# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ATCH
_database_code_depnum_ccdc_archive 'CCDC 1831245'
_audit_update_record             
;
2018-07-22 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H6 N6 O'
_chemical_formula_sum            'C3 H6 N6 O'
_chemical_formula_weight         142.14

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   5.2108(2)
_cell_length_b                   8.5731(3)
_cell_length_c                   13.2997(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.5020(10)
_cell_angle_gamma                90
_cell_volume                     587.60(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7019
_cell_measurement_theta_min      5.622
_cell_measurement_theta_max      54.999

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6102
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9651
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.097
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             1144
_reflns_number_gt                1084
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0684P)²+0.1338P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1144
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7066(2) 0.44278(12) 0.39113(8) 0.0283(3) Uani 1 1 d . . . . .
N2 N 0.3725(2) 0.40110(13) 0.27310(9) 0.0335(3) Uani 1 1 d . . . . .
N3 N 0.3397(2) 0.54973(12) 0.30512(8) 0.0342(3) Uani 1 1 d . . . . .
N4 N 0.7884(2) 0.72838(13) 0.50115(9) 0.0317(3) Uani 1 1 d . . . . .
N5 N 0.8431(2) 0.86918(14) 0.55559(10) 0.0371(3) Uani 1 1 d . . . . .
N6 N 0.6666(3) 0.19307(16) 0.30938(12) 0.0527(4) Uani 1 1 d . . . . .
O1 O 0.4369(2) 0.83028(12) 0.40711(8) 0.0486(4) Uani 1 1 d . . . . .
C1 C 0.5890(2) 0.33947(15) 0.32451(9) 0.0298(3) Uani 1 1 d . . . . .
C2 C 0.5441(2) 0.56775(14) 0.37529(9) 0.0265(3) Uani 1 1 d . . . . .
C3 C 0.5852(3) 0.71914(14) 0.42882(9) 0.0298(3) Uani 1 1 d . . . . .
H2 H 0.270(3) 0.360(2) 0.2218(14) 0.039(4) Uiso 1 1 d . . . . .
H4 H 0.899(3) 0.653(2) 0.5134(13) 0.040(4) Uiso 1 1 d . . . . .
H6A H 0.569(4) 0.135(2) 0.2679(16) 0.056(5) Uiso 1 1 d . . . . .
H6B H 0.817(4) 0.152(2) 0.3479(16) 0.059(5) Uiso 1 1 d . . . . .
H5C H 0.808(6) 0.949(4) 0.518(3) 0.110(10) Uiso 1 1 d . . . . .
H5B H 0.721(8) 0.883(5) 0.598(3) 0.144(13) 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
N1 C1 1.3360(15) . ?
N1 C2 1.3626(16) . ?
N2 C1 1.3385(17) . ?
N2 N3 1.3622(16) . ?
N2 H2 0.875(19) . ?
N3 C2 1.3175(16) . ?
N4 C3 1.3233(17) . ?
N4 N5 1.4148(15) . ?
N4 H4 0.865(19) . ?
N5 H5C 0.85(3) . ?
N5 H5B 0.92(5) . ?
N6 C1 1.3429(18) . ?
N6 H6A 0.85(2) . ?
N6 H6B 0.94(2) . ?
O1 C3 1.2341(16) . ?
C2 C3 1.4806(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 101.82(10) . . ?
C1 N2 N3 110.17(10) . . ?
C1 N2 H2 127.6(11) . . ?
N3 N2 H2 122.0(11) . . ?
C2 N3 N2 101.86(10) . . ?
C3 N4 N5 120.15(11) . . ?
C3 N4 H4 122.1(11) . . ?
N5 N4 H4 117.6(11) . . ?
N4 N5 H5C 112(2) . . ?
N4 N5 H5B 109(2) . . ?
H5C N5 H5B 99(3) . . ?
C1 N6 H6A 118.3(13) . . ?
C1 N6 H6B 121.0(13) . . ?
H6A N6 H6B 120.5(18) . . ?
N1 C1 N2 110.28(11) . . ?
N1 C1 N6 126.88(12) . . ?
N2 C1 N6 122.83(12) . . ?
N3 C2 N1 115.87(11) . . ?
N3 C2 C3 119.20(11) . . ?
N1 C2 C3 124.91(11) . . ?
O1 C3 N4 122.00(12) . . ?
O1 C3 C2 121.55(12) . . ?
N4 C3 C2 116.45(11) . . ?

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 N2 N3 C2 0.06(14) . . . . ?
C2 N1 C1 N2 0.21(14) . . . . ?
C2 N1 C1 N6 -178.90(15) . . . . ?
N3 N2 C1 N1 -0.18(15) . . . . ?
N3 N2 C1 N6 178.97(14) . . . . ?
N2 N3 C2 N1 0.08(14) . . . . ?
N2 N3 C2 C3 178.73(11) . . . . ?
C1 N1 C2 N3 -0.19(14) . . . . ?
C1 N1 C2 C3 -178.75(12) . . . . ?
N5 N4 C3 O1 -0.7(2) . . . . ?
N5 N4 C3 C2 179.51(12) . . . . ?
N3 C2 C3 O1 -2.2(2) . . . . ?
N1 C2 C3 O1 176.28(12) . . . . ?
N3 C2 C3 N4 177.52(11) . . . . ?
N1 C2 C3 N4 -3.96(19) . . . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_TNPG-ATCH
_database_code_depnum_ccdc_archive 'CCDC 1831250'
_audit_update_record             
;
2018-07-22 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 N3 O9, C3 H7 N6 O'
_chemical_formula_sum            'C9 H9 N9 O10'
_chemical_formula_weight         403.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.251(2)
_cell_length_b                   8.401(2)
_cell_length_c                   12.141(4)
_cell_angle_alpha                96.687(16)
_cell_angle_beta                 98.317(19)
_cell_angle_gamma                93.39(3)
_cell_volume                     724.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3075
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      2.85

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.169
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6664
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5609
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.709
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2656
_reflns_number_gt                2092
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0785P)²+0.1015P] 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         2656
_refine_ls_number_parameters     263
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.9405(3) 0.3670(2) 0.40640(16) 0.0311(5) Uani 1 1 d . . . . .
O2 O 0.8880(2) 0.1779(2) 0.26678(15) 0.0290(5) Uani 1 1 d . . . . .
O3 O 0.7272(3) 0.3981(2) 0.55039(15) 0.0295(5) Uani 1 1 d . . . . .
H3 H 0.820133 0.419264 0.521980 0.044 Uiso 1 1 calc R U . . .
O4 O 0.5350(3) 0.2836(2) 0.71015(15) 0.0316(5) Uani 1 1 d . . . . .
O5 O 0.2630(3) 0.3528(2) 0.64028(16) 0.0359(5) Uani 1 1 d . . . . .
O6 O 0.1657(2) 0.0765(2) 0.49250(16) 0.0272(4) Uani 1 1 d D . . . .
O7 O 0.0790(2) -0.1065(2) 0.31464(16) 0.0315(5) Uani 1 1 d . . . . .
O8 O 0.2003(3) -0.0628(3) 0.16808(16) 0.0399(6) Uani 1 1 d . . . . .
O9 O 0.5465(2) 0.0523(2) 0.20196(15) 0.0259(4) Uani 1 1 d . . . . .
N8 N 0.8333(3) 0.2550(2) 0.34664(18) 0.0212(5) Uani 1 1 d . . . . .
N7 N 0.2037(3) -0.0367(3) 0.27033(18) 0.0246(5) Uani 1 1 d . . . . .
N9 N 0.4134(3) 0.2959(2) 0.63045(17) 0.0213(5) Uani 1 1 d . . . . .
C1 C 0.6527(3) 0.2195(3) 0.3753(2) 0.0182(5) Uani 1 1 d . . . . .
C2 C 0.6140(3) 0.2880(3) 0.4815(2) 0.0197(5) Uani 1 1 d . . . . .
C3 C 0.4470(3) 0.2374(3) 0.5169(2) 0.0199(5) Uani 1 1 d . . . . .
C4 C 0.3141(3) 0.1262(3) 0.4488(2) 0.0178(5) Uani 1 1 d . . . . .
C5 C 0.3430(3) 0.0704(3) 0.3391(2) 0.0189(5) Uani 1 1 d . . . . .
C6 C 0.5176(3) 0.1096(3) 0.2965(2) 0.0172(5) Uani 1 1 d . . . . .
O10 O 0.9362(2) 0.2865(2) 0.02503(15) 0.0274(4) Uani 1 1 d . . . . .
N1 N 1.0911(3) 0.5244(3) 0.18976(19) 0.0249(5) Uani 1 1 d . . . . .
H1A H 1.121627 0.624561 0.178098 0.037 Uiso 1 1 calc R U . . .
H1B H 1.150651 0.456262 0.148310 0.037 Uiso 1 1 calc R U . . .
H1C H 1.123891 0.514307 0.261989 0.037 Uiso 1 1 calc R U . . .
N2 N 0.8959(3) 0.4894(2) 0.15936(17) 0.0208(5) Uani 1 1 d . . . . .
H2 H 0.818385 0.545834 0.191036 0.025 Uiso 1 1 calc R U . . .
N4 N 0.5128(3) 0.4027(2) 0.11660(17) 0.0209(5) Uani 1 1 d . . . . .
N5 N 0.3391(3) 0.3293(2) 0.06992(17) 0.0211(5) Uani 1 1 d . . . . .
N3 N 0.5384(3) 0.2114(2) -0.02169(18) 0.0180(5) Uani 1 1 d D . . . .
N6 N 0.2168(3) 0.1182(3) -0.07684(18) 0.0271(5) Uani 1 1 d . . . . .
H6A H 0.103282 0.127313 -0.065643 0.033 Uiso 1 1 calc R U . . .
H6B H 0.241167 0.047377 -0.128751 0.033 Uiso 1 1 calc R U . . .
C7 C 0.8355(3) 0.3664(3) 0.08007(19) 0.0184(5) Uani 1 1 d . . . . .
C14 C 0.6290(3) 0.3293(3) 0.06023(19) 0.0167(5) Uani 1 1 d . . . . .
C8 C 0.3541(3) 0.2131(3) -0.0142(2) 0.0188(5) Uani 1 1 d . . . . .
H6 H 0.109(5) 0.005(4) 0.443(3) 0.074(14) Uiso 1 1 d D . . . .
H3A H 0.577(4) 0.147(3) -0.064(2) 0.030(8) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N8 1.268(3) . ?
O2 N8 1.230(3) . ?
O3 C2 1.327(3) . ?
O3 H3 0.8200 . ?
O4 N9 1.229(3) . ?
O5 N9 1.232(3) . ?
O6 C4 1.333(3) . ?
O6 H6 0.842(19) . ?
O7 N7 1.265(3) . ?
O8 N7 1.232(3) . ?
O9 C6 1.244(3) . ?
N8 C1 1.426(3) . ?
N7 C5 1.414(3) . ?
N9 C3 1.468(3) . ?
C1 C2 1.422(3) . ?
C1 C6 1.465(3) . ?
C2 C3 1.402(3) . ?
C3 C4 1.403(3) . ?
C4 C5 1.409(3) . ?
C5 C6 1.469(3) . ?
O10 C7 1.235(3) . ?
N1 N2 1.415(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C7 1.334(3) . ?
N2 H2 0.8600 . ?
N4 C14 1.299(3) . ?
N4 N5 1.381(3) . ?
N5 C8 1.349(3) . ?
N3 C8 1.353(3) . ?
N3 C14 1.381(3) . ?
N3 H3A 0.796(18) . ?
N6 C8 1.323(3) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
C7 C14 1.490(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O3 H3 109.5 . . ?
C4 O6 H6 104(3) . . ?
O2 N8 O1 119.5(2) . . ?
O2 N8 C1 121.6(2) . . ?
O1 N8 C1 118.9(2) . . ?
O8 N7 O7 119.2(2) . . ?
O8 N7 C5 121.4(2) . . ?
O7 N7 C5 119.4(2) . . ?
O4 N9 O5 123.8(2) . . ?
O4 N9 C3 118.5(2) . . ?
O5 N9 C3 117.7(2) . . ?
C2 C1 N8 118.4(2) . . ?
C2 C1 C6 122.7(2) . . ?
N8 C1 C6 118.9(2) . . ?
O3 C2 C3 117.2(2) . . ?
O3 C2 C1 123.9(2) . . ?
C3 C2 C1 118.9(2) . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 N9 119.4(2) . . ?
C4 C3 N9 118.7(2) . . ?
O6 C4 C3 117.7(2) . . ?
O6 C4 C5 122.9(2) . . ?
C3 C4 C5 119.4(2) . . ?
C4 C5 N7 118.5(2) . . ?
C4 C5 C6 122.5(2) . . ?
N7 C5 C6 118.8(2) . . ?
O9 C6 C1 123.7(2) . . ?
O9 C6 C5 122.2(2) . . ?
C1 C6 C5 114.1(2) . . ?
N2 N1 H1A 109.5 . . ?
N2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
N2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C7 N2 N1 118.0(2) . . ?
C7 N2 H2 121.0 . . ?
N1 N2 H2 121.0 . . ?
C14 N4 N5 104.66(19) . . ?
C8 N5 N4 110.74(19) . . ?
C8 N3 C14 106.29(19) . . ?
C8 N3 H3A 122(2) . . ?
C14 N3 H3A 131(2) . . ?
C8 N6 H6A 120.0 . . ?
C8 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
O10 C7 N2 125.1(2) . . ?
O10 C7 C14 120.4(2) . . ?
N2 C7 C14 114.4(2) . . ?
N4 C14 N3 111.9(2) . . ?
N4 C14 C7 124.8(2) . . ?
N3 C14 C7 123.3(2) . . ?
N6 C8 N5 127.2(2) . . ?
N6 C8 N3 126.4(2) . . ?
N5 C8 N3 106.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N8 C1 C2 166.4(2) . . . . ?
O1 N8 C1 C2 -12.4(3) . . . . ?
O2 N8 C1 C6 -11.3(3) . . . . ?
O1 N8 C1 C6 169.9(2) . . . . ?
N8 C1 C2 O3 8.3(4) . . . . ?
C6 C1 C2 O3 -174.1(2) . . . . ?
N8 C1 C2 C3 -171.6(2) . . . . ?
C6 C1 C2 C3 6.0(4) . . . . ?
O3 C2 C3 C4 177.5(2) . . . . ?
C1 C2 C3 C4 -2.6(4) . . . . ?
O3 C2 C3 N9 -5.5(3) . . . . ?
C1 C2 C3 N9 174.4(2) . . . . ?
O4 N9 C3 C2 -51.1(3) . . . . ?
O5 N9 C3 C2 129.7(2) . . . . ?
O4 N9 C3 C4 125.9(2) . . . . ?
O5 N9 C3 C4 -53.2(3) . . . . ?
C2 C3 C4 O6 175.4(2) . . . . ?
N9 C3 C4 O6 -1.6(3) . . . . ?
C2 C3 C4 C5 -3.8(4) . . . . ?
N9 C3 C4 C5 179.2(2) . . . . ?
O6 C4 C5 N7 3.4(4) . . . . ?
C3 C4 C5 N7 -177.5(2) . . . . ?
O6 C4 C5 C6 -172.0(2) . . . . ?
C3 C4 C5 C6 7.1(4) . . . . ?
O8 N7 C5 C4 164.3(2) . . . . ?
O7 N7 C5 C4 -15.2(3) . . . . ?
O8 N7 C5 C6 -20.2(4) . . . . ?
O7 N7 C5 C6 160.3(2) . . . . ?
C2 C1 C6 O9 177.7(2) . . . . ?
N8 C1 C6 O9 -4.7(3) . . . . ?
C2 C1 C6 C5 -2.9(3) . . . . ?
N8 C1 C6 C5 174.7(2) . . . . ?
C4 C5 C6 O9 175.7(2) . . . . ?
N7 C5 C6 O9 0.3(4) . . . . ?
C4 C5 C6 C1 -3.8(3) . . . . ?
N7 C5 C6 C1 -179.1(2) . . . . ?
C14 N4 N5 C8 -0.2(3) . . . . ?
N1 N2 C7 O10 -5.3(4) . . . . ?
N1 N2 C7 C14 175.0(2) . . . . ?
N5 N4 C14 N3 0.2(3) . . . . ?
N5 N4 C14 C7 -179.9(2) . . . . ?
C8 N3 C14 N4 -0.2(3) . . . . ?
C8 N3 C14 C7 179.9(2) . . . . ?
O10 C7 C14 N4 177.4(2) . . . . ?
N2 C7 C14 N4 -2.9(3) . . . . ?
O10 C7 C14 N3 -2.8(4) . . . . ?
N2 C7 C14 N3 176.9(2) . . . . ?
N4 N5 C8 N6 179.6(2) . . . . ?
N4 N5 C8 N3 0.1(3) . . . . ?
C14 N3 C8 N6 -179.5(2) . . . . ?
C14 N3 C8 N5 0.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O1 0.82 1.78 2.498(3) 144.8 . yes
O6 H6 O7 0.842(19) 1.70(3) 2.478(3) 153(4) . yes
N6 H6B O9 0.86 2.06 2.800(3) 144.1 2_655 yes
N6 H6A O10 0.86 2.17 2.886(3) 140.7 1_455 yes

_refine_diff_density_max         0.683
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_DH-ATCH
_database_code_depnum_ccdc_archive 'CCDC 1831246'
_audit_update_record             
;
2018-07-22 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H8 N6 O, 2(Cl)'
_chemical_formula_sum            'C3 H8 Cl2 N6 O'
_chemical_formula_weight         215.05

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                   12.0906(3)
_cell_length_b                   4.70700(10)
_cell_length_c                   14.6257(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.7100(10)
_cell_angle_gamma                90
_cell_volume                     831.98(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      6.428
_cell_measurement_theta_max      55.041

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.743
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5340
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12363
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.214
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1597
_reflns_number_gt                1552
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0298P)²+0.4914P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1597
_refine_ls_number_parameters     141
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0652
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
Cl1 Cl 0.35004(3) 0.01350(7) 0.41972(2) 0.01756(13) Uani 1 1 d . . . . .
Cl2 Cl 0.10534(3) 0.79058(7) 0.58253(2) 0.01571(13) Uani 1 1 d . . . . .
N1 N 0.27940(10) 0.1139(3) 0.16799(8) 0.0127(2) Uani 1 1 d . . . . .
N2 N 0.43673(10) 0.3209(3) 0.18001(8) 0.0154(3) Uani 1 1 d D . . . .
N3 N 0.36809(10) 0.4724(3) 0.23559(8) 0.0148(3) Uani 1 1 d . . . . .
N4 N 0.17369(10) 0.6300(3) 0.32864(8) 0.0138(3) Uani 1 1 d . . . . .
N5 N 0.07605(10) 0.6952(3) 0.37577(8) 0.0135(3) Uani 1 1 d . . . . .
N6 N 0.42614(12) -0.0791(3) 0.08169(9) 0.0184(3) Uani 1 1 d . . . . .
O1 O 0.09152(8) 0.2408(2) 0.26579(7) 0.0143(2) Uani 1 1 d . . . . .
C1 C 0.38349(11) 0.1064(3) 0.13849(9) 0.0130(3) Uani 1 1 d . . . . .
C2 C 0.27453(11) 0.3393(3) 0.22656(9) 0.0117(3) Uani 1 1 d . . . . .
C3 C 0.17138(11) 0.3980(3) 0.27571(9) 0.0115(3) Uani 1 1 d . . . . .
H5C H 0.0922(16) 0.728(4) 0.4364(15) 0.029(5) Uiso 1 1 d . . . . .
H6B H 0.3879(17) -0.193(4) 0.0532(14) 0.025(5) Uiso 1 1 d . . . . .
H4 H 0.2293(17) 0.721(4) 0.3434(13) 0.024(5) Uiso 1 1 d . . . . .
H5B H 0.0434(16) 0.846(5) 0.3525(13) 0.026(5) Uiso 1 1 d . . . . .
H1 H 0.2282(17) 0.005(4) 0.1510(13) 0.024(5) Uiso 1 1 d . . . . .
H5A H 0.0301(19) 0.553(5) 0.3739(15) 0.035(6) Uiso 1 1 d . . . . .
H2 H 0.4966(13) 0.379(4) 0.1656(12) 0.023(5) Uiso 1 1 d D . . . .
H6A H 0.493(2) -0.086(5) 0.0795(15) 0.037(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3430(18) . ?
N1 C2 1.3659(18) . ?
N1 H1 0.84(2) . ?
N2 C1 1.3339(19) . ?
N2 N3 1.3777(17) . ?
N2 H2 0.808(15) . ?
N3 C2 1.2963(18) . ?
N4 C3 1.3382(18) . ?
N4 N5 1.4182(16) . ?
N4 H4 0.82(2) . ?
N5 H5C 0.91(2) . ?
N5 H5B 0.88(2) . ?
N5 H5A 0.87(2) . ?
N6 C1 1.3206(19) . ?
N6 H6B 0.82(2) . ?
N6 H6A 0.82(2) . ?
O1 C3 1.2217(17) . ?
C2 C3 1.4840(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 106.28(12) . . ?
C1 N1 H1 125.5(13) . . ?
C2 N1 H1 128.2(13) . . ?
C1 N2 N3 111.68(12) . . ?
C1 N2 H2 124.3(14) . . ?
N3 N2 H2 122.5(14) . . ?
C2 N3 N2 103.24(11) . . ?
C3 N4 N5 117.03(12) . . ?
C3 N4 H4 125.5(14) . . ?
N5 N4 H4 116.5(14) . . ?
N4 N5 H5C 110.5(12) . . ?
N4 N5 H5B 111.0(13) . . ?
H5C N5 H5B 108.7(18) . . ?
N4 N5 H5A 111.1(14) . . ?
H5C N5 H5A 106.1(18) . . ?
H5B N5 H5A 109.4(18) . . ?
C1 N6 H6B 122.1(14) . . ?
C1 N6 H6A 117.3(16) . . ?
H6B N6 H6A 120(2) . . ?
N6 C1 N2 126.49(14) . . ?
N6 C1 N1 127.36(14) . . ?
N2 C1 N1 106.13(12) . . ?
N3 C2 N1 112.66(12) . . ?
N3 C2 C3 127.17(13) . . ?
N1 C2 C3 120.07(12) . . ?
O1 C3 N4 124.45(13) . . ?
O1 C3 C2 120.15(12) . . ?
N4 C3 C2 115.39(12) . . ?

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 N2 N3 C2 0.89(15) . . . . ?
N3 N2 C1 N6 -179.38(13) . . . . ?
N3 N2 C1 N1 -0.91(15) . . . . ?
C2 N1 C1 N6 179.01(14) . . . . ?
C2 N1 C1 N2 0.56(15) . . . . ?
N2 N3 C2 N1 -0.51(15) . . . . ?
N2 N3 C2 C3 175.77(13) . . . . ?
C1 N1 C2 N3 -0.01(16) . . . . ?
C1 N1 C2 C3 -176.59(12) . . . . ?
N5 N4 C3 O1 -0.2(2) . . . . ?
N5 N4 C3 C2 179.17(11) . . . . ?
N3 C2 C3 O1 -174.13(13) . . . . ?
N1 C2 C3 O1 1.9(2) . . . . ?
N3 C2 C3 N4 6.5(2) . . . . ?
N1 C2 C3 N4 -177.47(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N6 H6A Cl1 0.82(2) 2.67(2) 3.3171(14) 137(2) 2_645 yes
N2 H2 Cl1 0.808(15) 2.352(15) 3.1338(13) 163.0(17) 2_655 yes
N5 H5A Cl2 0.87(2) 2.40(2) 3.2387(13) 161.9(19) 3_566 yes
N1 H1 Cl2 0.84(2) 2.25(2) 3.0756(13) 170.3(18) 4_565 yes
N5 H5B O1 0.88(2) 2.39(2) 2.8613(16) 113.6(16) 2 yes
N5 H5B O1 0.88(2) 2.33(2) 3.0392(17) 137.8(16) 1_565 yes
N5 H5B Cl2 0.88(2) 2.68(2) 3.3348(13) 132.8(16) 3_576 yes
N4 H4 Cl1 0.82(2) 2.28(2) 3.0676(13) 162.5(18) 1_565 yes
N6 H6B Cl1 0.82(2) 2.50(2) 3.2418(15) 152.3(18) 4 yes
N5 H5C Cl2 0.91(2) 2.16(2) 3.0671(13) 171.6(17) . yes

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_SP-ATCH
_database_code_depnum_ccdc_archive 'CCDC 1831249'
_audit_update_record             
;
2018-07-22 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H8 N6 O, O4 S'
_chemical_formula_sum            'C3 H8 N6 O5 S'
_chemical_formula_weight         240.21

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      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                   5.6170(2)
_cell_length_b                   18.6083(6)
_cell_length_c                   8.1288(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.1320(10)
_cell_angle_gamma                90
_cell_volume                     849.48(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5799
_cell_measurement_theta_min      5.470
_cell_measurement_theta_max      54.911

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.401
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6127
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12166
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_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         2.189
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1658
_reflns_number_gt                1500
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0301P)²+1.2387P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1658
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0822
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
S1 S 0.75071(9) 0.59760(3) 0.16315(7) 0.01349(19) Uani 1 1 d . . . . .
N1 N 0.5165(3) 0.26982(10) 0.4629(2) 0.0170(4) Uani 1 1 d . . . . .
N2 N 0.8136(4) 0.31049(10) 0.6056(3) 0.0181(4) Uani 1 1 d . . . . .
N3 N 0.7040(3) 0.37012(10) 0.5365(2) 0.0195(4) Uani 1 1 d . . . . .
N4 N 0.3958(4) 0.45162(10) 0.3233(2) 0.0176(4) Uani 1 1 d . . . . .
N5 N 0.2285(4) 0.49062(11) 0.2267(2) 0.0143(4) Uani 1 1 d . . . . .
N6 N 0.7547(4) 0.18404(11) 0.6060(3) 0.0186(4) Uani 1 1 d . . . . .
O1 O 0.1640(3) 0.35205(9) 0.3082(2) 0.0258(4) Uani 1 1 d . . . . .
O2 O 0.7778(3) 0.55095(9) 0.30892(19) 0.0181(4) Uani 1 1 d . . . . .
O3 O 0.5132(3) 0.58730(8) 0.0856(2) 0.0194(4) Uani 1 1 d . . . . .
O4 O 0.7745(3) 0.67419(8) 0.2134(2) 0.0208(4) Uani 1 1 d . . . . .
O5 O 0.9350(3) 0.58006(9) 0.04504(19) 0.0193(4) Uani 1 1 d . . . . .
C1 C 0.7023(4) 0.25035(13) 0.5606(3) 0.0166(5) Uani 1 1 d . . . . .
C2 C 0.5267(4) 0.34333(12) 0.4528(3) 0.0169(5) Uani 1 1 d . . . . .
C3 C 0.3444(4) 0.38273(12) 0.3549(3) 0.0176(5) Uani 1 1 d . . . . .
H2 H 0.935(5) 0.3114(14) 0.660(3) 0.017(7) Uiso 1 1 d . . . . .
H6B H 0.881(6) 0.1773(16) 0.650(4) 0.026(8) Uiso 1 1 d . . . . .
H4 H 0.531(6) 0.4730(15) 0.344(3) 0.026(7) Uiso 1 1 d . . . . .
H5A H 0.178(5) 0.4623(16) 0.147(4) 0.028(8) Uiso 1 1 d . . . . .
H5B H 0.109(5) 0.5060(15) 0.282(3) 0.021(7) Uiso 1 1 d . . . . .
H5C H 0.315(6) 0.5319(18) 0.186(4) 0.040(9) Uiso 1 1 d . . . . .
H6A H 0.698(6) 0.1548(17) 0.551(4) 0.027(8) Uiso 1 1 d . . . . .
H1 H 0.397(6) 0.2368(19) 0.409(4) 0.049(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
S1 O5 1.4626(17) . ?
S1 O2 1.4743(16) . ?
S1 O3 1.4764(16) . ?
S1 O4 1.4879(16) . ?
N1 C1 1.348(3) . ?
N1 C2 1.372(3) . ?
N1 H1 1.00(4) . ?
N2 C1 1.330(3) . ?
N2 N3 1.383(3) . ?
N2 H2 0.81(3) . ?
N3 C2 1.295(3) . ?
N4 C3 1.340(3) . ?
N4 N5 1.413(3) . ?
N4 H4 0.87(3) . ?
N5 H5A 0.88(3) . ?
N5 H5B 0.86(3) . ?
N5 H5C 0.97(3) . ?
N6 C1 1.319(3) . ?
N6 H6B 0.80(3) . ?
N6 H6A 0.77(3) . ?
O1 C3 1.217(3) . ?
C2 C3 1.479(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S1 O2 109.45(9) . . ?
O5 S1 O3 109.64(10) . . ?
O2 S1 O3 110.15(9) . . ?
O5 S1 O4 109.46(10) . . ?
O2 S1 O4 109.64(10) . . ?
O3 S1 O4 108.47(9) . . ?
C1 N1 C2 105.71(19) . . ?
C1 N1 H1 127(2) . . ?
C2 N1 H1 128(2) . . ?
C1 N2 N3 111.13(19) . . ?
C1 N2 H2 123.9(19) . . ?
N3 N2 H2 124.8(19) . . ?
C2 N3 N2 103.66(19) . . ?
C3 N4 N5 117.0(2) . . ?
C3 N4 H4 126.1(19) . . ?
N5 N4 H4 116.3(19) . . ?
N4 N5 H5A 107.8(19) . . ?
N4 N5 H5B 113.4(19) . . ?
H5A N5 H5B 110(3) . . ?
N4 N5 H5C 105.3(19) . . ?
H5A N5 H5C 112(3) . . ?
H5B N5 H5C 108(3) . . ?
C1 N6 H6B 118(2) . . ?
C1 N6 H6A 114(2) . . ?
H6B N6 H6A 120(3) . . ?
N6 C1 N2 127.5(2) . . ?
N6 C1 N1 125.6(2) . . ?
N2 C1 N1 106.9(2) . . ?
N3 C2 N1 112.6(2) . . ?
N3 C2 C3 127.5(2) . . ?
N1 C2 C3 119.8(2) . . ?
O1 C3 N4 124.7(2) . . ?
O1 C3 C2 119.9(2) . . ?
N4 C3 C2 115.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N3 C2 0.7(3) . . . . ?
N3 N2 C1 N6 -178.4(2) . . . . ?
N3 N2 C1 N1 -0.7(3) . . . . ?
C2 N1 C1 N6 178.2(2) . . . . ?
C2 N1 C1 N2 0.4(2) . . . . ?
N2 N3 C2 N1 -0.4(3) . . . . ?
N2 N3 C2 C3 178.9(2) . . . . ?
C1 N1 C2 N3 0.0(3) . . . . ?
C1 N1 C2 C3 -179.3(2) . . . . ?
N5 N4 C3 O1 -0.9(3) . . . . ?
N5 N4 C3 C2 178.50(19) . . . . ?
N3 C2 C3 O1 -166.2(2) . . . . ?
N1 C2 C3 O1 13.0(3) . . . . ?
N3 C2 C3 N4 14.3(3) . . . . ?
N1 C2 C3 N4 -166.4(2) . . . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_DN-ATCH
_database_code_depnum_ccdc_archive 'CCDC 1831247'
_audit_update_record             
;
2018-07-23 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H8 N6 O, 2(Cl)'
_chemical_formula_sum            'C6 H19 N16 O15.50'
_chemical_formula_weight         563.37

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      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                   8.1276(2)
_cell_length_b                   11.7571(3)
_cell_length_c                   12.4802(3)
_cell_angle_alpha                68.1870(10)
_cell_angle_beta                 73.4280(10)
_cell_angle_gamma                85.5050(10)
_cell_volume                     1060.68(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      5.232
_cell_measurement_theta_max      54.531

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_F_000             582
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.169
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5980
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45515
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.829
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4859
_reflns_number_gt                3901
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0850P)²+0.6571P] 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         4859
_refine_ls_number_parameters     370
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1645
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2991(2) -0.01413(15) 0.33221(14) 0.0324(4) Uani 1 1 d . . . . .
H1 H 0.277065 -0.051881 0.290389 0.039 Uiso 1 1 calc R U . . .
N2 N 0.4155(2) 0.12101(16) 0.37628(15) 0.0377(4) Uani 1 1 d . . . . .
N3 N 0.3024(2) 0.04235(16) 0.47626(15) 0.0372(4) Uani 1 1 d . . . . .
H3 H 0.279559 0.045610 0.546695 0.045 Uiso 1 1 calc R U . . .
N4 N 0.1204(3) -0.12827(17) 0.52572(16) 0.0458(5) Uani 1 1 d . . . . .
H4A H 0.084918 -0.137672 0.600416 0.055 Uiso 1 1 calc R U . . .
H4B H 0.082656 -0.176815 0.500195 0.055 Uiso 1 1 calc R U . . .
N5 N 0.6161(2) 0.23040(16) 0.13699(15) 0.0383(4) Uani 1 1 d D . . . .
H5 H 0.621043 0.258777 0.190373 0.046 Uiso 1 1 calc R U . . .
N6 N 0.7172(2) 0.28359(17) 0.01651(15) 0.0420(4) Uani 1 1 d D . . . .
H6A H 0.8142(9) 0.296(3) 0.032(3) 0.050 Uiso 0.5 1 d D U P A 1
H6B H 0.720(6) 0.2259(10) -0.0153(7) 0.050 Uiso 0.5 1 d D U P B 1
H6C H 0.665(3) 0.3554(15) -0.0063(10) 0.050 Uiso 0.5 1 d D U P C 1
H6D H 0.764(3) 0.3587(10) -0.0073(7) 0.050 Uiso 0.5 1 d D U P D 2
H6E H 0.8205(5) 0.2521(8) -0.0044(3) 0.050 Uiso 0.5 1 d D U P E 2
H6F H 0.6662(9) 0.2879(17) -0.0401(9) 0.050 Uiso 0.5 1 d D U P F 2
N7 N 0.6541(2) 0.44010(15) 0.63866(15) 0.0342(4) Uani 1 1 d . . . . .
H7 H 0.674368 0.478303 0.680665 0.041 Uiso 1 1 calc R U . . .
N8 N 0.5435(2) 0.30264(16) 0.59387(15) 0.0368(4) Uani 1 1 d . . . . .
N9 N 0.6517(2) 0.38396(16) 0.49385(15) 0.0374(4) Uani 1 1 d . . . . .
H9 H 0.673026 0.382008 0.422997 0.045 Uiso 1 1 calc R U . . .
N10 N 0.8293(3) 0.55763(17) 0.44516(17) 0.0454(5) Uani 1 1 d . . . . .
H10A H 0.864074 0.568452 0.370104 0.054 Uiso 1 1 calc R U . . .
H10B H 0.865855 0.606118 0.471310 0.054 Uiso 1 1 calc R U . . .
N11 N 0.3500(2) 0.18633(16) 0.83226(15) 0.0352(4) Uani 1 1 d . . . . .
H11 H 0.339413 0.163658 0.776432 0.042 Uiso 1 1 calc R U . . .
N12 N 0.2591(2) 0.12464(16) 0.95359(15) 0.0379(4) Uani 1 1 d . . . . .
H12A H 0.333130 0.097081 0.997453 0.057 Uiso 1 1 calc R U . . .
H12B H 0.198221 0.061813 0.959491 0.057 Uiso 1 1 calc R U . . .
H12C H 0.188720 0.176160 0.980286 0.057 Uiso 1 1 calc R U . . .
N13 N 0.7664(2) 0.45113(16) 0.19746(16) 0.0413(4) Uani 1 1 d . . . . .
N14 N 0.8804(2) 0.20591(17) 0.75947(16) 0.0403(4) Uani 1 1 d . . . . .
N15 N 0.8345(3) 0.63907(19) 0.71538(19) 0.0507(5) Uani 1 1 d . . . . .
N16 N 0.1300(2) 0.98383(15) 0.78048(14) 0.0332(4) Uani 1 1 d . . . . .
O1 O 0.5052(2) 0.08730(14) 0.09376(13) 0.0411(4) Uani 1 1 d . . . . .
O2 O 0.47205(19) 0.31869(14) 0.88225(13) 0.0404(4) Uani 1 1 d . . . . .
O3 O 0.7965(3) 0.46763(16) 0.08997(15) 0.0583(5) Uani 1 1 d D . . . .
O4 O 0.6834(3) 0.35573(16) 0.27550(15) 0.0585(5) Uani 1 1 d . . . . .
O5 O 0.8129(3) 0.52804(16) 0.22871(16) 0.0622(5) Uani 1 1 d . . . . .
O6 O 0.9288(2) 0.22508(18) 0.65090(15) 0.0559(5) Uani 1 1 d . . . . .
O7 O 0.7632(2) 0.12727(18) 0.82394(17) 0.0650(5) Uani 1 1 d . . . . .
O8 O 0.9438(3) 0.2648(2) 0.80145(18) 0.0746(6) Uani 1 1 d . . . . .
O9 O 0.7330(3) 0.5504(2) 0.7774(2) 0.0906(8) Uani 1 1 d . . . . .
O10 O 0.8978(3) 0.6572(2) 0.60878(19) 0.0790(7) Uani 1 1 d . . . . .
O11 O 0.8720(3) 0.7081(2) 0.75946(19) 0.0714(6) Uani 1 1 d . . . . .
O12 O 0.0467(2) 0.92802(16) 0.74604(15) 0.0540(5) Uani 1 1 d . . . . .
O13 O 0.0926(2) 0.97060(15) 0.88909(13) 0.0441(4) Uani 1 1 d . . . . .
O14 O 0.2549(2) 1.05388(14) 0.70709(13) 0.0421(4) Uani 1 1 d . . . . .
C1 C 0.4094(2) 0.08414(18) 0.29171(17) 0.0319(4) Uani 1 1 d . . . . .
C2 C 0.2320(2) -0.04003(18) 0.45081(17) 0.0331(4) Uani 1 1 d . . . . .
C3 C 0.5126(2) 0.13462(18) 0.16497(17) 0.0322(4) Uani 1 1 d . . . . .
C4 C 0.5475(2) 0.33945(17) 0.67920(17) 0.0322(4) Uani 1 1 d . . . . .
C5 C 0.7209(3) 0.46738(18) 0.51960(18) 0.0343(4) Uani 1 1 d . . . . .
C6 C 0.4532(2) 0.28147(17) 0.80748(17) 0.0312(4) Uani 1 1 d . . . . .
O15 O 0.9434(2) 0.70791(15) 0.97296(16) 0.0449(4) Uani 1 1 d . . . . .
H15A H 0.913(4) 0.634(3) 1.017(3) 0.054 Uiso 1 1 d . U . . .
H15B H 0.943(4) 0.706(3) 0.906(3) 0.054 Uiso 1 1 d . U . . .
O16 O 0.500000 0.500000 0.000000 0.1296(17) Uani 1 2 d DS . P . .
H16A H 0.451(2) 0.487(7) 0.0782(17) 0.155 Uiso 0.5 1 d D U P . .
H16B H 0.578(2) 0.506(2) 0.036(3) 0.155 Uiso 0.5 1 d D U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.346(2) . ?
N1 C1 1.365(2) . ?
N1 H1 0.8600 . ?
N2 C1 1.295(3) . ?
N2 N3 1.370(2) . ?
N3 C2 1.336(2) . ?
N3 H3 0.8600 . ?
N4 C2 1.310(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 C3 1.336(2) . ?
N5 N6 1.416(2) . ?
N5 H5 0.8600 . ?
N6 H6A 0.8999(10) . ?
N6 H6B 0.8999(10) . ?
N6 H6C 0.9003(10) . ?
N6 H6D 0.8999(10) . ?
N6 H6E 0.8997(10) . ?
N6 H6F 0.9003(10) . ?
N7 C5 1.349(3) . ?
N7 C4 1.368(2) . ?
N7 H7 0.8600 . ?
N8 C4 1.299(3) . ?
N8 N9 1.365(2) . ?
N9 C5 1.343(3) . ?
N9 H9 0.8600 . ?
N10 C5 1.309(3) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N11 C6 1.339(2) . ?
N11 N12 1.412(2) . ?
N11 H11 0.8600 . ?
N12 H12A 0.8900 . ?
N12 H12B 0.8900 . ?
N12 H12C 0.8900 . ?
N13 O5 1.230(2) . ?
N13 O3 1.235(2) . ?
N13 O4 1.262(2) . ?
N14 O8 1.225(2) . ?
N14 O6 1.235(2) . ?
N14 O7 1.248(2) . ?
N15 O10 1.223(3) . ?
N15 O11 1.233(2) . ?
N15 O9 1.240(3) . ?
N16 O12 1.232(2) . ?
N16 O13 1.253(2) . ?
N16 O14 1.260(2) . ?
O1 C3 1.227(2) . ?
O2 C6 1.217(2) . ?
C1 C3 1.477(3) . ?
C4 C6 1.479(3) . ?
O15 H15A 0.85(3) . ?
O15 H15B 0.84(3) . ?
O16 H16A 0.9002(10) . ?
O16 H16B 0.9002(10) . ?
O16 H16A 0.9002(11) 2_665 ?
O16 H16B 0.9003(10) 2_665 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 106.12(16) . . ?
C2 N1 H1 126.9 . . ?
C1 N1 H1 126.9 . . ?
C1 N2 N3 103.52(16) . . ?
C2 N3 N2 111.67(16) . . ?
C2 N3 H3 124.2 . . ?
N2 N3 H3 124.2 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C3 N5 N6 117.77(16) . . ?
C3 N5 H5 121.1 . . ?
N6 N5 H5 121.1 . . ?
C3 N5 H6D 140.0(3) . . ?
N6 N5 H6D 23.47(8) . . ?
H5 N5 H6D 98.4 . . ?
N5 N6 H6A 97(2) . . ?
N5 N6 H6B 105.1(11) . . ?
H6A N6 H6B 116(3) . . ?
N5 N6 H6C 99.8(6) . . ?
H6A N6 H6C 109(3) . . ?
H6B N6 H6C 124(3) . . ?
N5 N6 H6D 117.7(3) . . ?
N5 N6 H6E 117.8(3) . . ?
H6D N6 H6E 91.7(14) . . ?
N5 N6 H6F 115.9(9) . . ?
H6D N6 H6F 105.19(16) . . ?
H6E N6 H6F 105.23(16) . . ?
C5 N7 C4 106.19(16) . . ?
C5 N7 H7 126.9 . . ?
C4 N7 H7 126.9 . . ?
C4 N8 N9 103.74(16) . . ?
C5 N9 N8 111.78(17) . . ?
C5 N9 H9 124.1 . . ?
N8 N9 H9 124.1 . . ?
C5 N10 H10A 120.0 . . ?
C5 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C6 N11 N12 117.44(16) . . ?
C6 N11 H11 121.3 . . ?
N12 N11 H11 121.3 . . ?
N11 N12 H12A 109.5 . . ?
N11 N12 H12B 109.5 . . ?
H12A N12 H12B 109.5 . . ?
N11 N12 H12C 109.5 . . ?
H12A N12 H12C 109.5 . . ?
H12B N12 H12C 109.5 . . ?
O5 N13 O3 120.59(19) . . ?
O5 N13 O4 119.97(19) . . ?
O3 N13 O4 119.41(18) . . ?
O8 N14 O6 120.4(2) . . ?
O8 N14 O7 121.4(2) . . ?
O6 N14 O7 118.18(19) . . ?
O10 N15 O11 120.1(2) . . ?
O10 N15 O9 118.7(2) . . ?
O11 N15 O9 121.1(2) . . ?
O12 N16 O13 120.38(17) . . ?
O12 N16 O14 120.39(17) . . ?
O13 N16 O14 119.23(16) . . ?
N2 C1 N1 112.66(17) . . ?
N2 C1 C3 126.27(18) . . ?
N1 C1 C3 121.02(17) . . ?
N4 C2 N3 127.18(19) . . ?
N4 C2 N1 126.79(18) . . ?
N3 C2 N1 106.03(17) . . ?
O1 C3 N5 123.94(18) . . ?
O1 C3 C1 120.90(18) . . ?
N5 C3 C1 115.11(17) . . ?
N8 C4 N7 112.48(17) . . ?
N8 C4 C6 125.92(17) . . ?
N7 C4 C6 121.59(17) . . ?
N10 C5 N9 127.58(19) . . ?
N10 C5 N7 126.61(19) . . ?
N9 C5 N7 105.81(17) . . ?
O2 C6 N11 124.33(18) . . ?
O2 C6 C4 121.25(17) . . ?
N11 C6 C4 114.42(16) . . ?
H15A O15 H15B 99(3) . . ?
H16A O16 H16B 69.0(18) . . ?
H16A O16 H16A 180.0 . 2_665 ?
H16B O16 H16A 111.0(18) . 2_665 ?
H16A O16 H16B 111.0(18) . 2_665 ?
H16B O16 H16B 180.0(16) . 2_665 ?
H16A O16 H16B 69.0(18) 2_665 2_665 ?

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 N2 N3 C2 0.5(2) . . . . ?
C4 N8 N9 C5 0.7(2) . . . . ?
N3 N2 C1 N1 -0.3(2) . . . . ?
N3 N2 C1 C3 -177.45(18) . . . . ?
C2 N1 C1 N2 0.0(2) . . . . ?
C2 N1 C1 C3 177.34(17) . . . . ?
N2 N3 C2 N4 179.5(2) . . . . ?
N2 N3 C2 N1 -0.5(2) . . . . ?
C1 N1 C2 N4 -179.6(2) . . . . ?
C1 N1 C2 N3 0.3(2) . . . . ?
N6 N5 C3 O1 3.0(3) . . . . ?
N6 N5 C3 C1 -179.42(17) . . . . ?
N2 C1 C3 O1 175.0(2) . . . . ?
N1 C1 C3 O1 -2.0(3) . . . . ?
N2 C1 C3 N5 -2.7(3) . . . . ?
N1 C1 C3 N5 -179.68(17) . . . . ?
N9 N8 C4 N7 -0.4(2) . . . . ?
N9 N8 C4 C6 -179.25(18) . . . . ?
C5 N7 C4 N8 -0.1(2) . . . . ?
C5 N7 C4 C6 178.87(17) . . . . ?
N8 N9 C5 N10 179.9(2) . . . . ?
N8 N9 C5 N7 -0.7(2) . . . . ?
C4 N7 C5 N10 179.8(2) . . . . ?
C4 N7 C5 N9 0.5(2) . . . . ?
N12 N11 C6 O2 -0.8(3) . . . . ?
N12 N11 C6 C4 178.46(16) . . . . ?
N8 C4 C6 O2 176.03(19) . . . . ?
N7 C4 C6 O2 -2.8(3) . . . . ?
N8 C4 C6 N11 -3.3(3) . . . . ?
N7 C4 C6 N11 177.93(17) . . . . ?

_refine_diff_density_max         0.482
_refine_diff_density_min         -0.557
_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_DPC-ATCH
_database_code_depnum_ccdc_archive 'CCDC 1831248'
_audit_update_record             
;
2018-07-22 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(Cl O4), C3 H8 N6 O, 3(H2 O)'
_chemical_formula_sum            'C3 H14 Cl2 N6 O12'
_chemical_formula_weight         397.10

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'
Cl Cl 0.1484 0.1585 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   14.953(4)
_cell_length_b                   4.8569(12)
_cell_length_c                   19.280(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.743(6)
_cell_angle_gamma                90
_cell_volume                     1397.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    905
_cell_measurement_theta_max      22.29
_cell_measurement_theta_min      3.34

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.546
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0746 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.8574.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8214
_diffrn_reflns_av_unetI/netI     0.0814
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.672
_diffrn_reflns_theta_max         26.357
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2769
_reflns_number_gt                2061
_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_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       "'Bruker APEX2"
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0744P)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         2769
_refine_ls_number_parameters     219
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1320
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.046
_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
Cl2 Cl 0.04750(6) 0.52590(18) 0.36499(4) 0.0111(2) Uani 1 1 d . . . . .
Cl1 Cl 0.56559(6) 0.86210(19) 0.33985(4) 0.0141(2) Uani 1 1 d . . . . .
O5 O 0.27016(17) 0.8920(5) 0.30757(12) 0.0127(6) Uani 1 1 d . . . . .
O1W O 0.23783(18) 0.5883(5) 0.66546(12) 0.0138(6) Uani 1 1 d G . . . .
H1WA H 0.219050 0.421923 0.672753 0.021 Uiso 1 1 d G U . . .
H1WB H 0.293682 0.587172 0.681232 0.021 Uiso 1 1 d G U . . .
O9 O 0.04364(17) 0.7954(5) 0.33340(12) 0.0131(6) Uani 1 1 d . . . . .
O6 O 0.12221(17) 0.3737(5) 0.33808(12) 0.0149(6) Uani 1 1 d . . . . .
O4 O 0.48000(18) 0.9759(5) 0.31392(13) 0.0165(6) Uani 1 1 d . . . . .
O2W O 0.34612(18) 0.5859(5) 0.81049(14) 0.0163(6) Uani 1 1 d G . . . .
H2WA H 0.401287 0.585270 0.798701 0.025 Uiso 1 1 d G U . . .
H2WB H 0.328036 0.417022 0.804085 0.025 Uiso 1 1 d G U . . .
O7 O 0.06480(19) 0.5561(5) 0.43916(12) 0.0185(6) Uani 1 1 d . . . . .
O8 O -0.03433(18) 0.3817(6) 0.34988(14) 0.0204(6) Uani 1 1 d . . . . .
O2 O 0.56114(19) 0.5667(6) 0.33239(15) 0.0223(7) Uani 1 1 d . . . . .
O3 O 0.63604(19) 0.9690(6) 0.30175(15) 0.0222(7) Uani 1 1 d . . . . .
O1 O 0.58095(19) 0.9331(6) 0.41254(13) 0.0220(7) Uani 1 1 d . . . . .
N4 N 0.2060(2) 1.0051(6) 0.43904(14) 0.0121(7) Uani 1 1 d . . . . .
H4 H 0.185485 1.129780 0.408956 0.015 Uiso 1 1 calc R U . . .
N5 N 0.3480(2) 0.5237(6) 0.35203(14) 0.0122(7) Uani 1 1 d . . . . .
H5 H 0.363376 0.417285 0.387781 0.015 Uiso 1 1 calc R U . . .
N2 N 0.2357(2) 0.7723(6) 0.53243(14) 0.0128(7) Uani 1 1 d . . . . .
H2 H 0.236476 0.718704 0.576065 0.015 Uiso 1 1 calc R U . . .
N6 N 0.3782(2) 0.4747(6) 0.28456(14) 0.0107(7) Uani 1 1 d . . . . .
H6A H 0.421938 0.344240 0.287279 0.016 Uiso 1 1 calc R U . . .
H6B H 0.400346 0.633550 0.267484 0.016 Uiso 1 1 calc R U . . .
H6C H 0.331478 0.414929 0.255825 0.016 Uiso 1 1 calc R U . . .
N3 N 0.2842(2) 0.6473(6) 0.48279(14) 0.0129(7) Uani 1 1 d . . . . .
N1 N 0.1331(2) 1.1427(7) 0.54002(15) 0.0167(7) Uani 1 1 d . . . . .
H1A H 0.125744 1.112800 0.584312 0.020 Uiso 1 1 calc R U . . .
H1B H 0.104075 1.278071 0.518135 0.020 Uiso 1 1 calc R U . . .
C1 C 0.2948(2) 0.7423(7) 0.35723(17) 0.0102(8) Uani 1 1 d . . . . .
C2 C 0.2631(3) 0.7940(7) 0.42690(17) 0.0114(8) Uani 1 1 d . . . . .
C3 C 0.1874(3) 0.9845(7) 0.50644(17) 0.0125(8) Uani 1 1 d . . . . .
OW2A O 0.4235(3) 0.2050(11) 0.4474(2) 0.0209(10) Uani 0.525(5) 1 d DG . P A 2
H2A1 H 0.407505 0.184978 0.490372 0.031 Uiso 0.525(5) 1 d DG U P A 2
H2A2 H 0.474194 0.110316 0.446865 0.031 Uiso 0.525(5) 1 d DG U P A 2
OW2B O 0.4654(4) 0.3700(11) 0.4600(3) 0.0209(10) Uani 0.475(5) 1 d DG . P A 1
H2B1 H 0.438045 0.306775 0.496995 0.031 Uiso 0.475(5) 1 d DG U P A 1
H2B2 H 0.504832 0.209446 0.455187 0.031 Uiso 0.475(5) 1 d DG U P A 1


_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
Cl2 O8 1.423(3) . ?
Cl2 O9 1.443(3) . ?
Cl2 O7 1.444(3) . ?
Cl2 O6 1.463(3) . ?
Cl1 O3 1.421(3) . ?
Cl1 O2 1.443(3) . ?
Cl1 O1 1.447(3) . ?
Cl1 O4 1.452(3) . ?
O5 C1 1.239(4) . ?
O1W H1WA 0.8700 . ?
O1W H1WB 0.8700 . ?
O2W H2WA 0.8698 . ?
O2W H2WB 0.8700 . ?
N4 C3 1.350(4) . ?
N4 C2 1.364(5) . ?
N4 H4 0.8800 . ?
N5 C1 1.334(5) . ?
N5 N6 1.424(4) . ?
N5 H5 0.8800 . ?
N2 C3 1.337(5) . ?
N2 N3 1.379(4) . ?
N2 H2 0.8800 . ?
N6 H6A 0.9100 . ?
N6 H6B 0.9100 . ?
N6 H6C 0.9100 . ?
N3 C2 1.313(5) . ?
N1 C3 1.319(5) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
C1 C2 1.475(5) . ?
OW2A H2A1 0.8820 . ?
OW2A H2A2 0.8878 . ?
OW2B H2B1 0.9001 . ?
OW2B H2B2 0.9851 . ?

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
O8 Cl2 O9 110.46(16) . . ?
O8 Cl2 O7 110.40(16) . . ?
O9 Cl2 O7 108.99(15) . . ?
O8 Cl2 O6 110.18(16) . . ?
O9 Cl2 O6 108.62(15) . . ?
O7 Cl2 O6 108.13(16) . . ?
O3 Cl1 O2 110.04(17) . . ?
O3 Cl1 O1 109.70(17) . . ?
O2 Cl1 O1 109.68(17) . . ?
O3 Cl1 O4 110.45(17) . . ?
O2 Cl1 O4 108.07(16) . . ?
O1 Cl1 O4 108.86(16) . . ?
H1WA O1W H1WB 104.5 . . ?
H2WA O2W H2WB 104.5 . . ?
C3 N4 C2 106.3(3) . . ?
C3 N4 H4 126.9 . . ?
C2 N4 H4 126.9 . . ?
C1 N5 N6 115.3(3) . . ?
C1 N5 H5 122.3 . . ?
N6 N5 H5 122.3 . . ?
C3 N2 N3 112.0(3) . . ?
C3 N2 H2 124.0 . . ?
N3 N2 H2 124.0 . . ?
N5 N6 H6A 109.5 . . ?
N5 N6 H6B 109.5 . . ?
H6A N6 H6B 109.5 . . ?
N5 N6 H6C 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
C2 N3 N2 102.8(3) . . ?
C3 N1 H1A 120.0 . . ?
C3 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
O5 C1 N5 123.9(3) . . ?
O5 C1 C2 120.5(3) . . ?
N5 C1 C2 115.6(3) . . ?
N3 C2 N4 112.8(3) . . ?
N3 C2 C1 125.5(3) . . ?
N4 C2 C1 121.7(3) . . ?
N1 C3 N2 126.9(3) . . ?
N1 C3 N4 127.0(3) . . ?
N2 C3 N4 106.1(3) . . ?
H2A1 OW2A H2A2 103.8 . . ?
H2B1 OW2B H2B2 96.3 . . ?

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.116

