# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_compound_I6
_database_code_depnum_ccdc_archive 'CCDC 1506155'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        N,N'-bis(isoquinolinecarboxamide)-1,6-hexane
_chemical_name_common            ?
_chemical_melting_point          425
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H26 N4 O2'
_chemical_formula_weight         426.50

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   12.7248(3)
_cell_length_b                   9.5216(2)
_cell_length_c                   18.8321(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2281.71(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2389
_cell_measurement_theta_min      4.6940
_cell_measurement_theta_max      73.5630

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.9478
_exptl_crystal_size_mid          0.1992
_exptl_crystal_size_min          0.1730
_exptl_absorpt_coefficient_mu    0.641
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            5409
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.696
_diffrn_reflns_theta_max         67.392
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2052
_reflns_number_gt                1802
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0731P)²+0.5405P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2052
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.82177(13) 0.14865(16) 0.63466(8) 0.0485(4) Uani 1 1 d . . . . .
C2 C 0.91976(13) 0.22269(15) 0.65904(8) 0.0474(4) Uani 1 1 d . . . . .
C3 C 1.02166(13) 0.17403(17) 0.63992(8) 0.0489(4) Uani 1 1 d . . . . .
C4 C 1.04089(15) 0.0645(2) 0.59093(10) 0.0616(5) Uani 1 1 d . . . . .
H4 H 0.9847 0.0218 0.5679 0.074 Uiso 1 1 calc R U . . .
C5 C 1.14065(18) 0.0208(3) 0.57706(14) 0.0842(7) Uani 1 1 d . . . . .
H5 H 1.1522 -0.0512 0.5446 0.101 Uiso 1 1 calc R U . . .
C6 C 1.22623(18) 0.0843(3) 0.61168(14) 0.0935(8) Uani 1 1 d . . . . .
H6 H 1.2940 0.0526 0.6026 0.112 Uiso 1 1 calc R U . . .
C7 C 1.21138(16) 0.1907(3) 0.65786(13) 0.0818(7) Uani 1 1 d . . . . .
H7 H 1.2690 0.2320 0.6799 0.098 Uiso 1 1 calc R U . . .
C8 C 1.10883(15) 0.2401(2) 0.67309(10) 0.0610(5) Uani 1 1 d . . . . .
C9 C 1.08901(18) 0.3506(2) 0.72012(11) 0.0729(6) Uani 1 1 d . . . . .
H9 H 1.1444 0.3958 0.7428 0.087 Uiso 1 1 calc R U . . .
C10 C 0.9894(2) 0.3912(2) 0.73226(11) 0.0774(6) Uani 1 1 d . . . . .
H10 H 0.9785 0.4667 0.7627 0.093 Uiso 1 1 calc R U . . .
C11 C 0.63506(13) 0.17309(18) 0.60907(10) 0.0593(5) Uani 1 1 d . . . . .
H11A H 0.5845 0.2489 0.6130 0.071 Uiso 1 1 calc R U . . .
H11B H 0.6197 0.1059 0.6464 0.071 Uiso 1 1 calc R U . . .
C12 C 0.62012(13) 0.1024(2) 0.53881(11) 0.0624(5) Uani 1 1 d . . . . .
H12A H 0.6698 0.0257 0.5343 0.075 Uiso 1 1 calc R U . . .
H12B H 0.6338 0.1689 0.5009 0.075 Uiso 1 1 calc R U . . .
C13 C 0.50848(14) 0.0458(2) 0.53179(12) 0.0642(5) Uani 1 1 d . . . . .
H13A H 0.4915 -0.0076 0.5742 0.077 Uiso 1 1 calc R U . . .
H13B H 0.4602 0.1245 0.5294 0.077 Uiso 1 1 calc R U . . .
N1 N 0.73948(11) 0.22983(14) 0.62094(8) 0.0546(4) Uani 1 1 d . . . . .
H1 H 0.7483 0.3193 0.6190 0.066 Uiso 1 1 calc R U . . .
N2 N 0.90285(13) 0.32849(15) 0.70269(8) 0.0629(4) Uani 1 1 d . . . . .
O1 O 0.81985(10) 0.01979(12) 0.63063(8) 0.0667(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2295(19) . ?
C1 N1 1.327(2) . ?
C1 C2 1.504(2) . ?
C2 N2 1.318(2) . ?
C2 C3 1.423(2) . ?
C3 C4 1.414(3) . ?
C3 C8 1.420(2) . ?
C4 C5 1.361(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.406(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.348(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.417(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.399(3) . ?
C9 C10 1.345(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.371(3) . ?
C10 H10 0.9300 . ?
C11 N1 1.452(2) . ?
C11 C12 1.497(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.525(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C13 1.497(4) 5_656 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
N1 H1 0.8600 . ?

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
O1 C1 N1 123.62(15) . . ?
O1 C1 C2 120.20(14) . . ?
N1 C1 C2 116.13(13) . . ?
N2 C2 C3 123.74(15) . . ?
N2 C2 C1 114.42(15) . . ?
C3 C2 C1 121.69(13) . . ?
C4 C3 C8 118.60(16) . . ?
C4 C3 C2 124.26(15) . . ?
C8 C3 C2 117.14(15) . . ?
C5 C4 C3 120.80(19) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 120.6(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 122.98(19) . . ?
C9 C8 C3 118.11(18) . . ?
C7 C8 C3 118.90(19) . . ?
C10 C9 C8 119.59(17) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 N2 124.27(18) . . ?
C9 C10 H10 117.9 . . ?
N2 C10 H10 117.9 . . ?
N1 C11 C12 114.83(15) . . ?
N1 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
N1 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.5 . . ?
C11 C12 C13 110.73(16) . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C13 C13 C12 114.2(2) 5_656 . ?
C13 C13 H13A 108.7 5_656 . ?
C12 C13 H13A 108.7 . . ?
C13 C13 H13B 108.7 5_656 . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C1 N1 C11 122.37(13) . . ?
C1 N1 H1 118.8 . . ?
C11 N1 H1 118.8 . . ?
C2 N2 C10 117.08(17) . . ?

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
O1 C1 C2 N2 -138.58(17) . . . . ?
N1 C1 C2 N2 39.1(2) . . . . ?
O1 C1 C2 C3 37.1(2) . . . . ?
N1 C1 C2 C3 -145.29(15) . . . . ?
N2 C2 C3 C4 -177.27(16) . . . . ?
C1 C2 C3 C4 7.5(2) . . . . ?
N2 C2 C3 C8 3.3(2) . . . . ?
C1 C2 C3 C8 -171.99(14) . . . . ?
C8 C3 C4 C5 1.6(3) . . . . ?
C2 C3 C4 C5 -177.89(19) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
C4 C5 C6 C7 -1.3(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 C9 -179.5(2) . . . . ?
C6 C7 C8 C3 1.2(3) . . . . ?
C4 C3 C8 C9 178.44(17) . . . . ?
C2 C3 C8 C9 -2.1(2) . . . . ?
C4 C3 C8 C7 -2.2(3) . . . . ?
C2 C3 C8 C7 177.29(17) . . . . ?
C7 C8 C9 C10 -179.6(2) . . . . ?
C3 C8 C9 C10 -0.3(3) . . . . ?
C8 C9 C10 N2 1.8(3) . . . . ?
N1 C11 C12 C13 179.63(15) . . . . ?
C11 C12 C13 C13 -170.9(2) . . . 5_656 ?
O1 C1 N1 C11 8.5(3) . . . . ?
C2 C1 N1 C11 -169.01(15) . . . . ?
C12 C11 N1 C1 -73.7(2) . . . . ?
C3 C2 N2 C10 -1.9(3) . . . . ?
C1 C2 N2 C10 173.70(16) . . . . ?
C9 C10 N2 C2 -0.8(3) . . . . ?

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-4




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_compound_I3-Ag
_database_code_depnum_ccdc_archive 'CCDC 1506159'
_audit_update_record             
;
2017-01-03 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        4b
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Ag, (C23 H20 N4 O2), (Cl O4), (H2 O)'
_chemical_formula_sum            'C23 H22 Ag Cl N4 O7'
_chemical_formula_weight         609.76

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'
Ag Ag 0.1306 4.2820 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5367(3)
_cell_length_b                   8.3723(3)
_cell_length_c                   19.4198(7)
_cell_angle_alpha                88.709(3)
_cell_angle_beta                 82.328(3)
_cell_angle_gamma                89.464(3)
_cell_volume                     1214.08(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14754
_cell_measurement_theta_min      4.5500
_cell_measurement_theta_max      73.4870

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.538
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.168
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_coefficient_mu    8.119
_exptl_absorpt_correction_T_min  0.109
_exptl_absorpt_correction_T_max  0.471
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            25518
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.596
_diffrn_reflns_theta_max         73.608
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4816
_reflns_number_gt                4554
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+0.4931P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0058(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4816
_refine_ls_number_parameters     380
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6800(4) 0.2982(3) 0.14234(13) 0.0428(5) Uani 1 1 d . . . . .
C2 C 0.6479(3) 0.1265(3) 0.12458(13) 0.0405(5) Uani 1 1 d . . . . .
C3 C 0.7048(3) 0.0703(3) 0.05735(13) 0.0423(5) Uani 1 1 d . . . . .
C4 C 0.7954(4) 0.1658(4) 0.00306(15) 0.0539(7) Uani 1 1 d . . . . .
H4 H 0.8197 0.2721 0.0108 0.065 Uiso 1 1 calc R U . . .
C5 C 0.8471(5) 0.1031(5) -0.06043(17) 0.0664(8) Uani 1 1 d . . . . .
H5 H 0.9087 0.1666 -0.0955 0.080 Uiso 1 1 calc R U . . .
C6 C 0.8095(5) -0.0544(5) -0.07385(17) 0.0676(9) Uani 1 1 d . . . . .
H6 H 0.8425 -0.0940 -0.1181 0.081 Uiso 1 1 calc R U . . .
C7 C 0.7249(5) -0.1513(4) -0.02278(17) 0.0599(7) Uani 1 1 d . . . . .
H7 H 0.7022 -0.2571 -0.0321 0.072 Uiso 1 1 calc R U . . .
C8 C 0.6714(4) -0.0919(3) 0.04417(15) 0.0470(6) Uani 1 1 d . . . . .
C9 C 0.5830(4) -0.1854(3) 0.09933(16) 0.0533(7) Uani 1 1 d . . . . .
H9 H 0.5603 -0.2926 0.0927 0.064 Uiso 1 1 calc R U . . .
C10 C 0.5313(5) -0.1197(3) 0.16166(16) 0.0549(7) Uani 1 1 d . . . . .
H10 H 0.4713 -0.1835 0.1969 0.066 Uiso 1 1 calc R U . . .
C11 C 0.8189(4) 0.4695(3) 0.22068(16) 0.0534(7) Uani 1 1 d . . . . .
H11A H 0.8207 0.4583 0.2704 0.064 Uiso 1 1 calc R U . . .
H11B H 0.7242 0.5446 0.2133 0.064 Uiso 1 1 calc R U . . .
C12 C 0.9956(5) 0.5374(3) 0.18760(15) 0.0552(7) Uani 1 1 d . . . . .
H12A H 1.0109 0.6408 0.2075 0.066 Uiso 1 1 calc R U . . .
H12B H 0.9899 0.5549 0.1384 0.066 Uiso 1 1 calc R U . . .
C13 C 1.1595(4) 0.4361(4) 0.19551(14) 0.0553(7) Uani 1 1 d . . . . .
H13A H 1.1521 0.3377 0.1706 0.066 Uiso 1 1 calc R U . . .
H13B H 1.2650 0.4928 0.1741 0.066 Uiso 1 1 calc R U . . .
C14 C 1.2892(4) 0.4729(3) 0.30383(13) 0.0434(5) Uani 1 1 d . . . . .
C15 C 1.3071(3) 0.3986(3) 0.37432(13) 0.0419(5) Uani 1 1 d . . . . .
C16 C 1.2662(4) 0.4851(3) 0.43616(13) 0.0438(5) Uani 1 1 d . . . . .
C17 C 1.2003(4) 0.6444(4) 0.43717(17) 0.0541(7) Uani 1 1 d . . . . .
H17 H 1.1811 0.6968 0.3961 0.065 Uiso 1 1 calc R U . . .
C18 C 1.1652(5) 0.7196(5) 0.4990(2) 0.0665(8) Uani 1 1 d . . . . .
H18 H 1.1217 0.8240 0.4999 0.080 Uiso 1 1 calc R U . . .
C19 C 1.1940(5) 0.6417(5) 0.56169(18) 0.0689(9) Uani 1 1 d . . . . .
H19 H 1.1721 0.6962 0.6032 0.083 Uiso 1 1 calc R U . . .
C20 C 1.2533(5) 0.4885(4) 0.56218(16) 0.0621(8) Uani 1 1 d . . . . .
H20 H 1.2694 0.4377 0.6040 0.074 Uiso 1 1 calc R U . . .
C21 C 1.2904(4) 0.4061(4) 0.49951(14) 0.0504(6) Uani 1 1 d . . . . .
C22 C 1.3482(5) 0.2464(4) 0.49723(15) 0.0603(8) Uani 1 1 d . . . . .
H22 H 1.3613 0.1905 0.5382 0.072 Uiso 1 1 calc R U . . .
C23 C 1.3850(5) 0.1737(4) 0.43514(15) 0.0591(7) Uani 1 1 d . . . . .
H23 H 1.4250 0.0683 0.4347 0.071 Uiso 1 1 calc R U . . .
Ag1 Ag 0.46021(3) 0.11776(2) 0.27924(2) 0.05348(12) Uani 1 1 d . . . . .
N1 N 0.5627(3) 0.0358(3) 0.17551(11) 0.0464(5) Uani 1 1 d . . . . .
N2 N 0.7773(3) 0.3151(3) 0.19385(12) 0.0471(5) Uani 1 1 d . . . . .
H2 H 0.8179 0.2304 0.2124 0.057 Uiso 1 1 calc R U . . .
N3 N 1.1810(3) 0.3963(3) 0.26770(12) 0.0503(5) Uani 1 1 d . . . . .
H3 H 1.1196 0.3184 0.2879 0.060 Uiso 1 1 calc R U . . .
N4 N 1.3658(3) 0.2488(3) 0.37322(12) 0.0488(5) Uani 1 1 d . . . . .
O1 O 0.6187(4) 0.4085(2) 0.11035(12) 0.0676(6) Uani 1 1 d . . . . .
O2 O 1.3725(3) 0.5934(3) 0.28288(11) 0.0601(5) Uani 1 1 d . . . . .
O1W O 0.5275(3) -0.1459(3) 0.34135(13) 0.0636(5) Uani 1 1 d D . . . .
Cl1 Cl 0.9860(7) -0.0303(7) 0.3065(3) 0.0663(12) Uani 0.615(9) 1 d D . P A 1
O3 O 0.9023(12) -0.1689(7) 0.3050(6) 0.139(5) Uani 0.615(9) 1 d D . P A 1
O4 O 0.8918(17) 0.1038(9) 0.2999(6) 0.159(5) Uani 0.615(9) 1 d D . P A 1
O5 O 1.1269(19) -0.0268(18) 0.2507(7) 0.252(10) Uani 0.615(9) 1 d D . P A 1
O6 O 1.0611(16) -0.0153(11) 0.3668(5) 0.188(5) Uani 0.615(9) 1 d D . P A 1
Cl1A Cl 0.9929(8) -0.0353(8) 0.2892(4) 0.0466(11) Uani 0.385(9) 1 d D . P A 2
O3A O 0.9146(18) -0.1505(16) 0.3355(8) 0.169(10) Uani 0.385(9) 1 d D . P A 2
O4A O 0.953(2) 0.1161(13) 0.3138(8) 0.146(8) Uani 0.385(9) 1 d D . P A 2
O5A O 1.1685(9) -0.0662(14) 0.2763(8) 0.140(7) Uani 0.385(9) 1 d D . P A 2
O6A O 0.9125(17) -0.0496(15) 0.2292(6) 0.142(6) Uani 0.385(9) 1 d D . P A 2
H1W H 0.657(3) -0.152(9) 0.327(4) 0.16(3) Uiso 1 1 d D . . . .
H2W H 0.475(6) -0.238(4) 0.325(3) 0.106(17) 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
C1 O1 1.223(3) . ?
C1 N2 1.328(3) . ?
C1 C2 1.514(3) . ?
C2 N1 1.332(3) . ?
C2 C3 1.409(4) . ?
C3 C4 1.413(4) . ?
C3 C8 1.419(4) . ?
C4 C5 1.358(5) . ?
C5 C6 1.389(5) . ?
C6 C7 1.361(5) . ?
C7 C8 1.409(4) . ?
C8 C9 1.409(4) . ?
C9 C10 1.349(4) . ?
C10 N1 1.364(4) . ?
C11 N2 1.457(4) . ?
C11 C12 1.510(5) . ?
C12 C13 1.514(5) . ?
C13 N3 1.464(3) . ?
C14 O2 1.226(3) . ?
C14 N3 1.323(4) . ?
C14 C15 1.513(3) . ?
C15 N4 1.326(3) . ?
C15 C16 1.414(4) . ?
C16 C21 1.416(4) . ?
C16 C17 1.418(4) . ?
C17 C18 1.362(5) . ?
C18 C19 1.409(6) . ?
C19 C20 1.355(5) . ?
C20 C21 1.407(4) . ?
C21 C22 1.402(4) . ?
C22 C23 1.357(4) . ?
C23 N4 1.369(4) . ?
Ag1 N1 2.182(2) . ?
Ag1 N4 2.184(2) 1_455 ?
Ag1 O1W 2.571(2) . ?
N4 Ag1 2.184(2) 1_655 ?
Cl1 O3 1.328(7) . ?
Cl1 O4 1.336(8) . ?
Cl1 O6 1.376(8) . ?
Cl1 O5 1.413(9) . ?
Cl1A O5A 1.338(8) . ?
Cl1A O4A 1.380(10) . ?
Cl1A O3A 1.384(9) . ?
Cl1A O6A 1.392(10) . ?

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
O1 C1 N2 124.8(3) . . ?
O1 C1 C2 120.6(2) . . ?
N2 C1 C2 114.6(2) . . ?
N1 C2 C3 123.3(2) . . ?
N1 C2 C1 116.1(2) . . ?
C3 C2 C1 120.6(2) . . ?
C2 C3 C4 123.6(3) . . ?
C2 C3 C8 117.8(2) . . ?
C4 C3 C8 118.6(2) . . ?
C5 C4 C3 120.3(3) . . ?
C4 C5 C6 121.1(3) . . ?
C7 C6 C5 120.6(3) . . ?
C6 C7 C8 120.2(3) . . ?
C7 C8 C9 123.2(3) . . ?
C7 C8 C3 119.2(3) . . ?
C9 C8 C3 117.6(2) . . ?
C10 C9 C8 120.1(3) . . ?
C9 C10 N1 123.3(3) . . ?
N2 C11 C12 113.8(2) . . ?
C11 C12 C13 115.8(3) . . ?
N3 C13 C12 114.0(2) . . ?
O2 C14 N3 124.1(2) . . ?
O2 C14 C15 121.1(2) . . ?
N3 C14 C15 114.8(2) . . ?
N4 C15 C16 123.2(2) . . ?
N4 C15 C14 115.0(2) . . ?
C16 C15 C14 121.8(2) . . ?
C15 C16 C21 117.5(2) . . ?
C15 C16 C17 123.0(2) . . ?
C21 C16 C17 119.5(3) . . ?
C18 C17 C16 119.3(3) . . ?
C17 C18 C19 121.0(3) . . ?
C20 C19 C18 120.8(3) . . ?
C19 C20 C21 120.1(3) . . ?
C22 C21 C20 122.4(3) . . ?
C22 C21 C16 118.2(3) . . ?
C20 C21 C16 119.4(3) . . ?
C23 C22 C21 119.9(3) . . ?
C22 C23 N4 122.8(3) . . ?
N1 Ag1 N4 168.18(8) . 1_455 ?
N1 Ag1 O1W 94.83(8) . . ?
N4 Ag1 O1W 96.27(8) 1_455 . ?
C2 N1 C10 118.0(2) . . ?
C2 N1 Ag1 125.18(18) . . ?
C10 N1 Ag1 116.83(19) . . ?
C1 N2 C11 123.5(2) . . ?
C14 N3 C13 124.0(2) . . ?
C15 N4 C23 118.3(2) . . ?
C15 N4 Ag1 124.96(18) . 1_655 ?
C23 N4 Ag1 116.48(19) . 1_655 ?
O3 Cl1 O4 118.0(7) . . ?
O3 Cl1 O6 111.7(7) . . ?
O4 Cl1 O6 105.6(6) . . ?
O3 Cl1 O5 107.7(7) . . ?
O4 Cl1 O5 105.8(8) . . ?
O6 Cl1 O5 107.4(8) . . ?
O5A Cl1A O4A 113.7(8) . . ?
O5A Cl1A O3A 108.5(8) . . ?
O4A Cl1A O3A 110.8(9) . . ?
O5A Cl1A O6A 110.6(8) . . ?
O4A Cl1A O6A 107.0(8) . . ?
O3A Cl1A O6A 105.8(8) . . ?

_refine_diff_density_max         0.647
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol water 50/50'
####################################################################### 
# 
# 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_compound_I2
_database_code_depnum_ccdc_archive 'CCDC 1506153'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
N,N'-bis(1-isoquinolinecarboxamide)-1,2-ethane
_chemical_name_common            ?
_chemical_melting_point          431
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 N4 O2'
_chemical_formula_weight         370.40

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'

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

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

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

_cell_length_a                   19.2319(8)
_cell_length_b                   13.1155(2)
_cell_length_c                   9.2503(4)
_cell_angle_alpha                90
_cell_angle_beta                 128.558(6)
_cell_angle_gamma                90
_cell_volume                     1824.55(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3437
_cell_measurement_theta_min      4.4380
_cell_measurement_theta_max      73.1610

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3258
_exptl_crystal_size_mid          0.2650
_exptl_crystal_size_min          0.1744
_exptl_absorpt_coefficient_mu    0.721
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  1.254
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            5172
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.473
_diffrn_reflns_theta_max         73.086
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1787
_reflns_number_gt                1676
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0707P)²+0.5199P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1787
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.10974(7) 0.07477(8) 0.34283(14) 0.0316(3) Uani 1 1 d . . . . .
C2 C 0.14831(7) 0.16392(8) 0.47572(14) 0.0312(3) Uani 1 1 d . . . . .
C3 C 0.13572(7) 0.26697(8) 0.41256(15) 0.0322(3) Uani 1 1 d . . . . .
C4 C 0.08374(8) 0.29694(10) 0.22492(17) 0.0412(3) Uani 1 1 d . . . . .
H4 H 0.0553 0.2478 0.1322 0.049 Uiso 1 1 calc R U . . .
C5 C 0.07518(10) 0.39768(11) 0.1797(2) 0.0528(4) Uani 1 1 d . . . . .
H5 H 0.0407 0.4166 0.0560 0.063 Uiso 1 1 calc R U . . .
C6 C 0.11753(11) 0.47310(10) 0.3170(2) 0.0559(4) Uani 1 1 d . . . . .
H6 H 0.1112 0.5413 0.2833 0.067 Uiso 1 1 calc R U . . .
C7 C 0.16760(9) 0.44772(10) 0.4981(2) 0.0490(3) Uani 1 1 d . . . . .
H7 H 0.1957 0.4984 0.5880 0.059 Uiso 1 1 calc R U . . .
C8 C 0.17723(7) 0.34409(9) 0.55071(17) 0.0371(3) Uani 1 1 d . . . . .
C9 C 0.22681(8) 0.31454(10) 0.73703(18) 0.0441(3) Uani 1 1 d . . . . .
H9 H 0.2555 0.3633 0.8304 0.053 Uiso 1 1 calc R U . . .
C10 C 0.23229(9) 0.21436(11) 0.77907(17) 0.0464(3) Uani 1 1 d . . . . .
H10 H 0.2644 0.1963 0.9027 0.056 Uiso 1 1 calc R U . . .
C11 C 0.04853(8) -0.09706(8) 0.28957(16) 0.0352(3) Uani 1 1 d . . . . .
H11A H 0.0774 -0.1582 0.3628 0.042 Uiso 1 1 calc R U . . .
H11B H 0.0518 -0.0980 0.1891 0.042 Uiso 1 1 calc R U . . .
N1 N 0.09486(6) -0.00816(7) 0.40384(12) 0.0342(3) Uani 1 1 d . . . . .
H1 H 0.1136 -0.0088 0.5160 0.041 Uiso 1 1 calc R U . . .
N2 N 0.19351(7) 0.13897(8) 0.65079(13) 0.0399(3) Uani 1 1 d . . . . .
O1 O 0.09438(7) 0.07983(7) 0.19285(12) 0.0456(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2269(14) . ?
C1 N1 1.3360(14) . ?
C1 C2 1.5138(15) . ?
C2 N2 1.3155(14) . ?
C2 C3 1.4319(15) . ?
C3 C4 1.4154(17) . ?
C3 C8 1.4218(16) . ?
C4 C5 1.3645(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.354(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.4164(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.4076(18) . ?
C9 C10 1.3557(19) . ?
C9 H9 0.9300 . ?
C10 N2 1.3560(15) . ?
C10 H10 0.9300 . ?
C11 N1 1.4480(14) . ?
C11 C11 1.522(2) 2 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
N1 H1 0.8600 . ?

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
O1 C1 N1 123.89(10) . . ?
O1 C1 C2 121.82(10) . . ?
N1 C1 C2 114.29(9) . . ?
N2 C2 C3 123.44(10) . . ?
N2 C2 C1 114.89(10) . . ?
C3 C2 C1 121.67(9) . . ?
C4 C3 C8 118.45(11) . . ?
C4 C3 C2 124.96(10) . . ?
C8 C3 C2 116.57(10) . . ?
C5 C4 C3 120.17(12) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.99(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 120.72(13) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.05(12) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C9 C8 C7 121.90(11) . . ?
C9 C8 C3 118.49(11) . . ?
C7 C8 C3 119.60(11) . . ?
C10 C9 C8 119.36(11) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 N2 123.62(11) . . ?
C9 C10 H10 118.2 . . ?
N2 C10 H10 118.2 . . ?
N1 C11 C11 111.30(8) . 2 ?
N1 C11 H11A 109.4 . . ?
C11 C11 H11A 109.4 2 . ?
N1 C11 H11B 109.4 . . ?
C11 C11 H11B 109.4 2 . ?
H11A C11 H11B 108.0 . . ?
C1 N1 C11 122.93(9) . . ?
C1 N1 H1 118.5 . . ?
C11 N1 H1 118.5 . . ?
C2 N2 C10 118.49(10) . . ?

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
O1 C1 C2 N2 -153.90(11) . . . . ?
N1 C1 C2 N2 25.78(14) . . . . ?
O1 C1 C2 C3 26.08(16) . . . . ?
N1 C1 C2 C3 -154.24(10) . . . . ?
N2 C2 C3 C4 -176.54(11) . . . . ?
C1 C2 C3 C4 3.48(17) . . . . ?
N2 C2 C3 C8 1.73(16) . . . . ?
C1 C2 C3 C8 -178.25(9) . . . . ?
C8 C3 C4 C5 0.85(18) . . . . ?
C2 C3 C4 C5 179.08(12) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C7 -0.4(2) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C6 C7 C8 C9 -178.38(13) . . . . ?
C6 C7 C8 C3 1.4(2) . . . . ?
C4 C3 C8 C9 178.18(11) . . . . ?
C2 C3 C8 C9 -0.20(16) . . . . ?
C4 C3 C8 C7 -1.64(17) . . . . ?
C2 C3 C8 C7 179.98(10) . . . . ?
C7 C8 C9 C10 178.68(12) . . . . ?
C3 C8 C9 C10 -1.13(19) . . . . ?
C8 C9 C10 N2 1.2(2) . . . . ?
O1 C1 N1 C11 -8.00(18) . . . . ?
C2 C1 N1 C11 172.34(9) . . . . ?
C11 C11 N1 C1 -98.88(14) 2 . . . ?
C3 C2 N2 C10 -1.80(18) . . . . ?
C1 C2 N2 C10 178.18(10) . . . . ?
C9 C10 N2 C2 0.3(2) . . . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.119

_shelxl_version_number           2013-4




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_compound_I4
_database_code_depnum_ccdc_archive 'CCDC 1506154'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        N,N'-bis(isoquinolinecarboxamide)-1,4-buthane
_chemical_name_common            ?
_chemical_melting_point          428
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N4 O2'
_chemical_formula_weight         398.46

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'

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

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

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

_cell_length_a                   8.23260(10)
_cell_length_b                   12.4302(2)
_cell_length_c                   9.8859(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.960(2)
_cell_angle_gamma                90
_cell_volume                     985.88(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3557
_cell_measurement_theta_min      3.5090
_cell_measurement_theta_max      73.0150

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4869
_exptl_crystal_size_mid          0.1933
_exptl_crystal_size_min          0.1192
_exptl_absorpt_coefficient_mu    0.704
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_T_max  1.086
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            5665
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         5.514
_diffrn_reflns_theta_max         73.113
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1925
_reflns_number_gt                1802
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0576P)²+0.0976P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0086(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1925
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.91803(12) 0.69873(7) 0.08401(7) 0.0561(3) Uani 1 1 d . . . . .
N1 N 0.90548(12) 0.77127(7) -0.12636(8) 0.0440(2) Uani 1 1 d . . . . .
H1 H 0.8609 0.7682 -0.2137 0.053 Uiso 1 1 calc R U . . .
N2 N 0.67805(12) 0.63080(8) -0.24501(9) 0.0474(3) Uani 1 1 d . . . . .
C1 C 0.86695(13) 0.69615(8) -0.04259(10) 0.0397(2) Uani 1 1 d . . . . .
C2 C 0.75378(12) 0.60755(8) -0.11627(10) 0.0391(2) Uani 1 1 d . . . . .
C3 C 0.72862(12) 0.50874(8) -0.04944(11) 0.0404(3) Uani 1 1 d . . . . .
C4 C 0.81372(15) 0.47804(9) 0.08582(11) 0.0494(3) Uani 1 1 d . . . . .
H4 H 0.8957 0.5226 0.1370 0.059 Uiso 1 1 calc R U . . .
C8 C 0.60846(13) 0.43670(8) -0.12704(12) 0.0463(3) Uani 1 1 d . . . . .
C10 C 0.56808(15) 0.55901(10) -0.31752(12) 0.0550(3) Uani 1 1 d . . . . .
H10 H 0.5167 0.5752 -0.4090 0.066 Uiso 1 1 calc R U . . .
C9 C 0.52930(14) 0.46482(9) -0.26330(13) 0.0539(3) Uani 1 1 d . . . . .
H9 H 0.4506 0.4191 -0.3162 0.065 Uiso 1 1 calc R U . . .
C7 C 0.57098(16) 0.34013(10) -0.06402(15) 0.0589(3) Uani 1 1 d . . . . .
H7 H 0.4903 0.2937 -0.1130 0.071 Uiso 1 1 calc R U . . .
C5 C 0.77579(18) 0.38303(10) 0.14143(14) 0.0598(3) Uani 1 1 d . . . . .
H5 H 0.8331 0.3633 0.2300 0.072 Uiso 1 1 calc R U . . .
C6 C 0.65192(19) 0.31517(10) 0.06687(16) 0.0633(4) Uani 1 1 d . . . . .
H6 H 0.6250 0.2522 0.1078 0.076 Uiso 1 1 calc R U . . .
C11 C 1.02039(13) 0.85809(8) -0.07460(11) 0.0431(3) Uani 1 1 d . . . . .
H11A H 1.0729 0.8814 -0.1482 0.052 Uiso 1 1 calc R U . . .
H11B H 1.1073 0.8310 0.0008 0.052 Uiso 1 1 calc R U . . .
C12 C 0.93858(12) 0.95420(8) -0.02316(11) 0.0427(3) Uani 1 1 d . . . . .
H12A H 0.8915 0.9322 0.0541 0.051 Uiso 1 1 calc R U . . .
H12B H 0.8481 0.9796 -0.0968 0.051 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2281(12) . ?
N1 C1 1.3326(13) . ?
N1 C11 1.4507(13) . ?
N1 H1 0.8600 . ?
N2 C2 1.3175(13) . ?
N2 C10 1.3560(15) . ?
C1 C2 1.5189(14) . ?
C2 C3 1.4316(14) . ?
C3 C4 1.4157(15) . ?
C3 C8 1.4242(15) . ?
C4 C5 1.3680(16) . ?
C4 H4 0.9300 . ?
C8 C9 1.4028(17) . ?
C8 C7 1.4180(16) . ?
C10 C9 1.3552(18) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C7 C6 1.352(2) . ?
C7 H7 0.9300 . ?
C5 C6 1.399(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C11 C12 1.5142(14) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C12 1.5236(19) 3_775 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 121.96(8) . . ?
C1 N1 H1 119.0 . . ?
C11 N1 H1 119.0 . . ?
C2 N2 C10 118.79(10) . . ?
O1 C1 N1 122.70(9) . . ?
O1 C1 C2 122.73(9) . . ?
N1 C1 C2 114.58(8) . . ?
N2 C2 C3 123.22(9) . . ?
N2 C2 C1 114.25(9) . . ?
C3 C2 C1 122.51(9) . . ?
C4 C3 C8 118.43(10) . . ?
C4 C3 C2 125.10(10) . . ?
C8 C3 C2 116.47(10) . . ?
C5 C4 C3 120.21(11) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C9 C8 C7 122.20(11) . . ?
C9 C8 C3 118.53(10) . . ?
C7 C8 C3 119.27(11) . . ?
C9 C10 N2 123.23(11) . . ?
C9 C10 H10 118.4 . . ?
N2 C10 H10 118.4 . . ?
C10 C9 C8 119.68(10) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C6 C7 C8 120.38(12) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C4 C5 C6 120.92(12) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 120.69(11) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N1 C11 C12 113.66(8) . . ?
N1 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
N1 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C12 112.04(10) . 3_775 ?
C11 C12 H12A 109.2 . . ?
C12 C12 H12A 109.2 3_775 . ?
C11 C12 H12B 109.2 . . ?
C12 C12 H12B 109.2 3_775 . ?
H12A C12 H12B 107.9 . . ?

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
C11 N1 C1 O1 4.31(16) . . . . ?
C11 N1 C1 C2 -176.11(9) . . . . ?
C10 N2 C2 C3 1.41(16) . . . . ?
C10 N2 C2 C1 -176.87(9) . . . . ?
O1 C1 C2 N2 163.73(10) . . . . ?
N1 C1 C2 N2 -15.86(13) . . . . ?
O1 C1 C2 C3 -14.57(15) . . . . ?
N1 C1 C2 C3 165.85(9) . . . . ?
N2 C2 C3 C4 176.48(10) . . . . ?
C1 C2 C3 C4 -5.38(15) . . . . ?
N2 C2 C3 C8 -3.30(15) . . . . ?
C1 C2 C3 C8 174.84(8) . . . . ?
C8 C3 C4 C5 -2.41(16) . . . . ?
C2 C3 C4 C5 177.81(10) . . . . ?
C4 C3 C8 C9 -177.24(9) . . . . ?
C2 C3 C8 C9 2.56(14) . . . . ?
C4 C3 C8 C7 3.65(15) . . . . ?
C2 C3 C8 C7 -176.55(9) . . . . ?
C2 N2 C10 C9 1.30(18) . . . . ?
N2 C10 C9 C8 -1.91(19) . . . . ?
C7 C8 C9 C10 178.92(11) . . . . ?
C3 C8 C9 C10 -0.16(16) . . . . ?
C9 C8 C7 C6 178.99(11) . . . . ?
C3 C8 C7 C6 -1.93(17) . . . . ?
C3 C4 C5 C6 -0.59(18) . . . . ?
C8 C7 C6 C5 -1.11(19) . . . . ?
C4 C5 C6 C7 2.43(19) . . . . ?
C1 N1 C11 C12 -86.00(12) . . . . ?
N1 C11 C12 C12 -176.99(10) . . . 3_775 ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_compound_I5
_database_code_depnum_ccdc_archive 'CCDC 1506156'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        N,N'-bis(isoquinolinecarboxamide)-1,5-pentane
_chemical_name_common            ?
_chemical_melting_point          412
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H24 N4 O2'
_chemical_formula_weight         412.48

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   13.4447(4)
_cell_length_b                   8.7623(2)
_cell_length_c                   17.9862(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2118.89(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4454
_cell_measurement_theta_min      4.8840
_cell_measurement_theta_max      73.6240

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3264
_exptl_crystal_size_mid          0.1202
_exptl_crystal_size_min          0.0829
_exptl_absorpt_coefficient_mu    0.673
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            9569
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.918
_diffrn_reflns_theta_max         73.435
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2108
_reflns_number_gt                1907
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0534P)²+0.4469P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2108
_refine_ls_number_parameters     142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.18246(8) 0.47223(13) 0.11545(6) 0.0371(3) Uani 1 1 d . . . . .
C2 C 0.11108(8) 0.58000(12) 0.07772(6) 0.0355(3) Uani 1 1 d . . . . .
C3 C 0.00870(9) 0.58431(13) 0.09879(6) 0.0379(3) Uani 1 1 d . . . . .
C4 C -0.03348(10) 0.49264(18) 0.15512(8) 0.0525(4) Uani 1 1 d . . . . .
H4 H 0.0054 0.4203 0.1793 0.063 Uiso 1 1 calc R U . . .
C5 C -0.13088(11) 0.5098(3) 0.17415(10) 0.0730(5) Uani 1 1 d . . . . .
H5 H -0.1579 0.4498 0.2117 0.088 Uiso 1 1 calc R U . . .
C6 C -0.19072(12) 0.6173(3) 0.13760(10) 0.0794(6) Uani 1 1 d . . . . .
H6 H -0.2570 0.6279 0.1515 0.095 Uiso 1 1 calc R U . . .
C7 C -0.15382(11) 0.7056(2) 0.08258(9) 0.0645(4) Uani 1 1 d . . . . .
H7 H -0.1948 0.7751 0.0583 0.077 Uiso 1 1 calc R U . . .
C8 C -0.05244(9) 0.69208(15) 0.06191(7) 0.0450(3) Uani 1 1 d . . . . .
C9 C -0.00937(11) 0.78298(16) 0.00647(8) 0.0536(4) Uani 1 1 d . . . . .
H9 H -0.0479 0.8532 -0.0195 0.064 Uiso 1 1 calc R U . . .
C10 C 0.08864(11) 0.76784(17) -0.00894(8) 0.0562(4) Uani 1 1 d . . . . .
H10 H 0.1156 0.8292 -0.0460 0.067 Uiso 1 1 calc R U . . .
C11 C 0.34444(9) 0.44221(15) 0.17361(8) 0.0476(3) Uani 1 1 d . . . . .
H11A H 0.3765 0.3756 0.1378 0.057 Uiso 1 1 calc R U . . .
H11B H 0.3124 0.3784 0.2106 0.057 Uiso 1 1 calc R U . . .
C12 C 0.42186(10) 0.53806(15) 0.21079(8) 0.0492(3) Uani 1 1 d . . . . .
H12A H 0.3899 0.6046 0.2467 0.059 Uiso 1 1 calc R U . . .
H12B H 0.4539 0.6019 0.1738 0.059 Uiso 1 1 calc R U . . .
C13 C 0.5000 0.4435(2) 0.2500 0.0453(4) Uani 1 2 d S T P . .
H13A H 0.4675 0.3782 0.2862 0.054 Uiso 0.5 1 calc R U P . .
H13B H 0.5325 0.3782 0.2138 0.054 Uiso 0.5 1 calc R U P . .
N1 N 0.26899(7) 0.53226(11) 0.13567(6) 0.0425(3) Uani 1 1 d . . . . .
H1 H 0.2807 0.6267 0.1261 0.051 Uiso 1 1 calc R U . . .
N2 N 0.15016(8) 0.66823(12) 0.02658(6) 0.0460(3) Uani 1 1 d . . . . .
O1 O 0.15948(7) 0.33902(10) 0.12771(6) 0.0530(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.2274(15) . ?
C1 N1 1.3276(15) . ?
C1 C2 1.5077(15) . ?
C2 N2 1.3114(16) . ?
C2 C3 1.4282(16) . ?
C3 C4 1.4118(18) . ?
C3 C8 1.4169(17) . ?
C4 C5 1.362(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.351(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.4177(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.401(2) . ?
C9 C10 1.353(2) . ?
C9 H9 0.9300 . ?
C10 N2 1.3616(17) . ?
C10 H10 0.9300 . ?
C11 N1 1.4550(15) . ?
C11 C12 1.4954(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.5125(15) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C12 1.5125(15) 4_655 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
N1 H1 0.8600 . ?

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
O1 C1 N1 123.24(11) . . ?
O1 C1 C2 121.08(10) . . ?
N1 C1 C2 115.65(10) . . ?
N2 C2 C3 123.82(11) . . ?
N2 C2 C1 115.46(10) . . ?
C3 C2 C1 120.70(10) . . ?
C4 C3 C8 118.82(12) . . ?
C4 C3 C2 124.23(11) . . ?
C8 C3 C2 116.91(11) . . ?
C5 C4 C3 120.26(14) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.53(16) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 121.17(14) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.82(14) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C9 C8 C3 118.17(12) . . ?
C9 C8 C7 122.43(13) . . ?
C3 C8 C7 119.39(13) . . ?
C10 C9 C8 119.50(12) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 N2 123.94(13) . . ?
C9 C10 H10 118.0 . . ?
N2 C10 H10 118.0 . . ?
N1 C11 C12 112.98(10) . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 C13 112.60(11) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C12 113.56(15) 4_655 . ?
C12 C13 H13A 108.9 4_655 . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 4_655 . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C1 N1 C11 121.63(10) . . ?
C1 N1 H1 119.2 . . ?
C11 N1 H1 119.2 . . ?
C2 N2 C10 117.62(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N2 -137.00(13) . . . . ?
N1 C1 C2 N2 44.69(15) . . . . ?
O1 C1 C2 C3 44.11(17) . . . . ?
N1 C1 C2 C3 -134.20(12) . . . . ?
N2 C2 C3 C4 -178.26(12) . . . . ?
C1 C2 C3 C4 0.53(18) . . . . ?
N2 C2 C3 C8 -0.55(17) . . . . ?
C1 C2 C3 C8 178.24(10) . . . . ?
C8 C3 C4 C5 -1.0(2) . . . . ?
C2 C3 C4 C5 176.65(15) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C4 C3 C8 C9 179.58(12) . . . . ?
C2 C3 C8 C9 1.74(17) . . . . ?
C4 C3 C8 C7 0.27(19) . . . . ?
C2 C3 C8 C7 -177.56(12) . . . . ?
C6 C7 C8 C9 -178.50(17) . . . . ?
C6 C7 C8 C3 0.8(2) . . . . ?
C3 C8 C9 C10 -1.4(2) . . . . ?
C7 C8 C9 C10 177.84(15) . . . . ?
C8 C9 C10 N2 -0.1(2) . . . . ?
N1 C11 C12 C13 -179.94(10) . . . . ?
C11 C12 C13 C12 -178.97(14) . . . 4_655 ?
O1 C1 N1 C11 0.8(2) . . . . ?
C2 C1 N1 C11 179.08(11) . . . . ?
C12 C11 N1 C1 -163.17(12) . . . . ?
C3 C2 N2 C10 -0.98(18) . . . . ?
C1 C2 N2 C10 -179.83(11) . . . . ?
C9 C10 N2 C2 1.4(2) . . . . ?

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.030

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_compound_I4-Ag
_database_code_depnum_ccdc_archive 'CCDC 1506160'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C24 H22 N4 O2 Ag), 2(Cl O4), (C2 H6 O), 2(H2 O)'
_chemical_formula_sum            'C50 H54 Ag2 Cl2 N8 O15'
_chemical_formula_weight         1293.62

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'
Ag Ag 0.1306 4.2820 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2783(3)
_cell_length_b                   11.1478(4)
_cell_length_c                   13.0263(6)
_cell_angle_alpha                100.674(3)
_cell_angle_beta                 101.046(4)
_cell_angle_gamma                91.916(3)
_cell_volume                     1296.18(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    175.00(10)
_cell_measurement_reflns_used    6200
_cell_measurement_theta_min      3.4780
_cell_measurement_theta_max      72.9420

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             654
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1739
_exptl_crystal_size_mid          0.0749
_exptl_crystal_size_min          0.0362
_exptl_absorpt_coefficient_mu    7.665
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.467
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      175.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            9995
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.525
_diffrn_reflns_theta_max         73.708
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5033
_reflns_number_gt                4676
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²+1.0319P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5033
_refine_ls_number_parameters     370
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.26362(2) 0.55003(2) 0.48839(2) 0.02824(7) Uani 1 1 d . . . . .
C1 C 0.3610(3) 0.3116(2) 0.37153(19) 0.0201(5) Uani 1 1 d . . . . .
C2 C 0.4167(3) 0.4100(2) 0.3200(2) 0.0212(5) Uani 1 1 d . . . . .
C3 C 0.4843(3) 0.3840(2) 0.2298(2) 0.0233(5) Uani 1 1 d . . . . .
C4 C 0.4941(3) 0.2645(3) 0.1720(2) 0.0305(6) Uani 1 1 d . . . . .
H4 H 0.4536 0.1969 0.1917 0.037 Uiso 1 1 calc R U . . .
C5 C 0.5630(4) 0.2491(3) 0.0873(3) 0.0399(7) Uani 1 1 d . . . . .
H5 H 0.5690 0.1706 0.0496 0.048 Uiso 1 1 calc R U . . .
C6 C 0.6252(4) 0.3497(3) 0.0560(3) 0.0404(7) Uani 1 1 d . . . . .
H6 H 0.6740 0.3369 -0.0007 0.049 Uiso 1 1 calc R U . . .
C7 C 0.6146(3) 0.4657(3) 0.1081(3) 0.0368(7) Uani 1 1 d . . . . .
H7 H 0.6553 0.5317 0.0862 0.044 Uiso 1 1 calc R U . . .
C8 C 0.5419(3) 0.4868(3) 0.1953(2) 0.0276(6) Uani 1 1 d . . . . .
C9 C 0.5194(3) 0.6045(3) 0.2463(2) 0.0318(6) Uani 1 1 d . . . . .
H9 H 0.5560 0.6725 0.2249 0.038 Uiso 1 1 calc R U . . .
C10 C 0.4441(3) 0.6195(2) 0.3272(2) 0.0296(6) Uani 1 1 d . . . . .
H10 H 0.4255 0.6982 0.3575 0.036 Uiso 1 1 calc R U . . .
C11 C 0.4038(3) 0.1324(2) 0.4478(2) 0.0234(5) Uani 1 1 d . . . . .
H11A H 0.3169 0.0853 0.4033 0.028 Uiso 1 1 calc R U . . .
H11B H 0.3781 0.1711 0.5143 0.028 Uiso 1 1 calc R U . . .
C12 C 0.5248(3) 0.0476(2) 0.4705(2) 0.0251(5) Uani 1 1 d . . . . .
H12A H 0.6126 0.0947 0.5135 0.030 Uiso 1 1 calc R U . . .
H12B H 0.5486 0.0068 0.4039 0.030 Uiso 1 1 calc R U . . .
C13 C 0.1358(3) 0.7394(2) 0.6508(2) 0.0208(5) Uani 1 1 d . . . . .
C14 C 0.0967(3) 0.6151(2) 0.6750(2) 0.0205(5) Uani 1 1 d . . . . .
C15 C 0.0234(3) 0.5976(2) 0.7576(2) 0.0212(5) Uani 1 1 d . . . . .
C16 C -0.0061(3) 0.6938(3) 0.8376(2) 0.0289(6) Uani 1 1 d . . . . .
H16 H 0.0266 0.7741 0.8394 0.035 Uiso 1 1 calc R U . . .
C17 C -0.0822(4) 0.6686(3) 0.9117(2) 0.0365(7) Uani 1 1 d . . . . .
H17 H -0.1022 0.7322 0.9631 0.044 Uiso 1 1 calc R U . . .
C18 C -0.1309(4) 0.5476(3) 0.9115(2) 0.0387(7) Uani 1 1 d . . . . .
H18 H -0.1851 0.5323 0.9614 0.046 Uiso 1 1 calc R U . . .
C19 C -0.0996(3) 0.4529(3) 0.8391(3) 0.0356(7) Uani 1 1 d . . . . .
H19 H -0.1304 0.3732 0.8409 0.043 Uiso 1 1 calc R U . . .
C20 C -0.0203(3) 0.4750(2) 0.7611(2) 0.0265(5) Uani 1 1 d . . . . .
C21 C 0.0177(3) 0.3795(2) 0.6866(2) 0.0303(6) Uani 1 1 d . . . . .
H21 H -0.0106 0.2987 0.6868 0.036 Uiso 1 1 calc R U . . .
C22 C 0.0963(3) 0.4056(2) 0.6141(2) 0.0299(6) Uani 1 1 d . . . . .
H22 H 0.1252 0.3412 0.5678 0.036 Uiso 1 1 calc R U . . .
C23 C 0.0549(3) 0.9414(2) 0.6316(2) 0.0265(6) Uani 1 1 d . . . . .
H23A H 0.1581 0.9702 0.6503 0.032 Uiso 1 1 calc R U . . .
H23B H 0.0013 0.9995 0.6721 0.032 Uiso 1 1 calc R U . . .
C24 C -0.0012(3) 0.9363(2) 0.5134(2) 0.0249(5) Uani 1 1 d . . . . .
H24A H -0.1010 0.8990 0.4929 0.030 Uiso 1 1 calc R U . . .
H24B H 0.0598 0.8856 0.4730 0.030 Uiso 1 1 calc R U . . .
N1 N 0.4502(2) 0.22644(19) 0.39393(18) 0.0228(4) Uani 1 1 d . . . . .
H1 H 0.5353 0.2262 0.3769 0.027 Uiso 1 1 calc R U . . .
N2 N 0.3950(2) 0.52342(19) 0.36528(18) 0.0232(4) Uani 1 1 d . . . . .
N3 N 0.0380(2) 0.82199(19) 0.66069(18) 0.0236(5) Uani 1 1 d . . . . .
H3 H -0.0384 0.8049 0.6851 0.028 Uiso 1 1 calc R U . . .
N4 N 0.1342(2) 0.52269(19) 0.60717(17) 0.0234(4) Uani 1 1 d . . . . .
O1 O 0.23830(19) 0.31750(17) 0.39610(16) 0.0263(4) Uani 1 1 d . . . . .
O2 O 0.2503(2) 0.75673(17) 0.61889(17) 0.0304(4) Uani 1 1 d . . . . .
Cl1 Cl 0.24968(9) 0.92542(7) 0.18245(6) 0.04236(18) Uani 1 1 d . . . . .
O3 O 0.2343(4) 0.8679(2) 0.2695(2) 0.0701(9) Uani 1 1 d . . . . .
O4 O 0.1871(4) 1.0412(2) 0.1974(2) 0.0617(8) Uani 1 1 d . . . . .
O5 O 0.4008(4) 0.9477(4) 0.1810(4) 0.1015(13) Uani 1 1 d . . . . .
O6 O 0.1783(5) 0.8499(3) 0.0854(3) 0.0840(11) Uani 1 1 d . . . . .
C25 C 0.7692(8) 0.8576(6) 0.1243(5) 0.0400(14) Uani 0.5 1 d D . P A 1
H25A H 0.7483 0.7887 0.0647 0.048 Uiso 0.5 1 calc R U P A 1
H25B H 0.8667 0.8499 0.1646 0.048 Uiso 0.5 1 calc R U P A 1
C26 C 0.774(2) 0.9712(11) 0.0807(15) 0.119(9) Uani 0.5 1 d D . P A 1
H26A H 0.8472 0.9674 0.0374 0.179 Uiso 0.5 1 calc R U P A 1
H26B H 0.7983 1.0405 0.1384 0.179 Uiso 0.5 1 calc R U P A 1
H26C H 0.6794 0.9791 0.0381 0.179 Uiso 0.5 1 calc R U P A 1
O7 O 0.6747(11) 0.8476(9) 0.1856(9) 0.120(4) Uani 0.5 1 d . . P A 1
H7A H 0.5911 0.8516 0.1523 0.180 Uiso 0.5 1 calc R U P A 1
O2W O 0.8601(13) 0.9716(12) 0.0843(10) 0.102(4) Uani 0.5 1 d . . P B 2
O1W O 0.7674(9) 0.7673(7) 0.1537(7) 0.086(2) Uani 0.5 1 d . . P C 2


_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 N2 2.178(2) . ?
Ag1 N4 2.189(2) . ?
C1 O1 1.241(3) . ?
C1 N1 1.316(3) . ?
C1 C2 1.514(3) . ?
C2 N2 1.332(3) . ?
C2 C3 1.423(4) . ?
C3 C4 1.419(4) . ?
C3 C8 1.429(4) . ?
C4 C5 1.365(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.361(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.416(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.398(4) . ?
C9 C10 1.361(4) . ?
C9 H9 0.9300 . ?
C10 N2 1.360(3) . ?
C10 H10 0.9300 . ?
C11 N1 1.462(3) . ?
C11 C12 1.512(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C12 1.529(5) 2_656 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O2 1.235(3) . ?
C13 N3 1.321(3) . ?
C13 C14 1.524(3) . ?
C14 N4 1.330(3) . ?
C14 C15 1.417(3) . ?
C15 C20 1.423(4) . ?
C15 C16 1.424(4) . ?
C16 C17 1.363(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.408(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.358(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.416(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.405(4) . ?
C21 C22 1.364(4) . ?
C21 H21 0.9300 . ?
C22 N4 1.364(3) . ?
C22 H22 0.9300 . ?
C23 N3 1.462(3) . ?
C23 C24 1.517(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C24 1.525(5) 2_576 ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
N1 H1 0.8600 . ?
N3 H3 0.8600 . ?
Cl1 O6 1.412(3) . ?
Cl1 O5 1.420(4) . ?
Cl1 O3 1.429(3) . ?
Cl1 O4 1.429(3) . ?
C25 O7 1.309(12) . ?
C25 C26 1.484(12) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O7 H7A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ag1 N4 164.35(8) . . ?
O1 C1 N1 122.7(2) . . ?
O1 C1 C2 119.5(2) . . ?
N1 C1 C2 117.6(2) . . ?
N2 C2 C3 122.7(2) . . ?
N2 C2 C1 114.2(2) . . ?
C3 C2 C1 123.1(2) . . ?
C4 C3 C2 124.3(2) . . ?
C4 C3 C8 119.1(2) . . ?
C2 C3 C8 116.6(2) . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 122.4(3) . . ?
C9 C8 C3 118.7(3) . . ?
C7 C8 C3 118.8(3) . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
N2 C10 C9 122.4(3) . . ?
N2 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
N1 C11 C12 111.0(2) . . ?
N1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C12 110.0(3) . 2_656 ?
C11 C12 H12A 109.7 . . ?
C12 C12 H12A 109.7 2_656 . ?
C11 C12 H12B 109.7 . . ?
C12 C12 H12B 109.7 2_656 . ?
H12A C12 H12B 108.2 . . ?
O2 C13 N3 123.4(2) . . ?
O2 C13 C14 120.1(2) . . ?
N3 C13 C14 116.4(2) . . ?
N4 C14 C15 122.8(2) . . ?
N4 C14 C13 112.5(2) . . ?
C15 C14 C13 124.6(2) . . ?
C14 C15 C20 117.1(2) . . ?
C14 C15 C16 124.3(2) . . ?
C20 C15 C16 118.5(2) . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 122.0(3) . . ?
C21 C20 C15 118.6(2) . . ?
C19 C20 C15 119.4(3) . . ?
C22 C21 C20 119.7(2) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 N4 122.4(3) . . ?
C21 C22 H22 118.8 . . ?
N4 C22 H22 118.8 . . ?
N3 C23 C24 112.1(2) . . ?
N3 C23 H23A 109.2 . . ?
C24 C23 H23A 109.2 . . ?
N3 C23 H23B 109.2 . . ?
C24 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 C24 111.4(3) . 2_576 ?
C23 C24 H24A 109.4 . . ?
C24 C24 H24A 109.4 2_576 . ?
C23 C24 H24B 109.4 . . ?
C24 C24 H24B 109.4 2_576 . ?
H24A C24 H24B 108.0 . . ?
C1 N1 C11 119.7(2) . . ?
C1 N1 H1 120.2 . . ?
C11 N1 H1 120.2 . . ?
C2 N2 C10 119.2(2) . . ?
C2 N2 Ag1 119.15(16) . . ?
C10 N2 Ag1 121.35(18) . . ?
C13 N3 C23 122.4(2) . . ?
C13 N3 H3 118.8 . . ?
C23 N3 H3 118.8 . . ?
C14 N4 C22 119.1(2) . . ?
C14 N4 Ag1 122.66(17) . . ?
C22 N4 Ag1 118.15(18) . . ?
O6 Cl1 O5 109.7(3) . . ?
O6 Cl1 O3 109.8(2) . . ?
O5 Cl1 O3 110.4(3) . . ?
O6 Cl1 O4 110.9(2) . . ?
O5 Cl1 O4 107.6(2) . . ?
O3 Cl1 O4 108.44(18) . . ?
O7 C25 C26 117.5(11) . . ?
O7 C25 H25A 107.9 . . ?
C26 C25 H25A 107.9 . . ?
O7 C25 H25B 107.9 . . ?
C26 C25 H25B 107.9 . . ?
H25A C25 H25B 107.2 . . ?
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 . . ?
C25 O7 H7A 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
O1 C1 C2 N2 44.1(3) . . . . ?
N1 C1 C2 N2 -132.1(2) . . . . ?
O1 C1 C2 C3 -135.0(3) . . . . ?
N1 C1 C2 C3 48.9(4) . . . . ?
N2 C2 C3 C4 -172.4(3) . . . . ?
C1 C2 C3 C4 6.5(4) . . . . ?
N2 C2 C3 C8 5.9(4) . . . . ?
C1 C2 C3 C8 -175.1(2) . . . . ?
C2 C3 C4 C5 -179.1(3) . . . . ?
C8 C3 C4 C5 2.6(4) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C7 -1.8(5) . . . . ?
C5 C6 C7 C8 0.6(5) . . . . ?
C6 C7 C8 C9 -175.5(3) . . . . ?
C6 C7 C8 C3 2.1(5) . . . . ?
C4 C3 C8 C9 174.0(3) . . . . ?
C2 C3 C8 C9 -4.4(4) . . . . ?
C4 C3 C8 C7 -3.6(4) . . . . ?
C2 C3 C8 C7 177.9(3) . . . . ?
C7 C8 C9 C10 177.6(3) . . . . ?
C3 C8 C9 C10 0.0(4) . . . . ?
C8 C9 C10 N2 3.5(5) . . . . ?
N1 C11 C12 C12 178.4(3) . . . 2_656 ?
O2 C13 C14 N4 -36.9(4) . . . . ?
N3 C13 C14 N4 139.6(2) . . . . ?
O2 C13 C14 C15 145.4(3) . . . . ?
N3 C13 C14 C15 -38.0(4) . . . . ?
N4 C14 C15 C20 -4.8(4) . . . . ?
C13 C14 C15 C20 172.7(2) . . . . ?
N4 C14 C15 C16 173.9(3) . . . . ?
C13 C14 C15 C16 -8.7(4) . . . . ?
C14 C15 C16 C17 177.6(3) . . . . ?
C20 C15 C16 C17 -3.8(4) . . . . ?
C15 C16 C17 C18 0.9(5) . . . . ?
C16 C17 C18 C19 1.8(5) . . . . ?
C17 C18 C19 C20 -1.5(5) . . . . ?
C18 C19 C20 C21 178.3(3) . . . . ?
C18 C19 C20 C15 -1.4(4) . . . . ?
C14 C15 C20 C21 3.0(4) . . . . ?
C16 C15 C20 C21 -175.7(3) . . . . ?
C14 C15 C20 C19 -177.2(3) . . . . ?
C16 C15 C20 C19 4.0(4) . . . . ?
C19 C20 C21 C22 -178.9(3) . . . . ?
C15 C20 C21 C22 0.8(4) . . . . ?
C20 C21 C22 N4 -3.3(5) . . . . ?
N3 C23 C24 C24 173.6(3) . . . 2_576 ?
O1 C1 N1 C11 1.4(4) . . . . ?
C2 C1 N1 C11 177.4(2) . . . . ?
C12 C11 N1 C1 -177.3(2) . . . . ?
C3 C2 N2 C10 -2.6(4) . . . . ?
C1 C2 N2 C10 178.3(2) . . . . ?
C3 C2 N2 Ag1 171.56(19) . . . . ?
C1 C2 N2 Ag1 -7.5(3) . . . . ?
C9 C10 N2 C2 -2.3(4) . . . . ?
C9 C10 N2 Ag1 -176.3(2) . . . . ?
O2 C13 N3 C23 1.7(4) . . . . ?
C14 C13 N3 C23 -174.8(2) . . . . ?
C24 C23 N3 C13 84.2(3) . . . . ?
C15 C14 N4 C22 2.5(4) . . . . ?
C13 C14 N4 C22 -175.3(2) . . . . ?
C15 C14 N4 Ag1 -174.72(18) . . . . ?
C13 C14 N4 Ag1 7.6(3) . . . . ?
C21 C22 N4 C14 1.7(4) . . . . ?
C21 C22 N4 Ag1 179.1(2) . . . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.072

_shelxl_version_number           2013-4

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

data_compound_I2-Ag
_database_code_depnum_ccdc_archive 'CCDC 1506157'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Ag, (C22 H18 N4 O2), (Cl O4)'
_chemical_formula_sum            'C22 H18 Ag Cl N4 O6'
_chemical_formula_weight         577.72

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'
Ag Ag 0.1306 4.2820 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

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

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

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

_cell_length_a                   7.7056(2)
_cell_length_b                   14.8087(3)
_cell_length_c                   21.2528(6)
_cell_angle_alpha                90
_cell_angle_beta                 117.472(4)
_cell_angle_gamma                90
_cell_volume                     2151.69(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6088
_cell_measurement_theta_min      3.7480
_cell_measurement_theta_max      73.4450

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3312
_exptl_crystal_size_mid          0.0415
_exptl_crystal_size_min          0.0207
_exptl_absorpt_coefficient_mu    9.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.567
_exptl_absorpt_correction_T_max  1.067
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            12530
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.795
_diffrn_reflns_theta_max         73.881
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4236
_reflns_number_gt                3575
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+1.0968P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4236
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0710
_refine_ls_wR_factor_gt          0.0670
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.74163(3) 1.00508(2) 0.48712(2) 0.04248(8) Uani 1 1 d . . . . .
C1 C 0.6829(4) 0.87546(16) 0.60122(13) 0.0353(5) Uani 1 1 d . . . . .
C2 C 0.5970(3) 0.82793(17) 0.53035(13) 0.0338(5) Uani 1 1 d . . . . .
C3 C 0.5161(3) 0.74015(18) 0.52253(14) 0.0373(5) Uani 1 1 d . . . . .
C4 C 0.5335(4) 0.68678(19) 0.58037(16) 0.0479(7) Uani 1 1 d . . . . .
H4 H 0.6045 0.7079 0.6265 0.057 Uiso 1 1 calc R U . . .
C5 C 0.4451(5) 0.6038(2) 0.56802(18) 0.0572(8) Uani 1 1 d . . . . .
H5 H 0.4574 0.5686 0.6061 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3368(5) 0.5712(2) 0.4990(2) 0.0591(8) Uani 1 1 d . . . . .
H6 H 0.2774 0.5148 0.4917 0.071 Uiso 1 1 calc R U . . .
C7 C 0.3174(4) 0.6205(2) 0.44279(18) 0.0539(8) Uani 1 1 d . . . . .
H7 H 0.2448 0.5978 0.3972 0.065 Uiso 1 1 calc R U . . .
C8 C 0.4062(4) 0.70666(19) 0.45234(15) 0.0425(6) Uani 1 1 d . . . . .
C9 C 0.3871(4) 0.7625(2) 0.39606(15) 0.0477(7) Uani 1 1 d . . . . .
H9 H 0.3142 0.7429 0.3495 0.057 Uiso 1 1 calc R U . . .
C10 C 0.4742(4) 0.8447(2) 0.40914(14) 0.0439(6) Uani 1 1 d . . . . .
H10 H 0.4614 0.8798 0.3710 0.053 Uiso 1 1 calc R U . . .
C11 C 0.9477(4) 0.88858(18) 0.72143(13) 0.0406(6) Uani 1 1 d . . . . .
H11A H 0.9866 0.8393 0.7553 0.049 Uiso 1 1 calc R U . . .
H11B H 0.8517 0.9246 0.7277 0.049 Uiso 1 1 calc R U . . .
C12 C 1.1248(4) 0.94647(18) 0.73672(13) 0.0410(6) Uani 1 1 d . . . . .
H12A H 1.1867 0.9639 0.7863 0.049 Uiso 1 1 calc R U . . .
H12B H 1.2183 0.9111 0.7285 0.049 Uiso 1 1 calc R U . . .
C13 C 1.1217(4) 1.03686(17) 0.64039(13) 0.0344(5) Uani 1 1 d . . . . .
C14 C 1.0730(3) 1.12565(16) 0.60104(13) 0.0332(5) Uani 1 1 d . . . . .
C15 C 1.1730(3) 1.20688(17) 0.63314(14) 0.0360(5) Uani 1 1 d . . . . .
C16 C 1.3109(4) 1.21429(19) 0.70571(15) 0.0430(6) Uani 1 1 d . . . . .
H16 H 1.3412 1.1639 0.7350 0.052 Uiso 1 1 calc R U . . .
C17 C 1.3995(4) 1.2949(2) 0.73271(17) 0.0517(7) Uani 1 1 d . . . . .
H17 H 1.4915 1.2989 0.7802 0.062 Uiso 1 1 calc R U . . .
C18 C 1.3530(4) 1.3720(2) 0.6895(2) 0.0567(8) Uani 1 1 d . . . . .
H18 H 1.4096 1.4272 0.7092 0.068 Uiso 1 1 calc R U . . .
C19 C 1.2262(4) 1.36677(19) 0.61911(19) 0.0536(8) Uani 1 1 d . . . . .
H19 H 1.1996 1.4180 0.5908 0.064 Uiso 1 1 calc R U . . .
C20 C 1.1341(4) 1.28372(18) 0.58862(16) 0.0413(6) Uani 1 1 d . . . . .
C21 C 1.0054(4) 1.2733(2) 0.51593(16) 0.0462(7) Uani 1 1 d . . . . .
H21 H 0.9821 1.3216 0.4851 0.055 Uiso 1 1 calc R U . . .
C22 C 0.9158(4) 1.19345(19) 0.49090(15) 0.0431(6) Uani 1 1 d . . . . .
H22 H 0.8300 1.1885 0.4428 0.052 Uiso 1 1 calc R U . . .
N1 N 0.8589(3) 0.85173(14) 0.65001(11) 0.0398(5) Uani 1 1 d . . . . .
H1 H 0.9236 0.8129 0.6391 0.048 Uiso 1 1 calc R U . . .
N2 N 0.5802(3) 0.87800(14) 0.47636(11) 0.0362(5) Uani 1 1 d . . . . .
N3 N 1.0752(3) 1.02750(15) 0.69296(12) 0.0397(5) Uani 1 1 d . . . . .
H3 H 1.0140 1.0706 0.7014 0.048 Uiso 1 1 calc R U . . .
N4 N 0.9455(3) 1.11959(14) 0.53312(11) 0.0366(5) Uani 1 1 d . . . . .
O1 O 0.5824(3) 0.93239(16) 0.61057(11) 0.0640(7) Uani 1 1 d . . . . .
O2 O 1.2027(4) 0.97849(14) 0.62300(12) 0.0574(6) Uani 1 1 d . . . . .
Cl1 Cl 0.11868(11) 0.62847(4) 0.68354(4) 0.04992(17) Uani 1 1 d . . . . .
O3 O 0.1403(5) 0.71055(18) 0.65288(16) 0.0827(8) Uani 1 1 d . . . . .
O4 O 0.0397(6) 0.6545(2) 0.7298(2) 0.1188(14) Uani 1 1 d . . . . .
O5 O 0.3015(4) 0.5881(2) 0.7233(2) 0.1104(12) Uani 1 1 d . . . . .
O6 O -0.0066(5) 0.5692(2) 0.6325(2) 0.1325(15) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 N2 2.209(2) . ?
Ag1 N4 2.210(2) . ?
Ag1 O1 2.573(2) 3_676 ?
Ag1 O2 2.578(2) 3_776 ?
C1 O1 1.222(3) . ?
C1 N1 1.319(3) . ?
C1 C2 1.511(3) . ?
C2 N2 1.321(3) . ?
C2 C3 1.418(4) . ?
C3 C4 1.415(4) . ?
C3 C8 1.422(4) . ?
C4 C5 1.371(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.348(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.417(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.405(4) . ?
C9 C10 1.355(4) . ?
C9 H9 0.9300 . ?
C10 N2 1.369(3) . ?
C10 H10 0.9300 . ?
C11 N1 1.453(3) . ?
C11 C12 1.514(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N3 1.457(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O2 1.219(3) . ?
C13 N3 1.329(3) . ?
C13 C14 1.510(3) . ?
C14 N4 1.322(3) . ?
C14 C15 1.422(4) . ?
C15 C16 1.417(4) . ?
C15 C20 1.421(4) . ?
C16 C17 1.364(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.404(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.360(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.418(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.407(4) . ?
C21 C22 1.349(4) . ?
C21 H21 0.9300 . ?
C22 N4 1.365(3) . ?
C22 H22 0.9300 . ?
N1 H1 0.8600 . ?
N3 H3 0.8600 . ?
O1 Ag1 2.573(2) 3_676 ?
O2 Ag1 2.578(2) 3_776 ?
Cl1 O6 1.383(3) . ?
Cl1 O5 1.399(3) . ?
Cl1 O3 1.425(2) . ?
Cl1 O4 1.428(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ag1 N4 162.02(8) . . ?
N2 Ag1 O1 86.13(8) . 3_676 ?
N4 Ag1 O1 107.95(8) . 3_676 ?
N2 Ag1 O2 107.95(8) . 3_776 ?
N4 Ag1 O2 86.96(8) . 3_776 ?
O1 Ag1 O2 74.90(7) 3_676 3_776 ?
O1 C1 N1 123.7(2) . . ?
O1 C1 C2 117.7(2) . . ?
N1 C1 C2 118.6(2) . . ?
N2 C2 C3 123.4(2) . . ?
N2 C2 C1 115.3(2) . . ?
C3 C2 C1 120.7(2) . . ?
C4 C3 C2 123.4(2) . . ?
C4 C3 C8 119.2(3) . . ?
C2 C3 C8 117.4(3) . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 123.6(3) . . ?
C9 C8 C3 117.8(3) . . ?
C7 C8 C3 118.6(3) . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 N2 122.6(3) . . ?
C9 C10 H10 118.7 . . ?
N2 C10 H10 118.7 . . ?
N1 C11 C12 112.4(2) . . ?
N1 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
N3 C12 C11 112.6(2) . . ?
N3 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
N3 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
O2 C13 N3 123.7(2) . . ?
O2 C13 C14 118.7(2) . . ?
N3 C13 C14 117.5(2) . . ?
N4 C14 C15 123.1(2) . . ?
N4 C14 C13 114.5(2) . . ?
C15 C14 C13 122.0(2) . . ?
C16 C15 C20 119.0(2) . . ?
C16 C15 C14 123.8(2) . . ?
C20 C15 C14 117.2(2) . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.6(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 123.2(3) . . ?
C21 C20 C15 118.0(2) . . ?
C19 C20 C15 118.9(3) . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 N4 122.9(3) . . ?
C21 C22 H22 118.6 . . ?
N4 C22 H22 118.6 . . ?
C1 N1 C11 122.6(2) . . ?
C1 N1 H1 118.7 . . ?
C11 N1 H1 118.7 . . ?
C2 N2 C10 118.4(2) . . ?
C2 N2 Ag1 124.28(17) . . ?
C10 N2 Ag1 116.84(18) . . ?
C13 N3 C12 122.0(2) . . ?
C13 N3 H3 119.0 . . ?
C12 N3 H3 119.0 . . ?
C14 N4 C22 118.6(2) . . ?
C14 N4 Ag1 123.61(17) . . ?
C22 N4 Ag1 117.03(18) . . ?
C1 O1 Ag1 124.70(17) . 3_676 ?
C13 O2 Ag1 122.09(17) . 3_776 ?
O6 Cl1 O5 110.3(2) . . ?
O6 Cl1 O3 111.7(2) . . ?
O5 Cl1 O3 110.1(2) . . ?
O6 Cl1 O4 110.3(3) . . ?
O5 Cl1 O4 109.3(3) . . ?
O3 Cl1 O4 105.12(17) . . ?

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
O1 C1 C2 N2 71.1(3) . . . . ?
N1 C1 C2 N2 -110.8(3) . . . . ?
O1 C1 C2 C3 -100.4(3) . . . . ?
N1 C1 C2 C3 77.8(3) . . . . ?
N2 C2 C3 C4 -179.7(2) . . . . ?
C1 C2 C3 C4 -8.9(4) . . . . ?
N2 C2 C3 C8 -2.2(4) . . . . ?
C1 C2 C3 C8 168.6(2) . . . . ?
C2 C3 C4 C5 177.7(3) . . . . ?
C8 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C8 0.0(5) . . . . ?
C6 C7 C8 C9 -178.1(3) . . . . ?
C6 C7 C8 C3 -0.1(4) . . . . ?
C4 C3 C8 C9 178.1(2) . . . . ?
C2 C3 C8 C9 0.5(4) . . . . ?
C4 C3 C8 C7 0.0(4) . . . . ?
C2 C3 C8 C7 -177.6(2) . . . . ?
C7 C8 C9 C10 179.1(3) . . . . ?
C3 C8 C9 C10 1.1(4) . . . . ?
C8 C9 C10 N2 -1.3(4) . . . . ?
N1 C11 C12 N3 64.9(3) . . . . ?
O2 C13 C14 N4 63.8(3) . . . . ?
N3 C13 C14 N4 -117.0(3) . . . . ?
O2 C13 C14 C15 -109.7(3) . . . . ?
N3 C13 C14 C15 69.5(3) . . . . ?
N4 C14 C15 C16 -179.5(2) . . . . ?
C13 C14 C15 C16 -6.7(4) . . . . ?
N4 C14 C15 C20 -1.1(4) . . . . ?
C13 C14 C15 C20 171.7(2) . . . . ?
C20 C15 C16 C17 2.3(4) . . . . ?
C14 C15 C16 C17 -179.4(2) . . . . ?
C15 C16 C17 C18 1.1(4) . . . . ?
C16 C17 C18 C19 -3.3(5) . . . . ?
C17 C18 C19 C20 1.9(5) . . . . ?
C18 C19 C20 C21 -178.3(3) . . . . ?
C18 C19 C20 C15 1.5(4) . . . . ?
C16 C15 C20 C21 176.3(2) . . . . ?
C14 C15 C20 C21 -2.2(4) . . . . ?
C16 C15 C20 C19 -3.6(4) . . . . ?
C14 C15 C20 C19 178.0(2) . . . . ?
C19 C20 C21 C22 -177.0(3) . . . . ?
C15 C20 C21 C22 3.2(4) . . . . ?
C20 C21 C22 N4 -0.9(4) . . . . ?
O1 C1 N1 C11 2.8(4) . . . . ?
C2 C1 N1 C11 -175.3(2) . . . . ?
C12 C11 N1 C1 -113.5(3) . . . . ?
C3 C2 N2 C10 2.1(4) . . . . ?
C1 C2 N2 C10 -169.1(2) . . . . ?
C3 C2 N2 Ag1 -169.97(17) . . . . ?
C1 C2 N2 Ag1 18.8(3) . . . . ?
C9 C10 N2 C2 -0.3(4) . . . . ?
C9 C10 N2 Ag1 172.3(2) . . . . ?
O2 C13 N3 C12 2.4(4) . . . . ?
C14 C13 N3 C12 -176.7(2) . . . . ?
C11 C12 N3 C13 -107.9(3) . . . . ?
C15 C14 N4 C22 3.5(4) . . . . ?
C13 C14 N4 C22 -169.9(2) . . . . ?
C15 C14 N4 Ag1 -165.94(17) . . . . ?
C13 C14 N4 Ag1 20.7(3) . . . . ?
C21 C22 N4 C14 -2.5(4) . . . . ?
C21 C22 N4 Ag1 167.6(2) . . . . ?
N1 C1 O1 Ag1 172.01(19) . . . 3_676 ?
C2 C1 O1 Ag1 -9.9(4) . . . 3_676 ?
N3 C13 O2 Ag1 173.88(19) . . . 3_776 ?
C14 C13 O2 Ag1 -7.0(3) . . . 3_776 ?

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

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

data_compound_I6-Ag
_database_code_depnum_ccdc_archive 'CCDC 1506161'
_audit_update_record             
;
2016-09-23 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C26 H26 N4 O2 Ag), (Cl O4)'
_chemical_formula_sum            'C26 H26 Ag Cl N4 O6'
_chemical_formula_weight         633.83

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'
Ag Ag 0.1306 4.2820 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   22.6498(7)
_cell_length_b                   9.4681(3)
_cell_length_c                   13.4041(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.921(3)
_cell_angle_gamma                90
_cell_volume                     2870.78(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7693
_cell_measurement_theta_min      3.8260
_cell_measurement_theta_max      75.7080

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3771
_exptl_crystal_size_mid          0.2755
_exptl_crystal_size_min          0.0588
_exptl_absorpt_coefficient_mu    6.871
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.027
_exptl_absorpt_correction_T_max  0.391
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            14687
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.301
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             5032
_reflns_number_gt                4811
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.954

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1104P)²+0.5103P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 2085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.006(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5032
_refine_ls_number_parameters     417
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1468
_refine_ls_wR_factor_gt          0.1434
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.61209(2) 0.34769(6) 0.43137(4) 0.0768(2) Uani 1 1 d . . . . .
C1 C 0.5439(3) 0.3632(8) 0.6381(5) 0.0601(14) Uani 1 1 d . . . . .
C2 C 0.5909(3) 0.2475(7) 0.6470(6) 0.0555(14) Uani 1 1 d . . . . .
C3 C 0.6005(3) 0.1771(8) 0.7393(5) 0.0583(13) Uani 1 1 d . . . . .
C4 C 0.5739(4) 0.2158(10) 0.8278(6) 0.0736(19) Uani 1 1 d . . . . .
H4 H 0.5479 0.2918 0.8278 0.088 Uiso 1 1 calc R U . . .
C5 C 0.5863(5) 0.1424(13) 0.9135(7) 0.091(3) Uani 1 1 d . . . . .
H5 H 0.5685 0.1683 0.9717 0.109 Uiso 1 1 calc R U . . .
C6 C 0.6254(6) 0.0289(15) 0.9147(8) 0.102(3) Uani 1 1 d . . . . .
H6 H 0.6339 -0.0188 0.9744 0.123 Uiso 1 1 calc R U . . .
C7 C 0.6515(5) -0.0141(12) 0.8297(8) 0.091(3) Uani 1 1 d . . . . .
H7 H 0.6767 -0.0917 0.8313 0.109 Uiso 1 1 calc R U . . .
C8 C 0.6398(4) 0.0607(8) 0.7404(7) 0.0705(18) Uani 1 1 d . . . . .
C9 C 0.6667(4) 0.0259(9) 0.6503(7) 0.075(2) Uani 1 1 d . . . . .
H9 H 0.6920 -0.0512 0.6482 0.090 Uiso 1 1 calc R U . . .
C10 C 0.6555(4) 0.1046(9) 0.5678(6) 0.0726(18) Uani 1 1 d . . . . .
H10 H 0.6742 0.0809 0.5100 0.087 Uiso 1 1 calc R U . . .
C11 C 0.532(3) 0.624(7) 0.631(8) 0.107(7) Uani 0.345(15) 1 d . . P A 1
H11A H 0.4903 0.6083 0.6158 0.128 Uiso 0.345(15) 1 calc R U P A 1
H11B H 0.5478 0.6781 0.5766 0.128 Uiso 0.345(15) 1 calc R U P A 1
C12 C 0.542(2) 0.708(5) 0.733(5) 0.15(2) Uani 0.345(15) 1 d . . P A 1
H12A H 0.5265 0.6531 0.7873 0.175 Uiso 0.345(15) 1 calc R U P A 1
H12B H 0.5835 0.7241 0.7477 0.175 Uiso 0.345(15) 1 calc R U P A 1
C13 C 0.5083(13) 0.853(4) 0.724(4) 0.115(14) Uani 0.345(15) 1 d . . P A 1
H13A H 0.5156 0.9054 0.7859 0.138 Uiso 0.345(15) 1 calc R U P A 1
H13B H 0.5247 0.9078 0.6710 0.138 Uiso 0.345(15) 1 calc R U P A 1
C14 C 0.4420(15) 0.841(3) 0.704(3) 0.102(5) Uani 0.345(15) 1 d D . P A 1
H14A H 0.4250 0.7890 0.7574 0.123 Uiso 0.345(15) 1 calc R U P A 1
H14B H 0.4343 0.7880 0.6422 0.123 Uiso 0.345(15) 1 calc R U P A 1
C15 C 0.412(2) 0.990(3) 0.693(2) 0.089(5) Uani 0.345(15) 1 d D . P A 1
H15A H 0.4336 1.0466 0.6476 0.106 Uiso 0.345(15) 1 calc R U P A 1
H15B H 0.3721 0.9772 0.6633 0.106 Uiso 0.345(15) 1 calc R U P A 1
C16 C 0.4068(6) 1.0752(10) 0.7927(8) 0.092(3) Uani 0.345(15) 1 d D . P A 1
H16A H 0.3868 1.0178 0.8405 0.110 Uiso 0.345(15) 1 calc R U P A 1
H16B H 0.4462 1.0958 0.8207 0.110 Uiso 0.345(15) 1 calc R U P A 1
C11A C 0.5144(13) 0.601(3) 0.641(4) 0.107(7) Uani 0.655(15) 1 d D . P A 2
H11C H 0.4963 0.6039 0.7049 0.128 Uiso 0.655(15) 1 calc R U P A 2
H11D H 0.4840 0.5793 0.5895 0.128 Uiso 0.655(15) 1 calc R U P A 2
C12A C 0.5441(9) 0.7444(17) 0.619(2) 0.115(7) Uani 0.655(15) 1 d D . P A 2
H12C H 0.5650 0.7373 0.5578 0.138 Uiso 0.655(15) 1 calc R U P A 2
H12D H 0.5726 0.7674 0.6729 0.138 Uiso 0.655(15) 1 calc R U P A 2
C13A C 0.4970(9) 0.863(2) 0.6083(18) 0.113(6) Uani 0.655(15) 1 d . . P A 2
H13C H 0.5148 0.9464 0.5802 0.136 Uiso 0.655(15) 1 calc R U P A 2
H13D H 0.4651 0.8325 0.5623 0.136 Uiso 0.655(15) 1 calc R U P A 2
C14A C 0.4715(9) 0.9020(16) 0.7093(17) 0.102(5) Uani 0.655(15) 1 d D . P A 2
H14C H 0.4494 0.8228 0.7342 0.123 Uiso 0.655(15) 1 calc R U P A 2
H14D H 0.5034 0.9239 0.7578 0.123 Uiso 0.655(15) 1 calc R U P A 2
C15A C 0.4307(9) 1.0306(19) 0.6945(14) 0.089(5) Uani 0.655(15) 1 d D . P A 2
H15C H 0.4525 1.1082 0.6668 0.106 Uiso 0.655(15) 1 calc R U P A 2
H15D H 0.3981 1.0071 0.6476 0.106 Uiso 0.655(15) 1 calc R U P A 2
C16A C 0.4068(6) 1.0752(10) 0.7927(8) 0.092(3) Uani 0.655(15) 1 d D . P A 2
H16C H 0.3807 1.0029 0.8166 0.110 Uiso 0.655(15) 1 calc R U P A 2
H16D H 0.4390 1.0885 0.8423 0.110 Uiso 0.655(15) 1 calc R U P A 2
C17 C 0.3942(3) 1.3302(10) 0.8101(5) 0.0681(16) Uani 1 1 d . . . . .
C18 C 0.3582(3) 1.4571(8) 0.7789(6) 0.0597(16) Uani 1 1 d . . . . .
C19 C 0.3320(3) 1.5439(7) 0.8528(6) 0.0634(15) Uani 1 1 d . . . . .
C20 C 0.3347(5) 1.5109(11) 0.9543(7) 0.081(2) Uani 1 1 d . . . . .
H20 H 0.3551 1.4310 0.9772 0.097 Uiso 1 1 calc R U . . .
C21 C 0.3076(6) 1.5955(15) 1.0199(8) 0.101(3) Uani 1 1 d . . . . .
H21 H 0.3100 1.5734 1.0876 0.121 Uiso 1 1 calc R U . . .
C22 C 0.2765(5) 1.7135(13) 0.9876(9) 0.098(3) Uani 1 1 d . . . . .
H22 H 0.2578 1.7692 1.0336 0.118 Uiso 1 1 calc R U . . .
C23 C 0.2729(5) 1.7495(11) 0.8890(10) 0.094(3) Uani 1 1 d . . . . .
H23 H 0.2522 1.8299 0.8681 0.112 Uiso 1 1 calc R U . . .
C24 C 0.3011(4) 1.6637(9) 0.8176(7) 0.0740(19) Uani 1 1 d . . . . .
C25 C 0.2970(5) 1.6931(10) 0.7183(8) 0.087(2) Uani 1 1 d . . . . .
H25 H 0.2757 1.7713 0.6948 0.104 Uiso 1 1 calc R U . . .
C26 C 0.3246(5) 1.6060(10) 0.6527(7) 0.080(2) Uani 1 1 d . . . . .
H26 H 0.3233 1.6292 0.5852 0.096 Uiso 1 1 calc R U . . .
N1 N 0.5627(4) 0.4914(9) 0.6420(10) 0.099(3) Uani 1 1 d . . . . .
H1 H 0.6003 0.4991 0.6533 0.118 Uiso 1 1 calc R U . A 1
N2 N 0.6177(3) 0.2179(7) 0.5649(5) 0.0637(13) Uani 1 1 d . . . . .
N3 N 0.3743(4) 1.2080(8) 0.7770(7) 0.0777(19) Uani 1 1 d D . . . .
H3 H 0.3406 1.2057 0.7445 0.093 Uiso 1 1 calc R U . A 1
N4 N 0.3536(3) 1.4880(7) 0.6838(5) 0.0646(13) Uani 1 1 d . . . . .
O1 O 0.4397(3) 1.3431(10) 0.8642(5) 0.0939(18) Uani 1 1 d . . . . .
O2 O 0.4926(3) 0.3299(11) 0.6290(10) 0.133(4) Uani 1 1 d . . . . .
Cl1 Cl 0.2767(3) 0.6011(9) 0.3337(6) 0.089(4) Uani 0.630(18) 1 d D . P B 1
O3 O 0.3160(8) 0.654(2) 0.4069(11) 0.149(9) Uani 0.630(18) 1 d D . P B 1
O4 O 0.3078(6) 0.4974(15) 0.2762(10) 0.104(4) Uani 0.630(18) 1 d D . P B 1
O5 O 0.2259(8) 0.543(2) 0.3665(16) 0.175(12) Uani 0.630(18) 1 d D . P B 1
O6 O 0.2630(7) 0.7124(14) 0.2612(12) 0.122(6) Uani 0.630(18) 1 d D . P B 1
Cl1A Cl 0.2758(6) 0.6048(15) 0.3300(6) 0.083(7) Uani 0.370(18) 1 d D . P B 2
O3A O 0.3293(12) 0.655(4) 0.293(3) 0.18(2) Uani 0.370(18) 1 d D . P B 2
O4A O 0.2896(17) 0.501(3) 0.407(2) 0.19(2) Uani 0.370(18) 1 d D . P B 2
O5A O 0.2421(16) 0.534(3) 0.251(2) 0.21(3) Uani 0.370(18) 1 d D . P B 2
O6A O 0.2414(12) 0.714(2) 0.371(2) 0.137(12) Uani 0.370(18) 1 d D . P B 2


_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 N2 2.170(6) . ?
Ag1 N4 2.208(6) 2_646 ?
Ag1 O2 2.472(6) 2_656 ?
C1 O2 1.204(10) . ?
C1 N1 1.286(12) . ?
C1 C2 1.528(9) . ?
C2 N2 1.313(10) . ?
C2 C3 1.412(10) . ?
C3 C4 1.407(11) . ?
C3 C8 1.416(10) . ?
C4 C5 1.359(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.404(12) . ?
C7 H7 0.9300 . ?
C8 C9 1.418(13) . ?
C9 C10 1.347(13) . ?
C9 H9 0.9300 . ?
C10 N2 1.372(10) . ?
C10 H10 0.9300 . ?
C11 N1 1.44(7) . ?
C11 C12 1.59(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.57(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.52(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.57(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.57(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N3 1.466(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C11A N1 1.51(4) . ?
C11A C12A 1.55(2) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C12A C13A 1.55(2) . ?
C12A H12C 0.9700 . ?
C12A H12D 0.9700 . ?
C13A C14A 1.54(3) . ?
C13A H13C 0.9700 . ?
C13A H13D 0.9700 . ?
C14A C15A 1.536(18) . ?
C14A H14C 0.9700 . ?
C14A H14D 0.9700 . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?
C17 O1 1.235(9) . ?
C17 N3 1.311(12) . ?
C17 C18 1.500(12) . ?
C18 N4 1.306(11) . ?
C18 C19 1.438(10) . ?
C19 C20 1.394(13) . ?
C19 C24 1.403(12) . ?
C20 C21 1.358(15) . ?
C20 H20 0.9300 . ?
C21 C22 1.38(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.363(19) . ?
C22 H22 0.9300 . ?
C23 C24 1.430(12) . ?
C23 H23 0.9300 . ?
C24 C25 1.358(16) . ?
C25 C26 1.379(15) . ?
C25 H25 0.9300 . ?
C26 N4 1.351(11) . ?
C26 H26 0.9300 . ?
N1 H1 0.8600 . ?
N3 H3 0.8600 . ?
N4 Ag1 2.208(6) 2_666 ?
O2 Ag1 2.472(6) 2_656 ?
Cl1 O5 1.366(13) . ?
Cl1 O3 1.387(13) . ?
Cl1 O4 1.451(13) . ?
Cl1 O6 1.455(14) . ?
Cl1A O3A 1.42(2) . ?
Cl1A O6A 1.42(2) . ?
Cl1A O5A 1.44(2) . ?
Cl1A O4A 1.45(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ag1 N4 155.5(2) . 2_646 ?
N2 Ag1 O2 104.2(3) . 2_656 ?
N4 Ag1 O2 100.3(3) 2_646 2_656 ?
O2 C1 N1 124.6(8) . . ?
O2 C1 C2 118.9(8) . . ?
N1 C1 C2 116.5(7) . . ?
N2 C2 C3 125.2(6) . . ?
N2 C2 C1 116.0(6) . . ?
C3 C2 C1 118.8(6) . . ?
C4 C3 C2 124.2(7) . . ?
C4 C3 C8 119.3(7) . . ?
C2 C3 C8 116.5(7) . . ?
C5 C4 C3 120.1(8) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.6(10) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 121.3(9) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.2(10) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 C3 119.5(9) . . ?
C7 C8 C9 122.6(8) . . ?
C3 C8 C9 117.9(7) . . ?
C10 C9 C8 120.0(7) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 N2 123.2(8) . . ?
C9 C10 H10 118.4 . . ?
N2 C10 H10 118.4 . . ?
N1 C11 C12 108(6) . . ?
N1 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
N1 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C13 C12 C11 109(4) . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
C14 C13 C12 114(3) . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 112(3) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 116(3) . . ?
C16 C15 H15A 108.3 . . ?
C14 C15 H15A 108.3 . . ?
C16 C15 H15B 108.3 . . ?
C14 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
N3 C16 C15 112.1(15) . . ?
N3 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
N3 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N1 C11A C12A 106.4(17) . . ?
N1 C11A H11C 110.4 . . ?
C12A C11A H11C 110.4 . . ?
N1 C11A H11D 110.4 . . ?
C12A C11A H11D 110.4 . . ?
H11C C11A H11D 108.6 . . ?
C11A C12A C13A 110.5(19) . . ?
C11A C12A H12C 109.6 . . ?
C13A C12A H12C 109.6 . . ?
C11A C12A H12D 109.6 . . ?
C13A C12A H12D 109.6 . . ?
H12C C12A H12D 108.1 . . ?
C14A C13A C12A 112.2(19) . . ?
C14A C13A H13C 109.2 . . ?
C12A C13A H13C 109.2 . . ?
C14A C13A H13D 109.2 . . ?
C12A C13A H13D 109.2 . . ?
H13C C13A H13D 107.9 . . ?
C15A C14A C13A 109.0(17) . . ?
C15A C14A H14C 109.9 . . ?
C13A C14A H14C 109.9 . . ?
C15A C14A H14D 109.9 . . ?
C13A C14A H14D 109.9 . . ?
H14C C14A H14D 108.3 . . ?
C14A C15A H15C 109.6 . . ?
C14A C15A H15D 109.6 . . ?
H15C C15A H15D 108.1 . . ?
O1 C17 N3 123.3(9) . . ?
O1 C17 C18 120.7(9) . . ?
N3 C17 C18 116.1(7) . . ?
N4 C18 C19 121.9(7) . . ?
N4 C18 C17 117.9(7) . . ?
C19 C18 C17 120.2(7) . . ?
C20 C19 C24 120.4(8) . . ?
C20 C19 C18 123.1(8) . . ?
C24 C19 C18 116.5(8) . . ?
C21 C20 C19 120.0(11) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 121.0(11) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 120.8(9) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.0(10) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C19 120.2(8) . . ?
C25 C24 C23 121.9(9) . . ?
C19 C24 C23 117.8(9) . . ?
C24 C25 C26 119.5(8) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
N4 C26 C25 121.8(9) . . ?
N4 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C1 N1 C11 132(3) . . ?
C1 N1 C11A 114.2(11) . . ?
C1 N1 H1 114.2 . . ?
C11 N1 H1 114.2 . . ?
C2 N2 C10 117.2(7) . . ?
C2 N2 Ag1 124.1(5) . . ?
C10 N2 Ag1 118.5(5) . . ?
C17 N3 C16 123.1(8) . . ?
C17 N3 H3 118.4 . . ?
C16 N3 H3 118.4 . . ?
C18 N4 C26 120.0(7) . . ?
C18 N4 Ag1 122.3(5) . 2_666 ?
C26 N4 Ag1 117.7(6) . 2_666 ?
C1 O2 Ag1 156.9(9) . 2_656 ?
O5 Cl1 O3 116.0(12) . . ?
O5 Cl1 O4 109.8(10) . . ?
O3 Cl1 O4 108.0(10) . . ?
O5 Cl1 O6 110.6(12) . . ?
O3 Cl1 O6 108.5(10) . . ?
O4 Cl1 O6 103.2(9) . . ?
O3A Cl1A O6A 112.5(15) . . ?
O3A Cl1A O5A 109.5(15) . . ?
O6A Cl1A O5A 109.8(15) . . ?
O3A Cl1A O4A 108.7(15) . . ?
O6A Cl1A O4A 108.8(14) . . ?
O5A Cl1A O4A 107.3(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 N2 99.6(11) . . . . ?
N1 C1 C2 N2 -81.0(10) . . . . ?
O2 C1 C2 C3 -77.7(11) . . . . ?
N1 C1 C2 C3 101.7(10) . . . . ?
N2 C2 C3 C4 176.1(8) . . . . ?
C1 C2 C3 C4 -6.8(11) . . . . ?
N2 C2 C3 C8 -3.7(11) . . . . ?
C1 C2 C3 C8 173.4(6) . . . . ?
C2 C3 C4 C5 -179.4(9) . . . . ?
C8 C3 C4 C5 0.4(13) . . . . ?
C3 C4 C5 C6 0.2(17) . . . . ?
C4 C5 C6 C7 -1(2) . . . . ?
C5 C6 C7 C8 2(2) . . . . ?
C6 C7 C8 C3 -1.2(17) . . . . ?
C6 C7 C8 C9 177.8(11) . . . . ?
C4 C3 C8 C7 0.1(13) . . . . ?
C2 C3 C8 C7 179.9(9) . . . . ?
C4 C3 C8 C9 -178.9(8) . . . . ?
C2 C3 C8 C9 0.9(11) . . . . ?
C7 C8 C9 C10 -177.6(10) . . . . ?
C3 C8 C9 C10 1.4(14) . . . . ?
C8 C9 C10 N2 -1.3(16) . . . . ?
N1 C11 C12 C13 -179(4) . . . . ?
C11 C12 C13 C14 61(6) . . . . ?
C12 C13 C14 C15 -179(4) . . . . ?
C13 C14 C15 C16 -73(4) . . . . ?
C14 C15 C16 N3 -176(3) . . . . ?
N1 C11A C12A C13A 176(2) . . . . ?
C11A C12A C13A C14A 71(3) . . . . ?
C12A C13A C14A C15A 173.8(17) . . . . ?
O1 C17 C18 N4 116.1(9) . . . . ?
N3 C17 C18 N4 -64.0(10) . . . . ?
O1 C17 C18 C19 -61.5(11) . . . . ?
N3 C17 C18 C19 118.4(8) . . . . ?
N4 C18 C19 C20 177.9(8) . . . . ?
C17 C18 C19 C20 -4.6(11) . . . . ?
N4 C18 C19 C24 0.0(11) . . . . ?
C17 C18 C19 C24 177.5(7) . . . . ?
C24 C19 C20 C21 -0.4(14) . . . . ?
C18 C19 C20 C21 -178.2(9) . . . . ?
C19 C20 C21 C22 0.8(18) . . . . ?
C20 C21 C22 C23 -0.9(19) . . . . ?
C21 C22 C23 C24 0.7(18) . . . . ?
C20 C19 C24 C25 -178.0(9) . . . . ?
C18 C19 C24 C25 0.0(12) . . . . ?
C20 C19 C24 C23 0.1(12) . . . . ?
C18 C19 C24 C23 178.1(8) . . . . ?
C22 C23 C24 C25 177.8(11) . . . . ?
C22 C23 C24 C19 -0.3(15) . . . . ?
C19 C24 C25 C26 -1.5(15) . . . . ?
C23 C24 C25 C26 -179.5(10) . . . . ?
C24 C25 C26 N4 3.1(17) . . . . ?
O2 C1 N1 C11 -5(6) . . . . ?
C2 C1 N1 C11 176(6) . . . . ?
O2 C1 N1 C11A 4(3) . . . . ?
C2 C1 N1 C11A -176(2) . . . . ?
C12 C11 N1 C1 118(5) . . . . ?
C12 C11 N1 C11A 93(19) . . . . ?
C12A C11A N1 C1 -166(2) . . . . ?
C12A C11A N1 C11 -6(16) . . . . ?
C3 C2 N2 C10 3.9(11) . . . . ?
C1 C2 N2 C10 -173.3(7) . . . . ?
C3 C2 N2 Ag1 -170.2(5) . . . . ?
C1 C2 N2 Ag1 12.7(9) . . . . ?
C9 C10 N2 C2 -1.2(14) . . . . ?
C9 C10 N2 Ag1 173.2(8) . . . . ?
O1 C17 N3 C16 -5.9(15) . . . . ?
C18 C17 N3 C16 174.2(9) . . . . ?
C15 C16 N3 C17 -130(2) . . . . ?
C19 C18 N4 C26 1.6(12) . . . . ?
C17 C18 N4 C26 -176.0(8) . . . . ?
C19 C18 N4 Ag1 -175.4(5) . . . 2_666 ?
C17 C18 N4 Ag1 7.0(9) . . . 2_666 ?
C25 C26 N4 C18 -3.2(14) . . . . ?
C25 C26 N4 Ag1 173.9(8) . . . 2_666 ?
N1 C1 O2 Ag1 35(3) . . . 2_656 ?
C2 C1 O2 Ag1 -145.1(19) . . . 2_656 ?

_refine_diff_density_max         1.159
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.105

_shelxl_version_number           2013-4

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

data_compound4f
_database_code_depnum_ccdc_archive 'CCDC 1506158'
_audit_update_record             
;
2016-12-22 deposited with the CCDC.
2017-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        1f
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C27 H28 N4 O2 Ag), (Cl O4)'
_chemical_formula_sum            'C27 H28 Ag Cl N4 O6'
_chemical_formula_weight         647.85

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'
Ag Ag 0.1306 4.2820 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'

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

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

_cell_length_a                   12.2945(6)
_cell_length_b                   18.6277(8)
_cell_length_c                   11.5504(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2645.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3262
_cell_measurement_theta_min      4.4650
_cell_measurement_theta_max      73.3760

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6315
_exptl_crystal_size_mid          0.4528
_exptl_crystal_size_min          0.3581
_exptl_absorpt_coefficient_mu    7.470
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.290
_exptl_absorpt_correction_T_max  0.417
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5953
_diffrn_reflns_number            6668
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.504
_diffrn_reflns_theta_max         73.539
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2604
_reflns_number_gt                2337
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1165P)²+4.1262P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2604
_refine_ls_number_parameters     180
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1849
_refine_ls_wR_factor_gt          0.1788
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.2500 0.5000 0.59617(5) 0.0451(3) Uani 1 2 d S T P . .
C1 C 0.5245(3) 0.56011(19) 0.6155(3) 0.0324(8) Uani 1 1 d . . . . .
C2 C 0.4433(3) 0.62073(19) 0.6117(3) 0.0292(7) Uani 1 1 d . . . . .
C3 C 0.4810(3) 0.6932(2) 0.6051(3) 0.0327(8) Uani 1 1 d . . . . .
C4 C 0.5913(4) 0.7127(3) 0.6044(4) 0.0489(11) Uani 1 1 d . . . . .
H4 H 0.6451 0.6777 0.6098 0.059 Uiso 1 1 calc R U . . .
C5 C 0.6194(5) 0.7847(3) 0.5955(5) 0.0678(17) Uani 1 1 d . . . . .
H5 H 0.6925 0.7975 0.5958 0.081 Uiso 1 1 calc R U . . .
C6 C 0.5416(6) 0.8374(3) 0.5862(5) 0.0650(16) Uani 1 1 d . . . . .
H6 H 0.5629 0.8850 0.5773 0.078 Uiso 1 1 calc R U . . .
C7 C 0.4348(5) 0.8208(2) 0.5897(4) 0.0563(14) Uani 1 1 d . . . . .
H7 H 0.3827 0.8569 0.5852 0.068 Uiso 1 1 calc R U . . .
C8 C 0.4025(4) 0.7480(2) 0.6003(3) 0.0401(10) Uani 1 1 d . . . . .
C9 C 0.2931(5) 0.7290(3) 0.6077(5) 0.0563(13) Uani 1 1 d . . . . .
H9 H 0.2398 0.7644 0.6086 0.068 Uiso 1 1 calc R U . . .
C10 C 0.2647(4) 0.6594(4) 0.6135(6) 0.0564(15) Uani 1 1 d . . . . .
H10 H 0.1911 0.6480 0.6164 0.068 Uiso 1 1 calc R U . . .
C11 C 0.5859(4) 0.4535(2) 0.7206(5) 0.0499(11) Uani 1 1 d . . . . .
H11A H 0.6258 0.4596 0.7924 0.060 Uiso 1 1 calc R U . . .
H11B H 0.6381 0.4512 0.6578 0.060 Uiso 1 1 calc R U . . .
C12 C 0.5226(3) 0.3846(2) 0.7252(4) 0.0428(10) Uani 1 1 d . . . . .
H12A H 0.4815 0.3796 0.6540 0.051 Uiso 1 1 calc R U . . .
H12B H 0.4709 0.3873 0.7885 0.051 Uiso 1 1 calc R U . . .
C13 C 0.5928(3) 0.3184(2) 0.7413(4) 0.0416(10) Uani 1 1 d . . . . .
H13A H 0.6426 0.3145 0.6764 0.050 Uiso 1 1 calc R U . . .
H13B H 0.6359 0.3239 0.8111 0.050 Uiso 1 1 calc R U . . .
C14 C 0.5276(5) 0.2500 0.7500 0.0463(14) Uani 1 2 d S T P . .
H14A H 0.4809 0.2533 0.8175 0.056 Uiso 0.5 1 calc R U P . .
H14B H 0.4809 0.2467 0.6825 0.056 Uiso 0.5 1 calc R U P . .
N1 N 0.5138(3) 0.51522(19) 0.7031(3) 0.0404(8) Uani 1 1 d . . . . .
H1 H 0.4623 0.5225 0.7521 0.049 Uiso 1 1 calc R U . . .
N2 N 0.3390(3) 0.60405(18) 0.6153(3) 0.0391(8) Uani 1 1 d . . . . .
O1 O 0.5970(3) 0.55708(17) 0.5414(3) 0.0485(8) Uani 1 1 d . . . . .
Cl1 Cl 0.2500 0.5000 0.9358(2) 0.0628(6) Uani 1 2 d DS T P . .
O2 O 0.3659(11) 0.5057(7) 0.9123(12) 0.137(4) Uani 0.5 1 d D U P . .
O3 O 0.2393(11) 0.4541(8) 1.0284(13) 0.137(4) Uani 0.5 1 d D U P . .
O4 O 0.2279(12) 0.5704(7) 0.9839(13) 0.137(4) Uani 0.5 1 d D U P . .
O5 O 0.1959(11) 0.4912(7) 0.8406(11) 0.137(4) Uani 0.5 1 d D U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 N2 2.237(3) . ?
Ag1 N2 2.237(3) 2_565 ?
C1 O1 1.237(5) . ?
C1 N1 1.320(5) . ?
C1 C2 1.507(5) . ?
C2 N2 1.320(5) . ?
C2 C3 1.429(5) . ?
C3 C4 1.405(6) . ?
C3 C8 1.405(6) . ?
C4 C5 1.388(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.350(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.419(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(7) . ?
C9 C10 1.343(9) . ?
C9 H9 0.9300 . ?
C10 N2 1.377(7) . ?
C10 H10 0.9300 . ?
C11 N1 1.465(5) . ?
C11 C12 1.501(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.518(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.508(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C13 1.508(5) 4_556 ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N1 H1 0.8600 . ?
Cl1 O5 1.296(13) 2_565 ?
Cl1 O5 1.296(13) . ?
Cl1 O3 1.376(12) . ?
Cl1 O3 1.376(12) 2_565 ?
Cl1 O4 1.450(13) 2_565 ?
Cl1 O4 1.450(13) . ?
Cl1 O2 1.454(13) . ?
Cl1 O2 1.454(13) 2_565 ?
O2 O5 1.12(2) 2_565 ?
O3 O4 0.80(2) 2_565 ?
O3 O3 1.73(3) 2_565 ?
O4 O3 0.80(2) 2_565 ?
O5 O2 1.12(2) 2_565 ?
O5 O5 1.37(3) 2_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ag1 N2 168.67(19) . 2_565 ?
O1 C1 N1 125.0(4) . . ?
O1 C1 C2 119.4(3) . . ?
N1 C1 C2 115.5(3) . . ?
N2 C2 C3 122.6(4) . . ?
N2 C2 C1 117.8(3) . . ?
C3 C2 C1 119.7(3) . . ?
C4 C3 C8 118.4(4) . . ?
C4 C3 C2 123.9(4) . . ?
C8 C3 C2 117.7(4) . . ?
C5 C4 C3 119.3(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 121.5(6) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 C6 C5 120.7(5) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.6(5) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C3 118.4(4) . . ?
C9 C8 C7 121.2(5) . . ?
C3 C8 C7 120.3(5) . . ?
C10 C9 C8 119.9(5) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 N2 123.4(5) . . ?
C9 C10 H10 118.3 . . ?
N2 C10 H10 118.3 . . ?
N1 C11 C12 111.2(4) . . ?
N1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 113.9(4) . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 113.1(4) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C13 115.7(5) 4_556 . ?
C13 C14 H14A 108.3 4_556 . ?
C13 C14 H14A 108.3 . . ?
C13 C14 H14B 108.3 4_556 . ?
C13 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C1 N1 C11 122.9(4) . . ?
C1 N1 H1 118.6 . . ?
C11 N1 H1 118.6 . . ?
C2 N2 C10 117.9(4) . . ?
C2 N2 Ag1 132.5(3) . . ?
C10 N2 Ag1 108.8(3) . . ?
O5 Cl1 O5 63.9(12) 2_565 . ?
O5 Cl1 O3 141.9(8) 2_565 . ?
O5 Cl1 O3 122.2(9) . . ?
O5 Cl1 O3 122.2(9) 2_565 2_565 ?
O5 Cl1 O3 141.9(8) . 2_565 ?
O3 Cl1 O3 77.9(15) . 2_565 ?
O5 Cl1 O4 110.1(8) 2_565 2_565 ?
O5 Cl1 O4 107.9(9) . 2_565 ?
O3 Cl1 O4 32.6(9) . 2_565 ?
O3 Cl1 O4 104.3(8) 2_565 2_565 ?
O5 Cl1 O4 107.9(9) 2_565 . ?
O5 Cl1 O4 110.1(8) . . ?
O3 Cl1 O4 104.3(8) . . ?
O3 Cl1 O4 32.6(9) 2_565 . ?
O4 Cl1 O4 135.0(12) 2_565 . ?
O5 Cl1 O2 47.9(9) 2_565 . ?
O5 Cl1 O2 110.7(8) . . ?
O3 Cl1 O2 106.5(7) . . ?
O3 Cl1 O2 90.4(9) 2_565 . ?
O4 Cl1 O2 87.4(7) 2_565 . ?
O4 Cl1 O2 100.9(7) . . ?
O5 Cl1 O2 110.7(8) 2_565 2_565 ?
O5 Cl1 O2 47.9(9) . 2_565 ?
O3 Cl1 O2 90.4(9) . 2_565 ?
O3 Cl1 O2 106.5(7) 2_565 2_565 ?
O4 Cl1 O2 100.9(7) 2_565 2_565 ?
O4 Cl1 O2 87.4(7) . 2_565 ?
O2 Cl1 O2 158.5(12) . 2_565 ?
O5 O2 Cl1 58.7(9) 2_565 . ?
O4 O3 Cl1 78.8(10) 2_565 . ?
O4 O3 O3 119.3(18) 2_565 2_565 ?
Cl1 O3 O3 51.0(8) . 2_565 ?
O3 O4 Cl1 68.6(11) 2_565 . ?
O2 O5 Cl1 73.5(8) 2_565 . ?
O2 O5 O5 130.0(9) 2_565 2_565 ?
Cl1 O5 O5 58.1(6) . 2_565 ?

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
O1 C1 C2 N2 128.7(4) . . . . ?
N1 C1 C2 N2 -53.9(5) . . . . ?
O1 C1 C2 C3 -51.6(5) . . . . ?
N1 C1 C2 C3 125.7(4) . . . . ?
N2 C2 C3 C4 178.2(4) . . . . ?
C1 C2 C3 C4 -1.4(6) . . . . ?
N2 C2 C3 C8 -1.1(5) . . . . ?
C1 C2 C3 C8 179.2(3) . . . . ?
C8 C3 C4 C5 -1.9(6) . . . . ?
C2 C3 C4 C5 178.7(4) . . . . ?
C3 C4 C5 C6 -0.7(8) . . . . ?
C4 C5 C6 C7 2.5(8) . . . . ?
C5 C6 C7 C8 -1.6(8) . . . . ?
C4 C3 C8 C9 -176.4(4) . . . . ?
C2 C3 C8 C9 3.0(6) . . . . ?
C4 C3 C8 C7 2.8(6) . . . . ?
C2 C3 C8 C7 -177.8(4) . . . . ?
C6 C7 C8 C9 178.1(5) . . . . ?
C6 C7 C8 C3 -1.1(7) . . . . ?
C3 C8 C9 C10 -3.2(8) . . . . ?
C7 C8 C9 C10 177.6(5) . . . . ?
C8 C9 C10 N2 1.6(10) . . . . ?
N1 C11 C12 C13 179.1(4) . . . . ?
C11 C12 C13 C14 177.9(4) . . . . ?
C12 C13 C14 C13 176.4(4) . . . 4_556 ?
O1 C1 N1 C11 -2.5(7) . . . . ?
C2 C1 N1 C11 -179.7(4) . . . . ?
C12 C11 N1 C1 -122.7(5) . . . . ?
C3 C2 N2 C10 -0.5(6) . . . . ?
C1 C2 N2 C10 179.1(4) . . . . ?
C3 C2 N2 Ag1 168.2(3) . . . . ?
C1 C2 N2 Ag1 -12.2(5) . . . . ?
C9 C10 N2 C2 0.4(9) . . . . ?
C9 C10 N2 Ag1 -170.9(6) . . . . ?
O5 Cl1 O2 O5 12.2(17) . . . 2_565 ?
O3 Cl1 O2 O5 147.1(12) . . . 2_565 ?
O3 Cl1 O2 O5 -135.4(12) 2_565 . . 2_565 ?
O4 Cl1 O2 O5 120.3(11) 2_565 . . 2_565 ?
O4 Cl1 O2 O5 -104.3(12) . . . 2_565 ?
O2 Cl1 O2 O5 6.8(9) 2_565 . . 2_565 ?
O5 Cl1 O3 O4 -16(3) 2_565 . . 2_565 ?
O5 Cl1 O3 O4 72(2) . . . 2_565 ?
O3 Cl1 O3 O4 -143(2) 2_565 . . 2_565 ?
O4 Cl1 O3 O4 -162.7(14) . . . 2_565 ?
O2 Cl1 O3 O4 -57(2) . . . 2_565 ?
O2 Cl1 O3 O4 109.9(19) 2_565 . . 2_565 ?
O5 Cl1 O3 O3 127.6(13) 2_565 . . 2_565 ?
O5 Cl1 O3 O3 -144.7(9) . . . 2_565 ?
O4 Cl1 O3 O3 143(2) 2_565 . . 2_565 ?
O4 Cl1 O3 O3 -19.4(12) . . . 2_565 ?
O2 Cl1 O3 O3 86.8(9) . . . 2_565 ?
O2 Cl1 O3 O3 -106.8(8) 2_565 . . 2_565 ?
O5 Cl1 O4 O3 -122.3(19) 2_565 . . 2_565 ?
O5 Cl1 O4 O3 169.7(19) . . . 2_565 ?
O3 Cl1 O4 O3 37(3) . . . 2_565 ?
O4 Cl1 O4 O3 24.0(17) 2_565 . . 2_565 ?
O2 Cl1 O4 O3 -73(2) . . . 2_565 ?
O2 Cl1 O4 O3 127(2) 2_565 . . 2_565 ?
O5 Cl1 O5 O2 -167.3(18) 2_565 . . 2_565 ?
O3 Cl1 O5 O2 56.1(14) . . . 2_565 ?
O3 Cl1 O5 O2 -58(2) 2_565 . . 2_565 ?
O4 Cl1 O5 O2 88.6(12) 2_565 . . 2_565 ?
O4 Cl1 O5 O2 -66.6(11) . . . 2_565 ?
O2 Cl1 O5 O2 -177.3(4) . . . 2_565 ?
O3 Cl1 O5 O5 -136.7(10) . . . 2_565 ?
O3 Cl1 O5 O5 109.6(16) 2_565 . . 2_565 ?
O4 Cl1 O5 O5 -104.1(10) 2_565 . . 2_565 ?
O4 Cl1 O5 O5 100.6(11) . . . 2_565 ?
O2 Cl1 O5 O5 -10.1(14) . . . 2_565 ?
O2 Cl1 O5 O5 167.3(18) 2_565 . . 2_565 ?

_refine_diff_density_max         1.550
_refine_diff_density_min         -1.123
_refine_diff_density_rms         0.130

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol, water'
