# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_n150713b
_database_code_depnum_ccdc_archive 'CCDC 1439107'
_audit_update_record             
;
2015-11-26 deposited with the CCDC.
2016-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 Ag2 N10 O6.25'
_chemical_formula_weight         692.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   22.5787(12)
_cell_length_b                   9.4591(6)
_cell_length_c                   12.7032(8)
_cell_angle_alpha                90
_cell_angle_beta                 118.015(3)
_cell_angle_gamma                90
_cell_volume                     2395.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2355
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      28.18

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   0.677
_exptl_transmission_factor_max   0.718
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.693
_shelx_estimated_absorpt_T_min   0.677
_shelx_estimated_absorpt_T_max   0.718
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8668
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.043
_diffrn_reflns_theta_max         28.272
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2966
_reflns_number_gt                2495
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0258P)²+0.5822P] 
 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         2966
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0640
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
O1 O 0.30053(9) 0.4883(2) 0.72571(16) 0.0159(4) Uani 1 1 d . . . . .
Ag1 Ag 0.17262(2) 0.57591(2) 0.65668(2) 0.01466(7) Uani 1 1 d . . . . .
N1 N 0.16502(11) 0.4605(2) 0.4962(2) 0.0133(5) Uani 1 1 d . . . . .
N2 N 0.17283(11) 0.4134(2) 0.3301(2) 0.0137(5) Uani 1 1 d . . . . .
N3 N 0.16345(11) 0.3181(2) 0.47780(19) 0.0111(5) Uani 1 1 d . . . . .
N4 N -0.12412(11) 0.1985(2) 0.4372(2) 0.0151(5) Uani 1 1 d . . . . .
H4A H -0.1463 0.1165 0.3850 0.018 Uiso 1 1 d R U . . .
H4B H -0.1252 0.1871 0.5137 0.018 Uiso 1 1 d R U . . .
C1 C 0.17074(13) 0.5131(3) 0.4055(2) 0.0142(6) Uani 1 1 d . . . . .
H1 H 0.1732 0.6117 0.3938 0.017 Uiso 1 1 calc R U . . .
C2 C 0.16787(13) 0.2925(3) 0.3794(2) 0.0131(6) Uani 1 1 d . . . . .
H2 H 0.1676 0.2010 0.3482 0.016 Uiso 1 1 calc R U . . .
C3 C 0.15387(13) 0.2173(3) 0.5568(2) 0.0131(6) Uani 1 1 d . . . . .
H3A H 0.1814 0.2469 0.6408 0.016 Uiso 1 1 calc R U . . .
H3B H 0.1693 0.1224 0.5473 0.016 Uiso 1 1 calc R U . . .
C4 C 0.08087(13) 0.2095(3) 0.5284(2) 0.0121(5) Uani 1 1 d . . . . .
C5 C 0.05829(14) 0.2700(3) 0.6018(2) 0.0165(6) Uani 1 1 d . . . . .
H5 H 0.0894 0.3156 0.6731 0.020 Uiso 1 1 calc R U . . .
C6 C -0.00888(13) 0.2654(3) 0.5734(2) 0.0164(6) Uani 1 1 d . . . . .
H6 H -0.0236 0.3081 0.6248 0.020 Uiso 1 1 calc R U . . .
C7 C -0.05483(13) 0.1981(3) 0.4692(2) 0.0127(6) Uani 1 1 d . . . . .
C8 C -0.03231(13) 0.1366(3) 0.3956(2) 0.0138(6) Uani 1 1 d . . . . .
H8 H -0.0632 0.0901 0.3247 0.017 Uiso 1 1 calc R U . . .
C9 C 0.03471(13) 0.1425(3) 0.4245(2) 0.0140(6) Uani 1 1 d . . . . .
H9 H 0.0495 0.1003 0.3730 0.017 Uiso 1 1 calc R U . . .
O2 O 0.28173(9) 0.6988(2) 0.64922(17) 0.0179(4) Uani 1 1 d . . . . .
O3 O 0.35464(10) 0.5626(2) 0.63309(19) 0.0246(5) Uani 1 1 d . . . . .
N9 N 0.31271(11) 0.5842(2) 0.6689(2) 0.0134(5) Uani 1 1 d . . . . .
O7 O 0.0000 0.4413(15) 0.2500 0.046(4) Uani 0.25 2 d S T 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
O1 N9 1.267(3) . ?
O1 Ag1 2.7235(19) . ?
Ag1 N2 2.203(2) 6_566 ?
Ag1 N1 2.247(2) . ?
Ag1 N4 2.439(2) 5_566 ?
N1 C1 1.316(3) . ?
N1 N3 1.365(3) . ?
N2 C2 1.334(3) . ?
N2 C1 1.361(3) . ?
N2 Ag1 2.203(2) 6_565 ?
N3 C2 1.322(3) . ?
N3 C3 1.472(3) . ?
N4 C7 1.420(3) . ?
N4 Ag1 2.439(2) 5_566 ?
N4 H4A 0.9899 . ?
N4 H4B 0.9902 . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C3 C4 1.514(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.380(4) . ?
C4 C9 1.392(4) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(4) . ?
C8 C9 1.381(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O2 N9 1.250(3) . ?
O3 N9 1.245(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
N9 O1 Ag1 94.58(14) . . ?
N2 Ag1 N1 153.24(8) 6_566 . ?
N2 Ag1 N4 103.80(8) 6_566 5_566 ?
N1 Ag1 N4 98.98(8) . 5_566 ?
N2 Ag1 O1 100.84(7) 6_566 . ?
N1 Ag1 O1 76.22(7) . . ?
N4 Ag1 O1 126.04(7) 5_566 . ?
C1 N1 N3 103.2(2) . . ?
C1 N1 Ag1 127.85(19) . . ?
N3 N1 Ag1 128.31(17) . . ?
C2 N2 C1 103.1(2) . . ?
C2 N2 Ag1 123.17(18) . 6_565 ?
C1 N2 Ag1 133.44(19) . 6_565 ?
C2 N3 N1 109.6(2) . . ?
C2 N3 C3 128.8(2) . . ?
N1 N3 C3 121.5(2) . . ?
C7 N4 Ag1 108.91(16) . 5_566 ?
C7 N4 H4A 109.4 . . ?
Ag1 N4 H4A 112.9 5_566 . ?
C7 N4 H4B 104.6 . . ?
Ag1 N4 H4B 111.3 5_566 . ?
H4A N4 H4B 109.5 . . ?
N1 C1 N2 113.8(3) . . ?
N1 C1 H1 123.1 . . ?
N2 C1 H1 123.1 . . ?
N3 C2 N2 110.3(2) . . ?
N3 C2 H2 124.9 . . ?
N2 C2 H2 124.9 . . ?
N3 C3 C4 111.1(2) . . ?
N3 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N3 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C9 118.7(2) . . ?
C5 C4 C3 121.7(2) . . ?
C9 C4 C3 119.6(2) . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 119.2(3) . . ?
C8 C7 N4 120.9(2) . . ?
C6 C7 N4 119.9(3) . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C4 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
O3 N9 O2 121.3(2) . . ?
O3 N9 O1 119.8(2) . . ?
O2 N9 O1 118.9(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 N1 N3 C2 -0.3(3) . . . . ?
Ag1 N1 N3 C2 -171.58(17) . . . . ?
C1 N1 N3 C3 -176.9(2) . . . . ?
Ag1 N1 N3 C3 11.8(3) . . . . ?
N3 N1 C1 N2 0.1(3) . . . . ?
Ag1 N1 C1 N2 171.46(17) . . . . ?
C2 N2 C1 N1 0.1(3) . . . . ?
Ag1 N2 C1 N1 173.52(18) 6_565 . . . ?
N1 N3 C2 N2 0.4(3) . . . . ?
C3 N3 C2 N2 176.6(2) . . . . ?
C1 N2 C2 N3 -0.3(3) . . . . ?
Ag1 N2 C2 N3 -174.57(16) 6_565 . . . ?
C2 N3 C3 C4 -97.7(3) . . . . ?
N1 N3 C3 C4 78.2(3) . . . . ?
N3 C3 C4 C5 -106.2(3) . . . . ?
N3 C3 C4 C9 72.4(3) . . . . ?
C9 C4 C5 C6 -0.3(4) . . . . ?
C3 C4 C5 C6 178.3(3) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C5 C6 C7 N4 -177.2(3) . . . . ?
Ag1 N4 C7 C8 -96.6(3) 5_566 . . . ?
Ag1 N4 C7 C6 80.6(3) 5_566 . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
N4 C7 C8 C9 176.9(2) . . . . ?
C7 C8 C9 C4 0.3(4) . . . . ?
C5 C4 C9 C8 0.0(4) . . . . ?
C3 C4 C9 C8 -178.7(2) . . . . ?
Ag1 O1 N9 O3 -152.3(2) . . . . ?
Ag1 O1 N9 O2 27.2(2) . . . . ?

_refine_diff_density_max         0.522
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.111

_shelxl_version_number           2013-2

