# Electronic Supplementary Material (ESI) for MedChemComm.
# 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 
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data_co_bg19a
_database_code_depnum_ccdc_archive 'CCDC 1426003'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;
_audit_creation_date             2015-03-10

_audit_block_code                co_bg19
_audit_block_refno               2369
_audit_block_usercomment         ?


_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         '0.25(C32 H24 Ag4 N12 O12)'
_chemical_formula_sum            'C8 H6 Ag N3 O3'
_chemical_formula_weight         300.03
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P n a 21'
_symmetry_int_tables_number      33

_chemical_absolute_configuration ad
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100(1)
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'
Ag Ag -0.8971 1.1015 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'

_space_group_name_Hall           'P 2c -2n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.678(5)
_cell_length_b                   10.566(5)
_cell_length_c                   12.076(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1745.1(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7981
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.38
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.724
_shelx_estimated_absorpt_T_min   0.500
_exptl_absorpt_coefficient_mu    2.298
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6698

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (see _computing_data_reduction)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    2.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.150
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            43039
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.474
_diffrn_reflns_theta_min         2.436
_diffrn_detector_area_resol_mean 8.19
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-Ray tube (Mo)'
_diffrn_source_type              'fine focus tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                5494
_reflns_number_total             5992
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'

_computing_cell_refinement       
;
SAINT (see _computing_data_reduction). Includes estimated systematic errors
 of the unit cell constants from Monte Carlo simulations.
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction        
'SAINT V8.34A (Bruker AXS, 1997-2013),SADABS-2014_4 (Sheldrick and Bruker AXS, 1997-2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
'encif (Wadepohl, 2009-14); encifer 1.5 (CCDC, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_shelxl_version_number           2014/7
_computing_structure_solution    'SHELXT (Sheldrick, 2013)'
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         5992
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0219
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0165P)²+1.4323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0453
_refine_ls_wR_factor_ref         0.0474
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.55(3) 0.45(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Ag1 Ag 0.39732(2) 1.02796(2) 0.38138(2) 0.01361(6) Uani 1 1 d . . . . .
Ag2 Ag 0.38481(2) 0.52570(2) 0.62660(2) 0.01295(6) Uani 1 1 d . . . . .
O1 O 0.45630(18) 1.1337(2) 0.2210(2) 0.0174(5) Uani 1 1 d . . . . .
O2 O 0.52442(19) 1.2678(3) 0.3345(2) 0.0189(5) Uani 1 1 d . . . . .
O3 O 0.48622(18) 1.3248(2) 0.1670(2) 0.0166(5) Uani 1 1 d . . . . .
O4 O 0.26327(18) 0.5874(2) 0.7656(2) 0.0160(5) Uani 1 1 d . . . . .
O5 O 0.21425(18) 0.7662(3) 0.8343(2) 0.0170(5) Uani 1 1 d . . . . .
O6 O 0.2914(2) 0.7634(3) 0.6774(2) 0.0196(6) Uani 1 1 d . . . . .
N1 N 0.38995(17) 0.8150(3) 0.3610(3) 0.0086(7) Uani 1 1 d . . . . .
N2 N 0.39239(19) 0.6136(3) 0.4506(3) 0.0118(6) Uani 1 1 d . . . . .
N3 N 0.39617(18) 0.3141(3) 0.6473(3) 0.0087(7) Uani 1 1 d . . . . .
N4 N 0.4034(2) 0.1178(3) 0.5506(3) 0.0101(6) Uani 1 1 d . . . . .
N5 N 0.4897(2) 1.2432(3) 0.2421(2) 0.0118(5) Uani 1 1 d . . . . .
N6 N 0.2563(2) 0.7077(2) 0.7590(3) 0.0105(4) Uani 1 1 d . . . . .
C1 C 0.3992(2) 0.7420(4) 0.4486(3) 0.0103(7) Uani 1 1 d . . . . .
H1 H 0.4119 0.7829 0.5172 0.012 Uiso 1 1 calc R . . . .
C2 C 0.3783(2) 0.5565(4) 0.3548(3) 0.0122(7) Uani 1 1 d . . . . .
H2 H 0.3741 0.4668 0.3534 0.015 Uiso 1 1 calc R . . . .
C3 C 0.3692(2) 0.6235(3) 0.2547(3) 0.0092(6) Uani 1 1 d . . . . .
C4 C 0.3533(2) 0.5641(3) 0.1505(3) 0.0128(7) Uani 1 1 d . . . . .
H4 H 0.3500 0.4744 0.1455 0.015 Uiso 1 1 calc R . . . .
C5 C 0.3428(2) 0.6367(4) 0.0582(3) 0.0144(7) Uani 1 1 d . . . . .
H5 H 0.3326 0.5972 -0.0116 0.017 Uiso 1 1 calc R . . . .
C6 C 0.3471(3) 0.7696(4) 0.0649(3) 0.0136(7) Uani 1 1 d . . . . .
H6 H 0.3392 0.8185 -0.0005 0.016 Uiso 1 1 calc R . . . .
C7 C 0.3624(2) 0.8302(3) 0.1644(3) 0.0106(6) Uani 1 1 d . . . . .
H7 H 0.3651 0.9199 0.1678 0.013 Uiso 1 1 calc R . . . .
C8 C 0.3740(3) 0.7570(3) 0.2609(3) 0.0089(6) Uani 1 1 d . . . . .
C9 C 0.4075(3) 0.2457(3) 0.5579(3) 0.0100(6) Uani 1 1 d . . . . .
H9 H 0.4199 0.2904 0.4911 0.012 Uiso 1 1 calc R . . . .
C10 C 0.3906(2) 0.0551(3) 0.6444(4) 0.0103(7) Uani 1 1 d . . . . .
H10 H 0.3871 -0.0347 0.6424 0.012 Uiso 1 1 calc R . . . .
C11 C 0.3820(2) 0.1171(3) 0.7468(3) 0.0093(7) Uani 1 1 d . . . . .
C12 C 0.3701(3) 0.0503(4) 0.8483(3) 0.0138(7) Uani 1 1 d . . . . .
H12 H 0.3704 -0.0396 0.8496 0.017 Uiso 1 1 calc R . . . .
C13 C 0.3584(2) 0.1179(4) 0.9438(3) 0.0154(7) Uani 1 1 d . . . . .
H13 H 0.3503 0.0745 1.0121 0.018 Uiso 1 1 calc R . . . .
C14 C 0.3581(2) 0.2514(3) 0.9421(3) 0.0146(8) Uani 1 1 d . . . . .
H14 H 0.3495 0.2962 1.0095 0.018 Uiso 1 1 calc R . . . .
C15 C 0.3699(2) 0.3180(3) 0.8460(3) 0.0127(6) Uani 1 1 d . . . . .
H15 H 0.3696 0.4079 0.8464 0.015 Uiso 1 1 calc R . . . .
C16 C 0.3825(2) 0.2504(4) 0.7460(3) 0.0081(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 O1 2.377(3) . ?
Ag1 N1 2.266(3) . ?
Ag1 N4 2.255(4) 1_565 ?
Ag2 O3 2.417(2) 2_675 ?
Ag2 O4 2.451(3) . ?
Ag2 N2 2.322(4) . ?
Ag2 N3 2.255(3) . ?
O1 N5 1.269(4) . ?
O2 N5 1.241(4) . ?
O3 Ag2 2.417(2) 2_674 ?
O3 N5 1.253(4) . ?
O4 N6 1.277(3) . ?
O5 N6 1.240(4) . ?
O6 N6 1.244(4) . ?
N1 C1 1.315(5) . ?
N1 C8 1.372(5) . ?
N2 C1 1.360(5) . ?
N2 C2 1.319(5) . ?
N3 C9 1.309(5) . ?
N3 C16 1.382(5) . ?
N4 Ag1 2.255(4) 1_545 ?
N4 C9 1.355(5) . ?
N4 C10 1.325(5) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.406(5) . ?
C3 C4 1.423(5) . ?
C3 C8 1.414(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.361(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.408(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.377(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.408(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.405(6) . ?
C11 C12 1.423(5) . ?
C11 C16 1.408(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.366(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.411(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.367(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.414(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ag1 O1 113.19(11) . . ?
N4 Ag1 O1 121.85(11) 1_565 . ?
N4 Ag1 N1 121.21(13) 1_565 . ?
O3 Ag2 O4 100.56(8) 2_675 . ?
N2 Ag2 O3 83.71(10) . 2_675 ?
N2 Ag2 O4 123.42(10) . . ?
N3 Ag2 O3 125.10(9) . 2_675 ?
N3 Ag2 O4 103.56(10) . . ?
N3 Ag2 N2 119.69(13) . . ?
N5 O1 Ag1 112.8(2) . . ?
N5 O3 Ag2 124.7(2) . 2_674 ?
N6 O4 Ag2 105.8(2) . . ?
C1 N1 Ag1 119.4(3) . . ?
C1 N1 C8 117.5(3) . . ?
C8 N1 Ag1 123.1(2) . . ?
C1 N2 Ag2 114.7(3) . . ?
C2 N2 Ag2 127.8(3) . . ?
C2 N2 C1 116.8(4) . . ?
C9 N3 Ag2 117.7(3) . . ?
C9 N3 C16 117.3(3) . . ?
C16 N3 Ag2 124.7(3) . . ?
C9 N4 Ag1 118.7(3) . 1_545 ?
C10 N4 Ag1 124.0(3) . 1_545 ?
C10 N4 C9 116.7(4) . . ?
O2 N5 O1 120.6(3) . . ?
O2 N5 O3 121.4(3) . . ?
O3 N5 O1 118.0(3) . . ?
O5 N6 O4 119.0(3) . . ?
O5 N6 O6 121.6(2) . . ?
O6 N6 O4 119.4(3) . . ?
N1 C1 N2 126.3(4) . . ?
N1 C1 H1 116.8 . . ?
N2 C1 H1 116.8 . . ?
N2 C2 H2 118.8 . . ?
N2 C2 C3 122.4(3) . . ?
C3 C2 H2 118.8 . . ?
C2 C3 C4 123.4(3) . . ?
C2 C3 C8 116.9(3) . . ?
C8 C3 C4 119.6(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(4) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.3(4) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 119.0(3) . . ?
C8 C7 H7 120.5 . . ?
N1 C8 C3 120.0(3) . . ?
N1 C8 C7 120.1(3) . . ?
C7 C8 C3 119.9(3) . . ?
N3 C9 N4 126.8(4) . . ?
N3 C9 H9 116.6 . . ?
N4 C9 H9 116.6 . . ?
N4 C10 H10 119.0 . . ?
N4 C10 C11 122.0(3) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 122.4(3) . . ?
C10 C11 C16 117.4(3) . . ?
C16 C11 C12 120.2(4) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.7(4) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.7(4) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.1 . . ?
C15 C14 C13 121.9(4) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 H15 120.7 . . ?
C14 C15 C16 118.6(3) . . ?
C16 C15 H15 120.7 . . ?
N3 C16 C11 119.6(3) . . ?
N3 C16 C15 120.4(3) . . ?
C11 C16 C15 119.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ag1 O1 N5 O2 27.9(4) . . . . ?
Ag1 O1 N5 O3 -152.1(2) . . . . ?
Ag1 N1 C1 N2 177.1(2) . . . . ?
Ag1 N1 C8 C3 -179.2(2) . . . . ?
Ag1 N1 C8 C7 0.7(4) . . . . ?
Ag1 N4 C9 N3 168.5(3) 1_545 . . . ?
Ag1 N4 C10 C11 -171.3(2) 1_545 . . . ?
Ag2 O3 N5 O1 -139.3(2) 2_674 . . . ?
Ag2 O3 N5 O2 40.8(4) 2_674 . . . ?
Ag2 O4 N6 O5 -166.1(2) . . . . ?
Ag2 O4 N6 O6 14.2(3) . . . . ?
Ag2 N2 C1 N1 -169.2(3) . . . . ?
Ag2 N2 C2 C3 169.4(2) . . . . ?
Ag2 N3 C9 N4 -171.0(3) . . . . ?
Ag2 N3 C16 C11 173.8(2) . . . . ?
Ag2 N3 C16 C15 -6.7(4) . . . . ?
N2 C2 C3 C4 -179.6(3) . . . . ?
N2 C2 C3 C8 -1.1(5) . . . . ?
N4 C10 C11 C12 -178.7(3) . . . . ?
N4 C10 C11 C16 3.2(4) . . . . ?
C1 N1 C8 C3 -0.6(5) . . . . ?
C1 N1 C8 C7 179.3(3) . . . . ?
C1 N2 C2 C3 -0.8(5) . . . . ?
C2 N2 C1 N1 2.3(5) . . . . ?
C2 C3 C4 C5 178.3(3) . . . . ?
C2 C3 C8 N1 1.9(5) . . . . ?
C2 C3 C8 C7 -178.0(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C3 C8 N1 -179.6(3) . . . . ?
C4 C3 C8 C7 0.5(5) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
C5 C6 C7 C8 0.0(5) . . . . ?
C6 C7 C8 N1 179.6(3) . . . . ?
C6 C7 C8 C3 -0.5(5) . . . . ?
C8 N1 C1 N2 -1.6(5) . . . . ?
C8 C3 C4 C5 -0.1(5) . . . . ?
C9 N3 C16 C11 0.4(4) . . . . ?
C9 N3 C16 C15 179.9(3) . . . . ?
C9 N4 C10 C11 -0.3(4) . . . . ?
C10 N4 C9 N3 -3.0(5) . . . . ?
C10 C11 C12 C13 -177.4(3) . . . . ?
C10 C11 C16 N3 -3.2(4) . . . . ?
C10 C11 C16 C15 177.3(3) . . . . ?
C11 C12 C13 C14 -0.1(5) . . . . ?
C12 C11 C16 N3 178.6(3) . . . . ?
C12 C11 C16 C15 -0.9(5) . . . . ?
C12 C13 C14 C15 -0.3(5) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?
C14 C15 C16 N3 -179.0(3) . . . . ?
C14 C15 C16 C11 0.5(5) . . . . ?
C16 N3 C9 N4 2.9(5) . . . . ?
C16 C11 C12 C13 0.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.55(3)
2 0.45(3)

_diffrn_ambient_environment      'perfluoro polyether oil / N~2~'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            CCD-PXL-KAF2
####################################################################### 
# 
# 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_co_bg18
_database_code_depnum_ccdc_archive 'CCDC 1426004'
_audit_update_record             
;
2015-09-18 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;
_audit_creation_date             2015-01-24

_audit_block_code                co_bg18
_audit_block_refno               2331
_audit_block_usercomment         BG79


_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H18 Ag2 N6, 2(B F4)'
_chemical_formula_sum            'C20 H18 Ag2 B2 F8 N6'
_chemical_formula_weight         731.76
_chemical_melting_point          ?
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      100(1)
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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2

_chemical_absolute_configuration .

_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.544(3)
_cell_length_b                   8.109(4)
_cell_length_c                   11.175(5)
_cell_angle_alpha                110.495(12)
_cell_angle_beta                 99.220(9)
_cell_angle_gamma                98.036(11)
_cell_volume                     617.7(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    8144
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.38
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.825
_shelx_estimated_absorpt_T_min   0.609
_exptl_absorpt_coefficient_mu    1.668
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6421

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (see _computing_data_reduction)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.967
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15499
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.386
_diffrn_reflns_theta_min         1.997
_diffrn_detector_area_resol_mean 8.19
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-Ray tube (Mo)'
_diffrn_source_type              'fine focus tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3860
_reflns_number_total             4134
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'

_computing_cell_refinement       
;
SAINT (see _computing_data_reduction). Includes estimated systematic errors
 of the unit cell constants from Monte Carlo simulations.
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction        
'SAINT V8.34A (Bruker AXS, 1997-2013),SADABS-2014_4 (Sheldrick and Bruker AXS, 1997-2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  
'encif (Wadepohl, 2009-14); encifer 1.5 (CCDC, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_shelxl_version_number           2014/7
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0196
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0209P)²+0.3500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0460
_refine_ls_wR_factor_ref         0.0471
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group with stretchable bonds:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
Ag Ag 1.01512(2) 0.83795(2) 0.85920(2) 0.01622(4) Uani 1 1 d . . . . .
N1 N 0.87154(16) 0.75149(15) 1.00274(11) 0.0132(2) Uani 1 1 d . . . . .
N2 N 0.84602(16) 0.88543(15) 1.11175(12) 0.0144(2) Uani 1 1 d . . . . .
N3 N 0.94961(19) 0.56576(17) 0.69556(13) 0.0200(2) Uani 1 1 d . . . . .
C1 C 0.76600(19) 0.84191(18) 1.19518(14) 0.0155(2) Uani 1 1 d . . . . .
H1 H 0.748(3) 0.944(3) 1.270(2) 0.019 Uiso 1 1 d R . . . .
C2 C 0.70368(18) 0.66207(18) 1.18310(13) 0.0137(2) Uani 1 1 d . . . . .
C3 C 0.6182(2) 0.6173(2) 1.27441(15) 0.0187(3) Uani 1 1 d . . . . .
H3 H 0.600(3) 0.717(3) 1.352(2) 0.022 Uiso 1 1 d R . . . .
C4 C 0.5611(2) 0.4385(2) 1.25228(16) 0.0200(3) Uani 1 1 d . . . . .
H4 H 0.507(3) 0.405(3) 1.313(2) 0.024 Uiso 1 1 d R . . . .
C5 C 0.5869(2) 0.3014(2) 1.14091(15) 0.0181(3) Uani 1 1 d . . . . .
H5 H 0.545(3) 0.183(3) 1.131(2) 0.022 Uiso 1 1 d R . . . .
C6 C 0.66948(19) 0.34294(18) 1.05075(15) 0.0155(2) Uani 1 1 d . . . . .
H6 H 0.688(3) 0.246(3) 0.973(2) 0.019 Uiso 1 1 d R . . . .
C7 C 0.72883(17) 0.52567(17) 1.07177(13) 0.0125(2) Uani 1 1 d . . . . .
C8 C 0.81376(18) 0.58236(17) 0.98432(13) 0.0125(2) Uani 1 1 d . . . . .
H8 H 0.831(3) 0.494(3) 0.9059(19) 0.015 Uiso 1 1 d R . . . .
C9 C 0.9267(2) 0.42461(19) 0.61825(14) 0.0170(3) Uani 1 1 d . . . . .
C10 C 0.8983(2) 0.2455(2) 0.51722(16) 0.0247(3) Uani 1 1 d . . . . .
H10A H 0.7866(18) 0.2186(9) 0.4624(12) 0.037 Uiso 1 1 calc GR . . . .
H10B H 0.9036(19) 0.1636(12) 0.5552(6) 0.037 Uiso 1 1 calc GR . . . .
H10C H 0.9871(17) 0.2427(6) 0.4710(11) 0.037 Uiso 1 1 calc GR . . . .
F1 F 0.28512(14) 0.03011(13) 0.17717(10) 0.02429(19) Uani 1 1 d . . . . .
F2 F 0.25354(19) -0.19039(13) 0.25653(11) 0.0355(3) Uani 1 1 d . . . . .
F3 F 0.20571(15) 0.08448(14) 0.37302(11) 0.0288(2) Uani 1 1 d . . . . .
F4 F 0.49397(16) 0.0491(2) 0.35281(13) 0.0484(3) Uani 1 1 d . . . . .
B B 0.3102(2) -0.0066(2) 0.29130(17) 0.0184(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag N1 2.3173(13) . ?
Ag N2 2.2267(15) 2_777 ?
Ag N3 2.2447(15) . ?
N1 N2 1.3812(16) . ?
N1 C8 1.3113(18) . ?
N2 Ag 2.2267(14) 2_777 ?
N2 C1 1.3074(19) . ?
N3 C9 1.1361(19) . ?
C1 H1 0.99(2) . ?
C1 C2 1.420(2) . ?
C2 C3 1.412(2) . ?
C2 C7 1.4064(19) . ?
C3 H3 1.00(2) . ?
C3 C4 1.375(2) . ?
C4 H4 0.94(2) . ?
C4 C5 1.411(2) . ?
C5 H5 0.93(2) . ?
C5 C6 1.377(2) . ?
C6 H6 0.99(2) . ?
C6 C7 1.4100(19) . ?
C7 C8 1.4177(19) . ?
C8 H8 0.96(2) . ?
C9 C10 1.455(2) . ?
C10 H10A 0.907(13) . ?
C10 H10B 0.907(13) . ?
C10 H10C 0.907(13) . ?
F1 B 1.398(2) . ?
F2 B 1.385(2) . ?
F3 B 1.3865(19) . ?
F4 B 1.379(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
N2 Ag N1 127.44(4) 2_777 . ?
N2 Ag N3 135.49(5) 2_777 . ?
N3 Ag N1 96.99(5) . . ?
N2 N1 Ag 117.88(8) . . ?
C8 N1 Ag 122.87(9) . . ?
C8 N1 N2 119.26(12) . . ?
N1 N2 Ag 114.12(9) . 2_777 ?
C1 N2 Ag 125.67(9) . 2_777 ?
C1 N2 N1 119.65(12) . . ?
C9 N3 Ag 174.77(13) . . ?
N2 C1 H1 115.8(12) . . ?
N2 C1 C2 124.18(13) . . ?
C2 C1 H1 120.0(12) . . ?
C3 C2 C1 123.48(13) . . ?
C7 C2 C1 116.16(12) . . ?
C7 C2 C3 120.35(13) . . ?
C2 C3 H3 118.7(12) . . ?
C4 C3 C2 118.64(14) . . ?
C4 C3 H3 122.6(12) . . ?
C3 C4 H4 120.3(13) . . ?
C3 C4 C5 121.11(14) . . ?
C5 C4 H4 118.6(13) . . ?
C4 C5 H5 117.5(13) . . ?
C6 C5 C4 120.90(13) . . ?
C6 C5 H5 121.6(13) . . ?
C5 C6 H6 120.5(12) . . ?
C5 C6 C7 118.80(13) . . ?
C7 C6 H6 120.7(12) . . ?
C2 C7 C6 120.20(13) . . ?
C2 C7 C8 116.68(12) . . ?
C6 C7 C8 123.12(13) . . ?
N1 C8 C7 124.05(12) . . ?
N1 C8 H8 116.3(11) . . ?
C7 C8 H8 119.6(11) . . ?
N3 C9 C10 178.76(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F2 B F1 108.46(13) . . ?
F2 B F3 109.73(13) . . ?
F3 B F1 109.34(13) . . ?
F4 B F1 108.64(13) . . ?
F4 B F2 110.34(15) . . ?
F4 B F3 110.30(14) . . ?

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
Ag N1 N2 Ag -7.93(12) . . . 2_777 ?
Ag N1 N2 C1 -179.81(10) . . . . ?
Ag N1 C8 C7 178.70(10) . . . . ?
Ag N2 C1 C2 -169.88(10) 2_777 . . . ?
N1 N2 C1 C2 1.0(2) . . . . ?
N2 N1 C8 C7 -1.6(2) . . . . ?
N2 C1 C2 C3 179.71(14) . . . . ?
N2 C1 C2 C7 -1.3(2) . . . . ?
C1 C2 C3 C4 179.23(14) . . . . ?
C1 C2 C7 C6 -179.34(13) . . . . ?
C1 C2 C7 C8 0.17(18) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C2 C7 C8 N1 1.2(2) . . . . ?
C3 C2 C7 C6 -0.3(2) . . . . ?
C3 C2 C7 C8 179.24(13) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C5 C6 C7 C2 0.0(2) . . . . ?
C5 C6 C7 C8 -179.45(13) . . . . ?
C6 C7 C8 N1 -179.29(13) . . . . ?
C7 C2 C3 C4 0.2(2) . . . . ?
C8 N1 N2 Ag 172.31(10) . . . 2_777 ?
C8 N1 N2 C1 0.44(19) . . . . ?


_diffrn_ambient_environment      'perfluoro polyether oil / N~2~'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            CCD-PXL-KAF2



