# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_Ligand2b
_database_code_depnum_ccdc_archive 'CCDC 1036995'
_audit_update_record             
;
2014-12-01 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2b
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 N4 O2, I'
_chemical_formula_sum            'C15 H17 I N4 O2'
_chemical_formula_weight         412.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_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+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   16.8371(11)
_cell_length_b                   10.7293(6)
_cell_length_c                   9.0448(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1633.95(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1838
_cell_measurement_theta_min      4.8940
_cell_measurement_theta_max      71.0620

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    15.511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5110
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9250
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_av_sigmaI/netI    0.0778
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.89
_diffrn_reflns_theta_max         66.59
_reflns_number_total             2736
_reflns_number_gt                1744
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_structure_refinement  
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material  
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;
_refine_special_details          
;
All H atoms were placed in calculated positions and refined using a riding model. C-H distances : CH3 0.98Α, CH2 0.99Α, aromatic, 0.95Α.

All Uiso(H) values were constrained to be 1.2 times (1.5 times for methyl) Ueq of the parent atom.

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0484P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.084(14)
_refine_ls_number_reflns         2736
_refine_ls_number_parameters     202
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.50283(5) 0.70212(5) 0.35006(13) 0.04204(19) Uani 1 1 d . . .
O1 O 0.2483(4) 0.7488(9) 0.8081(7) 0.0357(17) Uani 1 1 d . . .
O2 O 0.3866(4) 1.0246(7) 0.5194(9) 0.0361(18) Uani 1 1 d . . .
N1 N 0.5287(4) 0.7644(7) 0.8195(9) 0.025(2) Uani 1 1 d . . .
N2 N 0.3825(4) 0.7417(7) 0.8276(10) 0.0247(19) Uani 1 1 d . . .
N3 N 0.3174(5) 0.8809(8) 0.6592(10) 0.032(2) Uani 1 1 d . . .
N4 N 0.5354(5) 0.9175(8) 0.6653(10) 0.0254(19) Uani 1 1 d . . .
C1 C 0.5599(6) 0.6694(11) 0.9184(14) 0.040(3) Uani 1 1 d . . .
H1A H 0.5455 0.6899 1.0205 0.060 Uiso 1 1 calc R . .
H1B H 0.6178 0.6662 0.9094 0.060 Uiso 1 1 calc R . .
H1C H 0.5373 0.5882 0.8920 0.060 Uiso 1 1 calc R . .
C2 C 0.5779(5) 0.8443(11) 0.7452(12) 0.029(2) Uani 1 1 d . . .
H2 H 0.6342 0.8455 0.7517 0.035 Uiso 1 1 calc R . .
C3 C 0.4529(5) 0.7957(10) 0.7804(11) 0.023(2) Uani 1 1 d . . .
C4 C 0.3783(6) 0.6481(10) 0.9450(12) 0.035(2) Uani 1 1 d . . .
H4A H 0.4027 0.5704 0.9107 0.052 Uiso 1 1 calc R . .
H4B H 0.3227 0.6328 0.9707 0.052 Uiso 1 1 calc R . .
H4C H 0.4069 0.6785 1.0323 0.052 Uiso 1 1 calc R . .
C5 C 0.3120(5) 0.7878(10) 0.7675(11) 0.030(2) Uani 1 1 d . . .
C6 C 0.2403(6) 0.9205(12) 0.5950(15) 0.046(3) Uani 1 1 d . . .
H6A H 0.2108 0.8470 0.5616 0.068 Uiso 1 1 calc R . .
H6B H 0.2500 0.9759 0.5107 0.068 Uiso 1 1 calc R . .
H6C H 0.2093 0.9648 0.6701 0.068 Uiso 1 1 calc R . .
C7 C 0.3881(6) 0.9409(10) 0.6122(13) 0.028(2) Uani 1 1 d . . .
C8 C 0.4563(6) 0.8898(11) 0.6802(13) 0.031(2) Uani 1 1 d . . .
C9 C 0.5671(6) 1.0154(12) 0.5603(13) 0.037(3) Uani 1 1 d . . .
H9A H 0.5496 1.0992 0.5922 0.044 Uiso 1 1 calc R . .
H9B H 0.5467 1.0002 0.4593 0.044 Uiso 1 1 calc R . .
C10 C 0.6579(6) 1.0079(13) 0.5611(13) 0.041(3) Uani 1 1 d . . .
C11 C 0.6981(7) 0.9243(13) 0.4667(14) 0.048(3) Uani 1 1 d . . .
H11 H 0.6694 0.8749 0.3977 0.057 Uiso 1 1 calc R . .
C12 C 0.7797(7) 0.9156(15) 0.4762(16) 0.054(4) Uani 1 1 d . . .
H12 H 0.8079 0.8624 0.4107 0.065 Uiso 1 1 calc R . .
C13 C 0.8199(7) 0.9838(16) 0.5803(18) 0.054(4) Uani 1 1 d . . .
H13 H 0.8756 0.9726 0.5905 0.064 Uiso 1 1 calc R . .
C14 C 0.7829(8) 1.0657(15) 0.6678(15) 0.054(4) Uani 1 1 d . . .
H14 H 0.8132 1.1133 0.7361 0.064 Uiso 1 1 calc R . .
C15 C 0.7003(7) 1.0829(12) 0.6610(15) 0.044(3) Uani 1 1 d . . .
H15 H 0.6742 1.1427 0.7214 0.053 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.208(12) . ?
O2 C7 1.230(13) . ?
N1 C3 1.365(12) . ?
N1 C2 1.368(13) . ?
N1 C1 1.454(13) . ?
N2 C3 1.387(12) . ?
N2 C5 1.397(12) . ?
N2 C4 1.463(13) . ?
N3 C5 1.401(14) . ?
N3 C7 1.419(13) . ?
N3 C6 1.485(12) . ?
N4 C2 1.285(14) . ?
N4 C8 1.371(12) . ?
N4 C9 1.513(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2 0.9500 . ?
C3 C8 1.358(16) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.413(14) . ?
C9 C10 1.532(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.405(17) . ?
C10 C11 1.411(19) . ?
C11 C12 1.380(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.37(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.34(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.404(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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
C3 N1 C2 106.5(8) . . ?
C3 N1 C1 132.0(7) . . ?
C2 N1 C1 121.5(8) . . ?
C3 N2 C5 117.3(8) . . ?
C3 N2 C4 123.5(8) . . ?
C5 N2 C4 119.0(8) . . ?
C5 N3 C7 126.0(8) . . ?
C5 N3 C6 114.9(8) . . ?
C7 N3 C6 119.1(9) . . ?
C2 N4 C8 110.7(10) . . ?
C2 N4 C9 125.5(8) . . ?
C8 N4 C9 123.7(9) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N4 C2 N1 108.8(8) . . ?
N4 C2 H2 125.6 . . ?
N1 C2 H2 125.6 . . ?
C8 C3 N1 108.5(8) . . ?
C8 C3 N2 123.5(9) . . ?
N1 C3 N2 128.0(9) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 N2 120.9(10) . . ?
O1 C5 N3 121.2(9) . . ?
N2 C5 N3 117.9(8) . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 C8 126.7(11) . . ?
O2 C7 N3 121.3(10) . . ?
C8 C7 N3 112.0(9) . . ?
C3 C8 N4 105.5(9) . . ?
C3 C8 C7 123.0(10) . . ?
N4 C8 C7 131.5(11) . . ?
N4 C9 C10 108.2(9) . . ?
N4 C9 H9A 110.0 . . ?
C10 C9 H9A 110.0 . . ?
N4 C9 H9B 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C15 C10 C11 120.7(10) . . ?
C15 C10 C9 118.7(12) . . ?
C11 C10 C9 120.6(12) . . ?
C12 C11 C10 118.8(13) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C13 C12 C11 119.9(14) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 121.8(13) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C13 C14 C15 121.5(15) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C10 117.1(13) . . ?
C14 C15 H15 121.4 . . ?
C10 C15 H15 121.4 . . ?

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
C8 N4 C2 N1 -0.7(14) . . . . ?
C9 N4 C2 N1 -176.7(10) . . . . ?
C3 N1 C2 N4 -0.9(13) . . . . ?
C1 N1 C2 N4 179.5(10) . . . . ?
C2 N1 C3 C8 2.2(12) . . . . ?
C1 N1 C3 C8 -178.3(11) . . . . ?
C2 N1 C3 N2 -179.7(10) . . . . ?
C1 N1 C3 N2 -0.2(19) . . . . ?
C5 N2 C3 C8 0.0(14) . . . . ?
C4 N2 C3 C8 -174.3(10) . . . . ?
C5 N2 C3 N1 -177.9(10) . . . . ?
C4 N2 C3 N1 7.8(17) . . . . ?
C3 N2 C5 O1 -176.8(10) . . . . ?
C4 N2 C5 O1 -2.2(15) . . . . ?
C3 N2 C5 N3 2.9(13) . . . . ?
C4 N2 C5 N3 177.6(9) . . . . ?
C7 N3 C5 O1 174.3(10) . . . . ?
C6 N3 C5 O1 -3.3(15) . . . . ?
C7 N3 C5 N2 -5.5(15) . . . . ?
C6 N3 C5 N2 176.9(9) . . . . ?
C5 N3 C7 O2 -177.7(11) . . . . ?
C6 N3 C7 O2 -0.2(16) . . . . ?
C5 N3 C7 C8 4.4(14) . . . . ?
C6 N3 C7 C8 -178.1(10) . . . . ?
N1 C3 C8 N4 -2.5(12) . . . . ?
N2 C3 C8 N4 179.2(10) . . . . ?
N1 C3 C8 C7 177.3(10) . . . . ?
N2 C3 C8 C7 -1.0(16) . . . . ?
C2 N4 C8 C3 2.1(13) . . . . ?
C9 N4 C8 C3 178.1(9) . . . . ?
C2 N4 C8 C7 -177.8(11) . . . . ?
C9 N4 C8 C7 -1.7(19) . . . . ?
O2 C7 C8 C3 -178.9(12) . . . . ?
N3 C7 C8 C3 -1.1(14) . . . . ?
O2 C7 C8 N4 1(2) . . . . ?
N3 C7 C8 N4 178.7(12) . . . . ?
C2 N4 C9 C10 2.4(16) . . . . ?
C8 N4 C9 C10 -173.1(11) . . . . ?
N4 C9 C10 C15 -91.5(13) . . . . ?
N4 C9 C10 C11 86.4(13) . . . . ?
C15 C10 C11 C12 1.3(18) . . . . ?
C9 C10 C11 C12 -176.6(10) . . . . ?
C10 C11 C12 C13 2.6(19) . . . . ?
C11 C12 C13 C14 -4(2) . . . . ?
C12 C13 C14 C15 2(2) . . . . ?
C13 C14 C15 C10 1.7(19) . . . . ?
C11 C10 C15 C14 -3.4(17) . . . . ?
C9 C10 C15 C14 174.5(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.129
####################################################################### 
# 
# 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_Ligand2c
_database_code_depnum_ccdc_archive 'CCDC 1036996'
_audit_update_record             
;
2014-12-01 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2c
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H19 N4 O2, I'
_chemical_formula_sum            'C12 H19 I N4 O2'
_chemical_formula_weight         378.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'
_symmetry_space_group_name_Hall  'C -2yc'

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                   9.4007(7)
_cell_length_b                   22.7653(11)
_cell_length_c                   7.1881(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.244(6)
_cell_angle_gamma                90.00
_cell_volume                     1538.31(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    99.98(14)
_cell_measurement_reflns_used    2861
_cell_measurement_theta_min      3.3490
_cell_measurement_theta_max      29.1730

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    2.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6684
_exptl_absorpt_correction_T_max  0.8850
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      99.98(14)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4777
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         27.10
_reflns_number_total             2369
_reflns_number_gt                2249
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_structure_refinement  
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material  
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;
_refine_special_details          
;
 All H atoms were placed in calculated positions and refined using a riding model. C-H distances : CH3, 0.98Α, CH2 0.99Α, aromatic 0.95Α.

 All Uiso(H) values were constrained to be 1.2 times (1.5 for methyl) Ueq of the parent atom.

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0720P)²+22.8684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.28(8)
_refine_ls_number_reflns         2369
_refine_ls_number_parameters     159
_refine_ls_number_restraints     289
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1439
_refine_ls_wR_factor_gt          0.1407
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.7981(2) 0.30057(2) 0.3844(3) 0.0230(2) Uani 1 1 d U . .
O1 O 0.5036(8) 0.4360(3) 0.8719(13) 0.0308(19) Uani 1 1 d DU . .
O2 O 0.9442(10) 0.5160(5) 0.7642(18) 0.058(3) Uani 1 1 d DU . .
N1 N 0.9151(11) 0.3149(4) 0.8639(8) 0.0257(14) Uani 1 1 d DU . .
N2 N 0.6885(10) 0.3719(4) 0.8722(14) 0.025(2) Uani 1 1 d DU . .
N3 N 0.7259(11) 0.4731(5) 0.8222(19) 0.038(2) Uani 1 1 d DU . .
N4 N 1.0606(12) 0.3894(5) 0.819(2) 0.057(3) Uani 1 1 d DU . .
C1 C 0.8762(12) 0.2536(4) 0.8896(14) 0.0257(14) Uani 1 1 d DU . .
H1A H 0.9626 0.2298 0.9030 0.039 Uiso 1 1 calc R . .
H1B H 0.8218 0.2400 0.7813 0.039 Uiso 1 1 calc R . .
H1C H 0.8180 0.2497 1.0017 0.039 Uiso 1 1 calc R . .
C2 C 1.0459(14) 0.3312(5) 0.8456(15) 0.0257(14) Uani 1 1 d DU . .
H2 H 1.1240 0.3048 0.8504 0.031 Uiso 1 1 calc R . .
C3 C 0.8317(14) 0.3658(4) 0.861(2) 0.035(3) Uani 1 1 d DU . .
C4 C 0.5905(17) 0.3215(6) 0.874(2) 0.040(4) Uani 1 1 d DU . .
H4A H 0.6260 0.2910 0.7901 0.060 Uiso 1 1 calc R . .
H4B H 0.4960 0.3343 0.8324 0.060 Uiso 1 1 calc R . .
H4C H 0.5843 0.3058 1.0005 0.060 Uiso 1 1 calc R . .
C5 C 0.6325(14) 0.4262(6) 0.851(2) 0.041(3) Uani 1 1 d DU . .
C6 C 0.6578(13) 0.5266(5) 0.801(2) 0.038(2) Uani 1 1 d DU . .
H6A H 0.5778 0.5222 0.7144 0.058 Uiso 1 1 calc R . .
H6B H 0.7250 0.5556 0.7518 0.058 Uiso 1 1 calc R . .
H6C H 0.6225 0.5400 0.9220 0.058 Uiso 1 1 calc R . .
C7 C 0.8757(12) 0.4711(5) 0.8019(18) 0.026(2) Uani 1 1 d DU . .
C8 C 0.9253(14) 0.4121(6) 0.824(2) 0.037(3) Uani 1 1 d DU . .
C9 C 1.1907(15) 0.4233(7) 0.774(2) 0.049(3) Uani 1 1 d DU . .
H9A H 1.2747 0.4018 0.8220 0.058 Uiso 1 1 calc R . .
H9B H 1.1867 0.4616 0.8385 0.058 Uiso 1 1 calc R . .
C10 C 1.2104(16) 0.4342(7) 0.563(2) 0.050(3) Uani 1 1 d U . .
H10A H 1.1221 0.4518 0.5120 0.059 Uiso 1 1 calc R . .
H10B H 1.2881 0.4631 0.5452 0.059 Uiso 1 1 calc R . .
C11 C 1.2414(16) 0.3849(6) 0.463(2) 0.049(3) Uani 1 1 d U . .
H11A H 1.1686 0.3548 0.4909 0.059 Uiso 1 1 calc R . .
H11B H 1.3341 0.3695 0.5068 0.059 Uiso 1 1 calc R . .
C12 C 1.2485(17) 0.3920(7) 0.259(2) 0.057(4) Uani 1 1 d U . .
H12A H 1.2052 0.4295 0.2237 0.086 Uiso 1 1 calc R . .
H12B H 1.1969 0.3597 0.1990 0.086 Uiso 1 1 calc R . .
H12C H 1.3481 0.3914 0.2198 0.086 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.241(16) . ?
O2 C7 1.240(14) . ?
N1 C2 1.292(16) . ?
N1 C3 1.400(15) . ?
N1 C1 1.454(13) . ?
N2 C5 1.353(16) . ?
N2 C3 1.356(18) . ?
N2 C4 1.471(15) . ?
N3 C6 1.385(15) . ?
N3 C5 1.398(16) . ?
N3 C7 1.417(15) . ?
N4 C2 1.344(16) . ?
N4 C8 1.374(17) . ?
N4 C9 1.484(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2 0.9500 . ?
C3 C8 1.400(17) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.429(16) . ?
C9 C10 1.55(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.36(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.47(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 107.0(10) . . ?
C2 N1 C1 122.0(10) . . ?
C3 N1 C1 130.9(10) . . ?
C5 N2 C3 118.2(10) . . ?
C5 N2 C4 118.1(11) . . ?
C3 N2 C4 122.9(11) . . ?
C6 N3 C5 113.4(10) . . ?
C6 N3 C7 118.5(10) . . ?
C5 N3 C7 128.0(11) . . ?
C2 N4 C8 105.8(11) . . ?
C2 N4 C9 129.0(12) . . ?
C8 N4 C9 125.0(11) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 N4 113.4(11) . . ?
N1 C2 H2 123.3 . . ?
N4 C2 H2 123.3 . . ?
N2 C3 N1 129.8(10) . . ?
N2 C3 C8 124.0(11) . . ?
N1 C3 C8 105.9(11) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 N2 121.9(11) . . ?
O1 C5 N3 119.7(11) . . ?
N2 C5 N3 118.1(11) . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 N3 120.8(10) . . ?
O2 C7 C8 129.0(11) . . ?
N3 C7 C8 110.1(10) . . ?
N4 C8 C3 107.7(11) . . ?
N4 C8 C7 130.8(12) . . ?
C3 C8 C7 121.5(11) . . ?
N4 C9 C10 113.6(13) . . ?
N4 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N4 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 114.2(14) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 C12 116.3(13) . . ?
C10 C11 H11A 108.2 . . ?
C12 C11 H11A 108.2 . . ?
C10 C11 H11B 108.2 . . ?
C12 C11 H11B 108.2 . . ?
H11A C11 H11B 107.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C2 N4 -3.7(13) . . . . ?
C1 N1 C2 N4 178.6(10) . . . . ?
C8 N4 C2 N1 1.1(16) . . . . ?
C9 N4 C2 N1 -173.1(14) . . . . ?
C5 N2 C3 N1 -174.7(14) . . . . ?
C4 N2 C3 N1 -6(2) . . . . ?
C5 N2 C3 C8 -2(2) . . . . ?
C4 N2 C3 C8 167.6(15) . . . . ?
C2 N1 C3 N2 178.7(15) . . . . ?
C1 N1 C3 N2 -4(2) . . . . ?
C2 N1 C3 C8 4.7(14) . . . . ?
C1 N1 C3 C8 -177.9(9) . . . . ?
C3 N2 C5 O1 -175.0(14) . . . . ?
C4 N2 C5 O1 15(2) . . . . ?
C3 N2 C5 N3 -1(2) . . . . ?
C4 N2 C5 N3 -170.8(13) . . . . ?
C6 N3 C5 O1 -6(2) . . . . ?
C7 N3 C5 O1 177.7(15) . . . . ?
C6 N3 C5 N2 179.6(13) . . . . ?
C7 N3 C5 N2 4(2) . . . . ?
C6 N3 C7 O2 -1(2) . . . . ?
C5 N3 C7 O2 175.0(14) . . . . ?
C6 N3 C7 C8 -178.7(14) . . . . ?
C5 N3 C7 C8 -3(2) . . . . ?
C2 N4 C8 C3 2.0(18) . . . . ?
C9 N4 C8 C3 176.5(16) . . . . ?
C2 N4 C8 C7 -178.9(16) . . . . ?
C9 N4 C8 C7 -4(3) . . . . ?
N2 C3 C8 N4 -178.5(15) . . . . ?
N1 C3 C8 N4 -4.1(18) . . . . ?
N2 C3 C8 C7 2(2) . . . . ?
N1 C3 C8 C7 176.8(13) . . . . ?
O2 C7 C8 N4 3(3) . . . . ?
N3 C7 C8 N4 -179.0(17) . . . . ?
O2 C7 C8 C3 -177.8(15) . . . . ?
N3 C7 C8 C3 0(2) . . . . ?
C2 N4 C9 C10 94.7(19) . . . . ?
C8 N4 C9 C10 -79(2) . . . . ?
N4 C9 C10 C11 -69.1(17) . . . . ?
C9 C10 C11 C12 174.7(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         2.111
_refine_diff_density_min         -1.313
_refine_diff_density_rms         0.206
####################################################################### 
# 
# 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_Ligand2d
_database_code_depnum_ccdc_archive 'CCDC 1036997'
_audit_update_record             
;
2014-12-01 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        2d
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N4 O2, I, 2(H2 O)'
_chemical_formula_sum            'C14 H19 I N4 O4'
_chemical_formula_weight         434.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   10.4060(11)
_cell_length_b                   7.2140(7)
_cell_length_c                   21.938(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 89.954(9)
_cell_angle_gamma                90.00
_cell_volume                     1646.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    99.97(11)
_cell_measurement_reflns_used    2141
_cell_measurement_theta_min      3.8980
_cell_measurement_theta_max      30.4120

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    1.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7306
_exptl_absorpt_correction_T_max  0.9254
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      99.97(11)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8263
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         27.10
_reflns_number_total             3604
_reflns_number_gt                2723
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_structure_refinement  
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material  
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;
_refine_special_details          
;
Aromatic and methyl H atoms were placed in calculated positions and refined using a riding model. C-H distances : CH3 0.98Α, CH2 0.99Α, aromatic 0.95Α.

The H atoms of the two crystallised water molecules were located in the diff. map and restrained to have O-H bond distances of approximately 0.84Α, using a DFIX command.

All Uiso(H) values were constrained to be 1.2 times (1.5 times for methyl) Ueq of the parent atom.

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0162P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3604
_refine_ls_number_parameters     225
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.0775
_refine_ls_wR_factor_gt          0.0689
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.41391(3) 0.10387(4) 0.118115(13) 0.02019(10) Uani 1 1 d . . .
O1 O 0.8971(3) 0.6735(4) -0.00616(13) 0.0256(8) Uani 1 1 d . . .
O2 O 0.6004(3) 0.6060(4) 0.14560(12) 0.0157(6) Uani 1 1 d . . .
O3 O 0.7034(3) 0.0389(5) 0.03120(17) 0.0312(8) Uani 1 1 d D . .
O4 O 0.3179(3) 0.5671(4) 0.14880(16) 0.0297(8) Uani 1 1 d D . .
N1 N 0.9948(3) 0.8415(4) 0.19774(15) 0.0133(8) Uani 1 1 d . . .
N2 N 0.9610(3) 0.7573(5) 0.08948(15) 0.0142(8) Uani 1 1 d . . .
N3 N 0.7521(3) 0.6324(5) 0.07078(15) 0.0166(8) Uani 1 1 d . . .
N4 N 0.7986(3) 0.7866(4) 0.23052(15) 0.0131(8) Uani 1 1 d . . .
C1 C 1.1323(4) 0.8911(6) 0.20352(19) 0.0178(9) Uani 1 1 d . . .
H1A H 1.1501 0.9303 0.2454 0.027 Uiso 1 1 calc R . .
H1B H 1.1524 0.9928 0.1755 0.027 Uiso 1 1 calc R . .
H1C H 1.1854 0.7831 0.1935 0.027 Uiso 1 1 calc R . .
C2 C 0.9162(4) 0.8433(5) 0.24624(19) 0.0131(9) Uani 1 1 d . . .
H2 H 0.9407 0.8798 0.2862 0.016 Uiso 1 1 calc R . .
C3 C 0.9228(4) 0.7807(5) 0.14846(18) 0.0120(9) Uani 1 1 d . . .
C4 C 1.0889(4) 0.8109(7) 0.0656(2) 0.0242(11) Uani 1 1 d . . .
H4A H 1.1001 0.9453 0.0696 0.036 Uiso 1 1 calc R . .
H4B H 1.0952 0.7760 0.0225 0.036 Uiso 1 1 calc R . .
H4C H 1.1560 0.7470 0.0888 0.036 Uiso 1 1 calc R . .
C5 C 0.8710(4) 0.6877(6) 0.0473(2) 0.0184(10) Uani 1 1 d . . .
C6 C 0.6612(4) 0.5495(6) 0.0269(2) 0.0232(11) Uani 1 1 d . . .
H6A H 0.6080 0.4571 0.0478 0.035 Uiso 1 1 calc R . .
H6B H 0.7093 0.4897 -0.0061 0.035 Uiso 1 1 calc R . .
H6C H 0.6061 0.6467 0.0100 0.035 Uiso 1 1 calc R . .
C7 C 0.7070(4) 0.6575(5) 0.12976(18) 0.0138(9) Uani 1 1 d . . .
C8 C 0.8018(4) 0.7448(5) 0.16822(17) 0.0119(9) Uani 1 1 d . . .
C9 C 0.6915(4) 0.7879(5) 0.27197(18) 0.0119(9) Uani 1 1 d . . .
C10 C 0.5734(4) 0.8602(5) 0.25237(18) 0.0129(9) Uani 1 1 d . . .
H10 H 0.5624 0.9002 0.2114 0.015 Uiso 1 1 calc R . .
C11 C 0.4741(4) 0.8723(5) 0.29336(18) 0.0156(9) Uani 1 1 d . . .
H11 H 0.3935 0.9198 0.2804 0.019 Uiso 1 1 calc R . .
C12 C 0.4895(4) 0.8158(6) 0.35374(19) 0.0188(10) Uani 1 1 d . . .
H12 H 0.4203 0.8264 0.3818 0.023 Uiso 1 1 calc R . .
C13 C 0.6071(4) 0.7439(6) 0.37258(19) 0.0175(10) Uani 1 1 d . . .
H13 H 0.6181 0.7046 0.4136 0.021 Uiso 1 1 calc R . .
C14 C 0.7081(4) 0.7295(5) 0.33167(18) 0.0142(9) Uani 1 1 d . . .
H14 H 0.7882 0.6798 0.3444 0.017 Uiso 1 1 calc R . .
H15 H 0.335(4) 0.460(2) 0.1361(18) 0.021 Uiso 1 1 d D . .
H16 H 0.380(3) 0.633(4) 0.1379(18) 0.021 Uiso 1 1 d D . .
H17 H 0.634(3) 0.064(8) 0.049(2) 0.07(2) Uiso 1 1 d D . .
H18 H 0.682(5) 0.014(9) -0.0051(10) 0.08(3) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.209(5) . ?
O2 C7 1.220(5) . ?
O3 H17 0.844(10) . ?
O3 H18 0.846(10) . ?
O4 H15 0.839(10) . ?
O4 H16 0.838(10) . ?
N1 C2 1.342(5) . ?
N1 C3 1.387(5) . ?
N1 C1 1.480(5) . ?
N2 C3 1.364(5) . ?
N2 C5 1.409(5) . ?
N2 C4 1.482(5) . ?
N3 C7 1.388(5) . ?
N3 C5 1.398(5) . ?
N3 C6 1.476(5) . ?
N4 C2 1.335(5) . ?
N4 C8 1.400(5) . ?
N4 C9 1.438(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2 0.9500 . ?
C3 C8 1.357(6) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.443(5) . ?
C9 C14 1.387(5) . ?
C9 C10 1.403(5) . ?
C10 C11 1.372(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(6) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
H17 O3 H18 104(2) . . ?
H15 O4 H16 106(2) . . ?
C2 N1 C3 106.9(3) . . ?
C2 N1 C1 121.2(3) . . ?
C3 N1 C1 131.8(3) . . ?
C3 N2 C5 118.3(4) . . ?
C3 N2 C4 124.3(3) . . ?
C5 N2 C4 117.3(3) . . ?
C7 N3 C5 127.2(4) . . ?
C7 N3 C6 116.4(4) . . ?
C5 N3 C6 116.3(3) . . ?
C2 N4 C8 107.3(4) . . ?
C2 N4 C9 123.0(3) . . ?
C8 N4 C9 129.5(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N4 C2 N1 110.5(4) . . ?
N4 C2 H2 124.7 . . ?
N1 C2 H2 124.7 . . ?
C8 C3 N2 123.3(4) . . ?
C8 C3 N1 108.3(3) . . ?
N2 C3 N1 128.4(4) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 N3 122.1(4) . . ?
O1 C5 N2 121.3(4) . . ?
N3 C5 N2 116.7(4) . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 N3 122.2(4) . . ?
O2 C7 C8 126.0(4) . . ?
N3 C7 C8 111.8(4) . . ?
C3 C8 N4 107.0(3) . . ?
C3 C8 C7 122.1(4) . . ?
N4 C8 C7 130.5(4) . . ?
C14 C9 C10 120.8(4) . . ?
C14 C9 N4 119.9(4) . . ?
C10 C9 N4 119.2(4) . . ?
C11 C10 C9 118.8(4) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 121.1(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.2(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 119.6(4) . . ?
C13 C14 H14 120.2 . . ?
C9 C14 H14 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.847
_refine_diff_density_min         -0.865
_refine_diff_density_rms         0.140
####################################################################### 
# 
# 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_Complex3b
_database_code_depnum_ccdc_archive 'CCDC 1036998'
_audit_update_record             
;
2014-12-01 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3b
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 Ag N4 O4'
_chemical_formula_sum            'C17 H19 Ag N4 O4'
_chemical_formula_weight         451.23

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   7.9222(8)
_cell_length_b                   9.4296(18)
_cell_length_c                   12.3121(19)
_cell_angle_alpha                105.139(15)
_cell_angle_beta                 96.986(10)
_cell_angle_gamma                92.438(11)
_cell_volume                     878.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200.01(10)
_cell_measurement_reflns_used    1448
_cell_measurement_theta_min      3.7980
_cell_measurement_theta_max      27.7070

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    1.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7652
_exptl_absorpt_correction_T_max  0.9434
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200.01(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13274
_diffrn_reflns_av_R_equivalents  0.1124
_diffrn_reflns_av_sigmaI/netI    0.1194
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         28.38
_reflns_number_total             4315
_reflns_number_gt                3000
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_structure_refinement  
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material  
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;
_refine_special_details          
;
All H atoms were placed in calculated positions and refined using a riding model. C-H distances : CH3 0.98 Α, CH2 0.99Α, aromatic 0.95Α.

All Uiso(H) values were constrained to be 1.2 times (1.5 times for methyl) Ueq of the parent atom.

The crystals obtained were of very poor quality. The data was refined as a twin using a BASF instruction.

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0703P)²+2.1695P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4315
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.1792
_refine_ls_wR_factor_gt          0.1653
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.33759(7) 0.11836(6) 0.46554(5) 0.0350(2) Uani 1 1 d . . .
O1 O 0.1740(7) -0.7128(5) 0.1635(5) 0.0451(13) Uani 1 1 d . . .
O2 O 0.2987(8) -0.3379(6) 0.0095(4) 0.0460(13) Uani 1 1 d . . .
O3 O 0.4362(6) 0.3286(5) 0.5705(4) 0.0381(11) Uani 1 1 d . . .
O4 O 0.1718(7) 0.3335(6) 0.6079(5) 0.0473(13) Uani 1 1 d . . .
N1 N 0.2286(6) -0.2150(6) 0.3841(5) 0.0268(11) Uani 1 1 d . . .
N2 N 0.1826(7) -0.4812(6) 0.2798(5) 0.0284(12) Uani 1 1 d . . .
N3 N 0.2239(7) -0.5233(6) 0.0861(5) 0.0316(12) Uani 1 1 d . . .
N4 N 0.2908(6) -0.1309(5) 0.2447(5) 0.0246(11) Uani 1 1 d . . .
C1 C 0.2053(10) -0.2148(9) 0.5001(6) 0.0409(17) Uani 1 1 d . . .
H1A H 0.0990 -0.2727 0.4989 0.061 Uiso 1 1 calc R . .
H1B H 0.1996 -0.1132 0.5455 0.061 Uiso 1 1 calc R . .
H1C H 0.3016 -0.2582 0.5339 0.061 Uiso 1 1 calc R . .
C2 C 0.2775(8) -0.0876(7) 0.3561(6) 0.0277(14) Uani 1 1 d . . .
C3 C 0.2184(7) -0.3334(7) 0.2907(5) 0.0226(12) Uani 1 1 d . . .
C4 C 0.1544(11) -0.5426(9) 0.3744(7) 0.0444(19) Uani 1 1 d . . .
H4A H 0.1266 -0.6492 0.3457 0.067 Uiso 1 1 calc R . .
H4B H 0.0596 -0.4966 0.4108 0.067 Uiso 1 1 calc R . .
H4C H 0.2580 -0.5231 0.4300 0.067 Uiso 1 1 calc R . .
C5 C 0.1909(8) -0.5802(7) 0.1760(6) 0.0316(15) Uani 1 1 d . . .
C6 C 0.2317(11) -0.6335(8) -0.0234(7) 0.0466(19) Uani 1 1 d . . .
H6A H 0.3473 -0.6661 -0.0253 0.070 Uiso 1 1 calc R . .
H6B H 0.2020 -0.5890 -0.0861 0.070 Uiso 1 1 calc R . .
H6C H 0.1507 -0.7183 -0.0313 0.070 Uiso 1 1 calc R . .
C7 C 0.2637(9) -0.3753(7) 0.0914(6) 0.0295(14) Uani 1 1 d . . .
C8 C 0.2561(8) -0.2816(6) 0.2030(6) 0.0250(13) Uani 1 1 d . . .
C9 C 0.3499(8) -0.0314(7) 0.1811(6) 0.0292(14) Uani 1 1 d . . .
H9A H 0.3079 0.0668 0.2107 0.035 Uiso 1 1 calc R . .
H9B H 0.2998 -0.0692 0.1004 0.035 Uiso 1 1 calc R . .
C10 C 0.5402(8) -0.0147(7) 0.1882(6) 0.0273(14) Uani 1 1 d . . .
C11 C 0.6489(8) -0.0967(7) 0.2423(6) 0.0308(14) Uani 1 1 d . . .
H11 H 0.6007 -0.1679 0.2742 0.037 Uiso 1 1 calc R . .
C12 C 0.8252(8) -0.0764(7) 0.2503(5) 0.0289(14) Uani 1 1 d . . .
H12 H 0.8976 -0.1323 0.2874 0.035 Uiso 1 1 calc R . .
C13 C 0.8937(9) 0.0288(9) 0.2022(7) 0.0406(17) Uani 1 1 d . . .
H13 H 1.0138 0.0459 0.2078 0.049 Uiso 1 1 calc R . .
C14 C 0.7861(9) 0.1086(7) 0.1462(7) 0.0364(16) Uani 1 1 d . . .
H14 H 0.8332 0.1776 0.1118 0.044 Uiso 1 1 calc R . .
C15 C 0.6132(9) 0.0874(7) 0.1406(6) 0.0335(15) Uani 1 1 d . . .
H15 H 0.5413 0.1436 0.1035 0.040 Uiso 1 1 calc R . .
C16 C 0.3174(9) 0.3909(7) 0.6241(6) 0.0330(15) Uani 1 1 d . . .
C17 C 0.3661(11) 0.5398(9) 0.7074(8) 0.055(2) Uani 1 1 d . . .
H17A H 0.2672 0.5990 0.7107 0.082 Uiso 1 1 calc R . .
H17B H 0.4592 0.5900 0.6827 0.082 Uiso 1 1 calc R . .
H17C H 0.4035 0.5269 0.7829 0.082 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 C2 2.052(7) . ?
Ag1 O3 2.120(5) . ?
O1 C5 1.219(8) . ?
O2 C7 1.209(8) . ?
O3 C16 1.289(9) . ?
O4 C16 1.224(9) . ?
N1 C3 1.369(8) . ?
N1 C2 1.386(8) . ?
N1 C1 1.462(9) . ?
N2 C3 1.379(8) . ?
N2 C5 1.382(9) . ?
N2 C4 1.466(9) . ?
N3 C5 1.396(9) . ?
N3 C7 1.401(8) . ?
N3 C6 1.482(9) . ?
N4 C2 1.343(8) . ?
N4 C8 1.382(8) . ?
N4 C9 1.466(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C8 1.354(9) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.436(9) . ?
C9 C10 1.498(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C15 1.391(9) . ?
C10 C11 1.403(9) . ?
C11 C12 1.390(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.403(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.396(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.367(9) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.509(11) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 Ag1 O3 171.4(2) . . ?
C16 O3 Ag1 109.0(4) . . ?
C3 N1 C2 109.8(5) . . ?
C3 N1 C1 128.0(6) . . ?
C2 N1 C1 122.1(6) . . ?
C3 N2 C5 118.4(5) . . ?
C3 N2 C4 124.2(6) . . ?
C5 N2 C4 117.1(6) . . ?
C5 N3 C7 126.8(6) . . ?
C5 N3 C6 115.8(6) . . ?
C7 N3 C6 117.2(6) . . ?
C2 N4 C8 110.6(5) . . ?
C2 N4 C9 123.4(5) . . ?
C8 N4 C9 125.7(6) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N4 C2 N1 105.2(5) . . ?
N4 C2 Ag1 127.8(4) . . ?
N1 C2 Ag1 126.8(5) . . ?
C8 C3 N1 107.3(5) . . ?
C8 C3 N2 122.6(6) . . ?
N1 C3 N2 130.1(6) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 N2 121.5(6) . . ?
O1 C5 N3 120.8(7) . . ?
N2 C5 N3 117.7(6) . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 N3 121.7(6) . . ?
O2 C7 C8 127.1(6) . . ?
N3 C7 C8 111.2(5) . . ?
C3 C8 N4 107.1(6) . . ?
C3 C8 C7 123.2(5) . . ?
N4 C8 C7 129.7(6) . . ?
N4 C9 C10 113.4(5) . . ?
N4 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N4 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C15 C10 C11 118.3(6) . . ?
C15 C10 C9 119.0(6) . . ?
C11 C10 C9 122.8(6) . . ?
C12 C11 C10 121.6(6) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 118.2(6) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C14 C13 C12 120.4(6) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.1(6) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 121.3(6) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
O4 C16 O3 122.0(7) . . ?
O4 C16 C17 121.3(7) . . ?
O3 C16 C17 116.6(7) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        28.38
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         1.865
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.145
####################################################################### 
# 
# 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_Complex3c
_database_code_depnum_ccdc_archive 'CCDC 1036999'
_audit_update_record             
;
2014-12-01 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3c
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H21 Ag N4 O4), H2 O'
_chemical_formula_sum            'C28 H44 Ag2 N8 O9'
_chemical_formula_weight         852.45

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.0608(4)
_cell_length_b                   9.5485(5)
_cell_length_c                   19.4525(9)
_cell_angle_alpha                87.707(4)
_cell_angle_beta                 84.198(4)
_cell_angle_gamma                82.717(4)
_cell_volume                     1660.21(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      3.3230
_cell_measurement_theta_max      30.8240

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             868
_exptl_absorpt_coefficient_mu    1.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7803
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            24918
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         28.28
_reflns_number_total             8239
_reflns_number_gt                6835
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_structure_refinement  
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material  
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;
_refine_special_details          
;
All H atoms were placed in calculated positions and refined using a riding model. C-H distances : CH3 0.98Α, CH2 0.99Α, aromatic 0.95Α, OH 0.95Α.

All Uiso(H) values were constrained to be 1.2 times (1.5 times for methyl) Ueq of the parent atom.

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0293P)²+1.5818P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8239
_refine_ls_number_parameters     395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0764
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.61926(2) 0.34047(2) 0.298453(10) 0.02048(6) Uani 1 1 d . . .
Ag2 Ag 0.36726(2) 0.22784(2) 0.219453(10) 0.01844(6) Uani 1 1 d . . .
O1 O 0.3563(2) -0.3358(2) 0.48347(11) 0.0273(5) Uani 1 1 d . . .
O2 O 0.1847(2) 0.1259(2) 0.52745(10) 0.0236(4) Uani 1 1 d . . .
O3 O 0.6749(2) 0.5261(2) 0.24562(10) 0.0259(4) Uani 1 1 d . . .
O4 O 0.8984(3) 0.4354(2) 0.19720(12) 0.0406(6) Uani 1 1 d . . .
O5 O 0.6656(2) 0.8398(2) -0.00841(10) 0.0232(4) Uani 1 1 d . . .
O6 O 0.8103(2) 0.3643(2) -0.02334(10) 0.0208(4) Uani 1 1 d . . .
O7 O 0.2312(2) 0.1015(2) 0.28270(10) 0.0222(4) Uani 1 1 d . . .
O8 O 0.3884(2) -0.0891(2) 0.25195(10) 0.0276(5) Uani 1 1 d . . .
O9 O 0.92806(6) 0.20847(11) 0.28464(5) 0.0304(5) Uani 1 1 d G . .
N1 N 0.56891(8) 0.03876(7) 0.35673(4) 0.0170(4) Uani 1 1 d G . .
N2 N 0.47175(11) -0.17041(8) 0.41728(4) 0.0187(5) Uani 1 1 d G . .
N3 N 0.26587(11) -0.10498(10) 0.50145(5) 0.0166(4) Uani 1 1 d G . .
N4 N 0.41766(9) 0.20166(8) 0.41070(3) 0.0164(4) Uani 1 1 d G . .
N5 N 0.43581(7) 0.51056(8) 0.14368(4) 0.0159(4) Uani 1 1 d G . .
N6 N 0.53864(10) 0.69706(8) 0.06702(4) 0.0162(4) Uani 1 1 d G . .
N7 N 0.74288(11) 0.60355(10) -0.01240(4) 0.0164(4) Uani 1 1 d G . .
N8 N 0.57817(9) 0.32875(7) 0.10007(3) 0.0147(4) Uani 1 1 d G . .
C1 C 0.69281(9) -0.02383(7) 0.30810(4) 0.0237(6) Uani 1 1 d G . .
H1A H 0.7603 -0.0912 0.3331 0.035 Uiso 1 1 calc R . .
H1B H 0.7480 0.0510 0.2866 0.035 Uiso 1 1 calc R . .
H1C H 0.6525 -0.0729 0.2722 0.035 Uiso 1 1 calc R . .
C2 C 0.5301(3) 0.1834(3) 0.36035(13) 0.0170(5) Uani 1 1 d . . .
C3 C 0.4755(3) -0.0287(3) 0.40313(13) 0.0153(5) Uani 1 1 d . . .
C4 C 0.5669(3) -0.2831(3) 0.37806(17) 0.0317(7) Uani 1 1 d . . .
H4A H 0.5534 -0.2696 0.3288 0.048 Uiso 1 1 calc R . .
H4B H 0.5385 -0.3752 0.3944 0.048 Uiso 1 1 calc R . .
H4C H 0.6719 -0.2791 0.3850 0.048 Uiso 1 1 calc R . .
C5 C 0.3640(3) -0.2118(3) 0.46830(14) 0.0193(5) Uani 1 1 d . . .
C6 C 0.1479(3) -0.1543(3) 0.55089(14) 0.0216(6) Uani 1 1 d . . .
H6A H 0.0841 -0.2067 0.5264 0.032 Uiso 1 1 calc R . .
H6B H 0.0873 -0.0728 0.5729 0.032 Uiso 1 1 calc R . .
H6C H 0.1939 -0.2161 0.5863 0.032 Uiso 1 1 calc R . .
C7 C 0.2695(3) 0.0413(3) 0.49202(13) 0.0165(5) Uani 1 1 d . . .
C8 C 0.37988(9) 0.07346(8) 0.43774(4) 0.0151(5) Uani 1 1 d G . .
C9 C 0.33624(11) 0.33999(8) 0.42911(3) 0.0245(6) Uani 1 1 d G . .
H9C H 0.4020 0.4143 0.4169 0.029 Uiso 1 1 calc R . .
H9D H 0.3083 0.3415 0.4796 0.029 Uiso 1 1 calc R . .
C10 C 0.1936(3) 0.3717(3) 0.39093(17) 0.0288(6) Uani 1 1 d . . .
H10A H 0.2210 0.3666 0.3404 0.035 Uiso 1 1 calc R . .
H10B H 0.1260 0.2995 0.4046 0.035 Uiso 1 1 calc R . .
C11 C 0.1138(4) 0.5161(3) 0.40791(19) 0.0360(8) Uani 1 1 d . . .
H11A H 0.0881 0.5210 0.4585 0.043 Uiso 1 1 calc R . .
H11B H 0.1819 0.5878 0.3940 0.043 Uiso 1 1 calc R . .
C12 C -0.0269(4) 0.5508(4) 0.3722(2) 0.0444(9) Uani 1 1 d . . .
H12A H -0.0020 0.5470 0.3220 0.067 Uiso 1 1 calc R . .
H12B H -0.0739 0.6458 0.3844 0.067 Uiso 1 1 calc R . .
H12C H -0.0961 0.4820 0.3870 0.067 Uiso 1 1 calc R . .
C13 C 0.79788(9) 0.53429(9) 0.20907(4) 0.0212(6) Uani 1 1 d G . .
C14 C 0.82189(11) 0.67810(9) 0.17823(5) 0.0269(6) Uani 1 1 d G . .
H14A H 0.8839 0.7236 0.2069 0.040 Uiso 1 1 calc R . .
H14B H 0.7251 0.7363 0.1764 0.040 Uiso 1 1 calc R . .
H14C H 0.8723 0.6678 0.1314 0.040 Uiso 1 1 calc R . .
C15 C 0.3214(3) 0.5893(3) 0.19155(14) 0.0241(6) Uani 1 1 d . . .
H15A H 0.3667 0.6606 0.2144 0.036 Uiso 1 1 calc R . .
H15B H 0.2808 0.5239 0.2264 0.036 Uiso 1 1 calc R . .
H15C H 0.2407 0.6359 0.1657 0.036 Uiso 1 1 calc R . .
C16 C 0.46772(7) 0.36540(7) 0.14973(3) 0.0163(5) Uani 1 1 d G . .
C17 C 0.53037(8) 0.56112(8) 0.09200(3) 0.0152(5) Uani 1 1 d G . .
C18 C 0.43868(11) 0.82179(8) 0.09399(5) 0.0213(6) Uani 1 1 d G . .
H18A H 0.3343 0.8057 0.0928 0.032 Uiso 1 1 calc R . .
H18B H 0.4581 0.9054 0.0653 0.032 Uiso 1 1 calc R . .
H18C H 0.4575 0.8368 0.1417 0.032 Uiso 1 1 calc R . .
C19 C 0.6502(3) 0.7213(3) 0.01406(13) 0.0165(5) Uani 1 1 d . . .
C20 C 0.8630(3) 0.6339(3) -0.06544(14) 0.0230(6) Uani 1 1 d . . .
H20A H 0.8201 0.6924 -0.1028 0.034 Uiso 1 1 calc R . .
H20B H 0.9146 0.5450 -0.0841 0.034 Uiso 1 1 calc R . .
H20C H 0.9344 0.6844 -0.0447 0.034 Uiso 1 1 calc R . .
C21 C 0.7317(3) 0.4612(3) 0.00675(13) 0.0167(5) Uani 1 1 d . . .
C22 C 0.6208(3) 0.4484(3) 0.06375(13) 0.0140(5) Uani 1 1 d . . .
C23 C 0.6500(3) 0.1837(3) 0.08864(14) 0.0180(5) Uani 1 1 d . . .
H23A H 0.6629 0.1666 0.0384 0.022 Uiso 1 1 calc R . .
H23B H 0.5837 0.1167 0.1109 0.022 Uiso 1 1 calc R . .
C24 C 0.8011(3) 0.1549(3) 0.11701(14) 0.0194(5) Uani 1 1 d . . .
H24A H 0.8638 0.2286 0.0993 0.023 Uiso 1 1 calc R . .
H24B H 0.7875 0.1591 0.1681 0.023 Uiso 1 1 calc R . .
C25 C 0.8790(3) 0.0113(3) 0.09609(17) 0.0292(7) Uani 1 1 d . . .
H25A H 0.8914 0.0082 0.0450 0.035 Uiso 1 1 calc R . .
H25B H 0.8144 -0.0613 0.1133 0.035 Uiso 1 1 calc R . .
C26 C 1.0311(3) -0.0263(3) 0.12284(19) 0.0349(7) Uani 1 1 d . . .
H26A H 1.1000 0.0377 0.1014 0.052 Uiso 1 1 calc R . .
H26B H 1.0700 -0.1239 0.1113 0.052 Uiso 1 1 calc R . .
H26C H 1.0215 -0.0169 0.1731 0.052 Uiso 1 1 calc R . .
C27 C 0.2696(3) -0.0325(3) 0.28066(13) 0.0190(5) Uani 1 1 d . . .
C28 C 0.1567(3) -0.1207(3) 0.31772(15) 0.0277(6) Uani 1 1 d . . .
H28A H 0.0653 -0.1084 0.2940 0.042 Uiso 1 1 calc R . .
H28B H 0.1331 -0.0903 0.3655 0.042 Uiso 1 1 calc R . .
H28C H 0.1987 -0.2205 0.3176 0.042 Uiso 1 1 calc R . .
H9A H 0.9268 0.2752 0.2540 0.042 Uiso 1 1 d G . .
H9B H 1.0178 0.1658 0.2834 0.042 Uiso 1 1 d G . .


_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 C2 2.078(3) . ?
Ag1 O3 2.1042(19) . ?
Ag1 Ag2 3.1931(3) . ?
Ag2 C16 2.0747 . ?
Ag2 O7 2.1074(18) . ?
O1 C5 1.218(3) . ?
O2 C7 1.224(3) . ?
O3 C13 1.269(2) . ?
O4 C13 1.238(2) . ?
O5 C19 1.216(3) . ?
O6 C21 1.224(3) . ?
O7 C27 1.283(3) . ?
O8 C27 1.232(3) . ?
O9 H9A 0.85 . ?
O9 H9B 0.8605 . ?
N1 C3 1.373(3) . ?
N1 C2 1.384(3) . ?
N1 C1 1.4741 . ?
N2 C3 1.374(3) . ?
N2 C5 1.402(3) . ?
N2 C4 1.476(3) . ?
N3 C5 1.398(3) . ?
N3 C7 1.405(3) . ?
N3 C6 1.474(3) . ?
N4 C2 1.340(3) . ?
N4 C8 1.3821 . ?
N4 C9 1.4679 . ?
N5 C17 1.3674 . ?
N5 C16 1.3823 . ?
N5 C15 1.473(3) . ?
N6 C17 1.3760 . ?
N6 C19 1.402(3) . ?
N6 C18 1.4813 . ?
N7 C19 1.398(3) . ?
N7 C21 1.409(3) . ?
N7 C20 1.470(3) . ?
N8 C16 1.3416 . ?
N8 C22 1.395(3) . ?
N8 C23 1.469(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C8 1.369(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.432(3) . ?
C9 C10 1.546(3) . ?
C9 H9C 0.9900 . ?
C9 H9D 0.9900 . ?
C10 C11 1.507(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.507(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.5087 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 C22 1.365(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.431(3) . ?
C23 C24 1.516(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.513(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.517(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.515(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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 Ag1 O3 168.72(9) . . ?
C2 Ag1 Ag2 72.09(7) . . ?
O3 Ag1 Ag2 107.01(5) . . ?
C16 Ag2 O7 170.17(5) . . ?
C16 Ag2 Ag1 74.576(18) . . ?
O7 Ag2 Ag1 113.35(5) . . ?
C13 O3 Ag1 123.70(13) . . ?
C27 O7 Ag2 116.35(17) . . ?
H9A O9 H9B 108.1 . . ?
C3 N1 C2 109.62(16) . . ?
C3 N1 C1 128.55(11) . . ?
C2 N1 C1 121.83(11) . . ?
C3 N2 C5 118.59(17) . . ?
C3 N2 C4 123.83(17) . . ?
C5 N2 C4 117.39(17) . . ?
C5 N3 C7 126.61(16) . . ?
C5 N3 C6 115.17(17) . . ?
C7 N3 C6 118.22(17) . . ?
C2 N4 C8 111.18(12) . . ?
C2 N4 C9 123.66(12) . . ?
C8 N4 C9 124.9 . . ?
C17 N5 C16 109.6 . . ?
C17 N5 C15 129.04(12) . . ?
C16 N5 C15 121.24(12) . . ?
C17 N6 C19 118.80(11) . . ?
C17 N6 C18 123.9 . . ?
C19 N6 C18 117.24(11) . . ?
C19 N7 C21 126.43(16) . . ?
C19 N7 C20 115.72(16) . . ?
C21 N7 C20 117.85(17) . . ?
C16 N8 C22 110.44(10) . . ?
C16 N8 C23 124.52(11) . . ?
C22 N8 C23 124.93(15) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N4 C2 N1 105.46(18) . . ?
N4 C2 Ag1 126.68(17) . . ?
N1 C2 Ag1 127.81(16) . . ?
N1 C3 N2 130.1(2) . . ?
N1 C3 C8 107.32(18) . . ?
N2 C3 C8 122.59(19) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 N3 121.1(2) . . ?
O1 C5 N2 121.5(2) . . ?
N3 C5 N2 117.4(2) . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 N3 121.3(2) . . ?
O2 C7 C8 126.8(2) . . ?
N3 C7 C8 111.91(19) . . ?
C3 C8 N4 106.37(11) . . ?
C3 C8 C7 122.72(16) . . ?
N4 C8 C7 130.88(11) . . ?
N4 C9 C10 111.08(12) . . ?
N4 C9 H9C 109.4 . . ?
C10 C9 H9C 109.4 . . ?
N4 C9 H9D 109.4 . . ?
C10 C9 H9D 109.4 . . ?
H9C C9 H9D 108.0 . . ?
C11 C10 C9 110.8(2) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 C10 112.5(3) . . ?
C12 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 O3 125.64(15) . . ?
O4 C13 C14 118.05(11) . . ?
O3 C13 C14 116.31(10) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N8 C16 N5 105.9 . . ?
N8 C16 Ag2 125.8 . . ?
N5 C16 Ag2 128.3 . . ?
C22 C17 N5 107.78(11) . . ?
C22 C17 N6 122.00(11) . . ?
N5 C17 N6 130.2 . . ?
N6 C18 H18A 109.5 . . ?
N6 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N6 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 N7 121.1(2) . . ?
O5 C19 N6 121.6(2) . . ?
N7 C19 N6 117.39(19) . . ?
N7 C20 H20A 109.5 . . ?
N7 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N7 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O6 C21 N7 121.8(2) . . ?
O6 C21 C22 126.6(2) . . ?
N7 C21 C22 111.6(2) . . ?
C17 C22 N8 106.26(17) . . ?
C17 C22 C21 123.4(2) . . ?
N8 C22 C21 130.4(2) . . ?
N8 C23 C24 112.79(19) . . ?
N8 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
N8 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C25 C24 C23 110.8(2) . . ?
C25 C24 H24A 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
C24 C25 C26 114.2(2) . . ?
C24 C25 H25A 108.7 . . ?
C26 C25 H25A 108.7 . . ?
C24 C25 H25B 108.7 . . ?
C26 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O8 C27 O7 124.5(3) . . ?
O8 C27 C28 120.7(3) . . ?
O7 C27 C28 114.8(2) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 Ag1 Ag2 C16 -173.27(8) . . . . ?
O3 Ag1 Ag2 C16 18.52(6) . . . . ?
C2 Ag1 Ag2 O7 12.90(9) . . . . ?
O3 Ag1 Ag2 O7 -155.31(8) . . . . ?
C2 Ag1 O3 C13 167.6(4) . . . . ?
Ag2 Ag1 O3 C13 -108.74(15) . . . . ?
C16 Ag2 O7 C27 122.6(3) . . . . ?
Ag1 Ag2 O7 C27 -94.79(18) . . . . ?
C8 N4 C2 N1 -2.10(18) . . . . ?
C9 N4 C2 N1 -176.20(7) . . . . ?
C8 N4 C2 Ag1 175.48(12) . . . . ?
C9 N4 C2 Ag1 1.4(2) . . . . ?
C3 N1 C2 N4 2.4(2) . . . . ?
C1 N1 C2 N4 -178.25(8) . . . . ?
C3 N1 C2 Ag1 -175.18(17) . . . . ?
C1 N1 C2 Ag1 4.2(2) . . . . ?
O3 Ag1 C2 N4 -6.0(6) . . . . ?
Ag2 Ag1 C2 N4 -93.24(19) . . . . ?
O3 Ag1 C2 N1 171.1(3) . . . . ?
Ag2 Ag1 C2 N1 83.80(18) . . . . ?
C2 N1 C3 N2 179.8(2) . . . . ?
C1 N1 C3 N2 0.4(3) . . . . ?
C2 N1 C3 C8 -1.8(2) . . . . ?
C1 N1 C3 C8 178.91(6) . . . . ?
C5 N2 C3 N1 179.5(2) . . . . ?
C4 N2 C3 N1 -5.6(4) . . . . ?
C5 N2 C3 C8 1.2(3) . . . . ?
C4 N2 C3 C8 176.1(2) . . . . ?
C7 N3 C5 O1 175.5(2) . . . . ?
C6 N3 C5 O1 -4.6(3) . . . . ?
C7 N3 C5 N2 -4.2(3) . . . . ?
C6 N3 C5 N2 175.67(17) . . . . ?
C3 N2 C5 O1 -179.3(2) . . . . ?
C4 N2 C5 O1 5.4(3) . . . . ?
C3 N2 C5 N3 0.4(3) . . . . ?
C4 N2 C5 N3 -174.8(2) . . . . ?
C5 N3 C7 O2 -174.6(2) . . . . ?
C6 N3 C7 O2 5.5(3) . . . . ?
C5 N3 C7 C8 5.8(3) . . . . ?
C6 N3 C7 C8 -174.12(15) . . . . ?
N1 C3 C8 N4 0.45(17) . . . . ?
N2 C3 C8 N4 179.08(16) . . . . ?
N1 C3 C8 C7 -177.87(14) . . . . ?
N2 C3 C8 C7 0.8(3) . . . . ?
C2 N4 C8 C3 1.07(15) . . . . ?
C9 N4 C8 C3 175.08(11) . . . . ?
C2 N4 C8 C7 179.19(19) . . . . ?
C9 N4 C8 C7 -6.79(14) . . . . ?
O2 C7 C8 C3 176.5(2) . . . . ?
N3 C7 C8 C3 -3.9(3) . . . . ?
O2 C7 C8 N4 -1.4(3) . . . . ?
N3 C7 C8 N4 178.22(7) . . . . ?
C2 N4 C9 C10 94.14(18) . . . . ?
C8 N4 C9 C10 -79.15(13) . . . . ?
N4 C9 C10 C11 -177.8(2) . . . . ?
C9 C10 C11 C12 -179.5(3) . . . . ?
Ag1 O3 C13 O4 2.9(3) . . . . ?
Ag1 O3 C13 C14 -176.69(8) . . . . ?
C22 N8 C16 N5 1.90(11) . . . . ?
C23 N8 C16 N5 178.36(13) . . . . ?
C22 N8 C16 Ag2 -178.74(11) . . . . ?
C23 N8 C16 Ag2 -2.28(13) . . . . ?
C17 N5 C16 N8 -2.0 . . . . ?
C15 N5 C16 N8 -178.34(14) . . . . ?
C17 N5 C16 Ag2 178.7 . . . . ?
C15 N5 C16 Ag2 2.32(14) . . . . ?
O7 Ag2 C16 N8 -119.5(3) . . . . ?
Ag1 Ag2 C16 N8 95.80(2) . . . . ?
O7 Ag2 C16 N5 59.7(3) . . . . ?
Ag1 Ag2 C16 N5 -84.98(2) . . . . ?
C16 N5 C17 C22 1.35(11) . . . . ?
C15 N5 C17 C22 177.32(19) . . . . ?
C16 N5 C17 N6 178.9 . . . . ?
C15 N5 C17 N6 -5.14(16) . . . . ?
C19 N6 C17 C22 -4.42(16) . . . . ?
C18 N6 C17 C22 177.29(12) . . . . ?
C19 N6 C17 N5 178.34(12) . . . . ?
C18 N6 C17 N5 0.0 . . . . ?
C21 N7 C19 O5 -176.7(2) . . . . ?
C20 N7 C19 O5 3.2(3) . . . . ?
C21 N7 C19 N6 3.0(3) . . . . ?
C20 N7 C19 N6 -177.12(17) . . . . ?
C17 N6 C19 O5 -177.60(18) . . . . ?
C18 N6 C19 O5 0.8(3) . . . . ?
C17 N6 C19 N7 2.8(2) . . . . ?
C18 N6 C19 N7 -178.83(12) . . . . ?
C19 N7 C21 O6 173.8(2) . . . . ?
C20 N7 C21 O6 -6.1(3) . . . . ?
C19 N7 C21 C22 -6.4(3) . . . . ?
C20 N7 C21 C22 173.71(19) . . . . ?
N5 C17 C22 N8 -0.17(17) . . . . ?
N6 C17 C22 N8 -177.96(7) . . . . ?
N5 C17 C22 C21 178.28(19) . . . . ?
N6 C17 C22 C21 0.5(3) . . . . ?
C16 N8 C22 C17 -1.12(18) . . . . ?
C23 N8 C22 C17 -177.56(14) . . . . ?
C16 N8 C22 C21 -179.4(2) . . . . ?
C23 N8 C22 C21 4.1(3) . . . . ?
O6 C21 C22 C17 -175.6(2) . . . . ?
N7 C21 C22 C17 4.6(3) . . . . ?
O6 C21 C22 N8 2.4(4) . . . . ?
N7 C21 C22 N8 -177.4(2) . . . . ?
C16 N8 C23 C24 -101.78(19) . . . . ?
C22 N8 C23 C24 74.2(3) . . . . ?
N8 C23 C24 C25 -172.8(2) . . . . ?
C23 C24 C25 C26 -179.7(3) . . . . ?
Ag2 O7 C27 O8 9.9(3) . . . . ?
Ag2 O7 C27 C28 -170.83(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.221
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.096
####################################################################### 
# 
# 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_Complex3d
_database_code_depnum_ccdc_archive 'CCDC 1037000'
_audit_update_record             
;
2014-12-01 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3d
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 Ag N4 O4'
_chemical_formula_sum            'C16 H17 Ag N4 O4'
_chemical_formula_weight         437.21

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.7170(6)
_cell_length_b                   9.9462(6)
_cell_length_c                   10.2712(9)
_cell_angle_alpha                82.181(6)
_cell_angle_beta                 86.063(6)
_cell_angle_gamma                67.816(6)
_cell_volume                     816.79(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    99.9(5)
_cell_measurement_reflns_used    3053
_cell_measurement_theta_min      3.5250
_cell_measurement_theta_max      30.2020

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    1.264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7861
_exptl_absorpt_correction_T_max  0.9280
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      99.9(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6438
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0853
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         28.28
_reflns_number_total             4023
_reflns_number_gt                3452
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_structure_refinement  
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material  
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;
_refine_special_details          
;
All H atoms were placed in calculated positions and refined using a riding model. C-H distances: CH3 0.98Α, aromatic 0.95Α.

All Uiso(H) values were constrained to be 1.2 times (1.5 times for methyl) Ueq of the parent atom.

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0191P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4023
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag -0.06603(3) 0.86483(3) 0.05082(3) 0.01453(9) Uani 1 1 d . . .
O1 O -0.0926(3) 1.3862(2) 0.5572(3) 0.0175(6) Uani 1 1 d . . .
O2 O 0.3413(3) 0.9822(2) 0.4483(3) 0.0186(6) Uani 1 1 d . . .
O3 O -0.1351(3) 0.7504(2) -0.0783(3) 0.0185(6) Uani 1 1 d . . .
O4 O 0.1366(3) 0.6418(3) -0.1007(3) 0.0232(6) Uani 1 1 d . . .
N1 N -0.1555(3) 1.0867(3) 0.2577(3) 0.0111(6) Uani 1 1 d . . .
N2 N -0.1494(3) 1.2475(3) 0.4223(3) 0.0116(6) Uani 1 1 d . . .
N3 N 0.1242(3) 1.1884(3) 0.4981(3) 0.0130(6) Uani 1 1 d . . .
N4 N 0.1061(3) 0.9519(3) 0.2550(3) 0.0111(6) Uani 1 1 d . . .
C1 C -0.3297(4) 1.1474(4) 0.2150(4) 0.0193(8) Uani 1 1 d . . .
H1A H -0.3404 1.0980 0.1418 0.029 Uiso 1 1 calc R . .
H1B H -0.3627 1.2524 0.1865 0.029 Uiso 1 1 calc R . .
H1C H -0.4015 1.1320 0.2885 0.029 Uiso 1 1 calc R . .
C2 C -0.0380(4) 0.9755(3) 0.1984(4) 0.0117(7) Uani 1 1 d . . .
C3 C -0.0818(4) 1.1369(3) 0.3445(4) 0.0109(7) Uani 1 1 d . . .
C4 C -0.3255(4) 1.3431(4) 0.4224(4) 0.0207(9) Uani 1 1 d . . .
H4A H -0.3517 1.4060 0.3383 0.031 Uiso 1 1 calc R . .
H4B H -0.3486 1.4040 0.4942 0.031 Uiso 1 1 calc R . .
H4C H -0.3936 1.2832 0.4346 0.031 Uiso 1 1 calc R . .
C5 C -0.0422(4) 1.2819(3) 0.4953(4) 0.0126(7) Uani 1 1 d . . .
C6 C 0.2321(4) 1.2294(4) 0.5762(4) 0.0175(8) Uani 1 1 d . . .
H6A H 0.2230 1.3296 0.5449 0.026 Uiso 1 1 calc R . .
H6B H 0.3473 1.1624 0.5665 0.026 Uiso 1 1 calc R . .
H6C H 0.1978 1.2232 0.6690 0.026 Uiso 1 1 calc R . .
C7 C 0.1974(4) 1.0651(3) 0.4309(4) 0.0123(7) Uani 1 1 d . . .
C8 C 0.0839(4) 1.0503(3) 0.3455(4) 0.0101(7) Uani 1 1 d . . .
C9 C 0.2646(4) 0.8552(3) 0.2070(4) 0.0123(7) Uani 1 1 d . . .
C10 C 0.3845(4) 0.9131(4) 0.1632(4) 0.0148(8) Uani 1 1 d . . .
H10 H 0.3666 1.0123 0.1699 0.018 Uiso 1 1 calc R . .
C11 C 0.5301(4) 0.8217(4) 0.1100(4) 0.0177(8) Uani 1 1 d . . .
H11 H 0.6142 0.8585 0.0812 0.021 Uiso 1 1 calc R . .
C12 C 0.5566(4) 0.6776(4) 0.0975(4) 0.0192(8) Uani 1 1 d . . .
H12 H 0.6576 0.6165 0.0603 0.023 Uiso 1 1 calc R . .
C13 C 0.4339(4) 0.6234(3) 0.1400(4) 0.0179(8) Uani 1 1 d . . .
H13 H 0.4506 0.5251 0.1308 0.021 Uiso 1 1 calc R . .
C14 C 0.2875(4) 0.7117(3) 0.1957(4) 0.0173(8) Uani 1 1 d . . .
H14 H 0.2041 0.6744 0.2257 0.021 Uiso 1 1 calc R . .
C15 C -0.0065(4) 0.6536(3) -0.1223(4) 0.0152(8) Uani 1 1 d . . .
C16 C -0.0369(5) 0.5487(4) -0.2014(4) 0.0283(10) Uani 1 1 d . . .
H16A H 0.0645 0.4975 -0.2502 0.042 Uiso 1 1 calc R . .
H16B H -0.1263 0.6033 -0.2633 0.042 Uiso 1 1 calc R . .
H16C H -0.0687 0.4773 -0.1419 0.042 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 C2 2.068(4) . ?
Ag1 O3 2.111(3) . ?
Ag1 Ag1 3.3249(5) 2_575 ?
O1 C5 1.213(4) . ?
O2 C7 1.223(4) . ?
O3 C15 1.273(4) . ?
O4 C15 1.240(4) . ?
N1 C2 1.373(4) . ?
N1 C3 1.378(4) . ?
N1 C1 1.480(4) . ?
N2 C3 1.371(4) . ?
N2 C5 1.400(5) . ?
N2 C4 1.469(4) . ?
N3 C5 1.396(4) . ?
N3 C7 1.403(4) . ?
N3 C6 1.475(4) . ?
N4 C2 1.346(4) . ?
N4 C8 1.393(4) . ?
N4 C9 1.453(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C8 1.375(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.425(5) . ?
C9 C14 1.385(5) . ?
C9 C10 1.395(4) . ?
C10 C11 1.380(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.513(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 Ag1 O3 168.94(11) . . ?
C2 Ag1 Ag1 65.18(9) . 2_575 ?
O3 Ag1 Ag1 123.36(7) . 2_575 ?
C15 O3 Ag1 110.0(2) . . ?
C2 N1 C3 110.2(3) . . ?
C2 N1 C1 120.8(3) . . ?
C3 N1 C1 128.6(3) . . ?
C3 N2 C5 118.2(3) . . ?
C3 N2 C4 123.8(3) . . ?
C5 N2 C4 117.6(3) . . ?
C5 N3 C7 126.5(3) . . ?
C5 N3 C6 115.4(3) . . ?
C7 N3 C6 118.0(3) . . ?
C2 N4 C8 110.9(3) . . ?
C2 N4 C9 122.4(3) . . ?
C8 N4 C9 125.6(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N4 C2 N1 105.6(3) . . ?
N4 C2 Ag1 125.3(2) . . ?
N1 C2 Ag1 129.1(2) . . ?
N2 C3 C8 122.5(3) . . ?
N2 C3 N1 130.4(3) . . ?
C8 C3 N1 107.1(3) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 N3 121.1(3) . . ?
O1 C5 N2 121.4(3) . . ?
N3 C5 N2 117.5(3) . . ?
N3 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 N3 121.8(3) . . ?
O2 C7 C8 126.3(3) . . ?
N3 C7 C8 111.9(3) . . ?
C3 C8 N4 106.1(3) . . ?
C3 C8 C7 122.6(3) . . ?
N4 C8 C7 131.3(3) . . ?
C14 C9 C10 121.8(3) . . ?
C14 C9 N4 119.2(3) . . ?
C10 C9 N4 118.8(3) . . ?
C11 C10 C9 117.9(3) . . ?
C11 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C10 C11 C12 121.7(3) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C13 119.3(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C9 C14 C13 118.9(3) . . ?
C9 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
O4 C15 O3 123.2(3) . . ?
O4 C15 C16 120.8(3) . . ?
O3 C15 C16 116.0(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 Ag1 O3 C15 -140.9(5) . . . . ?
Ag1 Ag1 O3 C15 80.6(2) 2_575 . . . ?
C8 N4 C2 N1 -2.6(4) . . . . ?
C9 N4 C2 N1 -171.6(3) . . . . ?
C8 N4 C2 Ag1 176.5(2) . . . . ?
C9 N4 C2 Ag1 7.5(4) . . . . ?
C3 N1 C2 N4 3.7(4) . . . . ?
C1 N1 C2 N4 177.0(3) . . . . ?
C3 N1 C2 Ag1 -175.4(2) . . . . ?
C1 N1 C2 Ag1 -2.1(4) . . . . ?
O3 Ag1 C2 N4 136.2(5) . . . . ?
Ag1 Ag1 C2 N4 -81.4(3) 2_575 . . . ?
O3 Ag1 C2 N1 -44.9(7) . . . . ?
Ag1 Ag1 C2 N1 97.5(3) 2_575 . . . ?
C5 N2 C3 C8 6.5(5) . . . . ?
C4 N2 C3 C8 179.2(3) . . . . ?
C5 N2 C3 N1 -175.6(3) . . . . ?
C4 N2 C3 N1 -2.9(5) . . . . ?
C2 N1 C3 N2 178.4(3) . . . . ?
C1 N1 C3 N2 5.8(6) . . . . ?
C2 N1 C3 C8 -3.4(4) . . . . ?
C1 N1 C3 C8 -176.0(3) . . . . ?
C7 N3 C5 O1 -179.9(3) . . . . ?
C6 N3 C5 O1 -2.4(5) . . . . ?
C7 N3 C5 N2 2.5(5) . . . . ?
C6 N3 C5 N2 180.0(3) . . . . ?
C3 N2 C5 O1 173.7(3) . . . . ?
C4 N2 C5 O1 0.6(5) . . . . ?
C3 N2 C5 N3 -8.6(4) . . . . ?
C4 N2 C5 N3 178.2(3) . . . . ?
C5 N3 C7 O2 -173.5(3) . . . . ?
C6 N3 C7 O2 9.0(5) . . . . ?
C5 N3 C7 C8 5.6(5) . . . . ?
C6 N3 C7 C8 -171.8(3) . . . . ?
N2 C3 C8 N4 -179.9(3) . . . . ?
N1 C3 C8 N4 1.7(4) . . . . ?
N2 C3 C8 C7 2.4(5) . . . . ?
N1 C3 C8 C7 -176.0(3) . . . . ?
C2 N4 C8 C3 0.6(4) . . . . ?
C9 N4 C8 C3 169.2(3) . . . . ?
C2 N4 C8 C7 178.0(3) . . . . ?
C9 N4 C8 C7 -13.4(5) . . . . ?
O2 C7 C8 C3 171.1(3) . . . . ?
N3 C7 C8 C3 -8.0(4) . . . . ?
O2 C7 C8 N4 -6.0(6) . . . . ?
N3 C7 C8 N4 174.9(3) . . . . ?
C2 N4 C9 C14 -55.7(5) . . . . ?
C8 N4 C9 C14 136.9(4) . . . . ?
C2 N4 C9 C10 119.1(4) . . . . ?
C8 N4 C9 C10 -48.3(5) . . . . ?
C14 C9 C10 C11 -1.3(6) . . . . ?
N4 C9 C10 C11 -175.8(3) . . . . ?
C9 C10 C11 C12 1.2(6) . . . . ?
C10 C11 C12 C13 -0.2(6) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C10 C9 C14 C13 0.3(6) . . . . ?
N4 C9 C14 C13 174.9(3) . . . . ?
C12 C13 C14 C9 0.7(6) . . . . ?
Ag1 O3 C15 O4 -6.7(4) . . . . ?
Ag1 O3 C15 C16 171.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.144
