.300(4) . ?
C2 N3 1.370(4) . ?
C2 H2B 0.9300 . ?
C3 N4 1.258(4) . ?
C3 C4 1.440(4) . ?
C3 H3A 0.9300 . ?
N3 N4 1.391(3) . ?
C4 C5 1.389(4) . ?
C4 C9 1.401(4) . ?
C5 C6 1.377(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.392(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.376(4) . ?
C8 C9 1.360(4) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
N5 O4 1.240(4) . ?
N5 O3 1.244(4) . ?
N5 O2 1.249(4) . ?
OW HWA 0.8501 . ?
OW HWB 0.8500 . ?

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
C7 O1 H1A 109.5 . . ?
C1 N1 N2 111.6(3) . . ?
C1 N1 H1B 124.2 . . ?
N2 N1 H1B 124.2 . . ?
N1 C1 N3 107.7(3) . . ?
N1 C1 H1C 126.1 . . ?
N3 C1 H1C 126.1 . . ?
C2 N2 N1 104.2(3) . . ?
N2 C2 N3 110.8(3) . . ?
N2 C2 H2B 124.6 . . ?
N3 C2 H2B 124.6 . . ?
N4 C3 C4 121.5(3) . . ?
N4 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C1 N3 C2 105.6(3) . . ?
C1 N3 N4 121.7(2) . . ?
C2 N3 N4 132.6(3) . . ?
C3 N4 N3 116.4(3) . . ?
C5 C4 C9 118.2(3) . . ?
C5 C4 C3 119.6(3) . . ?
C9 C4 C3 122.3(3) . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 H6A 120.4 . . ?
C7 C6 H6A 120.4 . . ?
O1 C7 C8 118.5(3) . . ?
O1 C7 C6 121.9(3) . . ?
C8 C7 C6 119.5(3) . . ?
C9 C8 C7 121.4(3) . . ?
C9 C8 H8A 119.3 . . ?
C7 C8 H8A 119.3 . . ?
C8 C9 C4 120.2(3) . . ?
C8 C9 H9A 119.9 . . ?
C4 C9 H9A 119.9 . . ?
O4 N5 O3 121.8(3) . . ?
O4 N5 O2 118.7(3) . . ?
O3 N5 O2 119.4(3) . . ?
HWA OW HWB 120.0 . . ?

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
N2 N1 C1 N3 -0.8(4) . . . . ?
C1 N1 N2 C2 1.1(4) . . . . ?
N1 N2 C2 N3 -1.0(4) . . . . ?
N1 C1 N3 C2 0.1(4) . . . . ?
N1 C1 N3 N4 -178.9(3) . . . . ?
N2 C2 N3 C1 0.6(4) . . . . ?
N2 C2 N3 N4 179.5(3) . . . . ?
C4 C3 N4 N3 179.0(3) . . . . ?
C1 N3 N4 C3 -177.9(3) . . . . ?
C2 N3 N4 C3 3.5(5) . . . . ?
N4 C3 C4 C5 178.4(3) . . . . ?
N4 C3 C4 C9 -2.4(5) . . . . ?
C9 C4 C5 C6 -1.1(5) . . . . ?
C3 C4 C5 C6 178.1(3) . . . . ?
C4 C5 C6 C7 -1.0(5) . . . . ?
C5 C6 C7 O1 -177.3(3) . . . . ?
C5 C6 C7 C8 3.0(5) . . . . ?
O1 C7 C8 C9 177.4(3) . . . . ?
C6 C7 C8 C9 -2.9(5) . . . . ?
C7 C8 C9 C4 0.6(5) . . . . ?
C5 C4 C9 C8 1.3(5) . . . . ?
C3 C4 C9 C8 -177.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.063
####################################################################### 
# 
# 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_WJW
_database_code_depnum_ccdc_archive 'CCDC 1528432'
_audit_update_record             
;
2017-01-19 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 N8 O9 S'
_chemical_formula_weight         552.53

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

_cell_length_a                   7.0119(14)
_cell_length_b                   20.686(4)
_cell_length_c                   16.829(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2441.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.201
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15202
_diffrn_reflns_av_unetI/netI     0.0600
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.068
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2800
_reflns_number_gt                1829
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.1131P)²+3.4209P] 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         2800
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.0891
_refine_ls_wR_factor_ref         0.2496
_refine_ls_wR_factor_gt          0.2198
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.004
_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
N2 N 0.1707(5) 0.83859(16) 0.90961(19) 0.0340(8) Uani 1 1 d . . . . .
N1 N 0.2041(5) 0.87919(16) 0.84350(19) 0.0356(9) Uani 1 1 d . . . . .
O5 O 0.2688(5) 0.98779(14) 0.49277(16) 0.0462(9) Uani 1 1 d . . . . .
C5 C 0.3042(6) 0.8536(2) 0.6361(2) 0.0361(10) Uani 1 1 d . . . . .
H5 H 0.3282 0.8094 0.6381 0.043 Uiso 1 1 calc R U . . .
O4 O 0.2050(6) 1.05041(14) 0.62269(18) 0.0511(10) Uani 1 1 d . . . . .
H4A H 0.1950 1.0670 0.6667 0.077 Uiso 1 1 calc R U . . .
C1 C 0.2733(6) 0.9513(2) 0.5598(2) 0.0343(10) Uani 1 1 d . . . . .
C4 C 0.2642(6) 0.88675(19) 0.7052(2) 0.0328(9) Uani 1 1 d . . . . .
C7 C 0.2471(6) 0.8507(2) 0.7794(2) 0.0358(10) Uani 1 1 d . . . . .
H7 H 0.2679 0.8063 0.7795 0.043 Uiso 1 1 calc R U . . .
C3 C 0.2321(6) 0.9540(2) 0.7024(2) 0.0352(10) Uani 1 1 d . . . . .
H3 H 0.2075 0.9767 0.7489 0.042 Uiso 1 1 calc R U . . .
C10 C 0.1650(7) 0.8612(2) 0.9834(2) 0.0401(11) Uani 1 1 d . . . . .
H10 H 0.1951 0.9030 0.9994 0.048 Uiso 1 1 calc R U . . .
C8 C 0.2974(8) 0.9551(2) 0.4181(3) 0.0548(14) Uani 1 1 d . . . . .
H8A H 0.4155 0.9316 0.4197 0.082 Uiso 1 1 calc R U . . .
H8B H 0.3017 0.9863 0.3760 0.082 Uiso 1 1 calc R U . . .
H8C H 0.1941 0.9256 0.4090 0.082 Uiso 1 1 calc R U . . .
C6 C 0.3091(6) 0.8857(2) 0.5632(2) 0.0356(10) Uani 1 1 d . . . . .
H6 H 0.3366 0.8629 0.5170 0.043 Uiso 1 1 calc R U . . .
N3 N 0.0720(6) 0.75956(17) 0.9868(2) 0.0474(10) Uani 1 1 d . . . . .
C2 C 0.2369(6) 0.98586(19) 0.6310(2) 0.0350(10) Uani 1 1 d . . . . .
C9 C 0.1112(7) 0.7753(2) 0.9137(3) 0.0441(12) Uani 1 1 d . . . . .
H9 H 0.1005 0.7477 0.8703 0.053 Uiso 1 1 calc R U . . .
N4 N 0.1096(6) 0.81418(17) 1.0290(2) 0.0429(10) Uani 1 1 d . . . . .
H4 H 0.0980 0.8172 1.0797 0.051 Uiso 1 1 calc R U . . .
S1 S 0.0000 0.16332(7) 0.7500 0.0337(4) Uani 1 2 d S T P . .
O2 O 0.0003(6) 0.20292(15) 0.82063(18) 0.0582(10) Uani 1 1 d . . . . .
O3 O 1.0000 0.7026(3) 0.7500 0.0741(18) Uani 1 2 d S T P . .
O1 O 0.1689(6) 0.12018(18) 0.7508(2) 0.0696(12) Uani 1 1 d . . . . .
H3W H 0.91(2) 0.676(6) 0.747(9) 0.25(7) 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
N2 C10 1.327(5) . ?
N2 C9 1.376(6) . ?
N2 N1 1.414(4) . ?
N1 C7 1.266(5) . ?
O5 C1 1.358(5) . ?
O5 C8 1.441(5) . ?
C5 C4 1.379(6) . ?
C5 C6 1.395(6) . ?
O4 C2 1.361(5) . ?
C1 C6 1.381(6) . ?
C1 C2 1.418(6) . ?
C4 C3 1.410(6) . ?
C4 C7 1.459(6) . ?
C3 C2 1.371(6) . ?
C10 N4 1.298(5) . ?
N3 C9 1.302(6) . ?
N3 N4 1.360(5) . ?
S1 O2 1.444(3) 3_556 ?
S1 O2 1.444(3) . ?
S1 O1 1.483(4) . ?
S1 O1 1.483(4) 3_556 ?

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
C10 N2 C9 106.2(4) . . ?
C10 N2 N1 122.1(3) . . ?
C9 N2 N1 130.9(3) . . ?
C7 N1 N2 115.7(3) . . ?
C1 O5 C8 117.4(3) . . ?
C4 C5 C6 120.6(4) . . ?
O5 C1 C6 125.9(4) . . ?
O5 C1 C2 114.6(3) . . ?
C6 C1 C2 119.5(4) . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 C7 118.9(4) . . ?
C3 C4 C7 121.3(4) . . ?
N1 C7 C4 120.7(4) . . ?
C2 C3 C4 120.0(4) . . ?
N4 C10 N2 107.3(4) . . ?
C1 C6 C5 120.0(4) . . ?
C9 N3 N4 104.2(4) . . ?
O4 C2 C3 123.9(4) . . ?
O4 C2 C1 116.0(3) . . ?
C3 C2 C1 120.1(4) . . ?
N3 C9 N2 110.4(4) . . ?
C10 N4 N3 111.8(3) . . ?
O2 S1 O2 110.9(3) 3_556 . ?
O2 S1 O1 110.5(2) 3_556 . ?
O2 S1 O1 109.5(2) . . ?
O2 S1 O1 109.5(2) 3_556 3_556 ?
O2 S1 O1 110.5(2) . 3_556 ?
O1 S1 O1 106.0(3) . 3_556 ?

_refine_diff_density_max         1.627
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.079

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1526869'
_audit_update_record             
;
2017-01-11 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 N5 O5'
_chemical_formula_weight         281.24

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                   8.8062(18)
_cell_length_b                   17.518(4)
_cell_length_c                   8.1176(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.15(3)
_cell_angle_gamma                90
_cell_volume                     1219.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1614
_cell_measurement_theta_min      3.294
_cell_measurement_theta_max      27.481

_exptl_crystal_description       prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8037
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.294
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2776
_reflns_number_gt                1614
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0780P)²+0.2811P] 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         2776
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1555
_refine_ls_R_factor_gt           0.0875
_refine_ls_wR_factor_ref         0.2043
_refine_ls_wR_factor_gt          0.1798
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_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
N2 N 0.2996(3) 0.11529(14) 1.0365(3) 0.0371(7) Uani 1 1 d . . . . .
O4 O 0.0747(3) 0.53130(11) 0.8009(3) 0.0480(7) Uani 1 1 d . . . . .
N3 N 0.2343(3) 0.18475(14) 0.9691(3) 0.0419(7) Uani 1 1 d . . . . .
N5 N 0.3208(3) -0.00426(16) 1.0627(4) 0.0418(7) Uani 1 1 d . . . . .
C7 C 0.0603(4) 0.39862(17) 0.7879(4) 0.0378(8) Uani 1 1 d . . . . .
O5 O -0.0604(3) 0.41020(12) 0.6527(3) 0.0598(8) Uani 1 1 d . . . . .
H5A H -0.0972 0.3689 0.6160 0.090 Uiso 1 1 calc R U . . .
C6 C 0.1102(4) 0.32772(18) 0.8447(4) 0.0401(8) Uani 1 1 d . . . . .
H6 H 0.0599 0.2847 0.7914 0.048 Uiso 1 1 calc R U . . .
C2 C 0.1335(4) 0.46425(17) 0.8702(4) 0.0359(8) Uani 1 1 d . . . . .
C4 C 0.3095(4) 0.38421(18) 1.0649(4) 0.0460(9) Uani 1 1 d . . . . .
H4 H 0.3927 0.3792 1.1580 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2954(4) 0.24432(18) 1.0437(4) 0.0430(8) Uani 1 1 d . . . . .
H8 H 0.3780 0.2401 1.1378 0.052 Uiso 1 1 calc R U . . .
C5 C 0.2372(4) 0.31944(17) 0.9834(4) 0.0389(8) Uani 1 1 d . . . . .
C9 C 0.4284(4) 0.09772(18) 1.1616(4) 0.0437(9) Uani 1 1 d . . . . .
H9 H 0.4951 0.1335 1.2250 0.052 Uiso 1 1 calc R U . . .
N4 N 0.4437(3) 0.02464(15) 1.1790(4) 0.0468(8) Uani 1 1 d . . . . .
C10 C 0.2353(4) 0.04965(18) 0.9777(4) 0.0407(8) Uani 1 1 d . . . . .
H10 H 0.1461 0.0432 0.8921 0.049 Uiso 1 1 calc R U . . .
C1 C 0.1475(5) 0.60058(18) 0.8740(5) 0.0558(10) Uani 1 1 d . . . . .
H1A H 0.0953 0.6436 0.8127 0.084 Uiso 1 1 calc R U . . .
H1B H 0.2551 0.6007 0.8679 0.084 Uiso 1 1 calc R U . . .
H1C H 0.1407 0.6038 0.9901 0.084 Uiso 1 1 calc R U . . .
C3 C 0.2574(4) 0.45633(18) 1.0072(4) 0.0433(8) Uani 1 1 d . . . . .
H3 H 0.3065 0.4995 1.0613 0.052 Uiso 1 1 calc R U . . .
O3 O 0.6204(3) 0.15616(14) 0.9216(4) 0.0633(8) Uani 1 1 d . . . . .
N1 N 0.6885(4) 0.21805(16) 0.9368(4) 0.0542(9) Uani 1 1 d . . . . .
O1 O 0.6198(4) 0.27642(16) 0.8843(5) 0.1024(13) Uani 1 1 d . . . . .
O2 O 0.8303(4) 0.22062(15) 1.0042(4) 0.0877(11) Uani 1 1 d . . . . .
H5 H 0.318(4) -0.060(2) 1.057(4) 0.052(10) 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
N2 C10 1.322(4) . ?
N2 C9 1.374(4) . ?
N2 N3 1.403(3) . ?
O4 C2 1.353(4) . ?
O4 C1 1.436(4) . ?
N3 C8 1.264(4) . ?
N5 C10 1.303(4) . ?
N5 N4 1.362(3) . ?
C7 O5 1.358(4) . ?
C7 C6 1.362(4) . ?
C7 C2 1.410(4) . ?
C6 C5 1.403(4) . ?
C2 C3 1.376(5) . ?
C4 C3 1.388(4) . ?
C4 C5 1.392(4) . ?
C8 C5 1.456(4) . ?
C9 N4 1.292(4) . ?
O3 N1 1.232(4) . ?
N1 O1 1.215(4) . ?
N1 O2 1.245(4) . ?

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
C10 N2 C9 106.6(3) . . ?
C10 N2 N3 120.7(3) . . ?
C9 N2 N3 132.7(3) . . ?
C2 O4 C1 118.0(3) . . ?
C8 N3 N2 115.9(3) . . ?
C10 N5 N4 111.7(3) . . ?
O5 C7 C6 122.9(3) . . ?
O5 C7 C2 116.8(3) . . ?
C6 C7 C2 120.4(3) . . ?
C7 C6 C5 120.2(3) . . ?
O4 C2 C3 125.5(3) . . ?
O4 C2 C7 114.9(3) . . ?
C3 C2 C7 119.6(3) . . ?
C3 C4 C5 120.1(3) . . ?
N3 C8 C5 120.4(3) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 C8 119.3(3) . . ?
C6 C5 C8 121.2(3) . . ?
N4 C9 N2 110.6(3) . . ?
C9 N4 N5 104.2(3) . . ?
N5 C10 N2 106.9(3) . . ?
C2 C3 C4 120.3(3) . . ?
O1 N1 O3 120.9(3) . . ?
O1 N1 O2 119.5(3) . . ?
O3 N1 O2 119.5(3) . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.085

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1526870'
_audit_update_record             
;
2017-01-11 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 Cl N8 O8'
_chemical_formula_weight         536.90

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.0110(16)
_cell_length_b                   11.071(2)
_cell_length_c                   13.968(3)
_cell_angle_alpha                100.75(3)
_cell_angle_beta                 91.99(3)
_cell_angle_gamma                108.46(3)
_cell_volume                     1148.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2983
_cell_measurement_theta_min      1.491
_cell_measurement_theta_max      25.378

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4560
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.491
_diffrn_reflns_theta_max         25.378
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4234
_reflns_number_gt                2983
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0941P)²+0.3820P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4234
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1712
_refine_ls_wR_factor_gt          0.1522
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_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
Cl Cl 0.36226(11) 0.97527(7) 0.78284(6) 0.0415(3) Uani 1 1 d . . . . .
O5 O 0.1779(3) 0.9083(3) 0.7668(2) 0.0772(9) Uani 1 1 d . . . . .
O6 O 0.4499(3) 0.8989(3) 0.72303(18) 0.0606(7) Uani 1 1 d . . . . .
O7 O 0.4216(4) 0.9920(3) 0.88362(18) 0.0732(8) Uani 1 1 d . . . . .
O8 O 0.4043(4) 1.0997(3) 0.7576(2) 0.0778(9) Uani 1 1 d . . . . .
O1 O -0.1486(3) 0.6599(2) 0.54836(16) 0.0480(6) Uani 1 1 d . . . . .
H1A H -0.2050 0.5829 0.5266 0.072 Uiso 1 1 calc R U . . .
O2 O -0.1424(3) 0.5004(2) 0.38253(17) 0.0507(6) Uani 1 1 d . . . . .
N1 N 0.6113(3) 1.4100(2) 0.54439(19) 0.0434(7) Uani 1 1 d . . . . .
N2 N 0.5322(4) 1.4203(2) 0.63009(19) 0.0420(7) Uani 1 1 d . . . . .
N3 N 0.4160(3) 1.2225(2) 0.55140(17) 0.0351(6) Uani 1 1 d . . . . .
N4 N 0.2999(3) 1.0941(2) 0.53523(19) 0.0399(6) Uani 1 1 d . . . . .
C1 C 0.5385(4) 1.2902(3) 0.4983(2) 0.0421(8) Uani 1 1 d . . . . .
H1C H 0.5659 1.2552 0.4374 0.051 Uiso 1 1 calc R U . . .
C2 C 0.4167(4) 1.3076(3) 0.6330(2) 0.0403(8) Uani 1 1 d . . . . .
H2B H 0.3465 1.2896 0.6836 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3032(4) 1.0185(3) 0.4560(2) 0.0399(8) Uani 1 1 d . . . . .
H3A H 0.3799 1.0489 0.4108 0.048 Uiso 1 1 calc R U . . .
C4 C 0.1868(4) 0.8835(3) 0.4355(2) 0.0368(7) Uani 1 1 d . . . . .
C5 C 0.0742(4) 0.8338(3) 0.5034(2) 0.0361(7) Uani 1 1 d . . . . .
H5B H 0.0731 0.8875 0.5629 0.043 Uiso 1 1 calc R U . . .
C6 C -0.0348(4) 0.7064(3) 0.4828(2) 0.0350(7) Uani 1 1 d . . . . .
C7 C -0.0305(4) 0.6246(3) 0.3937(2) 0.0368(7) Uani 1 1 d . . . . .
C8 C 0.0797(5) 0.6742(3) 0.3263(2) 0.0454(8) Uani 1 1 d . . . . .
H8B H 0.0808 0.6209 0.2665 0.055 Uiso 1 1 calc R U . . .
C9 C 0.1882(4) 0.8029(3) 0.3472(2) 0.0460(8) Uani 1 1 d . . . . .
H9A H 0.2626 0.8354 0.3017 0.055 Uiso 1 1 calc R U . . .
C10 C -0.1315(5) 0.4071(3) 0.2996(3) 0.0542(9) Uani 1 1 d . . . . .
H10A H -0.2170 0.3239 0.3004 0.081 Uiso 1 1 calc R U . . .
H10B H -0.1554 0.4343 0.2407 0.081 Uiso 1 1 calc R U . . .
H10C H -0.0150 0.4003 0.3019 0.081 Uiso 1 1 calc R U . . .
O3 O -0.3077(3) 0.5932(2) 0.16112(15) 0.0462(6) Uani 1 1 d . . . . .
H3B H -0.3734 0.5139 0.1478 0.055 Uiso 1 1 d R U . . .
O4 O -0.3156(3) 0.4358(2) -0.00814(16) 0.0472(6) Uani 1 1 d . . . . .
N5 N 0.4575(4) 1.3402(2) 0.1592(2) 0.0441(7) Uani 1 1 d . . . . .
N6 N 0.3748(4) 1.3504(2) 0.24351(19) 0.0450(7) Uani 1 1 d . . . . .
H6 H 0.3974 1.4198 0.2883 0.054 Uiso 1 1 calc R U . . .
N7 N 0.2586(3) 1.1532(2) 0.16346(18) 0.0346(6) Uani 1 1 d . . . . .
N8 N 0.1458(3) 1.0245(2) 0.14877(19) 0.0382(6) Uani 1 1 d . . . . .
C11 C 0.3850(4) 1.2208(3) 0.1130(2) 0.0419(8) Uani 1 1 d . . . . .
H11A H 0.4153 1.1858 0.0529 0.050 Uiso 1 1 calc R U . . .
C12 C 0.2566(4) 1.2384(3) 0.2448(2) 0.0399(7) Uani 1 1 d . . . . .
H12A H 0.1831 1.2206 0.2941 0.048 Uiso 1 1 calc R U . . .
C13 C 0.1380(4) 0.9525(3) 0.0653(2) 0.0358(7) Uani 1 1 d . . . . .
H13A H 0.2077 0.9849 0.0180 0.043 Uiso 1 1 calc R U . . .
C14 C 0.0180(4) 0.8181(3) 0.0447(2) 0.0344(7) Uani 1 1 d . . . . .
C15 C -0.0942(4) 0.7685(3) 0.1133(2) 0.0346(7) Uani 1 1 d . . . . .
H15A H -0.0956 0.8224 0.1726 0.042 Uiso 1 1 calc R U . . .
C16 C -0.2012(4) 0.6414(3) 0.0932(2) 0.0329(7) Uani 1 1 d . . . . .
C17 C -0.2014(4) 0.5597(3) 0.0029(2) 0.0353(7) Uani 1 1 d . . . . .
C18 C -0.0914(4) 0.6087(3) -0.0644(2) 0.0428(8) Uani 1 1 d . . . . .
H18A H -0.0912 0.5551 -0.1242 0.051 Uiso 1 1 calc R U . . .
C19 C 0.0191(4) 0.7372(3) -0.0436(2) 0.0410(8) Uani 1 1 d . . . . .
H19A H 0.0940 0.7692 -0.0891 0.049 Uiso 1 1 calc R U . . .
C20 C -0.3250(5) 0.3467(3) -0.0982(2) 0.0514(9) Uani 1 1 d . . . . .
H20A H -0.4096 0.2635 -0.0966 0.077 Uiso 1 1 calc R U . . .
H20B H -0.3607 0.3792 -0.1517 0.077 Uiso 1 1 calc R U . . .
H20C H -0.2109 0.3375 -0.1066 0.077 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl O5 1.415(3) . ?
Cl O8 1.425(3) . ?
Cl O7 1.429(3) . ?
Cl O6 1.435(2) . ?
O1 C6 1.367(3) . ?
O1 H1A 0.8200 . ?
O2 C7 1.359(3) . ?
O2 C10 1.425(4) . ?
N1 C1 1.296(4) . ?
N1 N2 1.377(4) . ?
N2 C2 1.306(4) . ?
N3 C2 1.335(4) . ?
N3 C1 1.367(4) . ?
N3 N4 1.402(3) . ?
N4 C3 1.264(4) . ?
C1 H1C 0.9300 . ?
C2 H2B 0.9300 . ?
C3 C4 1.457(4) . ?
C3 H3A 0.9300 . ?
C4 C9 1.384(4) . ?
C4 C5 1.399(4) . ?
C5 C6 1.373(4) . ?
C5 H5B 0.9300 . ?
C6 C7 1.405(4) . ?
C7 C8 1.383(4) . ?
C8 C9 1.383(4) . ?
C8 H8B 0.9300 . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O3 C16 1.367(3) . ?
O3 H3B 0.8499 . ?
O4 C17 1.363(3) . ?
O4 C20 1.430(4) . ?
N5 C11 1.292(4) . ?
N5 N6 1.375(4) . ?
N6 C12 1.304(4) . ?
N6 H6 0.8600 . ?
N7 C12 1.339(4) . ?
N7 C11 1.360(4) . ?
N7 N8 1.397(3) . ?
N8 C13 1.271(4) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.461(4) . ?
C13 H13A 0.9300 . ?
C14 C19 1.385(4) . ?
C14 C15 1.403(4) . ?
C15 C16 1.366(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.407(4) . ?
C17 C18 1.379(4) . ?
C18 C19 1.386(4) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
O5 Cl O8 111.0(2) . . ?
O5 Cl O7 109.60(19) . . ?
O8 Cl O7 109.13(18) . . ?
O5 Cl O6 108.41(17) . . ?
O8 Cl O6 109.20(18) . . ?
O7 Cl O6 109.44(17) . . ?
C6 O1 H1A 109.5 . . ?
C7 O2 C10 117.8(2) . . ?
C1 N1 N2 105.5(2) . . ?
C2 N2 N1 109.2(3) . . ?
C2 N3 C1 105.7(2) . . ?
C2 N3 N4 120.3(2) . . ?
C1 N3 N4 133.9(2) . . ?
C3 N4 N3 117.5(2) . . ?
N1 C1 N3 110.6(3) . . ?
N1 C1 H1C 124.7 . . ?
N3 C1 H1C 124.7 . . ?
N2 C2 N3 108.8(3) . . ?
N2 C2 H2B 125.6 . . ?
N3 C2 H2B 125.6 . . ?
N4 C3 C4 120.0(3) . . ?
N4 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C9 C4 C5 119.4(3) . . ?
C9 C4 C3 119.3(3) . . ?
C5 C4 C3 121.3(3) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5B 119.7 . . ?
C4 C5 H5B 119.7 . . ?
O1 C6 C5 120.1(3) . . ?
O1 C6 C7 120.2(3) . . ?
C5 C6 C7 119.7(3) . . ?
O2 C7 C8 126.2(3) . . ?
O2 C7 C6 114.2(3) . . ?
C8 C7 C6 119.6(3) . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 H8B 119.8 . . ?
C9 C8 H8B 119.8 . . ?
C8 C9 C4 120.4(3) . . ?
C8 C9 H9A 119.8 . . ?
C4 C9 H9A 119.8 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 O3 H3B 119.1 . . ?
C17 O4 C20 117.8(2) . . ?
C11 N5 N6 105.3(2) . . ?
C12 N6 N5 109.3(2) . . ?
C12 N6 H6 125.3 . . ?
N5 N6 H6 125.3 . . ?
C12 N7 C11 105.4(2) . . ?
C12 N7 N8 119.7(2) . . ?
C11 N7 N8 134.9(3) . . ?
C13 N8 N7 116.7(2) . . ?
N5 C11 N7 111.2(3) . . ?
N5 C11 H11A 124.4 . . ?
N7 C11 H11A 124.4 . . ?
N6 C12 N7 108.7(3) . . ?
N6 C12 H12A 125.6 . . ?
N7 C12 H12A 125.6 . . ?
N8 C13 C14 119.1(3) . . ?
N8 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C19 C14 C15 119.4(3) . . ?
C19 C14 C13 118.9(3) . . ?
C15 C14 C13 121.6(3) . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 O3 119.9(3) . . ?
C15 C16 C17 120.2(3) . . ?
O3 C16 C17 119.9(2) . . ?
O4 C17 C18 126.4(3) . . ?
O4 C17 C16 114.2(3) . . ?
C18 C17 C16 119.4(3) . . ?
C17 C18 C19 120.5(3) . . ?
C17 C18 H18A 119.8 . . ?
C19 C18 H18A 119.8 . . ?
C14 C19 C18 120.2(3) . . ?
C14 C19 H19A 119.9 . . ?
C18 C19 H19A 119.9 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C1 N1 N2 C2 0.4(4) . . . . ?
C2 N3 N4 C3 178.9(3) . . . . ?
C1 N3 N4 C3 0.8(5) . . . . ?
N2 N1 C1 N3 -0.4(4) . . . . ?
C2 N3 C1 N1 0.3(4) . . . . ?
N4 N3 C1 N1 178.6(3) . . . . ?
N1 N2 C2 N3 -0.3(4) . . . . ?
C1 N3 C2 N2 0.0(4) . . . . ?
N4 N3 C2 N2 -178.6(3) . . . . ?
N3 N4 C3 C4 179.4(3) . . . . ?
N4 C3 C4 C9 178.1(3) . . . . ?
N4 C3 C4 C5 -2.1(5) . . . . ?
C9 C4 C5 C6 -0.3(5) . . . . ?
C3 C4 C5 C6 179.9(3) . . . . ?
C4 C5 C6 O1 -177.8(3) . . . . ?
C4 C5 C6 C7 1.3(5) . . . . ?
C10 O2 C7 C8 8.3(5) . . . . ?
C10 O2 C7 C6 -172.8(3) . . . . ?
O1 C6 C7 O2 -1.8(4) . . . . ?
C5 C6 C7 O2 179.1(3) . . . . ?
O1 C6 C7 C8 177.2(3) . . . . ?
C5 C6 C7 C8 -2.0(5) . . . . ?
O2 C7 C8 C9 -179.6(3) . . . . ?
C6 C7 C8 C9 1.5(5) . . . . ?
C7 C8 C9 C4 -0.5(5) . . . . ?
C5 C4 C9 C8 -0.1(5) . . . . ?
C3 C4 C9 C8 179.6(3) . . . . ?
C11 N5 N6 C12 -0.2(4) . . . . ?
C12 N7 N8 C13 171.7(3) . . . . ?
C11 N7 N8 C13 -10.2(5) . . . . ?
N6 N5 C11 N7 0.1(4) . . . . ?
C12 N7 C11 N5 0.0(4) . . . . ?
N8 N7 C11 N5 -178.3(3) . . . . ?
N5 N6 C12 N7 0.2(4) . . . . ?
C11 N7 C12 N6 -0.1(4) . . . . ?
N8 N7 C12 N6 178.5(3) . . . . ?
N7 N8 C13 C14 -178.1(2) . . . . ?
N8 C13 C14 C19 -175.4(3) . . . . ?
N8 C13 C14 C15 2.8(5) . . . . ?
C19 C14 C15 C16 0.1(5) . . . . ?
C13 C14 C15 C16 -178.1(3) . . . . ?
C14 C15 C16 O3 178.8(3) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C20 O4 C17 C18 -0.5(5) . . . . ?
C20 O4 C17 C16 179.5(3) . . . . ?
C15 C16 C17 O4 -179.3(3) . . . . ?
O3 C16 C17 O4 1.1(4) . . . . ?
C15 C16 C17 C18 0.7(5) . . . . ?
O3 C16 C17 C18 -178.9(3) . . . . ?
O4 C17 C18 C19 -179.9(3) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C15 C14 C19 C18 0.7(5) . . . . ?
C13 C14 C19 C18 179.0(3) . . . . ?
C17 C18 C19 C14 -0.9(5) . . . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1524377'
_audit_update_record             
;
2016-12-24 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 Cl N4 O5'
_chemical_formula_weight         288.65

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                   7.1870(14)
_cell_length_b                   16.366(3)
_cell_length_c                   10.661(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.43(3)
_cell_angle_gamma                90
_cell_volume                     1248.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      8
_cell_measurement_theta_max      12

_exptl_crystal_description       'stick '
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.329
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2487
_diffrn_reflns_av_unetI/netI     0.2018
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.287
_diffrn_reflns_theta_max         25.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2298
_reflns_number_gt                967
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0671P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2298
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2150
_refine_ls_R_factor_gt           0.0904
_refine_ls_wR_factor_ref         0.2116
_refine_ls_wR_factor_gt          0.1664
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_restrained_S_all      1.057
_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 0.0201(7) 0.2687(3) 0.3435(5) 0.0388(14) Uani 1 1 d . . . . .
H1A H 0.0412 0.3094 0.3924 0.058 Uiso 1 1 d R U . . .
N1 N 0.4525(9) -0.2363(4) 0.7490(6) 0.0393(17) Uani 1 1 d . . . . .
C1 C 0.3912(10) -0.1625(5) 0.7288(8) 0.039(2) Uani 1 1 d . . . . .
H1B H 0.3592 -0.1262 0.7903 0.047 Uiso 1 1 calc R U . . .
N2 N 0.4800(9) -0.2654(4) 0.6356(6) 0.0379(17) Uani 1 1 d . . . . .
H2 H 0.5202 -0.3139 0.6230 0.045 Uiso 1 1 calc R U . . .
C2 C 0.4400(11) -0.2133(4) 0.5469(7) 0.0333(19) Uani 1 1 d . . . . .
H2B H 0.4505 -0.2209 0.4614 0.040 Uiso 1 1 calc R U . . .
N3 N 0.3811(9) -0.1468(3) 0.6014(6) 0.0320(16) Uani 1 1 d . . . . .
C3 C 0.2752(10) -0.0155(4) 0.5889(7) 0.0320(19) Uani 1 1 d . . . . .
H3A H 0.2871 -0.0164 0.6765 0.038 Uiso 1 1 calc R U . . .
N4 N 0.3190(9) -0.0776(4) 0.5302(6) 0.0376(17) Uani 1 1 d . . . . .
C4 C 0.2065(10) 0.0575(4) 0.5242(7) 0.0328(18) Uani 1 1 d . . . . .
C5 C 0.1854(10) 0.0613(4) 0.3929(7) 0.0295(18) Uani 1 1 d . . . . .
H5A H 0.2142 0.0163 0.3451 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1209(10) 0.1330(4) 0.3345(7) 0.0315(19) Uani 1 1 d . . . . .
H6A H 0.1060 0.1360 0.2470 0.038 Uiso 1 1 calc R U . . .
C7 C 0.0786(11) 0.2000(5) 0.4054(7) 0.036(2) Uani 1 1 d . . . . .
C8 C 0.0907(11) 0.1970(5) 0.5343(7) 0.037(2) Uani 1 1 d . . . . .
H8A H 0.0551 0.2412 0.5814 0.044 Uiso 1 1 calc R U . . .
C9 C 0.1599(10) 0.1237(4) 0.5935(7) 0.0291(18) Uani 1 1 d . . . . .
H9A H 0.1737 0.1206 0.6810 0.035 Uiso 1 1 calc R U . . .
Cl Cl 0.2489(3) 0.04799(12) 0.97598(18) 0.0365(6) Uani 1 1 d . . . . .
O2 O 0.3319(7) 0.0239(3) 1.1112(4) 0.0377(14) Uani 1 1 d . . . . .
O3 O 0.2072(6) -0.0313(3) 0.9008(4) 0.0377(14) Uani 1 1 d D . . . .
O4 O 0.3988(6) 0.0832(3) 0.9036(5) 0.0333(13) Uani 1 1 d . . . . .
O5 O 0.0998(7) 0.1066(3) 0.9846(5) 0.0478(16) 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 C7 1.350(8) . ?
O1 H1A 0.8501 . ?
N1 C1 1.297(9) . ?
N1 N2 1.331(7) . ?
C1 N3 1.377(9) . ?
C1 H1B 0.9300 . ?
N2 C2 1.285(9) . ?
N2 H2 0.8600 . ?
C2 N3 1.322(9) . ?
C2 H2B 0.9300 . ?
N3 N4 1.412(8) . ?
C3 N4 1.249(8) . ?
C3 C4 1.443(9) . ?
C3 H3A 0.9300 . ?
C4 C9 1.371(9) . ?
C4 C5 1.394(9) . ?
C5 C6 1.388(9) . ?
C5 H5A 0.9300 . ?
C6 C7 1.382(9) . ?
C6 H6A 0.9300 . ?
C7 C8 1.370(10) . ?
C8 C9 1.424(9) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
Cl O5 1.448(5) . ?
Cl O4 1.498(4) . ?
Cl O3 1.541(5) . ?
Cl O2 1.558(5) . ?

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
C7 O1 H1A 108.8 . . ?
C1 N1 N2 105.1(6) . . ?
N1 C1 N3 108.8(7) . . ?
N1 C1 H1B 125.6 . . ?
N3 C1 H1B 125.6 . . ?
C2 N2 N1 112.9(6) . . ?
C2 N2 H2 123.6 . . ?
N1 N2 H2 123.6 . . ?
N2 C2 N3 106.4(7) . . ?
N2 C2 H2B 126.8 . . ?
N3 C2 H2B 126.8 . . ?
C2 N3 C1 106.9(6) . . ?
C2 N3 N4 121.5(6) . . ?
C1 N3 N4 131.6(6) . . ?
N4 C3 C4 121.7(7) . . ?
N4 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C3 N4 N3 117.7(6) . . ?
C9 C4 C5 119.8(7) . . ?
C9 C4 C3 119.1(7) . . ?
C5 C4 C3 121.1(6) . . ?
C6 C5 C4 119.3(6) . . ?
C6 C5 H5A 120.4 . . ?
C4 C5 H5A 120.4 . . ?
C7 C6 C5 120.5(7) . . ?
C7 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
O1 C7 C8 120.5(7) . . ?
O1 C7 C6 117.9(7) . . ?
C8 C7 C6 121.6(7) . . ?
C7 C8 C9 117.5(7) . . ?
C7 C8 H8A 121.3 . . ?
C9 C8 H8A 121.3 . . ?
C4 C9 C8 121.3(7) . . ?
C4 C9 H9A 119.3 . . ?
C8 C9 H9A 119.3 . . ?
O5 Cl O4 110.5(3) . . ?
O5 Cl O3 118.9(3) . . ?
O4 Cl O3 99.8(3) . . ?
O5 Cl O2 109.3(3) . . ?
O4 Cl O2 110.1(3) . . ?
O3 Cl O2 107.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N1 C1 N3 0.1(8) . . . . ?
C1 N1 N2 C2 0.4(9) . . . . ?
N1 N2 C2 N3 -0.8(9) . . . . ?
N2 C2 N3 C1 0.8(9) . . . . ?
N2 C2 N3 N4 -177.8(6) . . . . ?
N1 C1 N3 C2 -0.6(9) . . . . ?
N1 C1 N3 N4 177.9(7) . . . . ?
C4 C3 N4 N3 -178.7(7) . . . . ?
C2 N3 N4 C3 -176.1(7) . . . . ?
C1 N3 N4 C3 5.6(12) . . . . ?
N4 C3 C4 C9 179.7(7) . . . . ?
N4 C3 C4 C5 0.3(12) . . . . ?
C9 C4 C5 C6 1.3(11) . . . . ?
C3 C4 C5 C6 -179.3(7) . . . . ?
C4 C5 C6 C7 0.2(11) . . . . ?
C5 C6 C7 O1 178.6(6) . . . . ?
C5 C6 C7 C8 -2.9(12) . . . . ?
O1 C7 C8 C9 -177.8(7) . . . . ?
C6 C7 C8 C9 3.8(11) . . . . ?
C5 C4 C9 C8 -0.3(11) . . . . ?
C3 C4 C9 C8 -179.7(7) . . . . ?
C7 C8 C9 C4 -2.2(11) . . . . ?

_refine_diff_density_max         0.785
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.098

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1528431'
_audit_update_record             
;
2017-01-19 deposited with the CCDC.
2017-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 N4 O5 S'
_chemical_formula_weight         301.30

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.8670(14)
_cell_length_b                   9.843(2)
_cell_length_c                   10.687(2)
_cell_angle_alpha                96.32(3)
_cell_angle_beta                 105.85(3)
_cell_angle_gamma                99.25(3)
_cell_volume                     676.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             314
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9489
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2717
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0672
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.37
_reflns_number_total             2490
_reflns_number_gt                1741
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2490
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1923
_refine_ls_wR_factor_gt          0.1696
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.62753(16) 0.88874(10) 0.75696(9) 0.0345(3) Uani 1 1 d . . .
N1 N 0.4394(6) 0.7538(3) 0.4049(3) 0.0416(9) Uani 1 1 d . . .
H1A H 0.4702 0.8306 0.4594 0.050 Uiso 1 1 calc R . .
O1 O 0.6933(5) 1.0020(3) 0.8666(3) 0.0500(9) Uani 1 1 d . . .
C1 C 0.3878(6) 0.7469(4) 0.2789(4) 0.0381(10) Uani 1 1 d . . .
H1C H 0.3781 0.8213 0.2324 0.046 Uiso 1 1 calc R . .
O2 O 0.7809(5) 0.8051(3) 0.7539(3) 0.0517(9) Uani 1 1 d . . .
N2 N 0.4398(6) 0.6257(4) 0.4421(3) 0.0448(9) Uani 1 1 d . . .
C2 C 0.3848(7) 0.5407(4) 0.3311(4) 0.0419(11) Uani 1 1 d . . .
H2C H 0.3705 0.4443 0.3234 0.050 Uiso 1 1 calc R . .
O3 O 0.4474(5) 0.7840(3) 0.7760(3) 0.0544(9) Uani 1 1 d . . .
C3 C 0.2584(6) 0.4414(4) 0.0500(4) 0.0364(10) Uani 1 1 d . . .
H3B H 0.2734 0.3803 0.1108 0.044 Uiso 1 1 calc R . .
N3 N 0.3508(5) 0.6116(3) 0.2276(3) 0.0352(8) Uani 1 1 d . . .
O4 O 0.5517(5) 0.9391(3) 0.6340(3) 0.0516(9) Uani 1 1 d . . .
N4 N 0.2907(6) 0.5700(3) 0.0898(3) 0.0381(8) Uani 1 1 d . . .
C4 C 0.1979(6) 0.3866(4) -0.0903(4) 0.0356(9) Uani 1 1 d . . .
C5 C 0.1585(7) 0.2436(4) -0.1317(4) 0.0479(12) Uani 1 1 d . . .
H5A H 0.1715 0.1837 -0.0698 0.057 Uiso 1 1 calc R . .
C6 C 0.1004(8) 0.1898(5) -0.2641(5) 0.0555(13) Uani 1 1 d . . .
H6A H 0.0746 0.0937 -0.2902 0.067 Uiso 1 1 calc R . .
C7 C 0.0799(7) 0.2752(5) -0.3580(4) 0.0488(12) Uani 1 1 d . . .
C8 C 0.1199(7) 0.4182(5) -0.3155(4) 0.0526(13) Uani 1 1 d . . .
H8A H 0.1077 0.4776 -0.3778 0.063 Uiso 1 1 calc R . .
C9 C 0.1767(7) 0.4745(5) -0.1845(4) 0.0433(11) Uani 1 1 d . . .
H9A H 0.2010 0.5706 -0.1589 0.052 Uiso 1 1 calc R . .
C10 C 0.0120(9) 0.2162(6) -0.5034(5) 0.0725(17) Uani 1 1 d . . .
H10A H -0.0090 0.1163 -0.5145 0.109 Uiso 1 1 calc R . .
H10B H 0.1168 0.2514 -0.5420 0.109 Uiso 1 1 calc R . .
H10C H -0.1147 0.2434 -0.5459 0.109 Uiso 1 1 calc R . .
OW O 0.1984(5) 0.8837(4) 0.8712(3) 0.0763(12) Uani 1 1 d . . .
HWA H 0.1220 0.8063 0.8702 0.092 Uiso 1 1 d R . .
HWB H 0.1700 0.9597 0.9003 0.092 Uiso 1 1 d R . .


_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
S O2 1.442(3) . ?
S O1 1.443(3) . ?
S O4 1.448(3) . ?
S O3 1.552(3) . ?
N1 C1 1.286(5) . ?
N1 N2 1.364(5) . ?
N1 H1A 0.8600 . ?
C1 N3 1.339(5) . ?
C1 H1C 0.9300 . ?
N2 C2 1.298(5) . ?
C2 N3 1.359(5) . ?
C2 H2C 0.9300 . ?
C3 N4 1.254(5) . ?
C3 C4 1.456(5) . ?
C3 H3B 0.9300 . ?
N3 N4 1.410(4) . ?
C4 C5 1.388(6) . ?
C4 C9 1.391(6) . ?
C5 C6 1.378(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.372(7) . ?
C6 H6A 0.9300 . ?
C7 C8 1.389(7) . ?
C7 C10 1.512(6) . ?
C8 C9 1.371(6) . ?
C8 H8A 0.9300 . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
OW HWA 0.8500 . ?
OW HWB 0.8500 . ?

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
O2 S O1 113.6(2) . . ?
O2 S O4 112.86(19) . . ?
O1 S O4 110.73(17) . . ?
O2 S O3 103.03(18) . . ?
O1 S O3 108.04(19) . . ?
O4 S O3 108.1(2) . . ?
C1 N1 N2 112.3(3) . . ?
C1 N1 H1A 123.8 . . ?
N2 N1 H1A 123.8 . . ?
N1 C1 N3 106.6(4) . . ?
N1 C1 H1C 126.7 . . ?
N3 C1 H1C 126.7 . . ?
C2 N2 N1 103.7(3) . . ?
N2 C2 N3 110.8(4) . . ?
N2 C2 H2C 124.6 . . ?
N3 C2 H2C 124.6 . . ?
N4 C3 C4 120.8(4) . . ?
N4 C3 H3B 119.6 . . ?
C4 C3 H3B 119.6 . . ?
C1 N3 C2 106.6(3) . . ?
C1 N3 N4 120.1(3) . . ?
C2 N3 N4 133.4(3) . . ?
C3 N4 N3 116.0(3) . . ?
C5 C4 C9 118.9(4) . . ?
C5 C4 C3 119.6(4) . . ?
C9 C4 C3 121.5(4) . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C7 C6 C5 121.3(4) . . ?
C7 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
C6 C7 C8 117.8(4) . . ?
C6 C7 C10 121.3(5) . . ?
C8 C7 C10 120.8(5) . . ?
C9 C8 C7 122.2(4) . . ?
C9 C8 H8A 118.9 . . ?
C7 C8 H8A 118.9 . . ?
C8 C9 C4 119.4(4) . . ?
C8 C9 H9A 120.3 . . ?
C4 C9 H9A 120.3 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
HWA OW HWB 120.0 . . ?

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
N2 N1 C1 N3 0.3(5) . . . . ?
C1 N1 N2 C2 -0.2(5) . . . . ?
N1 N2 C2 N3 0.0(5) . . . . ?
N1 C1 N3 C2 -0.3(5) . . . . ?
N1 C1 N3 N4 -179.8(3) . . . . ?
N2 C2 N3 C1 0.2(5) . . . . ?
N2 C2 N3 N4 179.7(4) . . . . ?
C4 C3 N4 N3 -179.3(3) . . . . ?
C1 N3 N4 C3 -179.8(4) . . . . ?
C2 N3 N4 C3 0.8(7) . . . . ?
N4 C3 C4 C5 -178.5(4) . . . . ?
N4 C3 C4 C9 1.0(6) . . . . ?
C9 C4 C5 C6 0.3(7) . . . . ?
C3 C4 C5 C6 179.8(4) . . . . ?
C4 C5 C6 C7 0.0(7) . . . . ?
C5 C6 C7 C8 0.1(7) . . . . ?
C5 C6 C7 C10 -178.8(4) . . . . ?
C6 C7 C8 C9 -0.5(7) . . . . ?
C10 C7 C8 C9 178.4(4) . . . . ?
C7 C8 C9 C4 0.8(7) . . . . ?
C5 C4 C9 C8 -0.7(7) . . . . ?
C3 C4 C9 C8 179.8(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.084
