# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1055318'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C10 H6 Cl N4 O3), 3(C2 H9 N2), 2(H2 O)'
_chemical_formula_sum            'C36 H49 Cl3 N18 O11'
_chemical_formula_weight         1016.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.4057(3)
_cell_length_b                   21.2989(6)
_cell_length_c                   21.0249(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.8110(10)
_cell_angle_gamma                90
_cell_volume                     4577.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      21.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             2120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.279
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 The crystal (the largest available) diffracted quite
 weakly at high angles. On repeated recrystallisation we
 could get only small sized crystals.
 Absorption corrections were applied and all possible
 sources of error were carefuly examined and ruled out as
 causes for alert DIFMX01_ALERT_2_B. The residual electron
 density under question is close to Cl1 and could be neither
 ascertained not removed by using PLATON SQUEEZE routine.                                   
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            66617
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.152
_diffrn_reflns_theta_max         21.389
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.623
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.623
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.623
_reflns_number_total             5164
_reflns_number_gt                3794
_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    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
The hydrogen atoms bonded to N and O atoms were located from the
difference Fourier synthesis and refined isotropically.
The other hydrogen atoms were placed in calculated positions
and refined by using a riding model. Several NH and OH bonds were
restrained by means of DFIX and DANG. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1345P)²+14.0501P] 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         5164
_refine_ls_number_parameters     679
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0857
_refine_ls_wR_factor_ref         0.2558
_refine_ls_wR_factor_gt          0.2288
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.135
_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
C1 C 0.5809(8) 0.1638(3) 0.8730(3) 0.0523(19) Uani 1 1 d . . . . .
C2 C 0.6470(7) 0.1816(3) 0.8263(4) 0.061(2) Uani 1 1 d . . . . .
H2 H 0.7349 0.1924 0.8375 0.074 Uiso 1 1 calc R U . . .
C3 C 0.5873(8) 0.1838(3) 0.7646(4) 0.061(2) Uani 1 1 d . . . . .
H3 H 0.6346 0.1964 0.7334 0.073 Uiso 1 1 calc R U . . .
C4 C 0.4622(9) 0.1686(3) 0.7463(3) 0.056(2) Uani 1 1 d . . . . .
C5 C 0.3920(6) 0.1494(3) 0.7914(4) 0.064(2) Uani 1 1 d . . . . .
H5 H 0.3047 0.1380 0.7787 0.076 Uiso 1 1 calc R U . . .
C6 C 0.4528(8) 0.1468(3) 0.8577(4) 0.061(2) Uani 1 1 d . . . . .
H6 H 0.4070 0.1340 0.8893 0.073 Uiso 1 1 calc R U . . .
C7 C 0.2291(5) 0.1730(2) 0.5989(3) 0.0305(14) Uani 1 1 d . U . . .
C8 C 0.2870(6) 0.1680(3) 0.5435(3) 0.0340(14) Uani 1 1 d . . . . .
C9 C 0.0911(6) 0.1785(3) 0.5922(3) 0.0355(14) Uani 1 1 d . . . . .
C10 C 0.0674(5) 0.1691(3) 0.4751(3) 0.0346(14) Uani 1 1 d . . . . .
C11 C 0.1865(7) 0.3387(3) 0.5378(3) 0.0456(17) Uani 1 1 d . . . . .
C12 C 0.3108(7) 0.3174(3) 0.5378(3) 0.0525(18) Uani 1 1 d . . . . .
H12 H 0.3346 0.3048 0.4993 0.063 Uiso 1 1 calc R U . . .
C13 C 0.4005(6) 0.3149(3) 0.5950(3) 0.0453(16) Uani 1 1 d . . . . .
H13 H 0.4845 0.3003 0.5945 0.054 Uiso 1 1 calc R U . . .
C14 C 0.3690(6) 0.3334(3) 0.6531(2) 0.0323(14) Uani 1 1 d D . . . .
C15 C 0.2424(6) 0.3554(3) 0.6521(3) 0.0406(15) Uani 1 1 d D . . . .
H15 H 0.2184 0.3684 0.6905 0.049 Uiso 1 1 calc R U . . .
C16 C 0.1513(6) 0.3580(3) 0.5944(3) 0.0454(16) Uani 1 1 d . . . . .
H16 H 0.0671 0.3727 0.5942 0.054 Uiso 1 1 calc R U . . .
C17 C 0.5111(5) 0.3299(2) 0.8193(3) 0.0293(13) Uani 1 1 d . . . . .
C18 C 0.6508(6) 0.3342(3) 0.8276(3) 0.0345(14) Uani 1 1 d . . . . .
C19 C 0.4498(5) 0.3259(3) 0.8742(3) 0.0326(14) Uani 1 1 d . . . . .
C20 C 0.6633(6) 0.3287(3) 0.9455(3) 0.0377(15) Uani 1 1 d . . . . .
C21 C 0.7160(7) 0.5008(3) 0.9108(3) 0.0516(18) Uani 1 1 d . . . . .
C22 C 0.7463(7) 0.5148(3) 0.8515(4) 0.0567(19) Uani 1 1 d . . . . .
H22 H 0.8317 0.5251 0.8483 0.068 Uiso 1 1 calc R U . . .
C23 C 0.6490(7) 0.5135(3) 0.7966(3) 0.0486(17) Uani 1 1 d . . . . .
H23 H 0.6687 0.5223 0.7561 0.058 Uiso 1 1 calc R U . . .
C24 C 0.5225(6) 0.4989(3) 0.8025(3) 0.0395(16) Uani 1 1 d . . . . .
C25 C 0.4973(7) 0.4847(3) 0.8619(3) 0.0518(18) Uani 1 1 d . . . . .
H25 H 0.4124 0.4741 0.8658 0.062 Uiso 1 1 calc R U . . .
C26 C 0.5923(7) 0.4856(3) 0.9158(3) 0.0541(18) Uani 1 1 d . . . . .
H26 H 0.5724 0.4758 0.9559 0.065 Uiso 1 1 calc R U . . .
C27 C 0.3595(5) 0.5015(2) 0.6385(2) 0.0261(13) Uani 1 1 d . . . . .
C28 C 0.4156(5) 0.4961(2) 0.5826(3) 0.0303(14) Uani 1 1 d . . . . .
C29 C 0.2208(5) 0.5096(3) 0.6317(3) 0.0329(14) Uani 1 1 d . . . . .
C30 C 0.2021(6) 0.5070(3) 0.5145(3) 0.0347(14) Uani 1 1 d . . . . .
C31 C -0.0097(6) 0.1866(3) 0.7926(3) 0.0540(19) Uani 1 1 d . . . . .
H31A H -0.0474 0.1741 0.8295 0.065 Uiso 1 1 calc R U . . .
H31B H -0.0764 0.2096 0.7633 0.065 Uiso 1 1 calc R U . . .
C32 C 0.1034(6) 0.2312(3) 0.8164(3) 0.0504(17) Uani 1 1 d . . . . .
H32A H 0.0745 0.2640 0.8425 0.060 Uiso 1 1 calc R U . . .
H32B H 0.1738 0.2083 0.8435 0.060 Uiso 1 1 calc R U . . .
C33 C 0.0758(8) 0.4718(4) 0.8228(4) 0.069(2) Uani 1 1 d . . . . .
H33A H 0.0386 0.4500 0.8556 0.083 Uiso 1 1 calc R U . . .
H33B H 0.0035 0.4865 0.7901 0.083 Uiso 1 1 calc R U . . .
C34 C 0.1485(8) 0.5279(4) 0.8537(3) 0.064(2) Uani 1 1 d . . . . .
H34A H 0.0901 0.5530 0.8743 0.077 Uiso 1 1 calc R U . . .
H34B H 0.2200 0.5139 0.8871 0.077 Uiso 1 1 calc R U . . .
C35 C 0.8344(7) 0.3168(3) 0.6572(3) 0.0520(18) Uani 1 1 d . . . . .
H35A H 0.7802 0.2855 0.6729 0.062 Uiso 1 1 calc R U . . .
H35B H 0.8772 0.2965 0.6255 0.062 Uiso 1 1 calc R U . . .
C36 C 0.7467(6) 0.3679(3) 0.6237(3) 0.0514(18) Uani 1 1 d . . . . .
H36A H 0.7977 0.3959 0.6018 0.062 Uiso 1 1 calc R U . . .
H36B H 0.6790 0.3492 0.5912 0.062 Uiso 1 1 calc R U . . .
N1 N 0.4100(8) 0.1703(3) 0.6750(3) 0.0691(19) Uani 1 1 d . . . . .
N2 N 0.2926(6) 0.1738(2) 0.6635(3) 0.0581(17) Uani 1 1 d . . . . .
N3 N 0.2014(5) 0.1680(2) 0.4834(2) 0.0374(13) Uani 1 1 d . . . . .
N4 N 0.0182(4) 0.1749(2) 0.5294(2) 0.0379(13) Uani 1 1 d D . . . .
N5 N 0.4663(5) 0.3328(2) 0.7081(2) 0.0370(12) Uani 1 1 d D . . . .
N6 N 0.4248(4) 0.3287(2) 0.7612(2) 0.0317(12) Uani 1 1 d D . . . .
N7 N 0.7184(4) 0.3318(2) 0.8921(2) 0.0357(12) Uani 1 1 d D . . . .
N8 N 0.5301(5) 0.3258(2) 0.9348(2) 0.0374(13) Uani 1 1 d . . . . .
N9 N 0.4141(5) 0.5007(2) 0.7485(3) 0.0440(13) Uani 1 1 d . . . . .
N10 N 0.4493(5) 0.4974(2) 0.6952(2) 0.0377(12) Uani 1 1 d . . . . .
N11 N 0.3336(4) 0.4999(2) 0.5228(2) 0.0323(12) Uani 1 1 d . . . . .
N12 N 0.1505(4) 0.5117(2) 0.5688(2) 0.0351(12) Uani 1 1 d . . . . .
N31 N 0.0208(6) 0.1303(3) 0.7598(3) 0.0550(15) Uani 1 1 d D . . . .
N32 N 0.1522(5) 0.2599(3) 0.7614(3) 0.0438(13) Uani 1 1 d . . . . .
N33 N 0.1489(6) 0.4275(3) 0.7931(3) 0.0692(17) Uani 1 1 d . . . . .
N34 N 0.2019(6) 0.5677(3) 0.8071(3) 0.0487(14) Uani 1 1 d D . . . .
N35 N 0.9351(5) 0.3375(3) 0.7116(3) 0.0526(16) Uani 1 1 d . . . . .
N36 N 0.6849(5) 0.4045(3) 0.6695(3) 0.0465(14) Uani 1 1 d D . . . .
O1 O 0.4045(4) 0.1643(2) 0.54183(19) 0.0494(12) Uani 1 1 d . . . . .
O2 O 0.0295(4) 0.1862(2) 0.6366(2) 0.0553(13) Uani 1 1 d . . . . .
O1W O 0.1254(7) 0.0102(3) 0.8291(3) 0.101(2) Uani 1 1 d D . . . .
O3 O -0.0007(4) 0.1658(2) 0.42072(19) 0.0474(12) Uani 1 1 d . . . . .
O2W O 0.6547(5) 0.1631(3) 0.6217(2) 0.0756(17) Uani 1 1 d D . . . .
O4 O 0.7160(4) 0.3397(2) 0.78562(19) 0.0465(11) Uani 1 1 d . . . . .
O5 O 0.3295(4) 0.3232(2) 0.87256(18) 0.0422(11) Uani 1 1 d . . . . .
O6 O 0.7293(4) 0.3283(2) 1.00071(19) 0.0490(12) Uani 1 1 d . . . . .
O7 O 0.5353(4) 0.48856(19) 0.58266(18) 0.0405(10) Uani 1 1 d . . . . .
O8 O 0.1576(4) 0.5142(2) 0.67591(19) 0.0487(12) Uani 1 1 d . . . . .
O9 O 0.1338(4) 0.5087(2) 0.45958(19) 0.0448(11) Uani 1 1 d . . . . .
Cl1 Cl 0.6571(4) 0.16273(12) 0.95392(11) 0.1277(13) Uani 1 1 d . . . . .
Cl2 Cl 0.0716(2) 0.34243(11) 0.46687(9) 0.0863(8) Uani 1 1 d . . . . .
Cl3 Cl 0.8418(2) 0.50213(13) 0.97773(11) 0.0960(9) Uani 1 1 d . . . . .
H1A H 0.107(7) -0.002(4) 0.8679(19) 0.144 Uiso 1 1 d D U . . .
H1B H 0.2175 0.0337 0.8440 0.144 Uiso 1 1 d D U . . .
H2A H 0.692(8) 0.165(5) 0.586(3) 0.144 Uiso 1 1 d D U . . .
H2B H 0.568(3) 0.159(5) 0.619(5) 0.144 Uiso 1 1 d D U . . .
H3N H 0.242(11) 0.163(5) 0.443(5) 0.144 Uiso 1 1 d . U . . .
H4N H -0.068(2) 0.177(5) 0.525(5) 0.144 Uiso 1 1 d D U . . .
H7N H 0.806(2) 0.334(5) 0.900(5) 0.144 Uiso 1 1 d D U . . .
H8N H 0.485(11) 0.332(5) 0.971(5) 0.144 Uiso 1 1 d . U . . .
H11N H 0.369(11) 0.497(5) 0.488(6) 0.144 Uiso 1 1 d . U . . .
H12N H 0.065(11) 0.513(5) 0.557(5) 0.144 Uiso 1 1 d . U . . .
H31C H 0.053(10) 0.140(5) 0.725(3) 0.144 Uiso 1 1 d D U . . .
H31D H 0.079(11) 0.104(5) 0.789(5) 0.144 Uiso 1 1 d . U . . .
H32C H 0.180(11) 0.229(5) 0.735(5) 0.144 Uiso 1 1 d . U . . .
H32D H 0.230(11) 0.284(5) 0.775(5) 0.144 Uiso 1 1 d . U . . .
H32E H 0.077(11) 0.284(5) 0.741(5) 0.144 Uiso 1 1 d . U . . .
H33C H 0.2042 0.4076 0.8244 0.144 Uiso 1 1 d . U . . .
H33D H 0.1956 0.4487 0.7685 0.144 Uiso 1 1 d . U . . .
H34C H 0.131(11) 0.591(5) 0.779(5) 0.144 Uiso 1 1 d . U . . .
H34D H 0.257(9) 0.596(4) 0.829(4) 0.144 Uiso 1 1 d D U . . .
H34E H 0.242(11) 0.546(5) 0.784(5) 0.144 Uiso 1 1 d . U . . .
H35C H 0.921(11) 0.352(5) 0.748(6) 0.144 Uiso 1 1 d . U . . .
H35D H 0.966(11) 0.372(5) 0.701(5) 0.144 Uiso 1 1 d . U . . .
H36C H 0.742(11) 0.427(5) 0.700(5) 0.144 Uiso 1 1 d . U . . .
H36D H 0.630(8) 0.431(4) 0.645(4) 0.144 Uiso 1 1 d D U . . .
H36E H 0.643(11) 0.373(5) 0.690(5) 0.144 Uiso 1 1 d . 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
C1 C2 1.355(10) . ?
C1 C6 1.360(10) . ?
C1 Cl1 1.737(7) . ?
C2 C3 1.330(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.327(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(11) . ?
C4 N1 1.498(9) . ?
C5 C6 1.420(11) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.395(8) . ?
C7 C8 1.412(8) . ?
C7 C9 1.422(8) . ?
C8 O1 1.232(7) . ?
C8 N3 1.402(7) . ?
C9 O2 1.238(7) . ?
C9 N4 1.395(7) . ?
C10 O3 1.229(7) . ?
C10 N4 1.342(7) . ?
C10 N3 1.372(7) . ?
C11 C12 1.370(10) . ?
C11 C16 1.372(9) . ?
C11 Cl2 1.729(6) . ?
C12 C13 1.379(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.394(8) . ?
C14 N5 1.386(7) . ?
C15 C16 1.394(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N6 1.374(7) . ?
C17 C19 1.423(8) . ?
C17 C18 1.433(8) . ?
C18 O4 1.217(7) . ?
C18 N7 1.405(7) . ?
C19 O5 1.247(6) . ?
C19 N8 1.387(7) . ?
C20 O6 1.233(7) . ?
C20 N7 1.355(8) . ?
C20 N8 1.363(8) . ?
C21 C26 1.350(10) . ?
C21 C22 1.374(10) . ?
C21 Cl3 1.733(6) . ?
C22 C23 1.387(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.381(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.358(9) . ?
C24 N9 1.443(8) . ?
C25 C26 1.357(9) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 N10 1.373(7) . ?
C27 C28 1.411(8) . ?
C27 C29 1.434(8) . ?
C28 O7 1.256(7) . ?
C28 N11 1.383(7) . ?
C29 O8 1.239(7) . ?
C29 N12 1.388(7) . ?
C30 O9 1.238(7) . ?
C30 N12 1.352(7) . ?
C30 N11 1.355(7) . ?
C31 N31 1.449(9) . ?
C31 C32 1.521(9) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 N32 1.481(8) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 N33 1.427(9) . ?
C33 C34 1.497(11) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 N34 1.479(9) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 N35 1.467(9) . ?
C35 C36 1.507(9) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 N36 1.478(8) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
N1 N2 1.202(8) . ?
N3 H3N 1.01(11) . ?
N4 H4N 0.89(2) . ?
N5 N6 1.273(6) . ?
N7 H7N 0.89(2) . ?
N8 H8N 0.97(11) . ?
N9 N10 1.245(7) . ?
N11 H11N 0.89(11) . ?
N12 H12N 0.88(11) . ?
N31 H31C 0.89(2) . ?
N31 H31D 0.96(11) . ?
N32 H32C 0.95(11) . ?
N32 H32D 0.95(12) . ?
N32 H32E 0.97(12) . ?
N33 H33C 0.900 . ?
N33 H33D 0.900 . ?
N34 H34C 0.98(11) . ?
N34 H34D 0.90(2) . ?
N34 H34E 0.83(11) . ?
N35 H35C 0.87(11) . ?
N35 H35D 0.85(11) . ?
N36 H36C 0.92(11) . ?
N36 H36D 0.90(2) . ?
N36 H36E 0.95(11) . ?
O1W H1A 0.91(2) . ?
O1W H1B 1.074(7) . ?
O2W H2A 0.90(2) . ?
O2W H2B 0.90(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.7(7) . . ?
C2 C1 Cl1 120.9(6) . . ?
C6 C1 Cl1 118.4(6) . . ?
C3 C2 C1 120.6(7) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 121.8(7) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.8(6) . . ?
C3 C4 N1 115.9(7) . . ?
C5 C4 N1 124.2(8) . . ?
C4 C5 C6 119.7(6) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 117.3(7) . . ?
C1 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
N2 C7 C8 127.4(5) . . ?
N2 C7 C9 112.3(5) . . ?
C8 C7 C9 120.3(5) . . ?
O1 C8 N3 116.2(5) . . ?
O1 C8 C7 127.4(5) . . ?
N3 C8 C7 116.4(5) . . ?
O2 C9 N4 117.0(5) . . ?
O2 C9 C7 126.4(5) . . ?
N4 C9 C7 116.6(5) . . ?
O3 C10 N4 123.5(5) . . ?
O3 C10 N3 120.8(5) . . ?
N4 C10 N3 115.7(5) . . ?
C12 C11 C16 120.3(6) . . ?
C12 C11 Cl2 121.0(5) . . ?
C16 C11 Cl2 118.7(5) . . ?
C11 C12 C13 119.8(6) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 121.8(6) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 117.6(5) . . ?
C13 C14 N5 118.5(5) . . ?
C15 C14 N5 123.8(5) . . ?
C14 C15 C16 120.8(6) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 119.6(6) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
N6 C17 C19 113.7(5) . . ?
N6 C17 C18 126.1(5) . . ?
C19 C17 C18 120.2(5) . . ?
O4 C18 N7 117.2(5) . . ?
O4 C18 C17 127.4(5) . . ?
N7 C18 C17 115.4(5) . . ?
O5 C19 N8 117.0(5) . . ?
O5 C19 C17 125.5(5) . . ?
N8 C19 C17 117.5(5) . . ?
O6 C20 N7 122.2(5) . . ?
O6 C20 N8 121.6(5) . . ?
N7 C20 N8 116.2(5) . . ?
C26 C21 C22 120.5(6) . . ?
C26 C21 Cl3 121.8(6) . . ?
C22 C21 Cl3 117.8(6) . . ?
C21 C22 C23 119.7(7) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 119.3(6) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C25 C24 C23 119.0(6) . . ?
C25 C24 N9 118.2(6) . . ?
C23 C24 N9 122.7(6) . . ?
C24 C25 C26 121.9(7) . . ?
C24 C25 H25 119.1 . . ?
C26 C25 H25 119.1 . . ?
C21 C26 C25 119.7(6) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
N10 C27 C28 113.4(5) . . ?
N10 C27 C29 127.0(5) . . ?
C28 C27 C29 119.5(5) . . ?
O7 C28 N11 116.8(5) . . ?
O7 C28 C27 125.1(5) . . ?
N11 C28 C27 118.1(5) . . ?
O8 C29 N12 117.0(5) . . ?
O8 C29 C27 127.0(5) . . ?
N12 C29 C27 116.1(5) . . ?
O9 C30 N12 122.4(5) . . ?
O9 C30 N11 120.8(5) . . ?
N12 C30 N11 116.8(5) . . ?
N31 C31 C32 116.6(5) . . ?
N31 C31 H31A 108.1 . . ?
C32 C31 H31A 108.1 . . ?
N31 C31 H31B 108.1 . . ?
C32 C31 H31B 108.1 . . ?
H31A C31 H31B 107.3 . . ?
N32 C32 C31 110.9(5) . . ?
N32 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
N32 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.0 . . ?
N33 C33 C34 116.7(6) . . ?
N33 C33 H33A 108.1 . . ?
C34 C33 H33A 108.1 . . ?
N33 C33 H33B 108.1 . . ?
C34 C33 H33B 108.1 . . ?
H33A C33 H33B 107.3 . . ?
N34 C34 C33 113.1(6) . . ?
N34 C34 H34A 109.0 . . ?
C33 C34 H34A 109.0 . . ?
N34 C34 H34B 109.0 . . ?
C33 C34 H34B 109.0 . . ?
H34A C34 H34B 107.8 . . ?
N35 C35 C36 115.4(6) . . ?
N35 C35 H35A 108.4 . . ?
C36 C35 H35A 108.4 . . ?
N35 C35 H35B 108.4 . . ?
C36 C35 H35B 108.4 . . ?
H35A C35 H35B 107.5 . . ?
N36 C36 C35 112.0(5) . . ?
N36 C36 H36A 109.2 . . ?
C35 C36 H36A 109.2 . . ?
N36 C36 H36B 109.2 . . ?
C35 C36 H36B 109.2 . . ?
H36A C36 H36B 107.9 . . ?
N2 N1 C4 111.5(7) . . ?
N1 N2 C7 118.1(7) . . ?
C10 N3 C8 125.0(5) . . ?
C10 N3 H3N 118(6) . . ?
C8 N3 H3N 117(6) . . ?
C10 N4 C9 125.7(5) . . ?
C10 N4 H4N 118(7) . . ?
C9 N4 H4N 117(7) . . ?
N6 N5 C14 114.6(5) . . ?
N5 N6 C17 120.4(5) . . ?
C20 N7 C18 126.0(5) . . ?
C20 N7 H7N 114(7) . . ?
C18 N7 H7N 120(7) . . ?
C20 N8 C19 124.7(5) . . ?
C20 N8 H8N 120(7) . . ?
C19 N8 H8N 115(7) . . ?
N10 N9 C24 112.8(5) . . ?
N9 N10 C27 120.7(5) . . ?
C30 N11 C28 124.0(5) . . ?
C30 N11 H11N 118(7) . . ?
C28 N11 H11N 118(7) . . ?
C30 N12 C29 125.5(5) . . ?
C30 N12 H12N 108(7) . . ?
C29 N12 H12N 126(7) . . ?
C31 N31 H31C 110(7) . . ?
C31 N31 H31D 110(7) . . ?
H31C N31 H31D 112(9) . . ?
C32 N32 H32C 111(7) . . ?
C32 N32 H32D 113(7) . . ?
H32C N32 H32D 102(9) . . ?
C32 N32 H32E 102(6) . . ?
H32C N32 H32E 114(9) . . ?
H32D N32 H32E 115(9) . . ?
C33 N33 H33C 108.00 . . ?
C33 N33 H33D 108.00 . . ?
H33C N33 H33D 109.00 . . ?
C34 N34 H34C 110(6) . . ?
C34 N34 H34D 109(7) . . ?
H34C N34 H34D 108(9) . . ?
C34 N34 H34E 110(8) . . ?
H34C N34 H34E 109(9) . . ?
H34D N34 H34E 109(10) . . ?
C35 N35 H35C 125(8) . . ?
C35 N35 H35D 108(8) . . ?
H35C N35 H35D 93(10) . . ?
C36 N36 H36C 115(7) . . ?
C36 N36 H36D 105(7) . . ?
H36C N36 H36D 110(9) . . ?
C36 N36 H36E 103(7) . . ?
H36C N36 H36E 109(9) . . ?
H36D N36 H36E 115(9) . . ?
H1A O1W H1B 101.00 . . ?
H2A O2W H2B 122(6) . . ?

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
C3 H3 O2W 0.93 2.50 3.240(9) 136.9 .
C31 H31A Cl2 0.97 2.94 3.656(7) 131.2 4_566
C32 H32A O3 0.97 2.46 3.418(8) 171.2 4_566
C33 H33B O1W 0.97 2.66 3.569(10) 156.2 2_556
C36 H36A O9 0.97 2.58 3.513(8) 161.7 3_666
C36 H36B Cl1 0.97 2.86 3.576(7) 131.1 4_565
O1W H1A O9 0.91(2) 1.90(4) 2.758(7) 156(5) 4_566
O2W H2A O6 0.90(2) 1.91(3) 2.802(6) 167(9) 4_565
O2W H2B N1 0.90(2) 2.20(6) 2.972(8) 143(8) .
O2W H2B O1 0.90(2) 2.13(7) 2.821(6) 134(8) .
N3 H3N O5 1.01(11) 1.91(11) 2.901(6) 165(9) 4_565
N4 H4N O6 0.89(2) 2.07(3) 2.954(6) 169(10) 4_465
N7 H7N O3 0.89(2) 1.98(2) 2.872(6) 177(11) 4_666
N8 H8N O1 0.97(11) 1.85(12) 2.814(6) 175(9) 4_566
N11 H11N O7 0.89(11) 1.95(12) 2.825(6) 165(10) 3_666
N12 H12N O9 0.88(11) 2.08(12) 2.938(6) 165(10) 3_566
N31 H31C O2 0.89(2) 2.06(6) 2.867(7) 149(10) .
N31 H31D O1W 0.96(11) 2.19(11) 3.043(9) 147(9) .
N32 H32C N2 0.95(11) 2.37(11) 3.294(9) 164(9) .
N32 H32C O2 0.95(11) 2.51(11) 3.118(7) 121(8) .
N32 H32D N6 0.95(12) 2.31(12) 3.194(7) 155(9) .
N32 H32D O5 0.95(12) 2.29(11) 3.012(7) 132(9) .
N32 H32E N35 0.97(12) 1.88(12) 2.836(8) 171(10) 1_455
N33 H33C O5 0.900 2.340 3.175(7) 156.0 .
N33 H33D N9 0.900 2.630 3.448(8) 152.0 .
N33 H33D O8 0.900 2.370 3.094(7) 138.0 .
N34 H34C N31 0.98(11) 1.84(11) 2.811(8) 168(9) 2_556
N34 H34D O2W 0.90(2) 1.89(3) 2.784(8) 170(10) 2_656
N34 H34E N9 0.83(11) 2.28(11) 3.075(8) 159(11) .
N34 H34E O8 0.83(11) 2.38(11) 2.940(7) 125(10) .
N35 H35C O4 0.87(11) 2.42(12) 2.992(7) 124(10) .
N36 H36C O1W 0.92(11) 2.40(11) 2.991(8) 122(8) 2_656
N36 H36D O7 0.90(2) 1.92(3) 2.810(6) 171(10) .
N36 H36E N5 0.95(11) 2.12(11) 2.975(7) 148(9) .
N36 H36E O4 0.95(11) 2.12(11) 2.770(6) 124(8) .
C3 H3 O2W 0.93 2.50 3.240(9) 136.9 .
C31 H31A Cl2 0.97 2.94 3.656(7) 131.2 4_566
C32 H32A O3 0.97 2.46 3.418(8) 171.2 4_566
C33 H33B O1W 0.97 2.66 3.569(10) 156.2 2_556
C36 H36A O9 0.97 2.58 3.513(8) 161.7 3_666
C36 H36B Cl1 0.97 2.86 3.576(7) 131.1 4_565
O1W H1A O9 0.91(2) 1.90(4) 2.758(7) 156(5) 4_566
O2W H2A O6 0.90(2) 1.91(3) 2.802(6) 167(9) 4_565
O2W H2B N1 0.90(2) 2.20(6) 2.972(8) 143(8) .
O2W H2B O1 0.90(2) 2.13(7) 2.821(6) 134(8) .
N3 H3N O5 1.01(11) 1.91(11) 2.901(6) 165(9) 4_565
N4 H4N O6 0.89(2) 2.07(3) 2.954(6) 169(10) 4_465
N7 H7N O3 0.89(2) 1.98(2) 2.872(6) 177(11) 4_666
N8 H8N O1 0.97(11) 1.85(12) 2.814(6) 175(9) 4_566
N11 H11N O7 0.89(11) 1.95(12) 2.825(6) 165(10) 3_666
N12 H12N O9 0.88(11) 2.08(12) 2.938(6) 165(10) 3_566
N31 H31C O2 0.89(2) 2.06(6) 2.867(7) 149(10) .
N31 H31D O1W 0.96(11) 2.19(11) 3.043(9) 147(9) .
N32 H32C N2 0.95(11) 2.37(11) 3.294(9) 164(9) .
N32 H32C O2 0.95(11) 2.51(11) 3.118(7) 121(8) .
N32 H32D N6 0.95(12) 2.31(12) 3.194(7) 155(9) .
N32 H32D O5 0.95(12) 2.29(11) 3.012(7) 132(9) .
N32 H32E N35 0.97(12) 1.88(12) 2.836(8) 171(10) 1_455
N33 H33C O5 0.900 2.340 3.175(7) 156.0 .
N33 H33D N9 0.900 2.630 3.448(8) 152.0 .
N33 H33D O8 0.900 2.370 3.094(7) 138.00 .
N34 H34C N31 0.98(11) 1.84(11) 2.811(8) 168(9) 2_556
N34 H34D O2W 0.90(2) 1.89(3) 2.784(8) 170(10) 2_656
N34 H34E N9 0.83(11) 2.28(11) 3.075(8) 159(11) .
N34 H34E O8 0.83(11) 2.38(11) 2.940(7) 125(10) .
N35 H35C O4 0.87(11) 2.42(12) 2.992(7) 124(10) .
N36 H36C O1W 0.92(11) 2.40(11) 2.991(8) 122(8) 2_656
N36 H36D O7 0.90(2) 1.92(3) 2.810(6) 171(10) .
N36 H36E N5 0.95(11) 2.12(11) 2.975(7) 148(9) .
N36 H36E O4 0.95(11) 2.12(11) 2.770(6) 124(8) .

_refine_diff_density_max         1.869
_refine_diff_density_min         -1.120
_refine_diff_density_rms         0.099

_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_7
_database_code_depnum_ccdc_archive 'CCDC 1055323'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 Ag N4 O7 S'
_chemical_formula_sum            'C10 H9 Ag N4 O7 S'
_chemical_formula_weight         437.14

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 '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                   8.4530(2)
_cell_length_b                   9.1802(3)
_cell_length_c                   9.5557(3)
_cell_angle_alpha                69.666(3)
_cell_angle_beta                 69.858(2)
_cell_angle_gamma                79.279(2)
_cell_volume                     650.93(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6067
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      33.16

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.230
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.089
_exptl_absorpt_coefficient_mu    1.757
_shelx_estimated_absorpt_T_min   0.695
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_T_max  0.829
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71069
_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            11649
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.931
_diffrn_reflns_theta_max         33.221
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             4749
_reflns_number_gt                4228
_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    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0710P)²+2.4590P] 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         4749
_refine_ls_number_parameters     223
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.006
_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
C1 C 0.2061(4) 0.3826(3) 1.0143(3) 0.0073(4) Uani 1 1 d . . . . .
C2 C 0.1730(4) 0.2700(3) 0.9603(3) 0.0075(4) Uani 1 1 d . . . . .
C3 C 0.0759(4) 0.1489(4) 1.0663(4) 0.0134(5) Uani 1 1 d . . . . .
H3 H 0.0543 0.0722 1.0307 0.016 Uiso 1 1 calc R U . . .
C4 C 0.0096(5) 0.1381(4) 1.2246(4) 0.0151(6) Uani 1 1 d . . . . .
H4 H -0.0569 0.0547 1.2965 0.018 Uiso 1 1 calc R U . . .
C5 C 0.0415(4) 0.2505(4) 1.2761(4) 0.0114(5) Uani 1 1 d . . . . .
H5 H -0.0042 0.2441 1.3837 0.014 Uiso 1 1 calc R U . . .
C6 C 0.1399(4) 0.3726(3) 1.1718(3) 0.0092(5) Uani 1 1 d . . . . .
H6 H 0.1617 0.4486 1.2082 0.011 Uiso 1 1 calc R U . . .
C7 C 0.4281(4) 0.7269(3) 0.8464(3) 0.0068(4) Uani 1 1 d . . . . .
C8 C 0.5177(4) 0.7327(3) 0.6857(3) 0.0082(5) Uani 1 1 d . . . . .
C9 C 0.4476(4) 0.8478(3) 0.9054(3) 0.0074(4) Uani 1 1 d . . . . .
C10 C 0.6337(4) 0.9741(3) 0.6445(3) 0.0081(5) Uani 1 1 d . . . . .
N1 N 0.3080(3) 0.5033(3) 0.9072(3) 0.0079(4) Uani 1 1 d D . . . .
N2 N 0.3283(3) 0.6164(3) 0.9494(3) 0.0073(4) Uani 1 1 d . . . . .
N3 N 0.6118(4) 0.8580(3) 0.5938(3) 0.0089(4) Uani 1 1 d D . . . .
N4 N 0.5579(3) 0.9578(3) 0.8004(3) 0.0082(4) Uani 1 1 d D . . . .
O1 O 0.5114(4) 0.6318(3) 0.6294(3) 0.0139(4) Uani 1 1 d . . . . .
O2 O 0.3753(3) 0.8541(3) 1.0385(3) 0.0117(4) Uani 1 1 d . . . . .
O3 O 0.7163(3) 1.0835(3) 0.5537(3) 0.0132(4) Uani 1 1 d . . . . .
O10 O 0.1477(4) 0.6791(4) 0.3136(3) 0.0283(7) Uani 1 1 d D . . . .
O11 O 0.1664(3) 0.4160(3) 0.6775(3) 0.0130(4) Uani 1 1 d . . . . .
O12 O 0.2269(3) 0.1366(3) 0.7451(3) 0.0136(4) Uani 1 1 d . . . . .
O13 O 0.4339(3) 0.3030(3) 0.7210(3) 0.0110(4) Uani 1 1 d . . . . .
S1 S 0.25641(9) 0.28036(8) 0.76020(8) 0.00705(13) Uani 1 1 d . . . . .
Ag1 Ag 0.31114(4) 0.62411(3) 0.47959(3) 0.01997(10) Uani 1 1 d . . . . .
H1N H 0.373(7) 0.504(7) 0.813(4) 0.030 Uiso 1 1 d D U . . .
H3N H 0.671(7) 0.871(7) 0.494(3) 0.030 Uiso 1 1 d D U . . .
H4N H 0.572(8) 1.040(5) 0.823(7) 0.030 Uiso 1 1 d D U . . .
H10A H 0.051(5) 0.662(7) 0.290(7) 0.030 Uiso 1 1 d D U . . .
H10B H 0.223(7) 0.731(7) 0.213(4) 0.030 Uiso 1 1 d D 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
C1 C6 1.389(4) . ?
C1 N1 1.406(4) . ?
C1 C2 1.411(4) . ?
C2 C3 1.385(4) . ?
C2 S1 1.770(3) . ?
C3 C4 1.395(4) . ?
C4 C5 1.389(5) . ?
C5 C6 1.393(4) . ?
C7 N2 1.327(4) . ?
C7 C8 1.447(4) . ?
C7 C9 1.464(4) . ?
C8 O1 1.239(3) . ?
C8 N3 1.373(4) . ?
C9 O2 1.224(3) . ?
C9 N4 1.377(4) . ?
C10 O3 1.220(4) . ?
C10 N4 1.369(4) . ?
C10 N3 1.377(4) . ?
N1 N2 1.294(3) . ?
O1 Ag1 2.589(3) . ?
O3 Ag1 2.566(2) 2_676 ?
O10 Ag1 2.318(3) . ?
O11 S1 1.460(2) . ?
O11 Ag1 2.343(2) . ?
O12 S1 1.451(2) . ?
O13 S1 1.453(3) . ?
O13 Ag1 2.359(2) 2_666 ?
Ag1 O13 2.359(2) 2_666 ?
Ag1 O3 2.566(2) 2_676 ?

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
C6 C1 N1 120.7(3) . . ?
C6 C1 C2 120.1(3) . . ?
N1 C1 C2 119.2(2) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 S1 119.9(2) . . ?
C1 C2 S1 120.8(2) . . ?
C2 C3 C4 120.9(3) . . ?
C5 C4 C3 119.4(3) . . ?
C4 C5 C6 120.7(3) . . ?
C1 C6 C5 119.7(3) . . ?
N2 C7 C8 124.7(3) . . ?
N2 C7 C9 115.7(2) . . ?
C8 C7 C9 119.6(2) . . ?
O1 C8 N3 119.9(3) . . ?
O1 C8 C7 123.1(3) . . ?
N3 C8 C7 117.0(2) . . ?
O2 C9 N4 120.2(3) . . ?
O2 C9 C7 124.4(3) . . ?
N4 C9 C7 115.5(2) . . ?
O3 C10 N4 123.2(3) . . ?
O3 C10 N3 120.8(3) . . ?
N4 C10 N3 116.0(2) . . ?
N2 N1 C1 120.8(2) . . ?
N1 N2 C7 119.4(3) . . ?
C8 N3 C10 125.2(2) . . ?
C10 N4 C9 126.2(3) . . ?
C8 O1 Ag1 129.3(2) . . ?
C10 O3 Ag1 134.4(2) . 2_676 ?
S1 O11 Ag1 121.27(15) . . ?
S1 O13 Ag1 146.78(15) . 2_666 ?
O12 S1 O13 113.90(15) . . ?
O12 S1 O11 112.31(16) . . ?
O13 S1 O11 112.11(15) . . ?
O12 S1 C2 108.13(14) . . ?
O13 S1 C2 103.92(14) . . ?
O11 S1 C2 105.70(14) . . ?
O10 Ag1 O11 97.87(10) . . ?
O10 Ag1 O13 95.66(10) . 2_666 ?
O11 Ag1 O13 145.13(8) . 2_666 ?
O10 Ag1 O3 87.97(11) . 2_676 ?
O11 Ag1 O3 131.93(8) . 2_676 ?
O13 Ag1 O3 80.40(8) 2_666 2_676 ?
O10 Ag1 O1 166.13(10) . . ?
O11 Ag1 O1 94.94(8) . . ?
O13 Ag1 O1 76.54(8) 2_666 . ?
O3 Ag1 O1 79.49(8) 2_676 . ?

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
C6 H6 O10 0.95 2.61 3.541(5) 166.6 1_556
N1 H1N O1 0.88(2) 1.87(4) 2.614(3) 141(6) .
N1 H1N O13 0.88(2) 2.21(5) 2.815(3) 126(5) .
N3 H3N O12 0.89(2) 2.17(3) 3.037(3) 166(6) 2_666
N4 H4N O2 0.89(2) 2.09(3) 2.912(3) 153(6) 2_677
N4 H4N O13 0.89(2) 2.49(6) 3.058(3) 122(5) 1_565
O10 H10A O11 0.97(2) 1.98(3) 2.911(4) 160(5) 2_566
O10 H10A S1 0.97(2) 2.72(3) 3.648(3) 159(5) 2_566
O10 H10B O2 0.96(2) 1.86(2) 2.815(4) 169(6) 1_554
C6 H6 O10 0.95 2.61 3.541(5) 166.6 1_556
N1 H1N O1 0.88(2) 1.87(4) 2.614(3) 141(6) .
N1 H1N O13 0.88(2) 2.21(5) 2.815(3) 126(5) .
N3 H3N O12 0.89(2) 2.17(3) 3.037(3) 166(6) 2_666
N4 H4N O2 0.89(2) 2.09(3) 2.912(3) 153(6) 2_677
N4 H4N O13 0.89(2) 2.49(6) 3.058(3) 122(5) 1_565
O10 H10A O11 0.97(2) 1.98(3) 2.911(4) 160(5) 2_566
O10 H10A S1 0.97(2) 2.72(3) 3.648(3) 159(5) 2_566
O10 H10B O2 0.96(2) 1.86(2) 2.815(4) 169(6) 1_554

_refine_diff_density_max         1.603
_refine_diff_density_min         -1.060
_refine_diff_density_rms         0.213

_shelxl_version_number           2013-4

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

data_8
_database_code_depnum_ccdc_archive 'CCDC 1055324'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H7 N4 O6 S, C3 H5 N2, 2(H2 O)'
_chemical_formula_sum            'C13 H16 N6 O8 S'
_chemical_formula_weight         416.38

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      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                   7.1448(18)
_cell_length_b                   11.280(4)
_cell_length_c                   12.049(4)
_cell_angle_alpha                116.777(12)
_cell_angle_beta                 98.803(11)
_cell_angle_gamma                97.186(11)
_cell_volume                     835.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3316
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      25.81

_exptl_crystal_description       PRISM
_exptl_crystal_colour            GREEN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.256
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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            13696
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.055
_diffrn_reflns_theta_max         26.385
_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             3413
_reflns_number_gt                2364
_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    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.1239P)²] 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         3413
_refine_ls_number_parameters     280
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0590
_refine_ls_wR_factor_ref         0.1817
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_refine_ls_shift/su_max          0.002
_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
C1 C 0.3650(4) -0.0757(3) 0.2274(3) 0.0131(7) Uani 1 1 d . . . . .
C2 C 0.3367(5) -0.1873(4) 0.2487(3) 0.0173(8) Uani 1 1 d . . . . .
H2 H 0.3908 -0.1773 0.3303 0.021 Uiso 1 1 calc R U . . .
C3 C 0.2302(5) -0.3132(4) 0.1516(3) 0.0176(8) Uani 1 1 d . . . . .
H3A H 0.2119 -0.3891 0.1667 0.021 Uiso 1 1 calc R U . . .
C4 C 0.1503(5) -0.3280(3) 0.0321(3) 0.0178(8) Uani 1 1 d . . . . .
H4A H 0.0782 -0.4143 -0.0346 0.021 Uiso 1 1 calc R U . . .
C5 C 0.1753(5) -0.2177(3) 0.0101(3) 0.0171(7) Uani 1 1 d . . . . .
H5 H 0.1195 -0.2283 -0.0715 0.021 Uiso 1 1 calc R U . . .
C6 C 0.2826(4) -0.0902(3) 0.1076(3) 0.0133(7) Uani 1 1 d . . . . .
C7 C 0.3649(4) 0.2470(3) 0.0398(3) 0.0151(7) Uani 1 1 d . . . . .
C8 C 0.2495(4) 0.1109(3) -0.0518(3) 0.0127(7) Uani 1 1 d . . . . .
C9 C 0.1530(4) 0.0821(3) -0.1810(3) 0.0124(7) Uani 1 1 d . . . . .
C10 C 0.3029(4) 0.3152(3) -0.1256(3) 0.0131(7) Uani 1 1 d . . . . .
C11 C 0.1403(5) 0.3330(4) 0.3332(3) 0.0219(8) Uani 1 1 d . . . . .
H11A H 0.2260 0.2740 0.3291 0.026 Uiso 1 1 calc R U . . .
C12 C 0.0237(5) 0.5093(4) 0.3488(4) 0.0239(8) Uani 1 1 d . . . . .
H12 H 0.0158 0.5966 0.3578 0.029 Uiso 1 1 calc R U . . .
C13 C -0.1222(5) 0.4144(4) 0.3352(4) 0.0232(8) Uani 1 1 d . . . . .
H13 H -0.2539 0.4209 0.3325 0.028 Uiso 1 1 calc R U . . .
N1 N 0.3073(4) 0.0224(3) 0.0844(3) 0.0150(6) Uani 1 1 d . . . . .
N2 N 0.2236(3) 0.0077(3) -0.0268(3) 0.0133(6) Uani 1 1 d . . . . .
N3 N 0.1905(4) 0.1895(3) -0.2076(3) 0.0126(6) Uani 1 1 d . . . . .
N4 N 0.3818(4) 0.3401(3) -0.0042(3) 0.0157(6) Uani 1 1 d . . . . .
N11 N 0.1880(4) 0.4573(3) 0.3472(3) 0.0223(7) Uani 1 1 d . . . . .
N12 N -0.0467(4) 0.3061(3) 0.3259(3) 0.0209(7) Uani 1 1 d . . . . .
O1 O 0.4446(3) 0.2805(2) 0.1510(2) 0.0211(6) Uani 1 1 d . . . . .
O2 O 0.0477(3) -0.0264(2) -0.2615(2) 0.0165(5) Uani 1 1 d . . . . .
O1W O 1.0405(4) 0.1661(3) 0.5551(2) 0.0195(6) Uani 1 1 d . . . . .
O3 O 0.3340(3) 0.4047(2) -0.1565(2) 0.0169(5) Uani 1 1 d . . . . .
O2W O 0.5403(3) 0.5979(3) 0.3701(2) 0.0245(6) Uani 1 1 d D . . . .
O11 O 0.3620(3) 0.1468(2) 0.4271(2) 0.0234(6) Uani 1 1 d . . . . .
O12 O 0.6433(3) 0.0474(3) 0.4328(2) 0.0192(6) Uani 1 1 d . . . . .
O13 O 0.5911(3) 0.1591(3) 0.3034(2) 0.0219(6) Uani 1 1 d . . . . .
S1 S 0.50326(11) 0.08233(9) 0.35935(8) 0.0143(3) Uani 1 1 d . . . . .
H1N H 0.383(5) 0.104(4) 0.155(4) 0.021 Uiso 1 1 d . U . . .
H1W1 H 0.932(6) 0.113(4) 0.507(4) 0.021 Uiso 1 1 d . U . . .
H1W2 H 1.111(5) 0.129(4) 0.518(4) 0.021 Uiso 1 1 d . U . . .
H2W1 H 0.596(5) 0.612(4) 0.306(3) 0.021 Uiso 1 1 d D U . . .
H2W2 H 0.579(5) 0.681(2) 0.437(2) 0.021 Uiso 1 1 d D U . . .
H3N H 0.139(5) 0.182(4) -0.285(4) 0.021 Uiso 1 1 d . U . . .
H4N H 0.463(5) 0.413(4) 0.037(4) 0.021 Uiso 1 1 d . U . . .
H11N H 0.300(5) 0.497(4) 0.347(4) 0.021 Uiso 1 1 d . U . . .
H12N H -0.100(5) 0.231(4) 0.318(4) 0.021 Uiso 1 1 d . 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
C1 C2 1.391(5) . ?
C1 C6 1.399(5) . ?
C1 S1 1.791(3) . ?
C2 C3 1.387(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.381(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.401(5) . ?
C5 H5 0.9500 . ?
C6 N1 1.415(4) . ?
C7 O1 1.232(4) . ?
C7 N4 1.374(4) . ?
C7 C8 1.461(5) . ?
C8 N2 1.326(4) . ?
C8 C9 1.471(5) . ?
C9 O2 1.217(4) . ?
C9 N3 1.391(4) . ?
C10 O3 1.231(4) . ?
C10 N3 1.357(4) . ?
C10 N4 1.370(4) . ?
C11 N12 1.312(4) . ?
C11 N11 1.327(5) . ?
C11 H11A 0.9500 . ?
C12 C13 1.330(5) . ?
C12 N11 1.376(4) . ?
C12 H12 0.9500 . ?
C13 N12 1.362(5) . ?
C13 H13 0.9500 . ?
N1 N2 1.308(4) . ?
N1 H1N 0.94(4) . ?
N3 H3N 0.91(4) . ?
N4 H4N 0.83(4) . ?
N11 H11N 0.87(4) . ?
N12 H12N 0.84(4) . ?
O1W H1W1 0.85(4) . ?
O1W H1W2 0.76(4) . ?
O2W H2W1 0.98(3) . ?
O2W H2W2 0.893(19) . ?
O11 S1 1.454(2) . ?
O12 S1 1.443(2) . ?
O13 S1 1.455(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.6(3) . . ?
C2 C1 S1 117.0(3) . . ?
C6 C1 S1 123.4(3) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 N1 120.6(3) . . ?
C5 C6 N1 119.9(3) . . ?
O1 C7 N4 120.0(3) . . ?
O1 C7 C8 123.8(3) . . ?
N4 C7 C8 116.2(3) . . ?
N2 C8 C7 124.2(3) . . ?
N2 C8 C9 116.0(3) . . ?
C7 C8 C9 119.8(3) . . ?
O2 C9 N3 120.6(3) . . ?
O2 C9 C8 124.3(3) . . ?
N3 C9 C8 115.1(3) . . ?
O3 C10 N3 122.7(3) . . ?
O3 C10 N4 120.4(3) . . ?
N3 C10 N4 117.0(3) . . ?
N12 C11 N11 107.7(3) . . ?
N12 C11 H11A 126.1 . . ?
N11 C11 H11A 126.1 . . ?
C13 C12 N11 107.1(3) . . ?
C13 C12 H12 126.5 . . ?
N11 C12 H12 126.5 . . ?
C12 C13 N12 107.0(3) . . ?
C12 C13 H13 126.5 . . ?
N12 C13 H13 126.5 . . ?
N2 N1 C6 119.6(3) . . ?
N2 N1 H1N 126(2) . . ?
C6 N1 H1N 114(2) . . ?
N1 N2 C8 120.5(3) . . ?
C10 N3 C9 126.1(3) . . ?
C10 N3 H3N 112(2) . . ?
C9 N3 H3N 122(2) . . ?
C10 N4 C7 125.7(3) . . ?
C10 N4 H4N 113(3) . . ?
C7 N4 H4N 120(3) . . ?
C11 N11 C12 108.5(3) . . ?
C11 N11 H11N 126(2) . . ?
C12 N11 H11N 125(2) . . ?
C11 N12 C13 109.7(3) . . ?
C11 N12 H12N 119(2) . . ?
C13 N12 H12N 131(2) . . ?
H1W1 O1W H1W2 101(4) . . ?
H2W1 O2W H2W2 100(3) . . ?
O12 S1 O11 113.84(15) . . ?
O12 S1 O13 113.42(14) . . ?
O11 S1 O13 111.69(15) . . ?
O12 S1 C1 106.01(15) . . ?
O11 S1 C1 105.07(14) . . ?
O13 S1 C1 105.94(15) . . ?

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
C6 C1 C2 C3 1.0(4) . . . . ?
S1 C1 C2 C3 179.6(2) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
S1 C1 C6 C5 -179.5(2) . . . . ?
C2 C1 C6 N1 179.2(3) . . . . ?
S1 C1 C6 N1 0.7(4) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?
C4 C5 C6 N1 -179.9(3) . . . . ?
O1 C7 C8 N2 -2.5(5) . . . . ?
N4 C7 C8 N2 177.6(3) . . . . ?
O1 C7 C8 C9 177.4(3) . . . . ?
N4 C7 C8 C9 -2.5(4) . . . . ?
N2 C8 C9 O2 3.1(4) . . . . ?
C7 C8 C9 O2 -176.8(3) . . . . ?
N2 C8 C9 N3 -176.6(2) . . . . ?
C7 C8 C9 N3 3.5(4) . . . . ?
N11 C12 C13 N12 0.2(4) . . . . ?
C1 C6 N1 N2 -177.7(3) . . . . ?
C5 C6 N1 N2 2.5(4) . . . . ?
C6 N1 N2 C8 -178.1(3) . . . . ?
C7 C8 N2 N1 -1.7(4) . . . . ?
C9 C8 N2 N1 178.4(2) . . . . ?
O3 C10 N3 C9 178.1(3) . . . . ?
N4 C10 N3 C9 -2.2(4) . . . . ?
O2 C9 N3 C10 179.1(3) . . . . ?
C8 C9 N3 C10 -1.1(4) . . . . ?
O3 C10 N4 C7 -176.9(3) . . . . ?
N3 C10 N4 C7 3.4(5) . . . . ?
O1 C7 N4 C10 179.0(3) . . . . ?
C8 C7 N4 C10 -1.0(5) . . . . ?
N12 C11 N11 C12 0.0(4) . . . . ?
C13 C12 N11 C11 -0.1(4) . . . . ?
N11 C11 N12 C13 0.1(4) . . . . ?
C12 C13 N12 C11 -0.1(4) . . . . ?
C2 C1 S1 O12 32.1(3) . . . . ?
C6 C1 S1 O12 -149.3(3) . . . . ?
C2 C1 S1 O11 -88.7(3) . . . . ?
C6 C1 S1 O11 89.8(3) . . . . ?
C2 C1 S1 O13 152.9(2) . . . . ?
C6 C1 S1 O13 -28.5(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
C13 H13 O2W 0.95 2.54 3.325(4) 139.4 1_455
C13 H13 O1 0.95 2.55 3.240(4) 129.4 1_455
C2 H2 O12 0.95 2.62 3.400(4) 139.1 2_656
C11 H11A O11 0.95 2.43 3.260(4) 145.4 .
C12 H12 O1W 0.95 2.51 3.423(5) 161.4 2_666
N11 H11N O2W 0.87(4) 1.85(4) 2.706(4) 172(4) .
O2W H2W1 O3 0.98(3) 1.88(3) 2.842(4) 166(3) 2_665
O1W H1W1 O12 0.85(4) 2.02(4) 2.830(3) 159(4) .
N12 H12N O2 0.84(4) 2.19(4) 2.889(4) 140(3) 2
N12 H12N O13 0.84(4) 2.21(4) 2.798(4) 127(3) 1_455
O1W H1W2 O11 0.76(4) 2.27(4) 2.935(3) 146(4) 1_655
O2W H2W2 S1 0.893(19) 2.90(2) 3.706(3) 151(3) 2_666
O2W H2W2 O11 0.893(19) 1.827(19) 2.718(4) 175(3) 2_666
N4 H4N O3 0.83(4) 2.09(4) 2.911(4) 175(4) 2_665
N3 H3N O1W 0.91(4) 1.87(4) 2.776(4) 178(3) 1_454

_refine_diff_density_max         0.903
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.110

_shelxl_version_number           2013-4

